Dan Siroker

Co-Founder & CEO, Limitless · 1 appearance on the record.

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Dan Siroker is the Co-Founder and CEO of Limitless, a personalized AI company. He previously founded Optimizely, scaling the company to $120M in ARR.

54statements → 10claims → 3claims resolved → 67%fully supported → 4.07/5average certainty → 2.46/5average debate potential → 4.4/5argument clarity · the sources → 4said about them ↓

2 supported 1 partly supported 0 contradicted 7 not checkable as stated how the 10 claims stand · each chip opens the sources

2 predictions · 8 assertions · 1 opinion · 29 insights · 13 disclosures · 1 what if · every statement was checked. The predictions and assertions are the 10 claims: statements the public record can support or contradict. 3 are resolved, and 7 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Dan argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported
Siroker: Top VC funds will break ownership minimums for hot startups
“Yeah, the best investors benchmark and recent, they will invest less than their supposed minimums for the right company.”
Dan Siroker May 15, 2024 ▶ 29:43 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings

Argument clarity: do they answer the question? how? →

4.4 / 5 directness 4.7 · coherence 4.7 · precision 4.2 · compression 3.9

answered every one of 46 assessed questions directly

This is a score against a rubric. It is not a rank. Every host question → answer exchange is scored with names hidden on directness, coherence, precision and compression, 1–5 each, on meaning alone: disfluencies are ignored, and only raw unedited episodes count. This is the score that measures thought. Every scored exchange, scores shown → · The rubric and its checks →

How they sound: speaking style how? →

312 words/min while actually speaking · 12.2 um and uh per 1k words · 11.5 false starts per 1k · 33.6% of pauses land inside a clause

Measured by listening to the audio itself: 15,451 words across 1 episode of raw-level tape, transcribed verbatim with every um and uh kept, each one attributed only where the alignment onto our timed stream is unambiguous. These are measurements of speaking style. We do not rank them: across this corpus, fluency and argument quality are nearly uncorrelated (ρ≈0.2), and smooth talking does not signal clear thinking. How it's measured →

