From Zero to Angel Investor (feat. Brian Nichols)

Hello, everybody. I'm KP, and welcome to the Building Public Podcast. I'm super, super thrilled today. I have in front of me one of my mentors, I'd say, when I was at On Deck, but a fantastic human being, a great leader. And, you know, kind of, I could rattle off his whole bio. He's a venture partner currently at Hustle Fund. He was an early employee, one of the early employees at Lyft, at Zoox, and eventually at On Deck. And that's how I got to meet him. Without further ado, super excited to welcome Brian Nichols. Welcome

to the show. Thank you so much. I'm pumped to be here. I'm excited dive in. It's been such a great pleasure of mine to work with you, KP, and just, you know, see you do your thing in such a unique way, which I love that. So let's jump in.

Let's jump in. So Brian, I want to kick it off with the thing that you're doing right now, which seems super refreshing. And like, I can tell you're loving what you're doing. I've seen— I went to your feed right now, and I've seen a couple shoutouts from Eric. And, you know, I think a few others, but tell me about Angel Squad, right? This is the community that you built at Hustle Fund. But I want to know why it came about. Like, what was the Genesis, and then what, you know, how is it going right now? And what's the purpose of it?

Awesome. Well, first off, thanks again for having me. I'm excited to share more about just the path that I've taken in hopes that it helps folks in your audience. And, you know, my story is a little unique. I, you know, started at Lyft. I realized along the way doing, you know, as an operator at Lyft and in other startups that I really wanted to get on the other side of the table and be an investor. So what did I do? I tried to get into venture full-time, tried to find a venture job, and nobody would hire I have a great network. I grew up in the Bay Area. I thought I was a founder before Lyft. I sold that company. I thought maybe somebody would take a chance on me. And this is in early 2018, and just nobody, nobody wanted to. I could not break through. And so what did I do? Well, a lot of the people who were telling me no were telling me that I needed to start building a track record. And how could I build a track record without starting to invest? Well, I didn't have that much money. And so I started a syndicate on AngelList to start investing. And my angle there was to kind of create an alumni syndicate for Lyft folks where I was gung-ho about finding good deals to invest in. I would try to find people who were leaving Lyft who had a good reputation, you know, as an operator at Lyft. If they were leaving to start a company, I wanted to be the first to know about it. So I created this Lyft syndicate, got 200 people from Lyft to join me. I actually got board member Ann Mira Koh, who's a GP at Floodgate, Right. Wow. Lyft's first investor, got her to be my mentor, and she still is to this day. This is again in 2018. And I just started, started getting in the game. And what I realized after doing this for about a year was this thing grew to 1,000 people. I opened it up, anyone could join it. Now it's over 3,500 people. Wow.

And it's still active now, of course, right?

Yeah, still active, still do deals, have deal going right now. And I realized that there's just so many people in the world who are interested in this asset class. How do you get started though? And I thought the way to get started was to get a job at a venture fund, but what about everyone else who maybe they want to do that, or maybe they just want access to this asset class? Maybe they want to learn how to do it. And all these people are in my syndicate. They're investing $1,000 or $2,000 into these startups. And So I, as you know, was running the On Deck Angels program. On Deck is so good at, you know, program building and community building. And but I got really close with Hustle Fund, who had this vision of going after the lawyers, the doctors, the chefs, the NFL running backs, the people all over the world who want access to this asset class and teach them as a venture fund, how do we make our investment decisions? What's our approach? Let's get really tactical. Like, how are we thinking through which companies to invest in out of our fund. And then give some examples. Here are some companies that we have invested in. They're doing really well. If you're interested, you can invest as little as $1,000 into these top-performing portfolio companies, just so that not only are you getting that access, but you're also setting your bar, which I think a lot about as like anytime you're learning anything, what does good look like?

Right?

Learning from Elizabeth Yin at Hustle Fund what good looks like to her, you're— that's a huge shortcut for anyone who's trying to get involved in angel investing. Right. So giving access to people, teaching them, building a network around that, connecting those people to each other from all walks of life. There are, you know, recent college grads, there are retired people, there is a chef in Turkey, there's a former NFL running back, there's lawyers, doctors, all the tech execs, you know, unicorn tech founders too. But that's really not our focus. And so we've, we've really created this special space with Angel Squad, and I'm super proud of it. I'm super proud of the Hustle Fund team for really rallying behind it. We just recently welcomed our 1,000th member, and it's just growing like a weed. So

you're in the 8th cohort, is that right?

