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Jeff Lieberman

Managing Director, Insight Partners · 1 appearance on the record, plus 1 compilation re-air.

computed by AI from the episodes · how this works → · full disclaimer →

investor

Jeff Lieberman is a Managing Director at Insight Partners, where he has worked for over 24 years. He has led investments in companies including Qualtrics, DeliveryHero, HelloFresh, and Udemy.

19statements → 3claims → 2claims resolved → 4.06/5average certainty → 2/5average debate potential → ≈4.0/5argument clarity, estimated → 8said about them ↓

2 supported 0 partly supported 0 contradicted 1 not checkable as stated how the 3 claims stand · each chip opens the sources

1 prediction · 2 assertions · 12 insights · 3 disclosures · 1 what if · every statement was checked. The prediction and assertions are the 3 claims: statements the public record can support or contradict. 2 are resolved, and 1 names no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Jeff argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Prediction Held up
Lieberman: VC industry's 50% returns are ridiculous, unsustainable, and will mean revert
“50% returns I read this weekend across the industry. Like, as an industry, that's ridiculous. Massively unsustainable. We're not all that smart. We're not all that good, including myself. It's not possible. So there's clearly something going on, and there'll b…”
Jeff Lieberman Mar 28, 2022 ▶ 10:27 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff

Expressed certainty vs assessment result

none yet certainty 1
none yet certainty 2
100% certainty 3
100% certainty 4
100% certainty 5

weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet

How they sound: speaking style how? →

299 words/min while actually speaking · 0.9 um and uh per 1k words

No argument clarity score for Jeff Lieberman: no usable question→answer exchanges on raw tape (a fair score needs 8+). We do not score a sample that small. Roundtable and news formats yield far fewer direct exchanges than interviews. Their coarse estimate from 23 exchanges on the produced feed is ≈4.0/5, shown at half point precision because the sample is small and produced tape scores higher.

Measured by listening to 6,491 words across 1 episode, but every recording we have of Jeff Lieberman is the aired feed, and an editor cleaned that audio before release. Some of the hesitation was cut before we ever heard it, so read these as floors: the true rates are at least this high. These are measurements of speaking style, not scores. How it's measured →

How the interview went all their pushback → series average →

Across 2 rated episodes:

host pushback ▾ 2/10
pushed back at the host 1.5/10
setup questions received 73%

Everything Jeff Lieberman said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

