Scaling a Successful SaaS Sales Team w/ 20VC Founder Harry Stebbings and SaaStr Founder Jason Lemkin

This content was created by Jason M. Lemkin. This content was uploaded by Jason M. Lemkin. This is a YouTube video titled "Scaling a Successful SaaS Sales Team w/ 20VC Founder Harry Stebbings and SaaStr Founder Jason Lemkin". It features a conversation between Harry Stebbings and Jason M. Lemkin discussing various aspects of building and scaling a SaaS sales team, including hiring strategies, founder involvement in sales, and investment strategies in the SaaS industry. The discussion also touches on the challenges of founder burnout and the dynamics of venture capital funding.
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Jason, this is such a joy to do, my friend. It's been such a long time. I'm so excited to have you here, but thank you so much for joining me, Harry.
Thanks for getting us back together. I'm very excited.
Listen, it'll be a great one, but I do want to start with a little bit on you. I'd love to set some context. A lot of people know the Sasta brand, but how did you make your entry into the world of venture and come to found Sasta? Let's start there.
Yeah, I mean it's a long time ago now, but literally 10 years ago of my cohort of SaaS founders, the Aaron Levy's, the David Sachs is the others, I was the first one to have a half decent exit. And so when SaaS was harder, when Cloud was much harder today when there were one unicorn called Salesforce, I was the first one that didn't have to pretend, that didn't have to always claim every day was great. And I just started blogging my mistakes and that, that that blog took off and then one of the VCs that had invested in me, Storm Ventures, brought me in as a partner. I'd never done any investments before, but I just invested in some of the founders that were fans of this astro blog and it worked out okay. Like, you know, the first four investments eventually became unicorns, five out of the first six. And so it kind of took off organically, but I certainly didn't intend to invest out of that or build a huge community. It was just to share my learnings and mistakes when I had nothing to hide.
Can I ask, when you look at those five out of the first six, I mean I know the company is that it is an incredible cohort of companies. When you look back at that, are there some lessons that you have from those early investments that you take with you today and impact how you think about investing today?
I would say two things. One, certainly especially in the last 20 months, the world has changed, right? There are just so. The funny thing was back even five or six years ago in SaaS and Cloud, like you could meet with every good SaaS founder. I remember, I remember waking up when I read that Mamoon had invested in Slack back in the day, I'm like, I didn't see that deal now like all the 90% of the unicorns, I never heard of them, right? The universe is so big. So that's changed. The sheer scale of the cloud obviously is 100x what it was five years ago. A thousandx what it was ten years ago, which is difficult to wrap your brain around. So that's changed, right? You were saying, you were saying before we went on some great deals you missed, you should miss tons of deals today because there's too many good ones, right? I'll tell you what hasn't changed when I look back over the years is you've got to be crazy to be a founder and build a Decacorn. You have to be crazy. It's so hard, right? It is easier today. Let's be clear, it is easier to build a SaaS company today. The tools are there, the systems are there, the markets are larger, right? They're more understood. But the best ones, the Decacorns and the unicorns, these founders were insanely committed to, to building something huge in a way that almost doesn't make rational sense. Right? And Harry, you have a little bit of that with the 20 empire. I see it. That's why I've always known it would be wildly successful. But when you don't see that, my rule is, and I've made this mistake since, don't invest. No matter how much you love the found, you can love them as humans, they can be doing very well. But if you don't have this crazy 20 year commitment to building something huge, it's hard to make money in venture.
You know, the one thing that I continuously hear from VCs is the markets are a thousand X as big or 100X as big as you mentioned. And so ownership doesn't matter as much anymore. How do you think about that?
I think it's a great argument on a spreadsheet, right? Certainly owning 2% of a data dog 1%. And we look back, we look at all the individual investors in Uber that became deca millionaires out of you, like, wow, I could have done that. I don't know, I'm not smart enough. But when I look over my, you know, eight year history of investing, it's the ones with the double digit ownership that move the needle. And for better or worse, when I've had my own fund, when I look at what the port, the companies I'm sitting on today, obviously you regret ones you missed or you didn't. But all of my core positions are double digit ownership, largest investor in most of them. And that one puts you in a good position if you get a unicorn, right? Owning 20% of a unicorn still works today. If you give up a Decacorn, it was a miss. So I guess it all boils down to, I think there was one rule when I started investing that the folks I worked with thought was disagreed with vehemently, but it certainly turned out to be true. When you meet a winner. When you meet a winner, you buy all the shares. Now, if you can buy a quarter of the company, you buy a quarter of the company. If you can buy 2% of the company, you buy 2% of the company. But you either buy all of them or none. And, and I think that's the way you solve through this. Right? And if all you could buy was 2% of a decacorn and you get 200 million, that's, that's, that's pretty good. But buying less doesn't help, right?
Would you agree that ventures less collaborative now than ever before? Someone said that to me on the show the other day.
Without question and without question. It's better for founders. Without question. Every element of venture, that is. And I'm being binary when it's of course more subtle than this, but every. Much of the collaboration in venture did not benefit founders. Right. The fact today that the craziest thing to me in venture isn't anything you're saying. The craziest thing to me in venture is there, there are over 100 founder and operator led funds of over 50 million. That means if you are connected. If you are connected. Okay. And this is, this is for the privileged. Okay. Which we could talk about. But if you're connected, you might not Never need a VC until series B. If you can raise 10 million from founder led fund operator funds, rolling funds. And that works for you. Like you can get it done in a week or two. Like, why would you deal with a bunch of collaborative VCs that all want to own 15 or 20% of your company when value is not consistent with ownership? Right. That's the underlying tension that we've been talking about for years, but we're realizing is we get value out of our cap table, we don't get value consistent with ownership.
I totally agree.
Yeah. And for me it's hard. I'm sure it's hard for you, Harry. I get so many inbounds and they're like, jason, would you join our round? We have 100 or 200k left and I can't do it. Right. Because they're asking me to recruit their VP of Sales, build their team for less than 1% of the company. And if I was angel investing, I might do it. And if I had time on my hands. Right. But I can't do it. I don't. You get so overloaded. But That's a smart thing for a founder to do. That's a smart. And if the founders can get a great operator, a great cmo, CRO, ex founders with time on their hands to all. To all do this. I mean, it's amazing. And I invested in a lot of French startups. Algolia's and France and Gorgeous and Plato and it's interesting Olivia from Datadog would invest in all of them. Back in the day, they all knew him, he was a hub, right? And Datadog went public. He got a little busy. But back in the day, he was so helpful on every cap table. Why wouldn't you want him for 1% versus some fund that complains that, that, that the board meetings are inconvenient for his schedule? Why wouldn't you want Olivia in your cap table? Of course you would. Right.
