#016: Yacine Sibous - Hypergrowth Lessons from Raising $157M

This is one of my favorite questions asked on the podcast. What do you think are the common traits of high performers?

I think it's important to have a chip on your shoulder. I mean, you obviously need a lot of ambition. So to a point where it's almost delusional, you have to believe that you can create a reality that is different from the one that exists today. And that requires a lot of tenacity, a lot of vision, a lot of ambition. And just you have to be willing to make sacrifices.

Yassin Sebbouh is the co-founder of Parker, a corporate card-focused fintech company targeting e-commerce brands. In 2023, the New York-based startup announced a massive $157 million funding round across both equity and debt to accelerate their impressive growth. In this episode, we cover Yassin's path towards financial independence, lessons learned from Y Combinator's Paul Graham, balancing health and hard work, and the reality of high performers. Welcome back. Today we have Yassin Sebbouh. Co-founder and CEO of Parker joining us. Thanks for joining today, Yaseen.

Yeah, for sure.

Thanks for having me.

So you guys are both asking me like, where do you want to start with this conversation today? And I've been fascinated because I think Yaseen is one of the most introverted people we've had on the podcast today. And he's someone who I just look at, I'm like, this man moves in silence and I never know what's going through his head, but he's built like an absolute behemoth of a business. So like, I want to just unpack your— I want to unpack like your mental models in terms of how you operate, because I feel like you're a man of few words, but your brain is always turning.

Sure.

Am I the only one who feels that way? Am I the only one who feels that way, or do you agree?

It's true. We work with like a lot of teams, and I remember going to your office and you were just the chillest, slowest speaker I've ever talked to. But everything you said, like, was a decision. I specifically remember that interaction. I was like, this is very different than most people I talk to.

He thinks differently, and he's— I think he's very articulate with every single word that comes out of his mouth.

We'll stop gassing you up. Answer. Let's hear it.

What do you guys know? It wasn't even— it wasn't even like a question. I think I just want to understand, like, Um, how you think about, like, as an operator, like, you're very much someone who leads by example. Like, is your co-founder similar in that sense? Are you guys completely opposite?

Um, I would say my co-founder is even more of an inspiration than I am to the team because he, he is the single most disciplined person I've ever met. So my co-founder, like I said, meditates 5 hours a day, is up at between 5 wakes up probably around 5 in the morning every day, does his meditation for a couple hours, goes to the office and works like 5 hours. Yeah. So you'll meditate for a few hours early in the day, a few hours before sleep.

What's like the target of that? Have you talked to him about it? Like, is it so he can be like disciplined?

Well, hold on. Before we, before we dive into the target of that, walk me through a day in your life. Like, what time are you waking up? What are— what does a day look like? Because I want to compare and contrast.

Yeah, so, so yeah, I don't, I don't really think the time at which you wake up makes a difference to your success, like things like that. But usually up around 8, 7:45 to 8:30, that range. Then, uh, you know, I'll go to the gym, get my workout in. For around an hour, then I'll work for a few hours, eat, work some more, and just end my day around like 8, 9, 9 PM.

Are there any non-negotiable daily habits?

Showering, brushing my teeth.

It's a good one.

Usual. No, but I think at this point it's just, I think it's just a matter of doing the, the important work every single day and making sure that you're getting the obvious things done, things done. And, you know, I think it's easy to get caught up in detailed work or things that seem like they matter but don't really.

I feel like, so right before this you were telling me how the team has grown, how you guys are really scaling right now, moving to an office, which you're probably gonna have to expand soon. What are, as the team has grown and now you're managing more people, working directly with really senior leadership, What are the few decisions that you have to get right on a daily basis or weekly basis?

I think at our stage it's less so daily and weekly, it's more— and it's more so about making the right key hires. And for us, the right key hires are executives. So once you bring in the right executives in the business, then you, um, there are many things in the company that start unfolding in a way in which you, you don't have that much control. So the positive here is that if you hire someone who's significantly better than you, then those decisions that are out of your control turn out to be better than the ones you'd make yourself. So I think vetting those people out, um, well in the beginning is important. And so, but on the other hand, if you make the wrong hire, then those decisions will compound over time to bring the business in a direction, direction you don't want. So what's important is spending enough time with those key leadership hires to actually make sure you're well aligned on what you're trying to accomplish.

And how has your hiring process evolved from like your early days of your first few hires now to making like very expensive, like leadership hires?

I think one is in the beginning, we wouldn't make the KPIs. So it's sort of, we wouldn't make it clear what our expectations were out of the person. So we wouldn't sit down and like think through, hey, these are all the things we want this person to accomplish in the year and this is their mandate. We'd kind of have, you know, just be like, oh, we need an engineer and then we'd hire a couple engineers and then make the hire. But we didn't have the right test, we didn't have the right, it was just, you know, it was just based on gut and we were moving quickly and just were hiring people that we knew. As we brought on executives, they've actually shown us how to build the right processes. So I'd say right now, step 1 is make it very clear what you want out of the candidate, which is something that you have in the job description. And I think the other thing too is we have our own internal vetting processes. So, you know, like let's say we're hiring, I don't know, give me a role like a product manager, right? So we have like very clear tests that test for all the attributes we'd want to see in a product manager. And one thing that's interesting is the processes are so good that we could identify talent that you wouldn't, you know, you wouldn't necessarily think that person's very talented from the resume, right? So, you know, like usually I think before we'd look at a resume and say, oh, well, this person will work at XYZ company, but that doesn't necessarily mean that they have the skills you need.

