Jason's AMA on Scaling Faster in SaaS at 2022 Annual

This is a live AMA with Jason M. Lemkin at Saastr Annual 2022 where he answers audience questions about scaling SaaS companies. Key themes: (1) intentional rule-breaking in growth (examples: Mailchimp, HubSpot), (2) a three-tier founder planning framework for goals (C10 stretch, C60 base, C90 conservative), (3) what investors look for in "elite" founders (exceptional insight, vision, and ability to be outliers), (4) handling Black Swan events and contingency planning (SaaStr 2020 cancellation, $10M loss, vendor quit), (5) fundraising trade-offs (avoid signaling weakness while fundraising), and (6) advice to take YC when it fills a missing "slice" even if you have revenue. The tone is pragmatic, anecdotal, and founder-focused.
Chapters
Please welcome Saster founder and CEO Jason Lemkin.
Hey everybody, we're not over. I think we have last call till 6 or later. But with only 250 sessions and 1700 brain dates we learned in Europa, some people have more questions. So I'm only here to help. We can line up. I have no agenda, but if folks want to talk about stuff and I can possibly help answer it, let's do it. But before we go, can we just bring out Amelia Barra who runs Sasser and just thank her for all her hard work because I think you did pretty good. I think it was the best Saaster annual ever, cross 10,000 people. All this made it. The reason this was the best one is Amelia does what the best leaders do is make it look effortless. So lots of respect. So thank you very much.
Thanks everyone for coming.
Yeah, so, and cheers to everybody. Thank you for being a part of all of this. So again, I've got nothing, although I'm happy to make up some things. But if folks got questions, come up to the microphone and if I can help, I'll certainly answer some or create a dialogue around stuff. What do people want to talk about? What's been your biggest lesson from Saskra the last two days? Wow, that's a trick question. My biggest. I should ask you what the biggest lesson is. You know, I think that I'll have to process that for a couple of days. I think, you know, it's interesting. When I started, when I was at sasio and even when we started, you know, one of the things we did at SAS was try to not just the number one goal was to share the mistakes that I and others made so that the odds were lower you would make them. But as time went on, we shared lessons. We shared lessons what best practices were in and customer success and revenue tension and all these things are right. We know what top tier NRR is and CAC and all of these things. But it was super interesting that the two big interviews I did were with Ben Chestnut from mailchimp yesterday and with Dharmesh and Brian from HubSpot. And it was interesting that they broke rules. And I don't mean in an edgy way, I don't mean. What I mean is Ben broke the rule that he didn't care what NRR and Churn were. And of course we need to care at some level. But as a bootstrap business, it was top line growth and bottom line. And he said it, you know, he said it differently, but it bit them a little bit as they got to 800 in gross, slowed, and most of us would be thrilled to get to 800 million and see the growth slow. So it did catch up. But, but he broke, he did break those rules. And the HubSpot thing today was. So they broke two rules, which I hadn't really thought through. They had low NRR all the way until 30. They were aware of it. But, you know, startups that I work with closely are invested in. If they got all the way to 25 million with 75% NRR, I would, I would tell them to quit today. Right. I mean, there's, there's a. And, and so it's, it's interesting that they, they were intent, they knew what they were doing. And then I hadn't really thought about how HubSpot went. They're now. And we didn't get to all of it, but HubSpot's in like, they have like five or six products. They have service and all this. But the second cloud for them was sales. And it really makes no sense because I've asked so many of the best SaaS CEOs that are public how to go multi product. If you read Saster, it's been a recurring theme. And the best one of all, if you didn't see it, we did it at one of our digital events this year was Spencer Skates, who's CEO of Amplitude, one of my favorite SaaS CEOs, and he did a whole one hour on his mistakes going multi product into their IPO. And his point that many, many of the leaders say is the mistake is trying to sell something that's really cool to a different buyer. Like they wanted to sell the Amplitude product. I forget who to sales or somebody else. And that was their mistake. And the learning is sell two things to buyers. And the fact that HubSpot did the opposite and sold a sales product to salespeople, Hooray. It started off freemium, but free doesn't make it any easier to sell anything, does it? So I think my learning is just know the rules, know the KPIs, they're all public. Find public comps and copy them. But it's okay to, like, get there a little bit differently or break a rule or two if it's intentional. Like, if it's. If it's intentional. So that's my big lesson from both of them. Yeah.
