Financial Transformation & Human Design with Kiera Doyle

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Financial Transformation & Human Design with Kiera Doyle

For over seven years now, I’ve watched the amazing transformations that take place when someone embarks on a financial wellness journey. You may decide to get financially fit because of a particular pain point, like student loan debt or lack or savings, but once you start focusing on your money, it’s amazing what different doors and opportunities can open up.

Joining me today is Kiera Doyle, hairdresser, host of the Beauty Therapy podcast, and Human Design reader, to talk about her journey toward financial fitness, and how it led to a truly unique side hustle she never anticipated. If you know anything about human design and you are curious about mine, stay tuned toward the end to hear what Kiera has to say about me.

What Are We Drinking?

Kiera — Cran-Raspberry La Croix

Shannon — Black Cherry Schweppes

Podcast Notes

  • Kiera has been a Financial Gym client for a while now.
  • She is a hairdresser, facilitator, and writer, and she has had a winding career of many things. She went to school for writing and did public relations (PR) for a little while. She moved to New York and got certified to teach yoga. 
  • After Kiera was certified for yoga, she realized she wanted to go to cosmetology school. Cosmetology school wasn’t easy, but it was always in the back of her mind. She always felt limited by anything that cost money and felt like she couldn’t do it.
  • Kiera didn’t grow up with an abundant amount of money and had limiting beliefs around it. 
  • Kiera made her way to New York in a very scrappy way. She thought she had an apartment, but she lost it and lived on a couch for six months. She waitressed during that time so she could afford to get her own apartment.
  • She always wanted to move to New York. Her parents and grandparents were born there and she had family in Brooklyn.
  • Kiera lived in Boston, graduated college, and was working at a job she didn’t love. She was pretty good at PR and decided she wanted to do that on her own.
  • She went through a very hard breakup and that was all she needed to pack up and move to New York. She ended up living with a high-class call girl and she didn’t know it. Her roommate was one of her clients when she was doing PR, and when Kiera went independent she signed a contract with her. 
  • Kiera knew her as someone in the fashion business. Her roommate would go into homes and redo wardrobes. Kiera wrote up a business plan for her and gave her the price. Her roommate couldn’t afford it and instead offered her a room in her Hoboken apartment for three months.
  • The place was beautiful. Kiera drove from Boston at 3:00 in the morning. At the time, Kim Kardashian lived on the same floor. She knew something was up. Within two weeks, the door opened and a middle aged guy came in and asked her, “What are you doing in my apartment?”.
  • It was then that she found out her roommate was a high class call girl and this was her sugar daddy’s apartment. She knew he was going to be in Europe for three months, so she stole his keys and set the whole thing up so Kiera could live there for free and work for her for free.
  • Kiera had a friend that lived near Hoboken and she was just getting off her shift. They had planned to get a drink together and Kiera called her and told her what happened. Her friend said to stay at her place.
  • Kiera’s friends convinced her to apply at their restaurant, even though she didn’t have any experience. She decided if she got the job, she would stay, if not, she would move back to Rhode Island with her parents. At the time she only had one PR contract and was making $1,500 a month. She didn’t make enough to live.
  • Kiera had a fake reference and interviewed at the restaurant and she got the job on the spot. It turned out that it was a fine dining restaurant and she stayed less than a month.
  • Kiera moved to New York on another couch and got a job at another restaurant. She served for about three years to support herself. There was something that felt really good to become good at something she was originally not good at. 
  • Kiera worked in a hair salon in Boston and always loved the beauty industry. She would have gone straight to cosmetology school after high school, but she didn’t have a say in it, because her parents made her go to college. It was always on her to do list.
  • While living with her friend, she moved into a bedroom that opened up and she went through cosmetology school and got licensed. After getting licensed, she had to go through an unpaid apprenticeship.
  • Kiera’s hairdressing job led her to a corporate job she has now. 
  • She worked for a big beauty brand and they put on large education event for hairdressers and she was asked to give a class to 2,000 hairdressers over three classes. Kiera considered it to be the shining moment in her career.
  • When she stepped off the stage, she felt a little depressed, because she realized she wasn’t really happy. Kiera was looking for a community, because she felt lost spiritually and financially and she felt disconnected from her body. She had been giving everything she had over the last 10 years trying to survive in New York.
  • Kiera found an event through Awake the Space and she decided to go to it. There was a segment from the Financial Gym and that is where she met Shannon.
  • Very soon after that, Kiera signed up for an appointment with Bridget, and she slept better than she had in a long time after that appointment.
  • A lot happened after Kiera found Martinis and Your Money. She had never had an opportunity to connect with like-minded people. She was opened up to podcasts and the information that is out there. 
  • Kiera joined the Gym in February 2018, and after that her life started transforming. 
  • The money part is easy, because numbers are numbers. That leads to other areas of self improvement. 
  • Kiera was comfortable being very stressed financially. New York is expensive and she wasn’t making enough money. She wasn’t looking at where she was spending her money and she was paying interest on her credit cards. 
  • Kiera doesn’t tend to spend a lot of money on herself, but she spends a lot of money. She tends to spend it on going out, gifts, travel, groceries/food, and she is very generous. She is learning to be very mindful of where she is at and she is learning to not say yes to every trip she is invited on. 
  • She is a perfect example of someone who has improved so much, but she still needs her trainer. She is a different person than who she was two years ago.
  • After she started working on her finances, Kiera had to ask herself what else needed to be worked on. Her finances were masking other things she was uncomfortable with. 
  • As she started doing the work and removing the credit card pacifier, she realized how much she was spending on little things. They really add up.
  • When Kiera started making her own lunches and eating better, she became attuned to things that were going on in her body. She was diagnosed with polycystic ovarian syndrome (PCOS), which is an estrogen imbalance, in her mid-20s. It had been explained to her that she needed to be on birth control.
  • Kiera started realizing that she felt good the first two weeks of the month and bad the last two weeks. She started taking the DIM supplement and using a progesterone cream and it made a big difference. 
  • Her health started changing and she looked forward to things her insurance would cover like teeth cleaning. Her mindset changed and she stopped to think before she would go get a cup of coffee.
  • Sometimes what she really needed was to walk or talk to a friend. Before, Kiera would use her coffee break to avoid something stressful and she actually just needed to ask someone for help.
  • Kiera loves going to coffee shops, but she rarely buys her coffee out anymore. Before, the little ways she spent her money was the only good feeling she had in a day. 
  • The accountability of having a Financial Trainer is helpful for Kiera.
  • For the Gym, a great session is the client showing up. Coming in and facing your finances is the hardest part. Trainers just want you to show up. They want the best for you.
  • Kiera’s sacred cow is beauty products, because it is important for her self care. She has her own podcast called Beauty Therapy.
  • Through listening to other podcasts, Kiera found human design.
  • While she was driving, she heard it and she found out it is related to what time of day you are born. She knew the time she was born, so she pulled over and found out she is a manifesting generator. This type is meant to move through the world in a non-linear path, take on many different jobs and roles, and their work is all about being able to dive into what their heart is called toward. 
  • The chart was very complicated to read, so she went to book with a reader and she wasn’t available for seven months. She booked it anyway and in the meantime, she bought a ton of books on Amazon to learn about it.
  • Human Design is like an astrology chart on crack. It is like a manual or guidebook on how to navigate throughout the world. There are five different energy types and from there you will find out your strategy. Are you meant to respond to the universe, are you meant to initiate and get things done, are you meant to wait for the invitation, etc. You will then find the special skills and talents you have and how you make decisions.
  • Inside all of our charts, we have an energy system which is either defined or open. Where we are open is where we drink in and take in the world. Where we are defined is our personality and that won’t change.
  • Kiera finally had the session and she was excited because everything the chart reader told her, Kiera already knew. As soon as she figured out how to read her chart, she wanted to read for her friends and family.
  • By following her design, it was the first time in four years she decided to be uninhibited and go where her heart was calling her. She started reading charts and started a podcast while working a full-time job.
  • Kiera started reading for her friends and people she worked with, about five or six people, and then she started getting inquiries from people she didn’t know.
  • Kiera connected with a woman in Saudi Arabia who is an influencer on Instagram, and she has sent her at least 100 clients from Saudi Arabia. Kiera is breaking into the New York market and she has done three events on Human Design.
  • The abundance that comes from reading has been transformative. 
  • The five energy types are:
    • Manifestor: The people who wrote the book The Secret. They use the phrase “I think, therefore I am”, “I knew it, so it came true”. All they need to do is think and they can initiate it or manifest it and bring it to life. They have a powerful aura, but it can be repelling, because it is meant to protect them. These are the guys that were the emperors, pharaohs, kings and they needed something where people weren’t going to attack them. What manifestors want most now is to simply be able to manifest in peace. Their strategy is to inform other people what they are going to manifest before it comes through. These people are pretty rare and make up about six percent of the population.
    • Pure Generators: They have the energy and life force that is defined and they produce energy. They have to do work they need to do or they will feel burned out. With the right work, they will have more energy. They have to be in the game and contributing.
    • Manifesting Generators: This is a hybrid of manifestors and generators. They came here to work and they have to do what they love. They are always distracted by the next shiny thing. They are here to teach the world they don’t need to move on a linear path and they are here to have fun. They are light and playful. Collectively, the generator types make up 70 percent of the population.
    • Projectors: They are around 27 percent of the population and they don’t have an energy center, so they can’t create energy for the world. They borrow and transmute from other people. They are here to be our guides and our leaders and they can’t work all day. They are meant to have a 30,000 feet in the air perspective and tell others where they should go to get things done. They want to be seen, because they see others so well.
    • Reflectors: They are rare and make up less than one percent of the population. Their entire body graph is wide open. They drink in the world, they take in everything, and they reflect back to everyone else. They want to be surprised. They need to wait a full lunar cycle to make a decision.
  • Shannon was born April 19, 1978, at 10:20 am, in New Orleans. Kiera uses a website called JovianArchive.com.
  • Shannon is a pure generator and her number one responsibility is to stay lit up. She has the energy to bring up everyone else’s energy in the room when she is feeling great and she can also bring the energy down. 
  • When she does the work she loves, she is energetic and she can keep going with that work. When she is feeling bogged down and not fulfilled, she is drained physically, mentally, and emotionally. She is defined in her Sacral and her root center.
  • Shannon has a lot of energy to get things going, get things started, and get things moving and she has a lot of openness. She is able to channel information and ideas. It is good for her to be around other people for brainstorming. 
  • Shannon is open emotionally and she tends to pick up other peoples’ emotions and she feels those emotions three times more than the other people.
  • According to the charts, the two things she tends to avoid are confrontation and truth, because she doesn’t want to hurt the other person. She over anticipates in her mind that the other person is going to be so upset or so mad, so she avoids it and just deals with it.
  • Shannon has the intuition psychic gate. 
  • It takes the average person seven years to decondition when they learn their energy type. When we can live according to our authoritative design, that is when we are able to get into our flow.
  • Shannon is already living according to her design. Her gut is her authority.
  • When we can live according to our design and listen to that authoritative center within us that’s when we are able to get in flow.
  • So many of us live in our heads. It doesn’t matter which energy center you are, your head center is never going to be your authority. Every time we try to make decisions with our minds, we are making the wrong decision. 
  • Shannon is great at selling ideas. When she speaks, people really trust her. It comes through on a soul level. Human Design takes in to consideration your soul’s birthday on your birthday. They are two charts merged together, and our soul’s birthday is 88 days before we are born.
  • Shannon’s profile is a 4/6, which is a opportunist/role model. As an opportunist, the world sees you first as someone who is vivacious, sparkly, connects with a lot of people, and very good in PR. The community you build around you is going to change your life and lead you down different paths and directions.
  • As a role model, Shannon’s life is meant to be lived out in three phases.
    • The first phase is 0-30 years old, which is the trial and error phase. This is the time where you feel like you need to be at the center of everything. During this time you bring up a lot of pain for yourself and a lot of inner trauma. This ends after Saturn returns. 
    • In phase two, you move on to what is called the roof of your life. This is the time you sit on the roof and realize you don’t need to be a part of everything in order to learn from it. Now you are going to learn from other people and your perspective shifts outward. It is about noticing for the first time where other people are. This is the time to take on a new study or new practice and go internal with building and creating this new thing. This phase will last as long as it needs to or until around 50 years old.
    • The third phase is called the role model. This is a person that takes on as a public figure. It is somebody who has lived through it and made the mistakes and it is somebody who has really learned how to clean up that mess and help the community. You’ve brushed up against life in a hard way and you have fallen back in love with life. You are the person everybody looks to for answers.
  • Shannon wanted Kiera on the show is because of the transformative nature of getting financially healthy. Her path to financial health led Kiera to this awakening and to a new and better understanding of herself. There is so much power in getting financially healthy. 
  • Shannon has been more and more interested in human design, because it started with Oprah’s SuperSoul Conversation and about finding herself. A lot of these things are intertwined.
  • Knowing yourself, why you are here, and your purpose in life takes away a lot of unhappiness.
  • Human Design made Kiera feel like she has permission to be herself. It is all about unbecoming everything we are not so we can step into who we really are.
  • Click here to schedule reading with Kiera, and enter promo code GYM150 for $45 off.

