StartOut Blog

StartOut Investor Spotlights: Sam Sugarman and Fearless Fund

Sam Sugarman (he/him) is an Investor at Fearless Fund, a venture capital fund focused on pre-seed, seed, and series A-stage investments founded by women of color. In his role, Sam focuses on new investment opportunities, working with existing portfolio companies, and supporting Fearless Fund’s fundraising efforts. 

Sam spent two years in investment banking across the healthcare and restructuring sectors and two years in a private equity fund and co-investing at Hamilton Lane. Before these experiences, Sam completed venture capital and investment banking internships at Fortune 500 and startup technology companies. Sam attended Brandeis University and majored in Economics and Psychology.

As part of our Investor Focus series, Sam discussed his journey to VC and the pathway forward for underserved founders in 2023.

Sam, how did you get involved with Fearless Fund?

I started in the investment world with a limited partner and saw the whole landscape of the investment market. Early in my career, I was more interested in impacting and constantly seeking opportunities to help people.

I discovered Fearless Fund when the firm was relatively new on the scene and offered to help pro bono because I valued the mission immensely. I volunteered as a part-time analyst for a year before accepting a full-time position I’ve been in for over a year.

Could you tell me more about Fearless Fund’s beginnings? 

Of course! Fearless Fund was founded by two extraordinary women of color, Arian Simone and Ayana Parsons, in 2018. Both come from distinguished backgrounds; Arian has started multiple businesses, including brick & mortar and public relations companies. Ayana has worked with leading consumer companies, including P&G and Kimberly-Clark. Both partners have known each other for 20 years, and they’re incredibly invested in bettering their communities.

We fund everywhere, from pre-seed to Series A, and have invested in marketplaces, fintech, enterprise solutions, and more. We never want women of color to feel excluded because of their industry, and we offer an open door for all founders.

What’s best about working for an initiative-centric firm like Fearless Fund?

Seeing our impact on women of color entrepreneurs, a vastly underrecognized and undersupported sector of the startup ecosystem, is worth everything. We’ve had folks literally say that they wouldn’t have been able to get funding without Fearless Fund, which motivates me daily.

Aside from that, we’re focused on the community aspect of the founders we serve. We host a VC summit, an investor day, and a pitch competition, allowing us to get together and uplift the community.

My first VC summit was memorable because over 500 women of color came together to hear leading speakers. We believe in educating and providing holistic support for the founders, not just money.

How do you view the current state of VC investing in underrepresented founders, and where do you see it heading?

We’re posting an impact report about this very soon. As the funding environment tightens, we are particularly focused on making sure all underrepresented founders have access to financing opportunities, even if Fearless Fund is not the right investor. 

While we observed a positive trajectory in funding for underrepresented founders in 2020-2021, there needed to be a backstep in 2022. Many firms have continued to allocate capital to underrepresented founders, and JP Morgan, Amazon, Bank of America, and Mastercard have kept their word regardless of social or economic climate change.

I’d also like to give a shout-out to StartOut. I discovered the organization when looking for different accelerator opportunities for underserved founders, and I connected with some folks on the team. I say this without exaggeration, but the StartOut folks are some of the nicest people I’ve met in the startup world. I’ve never had a bad experience with anyone at the organization, and I’m in awe of the mission you lead and the founders you serve — big kudos to all the folks at StartOut.

You can connect with Sam on LinkedIn for the latest Fearless Fund updates and follow our Medium blog for more monthly stories.

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