Warm Intro

The Founder Who Helped Startups Raise Over $1 Billion

Chai Mishra Season 1 Episode 9

Nick Tommarello has probably helped fund more American founders than almost anyone alive.

But Nick’s not a businessman — he’s a founder. That distinction matters a lot to him and it defines everything about him. 

See, Nick loves risk and he thrives on uncertainty and chaos. He’s good at helping founders because he literally can’t imagine having a regular job.

Join us for a loose conversation about Nick’s childhood working at his dad’s nightclub, how his dad became a millionaire and went broke over and over, how Nick got congress and President Obama to sign a bill and what Nick wants his tombstone to read.

Warm Intro
A conversation, not an interview. Warm, sometimes weird, conversations with interesting people doing big things.

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Hosted by Chai Mishra
Chai is the Founder of The Essential, an ethical commerce company funded by the leading lights of Silicon Valley.

Chai served on the board of UNICEF, and has advised cities, universities, national sports teams and Fortune 500 corporations. A Forbes 30 Under 30 honoree, Chai’s work has also been covered in publications ranging from the SF Chronicle to Business Insider.


Presented by Wefunder
Wefunder created The Community Round.
— allowing founders to raise funds directly from their communities
— allowing anyone to support their favorite founders and join their success.

Raise on Wefunder

Views here are those of the host and the guest. Wefunder makes the show possible but doesn't control who we have on or what we say.

You know, I hate the way people talk about founders nowadays. It seems like we only have two conversations about founders. On the one hand, there are these people who worship a very small group of ultra successful founders. They think the founders of these magical, mythical creatures whose every movement needs to be studied, their morning routines, need to be copied. Their, their biographies need to be memorized. And then on the other side, you have this group of people that. I think has a lot of contempt for founders. They think the founders are fundamentally selfish and and broken people who are held captive by their own ambitions and ego and, and greed. I have a different view. I think that both of those conversations are incomplete and honestly pretty boring to me. Founders are interesting as people. People with insecurities and, and fears and some weird hidden talents. To me, the most interesting founders aren't the ones working on really big companies. To me, the most interesting founders are the ones working on stuff that nobody knows about. Stuff that doesn't matter yet, stuff that maybe will never matter because for whatever you believe about founders, it's hard to deny that optimists start. Companies optimists start everything new in the world. Pessimists don't do that. And that's why, among other things, I want this podcast to be a bit of a love letter to founders, a, a love letter to people who build things. That's also why I wanted to have Nick Ello on. Nick is the founder and CEO of Wefunder. Wefunder is a funding platform that lets anyone raise money directly from their community. You've heard the ad read, I don't need to do it again. What matters is that over the last 15 years, Nick and the platform that he built. Have helped thousands of entrepreneurs raise over a billion dollars directly from their communities. Nick himself is such a founder. Nick is a founder's founder. He's never done anything else. It's how he thinks. It's how he sees the world. It's how he sees other founders. He spends all day thinking about what it means to be a founder, what he can do, what he can build for other founders. In the best ways and even in some bad ways, in some ways that he can't even help. Nick is such a founder. I could not be more proud to have Nick on. And with that, I bring you Nick Tamarillo from We Fund's Office on Mission Street in San Francisco, San. This is warm intro For all these podcasts, we try to come up with a word or a concept or even sentence that we're like really sort of thinking a lot about the guest for you for obvious reasons. I've been thinking a lot about just the word founder. I think that you are, almost like a textbook, like a scientific specimen of a founder to me. Like in all the best ways and even some of the bad ways, like you are the most Foundry founder that I know. I want to kind of take this back and try to understand the origins of that. Tell me, just gimme the highlight reel of your, of your childhood a little bit. Gimme the, gimme the it's a pretty messed up childhood, but I guess the part that's relevant is that my father. It was basically a millionaire and bankrupt like four times, you know, like this never ending cycle. Oh my God. So I have these childhood memories of like, you know, yachts and jets, and then I have these childhood memories of working, you know, 50 hours a week in high school and paying them rent and like working nonstop every hour of the day from 7:00 AM to midnight, building a nightclub with him when he only had like 20 grand in credit card to like. Finance it. So I get the best of both worlds. And I guess from that, like, I guess the effect he had on me is like, I knew from a very early age you can do things. Yeah. And the world will adapt to you. So like risk tolerance, ambiguity, having that belief that you can just like make something happen against all odds, having it work. Okay. I have a lot of questions. Did you. At any point as a kid, were you at all annoyed by this? Were you ever, like, did you hold it against entrepreneurship that, oh God. Oh, it was fun. Yeah. Great. You liked it. Yeah. Yeah. Everything else seems boring. Give me the, can you gimme the, the, the top five list of your dad's? Businesses in terms of just how fun they were for you as a child? The most fun one was probably the nightclub. I was 14 years old. The good part of the job is I got to shine the lice in the pretty girls. He's like, what? What light? Yeah. Dance floor lights. Oh yeah. I was the, was the light on the dance floor. So you got to shine lights in the girls. Was that was, were those. Specific instructions from your dad. Yeah, yeah, yeah. But there's karma. So the worst part of the job is I had to clean the bathrooms when it was closed at like 4:00 AM and not, not a classy nightclub. Wait, where was this? It was Danbury, Connecticut. Okay. Not a, not a