What I learnt from 200+ angel investments and why contentment as a founder is key with Adam Spector

Like in the end, what you should be focused on as a founder is what is going to get to a delightful outcome for my customers? Maybe that's AI, but it's probably not. It's actually more like, how do I just build a fantastic product that will make my customers extremely happy? It might have some AI elements, it might have a bunch of other things. It's probably a bunch of different technology pieces altogether, but certainly that's a big trend. The danger, though, is 5 years ago, 6 years ago, it was blockchain.

Adam, thank you so much for joining me. Thank you for making the time.

Absolutely my pleasure. It's always fun to do this stuff.

Yeah, no, I love it. I was trying to think, last time we were properly catching up, we were sat outside at a lovely restaurant in SF talking about various different things with loads of founders, which was great fun. So, yeah, it's always good to bounce ideas around with you. And look, you're a 4-time founder, right? And also angel invested in over— you corrected me earlier. I said 50, and then you came back and said 200, which I was like, dude, that's big.

It's a lot. I don't know if that's good or bad. Obviously, my general thesis, by the way, for a lot of these things in any investing is actually having a larger base of investments. It certainly reduces the really high outsized potential on the upside. Right. You're not going to hit the likelihood of having that million-to-one hit is rare. But the overall returns, almost all the data shows the overall returns will be better by having a lot more bets. Yeah. So we have a lot more bets that are smaller, Yeah, but the data supports basically that's the way to go. Same thing, by the way, just go buy like an S&P 500 ETF is the right investment strategy instead of buying just like going big on one stock.

Yeah, 100%. Well, look, we're going to get into that and talk about angel investing and founders, but I actually want to go back to one of your earliest startups, right? Lift Ignite. And the reason I want to go back to that is we're recording this in 2024 where AI/ML is everything, right? Everyone is talking about it. Everyone wants to invest. Everyone wants to build in it. You guys were doing machine learning before it was cool, right? And you said earlier, you remember doing talks on AI and ML about 8 years ago. I wanna go back and I wanna say, okay, what were the conversations like when you were building Lyft Igniter? Did people understand the technology? Did they understand the use case? And equally, actually, from a build perspective, What kind of technical resources were out there?

Yeah. So, I mean, people were starting to understand it. So, I mean, the story we would tell people, which was very accurate and true, was like, my co-founder is one of the guys who built basically YouTube's machine learning personalization algorithm, which all of us listening to this today take that as a— they don't even think about it. It's not even something you consider. But you go onto your YouTube page, it's going to be completely different from mine. We just almost acknowledge and know that's the case. Back then, I mean, it didn't happen that way. It was essentially like what got uploaded the first time. It was just sort of a reverse chronological list of videos to some extent with some really basic stuff happening. And these brilliant researchers in machine learning, which was not sexy at the time, were like, hey, how do we use machine learning to identify patterns in milliseconds, right? The moment that page loads, but before it actually shows up in front of your face, how do I choose the right videos for Sam? First of the Rank videos for Adam. So people were starting to understand that idea and mentality, but it wasn't as obvious. And so what we were going to tell people is like, look, this technology is now viable enough that you can go put it on your e-commerce site or your media site. And that was still a really new idea for folks. So they got it, but not completely.

Yeah. Did they, and did they ask questions? Did they want to drill into it? Or like, did you find from a customer perspective actually They didn't really care how you did it. They just wanted the value that it created.

Much more the latter, which I think, by the way, is the same thing with AI today. And the danger with AI today is people say, oh, we're AI for X. I'm like, well, okay, X has been around for forever, and why is AI going to make this better? I don't really care. Are you going to get me more of what I want and what I need from your product? And I don't really care how that happens. I mean, same thing with The technology we're using to record this, or when I do a Zoom call, I'm not saying, oh man, I need to know the details of why Zoom is able to do a remote team meeting. I don't really care. I just want it to work. And if it breaks, I'm annoyed. And that's, I think, generally the right mindset for any product. No one wants to look under the hood. They just want to know it works.

Yeah. And when you joined LiftIgniter, when that kind of founding team came together, How was it all pieced together? Was it a combination of, okay, we've got some incredible technical talent and they needed someone who was commercial, or was it actually a case of there were other gaps and those gaps were what they were trying to fill?