Prediction Held up
Lieberman: VC industry's 50% returns are ridiculous, unsustainable, and will mean revert
“50% returns I read this weekend across the industry. Like, as an industry, that's ridiculous. Massively unsustainable. We're not all that smart. We're not all that good, including myself. It's not possible. So there's clearly something going on, and there'll b…”
Jeff Lieberman Mar 28, 2022 ▶ 10:27 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Insight
Lieberman: Entry price does not matter long-term for truly great companies
“If you own the ones that are really good long-term, I don't think the price overly matters. Your returns will be worse if things correct, but they're still going to be good. And if things don't correct, your returns will be spectacular. But if you own the bad …”
Jeff Lieberman Mar 28, 2022 ▶ 16:35 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Insight
Lieberman: Command-and-Control Venture Capital Firms Will Become Outdated
“In a world that's decentralized, in a world that's global, in a world that's innovating very quickly, you need to hire super, super smart, super energetic, super passionate, inquisitive people to go find really interesting stuff, and if it's command and contro…”
Jeff Lieberman Mar 28, 2022 ▶ 18:30 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Insight
Lieberman: Business Classrooms Don't Work for Venture Capital Training
“I would argue in our business, and in most business, classrooms don't work. I mean, I took marketing classes. You know, most business classes aren't practical relative to what it is to be a VC.”
Jeff Lieberman Mar 28, 2022 ▶ 19:05 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Assertion Supported
Lieberman: Insight Partners analysts have full control over senior partners' calendars
“When an analyst joins Insight, they basically have full cart, blanche control of senior partners' calendars, and what I mean by that is if an analyst walks into my office and says, Jeff, I got this really cool company. I want you to talk to them tomorrow. I ta…”
Jeff Lieberman Mar 28, 2022 ▶ 20:49 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Insight
Lieberman: Hot markets compress price spreads between great and average assets
“I think in times like this, we typically average assets get priced way up. Great assets get priced up, but the spread between those assets Probably compresses.”
Jeff Lieberman Aug 12, 2022 ▶ 15:16 20VC: 13 of the Great Investing Minds on When to Pay Up vs When To Remain Disciplined and Walk Because the Price is too High: The Ultimate Guide to Price Sensitivity
Insight
Lieberman: Entrepreneurship is a process, not an epiphany
“I didn't realize, really because of my upbringing, that entrepreneurship was a process, not an epiphany, and it's something that I just never really had thought about or was exposed to.”
Jeff Lieberman Mar 28, 2022 ▶ 5:41 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Disclosure
Jeff Lieberman: Insight Partners does not set deal or deployment targets
“Like, we don't have no targets. It's not like, oh, we need to do X number of deals or deploy X dollars of capital, or this is how much we're doing. That's an output, not something we manage to.”
Jeff Lieberman Mar 28, 2022 ▶ 14:26 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Insight
Lieberman: Valuation spreads between average and great assets compress during market booms
“In times like this, we typically average assets get priced way up. Great assets get priced up, but the spread between those assets probably compresses.”
Jeff Lieberman Mar 28, 2022 ▶ 15:41 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Insight
Lieberman: People are either long on money and short on time, or vice versa
“There's two commodities in life. You have money and you have time. And I had a wise entrepreneur a long time ago say, you can't have both. You have one. You're either long one and short the other or short one and long the other.”
Jeff Lieberman Mar 28, 2022 ▶ 20:11 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Disclosure
Lieberman: Insight Partners sold Trivago to Expedia for $1 billion
“A hundred days later, we wire and invest in a company called Trivago. Four years later, we sell it to Expedia for a billion dollars.”
Jeff Lieberman Mar 28, 2022 ▶ 22:35 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Insight
Jeff Lieberman: Managing people is harder than the analytical work in VC
“Managing people is definitely the hardest part of the job and the emotional side of it and understanding their needs. I mean, the analytical stuff is fun and easy, and you know, the numbers don't Yell back, but the people do, and like, putting yourself out the…”
Jeff Lieberman Mar 28, 2022 ▶ 25:06 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Insight
Lieberman: Macro trends, not just fundamentals, drive 10x to 30x venture returns
“So kind of the company gets you to a base case, but the macros are what allows you to break out and really see tail. Because if you don't have those macros, it's kind of hard to break out and have, you know, a 10, 15, 20, 30 time your money kind of investment.”
Jeff Lieberman Mar 28, 2022 ▶ 28:03 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Insight
Lieberman: Learning from failure is much easier than learning from success
“I think it's much, much easier to learn from failure than from success.”
Jeff Lieberman Mar 28, 2022 ▶ 29:31 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
What-if
Lieberman: Failed deals provided necessary conviction for subsequent profitable investments
“I invested in a lot of companies where I lost money, and ultimately, those companies led me to another investment where I made a lot of money, and if I didn't invest in the first company, I would have never had the courage and the conviction and learnings to i…”
Jeff Lieberman Mar 28, 2022 ▶ 30:28 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Assertion Not checkable as stated
Lieberman: Insight Partners culture avoids celebrating wins or dwelling on losses
“This is not a culture where we celebrate victories. We don't wallow in the loss either, but we're not sitting here celebrating the victories, and it's all about how do we get up and do it again?”
Jeff Lieberman Mar 28, 2022 ▶ 32:33 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Insight
Lieberman: Investors must moderate perspectives during market booms and busts
“I think the biggest lesson is that you got to moderate your point of view on the ups, and you got to moderate your point of views on the down. It's probably never as bad as it looks, probably never as good as it looks.”
Jeff Lieberman Mar 28, 2022 ▶ 10:20 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Insight
Lieberman: A 50% margin SaaS company is 2.5x more valuable than 20%
“One SaaS company will have a 50% cash flow margin. The other will have a 20% cash flow margin. One is going to be theoretically in the long term, this is my Wharton education kicking in, two and a half times more valuable than the other.”
Jeff Lieberman Mar 28, 2022 ▶ 15:06 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Disclosure
Lieberman: Insight was Shutterstock's first investor at $5M revenue
“We were really early on photography, so I invested in a company called Shutterstock, which we took public. We were the first investors that, like, it was a five million dollar company at the time.”
Jeff Lieberman Mar 28, 2022 ▶ 26:05 20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff

The other half of the tape: Jeff Lieberman's own voice is left out of every number here. Other people bring the name up 8 times in 3 episodes on 20VC. every mention, with the transcript →

Who brings them up most Harry Stebbings 5Jerry Murdock 2Deven Parekh 1

Every mention by year

Appearances (2)

EpisodeDateSpeaking time
20VC: 13 of the Great Investing Minds on When to Pay Up vs When To Remain Disciplined and compilation Aug 12, 2022 1m
20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings o Mar 28, 2022 24m
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