E345: How I Raised $10 Billion in Venture Capital w/Scott Painter

What does it take to raise $270 million in a risk-off market while keeping your personal life, sanity, and team intact? In this episode, I sit down with Scott Painter, Founder & CEO, TrueCar, to unpack the 21-month journey of taking a company private. Scott shares how persistence, strategic thinking, and mental resilience allowed him to navigate investor skepticism, market volatility, and personal stakes. He discusses the lessons he learned from fundraising in both up and down markets, why creating momentum and scarcity is critical, and how setting boundaries transformed the outcome for him and his team.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00David Weisburd?

  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 TrueCar private. You've said that's the most difficult money you've ever had to raise. Why is that?

• 0:10Speaker 01

  Taking the 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 risk off. 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.

• 0:54Speaker 01

  We went down the private equity route almost seven times. Every time we went down that 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.

• 1:09David Weisburd?

  So you took 21 months to do this raise in this risk off market with all these different partners. Talk to me about the journey. How did that develop? And what were your learnings through that journey?

• 1:19Speaker 01

  The word persistence is invoked a lot more often than it really should be. And I also think it's highly, highly underrated. Man, this was the hardest thing I've ever done. It fell apart a dozen times. If I look back at the different chapters of this, nothing about this transaction and how we started looks like how we finished, other than me and my core team. We came in and we, we thought we had this thing done and in the bag at least a dozen times. And when I say in the bag, I mean, ready to get down to the merger agreement, wiring money. We had firm commitments and we had to blow. And when it fell apart, it did not fall apart a little bit.

• 2:00Speaker 01

  We, I mean, our lead investor a dozen times completely backed out based on one thing or another. The, you know, the auto industry, interest rates, tariffs. This has been the most volatile backdrop. That you could be raising money in as well. So it wasn't just a risk off market. The auto market in particular, when hit with tariffs, the level of risk that almost anybody, and it wasn't just venture capital. I'm talking to venture capitalists, private equity funds, high net worth individuals and strategics. Everything along the way backed out, said, no, it's not going to happen. Anytime you are selling a turnaround, there's a, there's another layer of skepticism that I had not anticipated. You know, I tend to be a fatally optimistic entrepreneur.

• 2:43Speaker 01

  I believe that what I can do is based on things I've done before. It's sort of putting like putting on your pants. You just feel like I can do this. The level of, you know, commitment to this process, for me to get up at six in the morning and hear somebody say on a Monday or a Wednesday, we've reevaluated, I think we're out, is so devastating. And the level of, I think, risk I had to take here was amplified by the fact that at one point we had almost 35 people that were now on my personal payroll as sponsor to keep this thing going because you have to have the tax advisors. You have got, you know, so you've got P W C, you've got your law firm. You've got a whole bunch of professionals that are coming to standing meetings

• 3:28Speaker 01

  and the clock is ticking at $10,000 an hour when you start looking around the room. It is really not, I think, an activity that a solo individual sponsor takes on. It is something much more well suited to a large private equity fund. It's exactly why they tend to be the typical take private candidate and not founders.

• 3:48David Weisburd?

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• 5:14David Weisburd?

  alongside filings, broker research, news, and more than 240,000 expert call transcripts, turning raw conversations into comparable, auditable insight. Take advantage of AlphaSense AI-led expert calls now. The first to see wins, the rest follow. Learn more at alpha-sense.com/howainvest. As I go deeper and deeper into fundraising and interviewing exceptional people such as yourself who have raised $10 billion in venture capital, a lot of it does seem to rely on these momentum games. And oftentimes fundraising is a momentum game, whether it's finding the anchor for a company, finding the anchor for a fund. But you were able to close this with losing a lot of momentum along the way.

• 5:56David Weisburd?

  How did you break this cycle of the deal almost dying and then getting buy-in from the market to back you multiple times?

• 6:03Speaker 01

  Entrepreneurs aren't just special. They are the glue that keeps these types of things kept together. When I would get the bad news, I never would share it until I at least sat on the bad news for 24 hours. And I mean, I would get devastating news and I knew people were waiting for the next meeting to hear I would compartmentalize that news and I would go into my next set of pitch meetings. And it was almost always the case that it was in that compartmentalization moment that you could begin to ideate and think about how you're going to solve this. Use it as not just information, but also as power for how you're going to solve the problem because you clearly haven't gotten there yet. Keeping my team motivated was a very, very cagey thing to keep all of them coming through.

• 6:48Speaker 01

  I got to the point where in addition to this, I got married last year. So I entered my third marriage. I was putting every penny I had in terms of personal access to capital and my leverageable capital into this deal. I ultimately had to borrow money from friends to be able to pay for the wedding and keep things floating. I went as deep as you can go, mortgaged quite literally everything I had to be able to get through last year and pull everything off. Ultimately, for me, getting married in April landed me somewhere in September around Burning Man, wondering what the fuck am I doing? There's that famous looking into the abyss and chewing on broken glass.

