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.

clear all ✕

why aren't all 72 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 4 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

Disclosure
O'Driscoll: Scale Has Never Paid Double a Valuation Three Months Later
“Can you stomach paying, you know, twice as much as someone three months ago? We've never done that.”
Rory O'Driscoll May 15, 2025 ▶ 6:50 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
Disclosure
O'Driscoll: Averaged two venture deals per year over 30-year career
“I do two deals a year. Shockingly, I've been in this business 30 years and I've done 60 deals.”
Rory O'Driscoll May 8, 2025 ▶ 22:11 Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings
Insight
O'Driscoll: High-variance investment exceptions only work in single-leader firms
“It's no accident that the firms that have high, you know, position betting variants where they're willing to go anywhere are single leader dominated.”
Rory O'Driscoll Apr 24, 2025 ▶ 1:10:48 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Insight
O'Driscoll: Missing 5X–10X deals in a firm's sweet spot is far worse than missing outliers
“I'm far more worried about missing a five or like a five or a 10 X deal that was in the scale sweet spot of, you know, one to ten million in revenue, series A or B enterprise software. When you miss that, or even worse, when you turn it down, that's when you h…”
Rory O'Driscoll Apr 24, 2025 ▶ 1:13:43 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Disclosure
O'Driscoll: Lost a deal by refusing founder equity refresh concessions
“Yeah, I've lost a deal to not doing that, and you're right, I'm going to be sympathetic to the investor now. I've lost a deal to not doing that, because again, it sticks back to my comment, I tend to be perhaps stuck in the, we, it's not war, stuck in the mud …”
Rory O'Driscoll Apr 17, 2025 ▶ 1:18:41 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Disclosure
O'Driscoll: Scale Rejects Static $30 Million Markets but Accepts Fast-Growing Ones
“If someone says to me, it's a thirty million dollar market right now, expanding at a hundred percent, I'm intrigued. If someone says to me, it's always going to be a thirty million dollar marketplace, I got to turn it down.”
Rory O'Driscoll Nov 28, 2016 ▶ 11:53 20VC: Why Market Is More Important Than Team, The 4 Key Roles of A Board Member & Why Founders Get Market Sizing So Wrong with Rory O'Driscoll, Founding Partner @ Scale Venture Partners
Disclosure
O'Driscoll: Scale accepts operational risk to avoid inflated valuation risk
“Instead, what I'm doing is taking on more operational risk in return for less Valuation risk, because I believe that right now that's the right trade-off to make.”
Rory O'Driscoll Nov 28, 2016 ▶ 5:54 20VC: Why Market Is More Important Than Team, The 4 Key Roles of A Board Member & Why Founders Get Market Sizing So Wrong with Rory O'Driscoll, Founding Partner @ Scale Venture Partners
Assertion Not checkable as stated
Scale Venture Partners Portfolio Averages 182% Growth Year After Investment
“The companies that we're investing in for the past couple of years have on average achieved a 182% growth in the year after we've invested.”
Sharon Wienbar Mar 19, 2015 ▶ 20:27 20 VC 021: Gender Equality, Startup Valuations and 'Friend Raising before Fund Raising with Sharon Wienbar
Insight
Wienbar: Existing Portfolio Support Always Trumps Evaluating New Deals
“So the, you know, money, the rule we have in here is money in the ground trumps new deal. So if you have a portfolio company issue, you know, you owe it to them. It's your fiduciary responsibility as a board member and to your existing investors that you've go…”
Sharon Wienbar Mar 19, 2015 ▶ 34:01 20 VC 021: Gender Equality, Startup Valuations and 'Friend Raising before Fund Raising with Sharon Wienbar
Prediction Didn’t hold up
Scale Venture Partners Requires a Board Seat in Every Portfolio Deal
“And in fact, that's part of our strategy is that we always have a board seat with our companies. We're very flexible on price terms, amount of dollars invested, but we always have a board seat.”
Sharon Wienbar Mar 19, 2015 ▶ 23:02 20 VC 021: Gender Equality, Startup Valuations and 'Friend Raising before Fund Raising with Sharon Wienbar
Assertion Supported
Wienbar: Scale Has Most Female Partners Among $200M+ US VC Funds
“Scale Venture Partners has three female partners, which is, I am sorry to say, the most in the U.S. Of any firm that has more than two hundred million dollars under management.”
Sharon Wienbar Mar 19, 2015 ▶ 3:24 20 VC 021: Gender Equality, Startup Valuations and 'Friend Raising before Fund Raising with Sharon Wienbar
Disclosure
O'Driscoll: Scale Venture Partners maintains a 50% fund reserve ratio
