The Ledger
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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: 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: 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: 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: Asking for the highest valuation is almost certainly a mistake
“Always saying the highest price is almost certainly going to be a mistake.”
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…”
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…”
Siroker: Founders should concede on valuation in term sheet negotiations
“I think it's fair to give on valuation.”
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 …”
Siroker: Fast term sheets are designed to force lower valuations
“The investor who's giving you that term sheet wants to preempt it. They want to get in early. They want to get a better price, and so they know that if they do it before you're getting information from everyone else, that's going to help them.”
Siroker: Founders must maximize company control to protect common stockholders
“You as the founder of the company are actually As a fiduciary responsible to represent the interests of the common stock and that's your employees, you know, and so if you want to do best for your employees, you want to rationally control as much as you possib…”
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.”
Siroker: Founders should either be fully in fundraising mode or not at all
“I very much believe you should either be in fundraising mode or not.”
Siroker: VCs ask round size to implicitly negotiate valuation at 20% dilution
“When an investor asks, how much are you raising? More often than not, they're actually asking, how much do you think you're worth? Let's start the negotiation on valuation right now, because a 20% is what they want.”
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…”
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…”
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.”
Siroker: Tough questions from junior VCs signal intent to pitch partners
“Oftentimes, especially I found this too, when you very quickly can tell the person you're meeting with, they just, they have an inclination. They want to invest almost from the beginning and all of their questions you'll find out. I actually, I think are often…”
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…”
Siroker: Founders should never accept over 1x non-participating preferred liquidation preference
“Never take more than One X non-participating preferred liquidation preference.”
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.”
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.”
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: Technology does not automatically progress without ambitious founders
“Technology doesn't get better by itself, by the way. We could look at, you know, here's a good analogy, we could look at AI today the same way that Before SpaceX, people looked at the Space Shuttle. Like, hey, we had the Space Shuttle, then we retired it, and …”