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Prediction Open · timeframe Aug 2028
Deeter: Anthropic will be valued over $1 trillion within three years
“I mean, we put our money where our mouth is. We've been a buyer. So over, and that's again, like we a year ago when we were buyers, we still wouldn't have didn't conceive of that.”
Byron Deeter Aug 25, 2025 ▶ 1:22:03 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Opinion
Fisher: Raising too much seed capital distorts startup culture and execution
“No, at seed I don't think so. I think it distorts everything. Everything from the go-to-market model to how you hire, to the offices and the culture you're creating, it's all wrong. I, so I completely disagree.”
Adam Fisher Jan 22, 2024 ▶ 47:15 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Insight
Fisher: Fastest-growing and most ambitious startups often crash and burn
“I don't think that the way you build a big company or the way you get a big exit is by investing in the most ambitious companies, growing the fastest. Those are also the companies that crash into it.”
Adam Fisher Jan 22, 2024 ▶ 0:00 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Insight
Fisher: VCs cannot accurately predict which portfolio companies will win
“There's no question that, at the end of the day, you, most of your returns are gonna come from very few deals. It's not gonna be spread evenly. That's a fact. The question is, can you recognize it early on, or can you recognize it really at any point? And I do…”
Adam Fisher Jan 22, 2024 ▶ 52:15 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Assertion Supported
Deeter: Top AI Startups Hit $100M ARR in 1.5 Years
“We're seeing businesses go from zero to a hundred million in 1.5 years. That's the supernova profile.”
Byron Deeter Aug 25, 2025 ▶ 24:44 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Disclosure
Deeter: Bessemer refuses to hire sector-specific investors or protect cooling sectors
“This is very much why we don't hire sector-specific investors, and we don't give you air cover if your sector goes out of favor, meaning our job's to make RLPs money, and if you're in a sector that's cooling off, you better get the hell out and go somewhere el…”
Byron Deeter Aug 25, 2025 ▶ 1:00:54 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Opinion
Deeter: Bessemer invested in Anthropic believing it could be a 30x return
“You know, 3.8 X will keep you in business for a long time, but the reason to do it is because you believe it could be a 30 X. And that's the basis of our anthropic investment is we believe that it is a generational company.”
Byron Deeter Aug 25, 2025 ▶ 7:09 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Insight
Fisher: High cost basis forces VCs into risk-averse board mindsets
“When you invest a lot more money at a lot higher valuations you actually end up behaving a little bit different as a board member even when all of a sudden you have a hundred million of cost basis in a company, in which I do have several companies where that's…”
Adam Fisher Jan 22, 2024 ▶ 56:56 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Disclosure
Fisher: Back founders who can raise capital even when missing operating plans
“I invest in people who I think can raise money even when they're not, even when they don't meet their plan.”
Adam Fisher Jan 22, 2024 ▶ 18:30 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Disclosure
Fisher: I refuse to double down on companies with unsustainable burn rates
“I don't mind having missed an opportunity to invest three more million dollars in a company that could have generated another thirty million dollars of gains, but I do worry a lot about doubling down in a company, investing another twenty million dollars, and …”
Adam Fisher Jan 22, 2024 ▶ 54:38 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Insight
Fisher: Never raise funding at valuations equal to your target sale price
“I try and make sure my companies I back never raise at valuations that they want to sell the company at, and I warn them of that.”
Adam Fisher Jan 22, 2024 ▶ 44:25 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Fisher: I have achieved surprisingly high exits on sub-$2M revenue startups
“And so I would say at least six or seven times I've had exits where, I mean, the company Was almost worthless. You know, less than two million dollars of revenue, and we had offers that shockingly good.”
Adam Fisher Jan 22, 2024 ▶ 1:04:32 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Bessemer capped Procore's upside potential at $300M in its Series A thesis
“So Bessemer, I don't know if Brian told you this, but Bessemer had an investment thesis on Procore that they, of course, they don't tell the company about. They thought that Procore the best outside scenario they could come up with was that Procore was going t…”
Tooey Courtemanche Dec 4, 2023 ▶ 22:07 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
What-if
Levine: Bessemer Would Have Missed Pinterest Without Partner Sarah Tavel
“Had we not had, at least on a gender basis, A diverse duo of people looking at the investment. I think we would have missed it, too.”
