300 Coffees, 12 Years, One Big Exit

Never take advice from people who have not done the thing you are trying to do. The amount of people who give founders building company advice who have never built a successful company is astounding, right? You don't see in any other industry. You don't see people walking around telling you how to do surgery who aren't doctors. My whole thing is I think there's some people, you know, I like to say there's some people who did the equivalent of going to West Point, so they learned how to shoot the gun. And there's some people who have been to war and they know what it's like when the people shoot back. And you only want the people who have been to war.

Welcome to the Startup CEO Show. I'm your host, Mark MacLeod. In this episode, I sit down with Blair Livingston, co-founder and CEO of Street Context. Blair is a finance guy who turned himself into a startup founder, and over several years he built Street Context towards an amazing exit. That company kind of crossed the desert for a while and then hit an inflection point. And he walks us through that and how they got through that slow growth period, how they kept up in the fast growth period, how they had strategic investors, all these stories of hustle and how he basically willed his reality into existence. And then he walks us through the exit process itself. This story, this episode is just full of rich stories and actionable lessons. You're really going to love it. Blair, welcome to the Startup CEO Show. It's a true pleasure to have you here. How you doing today?

Great. And, uh, thanks for having me. I'm, I'm looking forward to our conversation.

Me too. Yeah, very much. And you know, uh, as a fellow finance person, I'm actually fascinated by you, uh, because I, I never started a startup because I felt I had to be either a product person or technical to start, but you are like a died-in-the-wool finance guy, and yet you started a startup. And not only that, but you, you brought it all the way to a great exit. So I'd love to just start with that. How does a finance guy become a startup founder?

Yeah, no, it's a great question. I think like many young people, when I was in university, I had no idea what I wanted to do. Uh, so I had the benefit of going to Laurier, you know, with the best and brightest, as it were. I did co-op and tried all kinds of doing that. I did a term as an accountant, which was probably one of the hardest things I've ever done. I did a term working for a CPG company, which was great. And then I had an internship on a trading floor and just the excitement, the energy, the passion, the intensity really appealed to me. And then the other thing that always appealed to me about finance is it's, you know, kind of secretly one of those industries that I think has more impact on people's lives than almost any other industry in the world because it impacts, you know, what companies can raise, thus which companies exist. You know, impacts currencies, like what's the Canadian dollar worth? It impacts interest rates, like what's your mortgage, what's your credit card? Commodities, like how much does beef cost, how much does iron ore cost? All these things are driven by these markets, and it's a fundamental core piece of infrastructure for democracy, because either you have central allocation of capital or you have decentralized allocation of capital. And not to say, you know, uh, finance and capitalism are perfect, but it's a very efficient market for allocating people with money, people who have money. So I loved the internship there. I had a bunch of ideas. And the funny thing was joining a trading desk and joining capital markets in general, it's very interesting where some of the things they do are so advanced and so bleeding edge, and some of the things they do are so outdated and so challenged. So I had an internship there, ended up having these crazy ideas of things I wanted to build and see and do. And a senior executive from New York was actually coming through Toronto and I ended up chatting with him. He invited me down to New York for 2 days. It ended up actually being an unofficial interview. I ended up then taking a job there out of university, and I wasn't even 100% sure if I wanted to go into finance. So I ended up working on a job description that was basically somewhat tailored to me. So in the mornings I worked as what they call a desk strategist. So Putting out commentary, content analysis. I covered European banks at the times, which were like the pigs for anyone who might remember, you know, they were all going under. And then the afternoon I worked on electronic trading and it was fascinating because I got to see the old school desk in the morning, which is, you know, traders surrounded by sales traders surrounded by salespeople trying to make markets, move securities, do IPOs, do block trades, do all this fun stuff. And then in the afternoon it was electronic trading, which is quiet algo development, software development, essentially competing with the principles of physics, right? As they try to get faster and faster. Ended up being there for about 6 months and looked around and realized, number one, I hated waking up at 5:30 in the morning. I hated, you know, how much of a grind it was. I think I looked around and saw no one really over 40 on the desk. And I decided I had a bunch of these ideas that I want to build. I went to my boss at the time, a guy named Brad Katziemer, who's now somewhat well known because of Michael Lewis's book called Flash Boys. He was like, listen, oh yeah, we have these exciting ideas about building a stock exchange. And I moved back to Toronto. I took some time and ended up going to join them to build the stock exchange. That was my first foray into entrepreneurship. And I kind of compare it to, you know, stepping out a little bit on the branch and seeing if it breaks, you know, away from the stability of the tree. And you realize you go a little bit further, then you can go a little bit further. And I got to see lots of things done well and lots of things done terribly. I, you know, and it's fascinating having joined a startup before starting a startup because you get to learn all these lessons essentially for free, which is a great piece. But I was there for a while. And, you know, while I love the team, I love the vision, I want to stay in Toronto and move back to Toronto, and I want to build my own thing. I think one of the biggest things being there is it wasn't clear, you know, kind of what my long-term role was. And I decided, and I actually wrote this in my journal way back, you know, I wanted to be captain of my own dinghy versus, you know, crew member on a frigate. And so I set out to start Street Context based on my experience at, at RBC.

That's amazing. I wrote down the word journal 'cause I wanna come back to that. But like hearing that story makes me think of a few things. One, like a benefit you were a beneficiary of, like seems like some real mentorship. Like I think back to my first job, like first of all, I did that accounting, but I fell in love with it 'cause I'm weird and became a CPA. But like my, and I love co-op and frankly, like I come from a poor family and co-op was the only way I could. Go to university, but it also gave me my articling hours. But like my first job, like I was making photocopies or like copying out literally on a 14-column, like a ledger of accounts, like menial work, not like, hey, let's design this job for you that like really stokes your interests and passion. And it's like, you're going to learn, like nobody was thinking about that. So I think you were tremendously lucky that.

Yeah.

Yeah. But I'd love to double-click into this instinct to build. And when I first came across a Livingston, it was Ted, who I understand to be your older brother. So I don't know, maybe tell me a little bit about how entrepreneurialism runs in, in your family.