8th cohort just kicked off last week. So we've been doing it since January 2021. It's just we've learned a lot about what this customer wants, right? And how we can deliver that. And, you know, I think Hustle Fund is in a unique position as a true pre-seed fund, right, that also just happens to love to teach people. And I don't think very many venture funds feel that way. Like they get energy from teaching, but Hustle Fund does. And that's— oh

my God, I've seen the videos as well on YouTube, right, Eric? And I just felt that there was like— I fully agree, it comes across as, you know, wanting to guide and wanting to mentor and support. It's one of those things that I felt, you know, you know, I'm the ultimate outsider. Uh, when I joined On Deck, I was in Atlanta, even in suburbs of Atlanta, not even like the tech centers. So I had literally no work except my Twitter. Yeah. And the reason I built in public, I built in public and want to continue for decades, is because to me, people like you and people like Elizabeth and Eric and so on. And I just realized that if you just build cool shit, interesting things and ambitious things on the internet, people want to come talk to you and like, you know, you can build relationships. But one of the biggest struggles that I had early on was feeling like I belonged, like, you know, because I had such a nonlinear, non-tech career because I was in corporates, I was in Fortune 500s. I really felt like, you know, I was not a tech boy. Like, I was not like, you know, like a classic Hoodie-wearing tech person, right?

Right,

exactly. And so I was like, is this even for me? But then, of course, within minutes of joining On Deck, that myth was busted. Sure. And I was like, oh my God, this is such a huge myth. The other thing was around your point about feeling like the venture class, venture capital, the asset class, and the people who were sort of responsible for this asset class were not your typical let me hold your hand and show you the ropes kind of people. There was a sense of disconnect from the top-tier VC funds and like the way they conduct themselves was as an average person like me wanted to learn about how can I write a $2K check into Softr, which I did, by the way. Yeah. And so I was like, how do you do that? Right? And so it's like 2 different worlds. And I fully resonate with your potential customer slash, you know, first-time angel, second-time angel is that they're thinking the same things, you know. So

tell me about one thing about that. Yeah. So the thing that kind of pisses me off is that that was on purpose. Like the reason why historically VCs have boxed people like you and me out is they don't want competition for deals. The more competition that there is, the higher the valuation might be. That's not good for them. Every million-dollar increase in the valuation cap or price—

Their percentage ownership.

Exactly. They don't want that. And bringing in a bunch of new people to an asset class that is definitely up and down over the past 30 years since its inception, Right. Actually performing well. So the last thing they want is to welcome new people into it. I take a different position on that, which is if you add a lot of people like KP to your cap table, the chances of you finding your way as a startup goes up because you're getting help from valuable mentorship, right? Strategic—

Matter experts or distribution.

Yeah, right. Distribution, right? Like get Lenny Rachitsky on your cap table, see what happens next, right? Those, you know, probably 5 years ago, they didn't want any on cap tables either. But guess what? He's helping them now. And so I'm a big believer in bringing new people in who are hungry, especially, and who want— it turns out that those $1K, $2K check writers, just like me and you, we are the most valuable people on the cap table. Wow. Not even on a dollar-by-dollar basis. This is just like, I see this now over and over again, because that $1,000, you know, to me and you and to many others, That means a lot, right? Versus, you know, the person whose net worth is $500 million writing a $200K check, they just don't really care that much about what happens there. And so they'll put the check in, but they're going to be more passive versus us. We're going to read the investor updates. We're going to jump in and help when they say, I need an intro to this person. Right. And so you just end up having this much more influential and supportive Right. Group of advisors, mentors, investors in general, people who have skin in the game who want you to succeed.

The other thing too is I think, you know, it sounds obvious when you say it out loud, but I think, you know, because you can relate to them a lot more, I think founders tend to open up a lot more, right? So I had one of my— last year, one of the startups that I wrote a check to was called Airboxer. It's a very Singapore-based startup, very small check. But like this Monday, 2 days ago, the CEO jumps on a call with me and he goes, KP, I just want you to do a copywriting check on the landing page. I don't think he would do that that with the floodgate, or like, you know what? So I went hand in hand with him. And I gave him like specific copy suggestions, because I see a lot of websites and a lot of Product Hunt launches. I'm like, this is what will work. This is what will work. And so that tactical deep level growth knowledge that I just dropped on him is— but also, by the way, I'm doing selfishly because I want him to help me one day. So there's a lot of back and forth, because we feel like we're on the same level.