I'm totally with you. One final question before we dive into the meat. And it's like bluntly, when we look at funding environments today, I call it the foie grasing of startups, which is like, especially in SAS. This worries me because you give a founder 60 million when they're at 25k MRR or 50k and suddenly they hire 20 sales reps, 10 in marketing, and they don't have a playbook, have repeatability. Do you see this too? And are you as concerned by it as I am?
I don't. I'm not concerned by it.
Huh.
I believe that with help. And this is why you need good advisors. You need good capital. You know, the best founders eventually hire great VPs, okay? Sometimes they screw up a few VP hires. Sometimes, oftentimes they'll fall in love with the logo. They'll want someone from Datadog or Dropbox, whoever. Everyone makes that mistake. Maybe your advisors help you avoid it. But the great VPs, the truly great ones, not the good ones, the great VPs know how to spend the money, okay? The mediocre ones fall into a hole. What happens is you hire a mediocre VP of sales and let's say, oh my God, the CEO promised we're going to go from 1 million to 10 million this year. That's what I promised when I raised the money. I didn't promise 1 to 2 or 1 to 3. Even 1 to 3 was the old days was a lot. I'm promising 1 to 10, right? And we're seeing at least 1 to 5, 1 to 6 all the time these days, right? So I did the promise. What does a mediocre VP of sales do if there's 60 million in the bank. They spend it all. They spend the mediocre ones. 100% of them spend it all. The marketers spend everything. Okay, we see it, Harry. You and I have seen it multiple times. A mediocre CMO will come in or just a misfit, a mismatch. More often, it's a mismatch CMO and they'll spend everything on advertising and media. But the great ones, you know what? They spend maybe 50% more. The great ones don't hire crummy reps, the great sales leaders. Right. They build amazing teams. Right. They just might hire a bigger sales enablement team, a bigger rev ops team to support them. Right. Than you otherwise would. The great marketers don't spend money on. On programs that don't perform. Right. So I think this is true. But I blame the CEOs for, for lowering the bar on hiring for VPs. I don't see them blowing through all the money. I never see it. I haven't seen it.
I think you're right, definitely in terms of the best, always hire, you know, the best vp. So I get you that. I do want to dive into the meat of the show though, because, you know, I think obviously one area where we're both very passionate is sales. And it's where I get the most questions, I think from founders in particular. Start on the matter which is like, fundamentally, does the founder need to be the person who creates the first sales playbook or can that be distributed to a sales rep or head of sales?
Well, look, I think I would say the majority of B2B companies that, that are successful that you and I have worked with, Harry. The majority, but not all. The founder has been the first head of sales. Right. You know, my first deck of Corn Saster podcast. 001 you did with Tiago from Talk Desk. Right. He was the only salesperson through the first 2 million of revenue. That's where I learned.
Right.
On the other hand, sometimes it's just not you. Right. Sometimes you cannot be a great sales rep. And when I look at my second investment back in the day, another unicorn, Algolia Nicholas, who you've, who you've interviewed was okay at this, but he brought in Gaten like his chief business officer, really, as almost a late co founder, he was probably employee number one or two because these engineers just weren't great at sales. And it became clearly that the search API had a sales element. Right? So that was the. If you don't have that DNA, find that great almost co founder like Salesperson early and it can work. Right? But hiring that person over Craigslist, right, or over LinkedIn or whatever, that, that's the one that, that, that, that fails. Right? So we all believe in this early founder led sales. And it's true most of the time, but it's not true all the time. But you sure better found a co founder like person to pick up the slack.
Okay. If you think about kind of the first sales hires, often founders who say they've built the playbook and they're at a million an error or say whatever, some number they go, should I hire a head of sales who brings in the team around them and crafts that team or should I bring in two sales reps and build it from the ground up? How do you advise founders in that situation?
Well, again we have, we've learned over time there's the scenario that works 80% of the time, but you don't have to run that playbook. Right? What works 80% of the time is 80% of the great cloud SaaS. CEOs we've worked with, they hire two quirky sales reps and get them doing pretty well, hitting quota or beyond. Often one of them just crazy good. Right? And we can talk about what that Persona looks like. Right? And when you've hired two, you're generally ready to hire a VP to hire three through 300. You have just enough of an engine, just enough of a playbook. Just as importantly a playbook that works that you can start reproducing that playbook from 3 to 300. If you, if you don't have those two AES and you hire a VP of sales, 80% of the time it doesn't work because there's nothing for them to work with. Right? And the good ones, and importantly today a good VP of sales usually won't join a startup of that phase. That's one thing that's changed the last five years we could chat about is the great VP of sales are waiting for 10 million. The ones that used to join at 1 million, they're all waiting for a 10 million ARR startup today or a unicorn, whichever comes earlier.
All of them.
So, but, but if you possibly can get two performing reps yourself, it's going to make that whole process 10 times easier.
I want to talk about those two reps. You mentioned that. What do we want in those two reps?
What do they look like?
What are the character types? What makes you go, this is a 10x rap and we want you in our team?
Well, let's be clear, the 10x reps in the early days are not the 10x reps later. Hopefully they stay forever. The best ones stay, if you're lucky, keep them. Right.
But.
But they're different. But I will tell you how to hire them and what they look like. Cause they're two different things.
Okay?
The 10X sales rep in the early days has one and a half criteria. It's really this simple. Okay. First, make sure they've sold at your price point at your ACV. If you're a 5K ACV startup, do not hire someone from a million dollar a year group no matter how much you love them. It's the wrong toolkit. Right? The toolkit is roughly the same for every startup at a given ACV at a given price point. So make sure they've sold every in cloud, in SaaS at your price point, okay? Otherwise don't fall in love with them. 2. And most folks screw that up. The second one, all the founders screw this up. Harry, would you buy from her? They listen to the buzzwords and they listen to the talk and they do the reference check. But if, Harry, if you've sold the first hundred copies of your product, if you've sold the first 200 sponsorships at 20, you know whether you can trust these precious leads to somebody else. And whenever I talk with the founder and I'm asked, how did it go? Well, my first two reps didn't work out. I'm like, what happened? And I always ask them one question, what would you have bought from them? Would you buy your. The answer is always no. So you can give on a lot. You can give on the fact that they were never great, that they were always mid pack. You can give on the fact that they sold at a six tier competitor. You can give on the fact that they, they never got to 20 million in their whole lives. You can give on a lot of things. ACV is tough to give on. And the fact that you would buy from never works. Okay, that's. And then, so that's the criteria, okay? And then I'll tell you. And if they just pass those two criteria, they will work, okay? They will work for you and they can stay for a decade. Now I'll tell you what makes them 10x. What makes them 10x and took me a long time to figure this out, is that they can change their playbook. 90% of sales reps and this works out, the bigger you get, they sell exactly the same way. Okay? Harry. Hi, this is Jason from 2020 Media. We have a podcast sponsorship we started. $100,000 a month. Where can I send the PO right now? When 20 gets beat really big, that actually will work eight times out of 10. But think about the early days. I mean it wouldn't work. And this and 90% of 89. Actually 90% of sales reps, no matter how they just run the same playbook again and again and again. And the bigger your brand gets, the more that works. But the great ones, especially in the early days, they change the playbook based on who the prospect is. And that may sound obvious because as founders we do this intuitively, but it's not how great. Many great reps are trained. They're trained in a process, in a system. They get really good at the 10 questions in the script. So those early reps can be great. Just if they're at your ACV and you would trust your lead, that's enough, hire her. But if they actually can sell three or four different use cases, they understand the different buying Personas already.