How do you vet for work ethic? Speed of deliverables or speed of shipping?

We test for that in case studies, so that's how it comes off. So for example, recently we were interviewing for CFO, and so one of the things we did is we gave the CFO candidate a 90-minute case study that they'd have to do, and that's a proxy for how quickly they'll work. We also believe that how you do one thing is how you do everything. So if you You know, if you're slow on that, it's likely that you'll be slow on other things. And then also just from interactions with someone, you could kind of vet out how they, they think about things. But I think for that, the best way to tell is at the reference stage, and you can ask questions on reference calls that'll sort of give you a sign of whether the person's a slow worker or fast worker.

What are the traits that are most important to you in every individual that you bring on to Parker?

Number one is always initiative. It's very difficult to work with— at a startup, to work with people who don't have initiative and require to be, um, managed a lot or told what to do. So we want people who are very proactive on, like, discovering what the priorities are and then getting up to speed and just getting work done. That's number one. It sounds obvious, but there are a lot of people who once they're hired, they'll just sit there and wait to be told what to do and not do anything otherwise. So I think initiative is very, very important. Second thing is how easy the person is to work with. So there are people who are just very talented, but they're not great collaborators. Why? Because they tend to be very attached to their ideas. You know, they're not— I think oftentimes it's an open mindedness thing or like a flexibility of mind thing where they just, they're not very receptive of other people's ideas or other people's ways of working. So yeah, we try to keep it simple. I think those are the two most important things.

How did you have to change as a founder and as an operator from like the 12, 10, 12 person phase, which I think we're both in right now? So this is like a very top of mind question for me. And moving to what you guys are almost like 35, 40 people, like how have you had to change as an operator? What have you had to stop doing that maybe was like a bad habit that worked when you were 10 people that just doesn't cut it anymore?

I think it goes back to the executive thing where you have to trust your executive that they'll manage their teams. So one thing you have to learn is as a founder, it's very tempting to try to kind of just tell people exactly what they need to be doing. But you can— what you say holds a lot of weight. So you can easily fuck shit up by just going to someone and saying like, hey, I think this and that. And then you end up confusing the team and derailing plans. So I think like, I think understanding hierarchy becomes more important. I think in the, I think in the earlier early stages, you always want to keep the structure flat in some ways where people can communicate to you the problems and you can get kind of a bird's-eye view of what's going on in the business. And you want to make sure everyone's being heard. But when it comes down to execution, I think that's where the hierarchy becomes more important. So that's, that's something that's changed for us over time. But we're still— I mean, we're still a small team. Yeah, relatively speaking.

When, when something goes wrong say, you know, you guys work with consumer brands, say in one of your accounts something goes wrong, maybe the team's not delivering or the product breaks or something happens. I think in our stages when that happens, I still have the bad habit of jumping in and I'm like, "All right, how can I help? How can we fix this?" And have you had to train yourself to not do that anymore?

[Speaker:DAVID] So that one, it has to do with customer issues. I'll still take a look, but I'll never, I'll, I'll still intervene. I think that's something that I think that's—

I think that customers are everything though. So that one I think is like the one area where I would, I would hope even at the highest level people are like still wanting to intervene. But I think the thing that I'm hearing is really just that like your decision-making model had to elevate as your team was growing, as your company was elevating. Like you have to be better about prioritization. Like, because if you're doing one thing that is at the expense of the other things you could be doing, and obviously there's a million things going on all the time.

Yeah, I still think it's important to review everything and just make sure that things are going in the right direction, what you think the right direction is. But overall, you— I mean, you want to give people a sense of ownership, and you remove that sense of ownership if you're micromanaging. And then if someone's just not executing at expectation, then they're just not— they're just not the right fit, right? I think— I don't— I think the answer is not, hey, micromanage. I think the answer is, hey, you're just, you know, You know, that person's not the right fit for the company.

You're fired.

Did you guys have like a clear north star vision from day one or a few months in that you could like align key leadership hires around? Because I'm realizing right now, like as we look to hire senior executives, we don't have that yet because we're just still like very functional. Like, hey, we solved this specific problem, but I'm realizing the need for that is like, if you want to bring on good people, there needs to be something much bigger than just like the problem you're solving on a day-to-day basis?

Yeah, we've always had a North Star and a clear vision from when we started. I think what's changed is how we'll execute towards that vision. That's iterated over time, but the vision has always more or less stayed the same.

What is that vision?

We want to be the financial hub for the digital economy. So basically the way we think about it is The internet's created this unprecedented opportunity for people to become financially independent, and the best vehicle to do that today is really by starting an internet-based business. And there are different kinds of internet-based companies you can start today. E-commerce is the sort of one of the most accessible ones and the one where there's just a lot of people doing it. And so our approach has been to really like focus on this one vertical and build the, uh, the best financial products for them. So really what we realized when we were building our own e-commerce or other kinds of internet-based businesses is if you look at like the internet's been around for 20+ years, but there's still, and there's a ton of companies and products that have been built around solving the needs of internet businesses. Like you can just look at Shopify and how massive a company that is today. But if you look at the financial space, really there's no, um, there's no company that you can pinpoint to and say, hey, this company helps me understand my financials in real time in a very easy way. This company is where I go to to get access to the financial products I need to scale my business. So we really want to like just own that category and be that company.