TAKEAWAY: My biggest takeaway is that life is unpredictable, although according to Kiera it can become more predictable with Human Design. The best way to manage the unpredictability is a focus on financial wellness. You truly have no idea where the journey will take you, but it always seems to be such a great road trip.

Random Three Questions

  1. What is a movie you can watch over and over again?
  2. If this was your last night on earth, what would be your last meal?
  3. If you had one million dollars, what would you do with it?

Connect with Kiera 

Podcast: Beauty Therapy

Instagram: @kierawithlove

If you’d like to talk to my team at the Financial Gym to help you get started, or pick you back up onto your financial wellness journey, I hope you’ll reach out to us at the Financial Gym. We have truly seen it all at the Gym and my trainers can’t wait to help you achieve the financial success you want. The great news is that Martinis and Your Money listeners get 15% off Financial Gym services. So head over to, or send friends to, financialgym.com to get signed up today.

Debt Settlement with Leslie Tayne

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Debt Settlement with Leslie Tayne

At the Financial Gym, clients of all financial shapes and sizes come to us to work on the areas of their finances they would like to tone up. Some want to get more education on investing, some want to learn more about budgeting, some want to figure out their student loans, and many want to understand the options they have to resolve the debt that they’ve accumulated.

Resolving debts is exactly the specialty of today’s guest, Leslie H. Tayne, author, attorney and award winning founder and director of the Tayne Law Group. Leslie joins me today to answer debt resolution questions from bankruptcy, to debt settlement companies, and everything in between. If you or someone you know is wondering about fixing up your debts, this is a conversation you will not want to miss.

What Are We Drinking?

Leslie — Special Martini (Titos with muddled mint and a splash of pineapple juice)

Shannon — Caramel Vodka Martini (Smirnoff Kissed Caramel Vodka over ice)

Podcast Notes

  • Leslie is from Long Island, which is an Island off New York, and it’s where Shannon grew up. Shannon has fond memories of the island. It is not tropical, it is just a suburb of New York.
  • Leslie has been an attorney for over 20 years and it was her destiny. There wasn’t any other option for her. However, she could never have imagined where she would be today and the work that she has done.
  • When she went to law school, she thought she was going to go more into public law, because she had a lot of interest in it.
  • She graduated with student loan debt, not from college but from law school. Leslie took out $65,000 for law school, where today it is difficult to get out of law school with less than $100,000 in loans. 
  • When she was just starting out her law career, Leslie was married and had a baby, and she wasn’t making very much money.
  • She thought her ex-husband was taking care of the payments for her student loans, but he wasn’t and the loans went into default.
  • Leslie got divorced when her twins were five years old and her oldest child was seven. From that point on, she focused on building a practice, which helps people with debt and financial issues. 
  • One day, Leslie’s accountant told her she had enough money to pay off her student loans. She felt like she won the lottery, because she thought she would be paying for the debt forever.
  • A lot of this is in her book, Life and Debt: A Fresh Approach to Achieving Financial Wellness.
  • She found out that her loans were in default, because she received letters, phone calls, and she was sued by a private student loan servicer. 
  • The federal loans were being paid off or they were in deferment, but the private student loans didn’t offer anything, except for her to make impossible payments. She was able to negotiate those and pay them off.
  •  The federal student loans were $923.31 per month. It was a lot of money and a lot of stress, but eventually her credit score started to rise.
  • When you are young, you are not supposed to have any money and it is not uncommon to be in debt. This perspective makes all the difference when you are looking at your financial circumstances and when you are trying not to be too hard on yourself for having the debt.
  • This debt is a reality for 65 percent of the population and it shouldn’t define you. There is so much shame around this debt, but it is nearly impossible to get through college without it.
  • The education system has flaws, but it is supply and demand – there is a tremendous demand to go to certain schools. When you are young, it is normal to be paying down debt. It is all about how you look at it.
  • Leslie knew it was going to take time to pay her loans off. It hindered her ability to travel, save for retirement, etc., but it gave her a career, a life, an income, and a future. She doesn’t look at it like the worst thing that happened to her.
  • Leslie currently has five children in college, three of her own and two of her husband’s. You have to make smart decisions as you are going through the process, because you will need to deal with it in the future. To say it is everybody’s fault that you got into this debt is a very negative thought process. Think about it in a positive way, that it is giving you huge future and opportunities and there is a cost, there is a cost in any investment. You need to pay something to get something out of it.
  • Leslie doesn’t regret paying double for her student loan, because she is thankful for her life now. She is in a position where she can pay for her children’s education.
  • When Leslie went to law school, the only thing that existed was bankruptcy attorneys. You cannot set a focus when you are in law school, there is a set of classes you must take in order to take the bar exam. As you do internships and work in different places, those are opportunities. 
  • Leslie had a baby and was working in a position she didn’t love. She wanted to spend more time with her daughter, so she took a part-time, in-house counsel position that turned very quickly in to a full-time position with a tremendous amount of hours and commitment for a national debt settlement company. This opened the door for her to do this on her own.
  • She felt like this service was missing in the industry. There are so many legalities involved in resolving basic debt and there is a real need for that. She was able to focus on her mission and her goals, which was to provide a service that was non-existent and had trust as the underlying foundation, and to build a reputation of reliability and success with other colleagues who regularly send her clients. 
  • Debt consolidation companies are good, and debt settlement is really good because it works. What doesn’t work is unscrupulous companies and individuals that take advantage of consumers. It creates an opportunity for the press and the Attorney General to step in and say you cannot take advantage of people. 
  • When you are going through a difficult financial time, your mind is totally twisted. You are emotionally distraught, you are probably fighting with your significant other, you don’t know what you are going to do to rob Peter to pay Paul. When these companies have a solution to save the day, the problem is when they don’t tell you the middle part, they disappear, or they charge a fee upfront.
  • When Leslie first became an attorney, there were no laws or regulations related to debt settlement or debt consolidation, but this has now changed.
  • Leslie’s law practice concentrates mostly on debt consolidation. It is a broad term that encompasses debt repayment, debt settlement, and debt restructuring. It works really well when you have the right people who understand your personal financial circumstances and know that you need more than a one-size-fits-all solution.
  • If something happens in the meantime, like a loss of a job, tax issues, other financial issues, etc., you won’t be left out there to fend for yourself. 
  • Debt consolidation generally means you are looking at consolidating all of your debt into one loan, so you pay one creditor for one loan. This generally doesn’t work because it doesn’t resolve the underlying issue, which is cash flow. If the payment is similar, you are going to end up with more credit card debt. When you are still paying interest, you still won’t be able to pay it off in a few years. 
  • Although she is licensed for it, Leslie doesn’t practice bankruptcy in her office. If you can’t put food on the table, you are a bankruptcy candidate. If you have cash flow, an income, the ability to make a payment, and sit with someone who can look at your finances and your budget and how you can reduce the debt that is causing the problem, bankruptcy is not necessary.
  • There are three types of bankruptcy: 7, 11, and 13.
  • You have to qualify with your income, debt, and assets, including your home. Bankruptcies stay on your credit report for 10 years and you need to disclose them to your insurance companies, potential employers, and other applications, which increases every single interest rate that you have. 
  • If you can find another viable option to avoid bankruptcy, Leslie is all for it. However, there are times when bankruptcy makes sense. A seasoned individual who has your best interest in mind will take a look at your situation and tell you why the option of bankruptcy makes sense or doesn’t make sense and give you alternatives to consider. 
  • There are many bankruptcy attorneys that advertise under debt settlement or consolidation, but they are really bankruptcy firms. Make sure you see someone who is not primarily a bankruptcy attorney and offers other alternatives. 
  • If you can avoid filing bankruptcy, avoid it. 
  • There is no incentive for any creditor to resolve your debt, if you are making current, on-time payments. Reducing the interest isn’t going to solve the problem.
  • If you are behind on your debts, it is a lot to manage those creditors that bombard you with phone calls. Leslie can control it, because she knows when each creditor will be willing to resolve your account, by how much, and at what terms, based on your financial circumstances, but you as an individual don’t know that. They will tell you all kinds of things that are inaccurate, and Leslie knows what those things are.  
  • In 2009, you could offer pennies on the dollar to resolve debt. Now, creditors can use creditor friendly laws that allow them options to come after you. There are a lot of nuances.
  • Certain creditors will not resolve debt below 75 percent, even if you have stage four cancer. Some creditors don’t care and will allow the debt to die with you.
  • Creditors have been burned so many times by debtors who say things that are false or don’t follow through, and they really take what a debtor has to say as true and accurate. They aren’t going to give you the benefit of the doubt and work with you to get numbers that are low. 
  • Leslie does this everyday and she has relationships with these creditors. Whatever resolution happens, it will be a legal agreement.
  • You can’t go in with demands to your creditor and think that you are going to get your way and it will all be great. There is a realistic perspective to take and Leslie tries to manage those expectations early on. If you try to do it on your own, it is like changing the oil in your car. We are all smart and capable, but the oil may fall on your face and it will be messy and dirty and you might make a mistake. It might not come out the way you expect. 
  • It is a full time job. There are some creditors Leslie will sit on hold with for two hours, even when they have contacts there. Creditors make mistakes and Leslie’s firm has to go back to make sure they correct them. It is a lot of work. People don’t always see the work that goes into this.
  • Leslie has clients all over the country. She has been doing this a long time and she has a law degree. You need an in-state attorney if you are being sued, but you can use an attorney in another state for general resolution of accounts. Her firm has partnerships with attorneys if clients need to go to court in other states.  
  • Even if a company is non-profit, it doesn’t mean the people who run the company don’t make an income and drive fancy cars. Not for profit is a tax status and, at the end of the day, they can’t earn a profit, so they pay salaries and expenses. It doesn’t always mean they are out for your best interest. 
  • If you find a non-profit company that has a good reputation and they have been in the industry for a long time, it might be an organization worth pursuing. 
  • You need to define your goals and objectives on what you want to achieve first. Define the problem. Once you figure that out, then you can find the appropriate solution. Don’t only look at what you get in the mail, hear on the radio, or see on TV, because it doesn’t necessarily translate into a company that is looking out for your best interest and meets your goals and objectives. Ask them questions.
  • The majority of debt settlement companies out there take a percentage of your payment for their fees and they take their fees up front. That is illegal.
  • Sometimes if you are making payments to the debt settlement company, they may not make the payment to the creditor. That increases your risk of getting sued by your creditor. 
  • Be very selective of who you work with on your finances. Resolving debt is a business, and it is very profitable. With larger companies, whoever you speak to is not resolving your debt, the settlement piece is outsourced, and you never speak to the same person twice. Leslie fixes a lot of the problems from people who come from these places.
  • Her practice does not take in people who don’t have a willingness to resolve their debt and a willingness to be good listeners. It is a partnership and a relationship that they have for three to five years and it will impact their entire life. 
  • Understand that when you are facing a financial hardship or you are struggling a little bit, the decision to take control of that and move forward so you can have a different kind of future, there are ramifications, but they are worth it. 
  • Sometimes this is the best thing that can happen to you, because it really changes your thought process and can inspire you to do things very differently that can put you in a different place.
  • As an adult, the likelihood is that you are going to have a financial hurdle you need to get over and it is all about finding the right people who understand you and can make it happen for you.
  • It’s not about what you did, it is about making the decision to help yourself. Don’t be ashamed that you have debt. 
  • People might look beautiful on social media, but their bank account may be ugly.
  • Debt happens. It doesn’t discriminate. Where you can change the game is dealing with it. 

TAKEAWAY: My biggest takeaway is that debt resolution is not an overnight process. It’s quick to get into debt, but frequently takes months or years to get out of it, so make sure that you find a path and solution that feels best to you with people that you trust to help you along the way.

Random Three Questions

  1. What is a show you like to binge watch?
  2. Do you travel, and, if so, what is your favorite vacation?
  3. If this was your last night on earth, what is your last meal?

Connect with Leslie

Website: www.taynelaw.com

Phone: 866-890-7337

Twitter:@lesliehtayneesq

LinkedIn: Leslie Tayne

Twitter/Facebook/Instagram: @taynelawgroup

If you’d like to talk to my team at the Financial Gym to help you work through any of your financial challenges, including debt, I hope you’ll reach out to us at the Financial Gym. We have truly seen it all at the Gym and my trainers can’t wait to help you achieve the financial success you’d like to achieve. The great news is that Martinis and Your Money listeners get 15% off Financial Gym services. So head over to, or send friends to, financialgym.com to get signed up today.

Pros and Cons of Working Nine-to-Five with the Happy Hour Ladies

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Pros and Cons of Working Nine-to-Five with the Happy Hour Ladies

Today is the last Friday of the month and my regular listeners know that on the last Friday of the month, I host a happy hour on the podcast where I gather great friends with me to drink cheap drinks and talk about money topics.