Yeah, more the former. So the really early initial team was 2 really smart engineers. One was one of my co-founders, a PhD in machine learning from Princeton. Brilliant guy. He had brought on another technical co-founder who's also really smart, and then sort of a more junior but also really smart engineer too. And they're like, we don't have the experience or knowledge on how to go to market and maybe not the energy to do it, right? It can be very draining to get in front of customers all day long and sell and pitch them on why they should go use your product, especially if your entire life and career has been like focused on studying and Math Olympiads and getting a PhD in machine learning and then deep, deep research in something brand new at Google, and then to go talk to random non-technical people about why they should install your product on their own website.

Yeah.

It's a very draining thing to do. And so if you can find a good co-founder and partner who is into that and actually gets energy from it, which I did, That can be a really good fit. And that's where that all came together.

Yeah. And that's how it fits together. Okay, cool. Understood. And then just on the AI piece, something you said that's quite interesting was, okay, it feels like everyone's kind of bolting AI on and it's that kind of hot topic. Out of interest, of the kind of, what, 200-odd plus angel investments, how many of the companies that you've invested in are now incorporating AI in some form? And if I can ask you quite directly, how many of them do you think AI is actually needed?

Good question. So I think for AI being needed, it's maybe under 10%, well under 10%, maybe 5%. I bet 10% are trying to be AI-type companies and have AI employed in some way. And who knows, maybe another 5% of that are saying, like, we're AI for X, even though they're not really AI, just because it's sort of a sexy thing to do. But still, that leaves you know, a huge percentage of the companies that we invest in that aren't AI, that aren't trying to claim to be AI, that don't care about it. Now, with that said, I think everyone, every smart company should be considering how can AI have an impact on my business. Yeah. I, you, you should be thinking, how can I use this new technology to advance what I'm building?

Mm-hmm.

But it maybe it's not the core piece of who you are and what you do. I mean, same for my own company, Levy.

Mm-hmm.

We're always thinking about How AI. do we use AI? But I'm also thinking, how do I use all the new technology out there? It's not just AI. I should be thinking every day, what are the new things that will give me an edge and make my business better? And if it makes my business better, it should make for better deliverable and more delightful experience for my customers. And that's just good business. I don't care if it's with AI today or 10 years ago with mobile or you name it. You should always be thinking, what's the new tech and how do I use it?

Yeah. How do we leverage that? How do we scale? It's super interesting. And I mean, again, it's kind of staying on that track. I mean, one of the things when doing my research and knowing you and knowing your background, you've been around B2B SaaS and whether that be as a founder or as an operator for a number of years, what are the biggest trends that have kind of come and gone? And what are the biggest trends right now that you think actually founders are spending too much time, allocating too much time, too much resource to?

Yeah, I mean, certainly, obviously, the biggest sort of obvious one you were just talking about, right, is AI. I mean, people are spending a lot of time, how do I use AI? What do I do? How does this give me this big edge? And I think people probably are overspending time considering that. Like, in the end, what you should be focused on as a founder is what is going to get to a delightful outcome for my customers?

Yeah.

Maybe that's AI, but it's probably not. It's actually more like, how do I just build a fantastic product? That will make my customers extremely happy. It might have some AI elements, it might have a bunch of other things. It's probably a bunch of different technology pieces altogether, but certainly that's a big trend. The danger, though, is sort of like 5 years ago, 6 years ago, it was blockchain. Everything was blockchain, right? Today it's my CRM, my AI CRM. 5 years ago it was my blockchain CRM. Yeah. Have any of those overtaken or overthrown Salesforce? No, because there wasn't actually a real underlying value to my tech on the blockchain or my tech on AI. And so I think people are jumping on the bandwagon. I do think there's really, as with everybody, AI is going to provide value and it's going to dramatically change a lot of our lives.

Yeah.

It hasn't quite happened yet. You know, you and I probably both use AI maybe every day for like a few questions here and there.

Yeah.

But it's not directly impacting every single thing I do.

Yeah, not yet.

It will soon.

Yeah, I agree. I think it's been interesting watching the products that you touch and use on a daily basis try and roll out AI. And some of them have done it well. Some of them have done it actually, I think, pretty poorly. And it's interesting to me, I think, and I don't know if you find this as well from like an investor founder perspective, but it's always interesting to see who's close to their customer and who's not. And you get this sense that, okay, features have been deployed, actually they haven't really been tested. And then the value that ultimately a user has is just either not known or it's just totally skewed.