Yeah, I mean, I feel like it's— you had the institutions and the banks were like the first wave into fintech, and now it's like which progressive startup is going to be the one that successfully like derails or becomes the new norm, to your point, like the new North Star of how to be able to do that.

That's right. If you think about the banks and the incumbents, it's— they don't have— so they have the basic— they're like good enough products, but they haven't really— they don't really serve the needs of— they don't, they don't really get the internet, internet economy that well, right?

So no, but I, I think there's two, two points to it in my opinion. The first one is it's money. So like people treat money different than anything else, right? Like the thought of handing your money over somewhere else or someone else being in control. And I think the second one is that the larger the company gets, as you guys know, the harder it is to iterate. So you have these massive banks who have meetings about meetings about meetings just to like entertain the idea of doing something innovative, which is why they— I don't think they're going to end up being the ones at the finish line with businesses like yours that are like really trying to disrupt them across the board.

Yeah, that's right.

Um, I'm curious about your life away from Parker. Like, what, what do you like, what do you do, what do you do when you're not building this company?

Yeah, I like, I like traveling a lot, but I don't travel as much as I, as I'd like recently. Um, read. I'm a big reader, so I used to read like an insane amount. So I'm a big— I love information. Like, I love digesting new information. Like, I'm definitely an information junkie. Like, it's I just love reading, learning about new things. I think, um, no, I think recently something that's been interesting to me is just observing how, um, and I've talked to you about this a lot, right? So I think if you look at the, if you look at the world of people who are trying to get rich off the internet, I think you can dissect it into two, two kind of spheres, right? So you have the kind of like bootstrap world where you have people building agencies, you have people building e-com businesses, bootstrap SaaS, being YouTube creators, all this stuff. And then you have the institutionalized world, just call it the world of venture-backed companies, right? So a lot of the— a lot of people have good success in the bootstrap world, but if you look at the biggest outcomes, they've come from the venture world. And so something that I'm very curious about that I'm learning a lot more about now is really how to bridge that gap because I'm seeing a lot of really good marketing tactics that people from the bootstrap world, call it, are doing that I see not being utilized in the venture world or the tech world that I'm from. And so I think if I can apply some of these tactics to what Parker's doing, could be pretty promising. So I think on my free time, just doing a lot of research on that has been interesting.

I think that's such an interesting point about the marketing tactics, and I'm curious if you agree with this or not, but I think one of the limitations around what some of those bootstrap type businesses are doing from marketing perspective and what the institutional venture backside are doing is there's no red tape. Around like how vulnerable you are, how you talk about things, how you do things when you don't have investors, when you don't have a board. Um, do you feel like that has any sort of limitations in terms of like how progressive you can become with like marketing with an institution-backed business?

I'm trying to see if the, um, if the limitation is more imagined than reality, because at the end of the day, you are working to build a successful company and you want You want to build something that changes the world. And so if there's a strategy that you can take that helps you achieve that goal, I don't think it's really a problem.

Yeah, I guess investors, all they care about is the amount of money you give them back at the end of the day. I don't care how you get there.

On that note, we talked about setting a vision or North Star and then putting a mix of people and capital in place to get there. How have you guys thought about the capital side of the equation? Because I know you guys have raised capital multiple times, I think.

Yeah, the capital side is basically an exercise in relationship building and building trust with the right investors over time, and then finding investors who actually believe in the vision and want to back it up. So the venture model is VCs aren't looking for a business that's going to sell for $100 million one day. They're looking for that $10 billion exit. And so you need to find basically the believers and the people who see how this company can be worth that much one day and how their capital is basically an accelerant to that becoming a reality.

How did you go about the process of raising, or I guess walk us through like what you've raised and different approaches you've taken or like learnings that you've had since the first round to the most recent one?

I would say my general approach is always to keep that keep things very simple and not overcomplicated and break things down to what the mechanics of a process really are. So if you think about, um, raising money— raising money is having a conversation with an investor and convincing them that it's a valuable opportunity and then getting them to send you a term sheet. And so that's a matter of getting the right introductions to those investors setting up the right presentation, and then creating the right dynamics such that they actually want to invest. So for the introduction, it's just tapping into my— basically making a list of all the investors who'd be interested in this business, then having a list of all the people I know who can get me in touch with those investors, asking for introductions, and then making sure that I'm communicating very clearly. What the opportunity is, and then building a relationship with that investor over time so they essentially build confidence in our ability to execute.

That, that last component, that— I mean, it's essentially like a trust component. Yeah, like, if I give you $4 million, are you going to screw me over, basically? And so that's the more, I think, qualitative one here. I'm curious to get your take too. Once you found the right people, I think you've pitched the right vision or convinced them in the right way and they're ready to sign. What is that qualitative part of it? Like, how do you build those relationships? How do you build that trust from your experience? And I'm curious to get yours too.

