
When I first started Foundr, I made a lot of short-term decisions — and most of them hurt us more than they helped. It took years (and a few hard lessons) to understand that sustainable growth only comes when you play the long game.
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Hey, founder fam. I want to talk to you about something super exciting. We're officially partnered with Omnisend, the email marketing and SMS platform built specifically for e commerce founders. We've been recommending Omnisend to founder students for a while now because it just works. Whether you're launching your first store or you're scaling to seven figures, it really helps you automate your marketing and get real results. Did you know on average OMNISEND customers make $68 for every one, one dollar they spend, which is an insanely good return on investment. And because you're part of the founder community, you get 50% off your first three months with the code FOUNDER50. Just head to omnisend.com founder without the e to get started. All right, now let's jump back into the show. Hey guys, Nathan here. Welcome back to another episode of the Founder Founder podcast. These are short, bite sized episodes where I share my lessons learnt building founder, everything I've learned From interviewing over 100 billionaires doing this stuff for over a decade now. And what I want to talk to you guys about today is this idea of winning deep, not shallow, and why playing the long game ultimately is the best way to play any game when it comes to business and having a long term strategy. Hear the stories, learn the proven methods and accelerate your growth and future through through entrepreneurship. Welcome to the Founder podcast with Nathan Chan. This is something I've been thinking about a lot because I've made a lot of mistakes at founder and a lot of those mistakes, if I was to really boil it down, comes down to short term thinking and I want to give you some examples here around how I've kind of thought short term and why it's actually hurt me in the past. And every time I've played the long game around winning, winning deep, not shallow, has actually ended up way better off. So let me give you an example because I think oftentimes when you're starting a company, you're thinking so short term, right? You're thinking, oh, well, I gotta get this sale and I launched this product and I do this and I gotta get this marketing channel and I got these ads right, and then I can just keep growing, growing, growing, growing, growing. But what you find is before you know it, you get caught up in this hamster wheel where unfortunately you're just spinning and you just keep spinning and that you can be caught up for years in that hamster wheel winning shallow. Like, oh, I did this awesome Black Friday launch. How good is that? You know, we made an extra 50 grand in net profit or whatever it is. Like, how good is that? But then you realize, okay, well, what's happening next month? And. And then, oh, okay, then, oh, now I need to do a Christmas thing. Oh, I'll do this launching campaign. Oh, bang. All right. Yes, we beat last year. Now we made an extra 20 grand. Okay, what's happening next month? Oh, January. And you see where I'm going with this? So it's so important, and this episode is a message for you to take a step back and reflect. Yes, you can have short term plays, but what are your long term plays as well? So let me give you some examples. So sometimes when you're trying to grow your business and, you know, perhaps you have some challenges, it's easy just to go short term thinking, all right, I can cut some costs here that gets us back into profitability. Okay, I can do this promotion here that'll bring in some short term cash. Okay, I can do this partnership deal that's going to actually get them to promote me. And I'll promote them like, oh, okay, I can pay this influencer this amount of money. You see where I'm going with this? But then if you actually step outside, from my experience, the things that I've found have yielded the greatest results is looking at your business and going, okay, well, we've got these things happening right now, which is bau. But what are the moves, what are the strategic moves that we are going to make over time that we believe will yield really great results, but they're going to take time to come to life? So I'll give you an example. There was a time when our Facebook ads just got absolutely destroyed. We lost a lot of money, like very, very quickly lost, I think it was like close to half a million dollars in one month. It was crazy. And so naturally I'm just like, all right, well, I gotta recoup, I gotta rebuild. You know, like, we lost a lot of money. Let's, let's just do this promotion. And then it's like, oh, okay, the promotion did well. Yay. How good is that? Okay, now let's do this other promotion and you can get caught up in this short term thinking around, oh, okay, I've gotta make profit, I've gotta do this, I've gotta do that. But what I wasn' was it got me, it snapped me out of this long term thinking. Like, what were the products? What were the moves? Who are the people that we're going to partner with? What was the long term thinking? Right? So the Immediate was we wanted to bring cash immediately, want to do sales, promotions, all these short term things. But where I was falling short, I was caught up in this hamster wheel. What I should have been thinking and obviously over time I work this out was like, okay, well what do we want our products to look like? What if we launch the subscription model? It's a lot of work. It's going to take us six months to build that platform, but when it launches, it's going to pay its weight in gold. And so now more than ever, as a business, as a brand, I'm looking at things going okay. We've got some short term plays over here, you know, like this promotion here or this thing going on here. But what I'm really interested in is winning deep. So for us, as an example, we're upgrading our whole founder course platform. It's going to be a crap ton of work. You are not going to see an immediate massive wave of sales in the next month. It's going to take us at least six months of work to get it to a place where it's in a really, really, really good spot. We're going to launch this custom tailored app. We're upgrading our onboarding, we're upgrading the whole experience, we're upgrading what it means to become a member. And I'm super excited about it, right? And we're investing a lot of money into this, like a lot, a lot, a lot, a lot of money to upgrade this platform. It's going to take time, at least six months, it's gonna pay off. But we won't get those returns until six months from now. And some people would be like, well, you could do this, you could do that, you