They.
That's when the magic, the magic just happens and you get the 10x er, that's. And that's the criteria of every top rep at any SaaS company I've talked to is they can completely change the sales playbook based on the prospect, based on the buyer.
Can I ask one thing? I find very, very challenging. It's like quota creation and say, how do you advise on the right quota? That is both ambitious and it's hard to get, but also it's not too ambitious where it's just too far out of reach. What's the right balance?
Well, let's. The good news is the middle is hard, but the beginning of this process and the end are easy. Okay. When you're really early stage, your quota should be enough that the sales rep won't quit that they can eat. So you need to make sure that at least the first three to six months, if you're sub 1 million to 2 million in ARR that they get a boost. Okay. And often, often it's simplest to almost give them. I know it sounds can sound crazy sometimes it's almost easy to give them 100% of what they close. If it's hard, right, you close 10k this month, you take home 10k. Like it's really simple, right? Obviously that's not profitable, but it's almost 100%. Like they take home 100%. That can be okay for the first three months. You have to train people, you have to onboard them. It's not the end of the World doesn't work at scale. Right, but you need to back into it. Okay? Here, I've hired this new, this new repairy. He's got to make 100k a year. Let me be honest with myself. If he can close 200k, it's so early. That's a gift, right? So I'm going to pay Harry half of what he closes that, that turns out to be. If you don't, you have to be analytical. They have to eat. And then at scale, we end up at these 3x4x5x numbers, right? Which is quotas are an SMB. Usually 3x your full, your, your fully burdened comp, your on target earnings. You ot up to 5x in the enterprise. So that's the way it works. 3x 4x 5x. It's actually worked since in the like it's, it was all. It's always been 3 to 5x of profits going back to automobile sales. Anything you could sell, right. Pool supplies. It's just because software approaches 100% gross margin, sales reps could keep 3 to 5. This 3 to 5x work for revenue, right? Not, not, not the profit. But that's the way it works. So at scale, if you want to make $200,000 a year as a sales rep, great. In SMB, you got to bring in 600 mid market, 800-enterprise a million. And then the question is in the middle. In the middle as you, especially if you have capital or if you don't, where do you want to bend those rules until you're at scale, Right. But ultimately, at some point, as you approach IPO or something, your metrics have to be normal, don't they?
Absolutely they do. My question is also like when you look at enterprise, given the conversion length in terms of the sales cycles.
Yes.
It's very difficult to know if your reps are actually good. How do you think?
It's very stressful.
How do founders know?
Very stressful.
What are signs then? When you have a founder that goes, jason, they haven't closed anything. But they've only been here four months. How do you know if they're good?
Yeah, there's a startup I invested in. It's taken a while. They're founded in 2017 and the beginning of this quarter they were at 2 million. Okay. Since 2017, this quarter they finally closed a million. So 2 to 3 million in one quarter. Not a single enterprise rep has ever worked out. You keep waiting and waiting and waiting when you're at scale, you know, because long sales cycles don't matter at scale north of 20, 30 million in revenue, you're lining up so many deals at the same time that long sales cycles don't matter because if you have a hundred deals in flight, it actually starts to happen very predictably. Right, but you need like a hundred long sales cycle deals. Not, not, not Sony baloney pipeline, but actually in flight that are going to close before, before this gets de stressed. And how many Startup founders have 100 enterprise deals in flight? It takes a while. Right? So there's really only two answers. And it's stressful. There's no great answer. One is I found that in true enterprise, like real enterprise, the founder is often the VP of sales until 10 million. I've seen this again and again and again. Now I'm not saying they don't have a VP of sales. Okay. But I think in SMB you can be hands off at a million or 2 in revenue as even if you did founder line sales. I find that an enterprise, they're so good at speaking to the big customers, they're so trusted. Right. Harry, we know like we trust him, all the customers trust him, Google trusts him, whoever trusts him. And, and so Harry is already in every deal until this brand is so established that Harry just gets pulled into the deal. So I actually think to tell founders that are pulling their hair out in enterprise, keep pulling it out because it's not going to get better, it's just going to get more repeatable and you will be the head of sales until 10 million. And so what that means is the big mistake that I see founders that are true enterprise make is they just have too much faith in these A's. You have to see more progress. You have, you have to judge it. And even if you have a nine month sales cycle, you have to say four months in. Are these deals really moving at the pace they did when I run them? Are they really working as well? Because otherwise it's fake, right? It's fake.
Energy isn't totally is the thing I worry about is like founder dependency. And I think about this with me now dealing with sponsorship management. It's like how do I extricate myself from the process? Because you don't want to be in every process where it's founder dependent.
What would happen to SpaceX if Elon Musk was gone or Tesla? Founder dependency is part of the game. Yeah, I mean it's part of, it's part of the game. Right. I think it's a, it's one of these existential risks for investing too. Right. What if something happens? Right. I got an email over the weekend from a great, literally one of the best founders I've known my entire life saying, you know, his co founder is kind of transitioning to an IC role. Right. I'm like, God, that's high risk. That's higher risk than losing a customer or some sort of other existential issue, right? Because a founder dependency, it's an existential problem. And you got. Making yourself obsolete is the dream of every founder. But maybe you could only come close. And it's true in sales. And when I started doing these faster events, I would interview all the CEOs in the early days. I would ask the Jeff Lawsons from Twilio and the Peter Gassner from Viva and I would say, how much time do you spend in sales? Like in the early days before they were all bigger and they're like, more than ever more. I'm like, really, Jeff, you just went public at Twilio in 2017. You're spending, you're a developer focused company, you're spending more time in sales than ever. Yes. Now sometimes that means more time with customers. It's not always prospects, Right. As you get bigger, you talk about 10 year customers. You want to move your time as CEO more to customers and prospects, but it never goes down. And I think that's emblematic of this level of founder dependency. Right?
