#084: Chris Hladczuk Closed a $25M Deal After 26 Follow-Ups — Here’s Exactly How

But the story there was basically that there was this company, they had raised like $30 million and they were on a competitor of ours. And I have a great call and the guy's like, oh, it's kind of interesting. Talk to this other person. And then they just went into a black hole, which like when you go into a black hole, my like key framework around how to like do follow-ups correctly is you don't just like send friendly follow-up, friendly follow-up. You don't just like keep sending like a valueless follow-up email.

I would be like, okay, Welcome back to Season 4, Episode 7 of the Turning Pro Podcast. Today we have Chris Hladzik, who's the co-founder and CEO of Hanover Park. Thanks for joining today, Chris.

Let's do it. Pumped.

I feel like we were just having like a 20-minute conversation that honestly should have been on record.

We should have. There's a few things we struck from that, so I'm glad we didn't.

Yeah, that's true. But we, I think we can start with a very interesting conversation right now, which I think is probably one of the most talked about topics in all of media, is just like what AI is doing to the broader ecosystem of technology. And I know that's an extremely vague way to put it, but I think relative to the two businesses we both operate, so yours and mine, and we can get into what you're doing, I think it's more around how you see the intersection of services business and pure-play software businesses, where now I think the new thing is a middle of those two using AI to just make the services piece so much more efficient that there's no need to call yourself a pure-play SaaS.

Yeah, I think SaaS is dead is my, is my take. I think like you looked at 100 SaaS apps that were all building the same thing 10 years ago and it became a moat to build that over 18 months, 24 months, 36 months. And a lot of those learnings were like, great, I learned a lot of things about a customer and now I can, I can have something that's useful. Now you see 100 lookalikes of the same exact thing. And as it becomes easier and easier to build software, it becomes less and less— it becomes more and more commoditized and less important. And so like You know, the tact we've taken is, hey, what took 50 engineers you can do with 5 engineers today. And like, there is no moat in building software anymore. And so we went down the AI-powered services route, which we can talk about.

So what do you think is— if SaaS is dead, like, where do you think the moat is if we fast forward 24 months from today?

I think data is the moat. And so like, when I think about, you know, if you look at Rippling, right, they have this like core data asset of employee data. And then on top of that employee data, they can like build all of these things on top. They can build expense management, they can build payroll, they can build all these other things, IT device management. And it's all like built on top of like having the system of record of data. And so like for us, we're like, what is the core data asset that like is important for an investment firm? It's like their financial data and their accounting data. And then on top of that, there's all these things. But like if you don't own the core data asset or the system of record, like you're kind of plugging into something that might get steamrolled by ChatGPT in 12 months.

Interesting. So you think like, let's say fast forward 24 months from now, you're starting a company for a new company for the first time and you're ideating on what route to go. You're saying like start at the infrastructure layer where you can capture a dataset that is actually defensible because it's sheer scale of the data that you have.

Part of it is like I call this like chewing glass and staring into the abyss, to quote Elon. It's like what I'm asking someone to do is rip out their existing fund admin, which is basically ripping out the most important vendor for their firm. It's like an ERP for your firm. No one rips out their ERP. I know that's crazy. I joke with people. I'm like, I'm asking you to marry me on the first date. It's like that level of intensity. However, so to get, you know, we're not going from 0 to $100 million in ARR in 12 months, obviously. But once you have those folks, you can iterate and build with them and it's super sticky. And then you can like build all of these adjacent things to serve them because they're your default source of truth. It's the Salesforce playbook. It's the HubSpot playbook of like build a CRM, all the data's in the CRM, then you can build marketing automation, then you can build all these other offshoots. So that's kind of how I think about it. We'll see if I'm right.

It's interesting because my business is similar, just in a different industry, in different vertical. Like we are rebuilding storefronts for e-commerce brands. So like going to a $25 million brand and being like, hey, here's why you should rebuild your entire website with us. It's like, that is the thing. You don't just like turn your website off or switch who's building your entire website. So I'm curious from your lens with the business that you're in, the same way that it's super sticky, what that means on the other side of it is typically there's a high barrier to entry and you need to have such a compelling pitch to convince someone that's managing millions or billions of dollars to go through that process? Like, what have you learned in terms of how to craft that to make it compelling enough for someone to do it?

Yeah, it's a 3-step process. It's like, why can you trust me? I'm literally— this is like the highest trust, right? And so it's like, who are the accountants that are working on my account that are super experienced? How many assets do you have? Okay, we have $1.5 billion in assets. That's more trustworthy if you're a $50 million fund, right? And so like, you know, why can you trust me? Spend a lot of time on this. Why is this 10x better than anything else in the market? And so like, AI portfolio management products and AI inbox analyzer products and like differentiated things that literally like no other fund admins even thought of. That's the second. And then the third is always, isn't it such a pain in the ass to switch? Chris, I shouldn't do this. And so like, I am crazy. Like, I'll literally fly somewhere to migrate them on site. I'll like go and be like, you sit back, you drink your coffee. I'll literally click buttons on a computer to get your data and get this done. And then like, I will sit there and charge you no money for 4 months, 5 months, 6 months and operate in parallel. And so it's like if I can make this riskless for you, if you think this is compelling and you have no risk to doing this because I'm doing all the migration, you're not paying anything for a while, why would you not?

What's the craziest story that you have?