“We, you know, over like six or seven funds, we've been 50% reserve.”
Rory O'Driscoll Mar 26, 2026 ▶ 1:00:28 Why You Need a $1B Fund To Do Series A | SpaceX at $2TRN & Data Centers in Space | Groq's $20BN Deal · 20VC with Harry Stebbings
Disclosure
O'Driscoll: At most 50% to 60% of fund capital goes to follow-ons
“Most of my money goes in on my initial round. At most, 50, 60% comes in follow ons. So I can't afford to be wrong on two thirds of my money to be right on one third.”
Rory O'Driscoll Oct 30, 2025 ▶ 51:04 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Disclosure
O'Driscoll: Scale backed a 2x runner-up over a 15x market leader
“We did B. We got a two X. We didn't do A. We left a 15 X on the table.”
Rory O'Driscoll Oct 30, 2025 ▶ 1:07:26 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Insight
O'Driscoll: Every venture investment comes down to three sequential questions
“My mental model is always, we say this internally, is there a category that can support a big winner? Are these guys going to be one of the winners in the category? And are you getting paid for the risk? You could argue that's the kind of sequence of questions…”
Rory O'Driscoll Sep 11, 2025 ▶ 26:39 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Disclosure
O'Driscoll: Scale has deployed every fund over three years since 2010
“We've taken three years on every fund since 2010.”
Rory O'Driscoll Jul 24, 2025 ▶ 55:13 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Assertion Not checkable as stated
Rory O'Driscoll: Bill.com was second-quartile growth when ScaleVP invested
“For example, build.com It compounded to a huge network, right? And obviously, it was an amazing outcome for us, but the growth rate was always, I think, you know, second quartile, right? There were companies always growing faster.”
Rory O'Driscoll Jun 12, 2025 ▶ 46:46 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Disclosure
O'Driscoll: Scale Venture Partners caps fund concentration at 10%
“We have a capital concentration limit of 10%.”
Rory O'Driscoll Jun 12, 2025 ▶ 28:07 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Disclosure
O'Driscoll: ScaleVP has targeted 10% to 11% deal ownership since 2009
“We typically get around 10, 11% ownership, and that's been pretty consistent across Actually, five, six months, so all the way back to 2009. It's a pretty typical median.”
Rory O'Driscoll May 29, 2025 ▶ 34:55 OpenAI’s $6BN Jony Ive Deal & YC Is Both Chanel and Walmart, and Has Officially Won! · 20VC with Harry Stebbings
Assertion Not publicly verifiable
O'Driscoll: DroneDeploy has 20,000+ free users and 1,000+ paying customers
“Nice deal growing quickly, you know, 20,000 plus free users, a thousand plus paying customers.”
Rory O'Driscoll Nov 28, 2016 ▶ 28:16 20VC: Why Market Is More Important Than Team, The 4 Key Roles of A Board Member & Why Founders Get Market Sizing So Wrong with Rory O'Driscoll, Founding Partner @ Scale Venture Partners
Prediction Held up
O'Driscoll: Scale Venture Partners targets one to two deals per partner annually
“We aim to do one to two deals per partner per year, so there's not much difference. You're taking a board seat in every case, so you're very much time limited by what you can do anyway. So it's, you know, no different than, I would say, early stage, or even th…”
Rory O'Driscoll Nov 28, 2016 ▶ 6:11 20VC: Why Market Is More Important Than Team, The 4 Key Roles of A Board Member & Why Founders Get Market Sizing So Wrong with Rory O'Driscoll, Founding Partner @ Scale Venture Partners
Disclosure
O'Driscoll: Scale Venture Partners deploys 75%+ of capital into mid-stage startups
“About 75% plus of our dollars go in that kind of mid-stage, which is, you know, fairly early on in the company's life cycle.”
Rory O'Driscoll Nov 28, 2016 ▶ 4:45 20VC: Why Market Is More Important Than Team, The 4 Key Roles of A Board Member & Why Founders Get Market Sizing So Wrong with Rory O'Driscoll, Founding Partner @ Scale Venture Partners
Disclosure
Scale Venture Partners Nurtures LPs for Two to Three Fund Cycles
“So, you know, we typically know our LPs for two or three cycles before they decide to invest in us. And that's not uncommon for us and our portfolio companies.”
Sharon Wienbar Mar 19, 2015 ▶ 26:24 20 VC 021: Gender Equality, Startup Valuations and 'Friend Raising before Fund Raising with Sharon Wienbar
Disclosure
Wienbar: Scale Venture Partners Strictly Funds US-Focused Companies
“So our investment strategy is purely U.S. Focused. We don't invest, you know, in local market Companies for local markets.”
Sharon Wienbar Mar 19, 2015 ▶ 14:32 20 VC 021: Gender Equality, Startup Valuations and 'Friend Raising before Fund Raising with Sharon Wienbar
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