Dan Siroker
Co-Founder & CEO, Optimizely · Co-Founder & CEO, Limitless · Co-Founder & CEO, Rewind AI. On 5 shows, 7 appearances. The Shows tab opens the full record on each.
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.
5shows
7appearances
130statements
11resolved
8supported
0contradicted
73%fully supported
5said about them ↓ Everything Dan Siroker said on any show that made the record, most notable first. Each card names its show and opens the statement there.
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.”
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.”
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.”
Siroker calls Adobe's marketing cloud a poorly integrated 'Franken-suite'
“Adobe you know, has a product that, you know, has been evolved through acquisitions, which turns what they're offering into what our customers tend to describe as a Franken-sweet. It's a bunch of products that don't really integrate well with one another.”
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. …”
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.”
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…”
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 …”
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…”
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…”
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.”
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…”
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 …”
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.”
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.”
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…”
Siroker: Rewind raised Series A at $350M valuation with $700K ARR
“We raised it a three hundred fifty million dollar valuation with 700 K and ARR.”
Siroker: Rewind's 20-person team ships faster than Optimizely's 400
“We're a team of 20 at Rewind, and we're more productive. We ship faster than we ever did when I had a team of 400 at my last company.”
Siroker: Rewind's 20-person team executes faster than Optimizely's 450-person team
“Today we have 20 people and rewind we had 450 and I feel like with 20 people we're able to do more and execute faster and be More tightly aligned than and ship than we ever did at Optimizely.”
Siroker: Ex-Apple founders often fail to ship due to unrealistic quality expectations
“I see a lot of companies today that are ex Apple people who've built amazing things and they go off and they spend years and years toiling away and never really ship anything. And, you know, I think they have this sense of like, it needs to be As good as the l…”
Siroker: Thousands of multi-billion-dollar vertical LLM application companies will emerge
“There's whole categories of companies that are going to be cat, you know, Category defining independent successful big public multi-billion dollar companies that are just applications of large language models in a specific domain for a specific user with a gre…”
Siroker predicts 50% of work will be fundamentally changed within 10 years
“I think a lot of jobs will be gone in 10 years, but they'll likely be replaced with new ones.
I think that's probably an obvious
Conclusion.
I think on the order of probably 50% of work will go away.
It would be fundamentally changed.”
Siroker: AGI will eventually perform half the work of human engineering teams
“Eventually, you know, I don't think it will necessarily replace engineers, but it'll certainly augment them. You'll have plenty of, you know, half the work that an engineering team does will be done by AGI, and half will be done by humans, and the human stuff …”
The other half of the tape: Dan Siroker's own voice is left out of every number here. Other people bring the name up 4 times in 2 episodes across the shows. 1 statement on the record names them. every mention, with the transcript →
Who brings them up most Harry Stebbings 4
Statements about Dan Siroker, by other people (1)
Every mention by year
tap a year for its mentions
20VC 4
2024 4 mentions in 2 episodes 2 per episode
One line per show, most statements first. The link opens Dan's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| 20VCLEDGER | Co-Founder & CEO, Limitless | 1 | 54 | 67% 2/3 | full record on 20VC → |
 IN DEPTHLEDGER | Co-Founder & CEO, Rewind AI | 1 | 34 | 100% 3/3 | full record on In Depth → |
 FOUNDER'S JOURNALLEDGER | 2 | 22 | 33% 1/3 | full record on Founder's Journal → | |
 SAASTRLEDGER | 1 | 14 | 100% 2/2 | full record on the Official SaaStr Podcast → | |
 a16zLEDGER | Co-Founder & CEO, Optimizely | 2 | 6 | — | full record on the a16z Podcast → |