This month on the podcast, I’ve had a theme of entrepreneurship, and we are continuing that theme to happy hour. All of the happy hour ladies have worked traditional nine-to-five jobs and started their own businesses. Today we discuss, as we discuss all things, honestly the pros and cons of both career choices and whether or not we could go back to a nine-to-five job after being entrepreneurs.

What are we drinking?

Melanie from Dear Debt and Lola Retreat — Vodka Martini

Tonya from Budget and the Beach and Tonya-Stumphauzer.com — Sierra Nevada Pale Ale

Liz, Mrs. Frugalwoods, from Frugalwoods.com — On Vacation

Shannon —  Boxed Rosé

Podcast Notes

  • Tonya worked a nine-to-five job up to 2008. Her goal was to always have full-time work. After that, she was a freelancer until December 2015 and then went back to a nine-to-five job until June 2018. She has been freelancing ever since.
  • Tonya graduated from college in 1992 and her first job out of college was at Ford Motor Company. She was paid terribly and had no benefits.
  • Tonya quit her job to move from Detroit to Seattle. She temped for about nine months before getting a full-time job at Northwest Cable News. It was really easy to find work back then. The majority of her work life to that point was working nine-to-five.
  • Melanie graduated college in December 2006 and worked nine-to-five from 2007 to 2010, in the non-profit sector, at an after-school program, as an arts director. Then she went to grad school from 2010 to 2011 and was working three part-time jobs.
  • From 2012 to 2014, Melanie was working side hustles here, there, and everywhere. Her last full-time job was from 2013 to 2014, which was an events and communications coordinator at a non-profit, making $31,000. Melanie quit that job in 2014, even though she had $40,000 in debt, because she was convinced she could make more. She was right – she doubled her income right away, to $60,000, and she paid off her debt in 2015.
  • Self employment isn’t for everyone, but for those who are stuck in the low-pay trap of non-profits, it can be really helpful. Melanie threw a five-year self-employment party a couple of months ago. This is her longest job.
  • Shannon graduated college in 2000, and her first job was at Bank of America, then a hedge fund, then Bank of America, then Merrill Lynch. In 2013, she had her “aha” of the Financial Gym. There are different growth points for the Gym. She got her first investor in 2015 and her larger investors in 2017. She has been at this for seven years.
  • Shannon had different jobs in that 13 year span, trying to find “the thing”. Toward the end, she had three different jobs in three years, and then she told Bill she wanted to start the Gym.
  • Shannon and Melanie opted to leave the nine-to-five for something else. Tonya didn’t have a choice in 2008. She was working for Vivendi Games as a senior video editor and producer and she had been there for eight and a half years. She probably would have stayed there forever because she was making decent money and she liked her boss.  Her company was bought out by Activision and her department tried to convince them to keep them as a video department, but they didn’t, so the company dissolved and she was let go.
  • Tonya was always interested in being a life coach, and that was in the back of her mind, but she didn’t have any experience and she didn’t know what to do.
  • She had an amazing severance package of six months pay and full benefits for that time, plus she saved her vacation and she had a big chunk of money.
  • The first week, someone who was brought on to help at Vivendi had a huge project waiting for her, like $18,000, for two to three weeks of work. Freelancing was great!
  • However, it was like a tease. She did not have jobs like that all of the time, and it got progressively worse. Tonya didn’t know what she was doing, and she was spending a lot of money. It was the perfect storm.
  • Entrepreneurship is not for the faint of heart. It is a rollercoaster.
  • Even though there are so many challenges, Tonya is not ready to go back to a nine-to-five job.
  • A huge con of going out on your own is the ask. There is a lot of time spent being uncomfortable and asking for the business you need to feed yourself, but you have to ask. If you are someone who struggles with that and can’t push through the pain of it, just know that it never stops.
  • No matter how much you want to be given business and have things thrown at you, Shannon does not know of anyone who started a business and has constant work thrown at them. It takes a while to get to that point. About 99 percent of the time, you need to ask for what you get. It doesn’t matter who you are, it is uncomfortable.
  • Melanie takes rejection personally, because she is the business.
  • Shannon has raised $7.5 million to date for the Gym, and she still struggles with the email she sends out asking for money. She needs to ask, because she needs to pay herself, her employees, and her contractors.
  • If you are a nine-to-fiver, really appreciate how nice it is that you are just given money every two weeks and they are paying the government for you. Be grateful for that.
  • Tonya recently had to cancel a trip Hawaii, because she needs to work.
  • A pro of a nine-to-five job, is that it is not your problem. At the end of the day, your employer isn’t going to go out of business if you wait to reply to an email. If you are on your own, it is always your problem. You are all of it.
  • This podcast was recorded on Labor Day, because Shannon, Tonya, and Melanie were all working.
  • Melanie’s number one pro for being on her own is the flexibility. Everyone knows that working nine-to-five is not a great schedule. No one’s natural energy is sustained from nine to five. Melanie is a night owl and she doesn’t like working in the morning. She usually doesn’t start working until 11:00 am or 12:00 pm, she takes a nap in the afternoon, and sometimes she takes Mondays off to visit her grandpa.
  • Having the flexibility to do that is so much better. She likes going to the grocery store on a Tuesday or a movie during the week. Melanie doesn’t like having to watch the clock and she can have a drink at lunch.
  • Tonya agrees with this as well as no more office politics.
  • As the Gym has grown, Shannon has had less flexibility. She is still the boss, but she has so many people she answers to, like clients, employees, and investors. When it was just her for four years, she got into a rhythm.
  • A pro of being a freelancer is the flexibility, but if you aren’t careful, you could end up working seven days a week.
  • Blogging was a big part of Shannon’s world when she had time on her hands. A lot of blogging happens Monday, Tuesday, and Wednesday. Friday ended up being her Saturday, because on Saturday and Sunday she would write blog posts for the next week.
  • Every other Friday is held for Shannon’s free day. She wants it to be a Saturday for her, but lately her free days have been blocked.
  • In the beginning, almost every Friday Shannon and her mom would go out for drunch (drinking lunch). Now that free day doesn’t happen as much.
  • Melanie misses health insurance the most. She spends $358 per month on the cheapest, most crappiest insurance. It is confusing and hard. The taxes, retirement, and health insurance are the worst. She misses having sick time and vacation time.
  • Vacation time it isn’t only time you need off work to decompress, it is also time that you aren’t making money.
  • Right now, Tonya isn’t making anywhere near what she was making as a full-time employee. The constant adjusting and time tracking is difficult. She needs to make sure she is staying focused and assess if the jobs she does are working for her.
  • Shannon misses things being someone else’s problem. When the computer doesn’t work, it is IT’s problem, or if she has an issue with health insurance, it is HR’s problem. Even when it is just you, everything is your problem.
  • When Shannon was on her own, her website was hacked. She had to figure out how to fix it. You have to do everything. As her team grows, she is getting better at delegating.
  • Another pro of being on her own is that Melanie likes being able to execute a vision of what she wants her life to look like and what she wants her schedule to look like. Lola Retreat is difficult to produce but very rewarding to see it come to life.
  • A pro for nine-to-five is having people around you who could be a mentor for you.
  • As much as office politics suck, it is nice to have someone who is going through what you are going through.
  • Tonya wonders if it is worth it to pay for a business coach. It feels like you are on an island by yourself. Even though you have fellow freelancers around you, it would be helpful to have someone help you hone your vision into the right avenues. There is so much experimentation and it might not work.
  • The highs are really high. If Tonya is helping someone with their company, and she is making a bigger difference than if she was working for another company.
  • Shannon was uncomfortable being in the box (working for someone else) when she saw her co-workers who had been at the company for 25 years lose their jobs in 2008.
  • There is nothing better than having a direct result to your actions.
  • Melanie doesn’t see anything that would coax her back to a nine-to-five job. It would have to be a really great job, but she doesn’t know what that would look like.
  • Tonya cannot imagine a job that would get her back to nine-to-five.
  • Shannon doesn’t know if she could work for someone else again. She has been the boss of other people for three years now. She has been the problem solver and the implementer.
  • Shannon is hiring 25 new people. The Gym is going from 24 employees to 49 employees.
  • Shannon was recently featured in Shape Magazine, in an article called How Shannon McLay is Bringing Financial Fitness to all Women.
  • On October 6, Shape is doing an all-day event in NYC. Shannon will be on a panel called Change Makers: Women who are proactively addressing an issue to affect change.
  • If you are thinking of taking the leap into freelancing, Tonya recommends having as much money saved as possible. It will be that much less stress.
  • Melanie says to learn as much as possible in those first couple of years and build relationships and your reputation. Once you have a network, you have some leeway to be a human being and not freak out when things happen.
  • Shannon recommends playing nice on the playground. Always be the better person, because you never know when that will come through.
  • If you want to start something, have at least one year of expenses saved up and be really passionate about what you choose to do. You are going to work a lot of hours and, if it feels like work, it is going to be really challenging.
  • Shannon is passionate and motivated by the work and the thing she is building and it sustains her through the rollercoaster and long hours.

TAKEAWAY: My biggest takeaway is that the entrepreneurial journey is truly not for everyone. If you have a strong stomach and a willingness to hustle, despite the ups and downs, you may actually find out, like I did, that it is the only way you could ever work again.

If you want to work with my team at the Financial Gym and find out what it takes to start a business, remember that Martinis and Your Money Listeners get 15% off Financial Gym services. My financial trainers have seen it all. No matter where you’re starting, we have the tools and resources to get you where you want to go. So head over to, or send friends to, financialgym.com.

If you have any topics you would like for us to talk about during happy hour, please feel free to email me at shannon@fingyms.com or tweet to me at blonde_finance or join the private martinis and your money Facebook group and let us know. Until next time, take care!!

Becoming an Entrepreneur with Hitha Palepu

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Becoming an Entrepreneur with Hitha Palepu

Continuing my entrepreneurs theme of the month, today I’m introducing you to an entrepreneur who is my woman crush in every way imaginable. You’ll hear more about why later in the show, but I can’t think of a better woman to round out this month than Hitha Palepu, Entrepreneur, Angel Investor, Author and Consummate Multi-hyphenate as she says. Hitha joins me today to share her personal entrepreneur journey through three businesses and why she loves investing in other founders.

As a side note, I’m apologizing in advance for my sound quality. We recorded the entire episode only to find out my mic wasn’t captured. So for my sound snobs, I apologize in advance. The good news is that Hitha does most of the talking and she sounds great!

What Are We Drinking?

