Episode 700 | Playing the Long Game

Rob Walling:
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Welcome back to Startups for the Rest of Us. I’m Rob Walling and I am your host for this momentous 700th episode of this podcast. Today I want to talk about playing the long game. And what’s interesting is it’s a thought that I had three, four weeks ago that I threw into a topics Trello board that I maintain, and it hadn’t occurred to me that episode 700 was so close. But instead of having my friends send audio into the podcast, having my son interview me, which I actually think someone suggested and I think I’m going to do that, couldn’t pull it together for episode 700 or any of the other stunt episodes. If you go back and listen to episode 100, 200, 300 of this podcast, we did a lot of those things and they were really fun. 

For this one, I just wanted to do a Rob solo adventure and talk a bit about playing the long game. Before we dive into that, applications for TinySeed are opening on February 12th and close on February 25th. If you’re not familiar with TinySeed, it’s the accelerator I run for ambitious, mostly bootstrapped B2B SaaS founders. Even if you’re interested in applying outside of the window of February 12th to February 25th, you can join our mailing list to be notified when applications open. Again, visit tinyseed.com/apply to get on the mailing list or to apply. 

I’m going to admit I’ve actually struggled to sit down and record this episode. Normally for these solo adventures, I make a couple bulleted points and I just go. I riff. This one, I’ve struggled with… I’ve actually outlined it quite a bit, and so this episode 700, I can do it just as a normal Rob solo adventure, but there’s something that I want to convey in this episode that holds perhaps more weight than that, and it’s about this concept of playing long ball, or playing the long game. As I came up as an entrepreneur, I learned direct response marketing, and back in the old days, they talked about two types of marketers, brand marketers, which is like Coca-Cola, Procter& Gamble, Crest Toothpaste and Dove Soap, and how those marketers could spend a kajillion dollars on a Super Bowl ad just to get the exposure, whereas direct response marketers needed to have a measurable return on their investment. 

So if they took out ads for 100 dollars, they needed to make 110 or 150 or $200 on those ads, and be able to measure that to stay in business or to convince themselves they were making money because they didn’t have infinite runway. And as a bootstrapper I, of course, without infinite runway, quickly became a fan of this direct response marketing, not the brand marketing that folks seem to have been talking. I mean, this is early 2000s, and in the startup space, everyone was talking about building a brand and having Kid Rock at your launch party and literally taking out Super Bowl ads. And I just couldn’t afford any of that. I needed to make $2 for every dollar I put into the machine. And so what that does for you is it gives you a short-term mindset, and that can be both good and bad, right? 

It’s good because it motivates you to build a viable business and a business that generates revenue and profit from the start. That is a superpower of bootstrapping. But it’s bad because it teaches you to think in the short term. And for me, I rarely looked out more than a few months in my entrepreneurial journey. I never looked out 10 years and said, where might I be? Where might want to be? I always looked ahead and said, what’s the payback on these ads that I’m running right now? Can I make my money back in two months or three months? When will the SEO traffic that I’m going for justify all the time I’m investing or when will I make it to 10K a month? I think it was 8K a month actually, so I can quit my day job. And if I’ve learned anything over the past, whatever, a couple decades of being an entrepreneur, it’s to hold two things in tension, that both things can be true at the same time, right? 

It’s to get away from my programmer mindset, very left brain, on or off, binary ones and zeros, and to think, you know what? I kind of need to do both. I need to think in the short term, because I need to make enough money that I can quit the day job or that I can justify all this effort I’m putting into it, not hanging out with my friends, perhaps not hanging out with my family, working nights, being tired around a day job. I have to think in the short term, I need to accelerate revenue so that I can quit that day job or do whatever the other goal is. And also now, and again, I should take a step back and think about what is the next six months, 12 months, 12 years look like? When I talk about playing the long game, I do think about it as a fractal. 

So if you’re familiar with the fractal, if you go to a tiny, tiny piece of the California coastline and you look at it from 100 feet up and then you go to 1000 feet, 10,000 feet, 30,000 feet, the idea of a fractal is that a small piece of it repeating can start to look the same. From 30,000 feet, it can look the same as at 100 feet. It’s a different perspective, but it’s essentially a never-ending pattern. And the idea is that fractals are infinitely complex patterns that are… I’m reading a definition now, self-similar across different scales. Self-similar is interesting. But you get the idea at 100 feet, 1000 feet, 10,000 feet, 30,000 feet, a piece of the California coastline can look different. I feel that way about playing the long game. And what I mean by that is up close, the long game might be a year spent getting your SEO efforts in order. 

Maybe it’s two, and that can be the long game in the short term. But then the long game might be a decade or two, as your whole career unfolds, and you realize as you go that there’s a single thread tying everything that you do together. And looking at that thread and being deliberate about saying, what do I like about this and what do I want to lean into? What am I good at? What skills do I have? What do I enjoy? And doubling down on that when you have the opportunity, you don’t always have the opportunity if you’re working for someone else, you may not, but as you have the opportunity to guide your own career, I think that that’s a higher altitude fractal looking at a decade or two versus a year or two. And one example I want to give in terms of SEO is Ruben Gomez with Seinwell. 

He’s an often requested guest on the show, and a year or two before he launched Seinwell, which is an electronic signature app, he started his SEO efforts. He didn’t have a product, he put up a landing page, he put up a small website, he started working his SEO Magic. There’s secret sauce in there, so I’m not saying everyone could do this, but if you’re just starting out, you don’t go after electronic signature, you don’t go after electronic documents, you go after a smaller niche. That’s why I talk about it and start small. Stay small. You find a niche where you can compete as you’re learning. My first SEO efforts were with Dot-Net Invoice, and it was invoicing software, so I was trying to compete for those terms, but also it was for Windows servers, it was for vb.net, C#. There were all these kind of long tail terms that no one was competing for, and I didn’t need to make a million dollars a month. 