Oh, there's, there's, there's so many that you can— that you feel comfortable—

what's the craziest one that you feel comfortable sharing that you don't have to name names?

Oh my God. I don't know. There was one where I literally wouldn't leave their office until they signed the contract. I was just like, I'm here, I'm staying. Like, I would keep booking hotels to hotel tonight to the next day. And like, they like, you know, obviously I'm not like a jerk about it. Like, they love it. Kind of like they love the mania.

They want to feel— they want to feel wanted.

They want— yeah, they love the maniac energy that like, if you are like, we are the provider you call when there's an important thing with an LP. We are the provider you call when an LP wires $20 million when they should have wired $15 and they accidentally made a mistake and then they're caught. Like, we're the critical provider. And so like the fact that they can— they know I'm maniac enough to like stay in their office and camp out and make sure like my reputation's on the line for them to get it done. Like, I think some people like it, some people hate it.

Do you want to give a quick 30 seconds for people listening and like exactly what it is that you guys do? Because I know we just kind of jumped right into it.

Yeah, totally. I Native Fund Admin. Fund admin. Think about it as like the back office brain for a venture fund, private equity fund, private credit. We do all of the accounting and reporting from the the fund to the limited partners, like Harvard Endowment from whatever venture fund is there. And so that's our core job. We do that, we do the capital calls, investor portal. There's a lot of adjacent things that we do, but core thing is do the financial reporting to LPs. And our thesis is that as we've centralized data that used to be in 18 places in these legacy fund admins in one place, we can build a bunch of differentiated AI products on top of that core dataset. And so we've built an AI portfolio management where we take deal docs, we extract out a bunch of key terms, and surface data they wouldn't have before. So yeah, that's us in a nutshell. We have $1.5 billion in assets right now serving only venture.

Interesting. It's so funny because you are like, you're a persona of a founder that I know very well where it's just so clear. Like, I mean, I can't be the first person who's told you the similarities between you and Cyrus are crazy.

Yeah, we work together. Yeah, which is fun.

It's just like the The speed. I can just see like speed is everything to you. It's so like, I don't know, Cyrus's whole thing is like, by the way, we're talking about Cyrus from Haven because it's like speed kills. His main KPI that he tracks is like response time to customers on Slack.

We track that too. We, we— the thing is, I— at Meow, we had like a crazy— I mean, Brandon, our CEO of Meow, we had like thousands of customers and he was responding within like 5 minutes to customer requests and like When you feel like that rubs off on me now of like, you don't learn customer obsession until you like see what greatness looks like and then you're like, that's a different bar.

How do you think about that in terms of like what you learned in a culture like that to then bring that over to starting your own company and like the type of culture you want to build? Like, does that, does that spill into your hiring process? I'm assuming.

Yeah, we could talk about hiring for a while. I literally try to filter people out. I'm like, we're going to be 9 a.m. to 9 p.m. in the office, all locked in a room together. This is not for everyone. Here's the crazy vision of what we're doing. And like, if you want a 9 to 5 where like you're going to hang out and sing Kumbaya, like, this is not the right fit. This is like a Navy SEAL team. The right people love that because they're like, for engineers, I have really insanely challenging technical problems, like building AI agents to automate the most complicated financial firms on the planet. That's insane, right? Or like on the fund accounting side, like I'm at a legacy fund admin that I have no career mobility and trajectory and like I can get onto a rocket ship and figure it out. So that's exciting. But yeah, I have a lot of other learnings there.

And then I guess I'm curious to know what your actual process is like because it sounds like 99% of people don't make it past the first 10-minute call.

Yeah, huge top of funnel. So like I will be running outbound, like I kind of think about it like running a sales process. And so I will be running hundreds a week. I have like an overseas EA which will literally manually LinkedIn connection requests with people that are in our ideal customer profile. And so it's like, I'm hiring a founding head of ops. Here's the spec of what that looks like. Here's 10 examples of profiles that are good. Let's go attack 200 of them a week, right? Maybe 20 of them accept the connection request and then I will be DMing them and scheduling a call and then be booking like 4 to 6 calls from like 6 to 8 PM through like a Cal.com link every night, right? So it's like top of funnel. I also use recruiters. I also use like, obviously I get a bunch of buzz when I post on like LinkedIn or Twitter, you get inbound, but like those are the others. You just need like blocking and tackling. What is my top of funnel to like get this position? And so it's like first thing is get an insane top of funnel by like just being a dog. Like I think like people don't— and I remind myself of this all the time, like I'm founder-led sales, right? Like I'm doing my own thing now too. You have to have so much more volume than you expect and like do it. Sending 20 DMs a day is not going to get the job done. And so I think about the same thing with recruiting. And so it's like first call, you know, I will one, spend most of the time pitching us. Like I cold outreach to them. They're like, who is this crazy redheaded guy in a room telling me about an industry I don't know anything about? That's not a good start for them, right? So it's like I will go and pitch ourselves for 15 of the 20-minute call. If they're like, actually, this kind of makes a lot of sense and I think this is a really good idea and whatever, then like I'll spend 5 minutes just like filtering people out immediately that aren't the right fit. And so I'll be like, look, this is our work culture. People really love it. Like, we eat dinner as a team. We have Chipotle at 5 PM. Like, people love that environment, but like, you might hate that. Do you want that? And like, they'll be like, oh yeah, I don't want that. And like, perfect. So I do a lot of filtering out there.