famous nightlife destination. No, not a famous nightlife destination. It was called Alcatraz. Whoa. Prison themed nightclub. Yeah. Yeah. That's interesting. That's vibe. Yeah. So that's, that's nightclub. Any other ones? Construction company. I remember when I was six years old, I really wanted to be helpful and I got to like drive the backhoe and then I wanted be more helpful. So he is like dig a ditch and spend all day digging this ditch. And I was very proud of myself, but I think he's had me dick holes for no reason. What was gimme, gimme a little bit of description on your dad. Do you think he could have held the job if he like no. If entrepreneurs, you don't think there was any wor universe in which he could have just had a normal job? No. Yeah. Or me? Yes. Just boring. Yeah. What was he like? What, what do you think his biggest skills were? That, because it's not easy to have multiple success, it's also not easy to go bankrupt multiple times, but it's not easy to make millions is eulogy. I call him kind of like a pirate. Yeah. But yeah, he like, you know, dropped outta high school like no real formal education, but was incredibly like quick-witted. Incredibly street smart, very like smart with like out lawyer lawyers, like just like figuring out how to do it and whatever he needs to know, he'll do. Was he one of your entrepreneurship role models? Brian? It's probably more nuanced than that. I think, like for me it was like, oh, this path, like exists, this path is like kind of fun and exciting. I think I always wanna know, I wanted start a company and I think after I went to college, like, you know, tech companies, not nightclubs. So different, different kind of thing. Let me, let me ask you about. And most of the guests, I've asked them, it's, it's like a bit of a meme of the podcast. I keep asking people how they got into their colleges with you. I wanna ask a different question. Why did you go to college? In retrospect, I was like, I did incredibly stupidly. I think the playbook now is like, oh, get to Harvard, drop out to your company. Yeah, go to yc. You know? Yay. Back then, I was like incredibly unsophisticated. I'm like, I wanna start a business. I should go to business school. What's the best business school? Oh, it's called Babson College, supposedly. I'm gonna go there. Yeah. It's just very stupid retrospect. Either learn how to code, but back then or go to Harvard or drop out. Is there anything good that came from either going to college or getting an MBA? Any other than learning a code? Anything good you learn? No. Yeah, you can spend six years getting an MBA or you can spend like two months starting your company. The two months is like a little bit more efficient. Let's say I'm a 16-year-old listening to this, right? And I'm trying to figure out, I wanna be a founder and I'm trying to figure out whether or not I should go to school. How do you think about that? I think going to college is a special time in your life. Like you're gonna have community, lifelong friends. So yeah, to fall path go to college. But if you wanna really like maximize this thing inside of you that you have to do, you don't need to go to college to do it. Yeah. So I think you should go to college is fun, you know, you can socialize properly. Mm-hmm. Like, you know, enjoy those four years of your life, but it's not like a prerequisite for starting the company. What did your dad think of you wanting to go to college and wanting to get an MBA? Oh, I think he was like proud, but I don't think he realized how the world works in terms of like the tech world. Yeah. Man. Tell me, yeah, tell me about the start of your entrepreneurial journey.'cause you, you had a few ventures right before, before Wefunder. Yeah. The first one was rather incompetently run. So yeah, I got the MBA graduated. And then quite a, kind of quickly realized everything I learned was like wrong. Like, the person who is important is not the person who makes the slide deck and raises the money. The person that is important is the one who actually. Is able to like, build this thing from their soul and make it exist. Yeah. Nowadays, like, you know, yc, take it all for granted. Back then it wasn't conventional wisdom back then. It was like, oh, get your MBA and go raise money with the VCs. Then go give some engineer 1% of the company to go build it for you. And I think it was in retrospect, moose moved so slow. The first company was basically a mobile gaming company pre iPhone, like way too early, complete dark ages. And back then I would pitch it like as this like augmented reality experience where you're like inside of a movie or the main character in a book and you get missions delivered to your phone. You race around the city and find treasure and meet actors. What was this, this 2004? I was very ahead of the curve. Yeah, yeah, yeah. Way too early. And I made a little small business out of it. We had like a good tourism business where instead of like sitting on a, on a bus and hearing some tour guy drone on, you get to race around the city every two hours and like learn about the history and the culture where you are. And then most of the real money came from like, basically corporate team building. I learned that like. These finance guys would maybe like a hundred grand to do whatever I said. Mm-hmm. It's like three hours, whatever. I said they would just like do, like once I put like 5,000 rubber ducks in a pool and gave all these guys in se like nets to go get as many ducks outta the pool as possible. Just I wanted to see them do it. There's no other reason. And then one like guy in his sixties in his suit just stares at me as I'm like, how do I win? I'm like, just dive in the pool and get the ducks. And he fucking did it. Oh my God, dude. That was fun, dude. That isn't, that is like, was it a Stanford prison experiment? Like that level of sociological experiment? Yeah. You take a bunch of finance dudes in suits, super competitive. You just give them any game and they'll, they'll yeah. Pay you a lot of money to play it. Yeah. I guess where that story ended it was five years too early when the iPhone was finally announced. I was told I could be on stage with Steve Jobs mm-hmm. For the original iPhone announcement. Who, who did you, who told you this? Like Apple Senior, like person who's in charge of figuring out which of these apps is gonna be on stage with Steve Jobs. Okay. And all I had to do was take my mockups and actually make the app. And I couldn't code it