I think the way you build trust is you have enough touchpoints over time where you're repeatedly executing on the things you say you're going to do. So if I say, hey, we're going to reach these numbers and we're going to launch these products, and every time I say that, we do it. Then the investor is like, okay, well, know this guy, this team for a year, gotten to know people on the team. Every single point in time, they've just basically executed against their plan. So, you know, this is a team that I want to back because if I don't back them, then they'll keep executing and I'll miss out on, on what these guys are doing.

Is part of that patience in developing that relationship? I'm not trying to rush anything.

Yes. I would say though, the first— so the first big fund that invested in Parker, it's not like I knew the guys for years or months. They kind of took a bet. They just, they met us. We had the right introduction. The introduction spoke highly of us. And within a couple of weeks they made a decision. So it's not like we knew those guys for years. Ahead of time. But then I think what led us to give us more money over time is they just saw how we repeatedly executed against the plan.

Have you found that the way you manage these relationships has had to change as there's been more zeros added to the end of the number? You know, like when you're raising a pre-seed called $500K and now you're like at what, you raised the Series A in your last round? Now you're having conversations of $5, $10, $20 million. Like, have you seen a shift in the dynamic of those dialogues versus when you're at the earliest stages?

Uh, I would say it looks pretty similar. It seems pretty similar to what it was. I don't think it's changed that much. I just think the, the relationship management is very similar. I would say what's changed is just what's being prioritized in the business. So I think early on it's more narrative-driven and opportunity-driven. As you scale, it's more metrics-driven.

What keeps you up at night about the business? Like, if Parker fails, why Parker fails?

It's just because I didn't work hard enough.

How do you keep up the— how do you keep up the pace after— over the course of like multiple years and multiple years to come?

How do you keep— what do you mean, how do you keep the pace?

The pace and the energy.

Because I feel, again, like avoiding burnout.

Yeah, like we're— I think we're both what, like a third of the size that you guys are right now. And we've been doing this for a year, year and a half or something. And the biggest learning, I think, for me has just been like showing up with a ton of energy every single day to every interaction and pushing the pace. Does that get tiring sometimes, or is that second nature?

Um, I think the way I've done it historically is I'll just— so I've never, I've never taken a true vacation where I'm just turned off from the business. So that I've never done. But there'll be times where I'm— we're operating a little more slowly, just like, you know, I'll be away. But generally speaking, I think you have to— if you want to win big, you just need to keep the pace pretty strong for a long time. So for us, for example, with Parker, Milan and I were working very hard for a couple of years. Without things breaking out. And no matter what, we were still working. Just, I mean, you have to work on the smart too, right? So it's not just a matter of hard work, but in terms of pace, we were very consistently going after what we wanted for, I think, 2.5 years before things started working as well as we wanted them to.

I also feel like as an entrepreneur, the one luxury you do have is the ability to make decisions that you wanna make in terms of like, I need to close my laptop today, or I need to like reset or find those things that allow you mentally to like keep going. 'Cause it's obviously a grind. I think to your point, I don't remember the last time I went on vacation, I was successfully able to like not check my email for like 3 days consecutively. Like the thought of that gives me so much anxiety.

Yeah, I don't think—

For better or for worse, but—

I don't think the vacation thing is what's necessary. I think it's more so about, Usually if you're burning out, it's because you're, you know, you haven't made the right hire. There's something operationally that's broken that's leading you to lose focus, or it's that you're not taking care of your health. So taking care of your health is paramount, right? You wanna make sure you're sleeping, you have, you know, decent sleep, you're eating well, that you're doing, you're exercising, you're doing all those things. If you're not taking care of your machine, things are gonna break down.

You stopped drinking, didn't you? Did I make that up? Yes, I made that up.

No, no, I stopped drinking.

Oh yeah, I thought so.

Yeah, mostly.

Were there specific moments that— not that you burned out, but you realized like, hey, I'm not functioning or not driving the pace as much as I want, and so I'm going to protect my health more? Was that a learning over time, or from day one you're like, I know I got to protect my health and I'm going to do it?

Uh, there was definitely a time when we were starting out where I had to really take care of my health. So I had— there was a time where I had some pretty bad health issues when this was even before we raised the seed round. But since then, no, there's been nothing dramatic where I just couldn't.

Can you talk to us about that?

Sure. I had, uh, had like mercury poisoning when I was, when I was in my early 20s. So I just could not— it was very hard for me to focus. So I was trying to like build this business while I was poisoned. And then I realized what was going on because essentially I went from studying some of the most complicated subjects in the world, studying physics and computer science, to building these other businesses, killing it. And all of a sudden I just could not focus on anything. I couldn't function on anything. And so that's when I had to look into what was going on, my health. And yeah, it was, it was a crazy—

how do you get mercury poisoning? Is that a stupid question?

I don't know.

I've never met someone in my life. What does that even like?

What's like the manifestations of that? Like brain fog? Like you couldn't—

it's like very severe brain fog. Like very severe. Like you're just, you're just not— it's like, um It feels like your brain is paralyzed.

How did it— how did you get it to go away? It was like a medication thing?

Yeah.

That's so interesting. I've never heard of that.

Like supplements, Medicaid. It was pretty intense.

