#4 - Lies Founders Are Told And The Founder-Funding Disconnect - Tessa Flippin of Capitalize VC

RBFN Podcast

It’s an insightful episode this week while we welcome Tessa Flippin, Founder of Capitalize VC, as she shares her journey from startup founder into the world of alternative capital funding. Tessa describes the unique approach and deal structure of Capitalize VC, which enables her to do more deals than typical VC, and to support diverse founders. Along the way, Tessa shares what it’s like to raise a fund as a black woman, gives practical advice for those looking to get into the world of alternative capital investing and VC, and shares her perspective on why starting a company is more challenging than starting a fund.

Key Takeaways

[4:21] At TechNexus Tessa started investing in seed-stage enterprise technology companies and learning the ropes of being an investor on the other side of the table.

[4:44] The reason Tessa wanted to be a founder was to make an impact, particularly on underserved and diverse communities globally.

[6:02] Tessa talks about working to bring more diverse LPs to the table who haven't invested in alternative capital and venture capital funds before, capitalizing on their involvement, and how that will build generational wealth for diverse investors.

[8:38] Tessa discusses figuring out how to run an alternative capital and venture fund, and how her previous experience helped her. When Tessa decided to launch her own fund, she had the tools and knowledge from TechNexus, which accelerated the process.

[13:00] Why starting a company is harder than starting a fund, from Tessa’s perspective.

[17:01] From her experience as a founder, Tessa instills valuable lessons to the founders she funds at Capitalize VC

[19:50] At Capitalize, they focus on the intersection of e-commerce, infrastructure, and consumer brands, investing in both sides of the e-commerce equation.

[23:04] Tessa talks about the deal structure, including the way they structure their RBF deals, and how they choose between structures.

[28:40] Revenue-Based Financing fills the funding gap and benefits both sides of the equation.

[38:42] Tessa discusses where they find their deals geographically and the decision to work in markets outside of major tech hubs.

[40:52] Tessa’s mission is to increase access to capital and invest in diverse founders. Here’s what she looks for in a company.

[42:04] How are entrepreneurs doing in this rapidly (and often weirdly) shifting world?

[47:07] Who does Tessa admire both on the FinTech and alternative capital funding side?

[50:04] Tessa gives her prediction for what will happen over the next 3-5 years for founders like those she’s working with today.

[55:02] What are the biggest lies that most founders are typically being fed?

Resources:
RBF Network

Novel Capital

Twitter: @RBF_Network | Keith Harrington

Guest:

Tessa: LinkedIn | Twitter

Capitalize VC