I've been thinking about goal setting a lot lately for organizations and teams, and there seems to be sort of two ways to think about it. One would be set ambitious, inspiring, impossible, Goals that have, like, low chance of success, but sort of drive an organization in a direction, but that you kind of expect to fail towards. And then the other is to set reasonable objectives that you know you can hit and that everyone feels good about when there's all greens on the chart.
Yep, whatever.
Have you noticed a pattern among, I don't know, the ones that end up on this stage where they go one way or another?
I think I noticed a pattern and I wrote it up a couple years ago and refreshed it. And then I'll add a new anecdote. You know, I wrote this years ago and then I've updated it of like the three plans you need to make as a founder. And I call them. No one's really ever copied this nomenclature, but I call them C10, C60, and C90. And C is the confidence factor and C10 is the big plan that there's a 10%, like a 2% chance you're going to hit it. Like, talk about that with your co founder over beers or rose. There's no point, right? 10%, there's a chance. So talk about what if we. If we think we could do 9 million next year. But look, if the stars align, we did a Google sheet. It's possible to do 12. That's your 10%. The 60 is probably where your core plan should be. We have a 60% chance, thinking we can do it more likely than not, but barely. That's how you build your core model. Your core model is for sales, for marketing spend, for hiring and engineering and product. And then with your finance person or yourself or your outsourced person, you build a C90 plan, which is one, we're 90% sure even if sales slow, we're going to hit this plan. And the advantage you don't. In my experience, the 10 becomes your stretch plan, the 60 becomes your base, and the 90 is the quiet plan you use to not run out of money. That's how you manage your burn rate. And not enough people do that. And then you look and you say, okay, if, let's say next year, you think you're going to grow 100, you think there's a chance you can grow 120, but there's a risk you grow 70%. I'm just making up the numbers. Do that 70% plan that you know there's a 90% chance you're going to hit, and sometimes you end up burning more cash than you thought. And so you've got to readjust that so you don't run out of money. So I like doing the C90s so that you know, you won't fail, you won't run out of money. 60 for the company and then 10 is the stretch. And then what's interesting is I don't know if you're at the last session with Sam Blond who was the CEO of Brex. He's done other stuff, but, you know, when he came out to our Miami meetup, I think in March, he did a great. And go watch it on YouTube. He did a great presentation on how to set sales goals for his team. And someone who's been CEO of Brex from like I think maybe 10th employee. So first sale, then he did it at Zenefits and he did it another company with me. He did it for me back in the day. Like these are insanely fast growing companies. He said even Tim, he wants 80% of his reps to hit plan. Right. So it's, it's hot. It's not the same point. But he, he wants a successful sales team, a culture of winners. So you need most people hitting it. So anyhow, that's my thought. You can look on Saster, but I really like the C10. C6 founders don't do it or they're lazy. And when they do it, their eyes always, always open when they do these plans.
And so the C60 is the one that gets communicated. The team is like on our base.
It'S just the base plan.
Yeah.
Okay. If you have more than a 60% chance of hitting it, it's not ambitious. Right. 90 is too conservative, isn't it? We're startups, but 10 is the crazy CEO. And then all the sales, the whole team quits when it's 10%. Right. So you can tweak those if you want, but they're like a Fibonacci sequence. Everyone kind of knows what 60 is. 10 and 90. And I think if you futz around, people don't instantly know what those things mean. Right. Cool.
Thank you so much.
Yep.
Great to be here. Jason.
Thanks for coming.
Yeah. Earlier when I talked with Aileen of Cobalt Ventures, you're talking about valuation, that kind of things. And you mentioned that elite founders could get better terms. And my question is, which are the characteristics of elite founders nowadays? How, how high is the bar right.
Now for elite founders? For. Yeah, I mean, I'll answer the question generally, but you mean specifically for raising venture capital or just in general?
Yeah, yeah, for raising capital.