Yeah, I know. And that happened too many times. It's a sexy thing. So you might have a CEO who's like, to get my next fundraising round, we have to say we're an AI company. So they push out some feature that says, okay, now we have AI. Luckily, I think a lot of VCs are kind of getting over that and like, well, what is really the value of AI you're doing here? Why is that providing value? But people will rush that out because they need to hit their next big fundraising milestone and forget about the product milestone.

Yeah, for sure. And I mean, again, kind of going back to Lifting Nitro, like, when you were selling, you said that, okay, people didn't really care about the technology, they cared more about the value. Did you still find it hard though to get them on board when they were like, okay, we've never seen anything like this before? Or was it actually, it was just such a simple, simple use case, simple value driver that, you know, fundamentally that was all they focused on?

No, it was actually really difficult for us. And it was one of the big lessons we learned, which is the ability of a company to measure the value they provide is incredibly— is like critical to the success of that company.

Yeah.

So what I mean by that is for LiftIgniter, we were providing very clear and I think fairly measurable uptick in conversions, time on site, all these things. The problem is there's a lot of things that happen on a website.

Yeah,

a lot of people have their hands in the pot to make it better. So it wasn't always clear, was it us driving it or was it that other change that some other stakeholder has because they, they changed the wording? It's like, no, no, I did this great wording change and branding change. And that's why there's more time on site. That became a real debate and really difficult to prove.

Yeah.

And so we kind of weren't in control of the end value that we had, which made it very difficult for customers to say, yeah, I'm clearly going to sign up for this and pay you for that uplift. Yeah. And that was the real big issue. And what's kind of a key lesson I've learned for, for delivering any product, you need to know, did this product actually deliver? That value, use it and get here. If the answer is yes, you will, and you'll keep using it. If the answer is no, you might not be willing to pay for it.

Yeah, for sure. And how can founders, I mean, how can founders ensure that that is actually what they're doing and they're going along the right course? It's kind of the same as validating a problem, right? And asking the right questions. It could be very easy for bias to come in. It could be very easy for emotion to come in as well. But yeah, How do you ensure that actually you are measuring the right value and that you're not attributing that to something else? Because that can fundamentally kill a company.

Totally. You need to take huge control of the narrative. You essentially have to control your narrative. A big part of that, it doesn't always work, but you need to control it more. So, as an example for what we do at Levy, so we're back office services for startups, right? So, we run HR, compliance, equity, and a bit of finance as well. Essentially, you're outsourced chief of staff. The thing is, like, we know we save a ton of time for our clients.

I

mean, very clearly. The problem we have is a lot of startup founders don't actually know how much time they're spending because they're like, 5 minutes here, 10 minutes over here. They do it late at night. They're not tracking their time.

Yeah.

And so it just disappears. They don't recognize it. So our challenge is we need to send them at least every month, and we try to do it more often, a detailed spreadsheet, like basically dashboard.

Interesting. Of

all the work we've done for them, all the tasks, how much time it took, what we're saving them, the big projects to remind them that, hey, guess what? Like, so one example we do, I think it's over 200 now, 200 tasks per one per client per month on average.

Wow.

The average startup. And so our customers are anywhere from about 5 to about 75 FTEs.

Yeah.

You're talking 200+ tasks per month.

Yeah.

Founders never think about that. But imagine 200 tasks that you have to do as a founder.

Yeah.

Or you outsource it to us to do it.

Yeah.

Unless you think back office services is your reason for being a startup and the reason your VCs gave you money, you should hand that off.

Yeah.

But founders don't think about that. So we need to constantly remind them.

Yeah.

This is the value we're providing. And if you fire us, which you can, our contracts are month to month. If you fire us, you now have 200 more tasks on your plate. That you need to do. Do you want that? So that's the, for us, our challenge. But it's like, hey, how do we produce reports? This is the value we provided. This is our ongoing value. And if you leave us, you will lose all of that value.

