The Rise of AI-Powered Services + Ultimate Sales Crash Course | Chris Hladczuk, CEO of Hanover Park

Everyone I talked to, they'd be like, oh my God, I keep talking about internally how we should build this tool and this tool and this tool. But the problem is, is they call engineering there IT. They don't even have engineers.

Oh no, that's not a good sign.

So they think about the best developers in the world. Are they ever going to join a legacy fund admin to go build the product to make this 10x better? No. And so my pitch to them is we have the cracked engineering team, we have the accounting experience, and we have our early batch of customers. Let's go win.

Welcome to The Peel. I'm your host, Turner Novak, founder of Banana Capital. Today's guest is Chris Hladchuk, co-founder and CEO of Handle. Our conversation is filled with tactical advice around breaking into your first startup role in founder-led sales.

Send your CEO weekly updates on what you did this week.

We first met on Twitter, and Chris shares how he went from 0 to 100,000 followers in less than a year.

The first time Sean ever opens up a Google Doc to write a Twitter thread, He is writing one of 7 viral emotions, and one might be,

he shares everything he learned going from a sales IC to chief revenue officer in 9 months.

Think about every single moment that you elongate the sales cycle as a chance that the deal will die.

How to send a good cold email.

Short, specific, and spacing. 5 lines or less. And then the bonus tip I'll give for people— this is something I shouldn't be saying publicly.

What he learned from Michael Seibel.

What keeps you motivated building YC? And he's like, I'm obsessed with institution building.

And how he thinks about vertical integration and the build versus buy decision.

Instead of outsourcing our general ledger, we built it ourselves. That gives us flexibility to build better and different products on top.

Before we talk to Chris, I publish new episodes every week exploring the world's greatest startup stories. Subscribe and check the link in the show notes to make sure you never miss an episode. Chris, welcome to the show.

Thanks, Turner. Thanks for having me.

I want to hit on first, you just launched Handover, your new company. What is it?

Fund administration is probably the word that any GP listening to this does not care about. They're like, wait, it's this like specialized accounting firm who does this back office stuff that I don't even think about. What we saw when we looked at this market is my hot take is that B2B SaaS is dead. And so what B2B SaaS is, is if someone wants to have QuickBooks, that software to make you slightly more efficient than an Excel spreadsheet, spreadsheet for an accounting firm. What we think now with AI is that you can sell the work itself, meaning no one wants a slightly better QuickBooks. They actually just want the work done for them. And so if you think about 20 years ago, venture capital funds, private equity funds, private credit funds, all of them did all this accounting stuff in-house. Now 70% of the market outsources it to these specialized accounting firms called fund admin. And so, you know, we obviously built from ground up like a next-gen fund admin, but if I went to a GP and said, Hey Turner, we're gonna give you slightly better accounting. They would laugh in my face. And so the secret here is that typically this data is siloed across 7 different systems. And so what we— 7? Oh my God, like— What? Bill.com, Excel to glue it all together, QuickBooks, because all the legacy admins are accounting firms, they're not tech companies, right? So they don't build the whole thing vertically integrated. And so we're like, all right, if we have all of this data, can we build this copilot on top of all of this unsexy accounting data where you can say, hey, Tell me my top decile portfolio companies by revenue growth, or what are my top 5 positions for fund 3 and fund 4? And so that's the thesis here, not just better fund admin, but actually delivering alpha to these venture funds.

Interesting. Well, so if I'm your average customer or future customer, what am I probably doing and using right now?

Yeah, right now you're probably using a legacy fund admin, and then you might be paying $25,000, $50,000 a year for 3 or 4 different tools that do portfolio modeling or portfolio management or all of these things. The problem is, is the fund accountants can't build this like operating system, which might be the portfolio modeling or the portfolio management, and all these overpriced SaaS tools have to wrestle all the data from the legacy systems to make it work. And so every time you do a deal, you or your finance team needs to like take all the information from the legacy fund admin systems, poured it into this portfolio modeling, portfolio management stuff. And so we're like, it should really be married together, but no one till now wanted to do the unsexy services part.

And I actually think it's more than when you say $25K or $50K a year. That's a very— that's like you're getting a very good deal or you're a very, very small firm. I feel like once you get into any sort of institutional scale, I mean, you get into 6 figures that you're paying.

Well, I joke, I'm like, you know, you're paying 6 figures a year for a fund admin for their primary value to be, we didn't screw up your accounting this quarter. That's insane. And so I'm like, okay, let's add more value than that. And then you can get rid of all this bloat in terms of software that you're also paying for.

Accounting also drives me crazy. It's like, you legally have to do it. Like, you literally can go to jail. Maybe that's not as extreme. But like, I don't know, maybe you can literally go to jail for just not doing your accounting. And it's, you have to pay like a couple percentages of revenue as a small company, 1, 2, 3, 4% of revenue. Just goes to like paying somebody $30K, $40K a year to just like tell you some accrual-based account. Like, it doesn't even match up with your bank account if you're like a small business or a startup. It's insane.

Well, that's why I said I'm like— and tell any GP fund admin, their eyes glaze over.

Oh yeah. When you told me what you're doing, I was like— I think I just remember thinking like, oh my God, please no.

You're like, no, I don't want to think about this again. Uh, yeah, but that kind of leads to the next point, like You know, we can talk about this Copilot and all this like alpha. You know, if you're a billion-dollar fund and we add 1% value to you a year, that's $10 million a year. However, you need to get the blocking and tackling table stakes stuff right. And so we said trust is like the most important asset that we have, which is let's go get the best people from the legacy fund admins. Let's build the entire thing from scratch. Let's ensure that we're not taking on too many customers so we can serve people adequately on the services side. But at the end of the day, like, you need to trust us to do the basic boring stuff too.

So what did you do? You hired a couple fairly impressive hires out of the gate, like as a startup that's just getting up off the ground. How did you do that?

Yeah, so I'm, I would say I'm a dog with a bone. It's like from a sales perspective, it's like I have this thing where I think startup strategy is mostly overrated and it's kind of mostly stupid. People talk about whiteboarding and talking about all this strategy stuff. You know what actually wins? More volume. If you want more sales, send more cold emails, send more cold DMs. If you want to get more eyeballs on your stuff, write more content. And so for me, when I was like, we— here are the top 3 legacy fund admins, Gen 2 being kind of the primary one, only working with billion-dollar-plus private equity funds. I said, I am going to DM every single person who's ever worked for Gen 2 on LinkedIn, on Twitter. I'm going to call them, I'm going to email them, I'm going to carrier pigeon them. And so it's kind of like Volume solves most problems when it comes to recruiting. That's kind of what I was focused on, how we were able to land our kind of early key people.

How do you trust them to say, hey, I'm building a brand new fund admin from the ground up, from scratch, wherever you're at in that process? Like, how do you convince them to then make the jump?

What's funny is when you talk to like people that work at legacy fund admins, think about it as like Time Warner in 2000 when they got disrupted by the internet, right? Everyone there is like bureaucratic, stodgy old companies, 9-to-5 accountants. And every time everyone I talked to, they'd be like, oh my God, I keep talking about internally how we should build this tool and this tool and this tool. But the problem is, is they call engineering their IT. They don't even have engineers.

Oh no, that's not a good sign.

So they have like, you know, think about the best developers in the world. Are they ever going to join a legacy fund admin to go build the product to make this 10x better? No. And so my pitch to them is like, Hey guys, we have the cracked engineering team. Now we have the accounting experience and we have our kind of early batch of customers. Let's go win.

Interesting. So it's kind of like if you want to choose who to compete against, compete against someone who calls their engineering team the IT department. Yep.

Literally.

Fascinating. That's a good idea. How big is the market? Just curious, like fund admin. I don't know, like there's trillions of dollars in private market Assets that are being administrated, just like TAM perspective, how big is it?

Yeah. So right now there's about $8 trillion in private market assets across venture capital, private equity, private credit, and then you get into real estate and infrastructure funds. Then you think about the hedge funds of the world, which are like Citgo, SS&C, are some of the legacy players that primarily serve hedge funds. But my thesis is much bigger than just fund admin. I'm a huge fan of this idea, what Parker Conrad from Rippling calls a compound startup, which is There's this death of point solution SaaS where everyone built a super narrow thing. Just like Rippling focused on employee data as this underlying system of record, and then from that they could build IT device management, spend management, HR. For us, the way we think about it is your underlying accounting data with our multi-entity general ledger that we built is this core piece of like system of record data. And from that we can build 10 other products that have, you know, multi-billion dollar TAMs each.

Are you allowed to say what those are? Are you keeping those a little closer to the chest for now?

For next time.

No. That's fair. But so the product you just kind of announced, Fund Admin, and your first initial wave of customers, venture capital firms.

Right now we've signed $1 billion in assets under administration. We're really hyper-focused on serving $100 million plus AUM venture capital funds, given they typically have one plus finance team member who has to manage these existing fund admin relationships. And it's kind of been our sweet spot, but we're on a warpath to world domination. So we're going after private equity, private credit, and everything else in between soon.