back then. So I hired, I hired a bunch of people I hired, like I had an Indian firm, I had a Chinese firm. I had some guy in Boston. All three people trying to make this app. Yeah. All three teams could not get it done in time. Oh no. So I basically missed out on being on stage with Steve Jobs. The guy on that stage was Sam Altman. Dude, I, I knew this story, but I wanted to hear you tell it. This is for Looped, right? That's for Looped, yeah. Yeah. My God, man. I, I think I, dude, I, I have so many things that to react to based off what we said. Like, one thing I've noticed a lot now I'll go back to,'cause I did the, the second version of that right. Went to mm-hmm. Goodish School and then dropped out and started my company. And now they'll have me come back and talk to about like, how Berkeley can help you become an entrepreneur. And I always open with the same thing. I'm like asking how Berkeley can help you become an entrepreneur is like asking how the Catholic church can help you become an atheist. Mm-hmm. Like, it's a you're at the wrong place, man. You're asking the wrong question. The, the other joke I always tell about it is I heard this comedian say when his grandfather moved to America they told him the roads were paved with gold. And when he got here, he learned three things. Number one. The roads were not paved with gold. Mm-hmm. Number two, the roads were not paved. Number three, he would be the one paving them. And I think that's what, that's what entrepreneurship used to feel like. Even when I was getting started, colleges didn't have accelerators. They had these like really outdated courses on how you should start companies. And they were just basically borrowed like sort of watered down MBA courses. And I would go so far as to say, I still think this is true for MBAs. I wonder what you think like. I bet against someone, I bet against a founder when I hear that they're having an MBA. That's why I don't tell people that you outed me. You literally outed me. No thanks man. No, that it's, why, why do you think MBAs are so historically bad at starting companies? There's probably some adverse selection in the pool of people who want to apply to them, myself included. Yeah. I think I was just very naive. Like, I wanna start a business. I need to learn how to start a business. I'm gonna go to school so they can teach me. Yeah. It's just like, usually it's like you have, the agency is like, I wanna start a business. I'm gonna go start the business and get started now, and I'm ready. I don't need anything except like my sheer drive to go do it. Yeah. And then part of it's just like you just. Can't read a book to learn this stuff. I mean, the whole thing of trying a business is defaulting to action and velocity and speed, which is like the opposite of like going to school and, and I mean specifically MBAs to me are, when you think about people who go get MBAs, I think it's very specifically people who need two years to just think about what to do next. That or status or safety or indecision if they want to go into banking or finance where you need a credential versus actually start the company. I think it's a genre of people who think it's like kind of fun and cool to start a company, but don't really want to go through the pain and grind and perseverance. Then might dabble in it but not really, really want to do it. Dude, my favorite line about Silicon Valley is you know, it's a bubble when the pretty people show up. And I think I feel that way about MBAs, but I, I do also think that it was like a. It feels, hopefully, fingers crossed, that it was a blip in time, that it feels like companies used to be started by people who had, you know, I'm talking thirties, forties, fifties, all, all the way really up to like the eighties that companies were started by people who had deep product knowledge. You know, the guy that came up with Coke, presumably loved making Cokes or making, making drinks and then came up with Coca-Cola, whatever. Right. It was started with people that had a product in mind are to drive, to make a thing, and then the economy got much more financialized. Right. Starting the, in the eighties and it became much more, and then like the whole like Jack Welsh, GE principles of like, you know, you know, you don't need to get good at any one particular business. You just need to get good at business, period. Right. And I think that it also feels like a bit of like an overhang from that. And now I hope what Silicon Valley has done is kind of brought us back to more like, you know, you need to be good at your business. You need to be good at product, and you need to have drive for your thing, not just be generically good at business. You react to that. What do you think? No, I think there was a time in society when people thought you can train business workers like an industrial process and middle of management was like this. Technical thing that could be perfected. And then you had to like understand these skills in order to run these gigantic companies at massive scale. And I think what you've seen in the last 30 years fragmentation, where, you know, if you grew up in the forties or fifties or sixties, like. You want to like build rockets, you'd go to NASA and you go work alongside a hundred thousand people to go build a rocket. Now you get to go to SpaceX or Blue Origin. Mm-hmm. Like smaller, faster, moving high velocity teams. And I think Silicon Valley is like the extreme version of that. You just go to YC with four people. You can out, you can run circles around Google. This was not on my list. What decade do you wish you were born in? I'm gonna be millennia in a decade. I dunno, maybe, maybe 500 BC would be kind of cool. That's not, well, that's not what I expected at all. What, why 500 bc? I don't know. Like, just curious what happened. It just seemed like life was more meaningful back then. Like, I don't know. Do, do you think you would've been a founder in 500 bc, whatever the equivalent was? Maybe a explorer. I think actually what I wanted to be was Indiana Jones. So I guess the decade question, maybe 19, 20 so I can go find some lost treasures. Yeah. It'd be kind of cool, like, you know, founding a country kinda neat, you know, go, go get your tribe and go across, like, go like across the sea and find the other island and take it over. So tell me when you first started thinking about Wefunder, when you first started thinking about starting this thing. It was like, I think like October, 2011, and