Yeah. And have you found that there's, I'm thinking about this from a go-to-market perspective and acquisition perspective. Is there a moment like an inflection point where founders go, okay, this is getting really hard? Like, is it a certain task or certain number of employees? Or actually, when you're messaging to them, is it a case of, hey, look, let us just track the tasks and the amount of time that you're spending on stuff that's non-core, and then we'll come back to you with a report and this is what we can do for you?

I wish we could do the latter, but we can only do the latter if we're inside of the company and actually sort of doing that. We do have a worksheet we give founders a lot who are like, founders think, I'm not sure it's really going to provide the value I have, or I don't have that many tasks. Okay. Like, here's literally— I think we have how many on this list? I think there are like 60 or something, maybe more than that, but let's call it 60 or so, like big tasks we know you're going to have to do over the course of a year across a bunch of different categories.

Yeah.

And how much time those are going to take. So I'll give you like one example. So you have to do in the US, you do Delaware franchise tax filing once a year. Doing that right or getting that wrong can actually be very costly because literally if you get it wrong or enter the wrong information, You might end up paying 2 to 3 to 4 to 10x more in taxes to Delaware than you need to pay.

Yeah.

Even— but doing that task, getting it right, that's probably 6 hours total.

Yeah.

But if you break that down, 6 hours total is 30 minutes every month.

Yeah.

Over the year. So add those things up and now spread it out over the course of a year and suddenly it's like, oh, I have a huge number of tasks every month that need to get done.

Yeah.

You need to get it the right way. Or I'm in trouble. And so we try to give founders like, hey, here's your worksheet. Try doing it. If you don't believe me, here's lots of testimonials. But also do this worksheet, like track your own time. What are all the tasks you're doing at 11:00 PM on a Friday when you're like, I want to go to sleep and rest. I don't want to make sure payroll runs on Monday.

Yeah.

But it's still an uphill battle because in the end, people were in a little bit of a new category. And so that leads to its own set of challenges. Like, it's obvious to people. I'll give one last example and let us move on. I want to be all about Levy, but like, yeah, um, people know I shouldn't do my own legal work.

Yeah,

I shouldn't do my own bookkeeping and accounting. That's sort of been ingrained in the minds of founders. We're this new category. It's like you shouldn't be doing any of the back office work yourself. That is a crazy idea to me because you're just going to literally reinvent the wheel, which by definition is idiotic.

Yeah.

So why would you do that? Especially when time is the most precious resource all of us have. And the decision about where to spend your time is the one thing you as a founder can control.

Yeah.

And if you make the wrong decision about where to spend that time, your startup will fail.

Yeah.

You might feel like you're making progress because you managed to run payroll. Who gives a— who cares? I'm trying to be careful with my language. Like, who cares?

Yeah.

Yeah, your team needs to get paid. It needs to get done. But is it better to spend an hour making sure that gets done right and learning about how Gusto or Rippling works? Or is it better to spend that hour making sure your website is so freaking on point that you're going to close that next customer?

Yeah.

What do your VCs care about? You're a VC. What do you care about? Do you ever ask your founders in your board meetings? So tell me all about how great your back office is.

Yeah.

No, no, no. Tell me your growth. Tell me your product updates, team updates. That's what you care about.

Yeah, we come back to that focus point, and I think that was something that's really interesting again. And I'm linking this to the angel investments that you've made and the founders that you've backed. And I know I asked you recently, what are the kind of key traits or key founder characteristics? And one of those things is focus. And I want to drill into that actually, because I think if you're a first-time founder and you've not been through this process before, it could be overwhelming. It's probably overwhelming even to experienced founders, right? How do you stack rank? How do you prioritize your focus and how do you break down the tasks? Clearly, using something like Levy to outsource that is super important. But again, if you're starting out, how do you stack rank these tasks?

So, I mean, I'll use a quote from someone much smarter and more successful than me, but Naval Ravikant. So he said very publicly that he basically only does I'm going to butcher this quote, but basically only does work if he views it as being worth $2,000 an hour. That's the value that he puts on his time. And he makes it that high on purpose, right? He wants to make it really high to be like, should I really be spending time on this task? Yeah. I'm not quite as hardcore as he is, but that's also how I try to view things. And if it doesn't hit that threshold, I shouldn't be doing it.

Yeah.

And I should find a way to hand it off to my team.

Yeah.