Everything Dan Siroker said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

Assertion Supported
Siroker: Top VC funds will break ownership minimums for hot startups
“Yeah, the best investors benchmark and recent, they will invest less than their supposed minimums for the right company.”
Dan Siroker May 15, 2024 ▶ 29:43 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Disclosure
Siroker: Limitless rejected 22 $1B offers to accept a $350M Series A
“We had offers, actually, we had 22 offers at a billion dollars. We turned them down and took 350.”
Dan Siroker May 15, 2024 ▶ 37:51 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Investors' job is just capital and doing no harm
“The one thing that really kills me is when I see a founder playing the victim here and say, well, my investors didn't help me enough. Like, That's not their job. Their job is to give you money and hopefully do no harm.”
Dan Siroker May 15, 2024 ▶ 51:06 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Successful startups show glimmers of hope very fast
“Things that work tend to work really fast. You know, it was kind of this anti-pattern. Most people would say, well, you got to stick it out and be perseverance and, you know, keep, you know, banging your head against an idea and you have to keep executing it. …”
Dan Siroker May 15, 2024 ▶ 4:33 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: First-Time Founders Brag About Headcount; Serial Founders Brag About Lean Teams
“First time founders brag about how many employees they have, second time founders brag about how few employees they have.”
Dan Siroker May 15, 2024 ▶ 7:29 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Sales reps should expand organic product pull, not do cold outbound
“I would say when you feel market pull, when you feel the market, like I gave the example of Starbucks, you know, they're going past all of the processes, they're going past all, like they're seeking forgiveness, not permission to use your product. You're seein…”
Dan Siroker May 15, 2024 ▶ 18:47 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Job candidates bringing up titles in interviews is a red flag
“One thing I'll say about titles that I unequivocally believe is that if this is a something that a candidate brings up early or even during the interview process at all, it is a pretty red flag. It shows you kind of what their values are. The best people I've …”
Dan Siroker May 15, 2024 ▶ 22:11 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Disclosure
Siroker: Limitless raised existing salaries after hiring an engineer $30k higher
“We hired somebody, a great software engineer. We thought, wow, actually the market is showing that this person should be 30 K more than the other folks on the team. And so not only did we hire her at that price, but we also raised everyone else's salaries to m…”
Dan Siroker May 15, 2024 ▶ 24:01 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Disclosure
Siroker: Limitless let employees sell 25% of vested equity in Series A
“In our series A, we're way oversubscribed. We actually have, we raised our series A over a year ago and we haven't even started spending it. So we had far more investors who wanted to invest than we had you know, capital to sell them. And so I gave our employe…”
Dan Siroker May 15, 2024 ▶ 25:16 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Siroker: Limitless ships faster with 20 people than Optimizely did with 120
“With 20 people today, I feel like we're having a greater impact and ship faster than we ever could with a 120 people and software engineers at Optimizely.”
Dan Siroker May 15, 2024 ▶ 28:11 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Cap ownership sold rather than giving raise targets to VCs
“So instead of answering the question how much you're raising, The best answer is, you know, we don't need to raise, so we don't have a budget we're driving. We want to sell no more than this percentage of the company, and we're letting the market decide the va…”
Dan Siroker May 15, 2024 ▶ 40:47 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Founders should target VCs on the rising arc of their career
“I think the best investor you can have for your company is somebody who's on the rising arc of their career. You want a Peter Fenton when he's 35, not 45. You want, not, not going to be ageist, but you want somebody before they've had their first IPO, and you …”
Dan Siroker May 15, 2024 ▶ 48:50 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Assertion Partly supported
Siroker: Limitless raised from hundreds of investors, hindering competitors
“One of the benefits side, unintended side benefits of the round we raised I do think kind of made everyone else's job. Who's a founder trying to compete with us much, much harder because first of all, we had hundreds of investors.”
Dan Siroker May 15, 2024 ▶ 52:17 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Founders should always choose a down round over a structured up round
“If you're a founder listening to this and you're contemplating an up round with a liquidation preference more than one or a down round, do 100% of the time do the down round.”
Dan Siroker May 15, 2024 ▶ 54:54 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Pitch decks opening with market map slides are immediate red flags
“You know, like that's what you're looking for is this founder market fit around the problem, not somebody who's like a McKinsey consultant who said like, if their first slide is here's the market map and here's the market size and, you know, here's the niche w…”
Dan Siroker May 15, 2024 ▶ 1:03:11 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Asking for the highest valuation is almost certainly a mistake
“Always saying the highest price is almost certainly going to be a mistake.”
Dan Siroker May 15, 2024 ▶ 37:42 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Siroker: Only Three or Four Key Decisions Determined Optimizely's Success
“I have 10 years I put into my last company and I can recognize that really Only three or four things that we did made the difference in the success or failure of the company.”
Dan Siroker May 15, 2024 ▶ 9:24 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Disclosure
Siroker: Optimizely moved to enterprise too fast and abandoned solving churn
“Many, many examples of this, you know, from moving to the enterprise too quickly, to sort of not recognizing the core of what we had, to sort of abandoning The core problem of solving churn”
Dan Siroker May 15, 2024 ▶ 16:01 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Using founding engineer titles reduces early employee turnover risk
“To be a founding engineer is so much more meaningful to somebody, both in terms of their, you know, if, for example, if 80% of your friends are founders of companies and you are just a software engineer, but you started in your first employee, like that just p…”
Dan Siroker May 15, 2024 ▶ 20:54 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Startups should compensate employees at the 75th percentile in cash
“You can still pay, you know, 75th percentile in, in terms of cash, and it shouldn't be a huge lifestyle change just because they're joining a startup. I think that's a, you know, 10 years ago, that was this idea that you're exchanging, you know, risk for rewar…”
Dan Siroker May 15, 2024 ▶ 23:19 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Disclosure
Siroker: Why Limitless refuses to hire candidates straight out of college
“Like we don't hire people straight out of college. We hire people with experience.”
Dan Siroker May 15, 2024 ▶ 26:39 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Founders should concede on valuation in term sheet negotiations
“I think it's fair to give on valuation.”
Dan Siroker May 15, 2024 ▶ 32:46 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Disclosure
Siroker: Why Limitless operates without a board of directors
“I've been lucky not to have a board for Limitless.”
Dan Siroker May 15, 2024 ▶ 33:55 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Insight
Siroker: Early-stage board members struggle to gain enough founder context
“I do think boards as a company gets bigger and bigger and closer to going public are really important for governance and accountability. But when the company is so early on, it's very, very hard for a board member to get up to speed. You know, they're showing …”
Dan Siroker May 15, 2024 ▶ 34:38 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings

Show 24statements(30 left)

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Appearances (1)

EpisodeDateSpeaking time
Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of Coll May 15, 2024 57m
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