then I heard that the house was debating the law to legalize it so that normal people could invest, not just the wealthy. Yeah. And that like, like interest in me because I knew I always wanted to invest in my friends, always thought it would be like, kind of impossible. So I never really pursued that line of thought, but I'm like, oh, this would be really cool. Like, there's so many things I wanna invest in that aren't public or my friends or things I use. Because I mean, I, me pretty excited that this could actually like, be a thing. Yeah. And that's what kind of led me into like the lobbying effort. Mm-hmm. Tell me about that.'cause presumably you knew nothing. You, you probably didn't know anyone in Washington, right? Like no one. Yeah. What was the first contact you made? How did you even get started with that? Let's me. All right, so in January, 2012, I just made like a little website. I basically did a hack where instead of just saying I support this bill, it's like, I support this bill and I would invest like X dollars if it was legal. And I kind of engineered it. So that number was like, you know, like, I think like$10 million in like a few hours. It's like$10 million, wanna invest in like creating jobs. Mm-hmm. And then got that like, mentioned a lot in the press. And then I had a friend who had another friend who's gonna present in the small business committee in the Senate or something, and they displayed the website like two days later and they're like, oh, wow. So much money is waiting to be, you know, invested in like job creating small business owners and founders. Then from there I basically lined up a bunch of introductions so that I could went to DC like a week later and met the staff. So three different senators. The president's office and a couple congressmen. You met with President Obama, right? Or no? His his tech person on this. Doug Rand. Did you I, I've seen a picture of you with Obama. I, I did not shake Obama's hand. I was like, maybe in the vicinity. Well, what is he like from a, I have no idea. No. So you, by the way, like, I don't think this is talked about enough. They're like, they're accomplishments for entrepreneurs that don't even register on the map of like, I think civilians, right? And getting a bill passed so that you can start the company and build an industry is like fucking tippy top like that is very few entrepreneurs can claim to have done that. I mean, devil's advocate is just had good timing. Tell me about that. What do you mean by good timing? The narrative in the country is like the post 2008 period. It's like the economy's kind of like sputtering. It's not like strong enough. We need to create more jobs, which is like a pretty good moment for a bipartisan like capital, like formation as they call it. Like how do we give more capital to founders? Yeah. It's like one of those rare moments where a bipartisan bill is actually possible. Yeah. And so if that whole narrative didn't exist, it wouldn't have worked. Tell me. Let's, let's linger on this for a second. So I get the sense, not just from you, from everyone that works at Wefunder, that you know, the whole like missionary versus mercenary thing that's very popular and Silicon Valley Wefunder, I think is a missionary company. And I think that there's like a deep kind of moral drive and what Wefunder does much more so than I think most of the companies that I've sort of come across in the valley. You can tell me if this isn't how you think about this, but I don't think for you. From my interactions. I don't think it's as simple as like, oh, this is good for the economy. This is good business. I think you think it's morally the, the better path morally, this is what we should have. Yeah. Is that correct? Yeah. I mean, moral is a heavy word, but and also it kind of switched over time for me. Like, I think I started the business more on the investor side. Like, it is wrong that I can go gamble in Las Vegas, but like government isn't stopping me from investing in things I really want to invest in. Yeah. If I go gamble, that makes no freaking sense at all. Yeah. And now I think what drives me more is like, yeah. In Silicon Valley, this is not like the biggest problem, like, you know, relative to other regions in the world, money basically falls out of the sky. You'd be 19 years old and raise like$5 million for like your thing that was a, you know, didn't exist like two weeks ago. Yeah. But across most of the globe, that's like, doesn't work that way. And it frustrates me to see like, so much like raw potential, so many talented people who don't have. Either the self-belief the people who believe in them or the money in order to actually go down this path where they actually could do what they care about. So that kind of drives you more these days. In an ideal world, do you think we have twice as many entrepreneurs? Do you think we have 10 times as many entrepreneurs? I think it's a little more nuanced. I think not everybody really should be like, you know, a founder, founder. It's like a very hard, gruesome path where you're being punched in the face over and over and over again. Yeah. So people have to really like, want to do something and so maybe there's like three or four or five times more people out there who, if they believed that they had the capability, that they can go do that. But I think it's also really good to be on a founding team. Yeah. So many more smaller companies started with people aren't a cog in the wheel, but actually feel like real ownership, whether it be the founder or the founding team. That to me is like much more interesting. Dude, I think this is the thing that isn't talked about enough is I don't know how you solve this problem. I'm not smart enough to know how to solve this problem, but, it's crazy how few people have a true sense of meaning around their work. And whether you get that by being a founder or being part of founding team, I would love for that to be 10 XD or a hundred x. I don't know, man. I, I don't COVID really, I think like exposed this. I used to live in this building. They had like a big window'cause there was a loft. And I would see across the street, you know, these like apartment windows. And every morning you, I would see exactly around like 8 55 people would walk out, not wearing pants, but wearing the top half. Right. And they would, because they'd all push their desks up against the window. So I could see like a grid of four by foot 16 windows. Mm-hmm. And they would. Plug