I don't think the bar has changed. And I'll step back a minute. When I was running my last startup, Adobe Sign, Echo Sign, which talked about too much. But in my, in my batch of of founders for my series it was called the Be. Then A, B and A was Emergence Capital. So in my group was Peter Gassner who's CEO of Viva, which is worth 30 billion. David Sachs, who then was CEO of Yammer. Renee Lacert, CEO of Bill, which I think is where it was almost at a billion in revenue. Some of the best. And so I was like I think either the worst of the best or maybe the best of the mid pack of that group of CEOs. And it was correlated with the size of the outcome having a nine figure exit. They had 10 and 11. And so I'm rambling for a point. I realized quickly where I stood in the hierarchy when I met Peter Gassner Seal Viva and we did a great session way back at 2017 annual on, on YouTube. It's one of the best sester ones ever. I'm like this fucking guy knows like this is the best CEO I've ever met with Peter. And how did I know? It's not that he was had been the VP of Engine Salesforce or cto. It's not that he was smart and wise. It's that he understood my business almost better than I did in the first meeting and that was that that and he was so nice the way he said it. But that that level of insight I had, I'd really never seen. And then I met David Sacks at Yammer. Not when he was whatever all in pod dude. And I mean I love David but. And David was different than Peter, but he had this energy, this intensity to drive something off the cliff. And I'm like, I'm kind of, I have my own kind of energy, but not like David, like David's going to build something bigger than I'm going to build. And I met Rene from Bill and a lot of people didn't get Bill for a long time. And I wrote Sastervos when they went public. Our five interesting learnings. Like you probably never heard of this company, but the CEO is really good. And I met Renee and I really think Rene is one of the top 10 CEOs, but maybe for a different reason. I think Rene is smarter than me, but maybe not in the crazy way that Peter is. Rene had a 30 year vision even when I met him. And he'd done a startup before called Pay Cycle that had had a lot of drama into it. Bought it for 100, 150 million, which sounds like a lot, but there was executive turnover. And I don't think it was the greatest experience for him. I think he wanted and he did build because he had a. He didn't just want to do payroll on the Internet. He wanted to automate all the ways SME paid. And he had the same vision when I met him in 2006. He had it in 2008, 2009. And I remember with Rene, we were sitting at an event in Hawaii called the lobby in like 2013 and I'd sold. I was kind of investing and chilling and I'm like, Renee, who's running what a $20 billion company today, right? And I'm like Renee, how's it going 2013? He's like friggin hard Jason. He's like, it's so good to see you. He's like, no one understands SaaS. I can't find any great VPs. No one will fund me. Okay? I'm like, yeah, that's pretty bad my friend. But he's like, I'm on this, I'm gonna find a way. I'm on this 30 year journey. He actually had to raise, I think around at really terrible terms and prices at the time. And whoever got it got an insane deal, right? But then I saw someone truly on a 30 year journey, right? To revolutionize the way accounting bill payment, this network for SMBs. And he was such a visionary across two startups. And I'm sharing those stories to say the bar's always been that, right? And, and I will say as an investor, if you want, from an investor standpoint, I think I've done only 30 venture investments since 2013. The ones that did really well, almost all but one, they were like that, right? And you walk into the meeting and. And the ones you wish you had invested, right? And so, and so the bar has gone up in the sense that investors are looking for even faster growth. Investors are hoping for 100% growth at 100 million ARR. That's what you can back into today. And it's crazy. Investors want 100% growth at 100 AR. But the intangible piece that founder, that is better than me, that is better than even most people in the room. That, that's. I don't know if that is, that's what people want. It hasn't changed. It's that crazy thing, right? And like with Figma, talking to all the folks backstage that met. I don't even know him. He hasn't that met Dylan at Figma, they all say he was just off the charts from the Beginning, Right. And that could mean different things, but that's what they want. They want 100% growth at 100 million. And then a CEO at least as good as Figma. That's all the VCs want.
Nice.
Thank you. Sure. But one last point. Since we're changing, just so you know, why do VCs, why do they want Peter Gassner and David Sachs and Dylan from Figma? Look, I've written a little bit about it, but it's not obvious. Like it's just, just so you know, so you don't bang your head against the stage. It's so hard to make money in venture, right? Let's just do some quick math for fun, you know, on day three. But let's say you have a 4,500 million dollar venture fund to keep your math simple, 500 million. And you invest 10 million for 10% of a company. And it. And it sells for $300 million. Like that's pretty good exit, right? I mean it's not. How much do you make? 30 million. How much of your 500 have you paid back? You haven't even made 10% back. And the clock is ticking. Your goal as a VC fund is to do at least 3x and obviously more. So that 500 million venture fund has to turn that into at least $1.5 billion. One point. Now let's imagine you invested early in Figma. I mean, good God, 20 billion and you owned 1%. How much do you make? 200 million. Like you're not even halfway. Like you don't even get a thank you note from your LPs. Right? So I know working with VCs the later stage, it can be frustrating, but at least anything in the world, you want to understand their business model. Why do my customers act this way? And the VC thing, it's not just greed. It's just hard to make all that money back. And until you think about the math, you don't realize why. And I'll tell you one last story and then we'll break. But like, so I was, you know, my second investor again was Emergence Capital. I love them. And you know, I made them $30 million in two years. At the time I thought that was, that was great of me. Right? Then I go, someone shared with me their confidential returns. Okay, this was like a 10x fund. So I think they turned 250 million into 2.5 billion at the time. And I was like. And they risked viva and they listed Yammer. I'm like, where's Echo sign? Like I made you guys $30 million and it was in an asterisk at the bottom. All other exits, like I was amalgamated, I didn't even get a line in the emergence numbers. And it was like an epiphany. I'm like, okay, now I'm starting to understand how venture works. Like I get, now I get why people act the way they do because I was so small, I made them $30 million. I didn't even get a line. I didn't even get the bottomless line on the portfolio. Right. So that's why you can't make it so hard to make money. Right? Yeah.