Yeah, I mean, so there's, there's a number of good kind of questions there and conversation topics. First, just on the mentorship side, I think one of the really interesting things is the traditional education system really trains you to kind of follow a flow, right? You do this, you do this, you do this, you do this. One of the things that I appreciated going to university is like, I didn't have the best marks. You know, ironically, my two older brothers, Teddy being one of them and Michael being the other, always had great marks. And because I didn't have the best marks, I kind of had to find side doors. So I got really good at reaching out to people cold, messaging people cold, and, you know, to get my sales and trading internship at RBC, I probably had 300 coffees with people. And holy crap, I actually originally thought I wanted to be an investment banker. And there was one guy I met who was probably one of the most impactful people. He was on the investment banking rotation program and he's like, listen, I think you have too much energy and excitement to be an investment banker. Have you thought about sales and trading? And he's like, I actually know, you know, that they're kicking off the internship hiring soon. Like, here's the person you should reach out to. And during that interview, I was like, listen, I might not have the best marks, I might not be the smartest, but I'll do whatever it takes. I'll walk your dog, I'll get your laundry, blah, blah, blah, blah, blah. And they're like, this is great because they're like, you have no idea how many kids come in. And you know, I say kids as university students who think they're God's gift to the world. And you know, they're going to be masters of finance in short order. So that's actually really, you know, kind of, I got used to finding these alternative paths because I didn't have the kind of traditional qualifications. And when I was at RBC, I got connected to some great mentors just because I was open to reaching out and being like, "Hey, love to have a coffee. You know, here's some questions I'd love to ask you." Got really good at writing down what people would ask. I built all these tools to engage, follow up. I'd always give people, like, as you can see, there's lots of books on it. I'd always give people a book as a gift and like write a note in it. So lots of ways to endear people to want to mentor you, which works especially well when you're young. You know, no one's excited about mentoring the young 35-something, but everyone's excited about the young 25. So that was a huge reason why we got ahead. And we could talk about how that impacted, you know, the business from a cap table perspective and, you know, why it really matters in B2B. And then on the entrepreneurial side, it's really funny because, yeah, as you mentioned, Ted started Kik, you know, obviously huge consumer company. You know, I started StreetContact, very enterprise-focused. My brother, you know, chose not to go down the entrepreneurial path and he's a pediatric surgeon. And, you know, people like that.

A bunch of underachievers.

Yeah. Yeah. They're like, what was in the water? So I think, I think one of the big things is, you know, we very much grew up being forced to solve our own problems. Uh, we had a very disabled younger brother. His name was Jack. He passed away when he was 21. But it meant that basically my dad worked to pay the bills and my mom took care of our younger brother and then everything else was free for all. So it's, if you want to do something, you got to go do it on your own. And you know, now having 3 kids on my own with a 4th on the way, I think a lot about how do you create that independence and that ability to kind of go and figure it out yourself. But I also think the nice thing for us is we've always all been, you know, optimists to a degree of not being afraid to lose something and instead focused on what we can do and what we can, what we can go and build. But one of the fascinating things is when I went to work for RBC, I had no intention of starting a company. I look at my goals from back then, it was like, you know, be the youngest managing director, do this, do that, all finance-related stuff. But I think for me, and I'm sure you hear this with others, I just had the itch to fix a problem in the industry I loved, and that catalyzed this problem that turns into a bigger problem that turns into a bigger problem, and you kind of go down, you know, the rabbit hole, as it were, and then you find yourself in the world of Oz.

I love that. First, hearing you tell that story, I was literally picturing the movie. It's like such a narrative for a movie, right? This kind of underachieving kid didn't go to Harvard or Stanford, doesn't have like the secret handshake, doesn't come from a rich family, hustles his way in and like makes it to the top. Like you didn't keep going in that industry, you pivoted it out, but like Anyway, there was like a, there was like a movie narrative in there as you were describing it. I guess literally picturing it.

Yeah, I want to be honest that I didn't grow up in a hard-to-do household. Like, I definitely had lots of—

Oh, that's fine. I'm, I'm just, I'm, I'm embellishing the story for dramatic purposes.

100%. You sell the rights to Netflix, they'll be all over that.

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Yeah, it's a good question. I think number one, you know, one of the things growing up is my dad is the quintessential salesperson. I'd say, you know, he's most comfortable when he's schmoozing. I'd say he's actually maybe uncomfortable when he is not schmoozing. And one of the things he did early on, which was great, is he would like set up lunches for us. 'Cause you know, we'd be downtown. He's like, oh, I'm having lunch with this person. You should come join. And that kind of started the habit of, you know, meeting people, talking casually, kind of building a little bit of that structure. The first time it really hit me was, you know, how co-op works at Laurier is you start in your second summer. So the kind of ball hit me where when you apply for co-op, what co-op employers tend to do 98% of the time is just cut under a certain GPA. And so I realized I was applying, I was just getting rejected left, right, and center.. And then that was my first experience of, okay, I'm gonna put together something well structured. I'm gonna reach out to the employers directly, which is actually technically against the rules, but c'est la vie. And I'm gonna try to distinguish myself from, you know, one in a million resumes. So I think it just started to build out of necessity. But then I realized, because the interesting thing is I talked to people. I remember meeting with this guy for coffee. He was in the Laurier Alumni Network, you know, the super exclusive Laurier Alumni Network. And I asked him, and I was like, you know, when did you, Put your details in. He was like, ah, probably like 5, 10 years ago. I'm like, oh, you must get bothered a lot. He was a very senior guy, I think at TD. He's like, honestly, you're the first person to reach out to me. And that's when I was like, yeah, no, no one. And I think this is something I've come to appreciate. Humans love certainty and people steer clear of uncertainty because it makes them uncomfortable. So getting good marks, clicking apply, uploading your resume and hoping for the best, that is the path people are trained to follow. Versus, you know, the uncertainty of, hey, what if I meet with this person for coffee? What if I reach out? Like, what if they say no? It's just like, you know, fear of rejection, fear of uncertainty, fear of all these different things wrapped into one ball.

So that optimistic foundation is clearly what enabled you to do that.

Yeah, it's funny, one of the things people always ask me though, having, you know, been through the journey, uh, is, you know, what do you think it requires to succeed as a founder? And one of the core things I believe in is delusional optimism, right? You have to be irrational to kind of play the odds. And I think that's actually the hardest thing now as I think about starting a second company is I don't have the delusional optimism. I have all these other benefits. I've done it before, built, you know, et cetera, scaled, know how to manage a team and a leadership team and go-to-market and product, all these fun things. But I no longer am delusionally optimistic. Like I know what the climb looks like.

Mm-hmm. Yeah. Okay. We're gonna, we're gonna have to come back to that. But maybe to set the context for that, no pun intended, let's talk about Street Context. So maybe let's set the stage, tell folks what it did, and, and then let's, let's walk through the journey.

Yeah. So investment banks, for anyone, you know, unfortunately not, you know, deep in the investment bank lore, fundamentally do two things. They help clients decide what to do and then they help them execute on it. Right. So on the traditional investment banking side, that might be going public. So they help you decide to go public and then they help you actually go public. On the secondary side, which is the side I worked on, which is, for instance, trading stocks, they help clients decide what to buy and then they help them buy it.

Right.