Amazing. Rewinding a little bit though, I think we first kind of met on Twitter. Like, I don't actually remember when we actually first talked to each other, but you kind of got into this world through Twitter. Can you talk us through that?

I kind of— it was funny. It was like COVID hit. I was like a random college kid. I was this guy. So I went to Yale and I was this random maniac on a mission being like, okay, Now I want to run up some mountain, but I don't even know what this mountain is. And it was like, just like any other person who has no idea what they want to do with their life, they're like, let's get a job at Goldman Sachs. That sounds like a fancy mountain to run up. And so I like won the like Hunger Games of investment banking recruiting, got the job at Goldman, and then COVID hit and I was like in my parents' basement, like reading Paul Graham, Sam Altman essays. I'm from Philly originally and my dad sells insurance. And so I like Didn't even know what a startup was. And so I'm like a junior in college being like, wait, 5 crazy people in a room can go build a billion-dollar company? That's insane. And I was like, wait, okay, there's only 2 ways you can add value to a startup. One is either you write code, you build, or 2 is you sell or get distribution. And so I spent 50 hours learning to write Python to realize I was literally the worst engineer in the history of Earth. I would've been like, you know, you know a 10x engineer? I would've been like a 0.5x engineer.

You would've been the bottleneck.

I would have been the bottleneck.

You would have been one of the IT department employees.

Yeah, exactly. Exactly. So I was like, all right, I don't want to be in the IT department, so let's go learn how to sell. And so what I did is I was like, okay, I am a no-name college kid with no credibility, but it seems like all of these really smart people in tech are hanging out on this place called Twitter. And I was like, okay, however, if you go to my profile, why would anyone ever want to follow a no-name college kid? I was like an Amazon landing page that no one ever wanted to click. Right. And so what I did is I joined this like Yale Startup Club and I was like, hey guys, I have a new idea. I made this up. I'm the head of speakers and podcasts and I'm going to just cold email a bunch of big-time Yale founders and investors and say, hey, I have 200 people that want to hear us chat live. You want to come join us?

Was this in person or Zoom?

This was COVID. So I did like fireside chats live on Zoom and they were like, yeah, I guess so. And then I would get 200 people to show up. And so I ended up interviewing Emmett Shear, the CEO of Twitch. Kevin Ryan, who founded MongoDB, Michael Seibel, YC, and some other folks. And then I would turn all of that into Twitter threads. And so stuff like, I interviewed the guy who invented Amazon Prime, here's what I learned, would go crazy viral. And so I went from like 0 to 100,000 in 12 months or so. And then people kept reaching out being like, are you in tech? And I was like doing this at 1 in the morning on Friday nights at Goldman. And then I was like, maybe I should join tech.

Yeah, that's what it was like for me. where it was basically, you know, stay up past midnight every night. It was a process of eventually kind of getting in. I think I was less methodical about it as you were, 'cause for me, I really just always wanted to be an investor. I really never wanted to like start a startup. So for me, it was less of that. It was a little bit less structured in the sense of like, I'm just trying to meet people and there was no real time box around it. Yeah. But yes, 0 to 100K in less than a year. That's pretty good for people who don't— who are not on Twitter back in the heyday. I

mean, back in the good old days.

Yeah, the good old days. What, what are your biggest Twitter secrets? And I guess Twitter's changed a little bit, but for somebody listening, say, zero followers or whatever it's at, and they're like, I want to get into this, what would you say? Like shortcut someone, give them like a 1-2 minute, just like, here's a TL;DR.

I apprenticed for Sean Peering in college, who has My First Million podcast. And one of my main jobs was helping him do some of his early writing. And, you know, the first thing I did is I wrote a Twitter thread for him. We get on a call, and he was like, this is terrible. Oh, no! It was like, this is not good. And I was like, OK, what's wrong with this? And so basically, the trial by fire is the way to go viral is to basically elicit some sort of emotion. And so the first time Sean ever opens up a Google Doc to write a Twitter thread, he is writing one of 7 viral emotions. And one might be, Haha. One might be, oh my God, that's interesting. One might be anger. One might be something else. And so you basically reverse engineer the emotion that you want to create from the audience to actually get them to feel some sort of strong emotion that they want to share the thing. And so that's the first thing. The second is 80%, 90% of the value derives from the headline. And so I'll write 10 headlines. And actually a tip for the audience too, which might be useful is I basically have a special Claude artifact right now with 7 different headline kind of generation tools or documents from people like Dickie Bush and Nicholas Cole. You should check them out. Where they write, like, I'll feed that to Claude and then feed the body of work of like, here's 150 words that I wrote, spit out 10 headlines for me based on those words. And so that's super useful. And I'm obviously happy to send it to people after if they want to. So like, I focus 10 different variations on the headline, use the Claude artifact, think about the reverse engineering, the emotion I want to elicit. It's kind of the TL;DR.

So Claude artifacts, that is sort of like a stored state of learning or output style kind of that you can do?

Yeah. So I fed it a few different PDFs. And so I'll feed it a PDF version of Nicholas Cullen Dickey-Busch about how to write 7 different types of irresistible headlines, for example.

Oh, okay. So you'll basically give the AI something that A person trying to learn this stuff would read. It will learn and then you'll just be like, all right, start doing it based on what you read.

And they're usually not like amazing yet. We'll wait till, you know, Sonnet 4.5 or something like that. But it gives like, gets the creative juices flowing where like I can take a piece of one and a piece of other and then that ends up being a good headline.

Interesting. Okay. Yeah, we'll throw a link in the notes to the show. Just people want to try it out. I don't know. Is that something we can share?

Yeah, I can share it.

Okay. Cool. And then so you were interviewing all the founders at companies at the Yale fireside chat. What were some of the best interviews that you had? Biggest things you learned?

Michael Seibel is amazing. People probably know this. He's like, you know, leads or is one of the partners at Y Combinator. And one thing that he said that kind of blew my mind is I was like, what keeps you motivated building YC? They've been around for 20 years. And he's like, I'm obsessed with institution building. And kind of what that means is having something like institutions that we all know, Harvard, Yale, colleges, all this kind of stuff. Yeah. And what it requires is like not just a long-term focus of like, how are we going to hit our metric for the next year? But it's like, how can we set up ourselves for 100 years? And it's kind of something I think about even like in relationships. To me, it's like if I want to spend, you know, 20 minutes with someone, I should want to spend 20 years with them in terms of compounding. I think he kind of brought that. And then the other thing he talked about is like, All about building systems and habits and how he was like, look, I wanted to become a better investor. I wanted to lose weight, or I wanted to do these things. And instead of trying to be like, I need to have more willpower, he would be like, okay, I'm going to cut all junk food from my house and then have my workout clothes on when I go to bed the night before, and kind of build those types of things. And so he was pretty good.

So you force yourself into— you don't just think about the habit, you do the things that force you to be more likely to carry out the habit.

Yeah, it's almost like reduce— I kind of think about it in terms of friction. Like if you want to cut friction to stop a behavior, right? So like if you wanna eat less, you should increase friction, right? Which means that like, okay, I'm gonna have no junk food in my house, so I have to order DoorDash to actually be able to eat food, right? And so like—

I know.

So you wanna like increase your friction?

I don't know. I don't think you could decrease friction on DoorDash.

There we go. Well, OK, remove it from your phone. You know, have a brick. Shout out Brick or whatever that Instagram ad is where it's like, you know, you could lock your phone. Have you seen this?

No, I've not seen it.

Oh my God, they haven't targeted you yet. OK, so Brick. I hate— I feel like this is an ad for Brick right now. This is an ad for Brick.

Yep. This episode sponsored by Brick.

Do the ad read. Brick, if you want to sponsor me right now, I got you. No, basically. Brick. You, like, tap your phone to this, like, literally it's like a black block, and then automatically it locks all the apps from your phone until you tap the brick again. And so what I'll do is I'll tap the brick, I'll leave it in my apartment, I'll go to the office, and now I can't.

That's— so it's probably like an NFC thing?

Yeah.

Interesting. OK. And you preset— here's the 50 things that you're unlocked to. That's actually pretty cool. That's a cool concept.

I hate how we're reading an ad for right now.

By the way, we have a link for 20% off in the notes. I'm just kidding. So the so you mentioned something I've heard you talk about before: the ASS framework for how you basically build relationships with people. And I know we're going to get more into sales stuff because you hinted earlier that was maybe the one of the two avenues that you went. So what is the ASS framework?

Yeah, so attract, search, and strengthen. So I basically wrote this blog post. It was probably like 2021. 2022 where I was like, okay, I'm gonna spend all of my time, because I had a bunch of free time as a college senior, doing whatever I could to meet forces of nature. And so forces of nature, these people, if you read How to Be Successful by Sam Altman, he talks about this where he's like, you meet someone and you immediately know within 5 minutes that they kind of have that crazy, they have that maniac, they're gonna do something interesting. And so I was like, all I wanna do is meet forces of nature. If I were to do that, the way to not do that is like randomly try to go to like a networking coffee event at your college and like hope the person that seems cool talks to you. It's a horrible way to do that, by the way.