Hey Jason, thanks a lot for the event. It's been fantastic.
Thank you.
So From a former SaaS founder investors perspective, like early stage startups, post MVP, post revenue, but you know, pre seed, where do you strike that balance between. You're trying to get product to market quickly, you're trying to get the traction to get the numbers to attract the capital, but you're going to have warts on the product from the mvp. You're trying to. Where do you strike that? Where do you see that balance struck? Where you start focusing more on the product quality and less on the speed. I mean it's kind of a hard thing. Is that something you would expect founders to be focusing on prior to their seat?
Well, look, I will say I'll answer the question in two ways. I'll answer it devoid of capital and then I'll answer it related to raising money. As a founder, this is a trade off. You're gonna. Were you at the session with HubSpot founders?
I was, yeah.
It was great. I mean, Brian said It took him 10 years to be proud of the product. So obviously that struggle is endemic to all of us as founders. Even if we're deeply technical, we never get the product we want. And if we have the sales guy leading the company, there's all these other issues and there's always feature gaps and everyone has technical debt and almost everyone refactors the product once or half refactors it and hits some sort of technical debt wall between 2 and 10. Most people don't hit a technical debt wall on customer one because it's like not a lot of load on the servers. But everyone goes through these trade offs. Right. But for raising capital, cry me a fucking river. Okay, I'll tell you the loserous thing and I'm not even gonna. I put a lot of things in quotes. I actually don't think this goes the loser is thing. As a founder, you can say To a vc, right? They make you sound like a loser. And I literally never use the word loser. Right? It's terrible. But it's true is we didn't grow that fast last month because we were fundraising as an investor. When you hear that there's not even doors here, you're gonna run the hell out the door, aren't you?
Right?
And for many founders, it's true. Like, it's so much work to meet. How could I meet 50 investors and also hit the plan when I'm the chief sales officer? Like, how can you, like, cry me a river? But you know who does it all the people I just described, right? They all hit the number when they fundraised and all the great founders. And I'm not saying it's easy. And it's not just hours worked, it's hard, right? But like, so operationally, this is a trade off you'll have for your entire. At least for 10 years, like at HubSpot, right? But for VCs, trust me, cry me a river, right? Because again, going to the prior point, if you really want to unpack VCs, like, I got into this a little bit with Alien this morning, but just. I know it's when you see the math that I described, you get it. VCs can only invest in outliers. You cannot make money outside of outliers. You just cannot make enough money. So any signals that a company might do great but not be an outlier, you've got to run for the hills. And the signal of I couldn't do it because I was fundraising, that's a signal that, like, more power to you as a human being, but you'll never be an outlier. Right? And so you got to quit. You got to quit, right? So don't ever. Don't look like a fundraising VC loser and don't let them see you sweat. And don't let the trade. Share the trade offs in a good way. Right? I'm proud that we not only hit the plan for the month, But I did 50 investor meetings like, oh, that I want to invest in her. All right, thanks for the question.
Thank you.
Hey, Jason, thanks for doing the AMEA and SASA 2022. The best ever. I have been here four days.
Good to hear. Thanks. If anyone on the team or Amelia can hear rock and roll. Four times.
Four times. Yeah. Well, I was here. I mean, I have a direct question to you. So I was here for Sasha 2020. I mean, the day I arrived is when I received the email saying that SASSO got canceled.
Sorry.
Yeah, so that's totally fine. I mean, like I was one of your supporters who were sending emails continuously to San Jose Convention center asking them to do a refund and stuff.