What about— because this was something that was weird for me when we first started our company and started hiring. But I think as time goes on, you get so much better about it. But just like your filter to cut to cut a conversation short when you realize it's not going anywhere?

I literally just say, hey, you're really busy. I'm sure you have a lot going on, but like, I don't think this is the right fit. I'll just like cut it pretty quickly because it's better for them. Like, the worst thing to do is like, hey, we should have another call to talk about why you're not a good fit. Like, it's kind of—

yeah, no one, no one has time for that.

Yeah, exactly. And like, people that we're hiring, like, I'm sure they're a great fit for other places too.

I want to talk about the founder-led sales thing because it's how my company has grown as well. I mean, it's how Cyrus's has grown, amongst others. Like, what— two, two questions for you. One is, what do you think most people get wrong about founder-led sales? And then what are— what are you think— what do you think are the characteristics that you need to do it well?

Yeah, I think everything is about counter-positioning to me. And so when you are a VP of sales at a 100-person company, you have more resources, you have well-defined processes, you have more customer case studies. Like, you have the advantages of scale, right? And so you can run like, hey, I'm going to do a discovery call with an SDR and then, hey, we're going to do a demo and very structured. What I try to do is like, how can I be the opposite of like the well-run sales machine process? Meaning I will literally be like, I'm not a sales guy with a quota. Here's the no bullshit thing of actually we're going to ship in the next 3 weeks to like deliver 10x value for these customers. I'm not even a sales guy. I don't even want you like, you know what I'm saying? Like, I can say things that only I can say as the founder.

Yeah.

And that differentiates me in the eyes of every single person that's a buyer. So it's like, would I rather be talking to a sales guy with a quota that seems like he's trying to make a commission, or the person who's like, I literally— all I care about is 50 customers loving Hanover Park. Literally nothing else matters. And so I'll turn you away if you're not the right fit.

Do you think that ever needs to change, though, in your business, given how big you're— I'm assuming your ACVs can become?

Change in terms of no founder-led sales or—

Yeah, yeah.

Like, oh yeah, of course, over time. Like, it's just kind of the stage we're at of like, it will change, I'm sure. Given the ACVs, the good news is it won't change for a while.

And I also think at least what I've seen with some other people who just have that muscle is like, I don't know if it will change so much as you will add additional streams because you will never lose the muscle of just wanting to close deals. Let's be honest, it's fun. I mean, it's exhilarating. It's fun. You can have people who can help in parts of that process, but like, you're always selling.

I mean, I'll literally tell a story. Like, I had someone for— and I wrote a blog post about this. It was literally like 5 months. The guy told me, stop, stop bothering me, stop talking to me. I already signed with your competitor, whatever. Like, 5 months we have emails back and forth, him, his associate, the GP, and they're like, nope, like, not a good fit. He sees I post a case study last week with someone that he knows, and he literally was like, he emails me and says, What would it take to migrate? I immediately scrape his number, call him immediately. I'm like, hey, it's me. Hey, it's me. Can I come over to your office right now? He's like 2 blocks from my office.

And so I literally—

he's like, he's like, no. So I'm like, okay, great. So we literally go and we schedule a meeting and I show up and I'm like, I'm the crazy guy who's been emailing you for 5 months. And he's like, literally 15 minutes later we signed the deal.

I mean, look, I just think it's—

you're—

if I could give one piece of advice to people who are listening who want to get get into founder-led sales, my piece of advice would be, do— be willing to do things other people aren't willing to do.

Like, I'll get on a plane on a whim. Like, I literally get on a— I'll tell someone I'm gonna be in Ohio and I'll literally just book a flight and go there.

Like, breaking out of that mental model for your first time, like, if you come from a corporate position, yeah, to know that, like, it's okay to do things like that. Think about it, like, you're working in, like, a corporate job, it's like, oh, I might get in trouble if I, like, tell a client or a prospect I'm just gonna get on a plane and, like, it seems intrusive and rude or whatever. But like when you do things that no one else does, you actually resonate. Like for better or for worse, this client that took you 5 months to close, you were maniacal. So even if he wasn't your customer, he still knew who the fuck you were.

I mean, he literally—

you were never going to leave.

This energy is insane.

Exactly.

He was like, this energy is insane. He's like, I love it, which is great. So I don't know, some people love it, some people hate it. I think it's just like, I mean, I remind myself this literally every day. It's like you need to be relentless because like if not, you're going to be the same as pick your competitor sales guy that's like goes home 9 to 5 and whatever.

Where does this chip on your shoulder come from? I don't know.

I like— there's a lot of people who raise a few million, but like we've raised $3.5 million at this point, like raise a few million bucks, they do fine. And like, you know, quietly the business doesn't work out and it goes away. And like, that's the state of the world for raising, you know, first or for one or two rounds. I just have this crazy chip on my shoulder. I want to be the exception to that. And like, I started when I was in college being like, it's hard to get a job at Goldman. It's like 1% acceptance rate. Like, I'm going to do that. And so I don't know, we'll see. We'll see what happens. But I just like this. I want to find a way to make it work in a, in a world where like it's very competitive.

I want to talk about that. I feel like you, you went through the, the boot camp that is perceived to be one of the pinnacle boot camps.

Yeah.

For lack of a better term. What are your thoughts about that experience? And knowing what you know now, if you could go back and do it again, would you do the exact same thing.