Yeah, the inverse of what you should probably do.

Yeah. So attract is like, you know, putting something out in the world for people that are like a magnet for them to be interested in what you're doing. And so that was part of the reason why I did the Twitter content, part of the reason why I had a newsletter, part of the reason why I wrote on LinkedIn. And so it's like That's like one pillar. Second is search. And so what I'll do is I'll go to someone, you know, if I'm like, hey, I think Turner's awesome, I'm gonna go to the people that you're following. I'm gonna search through all the people that you're following and be like, okay, out of these 5 people, it seems like I could have the most overlap or they could be most interesting or interested in what I'm doing. And then I would send them targeted DMs either with, here's a piece of content that I wrote specifically, 'cause it's like proof of work. I don't wanna get into crypto here, but proof of work on like, here's a piece of content I wrote. thought you would like it for XYZ. And so it's not just like, I want your time, it's like, I have an opinionated thought. And so that's kind of the second piece is DMing people you find interesting with proof of work. And then the third is strengthen. And I think there's this constant balance between do you want to have 1,000 relationships an inch deep or do you want to have 20 where they'll come to the hospital at 2 in the morning if you're sick? And so I've really tried to fight and balance and figure out and prioritize. But it's more about like, how can you build these relationships where maybe you don't need to talk to them every single day, but you're passing them interesting content, you're in a group chat with them, you're giving them something like in terms of value. And so that's kind of how I think about building from ground up.

And then you mentioned something that I kind of realized, man, that's such a good idea that I have not really done, but it's pretty easy where you kind of passively give updates and follow up with people. I know you mentioned you did that with the fireside chats Can you talk about that real quick? Do you still do that?

Yeah. So after I interviewed people, I basically what I did is I was like, okay, right now I like came into that interview, I had like 25 questions. I was like a hustler college kid. I was like, I need to make sure that this isn't some generic BS interview where people feel like they're getting no value and they're getting asked all the same questions. And so I would like overprepare and then I would interview someone like Kevin Ryan who founded MongoDB. And then every 6 months after, I would send him an email being like, Hey, Kevin, it's that crazy college kid again. Here are, like, 4 things I've done in the past 6 months, right? And just, like, every 6 months, set a calendar reminder for these people. Because at the end of the day, like, you don't want to be, like, randomly pinging people, can you please get on a call with me or do some sort of coffee chat? Yep. Like, people are busy. And so, just pinging value into the void is what I call it, of just, like, this is what I've been up to. Thought you would like this, this, and this. And keep it short and sweet. And from there, I've been able to develop awesome mentorships and relationships from that.

And this— you were doing all this while you were working at Goldman still? Is that— how?

Yeah.

Did you sleep? Did you not work? Like, were you the shittiest Goldman analyst ever?

I was pretty good. You could ask my old boss. 10 PM to 2 AM on, like, Friday nights. So I'd be doing this on weekends. I'd be doing this late night. The hours at Goldman were pretty intense, like 80, 90 hours a week, especially when rates were low. I was doing stuff related to debt. And so it was like debt was flowing freely, rates were low, a lot of deals were happening. And so I was busy, but it was also just like, how badly do you want it? I kind of think about this right now. It's like I will do literally whatever it takes to win. I will fly across the country to Utah for no reason just to like get in front of someone for an hour. How badly do you want it? And I knew this was going to compound for the future.

Yeah, I remember when you, right after I invested, you were hiring someone. I just remember you DM'd me about this person. You just flew down to meet him a couple minutes later. And I was like, whoa, you're going all in on this.

Well, I could tell that story briefly. Yeah. So I basically cold DM'd someone and I was like, hey, where are you right now? He's like, I'm in Greenville, South Carolina. I'm like, okay. So I literally call an Uber immediately. There was a flight that was 2 hours and 7 minutes. There was a car accident on the freeway. And so 2 hours later, I arrived 7 minutes before the flight takes off. And it's like one of those like Home Alone stories where you're like running through the airport.

Did you make it?

I made it. Yeah. I was like, you know, hopefully JFK or whatever the airport is isn't upset listening to this. But yeah, I ran through all sense of security and we got it done.

Wow, that's impressive. But also, so you quit Goldman on your birthday. What a birthday present. Why did you quit?

So I think people right now collect optionality too much when they should actually be removing optionality. And so what I mean by that is you go to a good fancy college and your parents pat you on the back, I went to Yale. Then you run up this mountain that we talked about earlier, which is get the consensus job at Goldman. And then what happens is when I knew that I wanted to go build a company, I could have stayed for 4 more years in cushy golden handcuffs and said, this is good, but I feel like they shouldn't take the risk.

Yeah, I feel like it gets progressively slowly easier in banking. Like, it's not easy, but like, it gets less shitty.

Totally.

So it's like, I made it through making more money every year. It's like less shitty, more money, harder to leave. Yeah.

The way I thought about it though, when I said I don't want to just quit Goldman to start a company, because at the end of the day, like I had never been in a startup. I think I'm naive to think that I could go from spreadsheet guy to, you know, CEO or like building a company. And so I met 50 startups. I was like a VC turner, but I had one bolt.

Yeah, I remember. I remember you telling me this story. Like, so what is the process of doing that? Like if I'm listening to this and I'm literally Goldman Sachs investment banking analyst, wanting into a startup or insert whatever person trying to pick a startup to pick, what would be the framework or the process that you would go through?

The first thing I thought is like, this company that I need to join needs to have at least 18 to 24 months of runway.

Why is that important if I don't know what that means?

So what that means is startups typically raise money and then they maybe have like 2 to 3 years of runway left. If you join a startup with 6 months of runway and they don't get their next fundraising round done, you are out of a job in 5 months. And so at the end of the day, I thought a lot about, okay, what's my worst-case scenario? The worst-case scenario is I get fired in 2 months because I'm bad at my job, but we might as well learn if I can't hack it in startups right now anyway. And so I said, okay, I'm going to join a company that had at least 18 to 24 months of runway and that would be in a decent financial position. That was thing one. The second thing was I wanted to join pre-20 employees. The reason why is I was like, okay, I think I want to start a company. I'm like pretty set on doing this, but obviously I want to get some experience first. If you join a company at like 40 or 50 or 100 employees, you are siloed into different departments. You have HR at that point, right? And when— as soon as you have like HR and all these different departments, you don't have the ability to have mobility if you are crushing it in a specific job. And so I joined Meow, which was a Series A fintech. We'd raised about $27 million. I joined as the 9th person. And so it was like, come in, IC salesperson, go figure it out. And I knew I would have like room to grow and win.

Yeah. So you were hired. So what did Meow do?

Yeah. So we were like Costco for financial services. And so think like competing with Mercury and Brex directly and JPMorgan Chase and some of those players. But the idea was we can offer more yield on your cash because we were like the low-margin Costco. Right. So we'd pass back more interest to the end customer. And so I joined when we had $25 million in assets and I left when we had $1.5 billion.

Okay. And you brought in a decent amount of those assets, right?

Yeah, it was funny. My first day on the job, I like come in and we could talk all about like how I think about like setting yourself up for like a good first week. I think that's pretty critical. But I came in, my CEO looked at me, Brandon, he was like, are you just like a spreadsheet guy? Are you going to be like a Goldman guy? Are you going to like get something done? And so I literally was like, I'm going to close $100 million in assets in my first 100 days on the job. Mind you, that is insane. I was like, I had never sold a single thing before. I had never done any of this kind of stuff. And so I ended up like pulling it off. But it was literally like this crazy, like forged in the fire of like figure it out or die.

How did you figure it out?

Okay, I have to— if you were listening to this right now and you're like, what is sales and how should I think about this? Go to Alex Hormozi's The Game podcast feed right now. And he has like a 4-hour deep dive on every single sales coaching thing that he's ever done. And so that's kind of piece one. But I basically learned like a few of these kind of principles, being able to pull it off. And the first one that's like kind of maybe not obvious is like idle time kills all deals. And so what I mean by that is, you know, if you get introduced to someone and you're like, hey, you know, can we schedule a call for like 7 days from now or 10 days from now or 15 days from now. Think about every single moment that you elongate the sales cycle as a chance that the deal will die. One story around this is there was a $25 million Series A company that was going to move $15 million over to Meow. And I had worked for months working with this finance team lead. I'd worked with their whole team. They literally— he emails me the day before being like, all right, we're ready to move over $15 million. And then I follow up the next day. Hey, we ready for the $15 million? Nothing. 2 days later, nothing. 7 days later, nothing. 25 days later, I get an email from his CEO saying, hey, John's not with us at the company anymore. We're putting this on hold indefinitely. And so the CEO fired the head of finance. And right when we were on the 1-yard line, the deal doesn't get done and they reevaluate and we never close the deal. Imagine if I was a little bit more persistent, a little bit faster, and didn't let idle time kill the deal. We would have had the money in the bank.