Well, not only, you know, I love that. I'm not surprised, by the way, that's testament to you and how you would do the same. And I have, but I, it's authentic to you that you would just do that. And of course, you know, hopefully down the road he returns a favor in some way, but if not, that's fine too. And by the way, if his landing page converts better because of the advice that you spent half an hour giving him, your investment is more likely to go up. That's the whole, that's the whole game, right? So that's great. Like, I think it's— Right. Everyone's aligned. I think incentive alignment is very important here. And so, you know, I'm a big believer that this is how Right. Ecosystem is going to continue to evolve.

So from your experience of building this out for about 8 cohorts now, what were some surprising lessons you picked up along the way? Like what was not obvious in the first cohort that became increasingly apparent from, you know, 7th and 8th and, you know, ongoing now that our value prop has to change?

Yeah.

Give me a sense of point A, what was the old value prop?

Sure.

Point B, what is the more refined value prop?

Yeah, good question. And let me Also give a nod to On Deck here too, in the sense that I worked at 2 startups. So after Lyft, I worked at— it was Lyft, then Zoox. Then I was working at 2 under-10-person startups. One was called Blackbird, which was like Lyft for propeller planes. It did not do well, and it was one of the most challenging learning experiences of my life. But the one thing I really learned is to move really quickly to find those insights from customers very quickly. Like everyone who works with me at Hustle Fund is just alarmed at how fast I move. And the same I would say is true about how fast On Deck moved. We moved super fast.

Right.

And, and I learned, you know, to continue to build that muscle there. So now then I started Angel Squad and the whole vision with Hustle Fund was like, let's build this really tight-knit group focusing on the learning and the investing access. And then of course, we didn't announce either the first or second cohort. It was just our friends. And it was like 60, 70 people in each one. And it was our friends. Or like people who had followed Elizabeth, like on her newsletter. Like it was— we were not posting about it on Twitter or anything because we were trying to figure out exactly how this is going to work.

Right.

And they ended up being this incredibly high-caliber group of people.

Wow.

Who were so— we set the culture such that, you know, this was a very vulnerable, authentic space, transparent space, which I think Eric Bond, if you know anything about him, he's like the person to lead something like that. So people really leaned in. And so people came to learn from Hustle Fund, they came to invest alongside Hustle Fund. But once they got to meet each other, they were like, whoa, this is so much more fun multiplayer than single player.

Right.

And so we did a lot of facilitation of reviewing deals together, of matching, just matching people with other people who we thought they would connect with. We really turned on in-person events. And it became one of those things like you come for the Hustle Fund access, the deal access, the knowledge access, but you stay For the friends that you've made.

The peers, the friends. Yeah.

That's right. Yeah. And mentors, you know, all that stuff. And that was something that we just keep doubling down on more and more. And so, for example, we have, you know, events all over the world now in person because we really like to connect those people in person. We're paying for these events. Hong Kong just had an event. London just had an event. Singapore has events like once a month. They're actually our 3rd biggest market. Wow. Yeah. Yeah. And yeah, New York, we just were out there for New York Tech Week, had our own event. It was awesome. So anyway, that is, was one of the main kind of things that we continued to iterate on. And we found this like, wow, if we can just make, if we can help facilitate these connections, we're going to make a lot of happy Squad members. And so, yeah.

What's the vision with the Squad? Where do you think, like, how big could that be if everything worked out, if the momentum keeps up?

Yeah, we set out to get to bring 10,000 10,000 new angels into the ecosystem. 10,000. We just hit our first 1,000. It's been a little under 2 years, so we're about 10% of the way. I don't see any reason why we can't hit that. Right. And, you know, the main machine that's turning here is referrals. People love it and they just keep telling their friends. And so if we continue to build that base of fans and that network keeps on bringing in their friends, I think we'll get there. But what does that actually do for the ecosystem if we achieve that goal? That's like a fun metric, like vanity metric. 10,000. Oh my God, that's amazing. But like, what can— what does that then do? And I think that's where things get a lot more interesting, because these people then go on, a lot of them are starting their own funds. You know, that's not the goal. Some people are just here to, to just be part of the, you know, part of the investing group. But some people want to start syndicates or funds, and, and they are coming from these diverse backgrounds, diverse pockets of the world. And once those people feel like they have a good handle on how to invest and get their own, you know, deal flow in wherever pocket they're in, and then They are investing in those communities. Maybe it's underrepresented groups, right? Or maybe it's geographically underrepresented. So what happens then? Well, you're financing entrepreneurs who are building things that otherwise wouldn't exist because other entrepreneurs don't see that problem, right? And those founders are actually able to get from 0 to 1 because they're getting that support and that help from— Mutual capital. Yeah, yeah.

