Dan Siroker

30 statements across 1 episodes · 13 bullish · 6 bearish · 1 people on the record · first statement May 15, 2024 by Dan Siroker · said 4 times in 2 episodes since 2024 · across every show →

On the record as a speaker too: Dan Siroker's record, appearances and statements → this page counts the times other people say the name.

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brought up most by Harry Stebbings (4)

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Everything said about Dan Siroker, oldest first

May 15, 2024
Insight
Siroker: Shipping features creates ongoing maintenance commitments, never single tasks
“I've never seen a situation where we'll ship a little feature and we're done. It's always like, oh shoot, now there's this edge case we didn't think about it. And then, oh, this other person wants to do this other thing. So you, it's like opening a commitment …”
Dan Siroker May 15, 2024 ▶ 1:05:32 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024 positive
Insight
Siroker: Marquee VC brands mainly benefit talent recruiting
“I think it helps with recruiting. I think that's probably the biggest benefit. You know, great, great talent can work anywhere, and if they had the choice between a company that's got, you know, great marquee investors who, you know, who've done their homework…”
Dan Siroker May 15, 2024 ▶ 51:44 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024 positive
Disclosure
Siroker: Why cutting hobbies and social life yields peak personal happiness
“I've cut out basically most of my, I don't spend much time with friends. I have basically no hobbies. You know, I, I'm reminded of this Rick Rubin quote. He's like, I have no technical skills. It's like that, but for my life, like all I do is spend time with m…”
Dan Siroker May 15, 2024 ▶ 1:09:55 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024
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
May 15, 2024 negative
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
May 15, 2024 positive
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
May 15, 2024 positive
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
May 15, 2024 neutral
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
May 15, 2024 positive
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
May 15, 2024 negative
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
May 15, 2024
Insight
Siroker: AI investors should prioritize problem-obsessed over tech-obsessed founders
“I think the most important thing to do if you're an investor today is find founders who are obsessed with problems, not solutions.”
Dan Siroker May 15, 2024 ▶ 1:00:22 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024
Disclosure
Siroker: Optimizely tried and failed to acquire Segment
“Another example is segment. That's something, another area where it was adjacent to what we're doing. We tried to acquire them. They were later stage. Then they said, no, they ended up being successful.”
Dan Siroker May 15, 2024 ▶ 1:06:40 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024 negative
Insight
Siroker: Giving early VP titles triggers company-wide title inflation
“Titles they're a bit weird because they're both kind of free to give in one sense, that it doesn't cost you more money, but they're expensive in that it creates this sort of, like, mutually assured destruction. You know, as soon as you give out that first VP t…”
Dan Siroker May 15, 2024 ▶ 19:51 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024 positive
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
May 15, 2024 negative
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
May 15, 2024 bullish
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
May 15, 2024
Prediction Not checkable as stated
Siroker: He would abandon Limitless hardware if software alone solved the problem
“We're building a hardware, we're building a wearable, If I can solve the same problems I want to solve without them, all for it. I'd be happy to do that. Hardware is hard. It's expensive. It's painful. I would happily give up hardware if I could solve the prob…”
Dan Siroker May 15, 2024 ▶ 1:01:24 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024
Disclosure
Siroker: Limitless ran all first investor meetings within one week
“Last year, when we did this fundraise, I we did this kind of in public. We put the deck out, and then for any of the people we felt were good finalists, we gave them a calendar link for the first meetings, and those meetings are all one week, so no more than o…”
Dan Siroker May 15, 2024 ▶ 42:21 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024 positive
Assertion Supported
Siroker: NEA Buys Portfolio Stock at IPO Rather Than Selling
“They're often buyers at the IPO. They're not sellers.”
Dan Siroker May 15, 2024 ▶ 37:28 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024
Disclosure
Siroker: How he negotiated 8% Series A dilution with Benchmark in 2013
“My very first Series A, I got, you know, I got benchmarked to agree to, you know, I think it was maybe eight percent or something.”
Dan Siroker May 15, 2024 ▶ 31:15 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024 positive
Disclosure
Siroker: Why he regrets not doing Y Combinator for his second startup
“I probably should have. I kind of regret not doing it. I think I was maybe too much pride and ego that I didn't need it. But YC has a lot of gifts to keep on giving, even if you're a second time founder, like work at a startup like office hours. So I am very i…”
Dan Siroker May 15, 2024 ▶ 1:07:55 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024 negative
Insight
Siroker: Founders should never accept over 1x non-participating preferred liquidation preference
“Never take more than One X non-participating preferred liquidation preference.”
Dan Siroker May 15, 2024 ▶ 54:01 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024 positive
Insight
Siroker: Back founders excited about smaller problems rather than social trends
“In some ways, actually, you kind of want to choose founders who are excited about smaller problems, because it tells you that they're not just falling in love with what they saw on Twitter or social media, that there's actually something they care about.”
Dan Siroker May 15, 2024 ▶ 1:02:33 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024
Insight
Siroker: Saying 'yes' to raising money creates a dangerous signaling clock
“Are you raising money? And my answer almost always is, is never yes or no. They want just a yes or no. Usually it's some version of, well, no, but if over the next week we get a term sheet you can't say no to, we're probably going to take it. So that's somethi…”
Dan Siroker May 15, 2024 ▶ 41:18 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024 positive
Assertion Not checkable as stated
Siroker: Peter Fenton gave direct contact info for 12 portfolio founders
“Peter Fenton, when I asked for references on him at the time, he was this amazing luminary. I asked him for references. He gave me 12 founders and CEOs, their phone number, their email. He didn't even introduce me, just to just reach out. And then I got this g…”
Dan Siroker May 15, 2024 ▶ 44:28 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024 bullish
Insight
Siroker: Ideal AI support startup CEO began career in customer support
“The best CEO for a AI customer agent is somebody who started their career answering customer support calls.”
Dan Siroker May 15, 2024 ▶ 1:03:04 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024 negative
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
May 15, 2024
Insight
Siroker: Hone pitches via 30 back-to-back associate investor meetings
“When you have like, 30 back-to-back associate investor meetings where you're practicing your pitch and tweaking the deck every single meeting, by the end of that, you have this really, really honed product, like a stand-up meeting.”
Dan Siroker May 15, 2024 ▶ 45:48 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024
Disclosure
Siroker: Optimizely tried to acquire Amplitude when it had four employees
“I tried to buy Amplitude when there are four people. In fact, they were about to raise their, I remember we're sitting at, I think at Chipotle and Soma with Spencer. And I, to this day, I'm so impressed with, I just, I was offering him insane amounts of money,…”
Dan Siroker May 15, 2024 ▶ 1:06:09 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
May 15, 2024 positive
Assertion Not checkable as stated
Siroker: Second-time founders can recruit far higher-caliber talent
“The caliber of person that I can hire today is far, far better than the person I could have hired, you know, when I started optimizing. So I do think that's a huge factor as well. You can hire much better if you, and certainly if your first company did okay, d…”
Dan Siroker May 15, 2024 ▶ 13:19 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
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