And just say, I don't— I trust you, go do it. I don't want to think about it. Let me know when it's done and give me the update. And I try to do that all the time. So how can I delegate everything that is not the number one or number two priority for us right now or something that only I can do, right? So only I can be on this podcast talking about like what Levy's done, what I've done, and hopefully leading to more value to this whole startup ecosystem, which is just something I'm passionate about.

Yeah.

And who knows, at some point gets us more customers. That's something only I, as the founder of Levy, can do.

Yeah.

And so that's worth a lot of money in a sense, in my mind, and worth me spending this time with you,

Sam.

But beyond that, that's how I rank order things, is around that mindset. What are the most important things that need to get done every single day? And how can I either delegate the ones that are not as important or focus on the key ones that are and then move on to the next thing.

Yeah. And outside of focus, what are the next kind of the best performing traits that you see in the successful founders that you've backed and worked with?

Yeah, I mean, utter obsession. So the thing is that people forget, right? It seems sexy to be a founder. It's like, oh cool, I'm going to be CEO. Of my company in one. Really cool. Great. Congratulations. It seems cool, right? And it seems fun. And it is. And you can learn a huge amount being a startup founder. However, the successful ones share a common trait. And as you know, I have a podcast called Entrepreneurial Excellence. Spoken to, I think, close to 60 or so founders at this point. And the key takeaway from the most successful ones are always— they are obsessed with making that thing reality. Whatever they care about, they're obsessed with it. The reason you need to be obsessed with it is because it is freaking hard every day. You have to get up every morning

and

be like, despite all the setbacks that I had yesterday, I'm going to get up and be excited and energized for the new things that are going to come my way today. And there are going to be a ton of new challenges. And guess what? Also, I need to be ready to do this for 10+ years.

Yeah.

I bet all the people listening to this podcast right now, the number of them that have been doing anything for 10 years is vanishingly small. Maybe 1%, probably less than that have done anything for 10 years straight. The thing is, that's what it takes to be a successful founder.

Yeah.

Is you need to be up for being saying, I'm going to sign up for this for 10 years because the first few years, tons of challenges, tons of hard stuff, and very little to show for it in most cases.

Yeah.

It's going to take you a long time. And then by the time you get to year 5, year 6, and things start to really start to work, like, oh my God, like, yeah, we have real revenue, have a big team, then you have a million new challenges that have come up that have come up. You might feel like you're hitting it, you're striving to be like, oh my God, look, your company is doing great.

Yeah,

it just takes so much time. But the beauty, the reason why it takes so much time is one, that's just the hardship of founding a company, but it's also the power of compounding. So people forget, or frankly don't even know about sort of this, you know, as, um, uh, I think Warren Buffett and Charlie Munger used to talk about all the time, but the, the 6th wonder, 8th wonder, whatever, of the world, which is compounding.

Yeah.

Um, the reason that's so powerful is because— and actually, if you look at, I think, Warren Buffett's, um, his, uh, his personal wealth, right? Something like 2/3 of his entire personal wealth has been made in the last 20 years. Right. And he's what, 89 years old or something? Why did that happen? Because it's all compounded.

Yeah.

And the companies continue to do well, certainly.

Yeah.

But it's compounded year after year. He's doing the same thing. He's writing his annual report. He's making smart decisions, but he's taking his time.

And

it's the same thing for all of us in our careers and the businesses that we run. So this talk we're doing right now will help Levi, but it's one small bit that builds and builds and builds and builds. And it might take another 3 or 4 years because before I see a real payoff for this.

Yeah.

And then I got another probably 5 to 6 years before I see a real payoff and maybe never. But as long as I'm obsessed.

Yeah.

And I'm energized and I'm learning something new every day. For me personally, I don't care. That's what I get up for. That's what I live for.

Yeah. How do you, how do you become content with that and that founder journey? And how do you, I guess, fall in love with the process, which is something that's thrown around quite a lot. And I think when people say that, they don't really understand what that actually means, as you say, over the timescales that we're actually talking about. But the contentment piece I find super interesting.