Hitha — Water and Coffee

Shannon —  Black Cherry Schweppes

Podcast Notes

  • Hitha’s entrepreneurial journey was very winding, as most are.
  • Right out of college, she joined Cisco Systems in their sales associates program. Her first accounts were some of the biggest, global pharmaceutical companies in the world.
  • She graduated with a degree in biochemistry and history. Her dad has worked in pharma his entire career and she knew it was just a matter of time before she joined the industry too, she just didn’t know how.
  • Cisco was an incredible training ground. It gave her the discipline and cultivated her hustle. Natural born sales leaders need that little bit of training, that little bit of coaching to convert that hustle into productive hustle and Cisco was amazing for that. 
  • By the end of her three years there, Hitha was tired of selling technology solutions and she wanted to be in the industry developing the drugs themselves. 
  • At that point, her father’s company, which was just him and his co-founder Joe, was growing. They had a product hit the market and they were generating significant revenue and were ready to grow the team and operations.
  • Hitha was the first non-founding employee and she did everything that her father and Joe didn’t do. This was everything from getting caught up on the programs they were developing, learning about pharmaceutical development for the first time in a really technical and detailed way, booking travel and hotels, and doing whatever she needed to do.
  • Hitha works really well with her father and they are on their second company now. He has always been a mentor to her and he always took the time to explain what he was doing in a calm, productive manner. When she misbehaved as a kid, her punishment was to write a report on ten related medical words. 
  • Hitha’s mom had the same hustle and she was in a million different job roles when Hitha was growing up, from being a small business owner to project manager at a telecom company to working in retail. She is not someone who sits still.
  • Seeing her work so hard for the joy of working really inspired Hitha to see working as fun, and she couldn’t wait to work and do different things. 
  • Hitha knew she could take a risk and try something new, as long as she had a good plan around it.
  • Women who work teach their kids different lessons. It is not a bad thing. 
  • When you are talking to your child and you flip it to say “you get to go to school” and “I get to go to work”, it shifts everything and makes us more grateful, allowing us to throw ourselves into what we are doing with more gusto and passion, and it is a way to rev yourself up when you are feeling low. 
  • All of the products that were developed at her father’s business will be earning royalties for a long time, so it is now a holding company for future earnings, but is no longer operational. 
  • Hitha started a philanthropy tech startup after that, because she needed a break from pharma and things taking years to develop and get traction.
  • It was not a successful exit and they ended up shutting down the business. They didn’t establish product market fit and they didn’t have a clear communication strategy. There are so many things she could have done differently, but she is grateful for that experience, because it taught her to be a leader, it taught her what it is like to fundraise, and it taught her what she needs to establish early on.
  • She would not be as successful of a CEO with Rhoshan Pharmaceuticals without that experience. 
  • Hitha couldn’t do anything else but invest, advise, and write. There is no going back to another company, working in and building a company, that wasn’t her own.
  • Her dad was tinkering around with an injectable presentation of one of the most common drugs in the world and no one has been able to develop an injectable for it. Her dad lives with her half the time and they talk about work a lot. He said he figured out the formulation and she asked him about patents. He went and got the patent and she asked him what the FDA said. At that point he gave her a giant piece of equity of the new company and let her decide what she wanted to do.
  • At that point she had just launched her book, she wound down her company, and she was thinking about what her next step would be. The idea of jumping back in and bringing this product to approval with her father excited and challenged her. They would be running the company together, not her working for him and a partner. 
  • They assembled a wonderful team of individuals who have done their jobs longer than Hitha has been alive. 
  • Hitha is close with her parents and she is lucky to have the relationship she has with them. To spend this kind of time with her father is really special and she doesn’t take it for granted.
  • With pharmaceuticals, there is a long lead time before you know if you have a viable product. Because they were working with an existing drug, it took from 2016 to now to scale it up to half of what a full production will be. They did the clinical trial last year and they have some tweaking to do before the next one. It is a lot of work and is very expensive. 
  • They need to manage cash flow and raise capital. They will be lucky if they get the product approved by the FDA with $25 million in total capital raised. 
  • With most drugs, when you are developing the drug substance as well as the formulation, it could cost up to $1 billion to develop, and this changes your valuation. 
  • You can make your numbers work any way you want, but if you can’t defend it to a potential investor, what’s the point? There is a constant retooling of their model, of their commercial strategy, of what is going on with the manufacturer and Hitha is constantly updating certain documents every single day. 
  • You could potentially need to say that you have a $300 million company with no product. It is not an easy sell.
  • A few years back, Hitha started angel investing.  
  • Hitha was one of M.M.LaFleur’s very first customers. They launched in a PureWow newsletter and at the time, Hitha was working for her dad’s first company, traveling almost every single week in very conservative environments, but she didn’t want to sacrifice her style. 
  • She would wear Ann Taylor and J. Crew, but she had to dig to find pieces that would be appropriate that she liked, that were comfortable, and that she wasn’t tugging on hem lines and necklines to make them appropriate
  • M.M.LaFleur spoke to her immediately and she put in an order the second she got the email. She still has some of the dresses from her first order.
  • She sent them an email explaining how happy she was about their business and asked to meet them. She wanted to work with them. She became friends with their founder and CEO. 
  • She had been one of their first ambassadors, she featured them on her blog, and they did some events together. After a couple of years went by, Hitha and the CEO were talking about how they approach negotiations and Hitha found out M.M.LaFleur was raising their first round of capital. 
  • Hitha loved the company so much that she wanted to invest. It was a lightbulb moment for her. She wanted to help further the M.M. mission. She and her husband got the green light from their money manager and they invested. 
  • From that point on, Hitha took a much keener interest in her and her husband’s personal finances, how they were budgeting and saving, because she wanted to do more investing. 
  • To be an accredited investor, you need to have either over $1 million in assets or make over $250,000 a year in income for more than two years in a row. You also need to have the cash to invest. 
  • If you are going to do this as part of your investment portfolio, Shannon says, from a financial planning standpoint, you shouldn’t have any more than five percent of your investable assets in one particular holding, but that is a decision you need to make. 
  • You have to be willing to never see that money again, because 90 percent of startups fail. 
  • Hitha and her husband have made about 13 angel investments to date. All of them are still active and 12 of them have female founders.  The one male founder started a company that will disproportionately benefit women.
  • They do review male founded deals and she has passed on every single one, because the standard they hold their founders to is very high. This is especially true when it comes to communications, community, and marketing.
  • Hitha prefers quality and value. To her, 100 “sticky” clients is always going to make more sense than 1,000 sign ups.  
  • If you want to start a business, know that you are going to work harder than you ever will. You have to have a growth mindset where everything is a learning opportunity, you have to roll with the punches, and you need to look at the big picture when something goes wrong and work with your team to chart a path forward. You need to be an aggressive communicator, have relentless follow up, ask for help, and you need to be ready for anything. 
  • You need to be coachable. You will get a lot of advice, and you need to be able to filter the good from the bad.
  • If you want to be an angel investor, work really hard to qualify for investor status. You are not going to be a successful angel investor until you have the financial security to be willing to write a $10,000 or $25,000 check and say I’ll be okay if I never see this again. You also have to be really quick to make a decision, because you won’t have a lot of time when the opportunity arises.
  • Figure out what is important to you. When you write a check to a company that is serving a much larger mission, you need to be connected to that mission. Be a support and a cheerleading squad for the companies you are investing in.

TAKEAWAY: My biggest takeaway is that if you want to become an entrepreneur, the growth mindset and aggressive communication skills are truly two keys to success. If you can’t identify with these, the entrepreneurial rollercoaster may not be the one for you.

Random Three Questions

  1. What is your favorite book?
  2. What is a food you hated as a kid and do you like it as an adult?
  3. What do you do to relax?

Connect with Hitha 

Instagram: @hithapalepu

LinkedIn (in the bio): Hitha Palepu 

Website: (Coming Soon!) Five Smart Reads

If you’d like to talk to my team at the Financial Gym to help you prepare, at least financially, to start a business or help run yours better, I hope you’ll reach out to us at the Financial Gym. The number one employer at the Gym is “self employed”, so it’s certainly an area we’re comfortable working in. The great news is that Martinis and Your Money listeners get 15% off Financial Gym services. So head over to, or send friends to, financialgym.com to get signed up today.

Date Brazen with Lily Womble

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Date Brazen with Lily Womble

As many of you know, my primary job is not recording this podcast, it’s running my company, the Financial Gym. I don’t have as much time as I would like to be thoughtful about my podcast scheduling, so you can imagine how excited I was to realize that when I looked back on a number of the podcasts I recorded, I saw a theme of entrepreneurship.

The month of September has officially become entrepreneurs month here on the podcast, and today I’m featuring Lily Womble, founder of Date Brazen. Lily spent years as a successful matchmaker only to realize that most of the dating work had to begin way before the matching could take place. She joins me to share her entrepreneurial journey and how we can all have more fulfilling and meaningful dating lives.

What Are We Drinking?