Speaking of the founder dependency, have you ever had it where the founders just tired? We've seen Covid, we've seen the world change and shift in ways that we never expected. And I think depression, mental health, tiredness, to get chronic tiredness is more and more a problem. Have you ever had it where the founders burnt out and how do you deal with that? Because that worries me.
I would say only 80% of the time. What I mean is one of the very first things I wrote in Saster, literally probably in 2012 or 2013, a long time ago, was I've been doing this for five years, my startup's doing pretty well, I want to quit, I'm tired. What do I do? I've updated version of that over the years. Literally last week I had a conversation with a great founder that almost wanted to throw and throw in the towel. And even though they had over a million in revenue, it just taken a while, right? And mental health and everything, these are important issues. I wish I had any answers there. I'll tell you what I've learned more tactically about this topic, which is one, every, every company, every start, every SaaS, company, SaaS is good in that you don't have to change the product like every week.
Okay?
You're not con. It's not. It's not Clubhouse or TikTok. The competition level is. It's visceral, but it's slower. But you do need to reinvent yourself every four to five years, right? As a product. And the only way you can do that is if you kind of reinvent the team and your mission every. Not your mission, but your strategy every four to five years. And what bails you out of tiredness again and again if you get bailed out, if you do, is that magical VP that you find. That is more than a vp, that is almost like a founder. Almost like a founder, right? And that is the only thing that has saved me over time, and that is the only thing that has saved me even running Saster, is finding someone that would join and own more of it, take over some of that burden. And if you're a founder and you're burnt out and you're up to here, right, but you find someone to take over a piece of it, all of a sudden, everything's down here. It's just your stress level and everything drops 34, it's not to nothing. And then you'll realize, I should have almost dropped everything to find her, right? To find this VP that could carry some of the load, right? And again, when that founder sent me the email over the weekend, the first thing I'm going to talk to him about is, okay, who can we find on the team or outside? They can carry some of the load, right? Because the startup's doing great, but you need someone that's going to put some of those concrete blocks on their back and own some of this, right? And back in the old days at Echo Sign, Adobe Sign, I had three of those and I didn't appreciate how great it was. I didn't appreciate. I thought I needed that out of every VP, right? And. But I only had it out of three of my VPs. And then I realized I was an event and I was backstage with Wade from Zapier and we were talking about it and he's like, you're lucky if you have half. I said, what do you mean? He's like, you're lucky if half your VPs not only do their job well, Right. But do more than their job, like carry some of that load. And if you can even have half of your management team do it, that. That's like magic. And I realize he's right, right? And so that's. What if you're tired. That's what you're missing. You don't have someone to carry the load for you. And people, great people will do that, right? And that's what's crazy about startups is people get these emotional attachments to them and they will, they will do things they would never do in a big company.
Does that mean if they, if they don't carry the load for you, they're not great? They could be good. Does that mean you don't have them in your organization? Like you can only. No.
I think Wade's point was, look, I'm like, we didn't talk about any sort of person. He's like, I'm lucky to have a VP of marketing that hits plan. That's enough. Okay? If you get me the, whatever the goal is, like that's, you're going to have VPs on your team that are going to hit their numbers. And that, that's, that's hard enough as it is, right? A lot of human beings, especially as you get bigger, right, and it becomes more process oriented, they don't want to worry about the competition and where the, where the company will be in 10 years and the deep future. They don't, they don't. And that's, that's okay. That, that's okay. But, but having even half your management team care 80% as much as you do, that's when you can just blow it out of the water, right? That's when magic happens, right? And so I think it gets harder as you scale as these, as you hire process oriented people. But you can find them, but you need them. But if you can find a couple of these before even 20 million, the romantics exist. They're romantics. They're Romantics. They're romantics that want more out of life than a salary or even RSUs or equity to big company. They want more, they want a sense of belonging, a sense of worth out of their company. And you can mock that, but it's incredibly powerful when they get so much value out of creating themselves, out of being a creator, out of the magic of a startup. And if you can harness that authentically, that's when magic happens. That's the beauty. I mean, I don't know why, I mean you've had an interesting career, Harry, but I, you know, when I, when I quit my first so called corporate job to do startups, I actually had no job, no salary, no savings or anything. But it was wanting to be part of something bigger, right, than me that I did it. And I Don't think that's changed. That's why people join early stage stuff, right? Because it's not rational, is it?
No, not rational. In many cases I was just unemployable. Jason, actually.
Well, you're unemployable, but you're a romantic. And that's what I, when I say this to people, they don't understand what I mean. But I mean these, some of these great early stage and I mean early stage, almost up to 20 million these days. They're romantics. They want more out of life. They want to be on this special journey. Right. And tap the right person, that desire. If you're giving them that special journey and they want to be on a special journey and they're great, then they're super great. Right. Then they're magicians.
Totally. And if anyone listening is a VP running media companies and wants to help me, then please, you get it.
I mean, 20 is so big, you get it that you're overwhelmed now, right? And it may take you two years to find that person, which sounds horrible, right? But when you find that person, magic will happen.
Speaking of like not getting out, but finding leverage. But I am speaking about getting out now. You know, I was speaking to a sass investor the other day, Legendary Sassan said, pricing is so ridiculous today. Harry. For my early bets, just, I'm getting out of as many of them as possible. Honestly. Like bluntly, I know that average companies and their price is 600 to a billion.
Yes.
Sell secondaries. How do you feel about when the right time is to get out? And is this the time now to be selling?
You know, I, I have been thinking about that a bit lately because you do need to think about that. Right? The, the, the quality of unicorns is not consistent. Right now that this 100x air thing startup has become a meme. It's justified behavior that I think in the aggregate will work out right. For large investors. But on specific deals can make no sense. Because 100x air completely makes sense for a data dog or a snowflake. Right? No argument because. But, but basically 100x error startup, I has to at least quintiple next year with high quality revenue. At least quintuple. Right? And a lot of these folks that get these crazy valuations, the next year is not as good. It's okay. It's not that it's terrible or they would never get the valuation right, but it's not. They're not quintupling or sex tupling or septupling the next year. And then a set of issues set in that compound. Right. And you know, you have to understand what's going on. Is this, is this a generational company, right. Or is this a moment in time? And I think it's. It might be if you're a great vc, that's easy to. An easy bet to make. It might be if you're great. Your job is to know the difference. Right. And do I have a HubSpot or not? Like what do I have on my hands?
I have one the other day and it was a thousand X revenue.
Yeah.
I mean it was like a 50k startup MRI and it was done at 610.