• 7:32Speaker 01

  I mean, that was the moment where you look over at your new wife and just say, I don't even have an answer for you on when we're going to get paid, but we're definitely not taking any trips. We're definitely not going. I mean, if we have to, if I have to go to Las Vegas for a meeting, I'm flying Southwest in convenient times. I mean, it was just that real. And I ultimately was not a pleasant person to be around. And she said, you know what? I know it doesn't seem like now's the right time, but if you do the same things, you're going to get the same result. Would you consider going into CBT, cognitive behavioral therapy? And I entered an eight-week intensive CBT program in addition to fundraising that I

• 8:14Speaker 01

  was doing in the afternoons for eight weeks, just to keep sane. I mean, I really had to have somebody check me.

• 8:23Speaker 01

  Is this wise? And of course, you have all of those similar conversations like, okay, if this fails, what am I gonna actually do? And so I have to spend at least a double-digit percentage of my day thinking about new companies. I'm not somebody who's ever gonna just simply go to work for somebody else. So for me, it was, okay, if this fails, I'm gonna be getting out of automotive. I'm gonna be going into something AI related. And I was literally working on business plans in the late nights about what I'm gonna be doing next and talking to people and formulating those ideas. I emerged out of that CBT training, recognizing some things about just me as a human that had never, my attachment theories weren't strong as a kid.

• 9:03Speaker 01

  My dad was somebody who left me only with one gift in life, a chip on my shoulder that drives me. And he just was not available. And I've also got four kids. And so I ultimately changed course in terms of the energy that I was applying, but I had to create new boundaries. And everybody in the transaction for the first year and I would say eight months, knew that I wanted this so bad that I didn't see that I was getting worked, that they had the power, because even though I was right about everything, and even though I was passionate about everything, and even though I laid out a great opportunity, they felt they could take more because I would give it. And that was what changed in me.

• 9:45Speaker 01

  And it took that eight-week CBT therapy where I came back and I just said, you know what? I'm now willing to walk away. And it was honestly like having a completely new sort of spine where I, and everybody felt it. It literally changed within a two to three day period. I just said, you know what? We are at the end. It makes no more fucking sense. This is how it's gonna roll. And as soon as I did that, everything started snapping into place. And more importantly than just snapping into place, people who had factually betrayed me along the way.

• 10:19Speaker 01

  Started coming back in and I was able to compartmentalize them and put them off to the side and navigate them and put them in places where they could no longer affect the overall transaction. That, I think, was the real inflection point in the deal.

• 10:32David Weisburd?

  That's so fascinating. Sometimes these negotiations, in your case, it was 21 months. Sometimes people could be so anchored in their positions, 20 months and 30 days, and then in the last day, they can move by 50%. Once you really give them a true binary choice. I think about this heroic trade. You essentially made this heroic trade. It wasn't quite a trade in that you bet on a stock. It was a fundraiser. And when I've interviewed people like Cliff Asness from AQR, who struggled when value was out of favor, or like Bill Brown, who did the big short trade within the Stern family office, one of the things that the greats really keep on doing is they're not just arbitrarily holding their position. They're saying, I'm all in no matter what. They're constantly reevaluating your priors. In your case, you had to keep on asking yourself, is this boldness or is this lunacy?

• 11:15David Weisburd?

  Am I doing this because it's the right thing and other people can't see it? Or B, have I completely lost my mind? And sometimes those barriers are extremely thin. Sometimes it's a very thin walk between being contrarian and right and just being completely crazy.

• 11:29Speaker 01

  I'm an entrepreneur. I invest my time. I invest my reputation. I invest my insight into these businesses. So to me, it's the same thing. But in this particular case, I can tell you, I had $14 million of my money out the fucking window. I mean, I was barely able to keep everything together. Now, in the end of this transaction, we ended up buying the company. I think we stole the company. This is a business that does $175 million of top line revenue with six or seven million unique monthly shoppers coming to buy a car, and we have a network of 11,500 dealers across the country that pay us a monthly fee to be on that program.

• 11:59David Weisburd?

  I want to go back to this concept of persistence. You're very close with Elon Musk. You're kind enough to invite me to Thanksgiving with him, and you've really got to observe him from close up. Has his persistence rubbed off on you? Or is it just completely unrelated to your ability to persist through these difficult times?

• 12:14Speaker 01

  He's got persistence that would be hard to really describe.