So I would have. I think if you're non-technical, so like this advice is for people that want to start a company, they want to be a founder, but they're non-technical. Like I think there's really two ways you add value, either write code or you sell code. So like ops is not a way you add value in a startup, especially early stage. And if you're not going to write code, you have to find a way to gain skills that actually give you an edge. And so like me being at Goldman, joining a company like Meowth, selling into fintech, selling to CFOs actually gave me like a huge advantage. I built like a ton of inbound trust. And so it was like, okay, find a way to get an advantage. And then the other thing is like having to work 100 hours a week. I mean, it wasn't 100, maybe like 80, having to like be in the office at 1 in the morning on like a Tuesday night when like you are swapping commas for like a 100-page slide deck for a client that's due 9 a.m. Eastern and like the pressure's on you and you're presenting to like do like a billion-dollar financing deal. Like You don't get that when you're 22 and 23 anywhere else. And so as much as people can shit on like investment banking, you're just a drone, like you don't actually learn anything, like go learn, like go do something else. Like that intensity, like makes me feel when I leave the office at like 9 p.m. on Tuesday night at my current company, I'm like, this is easy.

Yeah, I think it's— you were able to withstand that and then know that you can do something that doesn't have to be at that level of intensity to achieve significantly greater outcomes. But I think one of the, one of the things I think about with it is the perception of like the amount of time you spent there versus the amount of time you're actually being productive. I think the difference is like you have to put on a face sometimes, right? Because you might get something from your MD at 8 PM like, hey, I need this done by tomorrow. The difference is when you're a founder, like no one is telling you when to do what. It's on you to just make sure you're getting through whatever it is you need to get through. And you decide like, what does productivity look like and what's your bar for that?

It's so different. I literally joke. I'm like, sometimes I joke. I'm like, this is even though you might work more hours at a place like Goldman, like everything you're doing is something someone told you to do. They're like, we had this client now, like, make this slide deck, right? It's like very like structured, even though you're working a ton. This is like there is no structure. Make the number go up and make the company work. Figure it out. Which is like kind of the opposite, which is why people have this reputation of like banking consulting being like it doesn't help you at all to be like a good founder. Right. And so that's kind of the argument.

Yeah. I mean, I, I don't know if you know this. I mean, I've talked about this. If there's anyone who's actually listened to every single Turning Pro podcast, if you ask them like, what's one thing you remember from listening to those episodes, it would be the fact that I gave up my corporate job 12 hours before my first day.

Yep. I know this. I listen to every episode. I love that.

And so I say that to say that, like, you're lying to yourself if you think there's not certain things that you learn from those roles that can make you a successful founder. The thing that I will say to you is I think there are a lot of people who go through that who can't break away from certain behaviors there that make them a bad founder, right? Like going into uncharted territories, doing things that are not acceptable by like the social eye. That environment is all about like following the rules, staying within the lines, like dressing the right way, speaking the right way, presenting the right way. But what stands out in the world of like startups and entrepreneurship to me is like the people who do things differently. And they're misunderstood for a long period of time until one day everyone wakes up and is like, wow, you're right the whole time.

So true. Amen. I have nothing to add to that.

I just feel like that is my only— that is the only pushback I have. I'm not going to sit here and tell you that I can look at a model the same way you can because I can't. And I know that and I never will be able to. And that's okay. But I think I would bet on the former bankers who, you know, similar to you, have the chip on their shoulder, can take like the hard skills that they get from that but like break away from this like box that you live in because you need to be creative. You need to think outside, outside of that box to do things. And I think unfortunately there's a lot of them that never do. And so I think there are some who are meant to be bankers for 40 years and there's nothing wrong with that. I don't have anything against it. Yeah, just like choose your journey.

I think it's because I literally, I would still be a private equity or banker if I wouldn't have started writing on the internet for sure. I think it was literally like all of my friends because it's just you become the 5 people you're around. It's like that cliché quote. I was like, writing why Disney is a cult and why every great business is a cult and writing like deep dive essays. And like all my friends were like random people that were like building things. And I was like, wait, like you can do that? You can just like go build a company and it works and whatever. And they're like, yeah. And so that like, that was to me the entree or I would have kind of stayed on that path.

What prompted you to start writing on the internet?

I was literally like, okay, this is my, this is my crazy brain. I was like, all right, I think tech is cool. I was reading like Paul Graham and Sam Altman essays in like 2020. I was like, my dad sells insurance, so I literally had nothing to do with tech. I was like, tech seems interesting. Okay, there's a lot of people in tech that are on Twitter because back then it was like very like tight ecosystem. It's changed a lot since Elon bought it, but it's like, okay, all these people are there. Great. I'm a no-name college kid. Why would anyone ever follow me and why would anyone ever respond to me? So I'm like, all right, I'm going to go join this dumb Yale startup club. They're all kind of like fake. I'm going to be the head of speakers and podcasts like this and then invent a title and then interview a bunch of big-time founders like Emmett Shearer, the CEO of Twitch, Kevin Ryan, who founded Mongo, and some others. And I would turn all that into tweet threads. And so I was like, I'm going to weaponize the data that I have, which is Yale founder who can get live interviews with these people and put it into a platform where no one else has interviews with Emmett Shearer or Twitch. And then that would be my credibility hack. And so it was very like, people say, oh, I just kind of stumbled into it. I was very contrived. I was like, hey, I got to figure out a way. This is really interesting. I want to meet other people on the internet. The only way to get distribution is to have some sort of unfair advantage. I found it. And so, and then I was like, great, now I have something. And it took like months, like literally like 9 months of 100 followers. So, you know, I almost gave up a few times too.