No, I think the ripple effects are like so many. I mean, there's so many second-order, third-order effects that will like touch so many hubs and probably create more micro hubs too, right? Yeah. It doesn't have to be just the main hubs which already have tech presence. You know, that's awesome. So back to your— the period of your career where you just left Lyft, and I've seen this on Twitter too. You've written a beautiful thread about being the tech mafia syndicate guy, and I love it. I love it. Yeah. It was such a cool tongue-in-cheek moniker. Well, for someone who's never heard about this, Like, what was the premise behind creating a syndicate out of, you know, like, you know, Tech Mafia is, you know, of course, our colloquial term for employees, alumni of a great tech company or network, right? PayPal Mafia, of course, On Deck Mafia, and Lyft Mafia. So tell us how that came about and what was the experience of running it for you?

Sure. Yeah. So let's see. I mean, the main reason it came about, if we think back to what was going on in that period, I mean, I was banging on the doors of all the funds that I thought were awesome. And was pulling all my maneuvers to try to get a job there. And nobody wanted to hire me. Nobody.

Just listening to your story, just can I comment that I'm so glad nobody offered you a job because I don't think we would have seen Angel Squad from you. We wouldn't have seen On Deck Angels from you. And overall, as Brian, as who you are, I don't think you would have the same spark and the fire that you have now if you just got the first job. So I'm kind of low-key happy that they didn't like pick you. But

for sure, man. I am too. I am so happy they didn't. And honestly, they were right.

We were guessing, right?

Yeah. Oh, totally. I mean, sometimes you got to kind of look at what's going on, what's the market telling you, and recognize that instead of turn away from it and kind of run towards the pain. So that's one of the things I've really learned over the years is like when there's pain, I used to try to kind of bury it and try to put a silver lining on it. But now I run towards it, sprint towards it, because it's usually telling you something, you know, maybe about the customer journey if you're running a business. It's like you have some bad news that's coming in. Customers are churning left and right. Why? Like run straight into that fire and figure it out. Hopefully, maybe that's a helpful nugget for some of the founders listening to this. So, so for, for this case though, a lot of these folks who I was trying to get a job from were like, why don't you start an alumni syndicate? You know, we saw that there's this Google alumni syndicate and Zoogler, and it's done really well. It's grown a ton. And I think like some Uber guys are starting one too. Like be the Lyft guy. What's wrong? Why wouldn't you? Yeah, I was one of the first You know, 200 people at Lyft. I was one of the first like 20 operations business leaders at Lyft when we were in San Francisco. My first job was to run all the California markets at Lyft in 2014, and they're like, "You can do it. You just have to put your shoulder against it." So they were the kind of the feedback from them was, "What is your unique deal pipeline? What's what makes Brian valuable to the VC ecosystem as an investor?" And so I took that and was like, "Okay, you know, if I become known as the Lyft guy who." wants to invest in ideally Lyft founder-led startups. But if not, can we pull together this crew from the early days of Lyft that made Lyft unique? Right? It was a very, very unique time to be at Lyft and to be in the startup ecosystem as a whole. If we could pull together that, that army of talent to invest in these companies together, again, small checks, most of, most of the early Lyft people didn't make that much money. Right. So like, we all needed to aggregate our checks into, you know, an SPV, right, and invest together. You know, that's a pretty good sales pitch to tell a founder during a hot market who's got 10 different options of who to take money from. It's like, well, do you want $100K from a bunch of Lyft people who can really help you and who want to help you? Because, you know, a lot of us missed the early days now that Lyft then became like, you know, thousands and thousands of people employee-wise. And so that was the genesis of why I created the Lyft Syndicate. And Mira Koh and I met weekly about deals that I was seeing. The coolest part to me is she's done so much for me. I owe much of my career success, like ever since meeting Anne, to Anne. She ends up over the last couple of years has led, I think, 3 or 4 seed and later rounds of these deals that I sourced for the Lift Syndicate.