Wow. So I know you have a couple other ones. So like, what, what other things did you learn during those first 90 days at Meow?

Yeah, I think get off email ASAP. This might sound counterintuitive. Most like business communication happens on email or on Google Meet or something like that. However, like to build like real relationships with people and like at the end of the day, like you need to believe you are adding so much value that they are crazy not to do this. Right. If you don't believe that, you need to restart and figure out what the product is, honestly. And so what I would do is immediately try to go from email to text basis with anyone that I was— any prospect that I was talking to. And so that may be on the first call, might be on the second call. And then once you get into text, there can be a lot more informal communication around like, hey, my CEO's pushing back on this, this, and this. What do you think? Or can you send me an email with 5 bullet points to make this stronger in terms of case internally? So like, get off email ASAP is kind of the second thing. Happy to talk more if useful.

Yeah. So you get— email somebody, they respond, you get them on a call probably first. Is that usually the first step is like get them to talk on Zoom or talk on the phone?

Always get on a call. And I think actually a lot— we could talk about like the first few minutes of a call. I think like a lot of people screw this up. They like get on and guess what? Think about like the prospect that's buying the product does. They're like, oh, this is another sales guy. This is so annoying. He's going to try to like talk about the weather somewhere.

He's going to try to sell me Fund Admin.

Yeah, he's going to try to sell me not Fund Admin if you're a GP. But like you get on the call and like they immediately think this is just another BS sales call. And so I think about like disarming someone and creating credibility in the first 30 to 60 seconds. And so like tactically, You know, the first thing I would say is like, you know, they say— you say like, how's it going? They say something, and then I would like give an overly long answer. I'd be like, oh, you know, I'm recording this podcast with Turner, but, you know, he was at a Chick-fil-A or whatever in Detroit, Michigan, and this, this, and this happened. And immediately people are like, oh, this isn't a guy reviewing a script. This is a guy that's like more human in some way. And that gets people talking a little bit more than like the generic, how you doing? The second is creating credibility. You know, I would say stuff like, hey, you know, I'm the chief revenue officer at Meow. We raised $27 million, this, this, and this. We serve customers like this. People are like, oh, this isn't just like some random guy who cold-called me saying like, do you want more yield on your cash? Right? And so like the tandem of those 2 things builds rapport and trust in the first 5 minutes, which gives you the opportunity to win the deal.

And you maybe— we maybe actually skipped this, but I want to hit on this. You have a framework for sending email. So even before you get them on the call, I think it's— is it SSS? Is that the framework you use?

Yeah, SSS.

It's how you send a good email to somebody, a cold email.

Yeah, I'm obsessed with cold emails. I've probably sent like 10,000.

You're one of those people that's just always in my inbox. I'm like, do you use the AI tools?

No, I don't. I actually am pretty anti-AI tools right now. Really? Okay, that's— we could talk about that.

I get way too many. I think I've commented the last couple podcast episodes, like, I feel like I get like 50 a day and it's just like the worst garbage.

And it's like 7 paragraphs. So, okay, the framework framework, SSS, is short, specific, and spacing. And so short, it always has to be 5 lines or less, right? And so like, that's kind of the first thing. Second is it needs to be specific to the person in some way. And that doesn't mean, hey, I saw you went to University of Oklahoma. I went to university— like, that is so contrived and generic, right? What's more interesting, like, I got Mark Cuban to respond to an email asking him to go on my podcast a few years ago. And it was like, I talked about something very specific that he said on another podcast in like one line or less, and I would ask something related to that that I thought was more interesting, right? So it's like short and specific. The second is spacing. People, when they write copy on like Twitter or LinkedIn, you know, you might be wondering like why like a paragraph could only be one or two lines and they don't have these like massive blocks of text because it makes it easier to scan stuff. And so if you follow those 3 things, And then the bonus tip I'll give for people, this is something I shouldn't even be saying publicly. I can't believe I'm saying this, but lowercase subject line makes it stand out significantly. And so what I mean by that is if you have a lowercase subject line, it seems unique because every subject line they get in their inbox is uppercase. And so now they're like, wait, what's going on? And that's all you need.

Hmm. It seems a little bit less formal probably too. Like, does it— is there a risk of like, oh, he didn't capitalize, punctuation's off? This is like a— If they're angry,

I'm kind of happy about it because at least they're responding.

Okay, fair. Yeah, that's an interesting one. I guess it makes it seem less contrived, like less pre-planned, like it's literally like an off-the-cuff cold email. You didn't even have time to capitalize because it was so cold and so, you know, unscripted and unplanned.

Exactly. And it's all about like the idea of like, it doesn't feel like when your first 5 minutes of a sales call feels scripted. Same with the email. Like I'll lowercase like, hey Turner, like Lowercase h, lowercase t, comma.

Yeah, I don't know how I feel about the not capitalizing someone's name, but then there's some people like certain Twitter style where it's no no uppercase at all.

Well, that's the Sam Altman special, right?

That's like the Gen Z. Gen Z doesn't capitalize words, do they?

I I think here's the thing. I think Sam Altman did this, and then everyone who thought they were like design cool did this, and then as us non-cool people here who are talking about fund admin. Then when we started to follow suit.

That's fair. So what else did you learn at Meow? Because you were promoted to— I don't know, you joined as like IC salesperson. I don't know what your title was, but you were Chief Revenue Officer. That sounds pretty impressive. Yeah, it's a startup, so I guess like it's hard to know what all is going on. But what else did you learn throughout that whole journey?

Yeah, I had never managed anyone before, meaning I had a small team that I was leading by the time I left and it was like How do you run a one-on-one? And when I Googled how to run a one-on-one or ChatGPT did, the advice was horrible. It was like useless stuff. So what I did is I ended up running this thing called a 3-2-1. I think I made it up, but it's basically like 3 things in terms of metrics from the previous week. So every one-on-one would start with like they would submit this 3-2-1 Google Doc like the day before that we would meet. And so 3 things would be metrics to, you know, number 2 would be like improvements that they felt in their own performance of things they could do differently. And then one idea to help get us to a billion in assets because at Meow we were trying to go for a billion. And so that structure kept things like very succinct and then we could spend like, you know, 15, 20 minutes on other things that they thought were useful. I had to figure out that. The second thing is like I just had no experience in like anything product related. And the beauty of having like a small team, Brandon and Bryce, the co-founders, are both really good at product, have engineering backgrounds. And it was like, okay, I'm the one who talks to customers every single day. I have these ideas around like things that they say and things that we can improve. How do we translate that in terms of working with like, you know, our killer engineering team on like products that people actually want? And so I think managing people, learning how to get the best out of people and the product stuff is all useful.

How do you do that? You take customer feedback and relate it into, you know, product insights and roadmap and all that stuff.

Yeah. So we ship this thing called a venture debt marketplace, which is basically like, hey, you know, you're a startup, you want non-dilutive capital, meaning you want $20 million that you don't have to give up equity for. That's usually based, you know, debt is typically someone with like their breakeven or cash flow positive. But a lot of people in venture do that around like attached to their latest financing round. SVB used to do this a lot, but there's a lot of these private lenders. And so I was like, I'm going to go hustle to get 30 different lenders to join this marketplace. But how do we build out like the system to like analyze a startup's cash flows, their accounting data, all of this stuff, and take that into like a here's a one-page tear sheet for a venture debt lender to make that useful. And so like I teamed up with a few of our engineers being like, here's the way I think it could work. What do you guys think? And then like learn the most important question as someone who's non-technical is like, how long do we think this will take and what is the level of difficulty? Because I think the biggest barometer, at least in what we're building at Hanover, is like, you know, my co-founder's an engineer and like talking to him daily on like how long do these things take and what do we think is really important to someone non-technical to like benchmark on what hard is, what easy is, what's simple and what's fast. And then you can think about like, Okay, after you ask that question 200 times, you have a really good sense of like, you know, time taken to ship different things.

So one thing in terms of time, work-life balance. So Brandon, the CEO at Meow, he said you would basically be in the office from like 6:00 AM to 11:00 PM. I've heard people say don't burn the candle on both ends. Like I've done early or late. I also have kids. So like family and kids, it's like a little bit different. That's, so maybe it's working when you're, you know, with your kids at I don't know if it counts the same, but like, how do you do that? Like work-life balance? How do you think about that?

I'll say this, work-life balance in your 20s is the easiest way to guarantee a mediocre career. And what I mean by that is like, at the end of the day, you take venture capital, you are signing a term sheet to join the Olympics of business and to go after building a $10 billion plus company. If you want work-life balance, don't take the money from and don't raise venture. That's almost like, to me, it's delusional of like, do you think you're going to win an Olympic gold medal working half as much as everyone else? That would sound crazy if you told an athlete that. But we think in business that it's okay to work 40 hours a week if you want to go build a $10 billion company. And so I think like you just need to figure out what your priorities are. For me, I think there's this like false dichotomy of work-life balance and like Hating your life, working really hard. Those are not like that. I actually, I mean, we're playing Avicii at 8 o'clock in the office. We're banging a gong that we play when we ship something useful. You know, people are coming into the office yelling excited in the morning. When you're, you know, what I call a few crazy people on a mission to go take over the world, it's fun. It's intoxicating. It's much more fun than 9 to 5 and watching Netflix and eating ice cream at 8 PM every night.