I think that's a very good next topic to have a conversation about, which is just this notion of consistency. Right. So I'm sure you've seen the meme where it's like the dude, like, breaking down the wall.

Yeah.

Like, one guy's turning around and it's right on the other side of it.

Totally. I— so I have so many examples. It was literally like, okay, you know, I write on the internet for 9 months. I literally, like, have 200 followers. I was about to give up. I literally was like, I don't think this is for me. Like, every time when you have 200 followers and you write a tweet, you get 0 likes or 1 like. And it was like, be like my mom. Like, my mom would log in and give me, like, a pity like. And that was kind of where I was at with, like, thousands of tweets. And then like one breakthrough happens and I go from like 100 to 10,000 followers overnight. And then it was like I literally had given up a month before and was like, I'm not going to do this. And there's been like so many examples. I mean, whether it be like, hey, uh, meow, this, uh, this deal that I was supposed to give up on that was like a $25 million asset deal. Like I sent 27 follow-ups over 6 months and on like the 26th they're like, Wait, let's do this. So there's been a lot of examples there.

I mean, that, that is a hook.

Yeah.

Here's how I close a deal on my 26th follow-up email.

Clip that. Yeah. No. So, so the story there is we can clip that around. But the story there was basically that there was this company, they had raised like $30 million and they were on a competitor of ours. And I have a great call and the guy's like, oh, it's kind of interesting. Talk to this other person. and then they just went into a black hole, which like when you go into a black hole, my like key framework around how to like do follow-ups correctly is you don't just like send friendly follow-up, friendly follow-up. You don't just like keep sending like a valueless follow-up email. I would be like, okay, how can I fit 27 follow-ups and don't seem like an asshole because I'm really annoying to them? I can send like a LinkedIn DM follow-up to one of the guys. I send another LinkedIn DM follow-up to the other head of finance guy. then I send an email to one guy, then I use our collapse chain where it's all three of us on the same chain. Then I send them like a piece of value, a.k.a. like T-bill yields are changing. Here's what's happening. And like, I hit them in like 70 different directions. And then it was like the guy was like, wait, actually, I'm interested in that. I was like, I thought you forgot about me. I thought you put me in spam like 2 months ago. And then, you know, he wired $25 million from a bank I'm not going to name.

Have you made a guide or like a— you should make a guide on like, here's the playbook to follow if you want to go the distance on like 30 follow-ups.

I actually should do that because I've done like a—

no, because I'm not, I'm not even— I'm not even joking. Like, it's— there's, there's different things that you just said that can be interesting of like, okay, if there's 2 people on the thread, follow up twice, then send one guy LinkedIn, then send a piece of value, then like invite them to an event, then do whatever the hell it is. It's like if you try these 25 things, probably not the best use of your time.

Yeah. And my thing is, is like you got to know when to like lean on— like I literally lost a deal the other day where I was like, I didn't do the 25, I did like 7. And then I was like, oh, they must be busy on this, this, and this work stream from this thing. And like, that's the lesson I need to relearn. Like, so I'm not 100% not infallible, right? Like, I definitely make mistakes on these things all the time, but like, literally, if I just— it's kind of like the dumb brain, like, Midwood advice where, like, if you want to be healthy, you should just, like, get 8 hours of sleep, like, drink water, work out, whatever. It's like, in sales, or I do those things, by the way.

Nice.

Yeah. In sales, all 3 of them. Yeah. I wish I did more. But in sales, it's like, consistently do outbound. Write 5 pieces of content per week, follow up on all these things, multi-thread. Like there's like a list of like 6 things where it's do those things and like be relentless over a long enough time horizon. Like hopefully you get lucky.

How do you actually— I'm curious because you've obviously grown a very big audience on Twitter. Like what is— how have you seen the platform change and like what do you think resonates right now?

It's changed a lot. I think like the whole Thread Boy thing's dead, like writing generic listicles is dead. Everything I write now, I basically— my process, I spend like 4 hours on a Sunday writing like 5 posts. Everything I write now is personal experience that only I could basically talk about and is tangentially related to what we're doing. Meaning it's not going to be like shilling Hanover Park. It's not going to be like, buy Hanover Park here. Like, that's never going to work. It's going to be like, last week I talked to the CFO of a $2 billion firm and he told me he wanted to quit. Something like that, right? So it's like I had a real conversation from something that only I could have. Here's like a fun hook on that and here's something tangentially related. Like other CFOs will read that post. That, that is my ideal customer profile, right? So that's kind of how I think about it of like right now I'm like weaponize what we're doing in like a personal way without shilling.

Yeah, interesting. And then my other question for you is how do you think about using AI as a means to not like write all your content, but to like help you better frame concepts?

Yeah.

So I just think anyone who's like, oh no, everything is purely my own words, I'm like, you're doing yourself a disservice. Like you can always optimize things and it still can be your own unique thoughts. And then my second part to that question is your thoughts on each of the different tools between like Claude, Deepseek, ChatGPT.