into their desk and they would sit down and then I would see as the, the evening would come on that the, the lights would go down and then they would all turn the computers off. They would leave. And the morning reminded you, you see those like videos of like factory forms where they plug in the cows? Yeah. Yeah. And they just extract value. Yeah. That's what it felt like. And I, I have a hard time imagining that anybody felt like that was a good, you, you have a phrase that I really like you say, is it worth my life? Is it, am I saying it correctly? Right. Close enough. I don't think any of those people thought that that was worth their life. Mm-hmm. If you truly believe that you're gonna live once, if you truly internalize Yolo. Why the fuck would you want to do live that kind of corporate life? I genuinely don't. And maybe this is, say more about me. Safety, comfort, status, all, all false illusions, I think. But man to me, dude, like safety and comfort or shit, if you don't feel like, like moment to moment what you're doing is worth it. I, JJ I'm not, like, I'm telling you, I'm, I'm with you obviously, but I you the wrong guy to explain, but okay. But let's, let's, let's bring this back. So fast forwarding 15 years, almost 15 years, right? 2011. You get this bill passed. It is now 2025, almost 2026. Over a billion dollars raised on way funder, which is a mind boggling number, right? Billion billionaires raise in, invest in Wefunder. Let's start the very like, stereotypical question. What's been the most surprising thing to you in the last 15 years? About this business, about this industry, about being a founder at this scale. Yeah. I have a hard time answering that question because the things that were surprising now to me are just conventional wisdom. Yeah. So I like rewind my brain to like the past. Yeah. And like, oh, what surprised me. I remember I wasn't really surprised, but I remember being really pleasantly happy that after the four to five year wait for the regulations to. Roll out mm-hmm. That people actually wanted to invest because like, you know, most startups, like you have an idea, you go talk to your customers, you get started to most later you have data. This one we had to wait like five years. Yeah. And so, you know, finally in 2016, those regulations actually happened. Five year wait like, oh my God, this is great. People actually wanna do this. This is amazing. And then watching all the notes that investors would write when they get to invest in their favorite founders or companies is like incredibly like heartwarming. Yeah. And so in a sense it wasn't a real surprise, like I bet like five years that this would actually happen. But it was kind of cool that I was like that what I felt other people felt too, they wanted to support people they believed in or the companies they cared about. I still have a folder on my laptop with the best messages we got mm-hmm. From people, a truck driver in Idaho left me a message in the, after investing in my We funder campaign and said, I'm, I'm like, I, I, it's an exaggeration. Said, I'm getting emotional thinking about it, but I, like, I, I am feel very sentimental about all that. He left me a note about saying I've never invested in anything. And this is the first time. And we had teachers mm-hmm. From the south and you know, like God, accountants from California and we just had, we had like random uncles just random brown uncles from all over the world that invested. I, those are the categories of people in my, I just, it, I think like one thing that is not. I was, I, I wanted to push back on some of the core stuff around Wefunder, but I can't really effectively do it given my track record of having these three Wefunder rounds. I'm just not a credible two biased actors. Exactly. But it's I think like one thing that wasn't, I know why Wefunder can't do this in the marketing, right? Because nobody would believe it. So I can kind of talk about it as a. I talk about it in these ad, in the ad read for the show too, but it was a good low. It was, it was a spiritual experience for me raising that round, especially that second one that we raised. Because I was convinced that everybody hated us. But what it was was that everybody in the valley very specifically for a short time period, hated my industry. And I took that to me. Not you personally. Well, that too also, I'm sure. But I was convinced that people hated what I was doing. Mm-hmm. And that nobody wanted us to exist. And I raised that refund around. And we were, we were outta money. That's my bank. The bank account was my proxy for figuring out how much people liked us. And we raised a refund around, and I think it was like, I'm gonna get this wrong, but$200,000 in the first couple hours, and it, it, dude, it like, it changed the psychic energy of the company where all of a sudden people are like, no, no, no. Like there's this great Bob Dylan. You know, Bob Dylan starts playing rock. Mm-hmm. And people are like, people start showing up in his tour in UK just to boo him and he's like, his band is just like, what the fuck is going on? Like, we we're, we're here to play music. We just get booed all day. And one day he shows back up and he's talking to the band, which is called the Band, and he says, you know what? They're all fucking wrong and we're right and we're gonna keep doing this. And then that totally changed how they played their music. And that's how I felt that we found around was for us, where I was able to go to my team and be like. Fuck all of them. We know what we're doing is right, and I don't care if anybody else sees it. I know these people see it. Yep. And it totally changed how we felt about the business. But anyway, so that's my little, this will replace the ad read for this, for this episode. But what's been the most surprising thing to you about managing a team? I dunno, there's this moment in 2022 when we were briefly like 90 people. Yeah. And then just seeing how. Fast that like bureaucracy and complacency can infect any sufficiently large org headcount, even only 90. Yeah. And then just seeing like things that make no sense happening and seeing all those bureaucracy, I'm like, what don't you feel like, don't you care? Don't you feel like ownership over this? We eventually like downsized the team by half when the interest rates went up. Yeah. And then with half the people, like we just did like three times more stuff. Yeah. Dude, it's like you, I think you intellectually know that when