Yeah, sitting in meetings where you plan out what the next meeting about planning meetings will look like.

Yep, exactly.

Yeah. So then you got promoted pretty quickly though. I guess that happens sometimes at a startup. Usually you have to be pretty good at what you do. What was your kind of playbook and the reason that you think you kind of got so much responsibility and were able to just kind of get the trust of Brandon so quickly?

Everything is about earning. It's kind of like the cliché of first impressions are everything, but I think people don't take it seriously enough when they start a new job. They're like, oh, you know, I can spend the first few weeks like getting my like random laptop configuration settings. That's the worst mindset of all time. What I did is I said, okay, I've never worked in sales before. How could I figure out a way to close $100 million in my first 100 days in terms of assets? And so the first thing I did before day one of joining Meow, I had sent hundreds of cold DMs on Twitter and LinkedIn to people I know setting up. I think I set up like 15 or 20 meetings. my first week before I joined in terms of potential prospects.

You're saying you had them lined up for that first week?

For that first week. Okay. And so, like, usually a salesperson takes a week or two to start building a pipeline. They get meetings set up in like week 3 or 4. I was like, I'm crazy. I will set up 20 meetings in week 1 of potential qualified prospects. So that was like super serious. I'm going to go figure this out and it doesn't matter.

So you've got these like IT onboarding people like, all right, we're going to get you set up with your laptop. You're like, nope, sorry, I got 3 sales meetings right now. Today.

Like day one. And so that was kind of the first thing to set the tone. The second thing is like become obsessive about the product that you're going to be selling. And so I think like, you know, I remember like a few weeks before I joined, it was me, Brandon, Bryce, and Cyrus, and I went into Brandon's apartment and just spent 3 hours with them obsessing over the product. What is the product? What's the positioning? What are the obstacles? What are typically people complaining about? What's happening? How do we think about handling these obstacles? And I just like sponged 10 pages of notes. And so I came in day one with a good understanding of the product and how to think about demoing it. You know, 15 to 20 meetings set up. And then, you know, I'd say the last thing is, and I can't believe more people don't do this, which is send your CEO weekly updates on what you did this week. I can't believe more people don't do this, right? So like, you know, my first month or two, I wasn't reporting directly to our CEO. And so what I did is I would say I would send an email with a Google Doc with him, to him and Bryce and say, Okay, here are the 7 bullet points of things I did. Active deals in the pipeline, you know, the number of outbound that I did, all these kind of things that just proves one is like you're thinking about this and tracking this and 2, you're hustling and getting things done. And so I think like combo of those 3 things are like the right way to kind of get your, get your feet set.

I feel like you've said one other thing too, is like do more than what your job actually is. How did you do that?

Yeah. So like the beauty of joining like a— and I should actually say this, Chief of staff is the dumbest job title of all time.

Oh no, chief of staffs are in turmoil right

now. So basically, like, I think the common trope is like if you're a banker or consultant and you're non-technical, you should join a startup as a chief of staff and you should like, you know, do this strategic work and then you should like, you know, switch the PowerPoint colors for your CEO ahead of the board meeting. What that does is back to the original point of you're either building or you're selling, you're writing code, you're convincing people to buy your product. You're at— you're building no discernible skills in terms of, like, tactical, what can I do to move the business forward? And so at the end of the day, I was like, not going to do chief of staff BS. I'm going to join as, like, an individual contributor on a skill, which is, like, unsexy being a salesperson, which I don't even know why people think that's unsexy, but it seems less strategic. And then over time, I was able to be like, I am crushing so much. Here is the input that I've earned on other things. Like, hey, we should ship these— this other product. Here's all the data that I have to back it up. So that's kind of how I think about like expanding your scope of responsibility after you kind of prove with your first impression.

So do you kind of think about it as an ownership mentality almost? Just around like, I mean, what's the second order effect of like, I got some feedback, what should we do with it? Or what's like a business objective goal, whether it's Getting more revenue or, you know, improving throughput, removing a bottleneck. I don't know. I'm trying to make it as dumbed down, not corporate jargon as we can, but it's like, how do you actually move the needle?

So Keith Rabois has a great framework for this. He calls it barrels versus ammunition.

Oh, yeah.

And so barrels are people that like you can just give them a task. You can be like, hey, go launch a venture debt marketplace and get $1 billion in demand. That is 1,000 steps to do that. But a barrel can assemble the team, figure out what to do, break it down into manageable pieces, attack, execute. execute and then come back and say, this is what's been done. Ammunition is typically like, hey, could you please send 1,000 emails a week, cold emails, to book X number of meetings, right? They are performing at the level that's necessary to like keep a job and perform at like the right kind of level. But your organization basically scales a function of the number of barrels you have. And so I kind of think about it as like, what would a barrel do? And then go do it.

That's such a crazy. I've never gotten that barrel thing. Yeah. Do you know why it's called a barrel? Like, why did he call it that?

I think it's guns versus ammunition, like a gun barrel. Like you're shooting the ammunition.

Fair. Yeah. Yeah. Okay. Interesting. Because I think the first time I heard about it, I thought it was like barrels of oil. I'm like, it's such a weird analogy, but I guess I could see that barrels versus ammunition. Okay. So then you left me out to start a company. How did you know it was time to leave?

Yeah, so I'm still super close with Brandon and Bryce and the Meow team, and they're crushing it right now. So it was definitely a very difficult decision to leave. However, like, I just had this itch where I knew, like, okay, if I can deliver at an early-stage startup joining as like the 9th person, like, I always knew that like it was the vision to like go build my own. And so Tough decision going from like quitting big, you know, Goldman place to join a startup no one's heard of and then quitting startup to like be in my bedroom to go like figure out a fundraise and get things done.

Big step down.

It was, it was a big step down. But yeah, I don't know. I'm kind of like, you know, will I look back when I'm 80 years old wishing I took the leap? I knew I would. And so I needed to do it.

Yeah, I think there's something— it's kind of tying back to what you talked about with like the chief of staff or the title thing. It can sometimes be a little bit humiliating almost where I'm just like, if you look at your resume, you went to Yale, then you worked at Goldman. That's kind of like the perfect path of somebody going through that. They're like, you, you did it, but then you like, it's most people would think you took a step down. Like, and I think it's interesting, like the, you made a comment about engineering versus sales. For like strategy, chief of staff. I feel like a lot of people, it's underrated or not even appreciated enough of just like being a salesperson, like an entry-level BDR or whatever. Like sales is such a hard and it's hard to get good at, but such an underrated skill. But it's like, I don't think it's that big of a deal to like take that, just take a job like that.

I've been blown away by like how many people turn their nose up about like 2 things that I think are incredibly underrated in startups. One is sales, which you talked about. The second is copywriting. So if you guys know Harry Dry from— if you go to marketingexamples.com, he has this incredible site where he basically like takes a bunch of examples of really good copy, meaning like think about that as just sales that happens on a website or on an ad or on, you know, getting someone to click something or buy something. That skill no one talks about. And so like when I think about writing our landing page, I'm not thinking about boring fund admin white glove jargon, jargon, jargon, right? I'm thinking about in 1980 there were 50 venture funds. Today there's 40,000. It's 800 times more competitive and you're still stuck in the Stone Age.

Yeah.

That you can learn from people like Harry Dry and like writing on Twitter and writing on the internet. And I think like those 2 skills everyone thinks are like dumb or don't— aren't that valuable. And I think that's where the alpha is.

It is kind of like removing buzzwords almost. Like when I think about Uber, you could describe it back in 2010 as like a cloud-based, decentralized, like, right? Or it's just like get anywhere with your phone. Yeah, it's like you can get so much crisp by just, I don't know, thinking about the copy and kind of cutting through the noise. So you— so you getting back to the Meow The transition from Yao Tan over, how— what was the process like? You raised a little bit of money. Can you talk us through that?

Yeah. So the fundraise raised $2.5 million originally. I kind of think about this idea when it came to like the idea maze. I think about this idea of like founder market fit. And so, you know, for me it was I have worked in finance before. I understand finance, you know, intimately. I know what a balance sheet is. I know what an income statement is. So it was like kind of the first piece. The second thing, it was like, okay, I have this thing where I like took probably 1,000 calls over 15 months learning how to like sell B2B. And so it was like, you know, that was— I knew like something in like B2B finance was like where I needed to go. And the second thing is like my co-founder, he was a Columbia guy, graduated 2019. He was an Oscar Health backend engineer for 2 years and a YC co-founder CTO for 2 years. unsexy backend data-related stuff with a ton of complexity, like building a multi-entity general ledger married to like B2B finance, something related to that. And so like I kind of was like, okay, what do we have an unfair advantage to win in the Olympics of business, which I kind of talked about earlier? Let's stack our odds a little bit.

