Work Bravely with Sarah Sheehan


Work Bravely with Sarah Sheehan

This is the first Friday of March and March is Women’s History Month so I’ve decided to focus all of my podcasts this month on women and their accomplishments. At the Financial Gym, two words we hear all the time are fear and shame, and something I haven’t addressed on this podcast yet, or enough, is the shame founders have around their finances when building a business. So I was thrilled when Sarah Sheehan, Founder and Chief Customer Officer at Bravely told me she wanted to come on the show and speak about this specifically. She and I discuss how our finances shifted once we started actively pursuing our dreams and businesses and how we’ve combated the shame that comes with those finances. It’s a great conversation and I thank Sarah for giving me the opportunity to discuss this on the show.

What are we drinking?

Sarah — Prosecco

Shannon — Cristalino Cava

Podcast Notes

  • Sarah caught the start-up bug when she worked at the Gilt Groupe, prior to the New York tech scene taking off. It was exhilarating coming from Sirius and Coach Handbags and she was addicted to the adrenaline rush.
  • Bravely connects employees with professional coaches outside of work, so they can have better conversations and make their organization better as a whole.
  • Many employees will go to friends or family members with issues or questions about how to handle a situation at work and, although they are well-meaning, they are not equipped to answer the questions.
  • Sarah met her co-founder, Toby, at the Gilt Groupe.
  • Sarah previously worked in Human Resources and had to figure out how to retain talent and how to make the employees more engaged and produce healthier workplaces. At Gilt, she had the opportunity to do a complete career switch and launched their vertical of high end services, their answer to Groupon, called Gilt City. It grew really fast and over the next four years, Sarah became the head of sales. She realized how critical it was to attract and retain talent.
  • The idea for Bravely came from her co-founder referring his friend to her to help her with her situation. Toby was working on medical services on-demand and said what if they did that for HR services.
  • Sarah was consulting and left a year ago to pursue Bravely full-time.
  • When she became an entrepreneur, she felt a lot of financial stress. She could not pay herself what she was making inside a company. She is living in a financial state she has not seen in over a decade.
  • Shannon shared that she experienced the same thing when she started the Gym.
  • When starting a company, your finances are going to be a disaster.
  • Sarah always had a level of security with a regular paycheck and bonuses. Now her salary covers her rent and she lives off of her savings. When she evaluated how long her savings would last, her spending changed overnight. The hardest part is saying no to her friends.
  • Shannon said being an entrepreneur she is low on time and money. A year ago she had no money between herself and the Gym.
  • Sarah said that she understands her privilege being backed by venture capitalists and is grateful for this opportunity.
  • Shannon said when she started on her own, she wondered why she couldn’t be happy working a regular job like other people. She is honest with people that her finances are a mess, but she knows how to fix them.
  • A few weeks ago, Shannon made the decision to sell her house. She doesn’t know when she will be getting a salary increase, because she wants to hire more people and make enhancements at the Gym.
  • Sarah said she has never been happier than living this poor life. Shannon said she has never made less in her life, but she has never been happier. Believing in what you are building makes it all worthwhile.
  • People tend to spend more when they are unhappy at their job. Stress at work is all-consuming. You talk to your friends and family members about it and it has a ripple effect.
  • The people that Bravely works with cannot always walk away from the paycheck or the insurance.
  • Shannon said she didn’t get her finances on track, until she  realized she wanted to open her business.
  • Sarah said the silver-lining is that she realized she didn’t need expensive clothing or high-end trips. As her income grows, she will be able to continue to live frugally and she will be able to help other women find their path with the money she is not spending.
  • Shannon gives two different pieces of advice to people who want to start their own business:
    • At a bare minimum, you should have at least one year of salary saved up and readily available in cash. It always takes longer to build a company than what you expect.
    • If you feel passionate about what you are building, and cannot sleep at night, this is the other option.
  • Sarah said she didn’t really go through her finances well before starting her company, but she knew she had enough to supplement her salary for a while.
  • Shannon said there is no shame in not having a lot of money when you are starting a business.
  • You need to have a high tolerance for risk. When you are doing this as a single woman, it is even riskier.
  • What’s the worst that could happen? Everything is fixable. Focus on each day.
  • It is difficult to stay healthy, when you are working seven days a week. You must have an outlet to stay sane. Shannon uses a Peleton bike about four times a week.

TAKEAWAY: Remember that starting a business will have a lot of negative repercussions on your personal finances; however, if you’re truly passionate about the path to your dreams, you will find a way to make it work no matter what.

Random Three Questions 

  1. If you were to build another business, what would it be?
  2. What is a show you like to binge watch?
  3. What is a place on your bucket list that you’ve never been to?

Connect with Sarah



If you want to make some of your dreams a reality and need someone to help you along the way, I hope you’ll reach out to my team at the Financial Gym. We have clients achieving their dreams every day that they never could have realized on their own. You can schedule a free call here to find out more. No matter where you are in your financial journey, my financial trainers can help you get where you want to go. So head over to or send friends to to sign up today!


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