Yeah. So, look, I feel really lucky in a sense that I actually feel very content with my life. And I think being content is arguably the highest order place you can get to in life. Now, I'm bragging on myself in a sense, but I feel like I've achieved almost all the things that I initially wanted to achieve. Now, there's still more. I'm still very hungry. I think I've not built the canonical startup that is worth billions of dollars, et cetera, et cetera. And that's really something I've wanted to do. I expect that I will. I'm probably delusional, but I expect that I will despite that fact. But I'm also really content with the fact that I have been a logical thinking, rational adult. Yeah. and made a lot of decisions in my life about where I want to be, what city I want to live in, who I want to marry and be with, what that person looks like. Do I want to have kids or not have kids? How do I want to just orchestrate the key pieces in my life and also recognize the trade-offs that I'm making? So being a startup founder means that, like, I'm a huge believer that you can only do 2 things really well in life.

Yeah.

At any given time. So for me, I made the decision that is Levy, my company, and my family.

Yeah.

That means I don't have a lot of extra time for friends. And I try to get— my workout is literally taking my kids to school. Like, that is my workout most days.

Yeah.

Um, and so you just have to make those trade-offs in life and be okay with it. But I've rationally thought about that, and that is a trade-off that I'm okay with. But, you know, I work 6.5 days a week and Every night when I put my kids to bed, I go back to work for another few hours.

Yeah,

there isn't a lot of time for anything else, and I'd have to give up plenty of things.

Yeah,

but that's okay. I'm content with that because it means every day I get to get up and I get paid by my own labor from our customers because we're a bootstrap company to do what I do.

Yeah.

That means I get to make— I get to run this company, work with really smart people, hire smart people. help other startups achieve their mission and vision. And I get— and most important for me, I get to learn new things every single day from really smart people. That's really cool. Like, that is such a joy and so lucky to be constantly curious and have the curiosity fed by what I do.

Do you think there's a different level of contentment and love for the process between bootstrap founders and VC-backed founders? And I ask this because I'm having more and more conversations now with founders who want to bootstrap. They want to go down that route. And I think it's kind of become sexy again, right? No one seems to care anymore about the big tech write-ups about huge rounds that are being done. Actually, the cool thing is to bootstrap and own your own business and sell it for $20 to $50 million rather than those billion-pound outcomes, right? But do you think that changes the level of contentment? Because you're going on a very different journey and you're making different sacrifices in both cases, right?

You are. I don't think it changes the level of contentment as long as you're making a rational decision to go down that path. So, if you're making that decision to go down that path, so for like Levy, we're bootstrapped, but I'm not going to say no to VC money someday if I want it. I mean, it's actually funny. Lots of VCs reach out to give us money right now, which is funny when I say no because of course it gets VCs more excited. But, But we would take money someday if I feel like it will help us achieve in a meaningful way, help us achieve our next goals. I'm not against it, but it's going to be a rational decision that I make, not because I need to do it, but because I want to do it and recognize the pros and cons of taking that cash and what it will do for my business and my team.

Yeah, 100%. And do you— is there a point at which, you know, and again, going back onto the angel investment, pieces. So the 200 companies, 200 founders that you've backed, is there a point in time where you see them become uncontent with what they're doing and kind of fall out of love with the process? And I'm intrigued, is that just through hardship? Is there a timing piece? Is that, you know, they hit a certain age and maybe their peer group are doing different things and they think, hold on a sec, actually this isn't very exciting anymore? Like, have you ever seen a founder fall out of

Oh, all the time. I mean, arguably I do on a regular basis, but you just, you wake up in the morning, you're like, do I still want to do this? Like, I'm a rational thinking adult. Is this something I want to keep doing? If the answer is yes, and I cannot think of any alternative that I would enjoy more, once I'm thinking on the long term, not just like tomorrow it'd be fun to go on a vacation, but like actually thinking, where would I want to be in 2, 3, 4, 5 years from now? And if the answer is still, I want to be CEO of Levy and making this into a world-changing company that impacts the value for every founder. As long as that interest is still yes for me, then it's still interesting. Even if some days I'm like, man, do I want to do this? Is this really fun? Because no, it's stressful. Yeah. And so I think, but there are lots of founders who don't feel that, right? They get to a point, they're like, this is just not fun anymore. And for them, I would say, yeah, great, move on, do something different, go somewhere different. I mean, I've been in San Francisco actually literally for 14 years. Yeah. Actually over 14 years now. Just recently, actually, coming up in 14 years, I think October. But in that timeframe, 2 really interesting things have happened for me. And this goes back to the compounding and just sticking with it. So one, 80% of the people who were in San Francisco with me at that time who came here to build cool tech stuff and be part of that team have left.