The help them buy it side has massively advanced over the last 25, 30 years. Right. We went from funny hand signals and pits about like, you know, how much you're going to buy and touching your head and wrist and all this stuff to electronic execution, which trades in microseconds. Right, but on the communication side, helping clients decide what to buy, you know, it's still to this day a lot of someone writes something up, distributes it via email, via fax, you know, via portal. They blast all this content into the ether, and then they start calling clients to talk to them about it, or clients call them, right? So as a research analyst or a desk strategist or a trader, you might put together a piece on, you know, Netflix and Warner Brothers merger being discussed or acquisition. You send that out via email to your clients. You might then start calling a few people you know are interested. And that's what I did as a strategist. I just blasted content into the ether and content could be research, corporate access invites, desk commentary, sales commentary. And this is true for every asset class and it runs everywhere in the world the same way, whether you're in Japan, you know, the United States, Europe, doesn't matter. And I remember going to my boss one day and I was like, listen, I spent hours writing this stuff and you pay me a lot of money, hence this costs you a lot of money. Who reads this? And the response was, we have no idea. And, you know, that kind of started this interesting problem. And I always tell people, and obviously hindsight is 20/20, it's much better to start with a problem than an idea, right? I think the benefit of working in capital markets, yeah, I got exposed to lots of problems and usually problems lead to more and bigger problems, right? So the first problem was, is I have no idea who reads this and I can solve that problem by saying who reads it. Now I can use that data to better service those clients. So the second problem is we're not using readership data to actually inform how we serve clients. And so these problems start to cascade and obviously, you know, was not so quick to realize this cascade of problems. It took years, but that really started us down the path of, hey, we're going to help you distribute. And I remember our first client was literally like, I just want to know who opens my stuff. He was like, I just do this every day. I've been doing every day for 15 years. Never stop to ask who opens it. And that started this cascade of now we can see who engages. And we essentially ended up building sales enablement for capital markets, right? To help you understand distribution, contact management, list management, follow-up actions, reporting, client insights, management insights. And so we got up to the point where we were publishing content on behalf of 150 broker-dealers. We worked with every Canadian bank, most of the US banks. We had clients in 50 countries, I want to say. So every major financial center, most of the Japanese banks, Hong Kong, Europe. And the nice thing is, you know, while capital markets in itself is kind of a niche, it's a niche that needs to be sold to. So once you get in, you know, the challenge that is sales cycles in enterprise is also your advantage once you're on the other side of the sales cycle, because it's a challenge for everyone else. So that kind of took us to building and launching, and it took, you know, 10 times as long as I thought it would. It, you know, was 10 times harder than I thought it would be, even though I thought it would be harder. And that took us to kind of product-market fit. But the fascinating thing for us is we started in 2012, the company was incorporated. This was before cloud, right? You know, cloud wasn't a thing in 2012. And I remember one of our early clients in 2014 was like, listen, if you have an on-prem version, We'll buy that like today, but cloud is scary. And it took us so long to get going. You know, we only got to, uh, you know, a couple million bucks in ARR by the start of 2020, and then we exited the business, we were in the double digits of ARR by end of 2024, right? So we— wow, kind of, you know, they say lemons ripen early, very slow until it's very fast.

I'm not surprised. A little Piece of useless trivia. So I was introduced to a founder named Jack Newton. That name might ring a bell. Founder of Clio. Back in 2008, Christophe Jans introduced me, wanted to see if I would co-invest with him. And, uh, I didn't because, um, I was worried about this exact thing. It was like, lawyers aren't going to trust having client documents on the cloud. Like, forget it. Like, and he didn't want to do on-prem. I was totally wrong. That's the biggest name in my anti-portfolio, but I totally get it for certainly for a regulated industry as well, right?

Yeah. I remember talking to one of our largest clients, which is one of the top 5 US investment banks, thus one of the top 5 global investment banks. And they said, they're like, listen, we don't use any product that's been in market for less than 3 years. And then usually our sales cycle is 2 years. So you have to get to the point where they want to use it, right? And then you have to sell them. So like you're not closing that client probably anytime before 7 years in market, right? And so it just takes time. And their whole thing is whatever you think we're paying for your software, double to triple it to add in all the soft costs on our end, right? And then there's political risk and social risk and, you know, what if this doesn't work well? And to your point, there's data sensitivity risk, you know, The fascinating thing for us at StreetContext is we were actually quietly the biggest distributor of email in capital markets in the world at the end, right? We were probably sending 4 billion emails on behalf of some of the biggest investment banks in the world, and they gave us permission to send as them, right? So there's a huge level of client trust where, you know, we're essentially the biggest white-labeled information provider to the biggest financial institutions in the world, right? You, you just think about that. You have 150 global financial institutions, probably all of which are on the, you know, sys, uh, systematically important or systemically important list. Just the, the magnitude of that. That's why it just takes a long time to build social capital and build rapport.

No, I totally appreciate that. And the— I'm still surprised no one tried this. Maybe people did, but like, when I think of this market, sure, it's defined, but like, it's rich. Like, they can pay. Yeah, like, yeah, very, very attractive market, you know.

Well, I think this is the fascinating thing about enterprise verticals in general, and I think the more enterprise the vertical, the more true it is. Right? If you look at the difficulty of different verticals, finance will probably only be next to maybe healthcare and maybe the government, right? It might actually be harder than the government, but maybe in line with healthcare. But the interesting thing is that for the horizontal providers, it makes no financial sense to sell to a challenging vertical. I remember talking to an enterprise rep at Salesforce, so they would sell CRM, which we were kind of tangentially related to, and we'd integrate into CRMs. And I was fascinated that more firms didn't use Salesforce. A lot of them had, you know, off-the-shelf— sorry, in-house-built solutions, not off-the-shelf, didn't buy Salesforce, etc., even though other parts of their firm use Salesforce. And the issue that rep, he was like, listen, I can sell 10 times the number of seats to a CPG firm, 10 times easier, and thus make multiples more on a commission basis than grinding it out to sell to an investment bank over multiple years for a small, relatively small deal size. And it's just so hard to sell to some of these industries. I don't know if you've ever watched Lawrence of Arabia, but the whole movie is premised around this taking of Aqaba, and it's this town on the water that's really important, and behind it is a desert, and it's called the Devil's Anvil, if I remember. And essentially, there's no defenses facing the desert because there's no way any army could cross the desert. And the whole story of Lawrence of Arabia is him working with the tribes in the area to actually cross the desert and take the city because there's no artillery weapons facing into the desert. And I think this is the whole thing. It's because it's perceived to be so hard, no one does it, but because no one does it means if you can do it, you have a huge advantage.

Yeah. Yeah. Yeah. I love, by the way, that you talked about crossing the desert, cuz that's literally where I was gonna go next. Kind of like from 2012 to 2020, you were effectively crossing the desert.

Yeah.

How did you maintain that delusional optimism?

Yeah.