Yeah, I've never heard of that before.

Superpower.com.

There you go. Um, so the name of the podcast is Turning Pro. The concept of it generally is around like moments in your life where you take things to the next level. Think like getting up from a poker table and going to one that's more high stakes. Like, what were a couple moments in your life where in your own mind you were like, I'm, I'm becoming a professional now, taking things to the next level?

I think it's when I internalized that the one of the most important things I had to do as a founder was focus on fundraising, and that if I had to, if I wanted to build a massive company, I needed to have a lot of capital to do it. And so something switched in my mindset where I thought, hey, um, instead of just being focused on the day-to-day operations, I need to focus on meeting the right investors and convincing them of this opportunity because this thing will not get big without the right amount of capital.

Do you have any advice for people listening who are maybe first-time founders or early founders just around the stigma of raising money, like the mental model to use to know if it's something you should or shouldn't do? 'Cause I think there oftentimes there's this idea that people think that like raising money is the way to quantify how successful you are or how great your company is. But a lot of businesses don't actually need to go that route.

[Speaker] Yeah, I think most businesses actually don't need to go that route. I think what's important to understand if you're raising money as a founder is you're sacrificing short-term liquidity for a payout in the long run. So let's say you have a profitable SaaS business that you're running, the, you know, if that business is cash flowing month over month and you're pocketing that money for that lifestyle, for building the lifestyle that you want. The day that you raise institutional capital, that's something you can't really do anymore. So I think the— and I also think raising money is not the goal. It's just capital, right? The goal is to actually build the business and generate revenue. I think for us, we were building a fintech, so it was impossible to have this model without venture without a substantial amount of capital, which we actually saw as an, as an edge, right? Because we knew that, hey, someone can't bootstrap what we're doing. And so our ability to raise money is actually a competitive advantage here. So I think that's how I would think about it. But generally speaking, I think if you're just starting out as a founder, I view, I view playing the raising money game as kind of almost trying to play the Olympics of business. And so if you're starting out, it's, it's probably one of the Work— it's probably one of the worst things you could be doing, to be honest with you.

Yeah, well, yeah, I mean, I think it's, I think it's accurate though. It's not the first thing that you should be thinking about. It's like, you know, get through the mud and then figure out if you need the money to keep going or not.

Yeah.

Yeah, I don't think, uh, I don't think it's the first thing you should be thinking about. I think the first thing you should be thinking about is Well, first of all, it's like you have to build your skill sets. Second, you want to find a way to sell those skill sets. Third, you want to make sure there's actual demand for what you're building. You want to make sure you're getting— it's like you don't have a business until you have customers. So like step one is get customers.

How did you— I don't think I've actually talked to you guys about this. Martin may have mentioned it, but all of a sudden, I feel like overnight I started to see Parker everywhere, like a year and a half ago or something like that. And there's definitely been waves of e-commerce infrastructure or fintech infrastructure or SaaS. And I think the old way of how maybe Klaviyo and Postscript and other companies came about was a completely different go-to-market motion. And the first time I heard about you guys was hosting parties and dinners paired with a great brand and a really damn good product that customers seemed to like. So what did you guys do differently that seemed to have worked?

I didn't want to run ads and I wanted our CAC to be super efficient. And I realized that what— so I was building these e-commerce businesses before, and I knew that something that appealed to founders was lifestyle. So I know that what a lot of these business owners are really after is creating a lifestyle of freedom. And they want to tap— they, they want to have access to cool experiences. And so I knew that, um, hosting these, these kinds of events that, that they wanted to be a part of would be a far more effective strategy to, um, to building relationships than targeting ads or even just doing pure sales. And I knew— so what the thing I knew about Parker was that I knew the product was really good and I knew the market wanted it, Our issues, we just needed to build trust, right? Because if you're building a financial product, it's important for people to trust you. So the initial strategy was really to get the, sort of call it the top brand owners, to really like what we're doing and speak for what we're doing. And I knew that the way to speak to them was really by hosting these cool events.

[Speaker] You guys have like really pushed the limits on that too in terms of creativity. You've done, like, wasn't there like a racing, car racing like activity that you guys did?

[Speaker] Yeah. There was car racing, there was Carbone in New York, there was, yeah.

Oh yeah. I'm curious, every growth investor that I know and that I talk to talks about, like, this is like Series A+, Series B on, um, that any mature company needs to have a repeatable go-to-market motion and a repeatable way to acquire customers at scale. And that's when a Series B investor will come in. Right. And so go-to-market is obviously very different. Like, again, maybe events scale. I'm not sure. And I think events are really important to build trust early days with that first pilot cohort. Has that motion had to change over time, maybe towards a traditional enterprise sales motion or other motions?

So we were always doing outbound sales, and outbound sales is just known as a scalable strategy. I think early on you have to do things that don't scale, and you have to do things differently. You have to think about ways to get to your customers that others aren't doing. And so doing the event strategy was very effective. Early on. And there's actually, there's actually, uh, I can't talk about it yet, but there's something we're going to do around events that's going, that's going to feel like a more embedded experience into Parker. And I think that's going to be quite scalable.

When's that launching?

Working on it now.

In the works?

TBD. Yeah.