Right.

And she, when we reviewed them together, she was like, okay, you know, 90% of the deals that we've talked about are god-awful, but this one is good. Let's talk. Let's get the founder. Let's go through it. And she ends up leading the round. And a couple of those were ex-Lyft employees who started companies. So it's like, it's been pretty cool to add a little bit of value back for Anne. Hopefully those companies end up doing really well. Most of them are doing very well. So I feel really good about that. But she and I have reviewed deals now for like 3 years, and the Lyft Syndicate would not exist without her.

Right. So there's some founders in our audience who I'm not sure how many of them have marketplace place as a business right now. But I want to do a fun segment where I want to kind of get a peek of how you process a deal or you review a deal. So hypothetically, if there was a pre-seed deal at your table, so kind of walk us through what are some things you look for, some signals you look for to say this is, you know, an exceptional deal that I'm going to take it more seriously and going to pass it to the next round or whatever. What are some signals you look for at a pre-seed level? And in this specific example, we can just limit it to marketplace.

Sure. Yeah. Marketplaces.

And that's your, that's your I love

it. Yeah, yeah. Most of it, especially in my— when I first got started, that's really all I was focusing on because I just felt like I knew marketplaces the best, right? It's evolved over time now that I've been in the game for like 3 or 4 years. I feel better about more types of deals, but marketplaces were where I started for sure. You know, there's a lot of— here's, here's what I'll start with, which is from the one thing I wish I knew as a founder is there's essentially like we during Angel Squad, we share this with our Angel Squad community, our framework. Here are The, let's call it 40 inputs that we are looking at when it comes to assessing a company, right? Right. Product, team, competition, market, right? All those things. Within that, there's probably 5 to 10 really important things to think about. Right. And you, KP, might value some of those things a lot more than I do, and then vice versa, right? So for example, on the demand side in a marketplace, one thing that I care a lot about is competition, right? Even in the early stages, I don't like to think, oh, well, what if Google makes a competitor? I don't really like to play that game, but I like to think about what does competition look like in the early stages? How many other startups are building something similar in this space? If there's a lot of competition and if there's a lot of other venture funds who have already participated in that other competition set, then you might be in trouble from a customer acquisition Because there's

so

many

VC dollars chasing acquisition.

There's already VC dollars chasing customer acquisition on the demand side. You could also say the same about the supply side. Let's use Lyft drivers as an example, right? That's the main thing that crushes the economics for Lyft and Uber is so competitive trying to get drivers to drive, to stay, all the incentives. It's super competitive. Right. It's just, it makes it very hard to succeed and very expensive to succeed.

Right.

So the other thing is, if there's already a lot of VC dollars in those competitors, then there's a less— the total addressable market for you to fundraise for your company from VCs shrinks because they're already invested in a competitor. They can't invest in your company.

Right.

So now let's say, you know, you go from already a pretty small pie of people who would be interested in your company to a smaller pie because you have the VCs, the angels, all that group that's already committed to one. You know, the VCs definitely can't invest in yours. Angels can often cross and do multiple in the same space. But so that's kind of one thing to think about. And then also, you know, I, especially for marketplaces, like to think about the founder-market fit, right? Yeah. Why are you the right person to start this thing? Like, do you know something that nobody else knows? Do you have connections that nobody else has? Like, what is the insight that you have that makes you the right person? And why are you going to sacrifice the next, you know, 5 to 10 years of your life trying to solve this thing? Because as a founder myself, like, it sucks, especially in the early days. So I don't love it when the founder or co-founders have just like stumbled their way into starting this company because they, you know, met somebody on the bus and they both had the same frustration. They just wanted to start something. So I love that.