could do that. And I used to think that way. But now more than ever when it comes to business, I'm looking to win deep, not shallow. And that is something that Gary, one of my leadership coaches and mentors, someone we interviewed on this podcast, taught me. How do you win deep, not shallow? So what are some other ways of winning deep, not shallow? Looking at your team, looking at leveling up your team, looking at coaching, looking at having clear vision, values, a clear strategic plan, and getting buy in and taking your team on a journey instead of just holding them accountable to like short term thinking. You look at the founder podcast. We're putting in a lot of effort, energy, intention. How do we win deep there? Because we know the bigger we build this show, the more people like you guys that are listening to this will want to work with us, right? We don't see the immediate sales. So you can't win deep though, on everything. You have to choose, you know, what are two or three strategic bets that you want to make over a 3, 6, 9, 12, even 2, 3 year period that you know or you believe that if you get this right, it's going to take time to build it, it's going to take time to create it, it's going to take time to bring it all to life. But if you do that and you do it well, it'll pay its weight in gold and returns. Another example is sometimes you just don't know. What you don't know is slowing you down. And I think when it comes to business, you can look at what other companies are doing and you can draw inspiration and you can say, hey, if we do this thing, we believe this will happen, or we run this amount of tests, this thing will happen, but you don't truly know. And if I'm being honest, I didn't even know like what was happening in my market until I actually kind of stepped outside of it and assessed the landscape because I had an ego and was just like, all right, now I'm going to go deep. I'm going to look at what other people in our space are doing, how they're serving their customers. And I wasn't close enough to the customer and only through getting close to the customer and really looking at the intent of our customers, how we can help them succeed. That's when I realized, okay, we need to win deep, not shallow. We need to stop guessing what our customers want. We actually need to speak to them more than ever. We need to look at anyone in this space, in the online education space who is doing exceptionally well and why are they doing exceptionally, what products are they selling? How does it work? And then I've just started to really play out and build a plan long term and short term. So the summary here, guys, is when it comes to business, you always want things yesterday, you always want things yesterday, you always want that win. You always tell yourself, okay, when I get this, this will be amazing. So it's gotta happen yesterday. But sometimes you have to slow down to speed up. You really do. And as a founder, I know this is a difficult thing to hear, but the key message for you to take away right now, watching, listening to this episode is in order for you to win in business, you have to win deep, not shallow. Stop that short term thinking, yes, you can have a little bit of it, but what are you doing that is gonna win long game? Pausing before you ship a product to really understand what customers are telling you, fixing what's not working in your back end, looking at leveling up your team, playing the long game with your team or simply stepping back to reflect. Is this still working or is it still aligned? And if it's not, let it go play the long game. I can't stress this enough. This has been such a big aha moment awakening for me when I started to realize that I was just playing short term games, winning shallow and not winning deep. And the more that you can focus on winning deep I promise you it will pay its weight in gold. So guys, the takeaway here is constant motion isn't the same as progress. The founders who win long term are the ones who are willing to pull back, reset and aim with intention. I hope you guys enjoyed this episode. A little rant of mine and I'll catch you on another episode.
Episode 608: (Solo) Why Short-Term Wins Can Quietly Kill Your Business
Release Date: November 25, 2025
Host: Nathan Chan
In this solo episode, Nathan Chan explores why an excessive focus on short-term wins can quietly undermine a business’s potential for lasting success. Drawing from over a decade of entrepreneurial experience and interviews with top founders, Nathan articulates the key differences between “winning shallow” with immediate, superficial results and “winning deep” by building foundations for meaningful, long-term growth. He offers hard-earned personal anecdotes, a candid reflection on past mistakes, and actionable guidance for founders eager to escape the “hamster wheel” of constant, reactive activity.
“Before you know it, you get caught up in this hamster wheel… and you can be caught up for years in that hamster wheel winning shallow.” [04:10]
“We lost a lot of money, like very, very quickly… like close to half a million dollars in one month. It was crazy.” [08:05]
“We’re upgrading our whole founder course platform… it’s going to take us at least six months of work… but when it launches, it’s going to pay its weight in gold.” [12:02]
“Looking at your team… leveling up your team, looking at coaching, having a clear vision, values, a clear strategic plan, and getting buy-in…” [15:48]
“I wasn’t close enough to the customer… only through getting close to the customer and really looking at the intent… that’s when I realized, okay, we need to win deep, not shallow.” [19:27]
“You can be caught up for years in that hamster wheel winning shallow. Like, oh, I did this awesome Black Friday launch… but then you realize, okay, what’s happening next month?”
— Nathan Chan [04:25]
“As a founder, I know this is a difficult thing to hear, but… sometimes you have to slow down to speed up. You really do.”
— Nathan Chan [22:13]
“I’m looking to win deep, not shallow. And that is something that Gary, one of my leadership coaches and mentors… taught me. How do you win deep, not shallow?”
— Nathan Chan [14:36]
“Pausing before you ship a product to really understand what customers are telling you, fixing what’s not working in your backend… Is this still working or is it still aligned? And if it’s not, let it go.”
— Nathan Chan [23:42]
“Constant motion isn’t the same as progress. The founders who win long term are the ones who are willing to pull back, reset and aim with intention.”
— Nathan Chan [24:11]
This episode acts as both a confession and a roadmap, urging founders to pause, zoom out, and commit to building something of lasting value, even if that means embracing patience and uncertainty along the way.