Thank you.
I have like two questions for you.
Yes.
One that was like a disaster, right? What happened last minute they went to the refund. I mean, everyone can come in and support you, but then you are being the leader. You are the one who is taking the heat, right. So how did you come out of this? Because this could happen to any business here. So when you have like the events as industry was like down. Right?
Yeah.
I mean like no one could do anything. And that was going on for like the entire year. You had to postpone even by like 18 months after.
Yeah, we lost $10 million.
Right. So how as a leader, what helped you to recover from a disaster like that? I'm just curious to know, like what was your mindset and what steps did you take?
It's funny, if you really want to talk about it, you know, did you hear the HubSpot one? Were you here for this? Well, so Brian Halligan, the co founders here, I mean, HubSpot's worth almost 20 billion. Brian, right after Covid drove, had a horrible snowmobile accident. Broke every bone in his body, almost lost him. And. And it's crazy. And you can watch the session later. It's great. I mean, he barely recovered. He looked, he's great now, but it was a long roll back from falling off a big cliff on a snowmobile in the dark and had to be airlifted out. And I think he broke 40 bones or something terrible. And I asked them the question after that, like, it's a black. But from a corporate perspective, it's a Black Swan event. Right. It sounds crazy. And my experience in my career, every five to seven years I've had a Black Swan event. And I asked them if there were others at HubSpot and interesting they didn't have another one. Right. But I can think back every four or five years I can think of one. And if I wasn't tired, I actually wrote a tweet and I listed all of the Black Swan events I've had in my career. And they happen somewhat, they're unpredictable, but regularly on the four to six year cadence. And so when Covid hit and the night came that Santa Clara was shutting everything down and we had to cancel it two days before, the team was beyond upset. Right. I mean, I mean, as a leader. Right. I mean, just action. And I was driving and pushing and Pushing. And we had to shrink from three days to two days as speakers cancel. And we had to do all these things, and we were down to, like, an afternoon event by the end. We had a core group of folks that still wanted to do it, and we still would have done it, right? And then the night before, I realized we had to call foul. Like it was. There was just no more way when this tweet went out that Santa Clara county was prohibiting any gathering, even though there was no Covid really in the US Yet. Then I realized, and then that minute. I'd had Black Swan events before, right? I want to give you another story at the end. And I went to, you know, Amelia, who you met, who. She was tough. I mean, the team was devastated. And I just, okay, we're. We're done. Let's. We sat down and for five hours, until three in the morning, we just planned out our best responses. And the team's better than me, and they're great. But I had been through the Black Swan event, so immediately I went into Black Swan mode, right? I just. Okay, it happened. I was. I'm not expecting it to happen, but boom. I know what you do, and you gotta flip the plan, and you gotta immediately be a leader in change. And I think if you ask, like, Puia, who's our number one sales rep, he's closed 28 million. He was. He's here. He's so great. I don't know if he's here right now, but he was just devastated. But he'd worked so hard, right? And he's like, I thought I was a crappy leader, but he's like, you were such a great leader through that because you were just. I don't know how you were so calm, but that's what happens when you've been through a couple. A couple Black Swan events, right? But related to that, there's an email. If I did, I put it. So I look for them now. And as a leader, as crazy it sounds, I think you have to look for Black Swan events. I think you have to look for them because you'll start to see them. And like In January of 2020, the CDC put out an email that said, Covid might be an issue for travel. And I wish I had it. I put on screen. I immediately forward it to Amelia and I said, my literally emails is, this is probably our Black Swan event this year. Because I knew the signs. I'd felt it before. And every year for Saster, there's. Except for this year, this is our best year. In terms of execution. But every other year for eight years, there was a little black swan event for us, right? Something blew up. You know, one year the person that ran it forgot to reserve the venue. That was pretty bad. Oh my God. Okay. Even this year, one of the big vendors for us.
Cool.