Yeah, like I've, I've played around with like, I think hook writing is the hardest thing. And so like hook for everyone that does it is for sure. Hook writing is like first two, like in LinkedIn it'd be your first two lines and Twitter would be like your first three lines typically. And it's like getting that right is basically the 80/20 of all of content. And so every time I have a post that does really poorly, it's because I didn't spend enough time on the hook. And so I've tried to do a lot of things around like taking a Claude project and putting a bunch of existing hooks that have worked for other people and then like feeding in an existing LinkedIn post of a completely— like, it'll be like something for chief marketing officers, like completely different than what we're doing, but like stylistically matching the hook for something that could be related to our spot or our specific, my specific story. And so I've tried to do that. I wish I could get better. So if you're watching this and you like knew you have a bunch of hacks on this, like let me know.

Yeah, I mean, I think the thing I see often talked about now is how like one of the most in-demand jobs that will— I mean, it's already emerged, but will further emerge over the next couple of years is like prompt engineers.

We'll see.

Or I don't know if that's— I don't know if that's true or not, but I do believe if there's one thing I do know to be true, given the fact that like I would say on a scale of 1 to 10, my knowledge of AI is probably like a 3, like relatively. Maybe I'm delusional because of the people that I'm around all the time, but I do believe that like it's only as good as your ability to leverage it.

Yeah, I think my hot take is maybe no one will ever write a prompt again because we're going to be writing the best prompts for AI. That's a crazy take, though. Whoa. Yeah, just, just toss that nugget.

But the, but the only thing to that is like you need to tell it what types of prompts you want it to make for you.

So it's kind of like, um, well, it's not gonna make prompts like it's not unless there's always gonna be a problem.

Okay, let's go, let's go big brain idea. Imagine you have a fucking Neuralink and you think about a prompt that you want and then the AI goes and writes the prompts.

I actually made— what's a great— here's a crazy idea. It's no one— what if it's not thinking about a prompt that you want? What if it's just thinking about the outcome that you want and then AI figures out the prompt and the execution? So you're actually just thinking, like, for example, I want to have day one quarterly— this is super boring, but I want to have day one quarterly financial close for an investment firm instead of having 45 days. If my goal is have day one close, AI would just like write the associated prompts to auto-categorize the cash transactions perfectly. Instead of us building a bunch of evals out to figure that out. So like, that's a super giga brain idea, but like, is that the future we're going towards?

My brain is just—

here's a job, do it.

It's all— but also like, what— who is building like the Duolingo for AI? I'm assuming that exists.

Like, yeah, like, how do you—

how do you get my dad to start using AI in his day-to-day life?

It's so funny, my dad uses Grok every day.

Really?

Yeah, he loves, he loves Twitter.

I mean, I think the— I, I do think that the, the guardrails around how to use it is the thing that needs to be cracked for it to be like mainstream, uh, mainstream to a point where like people are using it in effective ways. Because I bet you, of those 500 million people that you said are daily active users of ChatGPT, 480 million of them are like Where should I eat dinner tonight? Like, can you fix the grammar on my email? Like, very surface level. Sure, prove me wrong. I'm guessing it's probably— or higher than that. It's 1% that are actually like able to extract mind-blowing things out of it to just like make breakthroughs.

I also think like people— I literally had a friend the other day, he's at, uh, he's at CeraVe, like a large, um, you know, fat— yeah, a large skincare company. And he's like, oh, I want to play around with building some AI workflows out. So he was like hacking around And like he got like 12 hours into it and he's like super smart guy that's like kind of technical. And he's like, he got 12 hours and he was like, holy shit, this is hard to actually like build something that's useful. Like people underestimate how hard it is to build like an actual workflow that actually works and that doesn't like hallucinate randomly or work 20% of the time or work whatever. And so that's a huge gap to me. And like we see this every day too of like going from Wow, that's a cool demo. And like, wow, that actually works 15% of the time to like, that is a bulletproof, bulletproof 100% of the time thing is like huge. That's like 99% of the work.

Yeah, I think it's 100% accurate. So it's like, what is the next phase of that where you have the thing that can help make it? Here is my crazy— my idea actually. Now we're just like in this spitballing conversation. An idea I had, and this probably exists, but What is the tool that essentially monitors your behaviors and tells you like what you're doing a lot of? And here's the solution from an AI perspective to fix that. So there's obviously an element of it being kind of invasive, but like if I said to you, Chris, put this tool on like your phone and your laptop and it's going to watch how you behave for the next 7 days and be like, you spent 8 hours doing— you spent 8 hours responding to emails and 90% of the emails you responded like this. If you just set up these 3 workflows, I can make you 20% more efficient. But imagine that concept.

If you can extrapolate that across an entire organization, there's a company called Highlight that's trying this. They're in New York. I don't— I've never used it, so I'm going to put my hand up.

Highlight what?

Highlight.ai. I don't know, actually. It's a guy, Pim. His name's Pim. He founded a company called Metal, which is like a pretty big gaming company.

Everything you love about Cursor across every app on your computer.

Yes.

Highlight.ai. Highlightai.com.

Yes. Yes. So I know it's like I, I'm going to try it now that we're talking about this on this podcast, but it's like I want something where— and for us, like, right, like we are an AI-powered services company, meaning like we have humans doing work. Like part of just figuring out how to automate stuff is like documentation of exactly what people are doing. And so like really complex accounting workflows, like the alternative is have an engineer literally sit next to a fund accountant all day long. We're doing that right now.

Oh, really?