And hope and like, did you have investors along the way and how did they maintain hope or were they just, yeah, telling you to put a bullet in it? Yeah. Like, I don't know, tell us about that 8-year period crossing the desert.

Yeah, it's, it's really funny cuz I think the, you know, the, the pivot moment for my personal career was in 2018 because it, and, and I'll get to why, but 2018 was kind of this crucial moment, so. Leading up to 2018, I would say I was very good at raising money and very bad at running a company. And it's a funny trade-off being very good at raising money and being very bad at running a company because you get better and better and better at the wrong things because what you think will make things better is actually raising more money. Right? And, you know, the challenge with raising money is you're really trained to talk about these kind of key moments. Which might seem important but actually aren't important, right? And it prioritizes the anecdote and deprioritizes the systematic structure. So what happened was we kind of started getting our first traction in 2014. We got our first customer at a big US investment bank called Jefferies. We had only Canadian customers before that. They're a tier 1 financial institution. And that was really the, like, the moment of, like, let's go. And I remember I actually got invited down to a breakfast in Waterloo with a big venture fund who ended up becoming one of our bigger investors. And, you know, after the breakfast, they were going somewhere and I was like, oh, can I get a ride? I was like, yeah. So I parked my car and I actually just like jumped in their limo and I actually was going the other direction in reality, but I just used it for like another 30 seconds to pitch.

And so much hustle.

That's so good. And again, it's like, you know, this whole idea of like doing the unorthodox or the kind of like socially unacceptable. So, you know, I,, you know, got really good and then that created momentum. And, you know, I remember getting coaching from people on how to raise money. It's fear, it is greed, and how do you bring people in? And then we kind of were able to build around that momentum. So we did a Series A in 2015, we raised $8 million US, and then we actually did a strategic convertible note after that. And for another $8 million US in 2016 and '17, so 4 and 4. So we had $16 million US coming to the company. And one of my greatest axioms from that time in the company's life is that strategy should never be driven by capital.

Right?

When capital drives strategy, your business is, to put it politely, like fucked because you will not do the things you should do. You'll do anything that you can because you have money to do it, right? What you really want is you want strategy to drive capital needs, right? When you say, here are the things we want to do, how much money do those things cost? So because we had so much money in the bank, we went from building one business to trying to build three businesses at a time because we were essentially building the sell-side distribution, the sales enablement, then also building the buy side and also trying to build a marketplace in the middle. And the encouragement we were getting was, you know, go big, go big, go big, go big. And, you know, you have the capital, spend the capital. And we were able to also generate a ton of interest and excitement. You know, we brought on the founder or the venture arm, I should say, of Point72 as an investor, the venture arm of Power that became Ciguard as an investor. We brought on the CEO of Morgan Stanley. We brought on the CEO of Thomson Reuters. We brought on all these great investors because we had so much perceived momentum. Meanwhile, the cost line, the revenue line, we're just wedging in the wrong way. Right. And it was about 2017, 2018. We had a board meeting and it was getting very uncomfortable. I mean, I'm a big believer in transparency, so we were burning probably $500,000 to $700,000 a month. At that point. And it wasn't like we were a company doing $10 million in top line, you know, growing 1,000%, burning $500,000 to $700,000. It was, we were an enterprise company burning because we were just trying to build 3 things. And I remember at a board meeting, I was like, listen, I think like we need to reduce the size here. Like even me, the naive, at that point I called myself founder of the company, the naive founder, I was like, this is uncomfortable. Like we're just clipping through cash. And I remember one of our board members, I'll never forget, was like, listen,, you know, if you get acquihired, they tend to actually pay per engineer. So if you fire a bunch of engineers, you might actually get acquihired for less. And then I remember being like, oh my gosh, there's a fundamental kind of difference here where I am one of a portfolio. I'm one of N for you, but I'm one of one for me. And that was really the pivot point where we laid off 40% of the company. Uh, you know, we downsized dramatically. And I think we went from 55 people to 26 people, you know, in the course of a small amount of time. And we went back to just focusing on one business. So the fascinating thing is we raised probably close to $20 million up to that point, and it got us to a couple million bucks in ARR. And then we only raised another $2.5, $3 million after that point at various small little inflections. And, you know, we delivered multiples of ARR. And I think just capital is this curse, but that was the point where I switched from founder to CEO where it was, hey, this is my company, this is my destiny. I need to take control. I need to focus on building because I did a lot of the things before that, that first-time founders do. I thought I could build people instead of buying them. You know, I was focused on like, you know, the family, you know, everyone, you know, is, is emotionally important. I focused on the fact that, you know, we rule through democracy. Let's all have conversations about every decision. You know, you pick all the things that people do wrong the first time around. I did them all. And then I went through a big pivot where it was, this is not a democracy. I was still hyper-transparent, but, you know, we make the important decisions centrally and then everything's open to being challenged, but it can be focused on building a really strong leadership team. Focused on building and bringing in, you know, experienced execs. And that was really the point where, you know, I had to fire 40% of people. Was it— was a very kind of forging experience. And I remember for sure talking to someone who, uh, and one of our investors— I'll give Inovia a lot of credit— they introduced me to someone through this, and it was like, hey, you know, talk to this guy, he just did a layoff too, you know, he'll give you some good feedback. And I remember him saying, he was just like, it'll be the most traumatic thing you do beforehand, but the most relieving thing you do after. Because now you can actually save the company, right? You know, it is true, you know, battlefield triage. No one wants to do a layoff, but sometimes you have to.

I love it. I'm curious, and if you don't want to share, that's fine, but like, did you have board control then? Because I would imagine your investors didn't want you to do that.

Yeah, it was actually a really key thing. I remember, and I, and I give all the credit here, uh, to my brother because he obviously was 5 to 10 years ahead of me in the journey. And I remember him telling me at one point, you have to choose whether you want to optimize control or economics when you're building a company, right? And the reality is, is everyone is friends until money is involved, right? Because as an investor, their list of priorities is number one, make money, because that's their fiduciary responsibility. Number two, support the founder as long as it does not interfere with number one, uh, correct, right? And One of the things we set up really early on, and I give, you know, ABC a lot of credit for this, is they were very amicable and very founder-friendly because obviously a lot of the team there have been founders themselves. So one of the things with our Series A was, you know, I wanted to say, listen, we'll have a 5-person board. I'll be one of them. And it was actually hardcoded. So it wasn't the CEO, it was Blair Livingston, our lead investor, uh, which was ABC. You'll have one and then 3 independents, which I personally nominate. And the whole thing there wasn't, you know, the board will agree or some kind of voting or blah, blah, blah. And then I had a superclass of shares on top underneath for any shareholder-wide votes. So they still had their protected preference vote. I couldn't sell below the last valuation. I couldn't do anything funny. But essentially, you know, I had total control over the direction of the company because I had, you know, 4 out of the 5 board seats. Plus I voted something like 91% of the shares and I had all the seed investors put their shares in a voting trust. So I had all that as well. So it became into a good point where we could have the most transparent board conversations because I didn't have to worry about guarding my words for fear of, you know, potentially being removed.