Jeremy Levine Mar 24, 2021 ▶ 19:31 20VC: The Pinterest Memo: Bessemer's Jeremy Levine on The Secret To Success within User Generated Content Plays, Where Most Investors Make Mistakes When Analysing Consumer Social and How The Pinterest Deal Wouldn't Have Happened without a Diverse Partners
Insight
Levine: Publicizing Early VC Funding Rounds Hurts Long-Term Startup Prospects
“A lot of people, particularly around their early financings, like to go tell the world about it. It's validation. If nothing else, it's nice to have your mom read about you in TechCrunch. But the truth is, that does almost no value. It adds no value to your co…”
Jeremy Levine Mar 24, 2021 ▶ 37:33 20VC: The Pinterest Memo: Bessemer's Jeremy Levine on The Secret To Success within User Generated Content Plays, Where Most Investors Make Mistakes When Analysing Consumer Social and How The Pinterest Deal Wouldn't Have Happened without a Diverse Partners
Prediction Not checkable as stated
High cloud valuation multiples today will look cheap in the long term
“Whatever rich prices we're paying today, We will get rewarded many times over if we pick the winners and hold onto them long term, and so we're certainly anxious as everyone else is around the multiples. They are rich, but at the end of the day, I absolutely b…”
Byron Deeter Jul 8, 2019 ▶ 12:48 20VC: Bessemer's Byron Deeter On Lessons From Investing in 14 $Bn Companies, What The Heck Is Going On In Cloud Today and Why Cloud IPO Floodgates Are About To Burst Open
Disclosure
Deeter: Bessemer portfolio company hit 90% automated support with higher NPS via Fin
“I was at one of our portfolio company board meetings the other day, and they mentioned that they had switched from, you know, human-based interventions to the FIN product from Intercom, And they showed the stats of deflections went up, I forget to, you know, 9…”
Byron Deeter Aug 25, 2025 ▶ 14:08 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Assertion Supported
Bessemer Cloud 100 List Reaches $1 Trillion Aggregate Private Value
“We're over a trillion dollars In private market cap now among just the top 100 cloud AI companies right now which is just a astronomical number to consider.”
Byron Deeter Aug 25, 2025 ▶ 41:07 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Assertion Contradicted
Deeter: Canva and Intercom AI products generate hundreds of millions
“I look at a company like a Canva, or I look at a company like Intercom that's at a scale where in some ways they're already becoming an incumbent in those markets, and yet they're disrupting themselves at awesome rates and have AI products that are already, yo…”
Byron Deeter Aug 25, 2025 ▶ 13:23 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Disclosure
Deeter: Bessemer created 'Century Team' to re-underwrite top portfolio companies
“And we've actually added people and processes to make sure that we don't get subject to this kind of mental inertia where we invite in, you know, another partner to look at it and our best deals were constantly saying, You know, okay, we have the century team,…”
Byron Deeter Aug 25, 2025 ▶ 46:23 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Prediction Open · timeframe Aug 2028
Bessemer unlikely to pursue evergreen structures or asset management roll-ups
“We're seeing, you know, other firms adding asset management businesses and debt products and roll-ups and doing all sorts of things. You know, there's some kernels in there that we agree with. There's a lot in there we probably aren't going to pursue.”
Byron Deeter Aug 25, 2025 ▶ 58:02 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Opinion
Deeter: Secondary liquidity for venture investors is healthy as companies stay private longer
“This is a change in my view. I'll confess that I was pretty hard lined against this, not for founders and teams. I always feel that taking some pressure off of them is good, but I didn't love it when our co-investors were looking for liquidity. Early in busine…”
Byron Deeter Aug 25, 2025 ▶ 38:39 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Disclosure
Deeter: Bessemer is evaluating nuclear fusion investments accelerated by AI
“We're looking at, you know, fusion investments now that I think will be supported and accelerated by AI.”
Byron Deeter Aug 25, 2025 ▶ 22:13 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Disclosure
Deeter: Passed on Tesla Over Roadster Unit Economics
“One of the most famous and most painful for me was Tesla early on. It's on my anti-portfolio. If you go to the Bessemer website, we have a page dedicated to our screw ups, and that's one of mine. And it was because I couldn't fundamentally see how the unit eco…”
Byron Deeter Aug 25, 2025 ▶ 35:21 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Disclosure
Deeter: Bessemer invested over $100M each in Anthropic, Perplexity, and Canva
“You know, you look at an Anthropic or a Perplexity or a Canva and we, you know, we have, you know, nine figures into each of these companies and yet we are still, you know, well below historical venture standards where you aspire to own 20% or something in the…”
Byron Deeter Aug 25, 2025 ▶ 5:56 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Insight
Fisher: Niche market first movers offer better arbitrage than big market competitors
“That that it's a better arbitrage opportunity to be the lone player or the first mover in a even in a smaller market, even in a niche market, than to be the number two or three in a large market. Because a number two, it's like a gladiator competition. Number …”
Adam Fisher Jan 22, 2024 ▶ 16:28 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Disclosure
Fisher: Bessemer partnership gave outright negative feedback on my Wix deal
“In both cases, I received what would be politely say very lukewarm feedback from the partnership. In fact, in the case of Wix, it was outright negative feedback.”