Yeah. And it sounds silly, but I, but whoever led that round, if they're smart, they're doing 30, 30 of them. Okay. So then you start to see this bell shaped distribution and if they do okay, on the long tail of it, right, they're going to need four or five unicorns, right. Of those 30 to make it work, they're probably going to need more than 10%. They're probably going to need 15% to be decacorns. If you plug that into a Google sheet, you're going to see that they can write off three or four at the bottom. A couple can have mediocre outcomes as long as they get at least 15% to be decacorns. Right. And it's just, and you can argue, you could argue that given all the unicorns, all seed is still underpriced today. I think Seed, as crazy as it sounds, might be the only bargain because. Or pre seed like we have to. Pre seed might be the only bargain because as expensive as it is. As expensive as it is. And I'll tell you the problem with Precede next, as expensive as it is, it may not have seen the same inflation as Series A. Right. Even though it's seen inflation. Right. But tripling is not the same thing as 20x.
It's not my question. I don't think that we're going to get onto the problems, but I don't think pre seed actually exists anymore. Bluntly, for the majority or not for the majority, but for a lot of founders, whereby if you come out of a top Facebook, Twitter, datadog, Slack, you name it, you can raise 3 to 5 on 20 like that.
But what about the less privileged? Harry, that's what we're, we don't spend enough time talking about. I'm not even talking about less represented or truly underprivileged. That's an even larger issue. I'm Just talking about great folks that didn't come out of Facebook, Twitter or Y Combinator. Right. I would say most of my best investments did not. And those have not seen the same level of pre seed inflation. Right. But they have seen enough that can break the seed model.
Okay, talk to me, what do you mean break the seed model?
There has been a classic seed model in the US where for at least a decade, if not longer, of like 40 to 50, 60 million per partner. Right. That's been a seed model for a long time. Three partners, 180 million to 120. When I could be a solo GP, which was seen as insane at the time, 60 million for one. But it basically rolled up into the same math. 40, 50, 60 per partner. You'd invest very early at valuations between 3 and 10 million pre, depending on who they were. And you can get enough ownership for 2% of your fund. Right. To have diversity. So 2% of a $50 million fund is a million. So how many deals can I get? 10, 15, 20% of a million. Right. That model probably doesn't work anymore. Right. To do that type of, you say, why is everyone raising a 3 to $400 million seed fund? Well, it's the 2% model. It's not just a game. It's okay. I need, I want to write 2% checks that are 2% of my fund or less. Right. So even as seed has become pre seed and that's okay, all the names changed, Right. You know, Series A became seed. It's all cool. But does the traditional 50, 60 million dollar seed fund work? I don't, I think it doesn't work unless you go with anything that has any, any proof, any social proof, anything privileged, it doesn't work. Right. So you either have to find the less privileged where I think it works, or you have to settle for a very different model. Right. A lot of these founder led funds are okay with de minimis ownership or very high valuations. They think it'll all work out in the end because they have decacorns. Right. And that, and that's disrupting seed too, because if you need to own 10% in your seed fund and a founder led fund is okay with 3% or 2% because they're doing 30 deals a year and they know they're going to have four decacorns per fund, that completely breaks the traditional seed fund model too. Right. So I think it's the only part that hasn't adapted. We see these Greylocks and Andreessen's and Others and Sequoia sort of adapting, but I don't know, I don't know. I don't know that this model exists, at least in the same way as when I started investing. I don't know that it exists.
You said there are problems with precede or it goes bad. What did you mean by that?
When it goes bad? Is that what I, what did I say?
You said about the problems of precede and we'll get into that.
The problems with precede. Oh no, I think all I meant was that I think the media confuses the privileged precede with the less privileged. I don't think we've seen the same levels of inflation for folks that have no social proof, have no background. I don't think so.
How do you advise founders when they have big multi stage funds putting big term sheets on the table at the seed round?
I think that here's a point, I'll give you the advice and I'll tell you a point that's changed over the last two to three years. First of all, you don't have to spend it. Just always remember you don't have to spend it. Right? I think. But let me go to the point. It used to be just a few years ago there were a couple of problems with big huge funds doing seed, right? One was of course signaling. Oh my God, Excel, Sequoia, whoever did the seed, but they didn't do the A. Let's be clear, that was a signaling problem. The big funds would say it wasn't. It was a huge signaling problem. It was a seven on a scale of one to ten. And the only people that said it wasn't was the people running these programs. It's a huge signaling problem. Of course, if Sequoia or Excel or Andreessen or LightSpeed has two years of data and they don't preempt the A, of course it's a problem. Of course it's a bad signal. So that was a problem and that exists today. One weird thing though, today is the big fault. If you take money from a big fund as an early stage founder, there's actually less pressure. There's less pressure. This is so changed. The funds are so big and they're raising funds every 12 months, right? We have different portfolios. In my portfolios when the, when the multi billion dollar funds have come in and led the A or the seed, they're barely invested. And you know what? They don't even care if you have board meetings. They don't even. And here's the thing, Harry, they Don't care if you lose all the money because it's just 20 million bucks. They don't have time. They've done 40 investments, they're on 20 boards, and just the 20 million is the entry position. And listen, they might be a little upset if you, if you don't get to a billion in 24 months, but they don't care anymore. That used to be a career limiting move. You used to lose your job if that $20 million check didn't perform. Now nobody cares. They don't care if you've got 2.
Billion and you're doing the 20 million. I mean, it's 1%.
1% and it's 2 billion in a year, Harry. Instead of four to five years, it's in a year. You don't even have time because deploying a fund in a year requires a level of velocity that we've never seen before. You can't care. And the good news is, if you woke up this morning and another one of your portfolio got marked up to a unicorn at a thousand X or whatever, that's fine. That's the way the game is. And if they're going to lose money on the other one or if it's just slow, nobody, they don't care. And if you're an empathetic founder like I was, and it may not, may not all be a positive, it takes a lot of pressure off you as a founder. If your investors don't care. I worried about it too much. Right. They literally, they literally don't care.
No, I'm totally with you. I think it's about finding the right balance. You never want founders to be desperately depressed or kind of mentally unstable. But I'm totally with you.
I just think this is if you're the right type of founder, the fact that there is less investor pressure for large checks can de. Stress your life. If you play it the right way. If you play it the right way. Right. The pressure even to raise it a couple hundred million in valuation years ago was so high today they may just leave you alone. If you're the right founder. That's a gift.
Listen, I agree you said about deployment pace there, you're very disciplined. And actually you haven't really changed your dependent deployment pace.
Yeah.
Like others have done to nine months or 12 months. Like how do you think about deployment pace and discipline on. On check writing? Blondie, I.