Are there like founders you look up to or like books you've read that have really like impacted the way you operate? Or just mentors in general, I guess?

I think something that's influenced me a lot are Paul Graham's essays. So Paul Graham is the founder of Y Combinator. He started a company called ViaWeb that he sold to Yahoo in the '90s, I think '90s, early 2000s. And he, he founded Y Combinator, which is the most important startup incubator in the world. And if you just look at the companies they've backed, it's, it's just insane. So I was very lucky to raise money from Paul Graham very early on and to have had a couple of conversations with him. I'd say that his essays have— his essays basically gave me the playbook and blueprint of how to build Parker. Early on. And then I think there's a book called The Sovereign Individual that's been pretty influential on me, and it talks about basically this concept of how the internet will enable this new class of people that kind of act as sovereign individuals. And so freedom's a very important value of mine. So that book has had an influence. And then there is— I think Zero to One is also a pretty good You know, it's very popular, but I think it's a very good book to read.

Were there any anecdotes from the Paul Graham essays that like stick out to you?

Yes. Do things that don't scale. That's, that's a big one. And then just the emphasis on everything he said.

Now we know why they did the events. Love that.

Yeah. Everything he says is actually very simple and clear to understand. I think what I've learned from his essays is just the importance of clarity of thought and the importance of simplicity. So, I mean, he has an entire essay on doing things that don't scale early on, right? Because when you're an early-stage company and no one knows about you, you have to go the extra mile to get people to listen to what you're doing. Otherwise, you'll just, you'll just be noise.

When I, when I graduated from college, I went straight into VC in San Francisco and like 2 months in, somehow I weaseled my way into like the investor side of things for Demo Day. And after I went up to him, he was in like sandals and shorts.

Oh yeah.

Like some ridiculous, like, Bahamian fit. And which is apparently like his fit. Um, I went up to him, I shook his hand. I was like, man, I'm so excited to be here. Like, uh, I, I read all your stuff and I, I moved to Silicon Valley because of you. And he, he was like, oh, cool. What are you doing? I go, I'm a VC. And he was like, why? And it still stuck with, and I did VC for like 4 years after, but finally I took that advice. Um, but again, like that very blunt questions of like, why would you do this? Yeah. Yeah. And I think most of his advice is like that.

Yeah.

And like, taking that face value.

He knows a lot about e-com, by the way.

Really?

Like, way more than you'd think. I mean, he started— he started a predecessor to Shopify. That's what ViaWeb was.

Oh, really?

He knows a lot.

That guy's forgotten more about it than we'll ever know, I guess.

When I spoke to him, I was very surprised by how much he knew.

Is he dropshipping right now?

He knows about, like, poor dropshipping. He knows what dropshipping is. He understands the model quite well. Like you wouldn't, you wouldn't, because he has a PhD from Harvard, so you wouldn't expect him to know about that world, but he does know a lot about it.

Paul Graham, dropshipping king.

I think that's just a byproduct of curiosity though. Yeah, it's like guys like that just find a way to, like, I think you're similar in the sense that you find a topic and you just like go down a rabbit hole for like weeks and months at a time and just come out as a, not a subject matter expert, but like people don't expect you to be able to sit and have like a very intelligent conversation about something that you surprise them and you're able to.

Yeah, yeah, that's right.

I'm curious for you right now, I guess this is like real-time riffing on your go-to-market because you're starting to share a lot about it, which is awesome. Obviously this podcast, but your other creator series and other work you're doing. How are you thinking about go-to-market for Platter, whether it's events but also different type of events?

Yeah, I think they have— Parker has definitely been an inspiration around the events piece. I mean, what you've seen, and I've obviously talked to Martin a ton about it. And I've been to like a lot of these events with— there's only a couple like people who are doing events, I would say, in New York that are like the cornerstone of all the events. Uh, and so I think events is definitely something that I want to try. Uh, I think the, the relationships, at least in the New York City community, seems to be very like incestuous and small. But the thing that I'm still trying to figure out is like scaling beyond this community as it relates to events particularly. I know a couple people who do event series like across different cities in the US. Um, for us, candidly, I think the go-to-market is still something that we're, we're evolving over time. I mean, it's— we're recording this now probably like 6 to 8 weeks before we're actually going to be launching, uh, the new branding. We have a marketing plan in place in terms of how we think about wanting to roll that out, uh, but I would say a lot of it is more digital, um, in terms of like we're like a partnership program just by nature of where our product is positioned, uh, but I've definitely been someone who's been more and more interested in the events because I think something I've learned is that being able to build these in-person relationships, a lot of my success on the sales side has come from feeling like I'm working with friends and not like feeling like I'm working with customers.

Yeah, I think that's a gift. I think that's rare.

Yeah. But again, it's like, to your point, do things that don't scale. Is that— that's not going to be the thing that gets me to building a $100 million, billion-dollar business of like building a relationship with every single customer. But I think it's like building relationships with these people, making them customers. And then like there's compounding effects in terms of doing right by people. Like, I think for me, I'm curious if you feel similarly. Like, one of my benchmarks for knowing if I'm like on the right path as far as product is like, are my customers referring other people because they're so happy with what I'm doing for them? Like, we've had a lot of success with customers not even having a referral deal in place. Like, oh hey, I want you to meet this person because you've solved this pain point for me and I think you can do it for them as well.