I love that. Untouchable. So good. That's amazing. That's such a powerful lesson for like, if people walk away from this conversation with nothing but that, yeah, gold.

Yeah. And the best thing about it is there's no rational way that an investor can push back without being transparent, right?

Right.

And listen, listen, the great thing was APC, to their credit, they said, we've been doing this a long time. We have never had a good outcome where the founder was forcibly replaced. So, you know, they just looked at the data and they said, it's not in our interest. But if you're a founder and you are raising money and you say, this is important to me, number one, there was no reasonable pushback that isn't transparent of, no, we want to be able to fire you at some point if we want to. But number two, you do have to appreciate you might have to give up economics. Right? You might not have as— you can get a much better valuation if you give up complete control with a 3x liquidation preference and blah, blah, blah, blah, blah. Right? If you optimize economics, just be wary, you are going to give up control. It's just, it's just a pendulum in the grand scheme.

I love it. Staying on funding for a moment, you know, I've done a few strategic rounds over the years and I always kind of counseled my companies like, let's not even do it until we're like at Series B level because by that point, obviously we're post-product market fit, but most importantly, we know what we want to be when we grow up, and therefore we have durable context about who is actually strategic. And then of course you need to be a certain size to be able to deal with these strategics. But like, you had like a bunch on your cap table early. So like, I guess, how did that happen? And were they all trying to pull you in different directions? Like, well, yeah, what was, what was that all like?

So, so I think it's a really good question. What I would say for enterprise founders out there is that there's a lot of benefit to having strategic industry individuals, but not strategic companies. I think it's very dangerous when you bring in actual organizations who want to invest in the company because it creates a very strange dynamic. What we found a lot of value in is, especially in enterprise sales, one of the most important things is top of funnel. Because it really comes down— if you want to get in to see senior executives, they don't respond to SDRs, they aren't filling out forms on LinkedIn, you know, they aren't doing anything other than taking warm intros through trusted partners. So what we got really good at doing is saying, hey, what's a market, a region, a segment, a geography we're trying to break into? Who are some really interesting individuals and how do we create a partnership with them where it's win-win? Usually that meant bringing them on as an advisor. I would say there is nothing more predatory than 98% of advisors because, you know, they come, they have a bunch of coffees, you give them a quarter point in the company, and then they disappear into the ether. So what we actually did is we build an advisor bench and we would put them on a 2-year vest with a 6-month cliff, and then we'd actually give them KPIs and we'd hold them accountable. And I had no problem firing an advisor. The other thing I would say that is very powerful early on for enterprise companies that we did, which was a huge benefit, is you're playing this game where you're trying to appear bigger than you are, right? You're trying to reduce concern and get people to focus on upside potential. So we had this funny anecdote early on, you know, we were selling to, I believe it was RBC. I'd obviously worked there, presented to them, we're going through the due diligence process, and I had listed my office as my parents' house 'cause I was working in my parents' basement in classical startup world. The info security team actually Google Maps the office And they're like, this is a house in like a residential neighborhood. So they go on a call with me and they're like, hey, we looked up your office. Like, it appears to be a home. Like, how big is this company? Like, how real is this company? And that was my first and hopefully last lesson in managing optics. So I don't encourage anyone to lie, but I encourage everyone to manage optics as best you can. So I remember when we were probably only a 4 or 5 person company, we had a 6 or 7 person advisory board. So we put the advisors on the website, but no employee details on the website, because surely if a company has 6 or 7 advisors, it must be— the company must be bigger than the advisory board.

Yes, that's right.

But it absolutely helped because I remember, you know, when, when we would go see certain firms, the advisor would actually come or they'd make the warm intro and it just totally changes the dynamic. You go in more senior, you get instant capital in terms of social capital. And you can just move much faster.

Mm-hmm. All of this is just examples of hustle, right? Like the genesis of all of your moves here is, is hustle. Like, I don't know. Yeah. That feels like the theme. Yeah.

Well, and it's actually, it's very interesting that you bring that up because it was like kind of around year 8 or 10.

Yeah.

I was starting to get tired and I was like, oh man, I've been going at this a long time. You know, I never thought it would take so long to build something of any material size, but yeah, lo and behold, it does for the majority of people. And we had our first private equity firm reach out to us and they, hey, we love your business. You know, we just bought this thing. We think your thing plus this thing could make a ton of sense. And we actually got to the point where we signed an LOI. This was in 2023 because it was a tier 1 private equity firm, very well known. Negotiate LOI. It wasn't great, but, you know, everyone was going to make money. And this is where I started to learn about the hair of private equity deals because it was going to be You know, here's the headline price, but it's 60% cash, 40% stock, blah, blah, blah, blah, blah. And I remember in the 11th hour they called me and were like, hey, financing issues, we got to drop the price 20%. But what they did is they're like, we'll set up an executive compensation pool so you actually won't make less money. You'll actually make more money if you take this deal.

And I remember just being like, bad ethics. That was an ethical test.

Yeah, 100%. And I mean, it's super frustrating because you still have to smile and nod when you're telling them like, thanks, but no thanks. But like, stay in touch for sure. And you know, we spent, and these were in our leaner years where we were running leaner. So we spent $300 grand on legal fees. Yeah, we, oh man. Yeah. You know, we were already on the SBA. It was already like, and it was just awful. But you know, I'm a big believer in providence and running that was basically a dry run in a PE exit. And lo and behold, a year and a half later, we would end up selling to a PE firm. We had already been through the process. I knew all the questions, I knew what to ask, I knew what they, you know, were gonna prioritize, and I had something to compare it to. And you know, what I'll say is for Thoma, the process was fast, it was efficient, it was clear they want to buy the company versus just learning a bunch of stuff. You know, we worked with the senior partners there. It was just, I could tell from context that it was a good process and I knew what mattered to me, right? I knew what mattered in the process, which was clean deal, you know, no crazy earnout, no crazy retention, just making it, you know, a deal to buy the company, not to buy the people. And that journey of going through with the worst ever private equity firm really helped frame the conversation. And it was a much better deal. You know, I thank God every day that that first deal did not go through.

I'll tell you, I deeply believe that everything in life happens for you, not to you. I go back, it doesn't always feel that way in the moment, but when you look back afterwards, you always see it. And like, when you told me about the independence that you had to have early because of that younger brother, that was for you, right? That was a feature, not a bug. It created who you are. This process, this failed process and the $300K of fees that you just set on fire. Yeah, also for you, you know, even though it probably was super frustrating in the moment.