So look, everyone's different, right? First of all, I've learned. Do you do any. What has changed? I think I've learned over time is the burden of being the lead investor over time has gone up as everyone does less work. Right. The number two, the number three, the number four investor does less work. The amount of work the lead investor has gone up. And I was just looking at my portfolio the other day. I added a column, where am I the number one investor? Because that's where the time is. People used to do it. How many board seats am I on? Which was the amount of work? You know what, Harry? Now that we do it over Zoom, a board meeting is not like the end of the world, is it? It's really not a big deal. Right? But be number one. And so I think how many active investments can you be number one in? And it might be five. Like the traditional. The old school metric for board seats was it was supposed to be 10. Okay. But when you started to run the place, it would be 20. Okay. If you go back and talk, when you do the 20 VC, you talk. They would be on the Arthur Rocks, Whatever. They'd probably be on 20 boards. Okay. I bet Byron Beater is my favorite. I Bet he's on 20 boards. Okay. But that would be this capacity for going to boards. Right. But being the only active investor, it might be five if you take it seriously. So you have to wait if you want to be a seed investor and have high ownership. That's the compounding effect. Right. And I haven't found, at least with my. What I'm asked to do by founders, what I'm asked to do, which is help build the teams, I haven't found I could do more than a few of those at the same time.
Yeah, no, I agree.
That's the problem. And I don't think that's a wise way to invest. The better way is to not help at all. The truth is, most top VCs will tell you that historically, historically, that they don't. The best. The best startups don't need any help. Right? And they'll say that meme again and again. And if you think through it, that really means you should do the least you can other than win the deal. You should win the deal and exit any time commitment.
This is why I'm funny. I'm so bullish on my model, which is. I am very light touch. You need an intro to the CTO at Zoom.
Done.
The head of sales at Slack. Done.
You need to marry. But.
But that's super. Is so lightweight. Jason, meet Tom. Sarah, meet Rachel.
Yes. Well, as you have more money, Harry, and as you become, in some cases the only investor in A company, right. You've already raised 180 million in your last two funds, right? Let's imagine you raised 360 in the next one. You may end up being the only investor in a number of your investments, right? Or the only significant investment, right? Because as these cap tables are getting sliced finer and finer, you could have one person owning 20, right? Probably my single best investment today. I own a little more than 20 and I don't think then I have one that owns eight and then everyone else owns a tiny bit. So I'm. And I love this company, but I'm on the hook forever, aren't I? And so it's great to just make those. And listen, you have such an incredible network. If you can just make connections. That's worth it to have Harry on my cap table. Like anyone listening to this, put Harry on your cap table. But if we're doing insider baseball, as you will be able to sustain that as you have more ones and ones and ones as an investor. And those ones get so big that two is just doing emails.
I'm totally with you. I think it's a really fantastic. I don't know, I think honestly it lands to the type of deal that I do and I rarely do. The ones where you're solely the one with the majority. Now, I'm not saying at all that won't happen. Where it does happen, which I have now, Blondie, I am on the hook and I work fucking hard.
You do. And then as time goes on and you start to see distributions and other things happen, you start to see the benefits of even being the largest investment in one winner. Like being the largest investor and one winner can out. Unless you can just nail that 2% of datadog strategy. You know, this is Honam's point, right? Which is being the largest investor in a generational company, that's enough. In venture, right? And the world is different today. You can run a different. And you're running a different playbook, but that one does. As time goes on and you're. And you're. You get busier and busier. The slugging it out and trying to be the largest investor in a Decacorn becomes more and more appealing. Yeah, right.
I get you. It does.
I mean, the investment I made in Talk Desk, it's Storm Storms. Storm was the largest investor. They're still close. You know, if it's worth 20 or 30 billion, that will be the best investment in 25 years for that fund, right? That, that more than outweighs all the other stuff. So if you just think about slugging like, and, and, and as time goes on and you get busier and 20 VCs doing 300 million a year and you're managing 4 billion under capital, there is a temptation to, to slug it out and want to have that number one position on the cap table, isn't there?
Man, I'm sorry. That storm portfolio you built is just a rock.
Yeah, but I just. But you learn from it, right? And you learn. So. Yeah, but I. Listen, if you can maintain what you're doing at 20 BC, it's epic because it's the next everyone. There's a lot of folks who have kind of done the next generation thing of what soccer did in the early days. Right. Soccer just had such a large social following. He could move the needle. Right. And that alone doesn't work today. That almost seems like most things. It seems so basic today. But if you can continue to make connections through your network, you're more valuable than 95% of the investors on the.
Cap table, for sure. And off record, I'll tell you why I think we're so much better than that, which is exciting. I do want to ask. You mentioned board seats and board meetings. I've sat on them, Jason. I thought they were pretty useless and ineffective, to be quite honest. Do you actually find board meetings help?
I have changed my mind. So when I started investing, I felt there was nothing more torturous than going to a board meeting. Okay. I remember my first investment was Pipedrive. Vista bought them for 1.5 billion, and I had to be tortured to go to those board meetings. I'm like, I'm like, I got you your VP of sales, your cfo, all your other, like, I got to do this again. I thought I sold my company so I didn't have to go to board meetings anymore. I thought I was supposed to get a break from this crap when you have an exit. And I really thought they were terrible. And none of the first investments that I do did I appreciate them at all. Right. None of them. I viewed them. But time goes on, and I've learned a couple of things. First of all, as I transitioned to having more and more number one investor positions on the cap table, I realized that fiduciary, there's a fiduciary obligation in the lead investor, and it's very serious. In this day and age of therados and thousand X deals. Who's responsible for the diligence? Who's responsible? Oh, you raised 20 million in your seed. Great. But who's responsible for that money that it's used properly. And I don't mean going through the books or anything like that, but who is providing every six weeks a check and balance. And that check and balance is that you show up and you report against revenue, you report against cash and you report against sales and marketing. Right. I actually view this in this age of more and more investors with smaller positions who care less. This fiduciary responsibility when I'm number one is weighty. It's weighty, right? And the ones where I'm number two or number three, I'm like woohoo, I don't have to do this. So there's fiduciary two. And boy, for founders this is so important until you're big. Until you at 40, 50 million when board meetings really are about money around the table. Right? Until that phase, board meetings are at least 50% for your management team to present. There is nothing few things more valuable to a CEO than having an external forcing function for your VPs to have to hit their numbers. You can only how often a CEO can you yell at your team? I would argue once a year. Now there are CEOs that yell. There are yellers out there. But I would argue you can really only yell at one of your VPs. And I put yell in quotes, whatever this means. I think you can really only be so upset with them once or twice a year. Otherwise it's demoralizing and people quit. Right? But if every six weeks your VP of sales that's a little bit behind has to report Harry, I'm My plan for Q1 was 10 million. I'm at 8.4. Here's how that forcing function for you not to have to do it yourself as CEO. And each functionality, sales, marketing, product engineering is it's like a nine on the value scale. And that's also as an aside, that's why I beg founders not to use notion at and board meetings. I beg them to force everyone to make slides to spend the time. Because we all love notion and Coda. We just put our stuff in our Google Docs and it's so, it's so efficient, isn't it? But, but and not only did I think board meetings were stupid when I started investing, you know what I thought was even stupider? Founders using slides. I'm like oh my God, like what People are still standing up in rooms and clicking through like I can't believe people are still doing like I get what you do. Like I don't need to see your stupid presentation. But Then I, then I realized as time goes on, the work you force your management team to put into those slides for each board meeting forces organization, self discipline, reporting, goal analytics that otherwise they just don't bother to do in notion. They don't do it. They just write a stream of consciousness or an update to a table. It's not the same if you don't put the work in. You don't get, you don't get the value out. Do.