Oh yeah. We're like trying— I mean, we're doing—

so it's what, for them to just see what their work is and then take that and like automate it?

Correct. Yeah. We're just like mapping. It's called like Palantir, because like mapping the ontology of like a workflow, it's like, what are the all these specific steps to like deliver quarterly financials? And then like, let's map that out and let's build workflows and processes. But like it would be 100 times better if I could just like everything on their screen and on my screen would be like mapped, traced. And then like, here are the 15 things that they're spending a lot of time on there.

I forgot there was like a— there's a plugin. I forgot the name of it. There's a plugin that I think also does something similar, like a Google Chrome plugin type thing. But yeah, this is— I just like if this actually materializes at the scale that I think it will over the next couple of decades, like, what do you— what does the economy— what does the workforce look like?

Oh boy. Now I'm an economist.

No, but do you think— do you think that there's actually like an existential risk of like, I don't know, like people earning income at like the lower class?

I'm more like it's just going to be a productivity— but like, for example, Rippling took, you know, when Parker Conrad started Rippling, he literally had 40 engineers on the early team because they were building such a wide product. Like, you can do what Rippling did with 40 engineers with like 7 right now or 5. And so I think it's just going to be like much more productivity, just like when we got computers and we could use Excel versus like literally handwriting numbers. Did investment bankers work less? No, they could just do more deals, right? So like, it didn't mean like Excel is a tool that was literally 100x output from like handwriting down numbers.

Do you see what Google Sheets just came out with?

No.

They have a command now that's AI parentheses. You can type in what you want the output to be instead of having to know the formula.

That fires me up. I was literally like screenshotting and putting it into OpenAI ChatGPT right now. Yeah, I love it.

Yeah, I guess that's probably like the, the most reasonable way to look at it is just like it serves as a productivity tool.

Like, I think more people will be able to do more. Like, it's just the same. I mean, I see it as just it's going to be 100x output on everyone's output. And I could be totally wrong, by the way.

But okay, so then how do you think about that more broadly in the realm of content?

Yeah, we were talking about this before we started recording. Like, my crazy prediction is like someone like a Joe Rogan won't be recording podcasts in 18 months. It'll literally be like his AI face in a room with like Elon's AI face, like talking. And I know there was like memes about this, like Steve Jobs.

That's because there's a— sorry to cut you off. That's because there's enough historical content on his voice that you can build that into a model. Correctively.

Yeah, correct. I mean, it's what Delphi is trying to do. Yeah. So like, I'm kind of of the mindset of that. Like, it actually could be a more compelling conversation because, you know, you forget to read, you know, my name and their bio and whatever in prep for this interview. Like, perfect recall, perfect accuracy, and then like infinite context window where we could record for 50 hours and just take the best 20 minutes. Like, what if we could record for literally 12 hours today and then we're just like, yeah, a lot of the bullshit we were talking about, about whatever, just wasn't useful. Here's the 20 minutes where like he talks about a story that's actually compelling.

I know, I just— because it's almost like so obvious that it's inevitable. But then my question just becomes like, you know, just like, you know, talks about this a lot is Gary Vee about like how there's just cycles of things. Like the last one I remember seeing a TikTok about was like him talking about Pokémon. It's like every other— it skips a generation, right? Like it's cool. And then the next generation it's not. And then it comes back. Like, at what point does this— do we ever think it collapses? And then the concept of human interaction and human element comes back? Or does AI become way too realistic that because you can't really delineate between the two, you're kind of like, this is the future.

I think it's kind of like—

I feel like we're down this, like, down this existential rabbit hole, but it's like, I feel like it's something that's worth talking about, honestly.

It's like people like listening to CDs. Obviously, it's better to just use Spotify. Like, I think people are going to, like, have nostalgia of, like, normal human conversation and normal, like, in-person stuff. And so that's going to, like, create, like, an antidote to the existing stuff. That's kind of my take is just like someone listens to records or listens to CDs.

Oh, okay. Yeah. And then, I mean, it just— it almost becomes like retro.

Yeah, it's going to be retro.

You're going to watch a live conversation like, yeah, like, dude, I've been watching AI for the last 10 years.

Yeah, like, literally, that's what it's going to be, I think.

If your company fails, why do you think that is?

Wow, that's such a great question. I think a lot of— so I think, I think a lot about like de-risking. Of just each individual step. So de-risk one is build a product to deliver to one customer. De-risk two is, can you get the technical team in place to actually deliver something this complicated? De-risk three is, can you get the accounting and services team in place? So each of these are different de-risking patterns on the path. And so right now we're focused on de-risking I would say getting customers at scale and being able to service them 100 times better than anyone else. And so, yeah, I think just focused on that, like we're in it, we're just like in execution mode right now. And so there's, that's our next big step.

Aren't you always in execution mode?

When you're in—

I guess my question is like, what is the opposite of execution mode?

When you don't even know what you're going to build and you're kind of like trying to be like, all right, what are we going to build? Is this a problem we should act like? I think there's Oh, like those ideas, or like, I need to like recruit a lot of people because this is like the— like, that's not really like— I'm servicing a customer, I'm iterating with them daily on product, etc.

Yeah. I want to talk about, uh, some of your operating principles around like taking Saturdays off, half days on Sunday. What is the, the cultural component here?