Adam Fisher Jan 22, 2024 ▶ 27:55 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Insight
Fisher: Founder relationship outweighs market and product when investing
“I make it very clear to the entrepreneur that I'm choosing them more than I'm choosing the market or the particular product, and that I'm choosing them because I'm also not just choosing somebody that I hope will succeed or want to succeed, but somebody that I…”
Adam Fisher Jan 22, 2024 ▶ 41:38 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Insight
Fisher: Founder naivety beats industry insider experience due to lack of bias
“Insiders are just blinded by convention, by knowing a little bit too much of what hasn't worked in the past of where others failed. Naivete is a strength in these cases, and if you have the right entrepreneur who, again, is self-aware and perhaps also has a ce…”
Adam Fisher Jan 22, 2024 ▶ 11:20 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Insight
Fisher: Avoiding bad executive hires matters more than finding the optimal candidate
“So I'm much more interested in not making a mistake with a hire than making sure that this is the Best possible candidate we could hire.”
Adam Fisher Jan 22, 2024 ▶ 37:00 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Disclosure
Fisher: Raising $50M for an early-stage startup is inappropriate
“I mean, any early stage company that's raising fifty million dollars, I don't know what stage that was that you were thinking about, it's inappropriate. Those are not the type of invest, of entrepreneurs that I back.”
Adam Fisher Jan 22, 2024 ▶ 20:02 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Disclosure
Twilio Built Software Layers to Avoid Becoming a Commoditized Infrastructure Pipe
“The commoditization of communications or the migration of their larger customers. So I think you asked a very insightful question along the way, which I probably didn't give enough due to, which is we worried about that very heavily. And so part of our Preempt…”
Byron Deeter May 27, 2021 ▶ 36:32 20VC: The Twilio Memo: Bessemer's Byron Deeter on How a $125K Initial Check Became Bessemer's Largest Position, What The Influx of Late-Stage Capital Means For Venture Today & Why The Incumbent Advantage Is Now An Incumbent Disadvantage
Prediction Not checkable as stated
Venture Capital Will Bifurcate Into Regional Seed Firms and Global Platforms
“I do believe that the world is going to skew to a bimodal curve where there's going to be Super stage or regional firms. I put you in that bucket where you are going to be a fantastic early stage European partner for seed stage firms, and we look forward to co…”
Byron Deeter May 27, 2021 ▶ 28:47 20VC: The Twilio Memo: Bessemer's Byron Deeter on How a $125K Initial Check Became Bessemer's Largest Position, What The Influx of Late-Stage Capital Means For Venture Today & Why The Incumbent Advantage Is Now An Incumbent Disadvantage
Insight
Tech Incumbents Face an Incumbent Disadvantage Against Lean Startups
“When realizing that this notion of an incumbent advantage, I firmly believe now is an incumbent disadvantage. It is really hard to beat a focused, you know, lean team with their head down going after a problem set.”
Byron Deeter May 27, 2021 ▶ 9:12 20VC: The Twilio Memo: Bessemer's Byron Deeter on How a $125K Initial Check Became Bessemer's Largest Position, What The Influx of Late-Stage Capital Means For Venture Today & Why The Incumbent Advantage Is Now An Incumbent Disadvantage
Disclosure
Levine: Bessemer's Pinterest Memo Assigned 25-30% Chance of Total Failure
“And the chance of it being a big zero for a company at that stage is at least 25 or 30%, which means that the chance of it working is also not going to be huge.”
Jeremy Levine Mar 24, 2021 ▶ 35:09 20VC: The Pinterest Memo: Bessemer's Jeremy Levine on The Secret To Success within User Generated Content Plays, Where Most Investors Make Mistakes When Analysing Consumer Social and How The Pinterest Deal Wouldn't Have Happened without a Diverse Partners
Disclosure
Twitch pitched around 40 VCs before raising post-pivot round with Bessemer
“The first VC round after the pivot was with Bessemer and we struggled to raise that round. We had to pitch a lot of VCs, but Bessemer is amazing, but like we probably pitched four EVCs in that round. It was a struggle. Nobody wanted to invest in Twitch at firs…”
Emmett Shear Feb 21, 2020 ▶ 30:46 20VC: Twitch Founder & CEO Emmett Shear on When To Persist vs When To Give Up For Entrepreneurs, The Fundamental Tension When Scaling Orgs and How To Optimise Them & How The Role of CEO Fundamentally Changes with Scale
Disclosure
Bessemer passed on Tesla after failing to foresee its financial viability
“Tesla is the one that is front and center for me. I'm a car geek at hard. I love hardware products, and spent a lot of time with them early on, and just couldn't see the path to viability of the high-end car in a tough automotive time, so I bought the first ca…”
Byron Deeter Jul 8, 2019 ▶ 28:23 20VC: Bessemer's Byron Deeter On Lessons From Investing in 14 $Bn Companies, What The Heck Is Going On In Cloud Today and Why Cloud IPO Floodgates Are About To Burst Open
Assertion Supported
Bessemer data shows tech foundings are evenly spread while exits cluster
“And we've actually empirically modeled this. If you look at founding dates of the great companies that we think of across tech, and it's amazingly even across cycles, what you tend to see those that exits do cluster.”