Right.

They've gone to do a ton of different things. That's fine. It's not your thing anymore. You're at a different point in life, whatever it is. On the other hand, because I've stuck around, I kind of grew up with some of the— and grew up and know lots of these sort of famous people who are really big in the tech space. Right. I've been to parties with XYZ person and shook hands with this person and know this person and one degree of separation from other people. Yeah. Like really well-known people out there. Because I've stuck with it and I'm still here and that compounds. So if I want to go raise money, yeah, like I have dozens of VCs that I can go call who are well-known brand names to go do that if that's actually a path I want to take.

Yeah.

I've also stuck with it every single day.

Yeah.

And been here and haven't jumped off that train. So they're just tradeoffs in life and both— there's nothing wrong with either one. It's just where do you want— where do you want to be? life and what do you want to build for yourself?

Yeah, intentionality is the word, I guess, that comes to my mind. And actually, on that point around compounding, do you think that that is the same for people who want to work in a startup? Maybe they're not going to make the leap into being a founder yet. They want to experience startup life. Maybe they're coming out of a large company. Is it the same thing? Is it about compounding the skill set, compounding the network, compounding the, you know, amount of resources you consume on anything startup related and building your niche and your kind of expertise within a specific area. Is that again how you've seen people jump?

Yeah, for sure. It's definitely a big part of it. And in fact, it's sort of what I would say is if you really want to compound from a career perspective, don't jump too often. Right. The key thing is what I'd rather see when I'm interviewing people is a clear progression in the company that you're with. From a promotion standpoint. If I instead see that you've jumped jobs every single year for the past 10 years, to me that says you're a striver, you're not going to stick around, you're not really interested in building something, or there's something else going on. And you hurt your own career by doing that on a regular basis. And sometimes I get it, like people want to make more money, they think you can make more money at some other company. Okay, sure, I get it. I did the same thing when I was younger. But to really be successful, especially if you're changing careers and going into the startup space,

the

thing that I really recommend people do, and I think part of why I've been successful in what I've gotten, like, why was I able to start my first company with 2 amazing engineers? Like, one of them was like one of the first early guys at Google. Yeah. Then my next company, once again, PhD machine learning at Princeton, who helped basically start the machine learning revolution at YouTube. Why was I able to do that? I don't have a technical background. It's, I think, partially because you have to be someone who shows up every day, someone who's reliable, someone who says, I'm going to go do this work. I will jump into doing it and raise my hand. I mean, what people don't get is they're like, oh, well, like, I didn't get opportunities at that company. I wasn't successful because I didn't get opportunities. I'm like, no one's going to hand you an opportunity.

Yeah.

You have to be in the game, right? Sort of use a sports analogy, right? You have to be in the game to score a goal. In general. So how do you get into the game? Well, you get into the game because you're good and you're better than other people, or you're not on the sidelines, you're not one of the backups. Yeah. So first of all, you have to be better and work harder and be reliable. And then 2, you gotta wait for your chance, right? So lots of— any sport, someone gets injured, hey, if you're the one who's been practicing the most, boom, you have your opportunity, and then you have to take advantage of it.

Yeah.

But if people bounce around too much, they won't ever be given that shot. And if they're not raising their hand. So I've always been someone who said, yeah, like, I'll do that, I'll do that. I don't care how much extra work it means. I'm not going to say pay me more because I'm taking on this work. No, I'm just going to go do it and do a great job. And what people forget is it is that willingness to raise your hand and then follow through on what you promised to do.

Yeah.

That is what leads to long-term success and to people trusting you to get things done. And then those opportunities will come your way. Just be patient, have a level of patience. But if you work hard, raise your hand, don't push, don't be annoying, don't be someone you wouldn't want to manage, right? Be someone who's great. Like, yeah, this person's great to manage. Those opportunities will show up at your doorstep.

Yeah, that's how they come out. And how, I mean, making the jump into being a founder, I mean, obviously, you know, you've done this 4 times now. I'm intrigued what What are the hacks? What are the loopholes, if there are any, into how you're building Levy now with the experience that you've got? Right. We've spoken about valuing time, focus. What else is there?