Yeah, I think so. We're 5 days a week in the office, like 9 AM to 8:30, 9 PM depending on the day, um, all in person in Flatiron. How big is the team now? 11 people. So we're all in person 5 days a week. And like we have this mentality, or I do, that like we work super hard, you know, we had dinner together as a team, etc. But like I will literally never ping you on a Saturday unless there is literally like a massive bug taking down the entire site, like crazy circumstances. Because like I think people need like an escape from the crazy, like, data. Like we're working 60 hours a week, like actually working hardcore 60 hours a week, people are going to burn out if they're literally doing that for like 6 months. They're like, I haven't even seen anything and I haven't had a Saturday off. Like, I think that's a major issue. And so we try to be like, like points of intensity during the week and then like completely off. You will never get a Slack message from me or any of the team ever. And then Sunday, you know, people have, you know, remote if they want to be. Some people come to the office. I usually do like a full day on Sunday because it's like a big prep day for me. But, you know, that's the right balance or work-life harmony that we've, that we found has worked for longevity.

How do you spend your time on Saturdays?

Literally try not to look at a computer.

So, so you're, you're disciplined for yourself also about like, don't work today.

I try, I try to be disciplined because it's like I'm in this for 10 years, 20 years. It's like you're in this for a very long time if you are working 7 days a week. 12 hours a day, 13. I just don't know how long that lasts for people. And so I've tried to be like disciplined about, you know, give Othership a shout out. Like I'll go to Othership in Flatiron, hit the sauna, that kind of stuff.

Love that. Robbie's coming on the pod in a few weeks.

Oh, he is?

Yeah.

I love— literally massive shout out. It's incredible.

And what they've built is amazing.

I'm like super impressed.

I have my own little Othership right there.

Okay. So you don't come anymore?

No, I mean, I go once in a while. I mean, they do a lot of really cool, like cultural stuff there now.

They do great events.

What I— that brings me to my next question. What do you do for fun? I feel like that's a really hard question.

Worst question you've ever asked.

It's a really hard question for maniacal founders because I think if I asked Cyrus that today, he would probably just say, fuck you.

Yeah, literally, it's like work, think about work. Um, I don't know, I like— and I couldn't even say like hit the gym. Like, I'm trying to figure that out too, but it's just like I go to Othership. I'll like go I've cut down on drinking pretty significantly in the past, I would say, 6 months. So like I'll drink once a month, you know, a little bit. And so like spend time with like people that are completely outside of tech, actually. I like to spend my Saturdays with like my friends that are not in startups because if I'm spending time with a founder friend, you know what it's going to devolve into. How's revenue? What? Like it's literally going to be—

I mean, I'm conversationally guilty of it also.

Like for the day that I'm off, I just like don't want to talk about it. And so I like, I like spending time with like my friends in other spaces.

Interesting. And then I'm also curious, like where, where do you like, what is, what makes you curious? Like outside of business?

I don't know. I like studying writing. Like I think like David Perel, How to Write His Podcast or How I Write His Podcast, like is super interesting. Harry Dry from Marketing Examples, if you know Harry, I guess, know Harry pretty well. And like his craftsmanship of how he thinks about like conveying information is like so— I know that's super nerdy, but it's like, no, it's so compelling for me to be like, how can you get someone to feel something from like a 7-word sentence? And it's just like, I find that super interesting. And so his newsletter is really interesting. And like his— I think it's copywritingexamples.com.

Yeah, but your results speak for themselves. Like the fact that you're into that type of stuff would suggest you probably have people who want to listen to what you have to say in the world.

I have a a lot more to go, but sometimes I do.

What would you say is your biggest turning pro moment so far on your journey?

I think, I think, I think becoming CRO at Meow was, or Chief Revenue Officer at Meow, was a big moment because basically it was like the belief capital from Brandon and Bryce, the founders, to be like, you were delivering 100-fold of like what our expectations were 10 months before I joined. So it was super fast. And be able to like go lead a team to take us through the SVB debacle and get us to $1.5 billion in assets by the time I left was like critical. And they're still— I'm still very close to them. They're investors in my company now. And so that was, that was critical. But, you know, a lot of time ago.

What was the moment where you decided it was time for you to go off on your own?

Yeah, I was just like, I love them too. And like, I am— I literally told Brian, I saw him last weekend. I was like, I am insanely grateful for him specifically. Literally during our fundraise, when we were raising for a seed round, he was like, this is the guy I bet on. This is the guy I believe in. Like, and he wrote a significant angel check. Right. And like, that matters a lot when you have nothing. Like when you have something, it's like easy for people to be believers. But when you have nothing, you know, it's super important.

It's also like the craziest signal for any investor. Like my former boss wrote like his largest angel check.

Whatever, whatever, by like a wide margin. So it's like, so that was, that was great. But yeah, I knew it was time. I was like, this is, you know, I thought this was the right, right thesis, right founder market fit, right story. And it was like, we're going through the greatest tech shift of our lifetimes. Like, this is the internet in 2000.

My last question for you. Is there any question that I haven't asked you that you would have wished I did ask?

Now I'm good. Not— you should ask me more about other shit, but more about other shit. Yeah, exactly. This is good.

Chris, I appreciate you coming on, man. This is awesome. You want to just look at the camera and let everyone know where they could find you?

What are you working on? At Twitter, uh, @ChrisSalad, and then search me on LinkedIn, Chris Saladzik. Awesome. That's it. Cool, guys. Thanks.