Yeah, I think our— when, when Verbatim started like a year and a half ago, I think we can track like 60% of all revenue from Scott Sonborn at Taido and Ken Davidson at Skio, which I know, you know.

Yeah.

And it was just the two of them have just been referral machines. I mean, again, refer one person, then we do good work for the next person. They refer more. But you can really trace things back to, again, we're bootstrapped, different vision, but like a handful of relationships that you, you just become genuine friends. Um, and again, you don't have to work together forever, but I think that really does matter. And I'm sure you in like 3 years with Platter will look back and be like, oh, that person that I met at this event that I really just wanted to become friends with and you became friends with. I'm sure that'll track back to hundreds of customers over time.

Yeah, that's the goal. And I think the other thing for us too is because we've been very narrow focused to date with what we've been building, there's a lot of marketing strategies that I have, like curiosities about, but it will really be like testing and iterating very quickly before like leaning into something and scaling it. Because I haven't like tried enough, uh, in the current brand in terms of what I think will work for us at scale.

I'm curious, we talked about what you've had to sacrifice like as an operator, basically, like what habits you've had to give up or change in your approach. Personally, what have you had to sacrifice aside from just vacation? But maybe it's like, hey, you said you work till like 8 or 9. And you're waking up at 8, that only gives you a few hours at night. Like, what are you sacrificing on the personal side of things?

I don't feel like I'm sacrificing anything, to be honest. Like, to me, the way I see it is I'm living my dream, right? I've had this dream since I was basically a kid, so I don't— I feel like I'm only really winning. I've never, I've never felt like I was sacrificing anything.

Do you feel like you're exactly where you want to be right now?

Uh, no, I definitely wish I was. I definitely always think I'm behind and I need to like move ahead. You know, I think the only thing I probably sacrificed was my health at some point, which I realized was a mistake. So that's something that I've I've sort of course corrected on, but no, otherwise I never, you know, I think something that's helped me is I was always a very hard worker from a young age. I was always very competitive from when I was an actual child. So from when I was like 8, 9, 10 years old, I was just always very ambitious. And so to me, I've never had to really shift the way I worked. I've had to shift the things I worked on and my priorities.

I'm curious. Dude, that, that line that you just said resonated so strongly with me of, I feel like I'm always behind and I feel like I need to move forward or push faster.

This goes back to the question that I always ask. This is one of my favorite questions asked on the podcast. Uh, what do you think are the 3 most common traits of high performers?

Of high performers? I think it's important to have a chip on your shoulder. I mean, you obviously need a lot of ambition, so to a point where it's almost delusional where you think you can create— you have to believe that you can create a reality that is different from the one that exists today. And that requires a lot of tenacity, a lot of vision, a lot of ambition. And just, you have to, you have to be willing to make sacrifices.

I think for the reason I asked that question, I was like scrolling TikTok months ago and a video that I came across that I've heard multiple times that like it, it stuck with me because of like this conversation, is that one of the most common, uh, traits of high performers is the feeling of inadequacy. Which is why, like, when you say that, I laugh, because it's just this notion of like, I, I need to do a little more, I'm not where I want to be. And every time you level up in the game, call it the game of life, like, in your mind, now it's time to get to the next level, the next level. So the fact that you never feel like you've made it is the reason that you're pushing so much further than some other people could ever imagine?

Yeah, I don't personally feel like there's anything wrong with me for not being where I want to be. But if I'm just objective about it, there are companies, there are people who have better metrics than I do. And so when I see that, I realize, okay, there are things about the world and there are things about business or there are things about myself that I have yet to learn. And that's why I'm not there yet. I'm not like moving at, I, at sort of the speed I want to be going at.

But do you think there's a final destination? Because like, I love, I love hearing when you, you see someone who's like called 60 years old, who's built 10 businesses, has millions, hundreds of millions of dollars, and they're like, I still don't know what I want to be when I grow up.

Yeah, I don't think there's a final destination. It's more just this constant iterative cycle. Where you're— there's— I think the Stripe founders talk about this. There's a book called Finite and Infinite Games, or maybe it's the reverse.

I don't know. Infinite Games.

Is it just Infinite Games? Okay. So that book basically speaks of that concept where you want to be playing an infinite game, a game that has no end, and the point of the game is just being in the game. So I think it's kind of like that.

I think I need to read this book. What's it called?

Is it just Infinite Games?

I think so. Maybe it's— I'm not sure.

Yeah, sounds like a book. Something good for me.

Something about games.

Yeah, I don't care what it is.

I'm, um, what you said right there is— I, I feel it deeply of like, we're— I'm not moving as fast as I want to be, or I'm not where I want to be.

But so where do you want to be? Where's— what's the gap between where you are now and where you want to be?

I mean, business should be 4 times bigger, growing much faster with like key senior leadership in place.

So yeah, but what's your— what's your basis for feeling that way?

Because I hang out with you guys all the time.