So that's a great insight. And I want to kind of double-click on that because it's one of those things that I learned only after On Deck was this concept of founder-market fit and how invaluable it was in building a unicorn or venture rocket ship. Like, if you really want to go big, you can't skip that much. It's— can't skip that step. Now, only exceptions are like if you are one of those people who has like a sheer force of nature, like you just feel like this person is just inevitable, right? Like, you just feel that, you know, you just know you're in the presence of some madness or greatness. Like, that's okay. That's a rare exception where, all right, you can see someone who is in a whole different industry coming in. I think like, you know, Travis from Uber, probably. I don't know if he was like passionate about transportation, but he was just a barrel of a human being. And you're like, okay, he's going to just run through the walls. You know, there's rare exceptions, which is like 1 or 2%. It may work. Probably less. Probably like You have to be insanely mad about, like, just great about it. Otherwise, it breaks my heart when I see a super talented founder working in a market where he or she has no business in or have no affinity in, right? And the metric that I use is if you launch your MVP today, even if it's a piece of shit, can you get 10 people to immediately give you feedback and check it out and play with it? Because I can do that today in no-code. I could launch a piece of shit. I'm sorry, Not saying piece of shit, but like I could launch a Google Form and call the 19 CEOs of all the no-code companies and give me feedback or get 4 people to immediately pay. I mean, because I have social, you know, we both have social capital networks that I can get that. So if KP is launching something in no-code and somebody else is launching no-code, outbeats you easily just because of sheer existence. I'm not even doing anything, right?

Yeah.

So you want to be, you want to find your version of this where you are so unfair.

Your unfair advantage.

So unfair that you just have the 20, 30 people in your network. And oftentimes what I run into some of these founders is that like, it's a female founder trying to build a men's haircare product. And I'm like, oh my God, I just, I love your passion. But like, yeah, if it's a beard haircare product, and you kind of ask them, like, can you get 20 people on a Zoom call and host a town hall and like take down every problem they have? And they're like, no, it'd take me 3 months. No, it cannot take you 3 months.

Right, right, right. It would

take

An afternoon.

Afternoon to do this. Yeah. So there are some things like, for example, in being an immigrant in America, like I just literally have 25 people on my phone who will immediately jump on a call with me about H-1B problems and like rant about this shit. So if I was building something in the H-1B space, like it's a no-brainer because my best friend Sharath had like gone through all the visas, including me. I just got my green card last year. So again, no-brainer. Thank you. No-brainer. So you want to be in an industry, in a niche where you just have, just by sheer existing, you just have such crazy unfair advantage.

Yes. Yeah.

And that's so hard to convey to a founder because they fell in love with a market or an idea, you know? So that's where I'm like, just spend some time with Idea Maze. You don't want to jump into something quickly.

Yeah. Well, so I love that. And I generally think I find myself saying this over and over again. It is super valuable for any founder or someone who is considering becoming a founder to learn how to angel invest. Yeah. You don't need invest a dollar if you don't have enough capital to do that. But start to figure out what the framework is that, that other people use and build your own framework. Because in order to then make good founder decisions, you then have a huge head start in whether or not you should even start that company. I would not have started my first company if I did this.

Yeah.

Most founders I talk to when I say this, they're like, I wouldn't have either. Right. It's— you're gonna save a couple years of your life maybe if you actually take some time,

right,

and think through what is the framework, right? Angel Squad, I— that's one of the reasons people join. It's like, I want to see Hustle Fund's framework. I want to see it in action. I want to learn what are the inputs, how much do they matter to people, get a better feel for that. Because one of the things is, what is this founder's unfair advantage, right? Why— what is the insight that they have that they uncovered from some special thing? Right. What have they gone way above and beyond doing customer research to figure out this insight? Like, those are some of the things that as a founder we're going to be thinking about when you're pitching us.

Right.

And if that doesn't connect, the answers over here better be really damn good. Like, really good. The market is just exploding and there's nobody in it already. And like, whatever it is that makes you special, if you don't have those founder things, like, some people will just write you off and say, forget it, that matters too much to me as an investor. I can't even take the meeting with you because it just doesn't connect. Right. Right. So that'll happen too. Yeah. So, you know, you got to be aware of that.

To underscore that, I think the other sort of myth that was busted to me was that I thought it was all about getting to the first 1, 2 years, 3 years of a journey. And then, of course, at On Deck, I saw Series B investors, Series C, Series D, and some of these other fellowships. And I was like, oh, this is a 10-year journey. Literally, like, you just have to fall in love with the problem, you know, really, and stay patient for 10 years. So you might as well choose what you're falling in love with, slash, want to solve for the next 10 years, right? It's not a hack. It's not an overnight, like, side project. You literally have to think, all right, is this something that I want to spend 10, 15 years of my life? And but oddly though, right, I felt once you kind of accept this part of the game, you kind of free yourself from, like, unfair expectations. You're not in a sense of immediate results. You could be. I'm very impatient. I know you're like that too.

Yeah.