Lily — Black Cherry Schweppes with Vodka

Shannon —  Grapefruit Schweppes with Vodka

Podcast Notes

  • Lily is from Birmingham, Alabama, she lived in San Francisco, and now lives in New York City. 
  • Shannon met Lily at an event at the Financial Gym. After that, Lily became a fixture in the Gym.
  • Lily is a dating coach, but started her career in matchmaking. She moved to New York on a whim.
  • She had a stable job at a non-profit in San Francisco. She studied international relations in college, but hated it the job.
  • She had a life-long dream of being a broadway actress and quit her job to move to NYC. She had no job or friends there, just a plan to study musical theater and audition. 
  • Lily did a lot of different jobs after being in non-profit communications. She was a nanny, a music teacher, she worked at at church in Hell’s Kitchen in exchange for her rent, and she was a balloon hat maker at a restaurant.
  • She had no intention of going into the dating industry at the time.
  • Lily had a friend who had a side job as a matchmaker at a national firm, and they were interested in hiring women who were self starters and who wanted to work independently. 
  • Lily’s friend encouraged her to apply. She went to her interview and had no idea what the matchmaking job would become. It was a very rigorous application and interview process. 
  • There are many matchmaking firms in the country. They are generally looking for women and men who are highly emotionally intelligent, who have the stomach for hard conversations, and who have a strong intuition.
  • You need to read between the lines of everyone you are meeting, you need to have a strong instinct about people, and you need to know the right questions to ask. 
  • The interview process would include questions like: You are sitting at home and your client is sitting at the table in the restaurant waiting for her date to show up. The date just texted you and said he found her online, is unattracted, and he is not showing up. How do you break the news to your client?
  • There is not much difference between people who use online dating and those who use matchmakers. The main difference is access to resources. You need to have a couple thousand dollars, minimum, to work with a matchmaker one on one, and you have to be at a certain level of burnout in dating.
  • She worked with people who were really high earning who just didn’t have time and she also worked with women who worked at non-profits who saved all of their pennies to afford the service. 
  • Lily really liked meeting women at this point in their lives, showing up for them, working with them, and helping them see that love for them was possible. 
  • Lily became the third most successful matchmaker out of 160 at her company. The metric to define success at this company was, after the first date, on their feedback form, they both indicated they wanted to see each other again. A second date was success.
  • Only about five percent of clients were finding long-term success with matchmaking.
  • For most people, specifically women, they would come in disheartened and dissatisfied with dating and with the dating resources, and they would leave the matchmaking experience thousands of dollars poorer, feeling the same level of burnout. 
  • Lily was dissatisfied with that and wanted to create something more long-term with her matchmaking clients, which is why she started dabbling in date coaching and it led her to start her own company.
  • Matchmaking: Sit down, talk about your preferences, Lily would get a list of what you are looking for and narrow it down, and she would go off and vet matches and set up a date for you, then evaluate how it went and move forward from there.
  • Date Coaching: Helping you become your own matchmaker by helping you get beneath the surface of your checklist, what you say you want, to what it is that would actually make you come alive across the table.
  • Lily spent hundreds of hours swiping on Tinder and Bumble. 
  • To find matches, Lily would look in the database, which was people who were clients, people who were recruits, and people from online dating resources.
  • Lily had about 2,000 phone calls with men for her female clients over three years.
  • Lily mostly worked with women. She enjoyed serving them the most. Women tend to be the majority of matchmaking clients. 
  • ”Problem areas” with clients at the Gym tend to be Amazon and Uber, no matter the gender. It is rare that personal care, fashion, and retail are problem areas for men.
  • Women are held to a different beauty standard than men, and companies spend a lot of money marketing to them. There is a reason women spend more. 
  • Dating is a minefield of triggers and gremlins that we have accumulated from the very first day we had a thought. We’ve been accumulating experiences, from which we create stories, from which we create meaning and belief systems in our lives. 
  • If you believe you are incompatible with long-term relationships and that you aren’t going to find love because you are too overweight or are too much, that could become a self-fulfilling prophecy. 
  • Lily can help women create a fulfilling, joyful dating life on their own terms. 
  • Lily isn’t a licensed therapist like Jenny, from Forward in Heels, who was on the podcast in April. Lily highly recommends therapy and Jenny.
  • Lily always recommends that her clients work with a therapist, in addition to working with her. Date coaching is a good supplement to move you forward. 
  • Long-term, date coaching and therapy are better for you than a done for you solution. You are the expert of your own story, and you need to have the long-term skills to be successful no matter what. You need to have the skills to date on your own terms in a way that feels good to you.  
  • So much of dating and happiness comes from you. The challenge with dating when you are younger, is if you are not in a good headspace yourself.
  • Shannon remembers feeling a desire to have a happy, fairytale life, because she didn’t have that growing up. She was convinced she could have that for herself.
  • Shannon was a serial monogamist and was engaged in college, but that relationship ended right before she graduated. Her mom realized she was not ready and said she wasn’t going to let her get married.
  • Shannon then got into another serious relationship after that, and after it ended she tried a dating website and met Bill right after her 24th birthday. After their first date, she told her friends that she met the man she was going to marry.
  • Shannon was married at 25 and divorced at 38. She was so convinced she was going to have a fairytale relationship, but she didn’t have that skillset. The divorce rate is 50 percent, but she didn’t think it would be her. 
  • Shannon had so much baggage and she dated a series of guys who made her feel like it was worse than it was. Two of the guys had parents that were married for 30 years and what seemed like perfect marriages. Shannon felt like she had skeletons in her closet, because her parents had been divorced.
  • On her first date with Bill, she threw out all of her family baggage, and it wasn’t a big deal to him. He wasn’t threatened by her making more money than him, because he was a teacher. Shannon was attracted to him, because he embraced what she felt like were the barriers, or hurdles, to loving her. A challenge later on was that she was almost bullying him, because she has a strong personality.
  • Push back in a relationship always felt like judgment and she didn’t welcome that from him. He made her feel safe when she was 24, because she had so many insecurities. 
  • All anybody really wants is for their gremlin voices to be proven wrong. At the same time, it feels safe to live within the status quo. 
  • Lily believed for many years, based on what family and friends said to her, that she was “too much”. Her mom said from a young age that she was going to have trouble finding a man because of her strong personality.
  • Lily dated men who believed she was extra and they broke up with her because of it. She was seeking out people who was proving her belief right.
  • Brene’ Brown talks about the gremlin voices we accumulate, the mean shame voices that say you aren’t enough. If you are living bravely and courageously with vulnerability, you know those voices are going to show up, but you save them the cheap seats. You save the good seats for people who are in the arena with you.
  • Embrace the gremlin voices. You aren’t going to get rid of them. Look in the mirror and find the things that are right about you. There are more things that are right about you than wrong. It is so easy to believe the negative. We need to love ourselves and see ourselves the way our friends see us.
  • Everybody falls prey to feeling bad about themselves. It is all about developing that resilience and the practices you need to put in place when you fall into feeling terrible.
  • If you believe you are too much, you will reinforce it by meeting other people who believe you are too much. Creating a new belief about yourself takes a lot of work.
  • You need be able to have an honest conversation with your friends about how you speak about each other in a group or how you speak about yourself within the group.
  • Lily recommends taking a negative talk vacation for a night. If you are feeling hopeless or down about dating, try to take a night off about speaking negatively about it and see what that does for your psyche and spirit.
  • When you get out of the habit of downing dating and your body, you realize how much you are doing it. Take inventory of when those negative feelings come up for you.
  • There is so much money spent in the dating process and it adds up. Shannon doesn’t love when she sees spending happen in bad relationships. 
  • Women waste so much money, because of the negativity that is related to dating. 
  • The financial impact of a bad relationship, whether you see it or not, is costly. 
  • Lily does not believe that success in her work is whether or not you get into a relationship. Success to her is defined by a healthy relationship with yourself. If you don’t have a healthy relationship with yourself, it is going to be very difficult to be in a healthy romantic relationship.
  • For women who are making very drastic spending decisions based on the relationship they are in, Lily would ask what’s your why? What is your why beneath this decision? Do you want him to feel taken care of? Ask yourself how are you being taken care of in this scenario. Are you playing out a scenario you saw between your parents? Does he not want to see you or spend time with you if you are not spending this money on him or her? That’s an answer you need to take a look at.
  • People are not examining the whys beneath their decisions, because it is difficult work to do on your own. We are sort of trapped in our own head, mindset, and what we grew up seeing, and it is hard to imagine something different, if you grew up with a negative connotation around relationships or money.
  • Healthy romantic relationships start with a healthy relationship with yourself and your money.
  • Ask the why beneath the why question. 
  • It helps to sit down and evaluate how you are being served in a relationship. In a healthy relationship, you should be serving someone else and they should be serving you an equal amount. 
  • Lily has a Relationship Reflection Guide available on her website. It takes you through, step by step, asking those questions and it’s for after you end the relationship. If you are in a relationship and you feel that maybe it is a bit of an unequal split of love, affection, or money or if there is anything that feels like the seesaw is tipping toward the other person and you are feeling left up in the air by yourself, you need to take a journal, a glass of wine, put on some music, and get real with yourself or a best friend. 
  • Ask yourself what attracted you to this person in the beginning, why you were drawn to this relationship, and how is it supporting you in your dreams and your future. If it isn’t, why not?
  • How does this person show up for your in the hard times? Why? Are you making excuses for them? 
  • A big red flag are the excuses. How many of those do you need to have? The key to healthy dating is loving yourself. The ultimate question needs to be: Is this person taking you to the next level, in whatever way that means, on a regular basis? Otherwise, why not be by yourself? You can take yourself to the next level.
  • Sometimes we leave gremlin voices unexamined, because we think examining them will be too painful to bear. If you are examining them with a licensed therapist in the clear light of day, it is a lot less scary than looking at them by yourself, in your room, at night, alone. 
  • Acknowledging who they are, what they look like, and why they came to be can be a really powerful process and can really transform your relationship with yourself. You learn to level up yourself.
  • If you take the time to address the gremlin voices and start to rescript them with a kinder truth, you can transform what you think is possible in your dating life specifically and with all parts of your life.
  • Lily’s clients get to level up their own concepts of themselves within the context of dating.
  • Lily started date coaching, because she was in a toxic relationship with a guy she met on Bumble. On paper, he was everything she said she wanted. He was super smart and he had a lot of compassion for people, he was funny, and they fell in love quickly. 
  • They went to Paris in the second month of their relationship. A friend was getting married in Amsterdam, but they took too much of a vacation, when she didn’t have the money to spend.
  • When they were in Paris, he said he wanted an open relationship. Because she was not grounded in what she desired in her own worth as a woman and as a human being, she said yes. She didn’t think anyone else would love her like he did, and she thought there was no one else out there for her that would handle her version of extra like he did. 
  • She stayed in the relationship and she became very unhappy. She hated most of the time that she was in it, but she was addicted to the idea that she didn’t have to be alone. She accepted far less love than she deserved, but she couldn’t admit it to herself.
  • Lily’s why beneath her decision of going to Europe and accepting an open relationship and being in it for a year, was that she truly didn’t believe that she deserved extraordinary love. She didn’t believe she was worthy of being loved really, really well. 
  • Lily comes from a divorced parent household and didn’t know what anything else looked like.
  • Women are naturally caregivers and we put other people in front of us, even in relationships. We don’t think enough about how we are being served, because we are thinking about how much we are serving.
  • While Lily was in the relationship, she had just begun the matchmaking job. She realized this because she was telling her clients they deserved love. She did this thousands of times to hundreds of clients.
  • Finally, by speaking those words out loud and being surrounded by family and friends who loved her, those two things collided and she realized her relationship was terrible.
  • Her partner, Chris, came into her life and he made his interest very clear. She felt one door closing and another one opening.
  • Lily was singing in a cabaret show, and the man she was seeing had to leave ten minutes in. Meanwhile, Chris was sitting in the front row with flowers. 
  • Lily ended her relationship and couldn’t be with Chris at the time, because she needed to heal. She took some time away from being in a relationship to start to forgive herself and heal the relationship with herself. 
  • She then began to realize that Chris was here, very present, very loving, with a huge personality, and loved how extra she was. It was a scary prospect. This was something bigger than she thought she was ready for.
  • It was a lot of work to come to terms with how much love he was willing to give her. It was uncomfortable for her to get out of the pattern of behavior that she had been in with accepting so little. 
  • It is work to change that paradigm of behavior and belief, to transform from someone who believes they need to give every cent and every piece of energy to another person to be loved to someone who believes they are worthy of extraordinary and they don’t need to give any money or time that is beautiful or true to them to prove that.
  • Success in dating is feeling fulfilled and joyful. It can even feel like self care, because you are learning about yourself and you are treating yourself well in your dating life.
  • The number one mistake Lily sees women making, is they treat dating like it is a numbers game. It is a conventional dating myth and it doesn’t apply to us today. The myth encourages people to put themselves out there ad nauseam, even if they are really burned out and desire rest. The numbers game says you need to increase your odds by going out and putting yourself out there for every single opportunity.
  • The numbers game mentality doesn’t necessarily increase your odds of meeting someone. What it does is guarantees that you will experience burnout faster and you will have a lot of dating dissatisfaction. 
  • Lily encourages people to examine they ways they have treated their dating life like a numbers game and then make a shift to a minimum viable market mentality. 
  • Seth Godin defines this as the smallest amount of people that are right for you and your business. In your dating life, it is the idea that you are for the few and not for the many. You should be swiping and dating like that, but you shouldn’t be so picky that you aren’t open minded.
  • Dating like this looks like thanking people who ghost you or don’t text you back or don’t seem interested in meeting, because their gift is getting you closer to the smaller number of people who want to meet you. 
  • People are experiencing cognitive overload in the dating space these days, because we have too much access. There are hundreds of thousands of options, especially in a big city like New York, and our brains, scientifically, can only handle nine options at a time before we experience cognitive overload. This means we shut down higher functioning, so we don’t make the best decisions possible for ourselves.
  • Limit the amount of time you are swiping – 10 to 20 minutes maximum per day. Choose a time where you feel good about yourself.
  • What is meant for you will not pass you by.

TAKEAWAY: My biggest takeaway is that dating costs money. It’s not just the cost of getting ready for, and paying for, the dates, but a lot of times there are costs associated with unfulfilling and bad dating situations. The smarter you can date, the better your finances will get. I promise you!

Random Three Questions

  1. What is a food you hated as a kid and do you hate it now?
  2. What is a show you like to binge watch?
  3. If you won a million dollars, what would you do with it?

Connect with Lily

Website: www.datebrazen.com

Instagram: @datebrazen

If you’d like to talk to my team at the Financial Gym to help you prepare, at least financially, to start a business or help run yours better, I hope you’ll reach out to us at the Financial Gym. The number one employer at the Gym is “self employed”, so it’s certainly an area we’re comfortable working in. The great news is that Martinis and Your Money listeners get 15% off Financial Gym services. So head over to, or send friends to, financialgym.com to get signed up today.

Bridesmaid for Hire with Jen Glantz

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Bridesmaid for Hire with Jen Glantz

As an entrepreneur, I always love sharing other entrepreneurs’ journeys with you on this show. I’m fascinated about why people decide to start businesses and the types of businesses they start.

Today’s guest has a really fascinating business. I am speaking to Jen Glantz, founder of Bridesmaid for Hire and Author of the book Always a Bridesmaid for Hire, about why she started her business and the tolls that her entrepreneurial journey have taken on her personal life.

What Are We Drinking?

