VCs chased crypto and passed on his “boring” startup—then he raised $385M at a $2B valuation. | Aaron Schumm, Founder & CEO of Vestwell

Aaron started Vestwell in 2016. Two years in, he had $500K in ARR and an investor asking if it would ever make money. During the 2021 bull market, VCs told him 401ks were too boring—they were busy chasing crypto. Then Morgan Stanley signed. Today Vestwell has 2.5 million people saving on the platform, over $200M in ARR, and just raised $385M at a $2B valuation.

In this episode, Aaron breaks down why he white-labeled everything instead of building his own brand, how losing the JP Morgan bid as a 40-person startup still turned into one of his largest partnerships, and how a methodical cap table let him raise a Series A on a couple hundred thousand in revenue.

Why You Should Listen

• Why letting your customers keep their brand beats competing with them.
• How to raise a Series A with only a few hundred thousand in ARR.
• Why losing an enterprise deal is the start of the sale, not the end.
• Why you never regret firing someone too soon.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Vestwell, Aaron Schumm, fintech, 401k, retirement savings, enterprise sales, channel partnerships, white label software, Series A fundraising, Morgan Stanley

Chapters

• 00:00:00 Intro
• 00:02:05 The Morgan Stanley Deal That Proved PMF
• 00:08:32 A 401k So Bad It Started a Company
• 00:10:23 Building V1 in a Regulated Industry
• 00:17:07 Turning Advisors Into a Sales Channel
• 00:23:57 Raising an A on $200K of Revenue
• 00:31:16 Too Boring for the Crypto Bull Market
• 00:38:45 Losing JP Morgan, Then Winning It Back
• 00:43:23 Never Regret Firing Too Soon