you like live through it, it's like, oh, half the resources we got like double the output. Yeah. Because less friction, less bureaucracy. Then see my role in that. It's like, so the next time I get to 90, like how do I stop that from happening again? I, I'm actually really blown away by'cause my, my wife is mostly working in big tech. And I'll talk to her and it's like there's one in a thousand companies that are able to scale past a hundred people and not become like obnoxiously bureaucratic. And I think it's just something about people, it's just comfort in numbers where you can kind of just like, oh, there's, there's 89 other people here. I'm sure somebody else is doing it. And you always wanna understand everybody else is doing and have them check in with you. Everybody wants to be in the loop. There's an insatiable need for information that can never be quenched. Yeah, dude. Are you, are you a fan of the, the Amazon two pizza? Yeah. Yeah. Yeah. I tried to put that too. Yeah, that helps a bit. It's for people that don't know, it's Bezos I think had a rule, right? That like, any meeting. No meeting should be so big that it can't be fed with two large pizzas. Mm-hmm. I'm a fan of that, but so coming, coming back to this, do you think we can cut this out if you don't want this in, but do you think that Wefunder and Community Rounds were blackballed by VCs? No. I dunno, it seems that the, the best VCs like Andrew Horowitz like has no problem with this at all. Yeah. It's like no big deal. And then maybe there's like third tier VCs, like who live in the Midwest, who are like 90 years old, who are like, don't do that new thing. That's like actually more over 10 years old. It might scare off the VCs and so there might be a perception among like the second or third tier VCs. But I mean, Substack, rept, mercury arrived, beehive, like we've funded of good venture backed companies. No problem. Yeah. And how about Wefunder itself? Did you, what kind of reaction did you get when you would go out to fundraise from VCs? Did you ever try to do that? Only once and we never actually, I mean, the cool thing about Wefunder is that we eat our own dog food. Yeah. Our own customers have given us somewhere over$20 million over the last decade. Wow. So we've never actually had to raise money from VCs. And I think I. Like VCs like can be wonderful if you're the exact company that needs it at that point in time, like you are on the rocket ship, you can easily take, you know, a hundred million dollars and then you know exactly how to turn that into a billion dollars in a couple of years. Yeah. If you're that kind of company, it's great. I think what's much more common is that you, you know, get the a hundred million dollars and you completely blow it. Build a really bad business with no actual sustainable value. Then you go bankrupt. And I think the nuance thing is that you can actually have a pretty good business and then still destroy it by overfunding everything. Yes. And so I think we funders had like consistent compounding growth that we can basically fund with the money we have. And if with the exception of like late 2021 was like peak erp, peak COVID and like, oh this is it. We finally 10 XD in a year, we can 10 x again. That's the only time period where actually like actually went out and tried to get VC capital. We got a term sheet. It is a long story, but yeah. Do you like VCs? Just at a personal level. I, I'll, I'll, let me, lemme come out with my take. Mm-hmm. So just so you feel comfortable saying this as a group of people and We raised VC funding for our company and I'm sure I will raise VC funding for other things in the future. I found venture capitalists in San Francisco to be a more humorless group and just a generally more kind of devoid of charm. Than any other. I'm generalizing. Obviously there are some amazing VCs. Some of them are very good friends of mine. Some of them were my wedding invested. So the ones that that gave me money were, they're amazing. Generally else were humanitarian. They, they deserve the Nobel Peace Prize. But, but there were you there, there are obviously good VCs out there. Some I assume my good people. But no, I, I really found, if there's something about that industry, man, just like the BA thing, and I mean a lot of the MBAs going to become VCs. Yeah, I just found it to be like my, my simple test for for whether or not I like somebody is how often I see them laughing at themselves. And as a professional group, I find VCs laugh less at themselves than almost any founders. Take themselves for the most part, very lightly. Mm-hmm. Because you get the shit kicked outta you every two hours. And VCs, I think like, because you constantly have these very smart people, founders sort of sucking up to you and like trying to get you to be part of their thing. They get such big heads and they just, I don't know, I, I, I wonder how you feel about this, but I found personally a lot of VCs to be very unlikeable. Yeah. I have no problem with VCs probably'cause there's like, there's so many different kinds of humans that label can describe. I think I'm more naturally drawn towards the builder types and there are builder type VCs. They might have been a founder in a previous life. Yeah. Or they've been like a really strong operator and they've been through some measure of grind and they have some wisdom from that they want to share and like I definitely respect those people. There might be the more annoying genre of, you know, the person in their mid twenties who has never actually built anything who is like the junior associate Yeah. That thinks everything they say is like bold and they're really, really smart and they don't actually understand anything. Yeah. That's more annoying, but you know. It's, everybody has to go through that phase of life, you know? Yeah, that's true. So it's just a natural phase of life and in five years they'll probably figure it out that actually they don't know anything. Yeah. Got, I wonder what the,'cause I know what it is for founders. I know what like puts your ego in check. They're like a billion examples of things that, like you, your ego literally is not allowed to grow for more than five seconds uninterrupted. As a founder, I guess what I, what I dislike is that. Just by the nature of the job, they are giving money. They have high status Yes. In the perception of the universe. Yeah. When someone can, you know, be 24 years old and have never built anything, but they have like high