You— I'm very impatient with action, but very patient with the results because I know this is a decade. Yeah. So it just actually is more fun because you're like, I don't care about this quarter's ROI. I mean, what I do, but I'm like, it doesn't have to show up right away as long as I know we're chipping away at something that's aligned to the vision.

That's right.

And it gives you a sense of freedom that you can operate on a whole different level. You know,

that's right. Yeah. Yeah. I would agree with that. The only thing I would add is if there's some signals that like, you know, maybe this is mission aligned, maybe Maybe this is very goal-aligned, but it's just not working. Like there's no market pull. The market doesn't want it.

Right.

Don't ignore that. Like, maybe be patient with the results, but don't hide under the truth. Yeah. Which is telling you maybe that you're not, you know, you're not, you're not hitting the nail on the head quite yet.

Right. And it's usually obvious in the data. So don't kind of ignore the data, right? So don't like be blinded to it. It's like ordering it. When you go to the doctor for your annual physical, you're saying, I don't care about my lipid profile. You have to care about your profile, right? Like, it's, you have to So that's good. I got one or two questions for you towards the end. This is another thing that I think, especially first-time angels, or operators turned angels, they feel like angel investing is a lot of time investment, a lot of, oh my God, it's a career. It's like a job. How do you— what's your message to them? Right? And you have been in these shoes for how long? Where you kind of balanced, you were full-time at On Deck, you always— Yeah, I was full-time at On Deck. And we were doing that, but also on the side, we're able to angel invest, which, by the way, another myth that I did not know, I thought angel investors were like people wearing Patagonia vests and walking around sipping like lattes and saying, hey, I'm KP, I'm an angel investor. That's— I thought that was the entire identity. I know there are people like that. But we also have people like you and me who are on the side. What's your message to rookie angel investors about this?

Oh, God. I mean, let's see, there's so many things I can tell you. But I guess the first is you can make it as much of your life or as little of your life as you want it to be. So if you want to just review deals and Invest in you know some deals that that come across your email in the morning, then just join some syndicates on AngelList. I would love to have you in the Lift Syndicate. Everyone's welcome into that. Angel Squad, if you want to come learn more, you want to be part of like an active program and community, you know, would love to have you in that as well. So I mean, I think it really comes down to just starting. That's how I feel about most things. Like, if you're thinking about it, just start and get in the game and see where it goes for you. If you want to make angel investing a big part of your life, then not only can you start, you know, getting active in the space, networking with founders, with VCs, with angel investors, sharing deals, joining communities, whatever it might be, your goal might then become to lead a syndicate or to join a fund or to start a fund, right? You just don't know until you get going. But it doesn't have to be a big commitment on your side.

Right.

And you also, the big thing is you don't have to invest a lot of money, right? That's a huge thing that most people think, I can't invest $10,000 in companies. Yeah, most— very few people are doing that. Most people who you see as an angel investor on LinkedIn, on Twitter, they are writing between $1K and $5K checks, probably 90% of those people.

Right.

So you don't need to invest, you know, that much money. Try to invest the minimum in more companies so you get more reps.

Right. So about the reps, actually, I'm glad you kind of led to that. I was about to say, if you had a goal of, I don't know, so let's say if you had $50K capital a year and you're a first-time, second, maybe like you're just a very beginner angel investor, how would you go about allocating this money? Would you say 25 $2K bets? Or would you say very strategic, 2 bets a year? Like, what's your personal— I know it's a preferential thing. Everyone's got their own style. What's your style?

Yeah, I think if you gotta, you gotta start at the top here, which is we are talking about a very high-risk asset class. So generally, when you have a very high-risk asset class, you should diversify into more risky bets, right? Like, anyone who thinks they can pick the one winner out of 50, like, come work at Hustle Fund because, like, we want to know the answer too, right? Guess what? You can't. It's impossible, right? Even the best in the business can't do that.

Right.

So I would say, now let's just— I'm making an assumption that it's pre-seed or seed stage investing, I would probably just go 25 $2K checks. Yeah. If you're gonna do, let's say you wanna do some pre-seed, some seed, some Series A, you can scale up your check size. So maybe if you wanna do a couple Series A, maybe do 2 or 3 $5K checks at the Series A and then, you know, scale down proportionally based on seed and Series A or in pre-seed. But I would say just be consistent. Don't be like, oh, this is a pre-seed, but I like it more than the last pre-seed, so I'm gonna do $4K in this one. I did $2K in the last one. Just be consistent. First Round Capital, who I need to give credit to, they started me on this like angel program journey. I did First Round Capital's angel track in their 4th cohort with like— I had no business in this thing. There were 16 people in these back in the day, and it was now like Parag, the CEO of Twitter, was in my group. Yeah. Nick Caldwell, who's a VP at Twitter. These are stars. And they let me in because the Lyft Syndicate was such a novel thing.