No you don't, you don't. I find the best managers so do delegated responsibility where they kind of say, as you said, they bring their functional leads in each area and then they delegate to them. Because one thing that does worry me is when you see the founder and CEO at this scale up company just spending way too much time doing the decks themselves and you're like, you do need to find some form of delegation that works here. Do you know what I mean?
For sure, for sure. But I think as we, as we've gone into the era where you can use safes up to 200 million and other things that the presentations the board meetings have atrophied and I think it's a, I think even if the CEO doesn't get it for their investors, even if they don't really respect any value add from the investors, the. Your VPs take these board meetings very seriously. Here's the, here's the other fight. You may not as the founder, but your VP's. I got to present to the board. Oh my God. Every VP I've ever worked with gets nervous. That is a gift to you as a founder. Harness that. Harness the fact that they may be comfortable with you as a founder, but they're nervous about presenting to Harry or Jason. It's just Harry or Jason. Give me a break. Why should you be nervous presenting to us? But the fact that they are is an amazing management tool for CEO.
Yeah, no, I.
Right.
I'd be terrified presenting to you, Jason.
Yeah, and that's a gift as a founder because you don't have to yell.
Yeah, no, I agree.
I think where does the board member really have to yell? They just have to be like that's enough.
We miss plan.
Okay, nice. Any questions from the board on this one? No.
All my personal preference is when you get the. And then the next board meeting, the associate comes and you're like oh, they've done.
That's a different issue. Yeah.
Oh, that, that pisses me off. I don't like that. Anyway, that's a different issue. But I do want to move into a quick fire, Jason, because we could chat all day. So I say a short statement. You give me your immediate thoughts. Okay.
Okay.
So what sales tactics have not changed over the last five years?
What have not changed? I think that. I think what has changed the most has also not changed, which is Outbound. Outbound still works even when We've all deployed 150 SaaS, apps evaluated 1000 even when we're overloaded in the cloud. Great. Outbound works great. We do not all have time to do discovery on our own. So you're running a business, Harry. What's your number one problem that you have today? In 20 overall, what's the number one.
Problem you have concentration of responsibility around me, lack of delegation.
Okay. What if I had a tool that auto delegated everything at 20 VC and you didn't have to put any work into it and it handled it with AI? Would you take a quick call?
Yeah. Okay.
There you go. That's called outbound.
Okay, sure.
That's. I just did outbound to you right now. I was lucky enough to get you on.
On, On.
On the riverside. But. So that has worked. Has sending that email to 10,000 people through Salesoft or Outreach or Mixmax. Does that still work?
Like.
And I love all those tools. Right. I've invested in two out of three of them. It works, but its efficacy has declined. Right. That, that. So my point is that one of the things that's changed most is this outbound playbook we perfected five years ago that we're all running has declined in efficacy. But Outbound itself works better than ever. And I'm just shocked with all the applications out there and all the competitors that great Outbound works better than ever. But mediocre Outbound is still works, but is declining in its efficacy.
What sales tactics have died to death. Which do we just not see anymore?
I think the playbook keeps getting better and better with rev ops becoming a function and all these other things becoming a function. I just think that, you know, the. I'm not sure any of it does. The only thing that has really changed, that has changed the most is just when in the funnel we're doing face to face and when in the funnel we're making those connections. And I think the biggest change in venture and enterprise sales, because they're similar, venture and enterprise sales actually have some similarities to them is that those first meetings are no longer done in person. And that has changed venture radically. And it has also changed enterprise sales. Right. Covid changed it in that we are like, I don't know what you see in your portfolio, but all of the enterprise SaaS companies I've invested in work with, they're all going back to face to face meetings. Nick met on gainsights talking about it. They're all going back, but no sales reps are doing it for the first meeting anymore. Right. We've learned what works from home and what doesn't over the last 20 months and we've learned we want to get together, but we want to do it at the best possible time. So we want to do it in the middle of the sales funnel. Right. And we want to. And where do we want to do in customer success? I'm actually not sure I know the answer, but it's probably less in the kickoff meeting than the 90 day plan. The plus 90 day meeting. Right. That's when you want to fly out. And we've gotten better at when to use that in person time, but. But we're still doing it.
Do you enjoy Investing by Zoom I have Brian Singh on the show from Founders Fund. He said no, it's hate it and I'm not doing it anymore. So I hate it.
I hate it. But I didn't know why until a couple of weeks ago. It's not because of the risk. And there is, it is increased risk. We've increased risk in venture, but the returns have gone up commensurate with the risk. Right? It is for me. And it's not because I'm so amazing at sussing out a founder when I meet them in person. Like I have such a human superpower. I mean, we all think we're better at that than we do. Right? Including all CEOs think they're amazing at it. It's more because the cadence was perfect for me. I would get an email and it would explain the business. Right. We could meet in a week in person. I could ruminate on it. I could see if what I hoped was true was true in person. I could see if I trusted them and loved them and fell in love with them. And then I could decide about 20 minutes into that meeting if I wanted to invest. So I made all my investments decisions Pre Covid in 20. It's seemingly in 20 minutes. Like you could, you could ask all my initial investments. I would interrupt the first in person about 20 minutes. And I would always say the same thing. If everything you've told me, Harry, is true, I'm in. And I would mean it. Like I would always say that. But I got a chance to do the work Ahead of time, I got a chance to not be under intense pressure to make an instant decision. And I got a chance to spend that week or so ruminating and then using that in person meeting to solidify that conclusion. Right now I've got to make do that in the first zoom and I can get a, you can get a second or third follow up. Right. But it's become so transactional that I feel like I'm not as emotionally engaged and I, and I, and I just, I fade away a bit on that, on that trend, the transactional element of it. So. But maybe I'm just been doing this too long, but I feel like I get, I kind of get a D for investing over zoom. Even though I seemingly used to invest in 20 minutes, there was this secret process where I had 10 days to ruminate and learn that just changed everything and I don't like it.
