The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

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why aren't all 30 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Prediction Held up
Deeter: Top three LLM companies will raise $100B in six months
“I think the numbers right now, the top three LLMs, if you include you know, Anthropoc, OpenAI, and X in there, ah, are gonna raise a hundred billion dollars in this six month period”
Byron Deeter Aug 25, 2025 ▶ 8:49 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Prediction Partly held up
Deeter: AI Will Double Vertical SaaS TAM and Valuation Just Like Payments Did
“I think AI is going to do the same thing, that what it can do you know, with Service Titan, as they talk about automating the technician experience and the ability to go out there and have a co-pilot alongside of you.”
Byron Deeter Aug 25, 2025 ▶ 11:05 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Prediction Held up
Deeter: 10-Person Micro-Businesses Will Reach Billion-Dollar Valuations
“I think we're going to see the era of the micro business. I think that we're going to have, you know, 10 person companies that are crossing billion dollar valuations and, you know, kids in schools are going to be able to launch businesses in real time in, in w…”
Byron Deeter Aug 25, 2025 ▶ 19:19 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 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
Prediction Held up
Deeter: AI will mirror top scientists' reasoning within 18 months
“The curve is still up into the right, without a doubt, and I do believe that we will cross over this term. You know, people use you know various different terms about you know, levels of reasoning and awareness and AGI and the like. I have no doubt we're, if w…”
Byron Deeter Aug 25, 2025 ▶ 30:10 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Assertion Supported
Deeter: VC is one of few asset classes where past performance predicts success
“It is one of the few asset cycles where past performance is an indicator of future success.”
Byron Deeter Aug 25, 2025 ▶ 1:09:14 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Prediction Held up
Deeter: Venture Capital Index Will Underperform S&P 500 Again
“Historically, it has underperformed the S&P and probably will again in this case but you'll make money.”
Byron Deeter Aug 25, 2025 ▶ 1:13:15 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Assertion Supported
Cloud Valuations Over 20x Revenue and Snowflake at 80x Are Unsustainable
“The average multiple is trading north of twenty-x revenue, and you look at a snowflake that's trading at 80 times revenue. That's not sustainable.”
Byron Deeter May 27, 2021 ▶ 33:46 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 Held up
Deeter: Consumer delivery startups face shut downs as funding dries up
“A number of these delivery businesses, as an example, have been targeted. And I suspect several of those will have unfortunate outcomes and will not have further capital available.”
Byron Deeter May 2, 2016 ▶ 10:24 20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight
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
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 Supported
Shopify Remains One of Stripe's Largest Customers Instead of Building In-House
“They're certainly one of Stripe's largest customers, if not the largest, and yet it's a great relationship. And at any point, of course, Shopify could have brought that in house.”
Byron Deeter May 27, 2021 ▶ 13:37 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 Didn’t hold up
Cloud Companies Will Absorb Multiple Compression Through Strong Revenue Growth
“These companies are growing at north of 40% on the public side, and on the private side, usually growing 80 to a hundred percent plus for the best companies, and so you can absorb some multiple compression and still compound value and be a win for everyone inv…”
Byron Deeter May 27, 2021 ▶ 34:04 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
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
Prediction Held up
Multiple $10B+ private cloud companies will soon transition to public markets
“You're going to see these Ten billion dollar plus caliber companies starting to flip from private to public, and the lights will turn on on this segment in a way that public market investors and, frankly, the community more broadly doesn't yet fully appreciate”
Byron Deeter Jul 8, 2019 ▶ 10:06 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
Deeter: Late-stage private SaaS traded at 3-4x public multiples
“At the end of the day, these businesses traded at, you know, three or four times the multiples of their public peers, and that isn't sustainable long-term.”
Byron Deeter May 2, 2016 ▶ 8:28 20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight
Assertion Contradicted
Byron Deeter: Snowflake had negative gross margins late in its life cycle
“And so you can look at a business like a snowflake that had negative gross margins very late in their life cycle.”