Yeah, I mean, I think the biggest one is, and it's taken my own time to learn this, is be willing to once again delegate and outsource everything that is not critical and core to what you're doing. Yeah. So many founders I meet in what we do at Levy, but really just in general, who are like, no, like, I was emailing with one last night about this and they've raised $20 million and the COO is still doing this work. He's like, yeah, like, we had a big issue with HR. You know, I understand what you guys do, but I feel like we needed to do this ourselves to really understand it. And I'm like, do you think Elon Musk or Jeff Bezos is staying up late at night to figure out an HR issue on their payroll system because, like, it's important for them to know about it? Or are they focused on how do I get the next satellite into space or whatever? Actually, I guess Bezos is also doing satellites in space. So for both of them, right? That's always what I want to know. What would these amazing entrepreneurs be doing with their time? And if it doesn't fit within that, then don't do it. So that's what I want to keep asking myself. And that's what probably my biggest lesson is, like, how do I keep delegating? making sure that I'm handing off the things that are non-critical as much as possible.

Yeah.

It's— that's, that's the biggest lesson. Too many early-stage, first-time founders want to own it all because they feel like it's their job to understand. No, it's not your job to understand. Your job is to ask the right questions. Learn how to ask great questions. Learn how to say, hey, are you really taking care of this and doing this the right way?

Yeah.

What are the outcomes that I should expect? Set really clear goals and outcomes. For anyone you delegate to, internal or external. Learn how to do that great. But you don't need to know the details and nuances of like the buttons to press in your HRIS. That is ridiculous.

Yeah. Yeah. No, I agree with that.

Arguably, despite all the money they've raised, and I love, I really like the founder, but like, they're probably going to fail. Like, honestly, to me as an investor, when I come across people like that and they're like, no, I feel like I need to understand this. I'm like, you're going to fail. You don't know how to focus properly if you think this is something that is good use of your time.

That's super interesting. And just taking that point, sorry, just sticking on that point again of focus. Any founder that's— and I've often found this, that some of the best founders didn't really want to be founders. They just had this focus, this obsession over trying to serve a customer, trying to solve a pain point, trying to make something good. and then they just kind of fell into it. Again, have you backed those kind of founders before? Have you kind of come across them?

Yeah, those are the best ones, in fact, that I like to back. So one example who I like to talk about a bunch and is a friend now, actually was a friend before he started his company, in fact. So this is a long time ago, but a company called BetterUp, right? They're executive coaching for everyone else. Alexei is the founder, and he was super obsessed with the idea of executive coaching for everyone. He wasn't an executive coach. He didn't have experience in that space directly. He was able to tell a good story about why that was important. I think he had some family history and some of that stuff and why that was important, but it wasn't his core skill set. But what he did have is he had this just obsessive drive and intelligence around the space.

Yeah.

That was sort of obvious when you talk with him, you sit down, you're like, oh my God, like, you care so deeply about making this real. You're going to work so hard to make it a reality.

Yeah.

And it's a good idea. Like, there's a clear market there. Like, of course, like, of course, if executive coaching is valuable for executives, it's valuable for non-executives too, if you can get the pricing right. So it seemed obvious in that sense too. It was worth backing. And by the way, like, I think we invested at a $5 million cap. And they're worth a few billion dollars today. And they had real trouble raising, real trouble, because Alexei didn't meet the general criteria, didn't have all the normal things. But to me, he was just utterly obsessed.

Yeah. Super interesting. Adam, thank you so much for getting into all of these topics. I think we've covered a huge amount there, so I really appreciate it. If there are any founders who want to reach out, they want to learn more about Levi, they want to know more about your angel investing, they want to know just to chat to you generally about how to think about being a founder, how can they reach out to you?

Yeah, absolutely. I'm easy to find on Twitter. I refuse to call it X since I used to work there. But @hspec00 there. I'm very active on LinkedIn, so reach out to me there. Let me know you heard me on the podcast and then happy to at least try to find a little bit of time to chat. One of my passions, I said, is trying to give back. I think the world's a better place when there are more entrepreneurs. in more entrepreneurs who are successful. So hopefully use Levy to help you be more successful. But I think the world's a better place because of that. So find me, those are the 2 best places. Or of course, just learn more at levy.company.

Amazing. Awesome. Adam, thank you so much for your time.

Yeah, Sam, appreciate it.