status because like some VC hired them to be an associate. Yeah. That like, I think is a little backwards. I actually think the high highest should be the people in the trenches building the thing. Even if they're failing. Yes. Do it up. The most upsetting version of that to me is when I see founders giving them very high status. Yeah. Mm-hmm. I'm not, you should be kind to everybody as a founder. If you can do nothing else, be kind to everybody, right. Be kind to most people. But I see it with my founder friends, and it's like, I, it's a post seeded round or post pre-seed sort. Hangover where you see they start to, because VCs were trying to woo them. You know, you just fresh outta yc, maybe you were one of the hotter companies in the Bash and people were trying to woo you. And I see them, I go like two to three weeks without seeing'em, and then I, all of a sudden I run into them and party and they've started to dress like VCs and talk like VCs. And I'm like, oh no, my guy, you're, you're on the wrong track. Well, we, we shouldn't do shit on VCs. There's definitely the, the kind of hot shot founder that just like. Start at the exact boom, and like everybody says, they're brilliant. Yeah. And then six months later they flame out because like, it was just a, you know, that's just how life goes. Yeah. I think like what you can never remove is just the status games from any industry. Right. But anyway, now let's pull this away from VCs. Let's bring it back to founders. I, I, I genuinely don't know anyone else that spends as much time. Being a founder, thinking about founders, helping founders as you do, you'd like professionally help founders, right. If I were to, if we were to, let's workshop this together. If we were to create sort of like a ello doctrine of entrepreneurship what's, what's in there? Like, what is, what to you goes into being a good founder? What are the qualities of a, what are things that you, you think founders shouldn't do? And it's fine for this to be subjective. It's supposed to be subjective. Yeah, I think I'm just brainwashed by yc. I think kinda the way same YC is like the answer. Yeah. High velocity formability, running through walls, figuring out how to get the mission accomplished, being adaptable, being resilient. Talk to customers, build a product, talk to customers, build a product faster and faster and faster. Default to action. These are all like common sense generic things. But I think is deeply true. I also, I would add to that, like knowing what a vanity, what, what, what vanity metrics are and vanity successes versus actual success. Like I loved, I think the strongest lesson I learned going through YC was when I first walked in and saw their office. And it's, for anyone that doesn't know me and the new office is kind of nice, but they, back when we went through Wesc, it was. Dude, it could have been like a Coldwell banker. Like it was white walls, one gray couch, couple of pictures that are way too small for the, for the wall. And that was it. Right. And I remember, and there would be like tour groups of tourists that would come back'cause they'd heard about yc. Mm-hmm. And buses would stop and they would be so disappointed to see that. It was just, it looked like a, like an office, like a accountant's office that, a strip mall. It was. To me, like, have you noticed this thing that people who go through YC start to sound similar and like, I, I think it changed how I talk? Yeah, they definitely, I'm not sure they use all the same exact words, but yeah, it definitely changes how you think Your number one operating principle, at least for me, it became clarity. Mm-hmm. In, in thinking and clarity and communication. Even now when people ask me like, how do I get into IC that's the main thing. I mean, I'm curious about your advice here.'cause I'm sure people ask you, to me, the big thing is like, it's almost not about the ideas and it's not about any, not almost, it is definitely not about the startup idea. It's about your. Act, your bias towards action and your clarity in explaining the startup idea. Yeah, and I think that clarity comes from like deeply thinking about your customers, like obsessing over it. You know, sometimes people apply to IC the week that's like, and I, you know, a week old, I do this a week old. That's totally fine. But the people who like really think through every single detail go deeper and deeper and deeper. I think they stand out during the interview. Let me, let me give you a couple words, if you can rank these for me in order of importance for you, right, just in your life. The word community, having a, having a community personally adventure, accomplishment and recognition. Maybe recognition could be put with a slash, which is slash status. Recognition of status is at the end. I don't think I've done things to maximize that at all. This is one of the very few podcasts I even do. So then there's adventure community and accomplishment. Probably accomplishment first then. I think my heart says community, but I think I go for adventure more than community. So I was really curious to see if you would see through. Yeah. Yeah. So I guess it's probably the way I've actually lived is accomplishment, adventure, community recognition. And what kind of accomplishment do you care about now? I know justifying my existence. Like I lived on this earth for, you know, a brief period of time and it mattered. Hmm. That's, that's a rich idea. It mattered. Yeah, every founder. In what way do you hope you will have mattered your existence? Will it mattered? I don't know. It's like every founder that Wefunder helps fund or helps like put them on a path. Every person, those founders hire, every customer that those people help. It's like, seems like a pretty good way to like. At least in our modern day capitalist society to have lots of companies out there like improving the world. And if I can play some small part in that engine, then I think it matters. Do you think about that sometimes just laying in bed, can't sleep? Do you like imagine the scale of what we funder's already done in that way? I'm just very short term focus on what we're do next, next week, the long term's. Lucky. Scale it out, fund thousands more, fund billions, more more money going to people who wanna do things. Cause I used to have a version of that where I would think about, you know, as an e-commerce company, I would think about the millions and millions of times a day our products were being touched and used. And