Episode summary
How I Raised $10 Billion in Venture Capital
How I Invest With David Weisburd
· · 16 min · Hosts: David Weisburd · Guests: Scott Painter
Summary
Scott Painter says the $270 million take-private of TrueCar was the hardest capital raise of his career because it combined fundraising with defending a turnaround, explaining the plan, and doing it in a risk-off market with little appetite for risk. He says the deal took 21 months, required pitching a little over 150 investors per check writer, and nearly died a dozen times as lead backers backed out over tariffs, interest rates, and the auto market.
Painter argues that persistence mattered, but so did strategy and boundaries. He says he compartmentalized bad news, kept returning to pitch meetings, and eventually changed the dynamic by becoming willing to walk away. That shift, he says, ended the pattern of others pushing harder because he kept giving in.
He also frames the experience as personally expensive: he says he put $14 million of his own money at risk, borrowed from friends, mortgaged assets, and entered an 8-week intensive CBT program to stay sane. In the end, he says the transaction left him debt-free, more confident, and more aware of how much mental health pressure entrepreneurship can create.
Key takeaways
- Scott Painter says the TrueCar take-private required a little over 150 investor pitches per check writer and took almost a year and a half to close.
- Painter says investors were driven more by fear of missing out than greed, so he created momentum, scarcity, and deadlines to get checks written.
- He says the breakthrough came when he became willing to walk away, which changed how counterparties treated the deal within two to three days.
- Painter says he put $14 million of his own money at risk and even entered an 8-week intensive CBT program to stay functional.
- He says the transaction left him debt-free and more confident, but also underscores the mental health burden founders carry.
Notable quotes
“We ultimately had to pitch a little over 150 investors per check writer into the deal”
“The word persistence is invoked a lot more often than it really should be. And I also think it's highly highly underrated”
“I would compartmentalize that news. And I would go into my next set of pitch meetings”
“I had $14 million of my money out the [ __ ] window”
“You need to create momentum. You need to create scarcity. And you need to create a deadline”
How the episode opens
So Scott, you've raised over $10 billion with a B in venture capital throughout your career, and you just raised $270 million to take True Car private. You've said that's the most difficult money you've ever had to raise. Why is that?
Taking a company private is a whole combination of different skill sets. So it's not just fundraising to go build something. It's having to defend what's going wrong with what you're buying on top of then having a plan to turn it around and then showing a vision for the future.
And we happen to be just in a market that is very riskoff. There is not a lot of appetite for turnarounds. There's not a lot of capital that is flowing easily into any stage of venture.
So, it was both expensive. It was tricky. We ultimately had to pitch a little over 150 investors per check writer into the deal.
So, it took almost a year and a half to get it done. Ultimately, we did this with a syndicate of all strategic investors. We did not take a private equity lead.
We went down the private equity route almost seven times. every time we went down that route route it turned out that the terms were so awful for the team and the entrepreneur and the sponsor of this deal in this case me that it just wasn't worth the effort you end up breaking into prison.
So you took 21 months to do this raise in this riskoff market with all these different partners. Talk to me about the journey. How did that develop and what were your learnings through that journey? The word persistence is invoked a lot more often than it really should be. And I also think it's highly highly underrated.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- venture capital fundraising
- risk-off markets
- taking a company private
- investor skepticism
- entrepreneurial resilience
Companies and tickers mentioned
- TrueCar
Watch the episode
Watch “How I Raised $10 Billion in Venture Capital” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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How I Invest With David Weisburd, this episode and its artwork belong to David Weisburd. Octagon is not affiliated with the show; this page is an independent summary.
