Bessemer Venture Partners’ Jeremy Levine is someone who keeps his head when others are losing theirs.

He’s long been wary of tech exuberance while being a long-term optimist about the transformative power of technology.

A board member at Pinterest and Shopify, Levine described his investing style to me for this week’s Dead Cat podcast: “I don’t like to go where all the cool kids are, where all the popular kids are. I like to kind of go off in the corner of the playground and find someone who’s doing something over there that’s really compelling that most people are prepared to dismiss or aren’t that excited about.”

I wanted to have Levine on the podcast to explain the tech downturn. Levine has been investing at Bessemer for over two decades. I wondered, how does this moment compare to the dot-com bust and the Great Recession? On the podcast, Levine traces the ebbs and flows of tech euphoria while giving concrete math to the pain of down rounds.

‘The entire world smoked a giant joint and was high as a kite’

He delivered quite the diatribe when I asked him to compare the present moment to the dot-com bust:

When I joined the venture industry in 2001, I looked at these entrepreneurs who built businesses and these venture capitalists who funded them from ’96 to 2000 and I was jealous. Oh my lord, they generated enormous value and enormous wealth in such a short time. And I said to myself, the world is never going to get this crazy again. The entire world smoked a giant joint and was high as a kite, and what fun it would have been to be part of that, but I missed the party. But I thought, you know, it’s really rewarding and fun and challenging to find compelling entrepreneurs and invest in startups. So even though it’s never gonna get as good as it was in 2000 again, I’m going to try to make this my career because I think I’ll find it fun.

And lo and behold, 20 years later, it happened again: Someone passed the joint around the party a second time, and no one remembered what happened the first time, and things got crazy. So in that sense, it’s really similar. Enormous wealth was created, enormous companies were created. But the difference is that when that party ended — at the end of 2021 — it wasn’t three or four companies left standing. It was dozens and dozens of strong public companies, and hundreds of really interesting private companies. Now, not every unicorn and not every company that raised a lot of money will be successful. But the industry is, I would say, two orders of magnitude larger than it was in 2000.

He argued that he believed there was still “another shoe to drop” in this tech downturn. He said venture firms were reserving more money to make follow-on investments for their existing portfolio companies, giving them less dry powder with which to make new investments. “I think we’re in a little bit of that spiral,” Levine said.

The Anti-Portfolio

Back in July 2021, amidst the final heady months of the bull market, I profiled Bessemer and Levine in an in-depth story titled, The Anti-Portfolio. (Still worth a read if you missed it.) An undercurrent in the piece was that Bessemer had smartly invested early in some of the tech industry’s most popular public stocks like Shopify and Twilio but that the firm had sold down its positions before a massive run-up in their value on the public markets. Now, with Twilio down 70% and Shopify down 52% over the past 12 months, Bessemer’s decision to cash in its winners seems more rational.

I asked Levine whether he felt vindicated.

“We’ve made every mistake possible,” he told me. “But we’ve also gotten some things right. And so with the benefit of hindsight, we distributed our stock in Shopify way too early. And at the same time, we held onto some stocks in 2021 a bit too long. I think we’re not all that focused on getting that exactly right. Of course, we’re always trying to do better. But the real win, if you will, and the excitement and what motivates us is to invest in a company like Shopify or Auth0 when it’s really small and to nurture it and help that company become really big. And if you manage to top tick and exit your position … all the power to you. That’s just not that interesting of a game.”

Give it a listen

Read the automated transcript

P.S. If you want to weigh in as to whether I should rename the podcast, you can vote on Twitter or voice your opinion in the comments.

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Another Shoe to Drop (w/Jeremy Levine)

The Cerebral Valley Podcast