Quit three weeks ago. They quit three weeks ago. A key vendor that we've relied on for years, they just quit. They didn't want to do the work. Okay? So those things used to destroy us. We built redundancy, we built resiliency. So the minute that vendor quit after four years, Ashley from Montgomery Entertainment Office, she's one of the best that produced this. She just stepped up and Amelia stepped up and we fixed it, right? It wasn't easy, but kudos to her and she's not hearing this. Hopefully she sees my appreciation in the video. But so now I plan for them, right? And so I'm not saying you literally have to plan for a snowmobile accident or a pandemic, but. But you want to think what kind of things could screw this company up? What if the round doesn't happen? What if my co founder quits? Someone on your executive team is going to quit that you don't expect. And when I do, I don't ask these questions of the CEOs anymore. But I used to in the early days. You watch the videos, I'd always ask, was there a great VP that quit on you? And everyone has the story. Aaron Levy, a box, had this story in one of the interviews I did with him is how their first VP of Enght they would never recover, right? They lost their VP of Eng. He thought the world had ended and it probably had. And now I always plan for a VP to leave and like, you know, the ones that won't leave. But even then, something could happen, right? Something in their life. And so that's one that every founder should plan for, which is that one of your most trusted teammates for some reason leaves, you lose them. Like it could be a snowmobile accident for HubSpot, it could be a personal issue, it could be a home issue, it could be you don't realize how stressed they are and they just quit to go on a walkabout. But that's one if you plan for nothing else. Plan on someone, a key right hand person, that you would never think leaving, leave. And so have a calm plan. What would you do if they quit? How would you handle it? Think about it on a walk, when you're calm. So then when something like that hits, like losing 10 million like I knew, I didn't know exactly what to do, but I knew immediately what to do. We called the lawyers, we called the people, we called the vendors, like the folks that do this AV stuff. This is a million and a half bucks, these lights. So the trucks had already started rolling from Texas. We immediately called them and saved about $700,000 because the trucks turned around. I mean, that's a specific example, not to a SaaS company, but think about people. Black Swan events, Team Black Swan events. Don't spend all your time on them. But if you're going to go long, you're going to have a snowmobile accident or a global pandemic or friggin Twin Towers being hit by an airplane. I mean, I've been doing startups long enough to remember the day when the Twin Towers went down, right? And almost too morbid to talk about in the afternoon. I can keep thinking of the 28 in 2000. I mean, most of you weren't founders in 2008, 2009. It was so bad in 2008 or 9. I can't remember what. I'm sitting at an early SaaS, like corporate banking event at pebble beach on a beautiful day, having wine with like investment bankers or VCs and I get a call on my phone from, from our bank, Citibank. Greg, my, my banker for years to say, Greg, how you doing? I'm, I'm at this event, but I love you. He's like, you got to pull your money out of Citibank. I'm like, what do you mean? Citibank's the largest bank in the world. He's like, I think tomorrow Citibank's gonna fail. And Citibank, it turned out, almost did fail. Like Lehman failed. Citibank almost failed. And I'm like, Greg, where do I put my money? Like, do I put it in Silicon Valley bank? What if they fail? And he didn't know, he's like, at least take half your money out. Because everyone in the office is talking about we're going to do a press release tomorrow that Citibank's going to fail. Now there was a bailout that night and Citibank did not fail in the morning. But I'm just rambling through. Like I never as a founder thought my bank, my bank guy would call me and tell me to pull my money out. I didn't know where to, I didn't know the banks were closed at 3pm where am I going to wire out half of my 8 million of venture capital? Like I don't know. But so I could think of more of those. My co founder @echo sign 10 months in, like my muse walked out the door and never came back. Never came back. I never fully recovered from that. Right. And so anyhow, rambly. But think about those. When you're, if you're, if you're going short, don't worry about this stuff. Don't plan around if you're going short. Right. Don't worry. But if you think in terms of a decade, like Rene from build.com, calmly think about what you're going to do when these things happen. And then when they, when it happens once every five years, you'll like spring into action like I did. Right. So thanks for the question.
Excellent. Once again, thanks everyone. And thank you, Jason and team.
Yeah, thank you. Hey Jason, thanks for coming.
Thank you.
So Jason, come a little bit closer, could you?
Sorry, yeah. So if you are a founder in 2022, a first time founder, and you get accepted to YC, but at the same time you have a seed offer which. And you're under 1 million ARR.
Yep.
Would you go for YC or you know, skip it and immediately go to the VC stage?
I would, yes. Sorry, is that the question?
No, no. And like what's your thought process?
I've been through this. I've written a little bit about it on Quora, but maybe not on Saster. I think that. And listen, I don't work at yc. Right. I think if you're not sure, do.
It.