How many different ideas did you kind of think about before you finally settled on like fund admin is the exact problem that we want to try to solve?

Yeah. So it's funny, like I have a 40-page Google Doc which I will never share, guys, publicly. With basically everything I've learned about this fund administration space more broadly. Who are the major players? What are their weaknesses? What are the tech builds? How do we think about building a multi-entity general ledger? What advantages does that give us? What are the current— like, what do customers complain about? How do they think about this? And so like, for me, it was like, if you're going to make a 10-year decision on something, I'm going to be in this for hopefully 50 years, honestly, is like, let's get all of the data from the current providers and current players. And then it was really just a matter of like, Founder market fit versus like what I think is a big opportunity, which is this idea of like AI-powered services. But yeah, we cycled through a bunch of different ideas, you know, anywhere from like think about us as crazy people at, you know, 1 in the morning writing on whiteboards being like, is this it? And then we landed on this and kind of built conviction from there.

So you talk about multi-entity general ledger. What does that mean? Yeah,

that's a lot of jargon. A general— back to this idea of like Rippling, their kind of core system of record is employee data. And so you have employee data that allows you to do like IT device management, HR, spend management, all this kind of stuff. For us, it was like our system of record is a general ledger. A general ledger is just a fancy way to think about taking transactions and turning it into the language of accounting. And so it's almost like translating Japanese to English, right, for accounting. And so when you build a general ledger, like a common example would be like QuickBooks is a general ledger. The problem with, you know, venture capital and private equity is multiple different entities that are all interconnected. And so—

So this is a management company and a fund. A

management company, a fund, a general partnership entity. They might have parallel funds, they might have different structures, they might have SPVs with unique structures, they might have like all of this like complexity regards like the interplay between all these things. And so we said, do we want to try to use an existing general ledger? Do we want to call their API? Do we want to try something? And we kind of came to the conclusion and we had the team to do it. We were like, We need to build this thing from scratch. And so we did. That's what we did.

Are there not people that do general ledger APIs that are out there?

Yeah, it wasn't flexible enough, honestly. When we thought about like specific to venture capital or private equity, what we realized, you'd end up like wrestling the data from like our customer into the API and it just wouldn't be accessible. Like Xero, for example, doesn't allow you to update valuations for on a quarterly basis. And so it was like, Let's, let's build it from scratch.

So what does this unlock? Like if I have your general ledger versus not using Handover, like what do I get out of all this?

No one really cares about the GL. Like it's, it's fancy technology, but like literally no one cares. It's back to this idea of like the GP doesn't care if I say, hey, it's going to be slightly better accounting right now.

They're like, just remove the accounting.

They're like, I don't want to think about it. They're like, I don't want to think about this. So Really, the unlock is if you look at like a legacy player, they have like some random general ledger that they're using, then they have Excel, then they have Bill.com, then they have some random system on top of Salesforce that they built to like call capital, and they glue it all together to like get you your waterfall calculation, do your financial reporting. Now, none of that matters except for think about all of where that data is trapped and siloed across 7 different systems. You have no ability to get insights in a simple like ChatGPT Copilot style to say like, what's our IRR by this specific investor at the firm, right? Or like, what are our top desktop portfolio companies pulling in like the context from someone's inbox with like their company updates and the board decks and like all that kind of stuff and then matching it to the underlying general ledger. And so the GL doesn't matter. It's kind of like turning that fund admin cost into like an advantage for your fund. It's kind of the vision.

Interesting. What do you, what are you seeing as like the early customers that are starting to use it? What's like a characteristic of a firm that's just, that seems to be a good, good early adopter?

Yeah, $100 million plus AUM venture capital fund, typically less than that. You might not have enough data because you might be only like one fund in with like a $10 or $20 million fund or you don't have any finance team members. And so those kind of things of like, okay, we have this like 3-person finance team that's like spending a ton of time every single week, you know, wrestling from the fund admin into your $100K a year SaaS tool. So like those have kind of been the perfect early adopters.

I know you have this thing, you say that B2B SaaS is dead. That's a crazy— I mean, I think there's been some people that have said that, but that's a pretty bold statement. What do you mean by that exactly?

So I think like the social network comes out. Everyone wants to be Mark Zuckerberg. There's a flood of CS degrees. Then there's a flood of AI tools basically making it easier and easier to code. That means there is in every single SaaS category, there is 100 times more competition. If you want to build an AI SDR, which is like a common SaaS category now, there are 50 of them because they're all using OpenAI's API, Sana 3.5, whatever, like off-the-shelf kind of like Next.js, whatever frameworks they're using. And so it's like, okay, there's 100 times more competition and there's less differentiation, meaning like the willingness to buy for software is going off a cliff. You see Klarna is already ripping out Salesforce and Workday for a massive company. And so what that means is like, what does AI enable you to do? You don't want to compete with tech companies. You can actually sell the work itself and actually sell, like compete against services companies, which is what we're doing. Which is like, okay, SaaS is dead. Not that product is not valuable and great engineering and great product and craftsmanship is always incredibly valuable, right? And we have a great engineering team, but AI is unlocking not just building a slightly more efficient piece of software. It's like no one wants to deal with the accounting. They don't want an accounting tool. And so that's kind of this idea of like, you know, instead of building a tool to sell to Goldman Sachs, you should just build the next Goldman Sachs. Right. And that's kind of the framework I think about.

So the first couple of customers that you've kind of signed that you're working with, what do they like about it? Like, what's the reason that they switched? Because I'm assuming they're— if they've got over $100 million in assets, they probably have a couple of funds, 3, 4, 5, 6. They got to switch everything over. There's all this, I don't know, organizational debt, institutional debt, whatever. How do you convince people? Why do they switch?

Yeah, I'm obsessed with this idea of one-click migration, one-minute time to value. And so if you are in this space, you literally might be like, that is one of the most absurd things I've ever heard. What that means is typically, say you have a billion-dollar venture fund with 5 different funds to migrate to a new fund admin, it takes 3 to 6 months. They charge you $100,000. Yeah, that's like implementation fees. Yeah, it's terrible. And so like my whole thing is, can we build a bunch of stuff around like AI document extraction, all these kind of different things that we've built to enable someone to literally click one button and port over all of their data for the past 10 years. That is not easy. So that's kind of like part of it.

Yeah, it sounds not possible.

It's possible. Okay. So it's like one-click migration and then the 1-minute time to value. Back to what I was talking about earlier, like the primary value of a legacy fund admin is they didn't screw up our accounting this quarter. And so it's like you're competing with that. And so it's like, okay, Can I provably say with this Copilot pulling in context on the portfolio modeling, the portfolio management side, I can give you a 1% advantage on $1 billion? That's $10 million a year. And so it's kind of like, can you trust us to execute? We brought in the world-class team. Can you not have a pain in the ass to migrate? One-click migration. And then can we drive value for you right away on day one? And so I think that's kind of like the magic formula to get people to want to do this.

Yeah, I think for context, people, I'm in a bunch of group chats with other VCs. Literally half the stuff people talk about, it's just complaining about their fund admin. So it's a pretty big problem. I don't know if we, if we specifically hit on that yet, but yeah, it's, it's, it's usually not people's favorite thing. It's kind of, it's sort of like doing your taxes or maybe like going to the DMV. But if you had to go to the DMV and like renew your license every week and you couldn't, you couldn't get in line ahead of time, like, you know, skip to like, you have to literally walk in. Wait for an hour sitting there. Like, it's, it's a very— it's usually there's like an emotional reaction of like interfacing with your fund admin. On average, that's how most VCs feel about it.

And, you know, I'll, I'll say this right now, this is going to sound crazy, but, um, most people talk about white glove service. I think it's like as bad as the word synergy because it's literally like—

That's usually the pitch. The pitch is like, we give white glove.

And I hate it. No, why I hate it is because it's jargon-filled useless information that no one resonates with. And so, what I changed it to is I say, 12-hour SLA or you don't pay. Now—

12-hour SLA?

Now, what that means is if I— if we take longer than 12 hours to respond to you, you don't pay us for the quarter.

For the quarter? Wow.

That's insane. It's called radical responsiveness. But I'm literally like, put your money where your mouth is. No one else wants to do it. By the way. And so can you— it's like trust but verify. You could verify this.

Going back a little bit on the fundraising side of things, you kind of had it. It sounds like you sort of had a round raised, kind of had a deal lined up, and you decided to not go through with it. What happened there and why did you do that?

