The Ledger

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Insight
Green: If a company responds to VC cold calls, it sucks
“And you realize if the company calls you back, the company sucks.”
Mitchell Green Mar 26, 2025 ▶ 2:21 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: DPI is the most important VC metric; marks are for suckers
“I believe I believe that, like, DPI is the most important thing, and marks are completely for suckers.”
Mitchell Green Mar 26, 2025 ▶ 1:10:31 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: Growth VCs should re-invest in public shares of former portfolio wins
“But what surprises me is that more funds, like, you know, if you were an early investor in Toast, and you're fully out of it, and you love the company, and the stock's down, like, 60%, like, why not go buy it again? Like, it surprises me more people don't do t…”
Mitchell Green Mar 7, 2026 ▶ 54:46 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Mitchell Green: Doubling a $100B VC investment requires $25B in earnings
“And you invest in something that's worth, like, it's worth a hundred billion dollars. You're effectively saying to make a double with dilution, it's probably two hundred and fifty billion dollars. Like, that's making the bet it's gonna do twenty-five billion d…”
Mitchell Green Mar 7, 2026 ▶ 57:38 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Green: Early-stage investors should exit and sell upon IPO
“If you are a early stage investor, when your company goes public, you should get off the board and sell the company.”
Mitchell Green Mar 26, 2025 ▶ 22:01 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: Emerging VC managers must utilize secondary markets
“What I believe like emerging managers and people starting venture funds need to do is take advantage of the secondary wind of the secondary markets.”
Mitchell Green Mar 26, 2025 ▶ 28:00 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: LPs must ask VCs why they held unlocked stock in 2021
“I believe a great question that people don't ask, that they should ask. Any manager who is around, who's been around 10 plus years, hey, in September of 21, September 30th of 21, how much unlocked stock did you have in your portfolio? And let's say September, …”
Mitchell Green Mar 26, 2025 ▶ 57:28 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Mitchell Green: Stocks without earnings or EBITDA have no valuation floor
“If you don't have earnings or EBITDA, there is no floor in a lot of these things.”
Mitchell Green Mar 7, 2026 ▶ 5:20 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Mitchell Green: Heavily leveraged incumbents are the primary targets for disruption
“Where I think the biggest opportunity to disrupt incumbents today is Soft software, tech enabled services, any company, it actually can be a manufacturing company, it doesn't matter, any company with a bunch of leverage on it, because those companies don't hav…”
Mitchell Green Mar 7, 2026 ▶ 7:08 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Mitchell Green: VCs should avoid easy responses and target hard-to-reach CEOs
“So if you, if the company calls you back, it's like, hang up the phone. It's the CEO you call every two days for a month. That's who you want to get on the phone.”
Mitchell Green Mar 7, 2026 ▶ 13:08 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Green: Portfolio Marks Are Opinions, DPI Is Math
“Marks are opinions. DPI is math.”
Mitchell Green Mar 7, 2026 ▶ 37:57 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Mitchell Green: Emerging VCs can deliver strong DPI using early secondary sales
“As a new relative upcomer in the first couple funds, you can actually generate amazing APIs. It's a game you can play.”
Mitchell Green Mar 7, 2026 ▶ 39:29 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Mitchell Green: Gross dollar retention is the most important tech metric
“It's the most important number in tech companies. Gross dollar retention.”
Mitchell Green Mar 7, 2026 ▶ 45:27 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Green: Incumbents usually win tech cycles through customer distribution
“The incumbents usually win. It's customer distribution.”
Mitchell Green Mar 26, 2025 ▶ 0:05 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: LPs are a VC firm's most important customer
“Well I would tell you that we have two customers. Founders, but more importantly, LPs, because if you do not have LPs, you do not have a business.”
Mitchell Green Mar 26, 2025 ▶ 47:45 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Mitchell Green: Buying is glamorous, but selling is the real job
“Buying is glamorous. Selling is the job.”