Well, and the fascinating thing is you talk about hustle. I found out later from that first PE firm, they actually specifically target companies that are 8 to 10 years old where the founder is getting tired, right? Because they know there's this window where, you know, you've kind of been through a couple life cycles of the company. You're getting a little tired. You're probably a little burnt out, but the company is stable now. But I do think once you escape that critical momentum, you know, there's a Jason Lemkin quote, which I love, which is, I think it's zero to 100,000 impossible, 100,000 to a million unlikely, you know, a million to 10 million, you know, I mean, I'm butchering it, but like uncertain. And then like 10 million to 100 million unstoppable. And it's just like this whole idea, like as you go, it actually gets easier because it's like a rocket lifting off, right? You know, you first have to break the pull of gravity and then you go, go, go. I think one of the challenges was, is, you know, we could talk about the post-exit life because I think people don't appreciate how jarring it really is. You know, you've been doing something for 12 years, 10 years, 8 years, whatever it is, and all of a sudden you're not doing it anymore. You know, it's all I stayed to help with the transition. You know, until later this year, sorry, just earlier this year. And, you know, I was a big believer in what they're doing in the industrial logic and I still am. It's just not being CEO is really hard and you have all these opinions and ideas and you're used to being able to just get things done, solve this, solve that, where you have free rein over the entire company, right? There's no one not under your purview. And then all of a sudden that's not the case. So I think the challenge is people think retirement is going to be great, but I can tell you, and you probably know this, is there's nothing more unfulfilling than retirement. After a few weeks, which is great, social interaction goes like this, mental stimulation goes like this, purpose goes like this. And I think after a very brief time, you realize that you want to be doing something. Now the challenge is I do look back and I've read lots of what they call post-entrepreneur, you know, uh, essays and, and stories. And almost everyone has some form of, I wish I didn't sign it, even though I was this one who signed the LOI, right? My board basically gave me the decision of, do you want to do this? Do you not want to do this? Now, it ended up being the right decision for our shareholders. I think basically every one of our shareholders ended up making like a 20% IRR. So, you know, they're not going to blow it out, but great, all cash, you know, especially over 10 years for our seed investors. It's a, you know, it's a solid rate of return. I mean, crushed the, uh, the TSX. But there's definitely parts of me that wonder, like, should I have kept going? And the problem was, is because I had raised money, and a significant amount of money, it wasn't really my company anymore, right? Like, I would have to recap people. I would have had to bring in a new investor. Like, we didn't have the cash flow to do some big buyback or something like that. And so as I look at kind of doing the next journey, it really does frame my perspective of Do you really want to build a— I'm torn between, I've already hit my single or double, right? So I don't need to survive anymore. So I either want to go for that home run and just swing for the fences, or I want to build an enduring business that I can maintain 100% control of forever. And I think I've ossified into those two or bifurcated into those two paths. And it gives you a lot of time to pause and reflect and say, Listen, some companies, some companies aren't venture fundable, but some companies are only venture fundable.

Right.

And it gives you a lot of space to think.

Yeah, man, we could spend the entire podcast. If this was minute one, we could have spent 59 minutes on that. Right? Like, yeah. One of the reasons why I became a coach is because there was a huge coaching component to selling companies. You can't A/B test the decision. There's no right or wrong answer. It's an emotional rollercoaster. And everything you said afterwards, like for better or worse, like founder's identity is tied up in the company. They lose their sense of self. Uh, I don't know how, uh, I've personally done a billion dollars worth of exits and some meaningful percentage of those founders, even where they had a great outcome, regret it afterwards.

Yep.

And almost everyone assumed it'll be easier next time. I'm such a better operator. I've been through all this scale. I have this network. I have these leaders who follow me. I've got investors because I had a track record. But each time is unique. Each outcome is so much dependent on luck and timing, which is out of your control.

100%.

100%. You know, so it's not easier the second time.

Yeah. Well, you, you cue so many thoughts, uh, just on that, those comments, because I mean, You know, number one, I think I'm a big fan of the Thomas Sowell quote, which is, "There's no solution, just trade-offs." And I think that speaks to every time you start a company, there's no optimal way to start a company, time to start a company in your life, et cetera. There's just trade-offs of when you start, right? When I started Street Context, I was 22, zero responsibility, all time, but unfocused, you know, like a bull in a china shop running around smashing things and it's chaotic. And I, was not really balanced or productive or all these things in many ways. Now I have kids and I'm married and I have a house and I have responsibilities and all these other things. And I have financial security, which also creates its own challenges, right? There's a great Succession line, which is $10 million is too little to be rich and too much to be poor. And there's a little bit of that, which is once you've made a little bit of money, it's very hard to push yourself to the limit. And I actually think that's one of the big challenges. And that's why I give founders who go all in all over and over and over so much credit because I can't even comprehend that, right? Just this ability to keep going. But one of the other great lessons, because you spoke about, you know, companies selling and getting advice and all these things. One of my biggest insights is never take advice from people who have not done the thing you are trying to do. The amount of people who give founders building company advice who have never built a successful company is astounding, right? You don't see in any other industry, you don't see people walking around telling you how to do surgery who aren't doctors, right? Right.

That's true.

My whole thing is I think there's some people, I, you know, I like to say there's some people who did the equivalent of going to West Point, so they learned how to shoot the gun. And there's some people who have been to war and they know what it's like when the people shoot back. And you only want the people who have been to war. I think that has been one of the most important things this whole journey, right? To the whole point of selling your company, the thing that was really helpful is we talked to other people who had sold their company, sold companies, et cetera, right? You know, talking to someone who just because they work in investment banking and they do $40 billion mega mergers, they have no idea at this level. Yeah. The nuances. Yeah. And, and I think just if I could give anyone else some insight, it's just at every stage you're at and every problem you're trying to solve, When you're building a company, the only nuances of your company, even though everyone thinks their company's a special snowflake, is the people who work with you and the product you're building. Everything else is wax on, wax off. And it's just reaching out to people who have done the thing you're trying to do and getting feedback, getting advice, right? Like if I was selling a company, reaching out to someone like you would be great because it's like, hey, what, what are the common pitfalls? Like what should I be worried about? What should I, you know, get excited about? What should I optimize for? What are the trade-offs? You know, I remember someone explained to me like, oh, they're going to try to get you on working capital adjustments. I was like, what is a working capital adjustment? And it's just all these nuances of what really matters. And I think that was a great— and the nicest thing for us is we had a guy on our board, a guy named Andrew Tai, who's also a great Canadian entrepreneur, and he actually sold his company to Thoma Bravo. So he knew kind of what was happening and what the playbook looked like and what was real and what wasn't. So just as much as possible, surrounding yourself with people who have been there and done that is just a massive, massive advantage.