Jen — Coffee with almond milk

Shannon —  Coffee with sugar and milk

Podcast Notes

  • When Jen was in her early 20’s, a lot of her friends got engaged and married. Very quickly, she became “always a bridesmaid”. She was going to bachelorette parties, bridal showers, dress fittings, etc., and it kept happening weekend after weekend.
  • At about age 26, Jen started having distant friends ask her to be a bridesmaid. These were the type of friends she would talk to once a year.
  • One of these women lived about five blocks away from Jen in NYC, but she never saw her. 
  • Jen felt upset and went home to her roommate and to talk about it. All of these people she hardly knew were asking her to be a bridesmaid. Her friend laughed at her and said that she had become a professional bridesmaid. 
  • These sirens when off in her head and she thought, “I am a good friend”, “I am responsible”, “I show up on time”. If she could do this for people she is hardly friends with anymore, maybe she could do this for strangers.
  • To be a good bridesmaid, you have to be good with people and be able to predict situations. She loved working with people in difficult situations and no one really talks about this.
  • Your wedding is one of the most difficult days of your life, because there are emotions, stress, pressure, money, and people. Jen loved showing up for people in those situations. 
  • If you have a strong heart for people, you will be a good bridesmaid. 
  • Keep the drama to yourself and be there for the bride. It is not about you. If you can’t put someone else before you, don’t be in the wedding party. Your job is to be there for the bride.
  • There is no manual for being a bridesmaid, so most people don’t know what to do or not to do. People are just trying to be the best versions of themselves. 
  • There are so many external factors that make the whole thing awkward, chaotic, and dramatic. 
  • Bridezillas are real. There is so much stress and so much going on. Other people don’t realize how much drama has been going on behind the scenes leading up to that day, between family, money, who gets to bring their kids or not, friend drama, etc. 
  • Jen thinks the more money you spend on the wedding the more you find yourself feeling dramatic and chaotic on the wedding day. You’ve invested a lot in that one day and you start to panic when things go wrong.
  • Some of the happiest people on their wedding day are the ones who didn’t go into debt and did an awesome job planning it with the money they had available. 
  • Shannon’s biggest piece of advice she gives to couples is that this is one day of your life. You are beginning a long journey with someone else. A lot of things are going to come up. 
  • It shouldn’t be the most expensive day of your life, it should be the most fun day of your life.
  • It was a Friday night when her friend had said she was a professional bridesmaid, and Jen started thinking about turning this into a business. 
  • At the time, Jen was working full time at a tech start up. She was a copywriter and she loved it, but she is the kind of person who was hustling, even when she had a full-time job. 
  • She was doing some freelance writing and was dreaming of starting a business. She always had a love of doing many different things.
  • Jen was a poetry major in college and had no business experience, but she had an idea. 
  • To test her idea, she posted it on Craigslist. She does not recommend this now. It felt right and logical at the time. Now she would never tell someone to do this.
  • She created an ad on a Friday and wrote all of the things she would do if she was hired. The list included helping you pee while you are in your wedding dress, helping with friend and family drama, dancing with your relatives, being the friend you wish you had, and at the end of the night disappearing from your life. 
  • She was a writer at the time so she made the ad anonymous.
  • The Monday after she wrote the ad, her life changed. She didn’t tell anyone at work what she did, but there was a Buzzfeed article all about her Craigslist ad that went viral. 
  • Jen had hundreds of emails from women asking if they could hire her.
  • There is a gap in the industry. One in four people do not have any close friends they can ask to be their bridesmaid.
  • What really pushed her to do this was reading the emails. People told her really personal stories about situations they were in and problems they were having with their friends. 
  • Jen realized that nobody was talking about this. A lot of female friendships dissolve, they end, or you go different ways, and there you are at your wedding and you have to display the friends you may not have. Not only that, you are missing the support system that you desperately need.
  • There was no other vendor out there that supported the bride. Nobody is hired to be with you when you are falling apart. Every bride can point to one part of the day where they were falling apart. 
  • Jen left work around noon on that Monday to go to lunch, and she called her mom. Her mom already saw the article, because it had gone viral, and Jen had contacted Buzzfeed to let them know it was her, so her name was attached.
  • Jen went home and for the next couple of months, she didn’t sleep more than a two hours a night, because she started a business.
  • She had experience building a website, so she did that overnight. She read through hundreds of emails, based on what people were looking for, and that is how she created her initial packages. 
  • Jen booked her first couple of weddings that week and her first one was in Maple Grove, Minnesota. She started this business in less than three days, by herself.
  • During this time, she had her first live TV interview for an Australian morning show. When she got there, they asked her how much this cost, and she said it was a free service. 
  • Her mom saw the interview and said she did great, but she had to charge for this service.
  • Usually when you start a business, you can see what other people are charging, but she couldn’t do that in this situation.
  • Jen started off low — less than $1,000. As she started doing more and more of them, she put together contracts that the bride would sign. It included everything that could go wrong and all the details. She also put together prices based on how long they needed her (6, 8, 12 hours, bachelorette party, etc.). 
  • She got smarter as she made every mistake in the book, and she didn’t finalize her prices until she was about six months in.
  • For about a year an a half, Jen worked full time, she did freelance writing on the side, and she got a book deal to write her second book. On weekends and during the week, she was a bridesmaid for hire. 
  • One weekend she had three weddings. She still showed up on Mondays at work.
  • One day in October, she got the news that her company was going to be doing layoffs and she was the first one to be let go. Her boss chose her, because he said she shouldn’t be there any more.
  • Jen was devastated when she left, and she told herself that she would never work for someone else again. 
  • Jen called her mom and her mom said this was the best thing that could ever happen, because her feet were hanging off the mountain and she needed someone to push her so she could fly.
  • There was something beautiful about having that guaranteed income coming in every month from her job. She was scared and it hurt her ego. She thought she was superwoman, working days and nights and burning herself out.
  • Oftentimes when people are let go, they end up someplace better. It is a gift from the universe that is forcing you to grow, expand, and pursue something different. 
  • Getting laid off was a little embarrassing to Jen at first. Everyone she has talked to who was laid off has ended up in a better situation. 
  • Things happen for a reason and we need to not fight them, but instead keep pushing forward.
  • Jen was laid off in 2016, and she was a year and a half into her building her business. Aside from Bridesmaid for Hire, she continued to do other side work like consulting, coaching, and writing, because she knew the wedding industry had seasons that were more busy than others and she needed to make sure she made enough to support her life in NYC.
  • She took up as many side hustles as she could. She started speaking more and started charging to speak. 
  • It became an Excel spreadsheet game of wanting to make X number of dollars or she wanted to make more than the last month.
  • Jen doesn’t think a full-time job is right for her. She likes doing different things and she feels alive and challenged when she is hustling and when she has four or five different things going on.
  • She never knows what the future will hold, but she loves the hustle she has created, even though some months are frustrating and stressful and she doesn’t sleep.
  • The entrepreneurial journey is not for everyone. There are ebbs and flows to every business. If you cannot handle the really difficult times, then it is not for you. There is no shame in going back to a full-time job. 
  • Jen has lost a lot of relationships and friendships, because she works most nights and weekends. Finding balance when you are an entrepreneur is tough, because you start to equate every hour with a dollar sign.
  • It is not as glamorous as it sounds. It is hustling, and giving up going on vacations, and giving up seeing your friends. There is a lot to it that people don’t see.
  • When you are the sole source of income, and you are not getting a regular income, you feel like you need to say yes to everything and hope your business grows.
  • You don’t have time for your friends. Shannon is six years into building the Gym, and she is now sort of seeing friends. Shannon’s oldest and dearest friends, Susan, is always there for her but Shannon never sees her. 
  • The day Shannon went on the Today Show, she got a voicemail from Susan and she was crying because she was so excited for her. That was one of Shannon’s favorite well wishes. 
  • The love of Shannon’s life is the Financial Gym. It is difficult to maintain a relationship, because there is so little time and entrepreneurs have different priorities. 
  • Jen’s boyfriend is also an entrepreneur and he not only gets the hustle, he is also doing it himself. He understands what she is doing and respects her for it.
  • When it comes to dating, you need to know yourself and what is important to you prior to the first date. 
  • You need to make other entrepreneur friends who understand what you are going through. When you are building your business, there are going to be people in your life who get it and some who don’t.
  • People think balance is even. Shannon thinks of it as a pie chart. There are going to be times when one of those pieces is bigger than the others. You need to be mindful of those pieces and what you want to give your energy to. 
  • For Shannon, her evenings are typically crazy, but she tries to work from home on Mondays and Fridays. She tries to not schedule meetings before 9:00am, because it is important for her to wake her son up, make breakfast, and get him on the bus. When she is with her son, she tries to not be on her phone. Sometimes it is harder than others.
  • It is important to manage yourself and your needs. Jen tries to get out of the house every day and do some physical activity, even if it means walking around the block. You need to also give yourself some rest. Jen schedules time for yoga and it is non-negotiable.
  • One of the best decisions Jen made was getting help. There was a point at about nine months of building her business where she was feeling lost. She was booking so many weddings that she needed to turn people away, because she was only one person. She had about 20,000 to 30,000 people who wanted to work for her. She couldn’t hire everyone, but she could hire a few. Jen needed to figure out how to monetize that.
  • She found a free place called Score NYC, where you could meet with retired business professionals who can help you. Jen met with a man named Ray, who was 86 years old, every single Saturday for about two years. He was not in the wedding industry, but the advice she got from him has changed her life in many different ways.
  • Finding a support system is so important.
  • Jen found a therapist when she was dealing with depression, and she she reached out to the Financial Gym when she realized she needed help with her finances.
  • One of the best things Jen did was look for help when she needed it. Admitting that you need help is difficult. 
  • Jen rescheduled her first session at the Financial Gym three times, because she was scared to talk about her finances. It wasn’t as scary as she expected.
  • We are more comfortable getting physically naked than financially naked. Many people would rather do public speaking than talk about their finances. Sharing your finances is one of the bravest things you can do. 
  • When you are ready for help, you will rise to the occasion and really incredible things will happen in your life when you open up and be honest.
  • One of the worst mistakes Jen has made was getting stuck in a rut of fear of rejection and failure. She has been writing on the internet since 2010 and has been rejected over and over, but there is nothing like being rejected because of your business idea. 
  • When you have a business idea, you have to be willing to pivot, adjust, grow, but it is hard sometimes. She put so much pressure on herself at times not to fail that she didn’t do anything — she just kept things going and didn’t innovate and change things fast enough.
  • Everyday she tries to aim for failure, whether that means sending an email to someone she doesn’t think will respond or ask for something she is not sure she deserves to get right now. Think of a new idea and put it into motion. Moving is better than sitting still.
  • Sometimes business rejection is more difficult than personal rejection, and sometimes it hurts more than you can anticipate.
  • When you get rejected, look at that as a sign you are moving forward. They know you exist and you are out there. Keep going. If you believe in something, you have to see it through.
  • Jen’s biggest obstacle of taking her business to the next level is continually figuring out the trends in the wedding industry. That industry is always changing, especially in the world of technology and Instagram. It is continuing to figure out how to bring value to people at different touch points, adopting changes, and figuring out different ways to innovate. 
  • If you want to start a business, do it now. Time goes so quickly. Don’t doubt yourself, don’t tell people, just go. Even if all that means is researching on Google 15 minutes a day. Baby steps are going to be the best thing you can do.
  • If you are really passionate about something, what are you waiting for? Don’t doubt yourself, just start.

TAKEAWAY: My biggest takeaway is that most people talk about the financial tolls that starting a business can take on your life, but I don’t think enough people talk about the personal tolls, especially when it comes to maintaining your friendships. Speaking from experience, it’s really hard to balance it all and friends are typically the first to go on the back burner when you have a business to run. 

Random Three Questions

  1. What was your favorite wedding?
  2. What do you do with all of the dresses?
  3. If this was your last day on earth, what would be your last meal?

Connect with Jen

Website: www.jenglantz.com

Podcast: You’re Not Getting Any Younger (Episode 28 with Shannon)

Book: Always a Bridesmaid for Hire 

Instagram: @jenglantz

If you’d like to talk to my team at the Financial Gym to help you prepare, at least financially, to start a business or help run yours better, I hope you’ll reach out to us at the Financial Gym. The number one employer at the Gym is “self employed”, so it’s certainly an area we’re comfortable working in. The great news is that Martinis and Your Money listeners get 15% off Financial Gym services. So head over to, or send friends to, financialgym.com to get signed up today.

Getting Financially Naked with Paige

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Getting Financially Naked with Paige

At the Financial Gym, we call the first meeting you have with a trainer the “financially naked session.” In this meeting, you share everything about yourself financially so the trainer knows where you’re starting and so he or she can make the plan for how you can get where you want to go. Above all other meetings, this one scares clients the most because they are afraid or ashamed of their financial situation. A few months back on this podcast, almost a year ago, I shared my financially naked session, and now it is a regular series on the podcast.

Getting in the hotseat today is our client Paige. Paige has a really fascinating backstory and I applaud her for her bravery in sharing it, but I have to warn you that if you have triggers around substance abuse or physical abuse, you may want to skip listening to this episode.

What Are We Drinking?