Yeah, but I feel like if you get— if your business 4Xs and you have these key leadership people, we're going to be sitting here again in 12 months and be like, my business should have been sold already for like a billion dollars, whatever, right? So it's— yeah, I want to like— I want to challenge you a little bit on that notion. Is it just you always wanted to be a little bit better? You actually feel like you've fallen short of where you want to be, being realistic? But that's the word. I think that's actually the hard word to bring into this context is the word of being realistic. I think the reason that we do the things that we do, to a point you made earlier, is like you have unrealistic expectations.

Here's the thing about being realistic. I really believe that if— this is more true of, say, uh, business than I think, say, like basket— like playing the NBA or something. But I really believe that if especially in business, if someone else has figured it out, then it's just— and you haven't, then that means that you're, you're still being realistic, right? It's like these $10 billion companies do exist. It's not like they're— it's not like they're not out there. And so there is a path that you can reverse engineer that can get you to where you want to be. Now, Maybe that's not what you want, right? But if you identify what you want very clearly, then there is a path to getting there. A lot of these paths have been walked before. So I think the realism— I think there is a point in time where everything I'm doing today, someone thought was very unrealistic for me to achieve. And if I hadn't had the mentality of, no, that's not correct. Like, let me let me question what people think is possible, then I just wouldn't be in my current position and neither would any of us, right?

Where, where does your ambition and your chip on your shoulder come from?

That's a deep topic to explore.

Let's get into it.

That's a deep topic to explore. I think for me, it definitely comes from just, I think it definitely comes from childhood. I think it definitely comes from just feeling like I couldn't get what I want. I think it's, it's partly from some childhood stuff, and it's secondly part from just these existential questions I would have as a teenager of like, what's the point of all of this? And if we're alive, like, what are we gonna do with the time that we have? And then just coming up with different experiments and answers to those questions.

Did that ambition scale over time?

I was very— I was extremely ambitious growing up, so it's still— I think it's still there. I think there was a point in time where I probably had more doubts about it, and then it just had a revival.

And then you get like validation point.

Yeah, exactly, exactly.

Yeah, I think— I, I mean, I'm, I'm loving just listening to this because I feel very similarly. I think the The doubt was— the doubt from other people was something that drove me, is like wanting to prove people wrong as a means to just like push myself. Uh, and I'm curious, were you an athlete when you were younger?

I played a lot of sports, but I was— I think, I think I was a good rugby player. I was a decent rugby player. Now I was like, okay, but I did play a lot of sports.

I, I think for me, I always pull back to my athletic side of my life is the thing that really helped me shape like the competitive nature, which sometimes is like— it's a blessing and a curse because I— you'd like turn everything into a competition. But I think part of that has just been like gamifying certain things in my life has actually allowed me to elevate it 100%. Uh, so I'm always curious like where people's ambition comes from because I think for me the gamification is something that makes it very easy for me to try to like push myself to levels beyond what I could imagine.

Were there a couple moments for you where you got those first few points of validation that, like, it's not just completely delusional ambition? It's like, wait, I have, like, I'm starting to acquire some of the skill sets and small wins that helped you gain confidence?

I think that Y Combinator was a pivotal point because it validated that we were on the right path idea-wise. So I think that was— that's, that's when we started gaining a lot of confidence. Um, and I think just seeing financial results really helps. So I think if you're seeing that what you're doing is generating revenue, then you start thinking, okay, something about what we're doing is working.

Were there any moments, almost pulling back the veil, where you realized you're having conversations with some pretty successful, high-level people, and that's your new poker table, that's your new room. There are definitely points just for my validation on the journey. Sometimes even conversations like this, sometimes I'll step away after one of these podcasts and I'm like, "Wait, no, we can actually get advice from each other. We're learning from each other." And these are pretty successful founders we've had on. Those have always been validation points for me. Have you had any of those conversations where you're like, Wait, I think I'm actually at the same level. Like, I can go tit for tat with these people.

The way I've thought about it was always more in terms of what can I learn from others and what are the right questions for me to be asking. I'm usually— this is odd for me because I'm usually trying, I'm usually trying to be in a position where I'm asking people questions to learn rather than just like saying stuff. But Yeah, I would say that I think when we were early on in Y Combinator, that gave us the ability to meet people like Paul Graham, to meet Xavier Niel, who's a French telecom billionaire, and get their advice, or meet the founder of Docker, meet the founder of one of the Rippling— sorry, one of the Zenefits founders. And so I think it's more so realizing that you can learn from these people, absorb their insights, and then execute on them and seeing the results. Where over time you can build the belief that, oh yeah, that's— this is something, you know, if he did it and I could learn, then this is something that's possible. It's not, it's not crazy.

Uh, I think we're coming up on, on an hour here.

Um, it was fast.

What?

It was fast, fast hour.

Yeah, I think good, good conversation. That's usually what happens.

We'll have you back in a few months to unpack the childhood trauma and ambition. There you go. Traces of Yacine Sibouche.

Any final questions?

No, man, that's all I got. This is great.

Yeah, it's fun.

You want to just look at the camera, let everyone know where they could find you and what you're working on?

Where they can find me, uh, you can find— I think you can find Parker on Twitter.

Can't find Parker.

I move in silence.

No, yeah, my Twitter handle is @YacineSibouche, so you can leave that there.

Awesome, man. Appreciate you coming on today.

Thanks, man. For sure.

Thanks for having me.