Yeah, people called me crazy. So I had this idea of like always get on the plane. And so the story behind this is that, you know, it was Friday night. I was final round with a venture fund. And, you know, I get connected with one like the GP who was going to make the final decision. And, you know, I say to him, I was like, hey, I'm going to be in SF this weekend. It was like a holiday weekend. Do you— you around to meet in person instead? He responds 24 hours later. So it's 8 p.m. on a Saturday night. I'm sitting in New York City and he says, yeah, do you want to just like drop by the office tomorrow at 10 a.m.? I booked the red-eye flight. I fly overnight from New York to SF. I call an Uber from the airport. I show up to their office at 9:45 a.m. for a 10 a.m. after like 8 hours of travel straight, 2 hours later, ended up getting the offer from that fund. I think they're great. For me, it was really just like, I am hyperfocused on, you know, one thing around aligning myself with someone that I want to spend the next 20 years with, and people that feel the same way about your relationship between founder and investors, whether it be hands-on, hands-off, all that kind of stuff. And so it was like, the cap table is an irreversible decision. And for me it was like, I want to be in the, you know, I want to have the right people around the table that want to build the same way I do for the next 20 years. And so ended up not taking it.

But— You had no fallback plan.

No fallback.

I think I was in at that point. Like, I think I told you, like, I'm in.

Yeah,

I think it was like pending. It was— I was like pending valuation as long as it's reasonable because I've had that before. I've told founders I'm in and it ends up being like an insane priced round and I probably shouldn't do it for portfolio construction purposes. Yeah. So why did you, like, how did you kind of move past that? You just basically no plan?

No plan. I mean, look, it was like an auction process where I was meeting, you know, 30 or 40 investors in the span of 3 weeks or so, 4 weeks, and ended up working out with Souza, who led the round. And Chad and Pratish have been incredible. Yeah, they're people I want to compound with and go build something massive over the next 20 years. But yeah, it was a moment where like people around me were like, you're a lunatic. And I was like, You just realized this now?

That's fair, yeah. Speaking of Pratish, he said, I gotta ask you about Chipotle and Sweetgreen maxing. What's going on there? We were just talking about Sweetgreen earlier.

This is the least tactical thing of this interview, so you can skip over. No, I'm kidding. Basically, when I graduated college, my parents were like, hey, like, what do you want for your grad present? You know, most people get like a watch or like something like this.

And I was like, Are you really gonna say this?

I was like, wait, um, yeah, I don't, I don't want anything. I'm good. I don't really like watches. And my mom was like, all right, here's your grad present. And it was free Chipotle for a year. And so I spent probably $4,000 in Chipotle. I was DoorDashing it. I was eating it 3 meals a day. I was doing some crazy stuff. And, uh, you know, that was, that was it. And I told, I told, I told the CEO of Sweetgreen, if he's listening to this, I DM'd him. I was like, I only love 4 products in this world: Chipotle, Sweetgreen, HubSpot, and Eight Sleep. Shout out Matteo. And so it was, you know, I was like, okay, those are the only 4 things I want, so I'm good with that.

Wow. Yeah. Jonathan, the CEO of Sweetgreen, was the first episode of the podcast, actually.

Let's go.

So we'll, we'll throw a link to that too if people want to listen to that one. That was actually a good one. I think I did pretty good for those. The first one. It was— I've definitely gotten better since then. You know, you learn, you learn as you go. So very first customer you ever got, first one to sign, how'd you get them?

So back to this always get on a plane idea. So I literally am at the point where I'm like, if you haven't noticed this by this time in the interview, it's do whatever it takes to win. And so for me, it was like, I'm going to fly to San Francisco. I am not going to leave this office until we get this done. Now, they were already, you know, hey, we're thinking about doing this. It's not like I was Literally just like camped in.

Yeah, one of those climate activists just like chains himself to like the picture or whatever.

Yeah, so I wasn't chained that closely to the desk, but, you know, I was just like, I'm not leaving San Francisco until we get this deal signed. And I think like the broader point is like, if you do whatever it takes to win, hopefully it surprises you in the positive direction. And so, you know, I stayed there. I was doing like Hotel Tonight, you know, booking, booking at like 9 p.m., be like, okay, we're doing another day. And I'd like book a hotel for the night. The next night. And so, you know, I just think it's like staying around the hoop, kind of doing whatever it takes. And, you know, got our kind of first, first deal signed. But, you know, hopefully that'll lead to many more.

So how do you not be annoying in those kind of situations when you're trying to be persistent in a, in a selling context, but not like if you just annoy people to the extent of it's like, get away from me?

Totally. So I call it like polite persistence. A customer that I used to have at Meow talked about it. She's like, I can't believe like you, you bother me a lot. And I don't I don't say this lightly, but it's actually kind of useful. Like, you'll send me stuff that's not really super annoying. And so what I do tactically is like, no one wants to be harassed by the sales guy over email every 3 days for 2 straight months, right? One time I followed up 27 times with someone. They wired us $25 million, which could be a separate story. But it's literally like, what it is, is how do you have like a multitude of different touches, meaning different touchpoints for the customer? That makes it not annoying. And so one might be, hey, you know, following up over email, and then you go like all of their LinkedIn posts, and then you send them a LinkedIn DM with an article to something they might find interesting. Or like, you basically like vary up the touchpoints. Then you send them a text, then you call them. Like, you can vary it up in a way where it doesn't feel like you just followed up on an email chain 27 times.

Yeah, I've gotten that before where it's literally the same 8 emails in a row, just checking in to see if you saw this, in case you missed the last 8 emails.

Yeah, don't ever say friendly follow-up for like 20 in a row. Yeah. So varying up the touchpoints and that kind of stuff is usually helpful.

So that's when it comes back to earlier when we talked about just get their phone number or get off of email or different channel. That way you can, I mean, you can, a LinkedIn like or a comment on their post or Twitter or texting them something. Or email. Like, that's, I think, 5 or 6 different channels where it didn't feel like it was just email over and over and over and over again.

Yeah, it's just like multi-touch. And like, at the end of the day, I think like people feel genuinely, if you are like super excited about the product and you have such conviction that you will add value, that's like rule number one before you even learn like tactical stuff. People can tell if you're like, hey, I want to like do this to get a quota to like get some whatever for some startup that I don't really care about. That's obvious. And so I think like you need to start with the conviction piece and then go to like, okay, how can I like politely follow up with someone? Because I'm giving them— it's like, if you believe you're selling water to someone in the desert, why would you not follow up?

Fair. Wow. That's a good— it's a pretty good sales pitch. It's kind of impossible to say no to that.

Well, if they believe it's water in the desert.

Yeah. So you just said, separate story, 27 times following up. With someone. What is that story? Yeah, that's a good one. I don't know if we want to get into this.

Yeah, we can get into it. So, so I kind of was at this point where I'm like, okay, I will just like keep following up with someone. Now, this was 27 times across 3 different months and they— it was a text, it was an email, it was a cold call, it was a voicemail, it was a LinkedIn DM.

So when you do this, are you like, hey, I'm just talking about meow or like, like, what's the—

So here's a tactical thing. So one could be like, like, here is, you know, an update on where the yield curve is specific to meow in terms of like, here are where treasury bills are priced at this point. Wanted to let you know for this, this, and this because of this, of what we talked about. And so it's like add value with something that they probably wouldn't know the information about right now. And they are a head of finance at a company. And so like they'd find this useful for them. And so like those types of touchpoints, it was like that. But then like after a certain point, it was a lot of, uh, you know, friendly follow-up. And I almost gave up like 2 or 3 times because like after time 20, like I should get the hint, right? But what was crazy is they ended up wiring us $25 million for Meow to buy our like, you know, treasury bill or banking product. And they were literally like, wait, I'm so glad you were following up because like, you know, it was like a to-do list for me. I'm like, call me a human to-do list. I got this. And so it ended up being kind of the right fit. But I think like you never know until they say just like, stop reaching out. This is a bad fit. I think you keep going.

This one thing you have, you have a philosophy of the best companies are cults. Can you explain that?

Yeah, I think every great company is a cult. And so, the way I think about it is like, you start off with a few crazy people in a room with like a vision or a secret about the world that other people don't know yet. And so, I think like to do that, to separate yourself from like 9-to-5 people that just like cash a paycheck and don't really care about each other. What are the things that you can do to build closer ties among the team to when the going gets tough, people want to push? And so the first thing we do is I hate remote work. I think remote work is an easy way to guarantee failure. And the reason why is because if you see someone once a quarter, how much are you going to trust and care about that teammate to deliver for them or respond to them or be like, have an actual relationship with them if you see them once a quarter, right? And so it was like remote work. And even I'll go a step further, WeWork, we avoid WeWork. And the reason why is like you're surrounded by a bunch of mediocre companies that work 9 to 5 that don't really care about what they're doing. I don't wanna be poisoned by the people you surround yourself with. It's just like you become the average of the 5 people you surround yourself with. I feel the same way about avoiding WeWork and avoiding remote work. And so, you know, the first thing was like get our own space where we can set the tone and set the culture. of what we do. So it's kind of like the first piece.

You talked about gongs and Avicii.

Yeah, gongs and Avicii playing. We got the whole— and if you want to join, I'm hiring a founding engineer. So

there you

go. Plug.

You do daily team dinners?

Yeah. So usually at 5:00 every day. So this is going to go— Chipotle is really tying this episode together.

