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why aren't all 98 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 2 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 Not checkable as stated
Cloud macro battle will result in fatalities among legacy tech vendors
“And so there's this macro battle of risk going on with the legacy vendors, and there will be some fatalities there, but it's enabling the infrastructure service layer that now the pure place can continue to benefit from.”
Byron Deeter Jul 8, 2019 ▶ 8:26 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
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
Prediction Not checkable as stated
Deeter predicts automated bookkeeping startup ScaleFactor will become a household name
“So the most recently announced one is a small company in Austin That people probably haven't heard of yet called scale factor, which I firmly believe will be a household name in the coming years.”
Byron Deeter Jul 8, 2019 ▶ 29:32 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
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
Prediction Not checkable as stated
Deeter: Late-stage private SaaS companies face the hardest squeeze ahead
“It's really the late stage private companies that are going to get squeezed the hardest in the coming months because they've had this reality distortion field in the jobs in the sense of valuations and operations in some cases. That were, that was really fuele…”
Byron Deeter May 2, 2016 ▶ 8:02 20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight
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
Insight
Deeter: Reducing churn is the #1 lever for SaaS lifetime value
“Hands down, the single biggest thing a company can do to drive long-term lifetime value of the business and increase margin is to improve those churn stats.”
Byron Deeter May 2, 2016 ▶ 14:04 20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight
Assertion Not checkable as stated
Deeter: Each 1% monthly churn reduction equals $100M market value
“We quantified that to roughly a hundred million dollars of market value for every one percent of monthly churn you can change.”
Byron Deeter May 2, 2016 ▶ 14:16 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
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
Prediction Not checkable as stated
Deeter: Ecosystem startups around top LLMs will produce 100x VC returns
“However, there are hundreds of other Really compelling venture businesses that will be created in and around those ecosystems. And I do believe there will be great venture outcomes by from a number of companies in and around those businesses. And so the power …”
Byron Deeter Aug 25, 2025 ▶ 9:08 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
Assertion Not checkable as stated
Deeter: Amazon, Google, and AMD chipsets are challenging Nvidia's market dominance
“I do think that we're also getting many more hardware approaches and solutions out there. So that it's not as wonderful as NVIDIA is. It's not just an NVIDIA world anymore. And the chip sets from Amazon and Google and AMD and others are becoming quite capable.”
Byron Deeter Aug 25, 2025 ▶ 30:56 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
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
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
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
Opinion
Deeter: The best venture capital firms are flat at the top
“The end of the day, I think the best firms are pretty flat at the top.”
Byron Deeter Aug 25, 2025 ▶ 1:08:47 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Opinion
Deeter: Sequoia Capital Continues to Deliver Platinum-Level Investment Returns
“Quantitatively, I think that, you know, Sequoia continues to mint platinum records.”
Byron Deeter Aug 25, 2025 ▶ 1:18:18 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
Disclosure
Twilio's Revenue Was Declining Month-Over-Month When Bessemer First Invested
“When we made the investment, not only was the revenue tiny, but it was actually down month over month.”
Byron Deeter May 27, 2021 ▶ 6:17 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
Founders Should Default to APIs Because Companies Rarely Replace Them
“If I was a CEO today, and when I'm in the boardrooms today with CEOs, my advice is where you can plug in APIs and use them for whatever the capability is, do that first. And over time, constantly look at designing it out, but you almost never will.”
Byron Deeter May 27, 2021 ▶ 14:27 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
What-if
Deeter Expected Video to Overtake Voice and SMS Much Faster
“I certainly have expected video to take off faster than it did. As you think about the Twilio product set, for instance, and all of the channels that we've entered now, I would have thought that voice and SMS would have plateaued earlier, and that video would …”
Byron Deeter May 27, 2021 ▶ 15:02 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
Insight
Founders Cannot Outsource Early GTM Discovery to Early Sales Hires
“And you can't outsource that to your sales team early, or you're going to lose the magic. You're going to lose the insights, and you're going to shoot the rocket off, 10 degrees off target, even if it's working.”