Byron Deeter Jul 8, 2019 ▶ 6:03 20VC: Bessemer's Byron Deeter On Lessons From Investing in 14 $Bn Companies, What The Heck Is Going On In Cloud Today and Why Cloud IPO Floodgates Are About To Burst Open
Disclosure
Bessemer Passed on Yammer by Overfocusing on Technical Buyers
“Well, one early on in my career was a company called Yammer that we missed. You know, I had a number of opportunities to invest, and I think the reason we missed is we were very focused in those days, the developer platform, on selling a sort of API-like servi…”
Ethan Kurzweil Jun 28, 2017 ▶ 20:16 20VC: Bessemer's Ethan Kurzweil on How To View Pattern Recognition and Deal With The Anti-Portfolio, The Next Frontier In Developer Focussed Businesses & Why eSports Is Interesting Again
Opinion
Farmer: Traditional VC model is outdated and must be rebuilt from scratch
“After a few years, I felt that VC was outdated. So I left Bessemer to study one question. If you were to strip a venture curve down to the bare metal to where to recreate a firm from scratch, how would you build a next generation VC?”
Chris Farmer Nov 30, 2016 ▶ 4:44 20VC: Why There Is A Revolution In VC, Why Boards Are Inherently Inefficient & Why Data Will Be Central To VC In The Future with Chris Farmer, General Partner @ SignalFire
Insight
Deeter: Outbidding competition for tech talent is an unwinnable arms race
“Really the primary job of the CEO obviously is to hire a great team, but you do that not by outbidding your competition in this market. That's an unwinnable arms race. You need to pay fair market economics, but really what you need to do is compel them by the …”
Byron Deeter May 2, 2016 ▶ 6:32 20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight
Disclosure
Deeter: Bessemer expects $1 of ARR growth per $1 net burn at Series B
“A crude rule of thumb we use for call it series B companies, roughly that ten million dollar stage of ARR is one to one, which is we like to see for every dollar of net burn, we'd like to see a dollar of ARR growth added.”
Byron Deeter May 2, 2016 ▶ 16:01 20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight
Disclosure
Deeter: Bessemer owned 28% of Shopify and Twilio at IPO
“We own 28% of Shopify and Twilio at IPO and we owned, you know, well less than that of Procore and Service Titan just because we, you know, included a lot of other investors downstream.”
Byron Deeter Aug 25, 2025 ▶ 51:22 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Assertion Supported
Deeter: Growth Is Valued at 2x to 2.5x Efficiency at $50M ARR
“The rule of X mathematically shows it's about a two to two and a half X multiplier value of growth over efficiency at mid-stage scale. Call it fifty million ARR or so.”
Byron Deeter Aug 25, 2025 ▶ 27:41 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Disclosure
Bessemer distributed Shopify stock to LPs rather than selling directly
“So importantly, we distributed early. We didn't necessarily sell. So what we did is we gave people the choice.”
Byron Deeter Aug 25, 2025 ▶ 56:28 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Opinion
Mitchell Green: Bessemer is as good as any mega-fund for $50M+ checks
“If you need to own a large fund and write a fifty hundred million dollar plus check, like I think Bessemer is as good as any of the other big funds.”
Mitchell Green Mar 26, 2025 ▶ 1:12:55 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Fisher: Founders need a confidant partner, not a prescriptive investor
“One of the things that I eventually, ah, did myself when I started at Bessemer, ah, this is in 2000 and seven, was to, Take a very different approach to take this kind of partnership type of approach with the entrepreneur, because I realize what they really ne…”
Adam Fisher Jan 22, 2024 ▶ 4:31 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
Disclosure
Fisher: Investing exclusively in my ideal founder typecast does not scale
“I accept that sometimes I have a lot of biases towards certain types of entrepreneurs, and I can't always invest in the same Adam Fisher typecast entrepreneur that even though that works for me, it doesn't scale and I'll probably miss out on some very good one…”
Adam Fisher Jan 22, 2024 ▶ 30:24 Adam Fisher: Why Small Markets are Better Than Big Markets | E1106 · 20VC with Harry Stebbings
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