Because the YC companies I've invested in. Look, YC is expensive. It's a lot of dilution for a little bit of capital. When the earlier waves pre YC that did this back when I was starting my career, you see, they were founder rip offs. Okay, give us 7% for like one hour of a designer's time. That was like the biggest rip off back in the day. But YC is not that yc. And listen, I'm not into brands. I don't know where any founder I invested in went to college. But what YC is Stanford, Harvard, MIT and Caltech all rolled into one. And even if you don't learn a goddamn thing from the program, all things being equal, you might as well go to Harvard or Stanford or mit, right? Not that I care. I don't care and I went to Harvard. And maybe that's why I don't really respect it or even ask for founders I went to. But it doesn't hurt, right? And VCs, so respect it. Now look, there are like 220 companies in this batch, right? They can't all be the next stripe, right? There's got to be a few, a few that will struggle and a few dogs.
So.
But. But everyone's looking for signals in this world. There's too many startups, there's too many opportunities, too many companies to join, there's too many companies to fund. And the network at YC is powerful. And the first time I saw it, I was, I'm a small investor in front which just raised 1.7 billion. And I saw the power to Matilde going through it. I invested in Algolia, which is here, which is worth 3 billion. They were very seasoned French entrepreneurs that raised a seed before YC and gave up a lot to do yc and they will all tell you it was worth it to get them to the next level. And then later, for example, there's a company called treasury prime, which is a banking as a service API invested in. And the best CTO I know in the world is the CEO back in the day at Echo side Adobe San. I offered him half my stock when we were at 10 million to join me and half million a year and I would take nothing. He's that good. Okay, but he's a romantic. He didn't join me. We would both be billionaires if he had, but whatever. Chris, if you're watching this dude, I love you, but you should have taken the offer I made. 60 would have benefited both of us. Anyhow, so then he went and he was a romantic and he did a search company, great engineer, hard problem search, right. It didn't quite work out and he needed a job and I connected him with a great YC founder who was building a company called Standard treasury really early in banking Ape like way too early, but they got bought by Silicon Valley Bank. He made a little bit of money and anyhow, so he'd done this, he'd done another startup that sold for 200 million where he was the CTO. He'd had an exit, he was wicked smart and he wanted to be a CEO this time and run the whole show. And he seasoned. I mean, he's not old, but he's not young. And he had these wins and he could get VCs to give him the money, right? But he didn't have the whole thing. And I said, listen, just do yc. This will, this will create that missing slice that you're lacking, this confidence, this branding. And he's like, I don't know, I'm not The wrong guy for yc. I'm like, hold on, listen, I've never worked there. I'm going to write your script. And we practiced it and immediately he got in, in whatever, in 60 seconds. It's not that hard. He's like, hi, I'm Christine. I was co founder of Merced Systems. We were acquired for $200 million. Then I was the CTO at another company, YC Company, the Treasury, the first one Standard treasury, the Silicon Valley bank. And it became the core of their existing API. Now I'm running the whole show myself. I want to reinvent how banking is done in the 22nd century. I mean you'd fund that, wouldn't you? Yeah, pretty good. Yeah. So. And I've tried to give that advice again. And then most recently there's another one like Chris. One of the best ctos in my life, right. I will do anything for them. That's starting a company as a first time cto. He's had a billion dollar exit, another exit. Wicked smart. And he didn't have a lot. He had a little trouble raising money but it wasn't that hard, right. Because he's got in the grand scheme of things and I told him to do yc. I said to him look, you're going to raise the money but you're missing this slice. And YC is not magic, you know, watching a few things online and now we can do it online. And I love Gary Tan. I love all these stuff. I'm like it's not so much but it's going to solve this slice for you. And he didn't do it. And I'm 1000% sure for him it was a mistake. So if I had to distill it all down. If you think YC is not a good deal, a rip off. If you think you can raise the money, I'm sure there you know Parker from. Sorry, I'm getting tired. What's Parker's second company? Parker Conrad Rippling. Yeah. Parker will tell you to do it. He did it again. He didn't have to. Lots of folks will tell it to you. I say if you're like Parker, maybe don't like if you. Parker's. I mean it's different but if you don't think there's benefit at yc, don't do it right. If you're so far along you can, you think it's a cool brand but if you think there's a chance it will add that slice, that's the advice I give it, just do it. So if you're not. It's a rambly answer, but I think with some good examples, if you're not sure. I always tell founders, just do it. Even if you have the revenue, even if you have. If there's a missing slice, like, just go to Harvard, MIT and Stanford. Get it done and it's. It's worth it, right? Yeah.
Thank you so much. I think I need that slice.
Okay, then do it. Yeah, do it. Yeah.