I love it. I really do. I, um, would love to, as we begin to kind of wrap up, go back to that hypergrowth period, right? We've crossed the desert. Now things are going, and I'm wondering if you could talk about, other than kind of hanging on for dear life, what you did to be able to grow faster than your business. And in that, could you also touch on the role that peer group, your peer group played? When I first met you in person, it was with your peer group. And all of my CEOs have one, a formal or informal. So I'm wondering if that played a role as well.

Yeah. So I think there's a couple of different things. Number one, you know, I always like the adage that every time your company, your company doubles, everything breaks. So it's like 0 to 100,000, 100,000 to 1 million, 1 million to 2.5, then 2.5 to 5 to 10 on. All the systems you've built, all the processes you've built. And that's what makes startups hard is because you're growing so fast, you double so fast, things break so fast. And I think it's the acknowledgment that every time things double, you should, number one, expect things to break and going into it expecting that, not saying, well, this system works well enough, let's just keep trying. But some tactical things we did. Number one, as you can see behind me, I'm a huge fan of biographies. I think the majority of business books are absolute trash, but biographies are great, right? So just find all the biographies. You can start with the startup stories. You know, you can start with individuals you like, you go back in history, but the more stories you read, number one, you appreciate deep down it's always chaos everywhere. Everyone almost always dies.. And you know, you get through it through a combination of grit, skill, and luck, right? So I think reading startup stories was a huge asset for me, and which is kind of almost like to use what you were saying of surrounding yourself with peers. Those are like unidirectional peers, right? You learn from them, but it's not a, you know, a two-way conversation, right?

It's a mentorship.

Exactly.

Yeah.

You get to learn through their stories. Then, uh, at the second level, you know, I was very fortunate. One Eleven actually launched a, series of forums modeled after YPO. I think this was back in 2015 and I got included in one of them and ironically it's the only one that actually still exists. And we're here 10, 11 years later. So it's myself, 7 or 8 other founders. We meet monthly. It's become like a great, it's funny, it started all business and from the start it's kind of expanded into business, family, and personal as well. And it models after YPO, so that's not our creation, but having a group of people that you can learn from, bounce ideas off, get feedback from, that are genuinely only interested in supporting you, I think is very important. I think one of the challenges is around the table everyone has an agenda when you're building a company. Your investors, your leadership team, your advisors, everyone has an angle. With our community in this small group of forum, it was great because no one had an angle and it was really transparent. And I've seen some people try to replicate this within, you know, their portfolio, et cetera. But I'd say is that transparency takes years of high-volume, regular commitment and can't be built in a weekend or a week or once a year. And that's been huge because I get to see what other people are going through. I can see their challenges, I can reach out to them, I can see what they're learning. You know, a significant portion of our group has gone through Y Combinator and, and learned all about that. So you really get all this best in breed and you build deep trust with people who are also professional executors And I had one of the guys from that group actually on my board when we sold StreetContext. So it actually really kind of does become quite intertwined. And then the biggest thing is I really focused the shift from, hey, I want everyone in the company to be great and I want everyone to be involved and I want everyone to be contributing to decisions, to I want the best leadership team possible. And that was a big transition. And it's funny, you know, I had a brief stint at coaching myself and I found it challenging because I'm, you know, CEO and I'm like, okay, just get out of the way. This is what we're going to do. Uh, but one of the biggest commonalities I saw is people had a very lackluster approach to the leadership team in terms of how do you meet, how do you coordinate, how do you spend time together? What's your cadence monthly, quarterly, annually? You know, so we would have a planning session onsite once a month, then quarterly we'd have an offsite and annually didn't really matter because we were doing offsite every quarter. So we treated a quarter basically as a year. Sometimes we would do 2-quarter projects. We talk about what was business as usual. We talk about strategic priorities and we really got proficient in using that strategic priority focus to eliminate all other priorities, right? You know, when I go in and meet with founders, even if it's just for a coffee, I'm like, what's your biggest priority right now? They list off 15 things and I tell 'em like, you don't have any priorities then, right? You know, it's like the man who chases 2 rabbits catches none. And I think the biggest thing we got really good at over that period is really disciplined about focusing on the business. We, you know, had a great leadership team. We also brought on a great fractional CFO named Steve Wilson. And—

oh yeah, I know Steve.

Yeah. And it's just the discipline of how do you do on a monthly basis, how do you do on a quarterly basis, and then how do you do on a weekly basis and focusing on building that leadership team. And I think the hardest thing for me, and I think for a lot of founders, is you look at a project and you're like, I could get someone else to do it, but I could do it better. So you just end up taking more work on. I think the biggest red flag for almost any founder is if you want to hire an assistant to help scale you. What I usually see is that is a cover for a very weak leadership team, right? If you had a better leadership team, you wouldn't have to scale yourself and you'd have time to do all these other things because you could push responsibilities off of the leadership team. But people say like, no, I need to figure out a way to squeeze out 10 more hours. And you know, I'll do that by like not responding to emails and And I did it myself. But what you realize is it takes a team to build a company, especially once you're out of those early, early stages. And I remember when I was on vacation and our first deal closed, like the experience of, wow, this happened with zero involvement from me.

And now I actually own a business versus I was the business.

Yeah, exactly. Versus I was an employee just doing things. Yeah. Now the business is a self-perpetuating entity and that's a really cool moment. So I think I would say a combination of learning, you know, both from books and people. I would say building habits and cadence, and then just learning best practices from everyone, be it companies. And then the last piece I'd say is just recruiting great people. I would say it was definitely not my forte when I was a founder for most of the time, and I just started picking up as a CEO. Great recruiting means building a stable of people at all times, not only when you're looking for a role. And I got to learn from some great founders who did it so well. You know, they'd meet with someone great and say, who are the 3 best people you've worked with? And they would build this self-perpetuating recruitment machine.

If you're ready, final question. You know, you are, um, I was LinkedIn stalking you before this and you're talking about you're doing a new thing and you're kind of exploring your curiosity and capital markets. So yeah, what's, what's getting you excited? You may not know exactly what you're going to do next, but yeah, what's getting you excited?

Yeah, you know, it's funny. I kind of used a little bit of time off to go through the whole gamut of what I could do next. And I think, listen, all roads eventually lead back to starting another company. And I, you know, I wonder if I'm like, am I just doing this what I'm comfortable with? But that's a whole nother conversation. But a lot of things are happening in finance, and I spent a lot of time thinking about what kind of business I should start. Should I try consumer? Should I try this? Should I try that? And what I've realized is my personal competitive moat is distribution advantage. You know, I've taken the time the last 12 years to know the people, to build social capital, to know you know, who can help get things done. And that, that is a real tool and a real benefit as I kind of think about what's next. The nice thing now is when I was CEO of Street Context, I had to still be guarded about, you know, my true thoughts on the industry and what I thought was going to change. Because once you have clients, you can only say so many incendiary things before they start getting upset.