that used to make me, like, in my worst moments when I felt like we'd really accomplish nothing, I would just think about that and that would gimme a little bit of solace. But that, that's actually a beautiful idea, man, to just. To exp expand and that, I think that's why founders are so important. That's why we need so much of this. That's why we need Wefunder is to like,'cause the, the impact of it is way more far reaching than you just helped one person start one company. Right. I was gonna say that's also I guess why YC is called Why Combinator? Yeah, same. Same principle. Exactly. Okay, so I have a theory about you and I kinda want you to respond to it. I think you, you know, you mentioned at the very top. Risk tolerance and like this kind of comfort with with new things. I'm gonna say not only are you, do you tolerate risk? I think you like risk and I think you like a little bit of chaos. I think you want a little bit of chaos in your life. I think it, and I'm projecting, but I think it makes you feel more alive. Do you agree with this? I'm thinking. There, the, the rational part of my brain says risk is necessary. And within Wefunder I consider my role as breaking up the complacency. I think people generally wanna play it safe and are not comfortable, like taking some risks that have bad consequences. And as CEO of Wefunder, I do the option extreme, so people go a little bit towards me. Mm-hmm. It's like, no, this is the only thing you can, we wanna move fast enough, we have to take risks. Yes, yes. Do I just like it? It makes it more exciting. Yeah, probably. But I don't think of like risk in that way. I don't know. And I think of the highlights of my, like professional life is like when you have a small aligned team doing the impossible and then you do it, that's cool. Like everything's on the line, everything matters. Everybody's just like pure executing. There's no bullshit, and then you like accomplish the mission. Those are the best moments. What does your watch say? Yeah it says failure is not an option. Do you remind yourself of those words often? These days I haven't needed to thankfully. But I got this watch in one of the harder years of my life, 2018 when like, everything almost entirely fell apart. It was the, for the most gruesome part of the grind. And then, you know, we got through it and whatever, but I think the mantra was, failure is not an option. Just keep on pushing through. Do you have any other mantras like that? I haven't heard you say a couple probably what, what you heard me say. Well, gimme the, gimme the line about cowards. I actually forget the exact words of this, like, the cowards never, the never started in the week. The cowards never died along. The cowards never started and the week got along the way. Yeah. That's also a 2018 thing. The co never started, the week died along the way. Yeah. I answered that also in a while.'cause my slack message still, but I, I haven't updated that in a while, dude. I it's crazy. Like how much I was always surprised by where, where those like words of wisdom came from for me when I was, i'm going through hard moments with the company. I remember, God, this is so embarrassing. We were going through, I don't know, one of 300 times that we ran outta money, right? And. It just, it seemed truly like impossible to overcome it. And I, my brain kept trying to find ways to like sort circumvent it and all that. And then I was at the mall and I saw an Under Armour ad and it said the only way out is through and I made it my wallpaper, you just brought a bunch of Under Armour a and so then I went all in on Under Armour. And that saved the company. No, but okay. Let's talk about zooming out. You know, Wefunder is part of your professional life. Your professional life is part of your life overall in your life. Actually I'm curious about something. Who do you think has in your life understood you the best? I don't really feel well understood, so probably no one. That's why I'm asking. Yeah. What do you think has understood you the best? It's still Aons up there. Okay. That's our producer do want, I dunno. She really should have been, I tried to get her to do this interview, but she didn't. She, she done so many times. Yeah. No, it's, I, I, I imagine it would, it's hard to ask the same question over and over, but, um hmm. All right. I have, I have one last question for you. I think I know the answer you just gave up with that line. Well, no, I think, I think you answered it. I think it's what I did. One, one person I did wanna talk about that I, I kind of, I think I sort of omitted at the beginning with, I did wanna talk about your grandmother a little bit. Tell us a little bit about her. So she raised me from 10 years old to 15, is probably why I'm somewhat functional. And she has a pretty cool story. Well be cool is the wrong word, but she stopped school in eighth grade. Had to go work to provide for the family. Got married at 17, had a kid at 18, got divorced at 19. Had to be a single mom in New York City in the late fifties, early sixties, like providing for her family. It's like one of those people that's incredibly wise, but like hard earned, like life wisdom versus like, oh, I went to school and I'm book smart. It was like, in some ways the smartest person I've met and very, very strong given all the universities you went through. I, I have a final question for you to, to finish this thing up. I think I know the answer, but I I still wanna ask it. When you die, if you die probably gonna die. Yeah. It seems like one of those things that's almost guaranteed. It is a two bother. Number one, what do you want your tombstone to read? And number two, would you rather die completely irrelevant or deeply disliked? Alright tombstone he mattered and disliked, he mattered. And hopefully not, but if it has to be disliked, but deeply significant. Well, I think if you accomplish anything, there's gonna be like half the people who just hate you. That's a great place. The best is the way it works. I think we should, we should all aspire to do things where we have haters. Yeah. I think because good to have like strong feelings one way or the other. Just apathy is the worst. Happy. These is the worst. Nick Tomillo, thanks so much for being on the podcast, man. Happy to be here. That was one of the shortest, was it? I think so. I think I'm more concise. Yeah. Nick Warm Intro is produced by G one Moon, associate producer Alex Seko audio and video work by Gin Han, hosted by me.