Byron Deeter Aug 25, 2025 ▶ 4:43 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Assertion Supported
Deeter: Adding Payments Doubled TAM and Market Caps for Vertical SaaS
“And as I think back on our vertical SaaS investments, you know, like a Shopify or a Service Titan or a Toast, when they added payments, it became that big Next Horizon unlock for them and really doubled the TAM and the market caps for these businesses.”
Byron Deeter Aug 25, 2025 ▶ 10:51 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
Prediction Held up
Deeter: Canva, Anthropic, and Perplexity will not go public anytime soon
“Now you look at, you know, Canva, you know, forty billion plus, and Anthropica with seventy billion plus, and perplexity, you know deep into DekuKorn status, and like, these businesses, you know, aren't going public anytime soon.”
Byron Deeter Aug 25, 2025 ▶ 38:09 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Assertion Partly supported
Deeter: First three VC investments failed before next two hit billion-dollar IPOs
“I had my first three investments were all very bad. My next two ended up being, you know, billion dollar IPOs.”
Byron Deeter Aug 25, 2025 ▶ 1:04:00 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Assertion Supported
Twilio Is Bessemer's Largest Investment in Total Dollars and Returns
“The initial investment started with David Callen leading a 125,000 dollar seed investment as part of this seed extension round that Mitch Kapoor led, and Ethan Kurzweil, who's now one of our great partners, was a senior associate at the time, and Ethan slid a …”
Byron Deeter May 27, 2021 ▶ 4:22 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
Assertion Partly supported
Twilio Went Through Multiple CROs Trying to Crack Enterprise Sales
“We went through several chief revenue officers who were quite capable, and yet couldn't fully crack it.”
Byron Deeter May 27, 2021 ▶ 18:07 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
Assertion Supported
Microsoft is aggressively gaining market share in enterprise public cloud
“They are several years into this transition and as Microsoft generally does, they're doing a great job of being a fast follower. And are very aggressively gaining share and making strides on the enterprise segment of public cloud specifically.”
Byron Deeter Jul 8, 2019 ▶ 8:13 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 Contradicted
Enterprise software valuations in 2019 are at 20-year highs
“These valuations are certainly the highest we've seen for an enterprise company in the last probably two decades.”
Byron Deeter Jul 8, 2019 ▶ 12:09 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
Adaptive Insights took a $1.6B Workday acquisition three days pre-IPO
“Including Adaptive Insights, by the way, last year, who was three days away from going public, and then instead chose to take the Workday offered a 1,000,000,006 instead.”
Byron Deeter Jul 8, 2019 ▶ 15:30 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
Twilio Allocated 1% of Pre-IPO Equity to Charity, Not Founding Equity
“He early on came to the board and said, I want to allocate one percent of Twilio's equity and not in like a marketing way where it's one percent of when we founded it, but like one percent now immediately pre IPO, which by the way is now worth hundreds of mill…”
Byron Deeter May 27, 2021 ▶ 26:00 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
Assertion Supported
Bessemer is tracking 53 private cloud unicorns globally as of 2019
“I think that the floodgates are about to burst wide open, and as we look at the private cloud landscape, we do the cloud 100 event every year with Forbes, and it'll be in the September issue this year from the cloud 100 list, but right now we're tracking 53 pr…”
Byron Deeter Jul 8, 2019 ▶ 9:20 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
Deeter: Box had over 130% net upsells in its IPO prospectus
“Was the fact that they had over a 130% net upsells, meaning if you stopped closing any new business and essentially fired your sales and marketing team, the business would still grow 30%.”
Byron Deeter May 2, 2016 ▶ 17:07 20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight
Assertion Supported
Deeter: Cornerstone On Demand went public with $50M ARR and $700M market cap
“My very first IPO, Cornerstone On Demand, you know, went public with fifty million of ARR, and I think with seven hundred million market cap, and they traded up to billions over time.”
Byron Deeter Aug 25, 2025 ▶ 37:56 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
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