Yes.

Right. You know, you can't say, hey, lots of egos in that industry. Yeah. And you can't say like, listen, I think your business might be fundamentally destroyed or this part of it might be over the next 5 years. 'Cause then they say, well, guess what? Your business is gonna be destroyed today 'cause you're fired. So you can only be so revolutionary when you're part of the establishment. Now that I'm on the outside looking in, I take a few things. Number one, I wanna take my time choosing what to do. Like Street Context was a great business for so many reasons, but I really leapt then looked and I was like, this is what I wanna do, so I'm gonna do it. And I just grinded it out. Now as I am here, I can take my time to look before I leap. And start small and iterate and then find the thing that ends up being exciting. So I think that's a big difference this time around. Number 2, like I said earlier, I want to find something that potentially is a bigger swing. So I want to look for the right dynamics. I also want to find something that's selling into a growing market, right? We used to sell per seat. And as you might be able to guess, the number of seats on Wall Street is going down. So we were kind of driving up towards a downward sloping angle, which isn't ideal. So I'm trying to figure out what's the use case, what's the problem, what's the challenge. But I think there's lots of really exciting things happening in capital markets right now. Number one, AI is going to be massive, right? Like all the big AI companies have targeted capital markets as an area they want to invest. OpenAI hired 100 investment bankers, you know, Anthropic's doing their thing because so many of the processes are repeated, are ongoing, are predictable, etc. Number 2, I'm— was not a crypto person, but I'm a huge tokenization fan. I think tokenization is fascinating because it kind of disconnects a physical thing with its challenges from the digital piece, right? The tokenization of dollars with stablecoins might be the killer product-market fit use case that crypto has been looking for. It removes price volatility. It does all these interesting things. You know, it makes markets more global. You can move money faster, you can buy things faster, right? I think as a Canadian, I'm like, why would I ever buy GIC again if I could tokenize dollars and buy essentially a T-bill with no friction, right? And then like, what are the knock-on effects of that? What does that mean for people in Malaysia who want to buy shares of Apple, right? You know, what does this mean for moving money? And then on the AI side, it's, you know, what does it mean for creating financial models? I have a good friend at a company called Daloopa. They just built one of the first agentic AI layers. So now you can ask Excel— sorry, agentic Excel layers. You can ask Excel to build models for you and it will just go off and build them and come back when it's done. Right? You as a product guy, I totally appreciate that. Crazy.

I'm all over that.

Right? You know, you have LLMs interacting with content, giving you a totally personalized investment experience. You know, where I used to have to have access to a tier 1 investment bank to get an initiation report on a company. Now I can have ChatGPT build me one, you know, in a couple of minutes. So it just totally changes the access to information, the flow of capital. So between, you know, and I get that I'm kind of at the buzzword nexus right now, but between tokenization and AI, I do think there's huge change coming. And I think the big thing is that change that is step function revolutionary usually comes from the outside in because the inside tends to be more incremental in its change because people don't want to blow up their existing business. They have to maintain their existing business, they have to maintain existing client relationships. So they try to be incremental with how they build new products until the new product comes in from the outside and can really, you know, attack the status quo and build for what's next. So I think that's what I'm really excited about. I, you know, I used to put out thought pieces, like I started as a desk strategist all those years ago, ranting over email. I'm getting back into it now. I actually have my first one going out this week. I've had a ton of people sign up for it. Yeah, I'm excited to get back in the industry. I was at a conference in London a few weeks ago. I was in Miami a couple of weeks after that. There's so much change happening and like all change, you know, the industry will push back, push back, push back and then be swept up in it. I remember when the story of electronic trading coming out, right? Like everyone fought electronic trading. That will never work. People will never trust computers with their orders. It's too complex, blah, blah, blah, blah, blah. Fast forward, you know, No one would ever open outcry. And the last one is I remember the change of ETFs, right? We had this great picture on our wall and it was Vanguard assets under management. And basically for 20 years, the line is barely above the axis and then it just goes, right? And it, the whole point of the picture was like, don't quit too early. Right.

If you quit, it sounds like your revenue arc actually, as you went from 2020 onwards, right?

Yeah. Not quite the Vanguard revenue arc, but it's a good one.

No, no, no. I've seen a graph of this, of LinkedIn's network and how it built over time, and it was the same pattern.

Yeah, totally. And it's so, I think all these things, you know, they come slow and then they come fast. And I think what I'm trying to do right now is be nimble. I want to do my own seed round, maintain 100% control. And with some of these, you know, vibe coding tools, you can really get a first version. Like I think of building V1 of Street Context, I need an entire team versus building V1 of whatever's next. You know, you can do it with a couple people and some great, you know, AI tools. So I think it's really ripe. I, I think there's another fad coming out, which I think might be part of this change, which is like microentrepreneurialism, right? I think the ability for entrepreneurs to build micro businesses, you know, as instead of a side hustle, it's a micro entrepreneur where you can do these really small things and like maybe it's building infrastructure to do that in capital markets and like, what does that look like? Yeah. So anyway, lots of changes coming and I think it's one of those things where I have the opportunity now to take a big swing in an industry I know and love, in an industry that I have social capital in that I can spend to accelerate things. Because sometimes in B2B sales, the hardest thing is just getting the first meeting.

This is fascinating. I, uh, I feel your enthusiasm just as you were talking about it, like you were just leaning forward more. So I can't wait to see what comes out of this. Yeah, really fascinating.

Yeah.

And thank you so much for being on the show. I really, uh, really enjoyed this conversation.

And thanks for having me. And I appreciate you doing this because I think it's these stories that get people encouragement that there is a light at the end of the tunnel. And to anyone out there grinding, it's like, I remember the last thing I'll leave people with is I remember when I sold my company and I signed the final letter, wires came in. I remember I was thinking like, this is like what the end of life is like. You don't realize you're on the journey until the journey ends. And then you have this moment of like, Oh, that was it. Like, that was the journey. And so I encourage anyone who's just in the trenches grinding, like, appreciate, like, this is the journey. And one day that journey will be over, and then all you will have left to do is reminisce about the journey.

Wise words. I love that. Thank you so much, Blair. So good. Hey, thanks for listening to the Startup CEO Show. If you'd like to connect with me, be sure to visit my website at markmacleod.me or follow me on LinkedIn. LinkedIn @TheMarkMacLeod or Twitter @MarkMacLeod_. And if you want to tune in again next week, be sure to subscribe on YouTube, Spotify, Apple, or wherever you get your podcasts. We'll see you next time.