Angel Investing with Diane Henry


Angel Investing with Diane Henry

In honor of Women’s History month in March, I’m focusing all of my podcasts this month on women and their accomplishments; and I’m so excited to share today’s guest with you. I met Diane Henry last year when my lead investor in the Financial Gym sent out an email about why investors should invest in my company and Diane responded almost immediately. Diane built a successful business in the male-dominated world of commercial real estate, to the point where she is now able to invest in other businesses, and one of her portfolio companies is actually the Financial Gym. Diane joins me today to share her story and her approach to angel investing and how she picks the businesses she invests in.

What are we drinking?

Diane — Coffee

Shannon — Champagne

Podcast Notes

  • Diane had always been interested in starting her own business. She saw a hole in the commercial real estate market and knew she could fill it. People were not trusting the people who were supposed to be helping them.
  • Diane and Shannon talk about working in male-dominated fields and the heightened sensitivity about everything gender related.
  • When Diane first started out on her own, she had a lone-wolf mentality, where it was her against the world with her team behind her. She didn’t have a lot of sponsorship or mentors. She now recognizes that mentality was not necessary and realizes the importance of having a mentor.
  • Diane is an angel investor to founders in the early stages of businesses. She finds it to be an incredible experience to be an advisor to new entrepreneurs.
  • Diane invests through Rogue Capital Collective and now has many investors that feed knowledge and experience into the collective.
  • An angel investor is expecting a future financial return – it’s not free money or a grant.
  • Every angel investor is different. Diane only invests in venture scaleable businesses, meaning a business that can go national or global and can reach millions of customers. She also looks for the founder. Why are they doing this? Why are they credible to do what they are doing?
  • Diane shared an example of a male founder that was pitching a product for women and it was only men on his team. What you are building, and the founding team, should make sense.
  • Diane is an investor in the Financial Gym. In their initial conversations, Shannon loved the way Diane made her think about her business.
  • The size of an angel check is based on how established the business is. It is ultimately about the founder and if Diane can believe in what they are doing. If risk and reward are proportionate, then she is willing to invest. If everybody else is chasing after a business, it drives the price up.
  • If you can’t sleep at night, because you are so passionate about your business idea, you will be able to ride the ups and down of being an entrepreneur.
  • Last week, Shannon had her first Series A conversation and explained that the first two years of going on her own, she still thought she could just go back to the bank if it didn’t work out. After she received her first investor check, she went all in and didn’t look back.
  • This year, Diane started to share more of her views and strategies through her website and Twitter.
  • Diane continues to invest in founders of all types. Her portfolio is diverse, because her network is diverse. She is trying to scale up her advisement work. She just did the .25 Initiative, which is a great way for founders to get people on their board. She is always analyzing the market to see where future opportunities may come from.
  • Diane invites partnerships for investing, instead of being a lone wolf.
  • Being an entrepreneur is intense. It can’t just be a desire for the money – there has to be something to make it worth it and keep you coming back. The money cannot be the only reason. The road to the top is winding and you need to have a strong stomach.

TAKEAWAY: Remember that there are numerous lenses in which we can view people and to check yourself before you filter everything through a gender lens. As Diane said, Women’s history month is about more than accomplishments for women is about equality for all.

Random Three Questions 

  1. What is a book that has inspired you?
  2. What is a show you love to binge watch?
  3. What do you do to relax?

Connect with Diane

Twitter: @investordiane

If you need someone to help make money fun, 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!


Previous articleGet Money with Kristin Wong
Next articleWomen Who Inspire with the Happy Hour Ladies
Shannon is a financial planner who left a “traditional” financial services firm to start her own company, The Financial Gym, because she felt traditional financial services firms did not have the tools or resources to help people in their 20s and 30s who are starting out and trying to build assets while also managing debt. She realized that the key to long-term personal financial success is a commitment to financial fitness and making smart financial choices. Through her blog, Financially Blonde, her book, Train Your Way To Financial Fitness, her podcast, Martinis and Your Money and The Financial Gym, Shannon is committed to making financial fitness fun, easy and accessible for everyone.

Leave a Reply