Also, quick note, this episode is sponsored by Chipotle. Link for 20% off.

Oh my God. So, okay, so usually we have Chipotle every day at 5:00 PM. And then we work for another, you know, 3, 4 hours after. So it's kind of just like, it's a good way to like have 30 minutes as a team to just like talk about stuff outside of work and just like see what's going on in their life. And I think like we are like Navy— I joke we're like Navy SEALs, like very intense culture. Everyone's moving really fast during the day. Things are, you know, bolts are flying around. But like this is a good opportunity to like, you know, build relationships with the team outside of, you know, traditional kind of work. And so we focus on that stuff.

And then your favorite founder of all time, who is that and tell me about him?

This is a tough one, but I'm going to have to go with John D. Rockefeller, but for the reason why people don't think. And so Rockefeller, one of his calling cards, obviously built this massive oil tycoon, but he talks about this idea of vertical integration. And so what that means is if you are creating oil, you can create all of these other components that you need. And typically you would partner with people and say like, hey, I need wood for my like barrel of oil. I'm going to like contract that out to a lumberyard. What I love so much about him is in his obsession and quest for vertical integration, he said, no, I'm not going to work with a lumberyard. I'm going to plant a forest right next to the factory and I'm going to get my own wood and I'm going to source my wood. I'm going to make the barrels myself and I'm going to vertically integrate. And I think about that a lot when we make like product decisions today of like, what is the Rockefeller path of vertical integration? What— and what that means, instead of outsourcing our general ledger, we built it ourselves. That gives us flexibility to build better and different products on top. And so yeah, that's kind of why I love them.

So what other things besides general ledger, like how else do you think about when do you build internally versus when you use someone else's product and, you know, go vertical?

Yeah, I would say like a lot of it comes around to like thinking about how data flows and thinking about what you can do with that. And so if you guys want to check out Meter, meter.com has a pretty cool demo of their generative UI for what they do, which is internet infrastructure related stuff. And their whole thing was automatically on the fly based on a prompt, you can create graphs and tables and a lot of that stuff, which is kind of what we're focused on, but it's different in terms of the underlying data is accounting data, portfolio company data, all this kind of stuff. And so the way I think about it is like, if it's going to be as difficult to build what I'll call like the bridge between someone's API transforming that data for our use case, then we should just build it ourselves. And my co-founder CTO thinks a lot about this of like, we have so much more flexibility if you have the right engineering team, which is the key of like, you know, great engineers are like jet fuel for product. And so it's like, if you have the right engineering team, And it's critical to your system, build.

So you talked about you have a team of cracked engineers. How do you tell if an engineer is cracked or not? And then how do you hire good engineers?

I wish— I want to get way better at this, I'll be honest. I— so my co-founder, CTO, we do like— so the way we run the process typically is I'll screen someone for 20 to 30 minutes based on culture. And so what that means is like, do they want to work 9 to 5 at a big tech company with free snacks? probably not the right fit, right? If they really care about like, hey, this is a team of Navy SEALs, we're going after this massive vision, we have traction, this is like the most de-risked company in seed. Okay. And you want to join an in-person, only intense culture in New York who has a lot of fun, like that's the right fit. And so like I'll screen people out with a series of questions.

So people usually do the culture fit at the end. You're doing it in the beginning?

I do it in the beginning because I don't want to waste my co-founder's time with like technical interviews. And so I do that and then, you know, we'll pass it to him for like a 30 to 45 minute kind of technical interview. We've kind of rotated. Sometimes it'll be like a database design question or stuff like that. Specifically, like things that we need to solve, which are complex, hairy backend problems. And so, you know, someone who's a scrappy hustler that's built a bunch of side projects that has TypeScript experience and thinks about, hey, I can get in the weeds on complexity, is probably the right fit for us. And so we run them through that for 30, 45 minutes. Then we do an in-person interview with the full team for— half hour to an hour, and then we, then we make a decision. I'd really like, if possible, to do like work trials as well. And so that might be like a Sunday for 3 hours. One, you can see if someone wants to come into the office on a Sunday. So that's, that's step one. Step 2 is you can like really see how someone thinks, and it's a good matching process to see like, are they the right fit? Do they like us? Do we like them? Is it kind of the right fit there?

Yeah, I was gonna say, I know you've mentioned the weekend thing. It is a pretty big weed out. It's like, do you want to meet on a Sunday at 3? Probably not. Most people will probably say no to that. And then, you know, well, probably shouldn't come join the call.

Yeah. And most people aren't going to build like multi-billion dollar company. And so for me, it's like we have to do whatever it takes to maximize those odds. And I can't guarantee we're going to win, but I'm hell is going to do whatever it takes.

So one question I've been asking a lot of people lately, because I'm always kind of— I've actually learned a couple of things and find a couple of tricks from this. Any new software tools like AI tools or anything like that that you've started using lately that's been pretty helpful?

Yeah, I would say this is crazy. 90% of our AI usage right now is Sonnet 3.5. We're not using ChatGPT anymore for a lot of reasons around analysis of docs and CSVs and that kind of stuff has typically been better suited in a Sonnet than a ChatGPT. We'll see if that changes with ChatO1. On the engineering side, everyone's using Cursor plus Sonnet has been kind of the primary stack. For me, I think I talked about that artifact that I was using earlier for content creation stuff. I think that's been super useful.

Man, I had another guest, Michelle Valentine at Anrok. They do tax, sales tax stuff. Another not that sexy industry, but it's actually pretty interesting. She was talking about how she used Claude artifacts also. So I think I need to start using it.

I've had multiple people now. It's like a game changer. It's so much, it's like significantly better. Now, I think like long term, I mean, I don't want to— Sam Altman's the GOAT. Like, I don't want to short Sam Altman long term.

Yeah.

But I'm obviously a fan of his, but like, we'll see what happens. One other tool that I use all the time is called Hemingway. Basically, what's been popular on Twitter lately is this idea of like screenshot essays. And so I will open this up. It will basically— it's like kind of like a souped-up text editor, meaning it tells you like, hey, this is a run-on sentence, or hey, this is like a 5th grade reading level, or hey, this is a 7th grade reading level, or like, like, these words should not be used. Don't use adverbs here. It's like overly wordy. And so I'll use that in their edit mode and then I'll change it to their write mode and take a screenshot of that and then post it on LinkedIn and Twitter.

Interesting. So it's when you're using Microsoft Word or Google Docs, it's just a blank text editor. But this almost has editing superpowers while you're writing. It'll just come up on the screen.

And it'll tell you, it'll like highlight it. And then on the right-hand side, it'll be Yeah. Wordy, runny, run-on sentence, like 6th grade reading level or like whatever. And typically, like in content, you wanna write at like a 4th to 5th grade reading level, even though your viewers are much smarter.

Talking about brain rot. This is why everyone's getting dumb. The TikTokification.

Oh my God.

The 5th grade reading level.

The TikTokification of my LinkedIn feed.

Yeah. Well, so, and you've kind of used LinkedIn and Twitter, you have used historically, but then also using it as kind of go-to-market channel. Is that, is that the strategy for Handlebar?

Yeah, I'm like obsessed with this idea of founder-led content. And I think a lot of people have started doing this and it has— it's become somewhat consensus. But the idea is like people follow people, not brands. And so no one wants to follow, you know, Banana Capital LinkedIn page. They want to follow Turner, right?

Yeah, I don't even think I've ever posted from the Banana Capital LinkedIn page.

Exactly. So it's kind of like this idea of like people want to follow people. And so like Going direct to the audience, not through some PR agency, but through your own content. I think a lot about me being kind of the voice and pounding the drum of legacy fund admins versus Hanover and here's why we're better and that kind of stuff. But yeah, it's been a good outlet and I think about it as a sales channel too.

Is that a drum that you're pounding? Hanover versus legacy?

As soon as we launch live, I'm ready to go.

We just launched a couple days ago.

Yeah. I wrote this manifesto actually that you guys can check out on our site, which is like, it outlines this thesis of what's wrong with the legacy fund admin landscape and what we're doing to change it and why I think this is a massive opportunity. And so people might get a chuckle or two. It's the Anti-Jargon Manifesto.

Wow. I did not know you could I did have a manifesto on fund admin. Wow. But I haven't actually read it. I think you sent it to me. Maybe I did read it.

Yeah, it's there somewhere.

Yeah. Okay, cool. I will definitely check it out. Well, this has been a lot of fun.

Yeah, you could follow me @chrishlad on Twitter or hannover.co is where we're at.

Awesome. Thanks for coming on the show.

Awesome. It's great.

And thank you for listening. Make sure to check out the show notes if you want to go deeper on some of the topics mentioned throughout the conversation. If you like this episode, it would mean the world if you liked, subscribed, commented, followed, and shared it with a friend who can learn from it. And if you don't want to miss future episodes, subscribe to my newsletter, The Split, in the show notes, and you'll get links plus a transcript for every new episode emailed directly to your inbox. Thanks again for listening. See you next episode.

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