And the compression of fundraising timelines has been so immense, you now have to decide within 24 hours.
Sometimes, you know that I think of all the things is less different than it used to be, I think because even back when I started investing, 2013, 2014, if a startup was hot, at least by the time I met them, because I'm different, they already had a term sheet. So I never had, I always had to make. I felt like I always, even though I did that 20 million, 20 minute thing, I always felt like I kind of had to anyway because they already had. Now maybe today it's going to close this afternoon. Like that's different than a couple years back. But they already had an offer. So you always, I think you always, I mean, even in my very first startup years ago, I got term sheets the same day. Like that is nothing new. There's nothing new. When that startup just stands out and they just grab the part. They used to grab the partners down the hall, right on Sandhill, and they throw them in the room. They're like, Harry, just, just, actually before you go, can I just have you meet this bunch of white men that work at my firm? Rob, Bill, Biff, Bobby, the other Bobby and James and James and James, while you're here, do you have to just run through the deck again? And then you'd be having dinner that night in downtown Palo Alto and get a term sheet, right? So it is compression. I actually think the compression, what I've seen, I think it's harder on the late stage investors who no longer can do diligence. I had, I had an investment recently that did, did a. Now it wasn't a Thousand xr but did a very, very, it was a relatively hot round and one of the best VCs I've ever worked with called me is like we don't have time to do any, can you just do all the diligence for us? I told them all the VPs, all the issues and I think it was very helpful. They literally, and this is a relatively conservative firm, they just, there's just no time. Right. The advantage to seed is the diligence universe is a little bit more confined. So I think it's somewhat easier to do it on that compressed time saying.
But I'm totally with you. I see a lot actually of kind of growth firms kind of doing the theses deep dives and then making them more personalized for companies and then going active outbound and saying hey revenue cap, we've done all of this work in the space, we've spent hours doing it, we market and that's how they kind of approach deal winning.
So I think those things have just got everyone people coming. It's just gotten faster as it should on the Internet. Right, but, but the fact that the whole process is transactional is new, right? That it's entirely, entirely transactional. And then I see these founder led funds literally making decisions in five minutes with relatively large pools of capital for seed funds. That one is like the ultimate disruption. Like I was just on the phone with some CEO, some unicorn CEO. She started in 250k into the round in five minutes. Right? That's great for the founder but as a traditional investor it's hard to compete with that, isn't it? I see this all the time and you do 10 calls with founders, all of whom have their own fund or maybe have a very large scout fund or whatever and they've put in 3 to 4 million in a day. They make, they don't do any. Founders don't do any diligence. Right. They just, they just, it's like they just decide if they're great. Right. And so that's the, that I think is the, is the, that's the ultimate end version of this, this hyper, hyper version.
We're not going to talk about founders raising external money for funds that just, it does not bode well.
So if you, if you, if you'd even talked to me eight months ago, I would have agreed. Now like doc send and, and other things you got to give up. It's the trains left the station. There's too many founders that are going to raise nine figure funds while they're running their Own startups. And it used to be a bad sign for the startup, right? And all it used to be like, how could you do anything other than run your own startup? But it doesn't matter what you. And I think because there's gonna be 50 of those funds, there's gonna be 59 figure funds.
I don't get the trade off in terms of time though. You know, I see quite a lot of my friends who run amazing companies and they have five $10 million funds and I'm like, if you increase the enterprise value of your company by 1 or 2%, you'll make far more than you will from this $5 million $10 million fund. Just focus. Angel invest, Take some secondary angel invest, fine. But if people give you money, you are committing to them and you have an obligation to them. To go and raise money for a separate fund is just. I don't.
I think they think they're going to more and more than will raise 100 though, Harry. And they think they'll do 4 to 5x funds. And so if they and their partner can split up extra hundred million dollars in carry while they're running their company and say take 20 or 30 million of secondary out of their own series B round, they feel like that's a world they like to live in. Like I can get 20 million in cash for my secondary. I can run my company to a Decacorn and I can make another hundred million from my founder fund. I think that's appealing. That's not a tiny little seed fund. That's people are going to give me 100 million and because I'm at a center of some hub, I can deploy this hundred million dollars effectively. Right? Likely with limited pro rata and other issues. So my absolute return if I do enough of these deals could be good. Right? Most of these funds like this, they have one great Decacorn in their portfolio and it just worked. It just worked. Right? So yeah, you're like, God, I would never invest in a founder that has their own fund. 2022, you may be doing this every week.
That's hilarious. Tell me my friend, final one. What's the most recent publicly announced investment and why did you say yes and get so excited?
What's the most recently public? The recent one was from a little while ago. Boy, it was. And you have to keep challenging your play. Maybe the most recent public one is a company called owner.com, which is to over simplify, maybe as a next generation toast. And it's in a space that's very Competitive, right? Has margin issues, lots of challenges, hard to understand the competitive landscape quickly. So those things seem to break a lot of the traditional rules, right? But one of the things that I've realized, there's a couple reasons. The investment was interesting, but one of the things I've realized is I've just fallen in love with the incredible CEO CTO pair. I don't mean both good, I mean incredible. And when you have an incredible CEO that can see the future and a CTO that can ship software five times faster than a pretty good cto, their ability to iterate is so jaw dropping, right? And when I see that co CTO combination, I honestly, when they're both A pluses, right, it's hard enough to get one. Everyone thinks everyone's. But when I see both as an A plus and any traction at all, like any traction at all, I feel like I literally cannot lose money on that combination. And as an ex founder myself, I feel like a lot of investors are now right. It's no longer unique, but I feel like I have the ability to know when both are great that some people can't. And when they are, I'm like, God, even if they screw it all up this quarter, the software they'll have next quarter. I just got an email from owner and like they added this whole new marketing automation level, right? And its first month that added 200,000 in revenue. It's first month. I'm like, who does that, right? I mean the level of agility, right? And we see hints of this in stripe, right? At others, at scale. But, but that's my, that's my rambly answer to what I'm obsessed with. And when I look back at startups I've done where, you know, the CEO is pretty good, but the CTOs turned over a couple times or there's just not that, that, that Batman and Robin pairing. You can do it. But I'm done with those ones, I think.
Listen, Jason, this has been so much fun. I love our chats, always. I can't believe it's taken us so long to do this again. But honestly, thank you for doing it and I really appreciate it, my friend.
Thank you, Harry.