Paige — Crisp Rosé

Shannon — Hampton Water Rosé

Podcast Notes

  • Paige has been a podcast listener for almost three years and she joined the Financial Gym about a year ago.
  • Shannon feels like she and Paige are long-time friends.
  • Paige was attracted to the podcast because Shannon is unapologetically who she is, and that level of vulnerability cannot be fabricated.
  • We are all unique human beings and we all have a voice. There is a reason Shannon is saying things and the people who are meant to hear it will hear it. She cannot lose sleep over the people she is not impacting, because there are people she is impacting.
  • The people in the cheap seats are the ones that will put you down and yell the loudest, but it is the people who buy the prime seats who will cheer you on.
  • Hoda Kotb recently posted on Instagram, “You will be too much for some people. Those aren’t your people”.
  • It is not Shannon’s intention to purposely inflict harm on another person, but if that’s how they are receiving it, they are free to shut her out. Don’t tune in, don’t subscribe, and don’t follow.
  • The more Shannon is out there, the more she realizes why she is supposed to be out there. She realizes the importance of being open and honest. We each have to live our own lives.
  • Paige has a really fascinating background, because it is truly unique.
  • Paige was born in Oregon and grew up with her two siblings, brother and sister, and her mom and dad.
  • They grew up in significant poverty. Her mom grew up in her own tough situation of abuse and drug addiction, and that translated into Paige’s family’s life. Until someone comes in and breaks that pattern, it is cyclical.
  • Paige’s mom was with three men in just under four years and she married Paige’s father, who is a kind and hard working man. After a couple of years, her parents got divorced, and they were living in a trailer park.
  • Paige grew up in trailer park situations, which is a hard way to grow up.
  • Paige has very distinct memories that, looking back, she should have realized her situation. When she was four, her family moved to Bend, Oregon, where she lived until she was 18 years old. They didn’t have trash service, so every time they emptied the trash, it would go to the backyard. Eventually they had their trash service reinstated, but in the meantime, they had months and months worth of trash sitting in the elements in their backyard.
  • Paige’s chore after school was getting the trash from the backyard and putting it in the trash can. When she was 10, Paige had a friend that wanted to come over and play, but Paige had to do this chore. She told her friend that if she helped pick up the trash, she would be done quicker. Paige’s friend came over and vomited because of the smell and had to leave. They never hung out again.
  • It was at that point Paige realized that maybe it wasn’t normal to have your trash service turned off or to not have food in the refrigerator regularly.
  • Paige was on the free and reduced school lunch program and she thought it was normal to get your breakfast and lunch for free every day.
  • She realized they weren’t paying for things and their water and electricity was being turned off, if not both then one or the other, on a semi-regular basis.
  • This was when she realized she was growing up in an environment that she wasn’t seeing being mirrored around her. She described it as “icky” and she wasn’t like the other kids in her neighborhood, so Paige would go to other kids’ houses to play.
  • After her mom and dad divorced, her mom married another man. He was an extremely abusive alcoholic. They were all being physically abused, including broken bones and bruises.
  • They would leave the house and her brother would go to their grandparents’ house, her sister would go across the street, and Paige would find friends in the neighborhood and spend as much time with them as possible.
  • After the divorce, Paige’s dad lived in Portland, which is three hours away from Bend and it is over a pretty significant mountain pass.
  • He would call Paige all of the time and when the phone line was turned off, he came over and installed a separate phone line in her room. He paid the phone bill monthly, so they would have a way to call him if needed.
  • When she was young, her dad wasn’t going to live in the same town as her mom, because her mom was in a very toxic place in her life.
  • Her dad was present in Paige’s life and would call, send gifts, and drive over to pick her up and take her back to Portland on a Friday, a six hour drive, and then bring her back on Sunday, which would be another six hours, when her mom couldn’t afford to drive and meet him halfway.
  • Paige’s sister and brother have different dads and her dad wanted to see them and also take them to Portland, but Paige’s mom and stepdad decided to not let him do that.
  • They asked for Paige’s dad to pay child support for the other two kids, and when he didn’t they said he couldn’t see them any more.
  • Paige’s and her siblings were not told this happened until years later, so at the time they were more angry with Paige’s dad than her.
  • Paige got away from the chaos for one weekend a month to be with her dad, and it gave her 36 hours away.
  • Paige’s brother would go to their grandparents’ house up the street and they were intentionally ignorant about what was happening in Paige’s house. Paige and her sister had to stay with their stepdad, so they both were resentful to their brother since he had a regular place to go.
  • It was very challenging for Paige to stay focused in school. She loved school, she tried really hard, and she graduated high school. There was never really any risk of her not graduating, but she was exhausted.
  • When you live in an environment when you are constantly in fight or flight mode, it is exhausting.
  • When Paige was in the second grade, she remembers talking to another student about Roman numerals. No matter how hard she tried to memorize them, she couldn’t get them to stick in her brain. It was very clear to her then that they were growing up in two very different homes. He lived in a wealthier situation and she didn’t know if they were going to eat that night.
  • This is when she started backsliding in math and science. Up until that point she had been pretty good at those subjects.
  • When you are in that situation and you go home, you don’t think about school, because you just have to survive.
  • Paige’s mom was dating her stepdad when she was still married to Paige’s dad. Her stepdad was around when Paige was age four until age eleven.
  • At that point things started getting trickier. Although he wasn’t bringing in a ton of money, and he was spending a lot of it on alcohol, it was an extra source of income. As soon as he left, they were evicted and had to move into a motel.
  • Paige’s mom was a waitress. She was always a hard worker and she always had a job for the most part. After Paige’s stepdad moved out, her mom got a job at the motel they were living in, running their events department. Now her mom works in the medical field as an office assistant.
  • When they lived in the motel, it was her mom, brother, sister, and her living in a two queen bed room with all of their stuff. Paige went down to the pool a lot just to get away.
  • Paige fell at the pool, and later found out she broke her tailbone, but was too afraid to tell her mom, because she knew she didn’t have the money to go to the hospital. It took her well over a year before she didn’t have to take her time standing up.
  • Paige’s dad had met a wonderful woman named Becky when Paige was in the fifth grade, dated her for several years, and then married her. They eventually moved to Bend.
  • Becky had two kids, she kept an immaculate house, and she always had food stocked in the refrigerator. Paige started going over to their house regularly, when she was 11 years old.
  • She started realizing that things were different there, because they had money to plant flowers in their yard, people were home at night, and they had family dinners.
  • Her stepsister is one of Paige’s best friends now. They are only 10 months apart.
  • It was interesting to see the differences between their home lives, but it wasn’t until she was 16 that she had a moment, when she was standing in the driveway at her mom’s house. Paige had asked for months if she could get her bellybutton pierced and her mom kept saying no. She came home one day and her sister had gotten her bellybutton pierced and her mom said it was okay because she got good grades.
  • There was an imbalance, because her mom thought she needed to protect her sister more, since Paige had her dad. She thought if she didn’t change her life now, she would stay in toxic relationships forever.
  • She moved out of her mom’s house when she was 16. Her dad and stepmom had just given her a car, which Paige paid part of. The rule was that she could only use the car when she was at their house. One day, she packed up her stuff and moved to her dad’s house.
  • When she moved in with her dad, it was the first time she talked about college.
  • It was about this time, at age 16, that she started following the Lord. Her faith is now central to her life. She had gone to church a little during elementary and middle school. Paige worked at Red Robin and she was spiraling and crumbling at the weight of what was happening at home. She was dealing with the desire to be loved and cared for in a way her mom wasn’t able to provide.
  • A girl at work pulled Paige aside and asked if she could talk to her about it. She said there is freedom from what Paige was going through. Paige called her a couple of weeks later and asked her a bunch of questions. She didn’t have all of the answers but listed what she knew to be true of God.
  • None of Paige’s immediate family go to church on Sunday or believe in God. Paige thinks her mom felt like she was losing her, because Paige wasn’t able to continue living in the environment her mom was providing. Her mom was resistant to Paige reading her Bible.
  • She believes her mom did the best she could with what was available.
  • After high school, Paige applied to a few different Christian colleges. She graduated high school in 2008 and central Oregon had the highest unemployment rate per capita in the nation at that time. About 60 percent of her town was laid off, because they were all general contractors and everyone stopped doing work on their houses.
  • There was a point where you could drive around town and there were houses boarded up all over the place.
  • Paige’s stepmom was a painter and she was out of work for a long time. Paige assumed her dad and stepmom were going to help her pay for college, because other kids’ parents do and because they had money to buy things.
  • The colleges she was applying to were private and very expensive. Paige’s stepmom sat her down and said they could not afford to help pay for those colleges and she needed to find some other options.
  • On a whim, Paige applied to Portland State University. She wrote an essay for their diversity scholarship for socioeconomic diversity. Her essay was about growing up in poverty and how that impacted her life.
  • Paige received the scholarship, which paid for one full year of tuition at Portland State University. She didn’t have any money for housing or anything else, so she took out student loans.
  • The first year was terrifying, but she lived with a wonderful woman who gave Paige a massive discount on rent. She didn’t realize what a big discount it was until years later.
  • It is a hard school to find a community, if you are not living near campus, so she moved to Bellingham, Washington, and attended community college after she was rejected from Western Washington University.
  • If she had attended university right away, she would have needed to pay out-of-state tuition. She took a year off of school and then went to  community college.
  • Eventually she transferred to Western Washington University and she did her time there in a year and a half. She ended up taking 60 credits her senior year, because she knew if she didn’t do it then she never would.
  • Paige finished her degree in five years at three different schools. She wanted to be a lot of things when she was younger.
  • Encourage young women to stick with STEM!
  • Paige chose to back away from STEM subjects because she couldn’t keep up with school. It was also the stigma of if she didn’t know it on the first try, she must be stupid.
  • Hillbilly Elegy, by J.D. Vance, is a great book and somewhat mirrors her story. He said, “a lack of knowledge is not the same as the lack of intelligence”.
  • Paige wanted to be a doctor when she was younger, but by the end of elementary school she was terrified of math and science, because she thought she was too stupid.
  • She then thought of going into nursing or broadcast journalism. For a long time she wanted to be an actress, but after Paige started following God, she realized that was not the environment she should be in because of the pressure.
  • Paige knew she was good at speaking and writing, and particularly public speaking. She got a degree in communication with a minor in multimedia and diversity.
  • After all of this, Paige ultimately ended up working for Microsoft. She was at school in a communication class in the fall quarter. Her professor told the class they could either go to the career fair, which was during the time of that class, or come to class.
  • Paige put on her best suit and went to the career fair. There was a booth for Microsoft and she stood in a long line to submit her resume that she worked on in one of her communication classes.
  • She got an email a couple of days later from Microsoft asking her to do a phone interview. Then they paid for her to go to Bellevue, which is outside of Seattle, and she spent two days there interviewing. It was five interviews in four hours and she only had $75 in her bank account, and she spent $50 of that to fill her gas tank to get there and back. She didn’t have any money for food so she didn’t eat during the time she was there, because she didn’t know she had a stipend for food.
  • After her interviews, they pulled her aside and offered her a job. She was shocked. She graduated college with a job as an associate consultant. Six years later, she is still working for Microsoft.
  • Paige’s family was thrilled. She was offered the job in January of her senior year in college and she graduated in June. There is a picture of her dad hugging her and crying at her graduation. Out of 3,000 graduates and only two photographers, they managed to capture that photo. Her family has cheered her on the entire time.
  • Paige now earns six figures and she is no longer the little girl with trash in her backyard.
  • When you grow up not having enough, you are always afraid you are going to lose what you have. That was the biggest mindset shift Paige went through. The biggest thing for her was how to operate with so much money. She didn’t start out with six figures, it has grown over time.
  • There are two parts to the poverty mindset:
    • I am going to lose everything I have, nothing is permanent, and if I lose this everything is over.
    • I want to buy this expensive item. If I can’t buy this expensive item, it means I can never buy this expensive item.
  • A big financial challenge Shannon sees when people go from having so little to a lot is that there is a desire to have so much. If feels like an entitlement because you have worked so hard for it.
  • Shannon started making money and then starting spending money, because she had a need to get those things to justify the success in her life. She had to realize that was not what defines success.
  • It is going from one extreme to another.
  • Paige recommends counseling for anyone whose situation mirrors hers in any way. There is a certain feeling she gets when she feels like she can’t have something. Her heart starts racing and she feels like she is going into a panic mode. She had to learn how to talk herself down by telling herself she is going to be okay if she doesn’t buy those shoes. She will still have other shoes to wear and she will look just as fabulous.
  • When you are in a panicked mode, it is not a good time to make big decisions, financial or otherwise. Paige waits until she is in a logical mode. If she is eyeing a purse, she will start saving for it, even if she can buy it now. It buys her time to figure out if she really wants it.
  • This is an unfortunate side effect of overcoming a struggling background. Most of Shannon’s clients that come from this background struggle with the spending side of it. It creates another extreme and it hurts you just as much.
  • Paige grew up with a kind of identity crisis. When she started at Microsoft, she had the financial resources and the stability to begin the process to find out “who am I” in this greater world.
  • In the book Educated, author Tara Westover said, “The greatest luxury of having money is not having to think about money”.
  • Paige went on a soul searching journey, but it landed her in more debt.
  • If you are struggling with identity or who you are, no amount of buying the shoes everybody else is wearing or going on the vacations everybody else is going on is going to make you feel like you fit in at that table or in that social circle.
  • Go on your personal journey, but don’t let that journey get you more in debt.
  • The stuff you can buy doesn’t define you. It is important to be mindful of where you came from and what you have overcome. Don’t ruin your story by overspending and creating a lifestyle that is not going to bring you the joy you thought you were missing out on at the beginning of your life.
  • It helped Paige to have somebody safe to talk to about money, coming up with a plan, and figuring out how to get out of debt. Once Paige got out of debt she joined the Financial Gym, but she recommends joining before that time, because she wishes she would have joined earlier.
  • Once you get through the tactical stuff with your trainer of saving and spending, you see a clearer picture and that is where the magic happens. The first six months is a lot of nuts and bolts. Once you see results you start to have more options.
  • Don’t be afraid to be vulnerable with your financial trainer.
  • You have complete control over your life, it just takes some help.
  • Be aware how your past affects your future. The biggest misconception of money is that it is just black or white. It’s not – there is a lot of grey. Your past will affect how you handle money, because you are not a robot.
  • Paige is starting a fashion and lifestyle blog call Brave Originals and it can be found at www.braveoriginals.com, and on Instagram at @braveoriginals. For the ones who chase their dreams on their own terms.
  • When you reach your dream, dream bigger.

Takeaway: My biggest takeaway is to be mindful of the effects your past will have on your financial decisions in the present. It’s easy for us to justify the decisions we make, but are they coming from a healthy point of view and will they contribute to our financial health in the future? If not, take the time to reflect on why you’re making the decisions you are, so you can start making better decisions in the future.

Random Three Questions

  1. What is the big goal you have for yourself?
  2. What is a show you like to binge watch?
  3. If you won a million dollars, what would you do with it?

Connect with Paige

Blog: www.braveoriginals.com

Instagram: @braveoriginals

If you’d like to get financially naked with my team, and drop any fear or shame you have around money, I hope you’ll reach out to us at the Financial Gym. My trainers have literally seen it all, so nothing will surprise us. We don’t care how you got here, we just care about getting you where you want to go.  The great news is that Martinis and Your Money listeners get 15% off Financial Gym services. So if you’re ready to manifest your dreams, like Paige in 2019, head over to or send friends to, financialgym.com to get signed up today.

Invested Development with Amanda Holden

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Invested Development with Amanda Holden

I think of financial health as having a number of pieces to the puzzle that all come together to make us financially healthy people. The primary pieces, or the outline of the puzzle, include budgeting, expense management, saving, credit management, debt management, investing, insurance or risk management, and income management.

At the Financial Gym, we help our clients figure out all of these pieces and where they fit into the puzzle, and, while I think they’re all equally important, I think the investing piece is typically the last one people figure out. Either they haven’t gotten to a point where they’re saving enough to make investing a priority, they’re afraid to start, or they don’t know where to go to learn more about it. That’s why I’m excited to have Amanda from the Dumpster Dog Blog and Invested Development, to talk more about investing and the amazing resource she’s created to help you get started, or get more comfortable with, the investing piece of your financial health puzzle.

What Are We Drinking?

