Fixing the Capital Stack with Cheryl Kellond

Cheryl Kellond is a powerhouse 2x Founder, 3x Ironman, and 4x Mom who has generated over $750M in revenue from innovative health-tech, SaaS, hardware, and media products for startups and leading brands. Her most recent venture, Apostrophe, achieved nearly $10M ARR in just two years before being acquired by Centivo in June 2021. As the only B-Corp certified health plan in the US and a Techstars '17 company, Apostrophe's success was no surprise, given Cheryl's expertise in concept-to-launch.

Cheryl's first company, Bia Sport (Lemnos'12), was a top Kickstarter project and the #1 rated fitness wearable on Amazon, solidifying her spot as a leading figure in the industry. She holds an MBA from MIT Sloan, a BA from The University of Chicago, and has been featured in prestigious publications such as Inc. Magazine and The Wall Street Journal. Additionally, she was voted Denver's Most Admired CEO and selected for the inaugural 40 over 40, cementing her place as a trailblazer.

Cheryl's endless energy for thrilling customers, building great teams, firing up female badassery, and breaking barriers has led her to work on exciting new projects at the intersection of her passions and superpowers, including women, health, community, and technology. Currently, she is a cofounder at Play Money Studios, where she is revolutionizing early-stage capital. She is also an EIR for the DE&I Founder Catalyst Program at Techstars and an Angel Squad Member at Hustle Fund. Her previous roles include CEO and Co-founder of both Apostrophe and Bia Sport and product leadership roles at Yahoo, Adobe, and ETRADE.

Eve #wealthwednesday Highlight 81: Cheryl Kellond, Co-Founder - Playmoney Studios

What was your first-ever investment?

My first investment was in myself, with my first startup.  I left a high-paying job in big tech – despite being 40 years old and in my peak earning years, I left a high-paying job in big tech to start a sports watch company. Despite having four children, including one in college, I was determined to build this company and become a founder. This was my most significant investment in the company and my personal growth and development. It may not have been the smartest move, but I have no regrets.

I am fortunate to have chosen the right life partner who is patient and supportive. My spouse has a steady job, which has given me the flexibility to pursue my entrepreneurial dreams. I acknowledge this is a privilege that many do not have, and I am grateful for it.

How and why did you get into the space of Angel Investing? 

As someone who has experience founding a company, I am familiar with the challenges that come with it. Through both successes and mistakes, I have acquired a pile of knowledge through both successes and mistakes, and I want to share it. Female-founded VC-backed companies are still limited, and I will do everything I can to help make their path easier than mine. However, mentoring is not enough. Female founders are underfunded and need capital.

Beyond deal flow, I also joined Hustle Fund Angel Squad to better understand how investors view startups. It’s helped me become a better mentor and improve my skills as a founder. 

What role do you play in the wealth space? Why is it important to talk about mobilizing more money and why this isn’t happening?

I have always been involved in the wealth space for women since my Big Tech years at Yahoo. I had a 70-person team and was attracting the highest-performing early- and mid-career women from across the org. One of my biggest accomplishments was adjusting salary parity across the team. It was a massive effort because the discrepancies between the men and women I recruited were over 20%-30%. At my last startup, we had a pipeline of talented women coming into entry-level jobs. We focused on identifying and promoting talks and building skills. One of the biggest returns I got from that startup journey was seeing how many have gone on to really amazing careers. True sponsorship and action on pay parity is an essential first step in creating wealth.

When discussing female founders needing more funding, there is so much low-lying opportunity for alpha-level returns. However, people often approach this as a social impact gap that needs to be bridged rather than the fantastic investment opportunity that it is. By investing in founders solving big problem spaces, we can make a significant profit while supporting the things we want to be solved. We, women, should take advantage of this asymmetrical opportunity to invest. 

What is the most exciting thing you’ve learned that you would want others to know as you've gone on this journey to discovering why there's this issue and how you're gonna solve it?

The most valuable lesson I've learned on my journey is that I no longer feel the need to prove myself or gain approval from others. This allows me to operate from a place of generosity, exploration, and abundance. Sometimes, I wish I had come to this realization earlier in my 30s or even my 40s. Try not to worry excessively or be overly self-critical. Trust your instincts and have confidence in your decisions. Do not allow anyone to condescend to or patronize you.

Is there a person or a company that’s really inspired you? And why?

I am a huge Elizabeth Yin fan girl. She operates off generosity, experimentation, and abundance better than anyone else. And you can see it paying dividends to the whole ecosystem. 

Additionally, I have developed a newfound appreciation for Sofia Amoruso and her new Trust Fund. I am girl-crushing a bit. She’s been fearless in defending her reputation with a no F’s to give vibe, and I like how she is working to democratize access to her fund as much as possible. 

What advice do you have for someone getting started?

As a founder, the key to success is creating a product that people love and that generates revenue. Venture capital is an asset class. But founders too often see it as a value judgment of their worth. It's important to build the business you want to see and not let this mindset affect your thinking.

New businesses need capitalization, and most people cannot simply quit their job and hope their partner can support the family. Early-stage capital formation options are critical and pretending institutional VC is a one-size fits all product is not going to work. We’ve been doing a lot of thinking about this and will be testing our theses soon at my new venture Play Money!

How can we stay in touch?

I am on Twitter (@XXfounder)

Our website is We will be accepting applications for season 1 starting in Q2. While I haven't shared many details about the project yet, it's essentially an opportunity for individuals to build their dream startup portfolio and invest alongside the most promising early-stage fund managers. The minimum investment is $500 a month, which is your annual IRA contribution.

Our target audience is late millennials and early GenX. High income. Maxing out retirement savings. They might have kids or busy jobs, leaving them with limited time and access to make angel investing a full-time hobby. But they want the financial upside of the asset class and have a fire about supporting founders and innovation.

Have thoughts on this week’s topic or question for me or Cheryl? Post your thoughts in the comment section. Until next week.🙂

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DISCLAIMER: The thoughts and views expressed in this video do not constitute financial or investment advice.

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