Mitchell Green Mar 7, 2026 ▶ 31:39 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Mitchell Green: Tech transformations require backing growth-focused management over margin-focused leadership
“I believe in any time you have big technological transformations, that you want the entrepreneur, you want the management team that is run by the company That, that is focused on growth.”
Mitchell Green Mar 7, 2026 ▶ 6:29 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Green: Founder purchases and big buybacks make companies much more bullish
“The companies that, the found, that, where the, like, founders are buying, or the companies are buying huge amounts of stock back, like, that, that to us would make one more bullish on that company versus, like, another company, a hundred percent.”
Mitchell Green Mar 7, 2026 ▶ 24:28 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Mitchell Green: A good company and a good investment are fundamentally different
“Good investment and good company are two very fundamentally different things too. And you're trying to like get the union of both of them.”
Mitchell Green Mar 7, 2026 ▶ 33:42 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Green: VCs add the most value by connecting founders to operators
“So I actually think that's the best way that VCs and private active people can help founders and entrepreneurs is connect them with people who have done it before and help them recruit.”
Mitchell Green Mar 7, 2026 ▶ 42:47 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Mitchell Green: 95% dollar retention enables fast growth with low burn
“The company that's got 95 gross dollar attention can grow really fast and not burn much money. Because they're not spending money on sales marketing to fill up the bucket.”
Mitchell Green Mar 7, 2026 ▶ 46:35 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Green: VC judgment comes from evaluating thousands of bad companies
“And you know how you know what a good company is over two years, talk to 10,000 bad companies.”
Mitchell Green Mar 26, 2025 ▶ 2:28 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: Target buying $10M-$20M software companies and exiting at $60M-$80M
“Let's go find stuff that we can just build, like, you know, invest when they're 10 to twenty million dollar revenue software businesses, and exit them when they're 60 to eighty million dollar software businesses.”
Mitchell Green Mar 26, 2025 ▶ 13:09 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: High Gross Retention Enables Software Businesses to Pivot to Profitability
“If you have 70, 75, 80% gross retention, it's much harder. But if you have a 90, 95% gross dollar retention business, yeah, like, make the hard decisions. You know, and get the thing to profitable.”
Mitchell Green Mar 26, 2025 ▶ 32:08 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: Good communication retains LPs through bad fund vintages
“By the way, without good performance, you can have none of it, but I can tell you that people, here's the thing though, people want the nice guy, the good guy, the person who communicates to win. So like, if you have a bad vintage or two bad vintage funds, the…”
Mitchell Green Mar 26, 2025 ▶ 48:57 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: LPs should reference check VC managers with failed founders
“I also think like LPs should spend more time talking to companies of portfolios that failed, like actually talk to the ones that didn't go well, or like were the one X's to find out what is the person really like to work with. Like the ones that work really we…”
Mitchell Green Mar 26, 2025 ▶ 58:18 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: Private companies often present total contract value as revenue
“A lot of it comes down to like, there'll be like, oh, my revenues are this. You look at the chart, you start doing all the analysis and you're like, actually that was your total contract value.”
Mitchell Green Mar 26, 2025 ▶ 1:11:33 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: Private companies frequently fudge gross profit numbers via COGS manipulation
“There's a lot of ways to fudge gross profit numbers and through cogs and all that kind of stuff.”
Mitchell Green Mar 26, 2025 ▶ 1:11:46 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: Emerging fund managers must strictly adhere to their promised LP strategy
“What you tell your LP is, just make sure you stick to it and do it. That's actually the best advice I can give for any emerging fund manager. It's like, look, define what you're gonna do, and do exactly that, and don't go out, don't go, don't stray from it at …”
Mitchell Green Mar 26, 2025 ▶ 1:17:46 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Green: Leaders should interview every employee annually to identify and eliminate operational failures
“You should interview all your employees. From admin to your other partners, and basically ask them for feedback. Just be like, hey, if you were running the place, what would you do differently? You know, like, tell me everything you do in your job, green, red,…”
Mitchell Green Mar 26, 2025 ▶ 1:19:47 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
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