Byron Deeter May 27, 2021 ▶ 22:15 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 Not checkable as stated
Home Run IPO Valuations Expanded 100x to $50B+ Over 15 Years
“What used to be a home run at a half billion dollars for an IPO, is now a fifty billion dollar and above IPO. I mean, literally two orders of magnitude bigger than”
Byron Deeter May 27, 2021 ▶ 27:35 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
Bessemer Holds 25 to 30 Unicorns in Its Private Cloud Portfolio
“Within our private cloud portfolio right now, I think we have between 25 and 30 Unicorns that have obviously chosen to raise, you know, large financings north of a billion”
Byron Deeter May 27, 2021 ▶ 31:07 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
Insight
Startups Facing Preemptive Term Sheets Should Raise Half-Rounds Ahead
“Raise a half round ahead, not a full round ahead. So this idea of if you can envision deploying more capital and initially we are going to raise this money to get through these phases, let's think about the intermediate milestones where we can then go out and …”
Byron Deeter May 27, 2021 ▶ 32:10 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
Bessemer avoids market timing to pay fair prices for visionaries
“Great companies are built in all markets, and so I've really given up trying to time markets either as a founder or as an investor, and my point of view is Find great people with big vision and pay the fair market price, and generally, really good things happe…”
Byron Deeter Jul 8, 2019 ▶ 4:51 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
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
Insight
Capital-efficient startups pull away from competitors in down markets
“However, in the medium to down markets, you will be disproportionately rewarded, because investors will flock to quality, and you will have the ability to invest in your model when others don't. As the cost of capital spikes in the market, the efficient busine…”
Byron Deeter Jul 8, 2019 ▶ 14:22 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
Insight
Team misalignment causes Bessemer's most painful investment losses
“The team really is our number one factor and where we've lost money or where we've had very painful experiences along the way is where We just got out of sync with the team or didn't fully understand where the team was headed.”
Byron Deeter Jul 8, 2019 ▶ 15:45 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
Insight
Public company boards should spend half their time on strategy
“Preserving the time for the strategic stuff is the most important actual use of the boardroom members, and so, for private companies, that ratio tends to be the vast majority, and the update part is very modest, and when you get to the public side, at least tr…”
Byron Deeter Jul 8, 2019 ▶ 24:02 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 Not checkable as stated
AI and China will disrupt the tech sector over the next decade
“The first talks about AI and China specifically, two of the macro forces that will totally disrupt tech in the next decade”
Byron Deeter Jul 8, 2019 ▶ 26:27 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
Insight
Deeter: SaaS companies growing under 100% derive most revenue from renewals
“Any business that's growing less than a hundred percent has the majority of their this year's revenue locked up in renewals and upsells, not net new business.”
Byron Deeter May 2, 2016 ▶ 12:51 20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight
Insight
Deeter: Growth is single most correlated short-term variable to enterprise value
“Growth is still fundamentally rewarded, and it's the single most correlated variable in the short term To enterprise value. Really, if you deconstruct where the outliers are both good and bad, you'll find that it's efficient growth that's rewarded most.”
Byron Deeter May 2, 2016 ▶ 15:20 20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight
Disclosure
Deeter: Bessemer Is Targeting Vertical AI in Accounting, Legal, and Medical
“We're going down accounting and legal and medical. We're going through these sectors where there's a lot of, you know, front edge humans doing busy work and paperwork, and we're supercharging them.”
Byron Deeter Aug 25, 2025 ▶ 16:11 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Disclosure
Deeter: Bessemer's largest all-time investments include Twilio, Canva, and Anthropic
“So it used to be Twilio. Then you know, probably StubHub, Canva, Anthropic Yeah, probably, probably that bucket.”
Byron Deeter Aug 25, 2025 ▶ 44:54 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Disclosure
Deeter: My first Bessemer investment roadmap was in zero-trillion-dollar RFID market
“My first roadmap at Bessemer was RFID, radio frequency identification, which was and is a zero trillion dollar market.”
Byron Deeter Aug 25, 2025 ▶ 1:03:14 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Disclosure
Stripe Is Number One on Bessemer's Private Cloud 100 List
“Stripe, which is cloud number one on our private cloud 100 list today with Snowflake's graduation, most likely.”
Byron Deeter May 27, 2021 ▶ 16:24 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
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
Disclosure
Deeter: Bessemer Venture Partners has made 105 cloud investments
“This is one of the points that I try to highlight in our 10 laws of cloud computing within investment framework, pattern recognition across now our 105 cloud investments we've done.”
Byron Deeter May 2, 2016 ▶ 6:22 20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight
Disclosure
Deeter: Bessemer maintains deal cadence and capital deployment despite pullback
“We're still doing just as many deals. We're still putting out the door, roughly the same amount of capital.”
Byron Deeter May 2, 2016 ▶ 9:12 20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight
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