• 12:19Speaker 01

  I think he and I relate because we're both persistent humans, definitely persistent. And I think I'm probably persistent to a fault in a way that almost nobody I know, but he is next level. I mean, it's not even persistence with him. It is, there is no alternative. I mean, he sees the path forward and there's nothing that's going to get in his way. I mean, there's, you know, two ways to think of it. Either you're an unstoppable force or you're an immovable object. In many cases, he is both. And so I think that he's a unique case. Persistence would not sufficiently describe what he is.

• 12:55David Weisburd?

  You've also raised $10 billion outside of this transaction, which is probably one of a dozen people on planet Earth could say that in the venture space. What have been some of the learnings from raising venture capital in both down and up markets?

• 13:09Speaker 01

  I don't measure it in how much money I've raised. That's much more of a banker type point of view. I've had 127 closings. I think closings, whether you're closing a million dollars or $10 million or $100 million, it's pretty much the same thing. You've got to understand why people write checks. One of the things I've learned, for example, is people do not write checks for the most part because they are greedy. They write checks because they don't want to miss out. Fear is by far a more powerful marketing motivator. It is exactly the same thing in fundraising. You need to create momentum. You need to create scarcity and you need to create a deadline. But being able to take money is about creating urgency around a moment where if you don't write the check, you lose the opportunity altogether.

• 13:54Speaker 01

  And you have to be strong enough to say that and really set that framework up.

• 13:57David Weisburd?

  There's this cliche that sometimes the most difficult things in life really make you stronger. Over the last 21 months, you've gone through this process. It threatened your marriage. It threatened you as a human being. Do you regret? Are you thankful for that 21 months? Or is it just something that you had to get through and it was a huge pain in the ass? And did it make you more anti-fragile?

• 14:18Speaker 01

  I certainly am more confident of what I'm capable of. I am a much more pleasant human at the moment. When you're under financial stress and it's existential, you're getting up every morning, whether, you know, trying to figure out what do you have to do to survive the day, the week, the month? That kind of pressure is the pressure that kills you. I'm now on the other side of that where I've paid off all my debts. I paid off my mortgages. I am debt free again, and I am now in a place where I can take a breath and say, you know what? I did that. And it is, it is extremely gratifying to have done that. And to also see the benefits of how that's now affected my relationship with my wife, my children. I mean, everything around me has taken a turn because it reflects.

• 15:02Speaker 01

  We don't talk enough about the mental health issues facing entrepreneurs. I don't think anybody could be possibly prepared for it. I wrote about it in Inc. Magazine, sort of the, you know, the dark side of being an entrepreneur. It is a real thing, the, the level of depression that you have to compartmentalize in order to do what you do in this case. You know, a lot of people ask me, you know, what does it really mean to be an entrepreneur? I mean, and I meet a lot of people who say they're entrepreneurial or entrepreneurs, or they're running these companies. Tell you what, you know, you're the entrepreneur when you look over at your wife and you just say, we're not getting paid for a minute. That we're not taking a trip. We got to sell this asset. I gotta, I gotta get rid of that car that I've always loved. I put all, I have three properties here in Los Angeles, two homes.

• 15:45Speaker 01

  I put everything on the market and I didn't just put it on the market. I had people running through my homes and looking through my drawers and looking through everything. And my wife said, what are we doing? We're selling. I said, it's just stuff. I need to know what resources I have. And, and I literally went, and I mean, everybody in my life saw that. I mean, all my homes were on the listing services and listing sites. And everybody who came, you know, across my, my life said, oh, I see everything's for sale. Is everything okay? I said, sure, everything's fine. I was just thinking about selling my house, but, and you know, and then in the middle of this, we had the Palisades fire. I almost lost another home. It was just absolute chaos. And so the ability to have survived something like that, it, it certainly changes you and it certainly gives you the ability.

• 16:30Speaker 01

  And, and I guess this is where, you know, a guy like Elon really does get it because the things he has seen are superhuman. I mean, he's lived one of the most extraordinary, unique lives to have survived these things and to get where he is, almost makes him untouchable. I mean, it, it would be hard to rattle me at this point, but I'm sure if I took any, if I took any of the kind of risk or leverage that he does, does to do what he does, I'm sure it would rattle me. In addition to being the richest man in the world, he has the largest debt facility of any human has ever had of all time. I mean, he is not. Without risk, even given who he is, massive risk.

• 17:06David Weisburd?

  Scott, I have to be honest, I was in the camp, I thought you were chasing a ghost and out of your mind through this process, I was watching from the sidelines, I was rooting for you, but I thought you had lost your mind and now have to make a new rule. Peter Thiel has this rule, don't bet against Elon Musk. My new rule is don't bet against Copinger. So, congrats on putting it all together and thanks so much for sharing your journey.

• 17:27Speaker 01

  David, thanks for having me. It's good to see you again and hopefully next time we talk, I'll tell you that we've turned around the product and we are raising money at pennies on the dollar.

• 17:36David Weisburd?

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