Right.

So I literally changed my life. I owe First Round everything. But during First Round's angel track, they said, we did an analysis of our portfolio and how much conviction we had in these companies and different check sizes and stuff. And there was no correlation between outcome and conviction. First Round, the one of the best seed investors in the world, right? I would say the First Round team, Floodgate team, right? Those are some of the smartest investors. Right. If they can't match correlation, Yeah. Between this conviction and outcome, then, you know, my guess is most people should kind of follow.

I love that answer. And I hope that that's a valuable nugget for someone who's listening for this first time, because I think that's a very counterintuitive sort of insight. You know, we live in the world in this kind of bubble, so it's obvious for us. But I was on the outside. I remember that I was thinking maybe I should chunk up my money and put it in one or two big bets. Of course, that myth was busted very quickly. Again, thanks to the On Deck friends and network I had. later realized it's kind of like how I feel about my side projects. And once I equated that to this, I'm like, oh my God, it makes a lot of sense. Because I actually don't care if one of those projects takes off, the other one's a dud. Like, to me, it's the album, not the song. Yeah. The album is my portfolio. So I want to be known for my albums. One of them will be a breakout hit. Great. It'll be a Billboard 100, whatever. But I can't predict that. Like, nobody— like, Drake doesn't know that. So it's like, nobody knows what's going to take off and what's going going to be well received by people. So it's better to just diversify and kind of like be less attached about each bet. So

I love that. I've never heard that analogy. I

just made that up right now. I think it's irrelevant hip-hop to investing.

Yeah, that was great. I'm going to steal that if it's okay. I'll give you credit.

Feel free. Please do. Awesome, Bryan. That was great. I mean, I think, of course, I wanted to wrap this up by saying how much I appreciate you being here. Thank you so much. It feels like we could go for an hour or two.

For sure.

What is your biggest, you know, sort of ambition for the next 5, 10 years for you personally? I feel I can totally see a chip on the shoulder still. You've come a long way from the Brian who knocked on the doors, and I still feel the chip's still like very clear. So, I'm rooting for you, and I love that aspect about you. But what's next for you? What's next 5, 10 years?

Yeah, that's so good that you can still see that chip. I hope that thing never goes away. I don't think it will. I'm a pretty chippy guy, I guess. But I, I'm all in on Angel Squad, man. I think I've spent a long time in this startup game now. It's been, you know, 12 hard years, I guess, is I think the count now, probably a little more than 12, learning a lot, eating the glass, failing most of the time, you know, being told no more times than yes by an order of magnitude. And we've got something here that's really special with Angel Squad. And with Hustle Fund in general, I just, I think the people that are on the team and that it's attracting are just such good humans. So 5, 10 years, I just want to keep building this thing, make it amazing for those who are joining this ecosystem. And also, you know, one thing that I get really, really fixated on things is something I've learned about myself. And I'm very much fixated on Angel Squad right now. And I don't think that will change for quite a while. But I start to lose some of the relationships that I have with people like you. We haven't talked in a long time, people who I loved working with at Lyft or at Zoox or, you know, so On Deck, like, so, and other VCs that I really like. So I want to— I would hope that 5, 10 years from now, maybe I'm better at staying in better touch with some of the friends that I've made along the way.

That's a great thing to wish for. And I think, you know, it speaks to me too. I mean, I have such a vast coverage as you are. I mean, it's just so hard to keep up with people. But you don't have to worry about me though, Brian. I'll harass you. You know me, I'm always like in your DMs asking like, hey, Brian, I got a lot questions about this world, about this investing side of things, and that's not my day-to-day. So you're my go-to in those things. I appreciate you riffing with me every time. Yeah, so

of course. Oh, please keep bothering me. It's not bothering me, but please keep pinging me and let's do some more calls and I'm happy to come back on whenever you want.

Thank you. Awesome. This is great. Thank you so much, Brian. I'll call this a wrap for now.

All right. Thanks, KP. That was so fun.