Amanda — Spicy Margarita 

Shannon —  Schweppes Grapefruit Sparkling Water with Tito’s Vodka

Podcast Notes

  • When Amanda graduated from college she needed a job, so she started working for an investment management firm in San Francisco. She started there at the beginning of 2008, right at as the financial crash was happening. 
  • She had a front row seat to the rollercoaster, and it was a wild time to be there because the success of the firm was so tied to the stock market in general. About 70 percent of her department was laid off, just a few months after she started working there.
  • Amanda managed to not get laid off, and she made it through the financial crisis with that company. She ended up working as an investment counselor and worked directly with their high net worth clients. She did that for about three or four years.
  • She was the point person working directly with the clients, so she was the one on the phone or meeting with them.
  • Amanda would keep them apprised of portfolio strategy or answer questions about the market, and she would get to know their personal financial situations. It was basically letting old, rich white guys complain about their money to her all day.
  • It was a great job and she learned a lot. The learning curve was very steep. She was thrust into this position.
  • When Amanda was an associate, one of the guys from the investment counselor department came down and told her to work for them. She was the youngest woman in the department.
  • She wouldn’t be able to do what she does now without that experience. It would have been hard to learn what she did without that front line experience, but helping rich men get richer was not going to be it for her.
  • Amanda spent eight months saving up all of her money and that was the genesis of her nickname, Dumpster Dog, which is the name of her blog. She got super scrappy about saving money.
  • She quit that job to travel. While traveling she thought that her work with investments wasn’t done, and she started thinking of ways she could get the information back to the demographic she cares most about, which is young women, or anybody who has felt left out of these conversations. 
  • These conversations are typically reserved for people who are already wealthy.
  • Amanda ended up back in her hometown, Portland, Oregon, and that is where she has been for the last couple of years, getting her business off the ground.
  • Her business, Invested Development, is essentially investment seminars, writing, and an online course.
  • Amanda said that wealthy people do not necessarily know more than those without money.
  • In the aftermath of 2008, Amanda’s job was to assure her clients that the situation was bad, but it is just a normal part of the cycle. She was mostly begging them not to do something that would ultimately hurt them in the long run, like go to cash or sell their investments at a loss. 
  • The amount of reminders it took was unbelievable. Most of the people Amanda worked with did not acquire their money through investing, it was mostly through their family or through a business.
  • It is an advantage to smaller investors to just jump in and get your feet wet with small amounts. It would feel crushing to do something wrong with $100, but it would feel worse to do that with $10 million. 
  • Shannon also had that misconception that people with wealth had more investment knowledge. Part of her training as a financial advisor was to do role playing. In one of those sessions, she had to explain an investment portfolio that she was trying to sell. Shannon started talking about asset allocation the way she does now, with a pie analogy. 
  • Shannon’s mentor told her that the pie analogy might work with a small mom and pop investor, but when you are working with a sophisticated investor she needed up her game. 
  • After talking to clients, they actually did appreciate the analogy, because they never understood what their advisor was talking about.
  • Amanda does her investment seminars for universities, sororities, in corporate settings, and for women’s groups.
  • One of the hardest seminars she did was at a high powered law firm where the women in the room had these incredible jobs, but she got the sense that they were almost competitive with one other and nobody was vulnerable enough to ask a question or show that they didn’t understand something.
  • Amanda loves going into the sororities, because they don’t think they should already know this stuff, so they are laughing, asking questions, and not caring about looking dumb. 
  • Shannon did an Investment 101 seminar at the Financial Gym one night, and there was a woman who raised her hand and asked Shannon to explain what the markets are. Everyone kept telling this woman she needed to invest in the markets and she didn’t know what that meant. 
  • You cannot just assume that people know what it means to invest in the market. If you’ve never taken a financial class, how should you know what that means.
  • The things you take for granted for knowing are the things that tons of people don’t know. 
  • These are not naturally occurring things that we have intuition around, this is not something that is imbedded into us. We’ve created this crazy system and it really takes sitting down and familiarizing yourself with it if you want to learn about it.
  • It is a whole new language and there is no reason why anyone should know it. It is just like any language, there are degrees of how much you should immerse yourself in it. 
  • At the end of the day, there is not a lot that you need to know about it. There are some high-level things you should get comfortable with. On the other end, you could get into the weeds, but the general population doesn’t need more than the high level ideas and concepts. 
  • A lot of people don’t invest because they don’t understand it, and they are missing out. 
  • If you are scared of investing because you are scared of losing money and your money is sitting in a bank account, your worst fears are happening, because you are losing money every day.
  • One of the greatest things about investing, at least from what we’ve seen historically, is that taking these extremely simple strategy steps and doing a very set it and forget it and not getting in there and trying to get cute and have this complicated portfolio is actually the best way to invest. 
  • Doing something that is completely automated, where you think about it maybe an hour a year, has actually performed the best historically. 
  • When picking stocks, it is all over the place and you cannot predict what is going to happen. A simple strategy is best. 
  • Stock picking can be such a fool’s errand for so many reasons. Shannon has recommended picking two ETFs and calling it a day.
  • Stock prices aren’t moving on fundamentals, they are moving on sentiment. They are moving on buyers and sellers buying and selling.
  • It can take years or decades for stocks to balance out. 
  • There are different types of markets: stock market (also called equities), bond market (fixed income), cryptocurrency market, real estate market, commodities market (oil, gas, gold, silver).
  • There are different types of markets that represent different types of assets. When you hear asset allocation, it is about having different types of those things and representation of different markets.
  • The boring, plain vanilla markets you need to worry about are stocks and bonds. 
  • If you turn on any minute-by-minute financial news programming, they will lead you to believe the most important decision is should you own Apple stock or should you own Microsoft stock.
  • In reality, the most important decision you are going to make is should you be invested in stocks, bonds, or cash. The big overarching asset allocation is the most important decision you need to make. What stock should you invest in should fall to the very bottom of an inverted pyramid of important decisions. 
  • If you are making a decision about how to invest your portfolio, start with the big picture decision first: should I invest in stocks, bonds, and what combination of the two. Take a step back and set your goal. When do you need this money and why are you investing at all. 
  • First you need to set your goal. What is the money for? What do you have coming up in your life journey? You need to know what is already in movement and where you want to go. 
  • If someone has an idea of what you should do with your money, without knowing your financial situation or your goals, they are probably going to get paid if you do what they say.
  • You can really only invest with a goal in mind and with an understanding of the different asset allocation classes, and then you need to puzzle piece together what makes the most sense, given what we know about these different asset classes. 
  • One of Amanda’s pet peeves is when people work with a financial advisor, or a robo advisor, and the first question they ask is what is your risk tolerance. This is a good question and we need to talk about it, but it means nothing.
  • Robo advisors are only as good as the information they receive.
  • Bridget was Shannon’s first employee and she started as a client. In her first session, Shannon learned that Bridget had an investment portfolio at Betterment in a Traditional IRA. She also had a 401(k) at her current company, so she wasn’t going to get the tax benefit of the Traditional IRA. Her money should have been in a Roth IRA. Luckily, she hadn’t filed her taxes, so she could change it to a Roth IRA. 
  • Bridget had a house goal that was five years away and her asset allocation for that was the same as her retirement asset allocation (90% stocks/10% bonds). They ended up starting a new portfolio that was more conservative to balance out the aggressive house fund. They shouldn’t be the same. A house goal in five years should be different than retirement in 50 years. The robo advisor applied the same allocation to all of her life goals. 
  • If you are feeling a little bit clueless about how to put information into one of these sites, you need to take a step back and understand some of the basics of investing. 
  • One of the biggest things Amanda does is help people understand their options between robo advisor, DIY, and picking individual stocks. If you  go with a robo advisor, fingers crossed, it is going to be fine, but you should also know exactly what service they are providing you.
  • Be wary of some of the robo advisors, because there are so many of them.
  • Shannon liked Swell Investing because they do more socially conscious investing. She heard them present and thought they were great, and she just heard last week that they are shutting down. When that happens, you need to sell your portfolio and you need to deal with tax issues. Look at some of the bigger firms. 
  • If you are going to work with someone who is going to give you financial advice, they should absolutely be a fiduciary. A fiduciary is somebody that is required to work in your best interest and make recommendations in your best interest. 
  • The conversation of fiduciaries comes in when somebody is actually going to invest your money on your behalf. The Financial Gym is not a fiduciary, because they are not actually going to invest your money.
  • A large majority of investors do not need to follow this standard. Not everybody is a fiduciary.
  • You should want to know and understand everything yourself. Be empowered in what you are investing in. Even if they are a fiduciary, you should be very knowledgeable about what is happening. It is your wealth and your life.
  • Amanda doesn’t make recommendations on investing. The whole point of her business is to get you in a position where you can confidently make decisions on your own. If that means you go with some sort of a wealth advisor, so be it, but she finds that most people who come through her course are not going to go that path.
  • Investing is something that is within our capacity to learn. It is not rocket science, but it does take someone sitting you down and explaining things you should know in a way that makes sense. 
  • In Amanda’s course, she compares everything to dating, which makes it interesting and fun and totally relatable. The idea is to get you in a place where you walk away feeling like this is something you can do on your own, at least as a beginner.
  • What does that mean? Open up a Roth IRA or start contributing to your 401(k). Buy one, two, or three index funds, which is essentially a mutual fund or exchange traded fund (a big basket of some other type of investment).
  • The most popular index fund in the world is the S&P 500 Index Fund. This essentially invests you in the 500 leading companies in the United States. Within your Roth IRA or 401(k), which is just the account, buy a low cost, diversified index fund and call it a day.
  • The words sound very overwhelming if you are not familiar with them, but anybody can learn this information. 
  • You can stay really high level and still feel in control of your situation. You don’t need to get into the weeds and know everything. 
  • When you have someone managing your account, it can cost at least one percent. Over time, you want to earn six to eight percent on your account. Do you really want to give over 20 percent of your investment to fees?
  • If Amanda was going to recommend that someone use a financial advisor, it would be for accountability. This would be to get everything set up and to start contributing to your account, and hopefully for some education. 
  • When you relate one percent with shopping, it isn’t a big deal. If you went to happy hour and your spicy margarita is one percent off, that is an insult.
  • In the world of investing, one percent is so much. The stock market will only give us what it gives us and maybe that is six percent or eight percent a year, which is an average. If one percent is paid in fees, that is 20 percent of your returns right now. With compounding, this ends up being an even higher percent of your potential returns over time. 
  • If a financial advisor is just managing your portfolio, and not doing any other financial planning, you are overpaying. 
  • Invested Development is the name of Amanda’s business. It started out with Amanda just doing live seminars, and she still does those.
  • She loves going into corporations and businesses that have some sort of women’s leadership channel or inclusivity group and doing a happy hour or lunch and learn where she does a really fast Investing 101 that is one to two hours, just to get everybody up to speed. 
  • For companies that don’t offer a retirement fund yet, she educates employees how to do that on their own. 
  • She also does independent seminars and she offers a virtual course. The virtual course is live and is taught by Amanda. She usually does two months on and one month off. She just finished a course in July and she is taking August off. She will have a course in September and October. They are four classes long, each class is an hour and a half, plus as much Q&A until everyone has their questions answered. It is six hours of instruction and her goal is to get everyone confident in their investing knowledge, so they can turn around and make decisions about opening accounts and investing within those accounts on their own.
  • In the course, she covers the account types, all the different ways to invest, asset classes, socially responsible investing, etc. 
  • Amanda has been doing this for about a year now and she has had almost 200 people come through her class. 
  • This type of financial education product is needed in the world today. The course costs $249. 
  • If you are not investing, because you don’t feel confident, you are going to make more than that in your investment returns and saving on fees. 
  • People should be investing in their financial health in different ways, whether it is investment knowledge or budgeting knowledge.
  • Seventy six percent of Americans are living paycheck to paycheck. We have big financial health issues in this country, and there is no formal financial health education. 
  • You need to invest in it. The mistakes you avoid will be more than the investment in the course. You are likely spending $250 in other ways. 
  • Shannon put $11,000 into Betterment a year ago and there were times where it was $10,500, but now it is $11,609. She hasn’t done anything with it and it is up $600 in a year. 
  • It is like taking your money off the sofa and putting it on the treadmill. We work so hard for our money and we should want to maximize it. For each dollar we make it is one less dollar we need to earn.
  • There are two ways to make money, (1) exchange your time for money, or (2) have your money make you money.
  • If you just invest money over a period of time, that could equal a year you don’t need to work.
  • There are so many fundamentals of the stock market that still make it a good time to invest. There are so many companies that have a ton of cash and are still going to grow.
  • Earlier this year Uber, Pinterest, and Lyft were not public companies. There are always new entrants to the market that will help it grow and give you growth too.
  • We are due for some sort of significant correction, which is greater than 20 percent. Until that happens, there are still a lot of positive things to say about investing. 
  • You cannot time the market and when the next bear market will occur, which is a dip that is 20 percent or more, so what is the point of trying.
  • If we go through a dip, it is not that big of a deal. That is a normal and natural part of investing. If you have a long time to make your money grow, a dip in the market doesn’t really matter. If you are savvy about it, a dip is a good time to buy.
  • Remove all emotion from your decisions about investing in the market and invest every month, no matter what is going on. We all wish we were investing in March 2009.

TAKEAWAY: My biggest takeaway is that there are so many resources available to help you get more comfortable with investing. If you haven’t found the right one yet, don’t be afraid to invest in one. Better investing practices truly pay dividends over time.

Random Three Questions

  1. What’s the best investment advice you’ve ever received?
  2. What is a show you like to binge watch?
  3. If this was your last night on earth, what is your final meal?

Connect with Amanda

Blog: Dumpster Dog 

Instagram: @dumpster.doggy

If you’d like to talk to my team at the Financial Gym to help you put together the pieces of your financial health puzzle, I hope you’ll reach out to us at the Financial Gym. My trainers love helping clients put together the puzzle, especially when it seems like the pieces don’t fit. The great news is that Martinis and Your Money listeners get 15% off Financial Gym services. So head over to, or send friends to, financialgym.com to get signed up today.