At the time, making three or $4,000 a month was absolutely life-changing. It was a few hours a month I was spending, and while I couldn’t have won for electronic signature, I certainly could rank for the Dot-Net invoicing software or asp.net invoicing application or any of those long tail terms. And so I’m saying this because what I see a lot on social media, Eye Roll, Exhale is a folks bragging about how quickly their success came, probably not telling the full story when they do, but then other folks trying to model that and wanting to seek that. And nothing is wrong with that. I was once an opportunistic young founder as well, and I wanted the success next week or next month. But in most cases, that’s not the way it goes. In most cases, you’re going to put a year or two in just to get enough SEO rankings that when you launch your electronic signature or .net invoice app, it wouldn’t have taken two years to do that. 

But when you launch that app, you have looked ahead and you’ve planned ahead to set yourself up for success. Another example is from season two of TinySeed Tales where Gather, which was focusing on one in two person architecture and interior design firms, they went up market and they wanted to go to five to 20-person teams. And we talked about it and they knew it was going to take months and their estimate, I don’t remember time, I think it was six months or nine months, took them 18 months to get there. And it was a harrowing 18 months. If you go back and listen to that show and then the follow-up, they almost ran out of money a couple times because they thought that they would start to accelerate and grow faster than they did. And playing the long game is leaning into that and saying, “We are going to make it. We are making progress, and there is something up ahead.” 

Now, again, at a certain point, there’s a chance it just wouldn’t have worked, right? When should they give up? Well, we would’ve evaluated. I would’ve asked them, do you have any more ideas? Do you have any more cash in the bank? Do you have any? What are the alternatives? And at a certain point, you have no options, and that’s usually when you quit or when you give up. In the fractal, those are the 100-foot view, right? 1000 foot view where you’re down and you’re looking at a year or two. I think about things that I had no idea how long they would take. But one of them took seven or eight years, and that was an angel investment, my first angel investment I ever made, which was into WP Engine. And frankly, any angel investment, you should think, I’m not going to… it’s probably going to go to zero, and if I get anything back, it’s going to be 10 years. 

That just seems to be the thing. And I didn’t really realize that in 2010, 2011, when I scraped together a couple… 20 grand I think, which was an enormous amount of money for me at the time to write Jason Cohen a check, and I was honored to be part of it, and it paid out a tremendous payout for me. And it’s probably the third most lucrative asset I have ever owned. Maybe I’ll record another podcast about… I have them in order in my head, but angel investing specifically in WP Engine is probably the thing that made me the third most money. The first one, of course, is building and selling software companies. I bet you don’t know what the second one is. But I’ll be honest, I didn’t know it was going to take seven, eight, nine years. I did assume that when I wrote the check, it was going to go to zero. 

And the interesting thing is Sherry and I wrote a lot of angel checks around there. I think we I think it’s 20 or 21 private investments that we’ve made, and most of them are made between 2010 or ’11 and 2014/15. And it’s such a trip now to see those either shutting down or providing returns. I just had no idea, but it really did take that eight to 10 to… well, it’s almost 14 years now, isn’t it? Yeah, it’s incredible. It’s incredible just putting in the time and how things compound. But that leads me to the question of another long ball. Why did Jason Cohen reach out to me? It was a closed round. And if Jason Cohen approached you and said, “Hey, you want to invest my next startup?” Your answer is yes. You figure out how to get the money. Again, I had never made an investment. 

I didn’t really have the money to invest, but I just figured this was going to work. But how did I know him at all? Well, I’d been blogging since 2005, and this is what, six years in, because I wrote Start Small, Stay Small, and he ordered a copy of that book and read it. And when he emailed me about investing, we didn’t know each other. This is, again, 2011, this is before the first MicroConf. He had never spoken at MicroConf. We had never met, I don’t even know if we’d emailed. And he said, “I’ve been reading your blog,” which of course I was reading his at the time, and he said a lot about virtual assistants, “You know about bootstrapping. I’d love to have you in the round, it’s closed round, whatever.” You can scrape together. So how did I know him? Well, he knew me because I was putting in the work. 

I was playing long ball. I was blogging and writing books. How do I know Darmas Shah of HubSpot? Because today, if I emailed Darmas Shah and he didn’t know me, he’d be like… he wouldn’t respond, right? He has so much going on that if you didn’t know him from the old days, he’s not going to respond. This is the same, Ben Chestnut from MailChimp, why do I know him? Eric Reese, Patio 11. Sam Parr of My First Million. Why do I know any of these people? And it’s because I’ve been doing things for 15 or 20 years, and enough of them in public. That’s the key. Now, I’m not saying that you need to go build an audience, start a podcast, start a conference, write books. I’m not saying it’s any of those things. There are people like a Ruben Gomez, like Sean Ellis, Brian Balfour, who they aren’t the audience building folks. 

I know Brian Balfour now has a podcast, but that’s not how they got famous. They got famous by being internet famous in our circles, by being really good at what they do and talking just enough about it that we realized these people are really smart. They did conference talks where we would catch a bunch of new ideas, because they were thinking outside the box. We hear him on podcasts. There’s other ways to do stuff in public. Ruben is another example. Even like Derek Reimer of course was on the Art of Product podcast. Before that, people still kind of knew who he was because he built Drip. And now he doesn’t have Art of Product anymore, and people still know who he is. He’s not doing a bunch of blogging. He’s on Twitter, but you wouldn’t say he’s trying to build an audience, but people learn no and respect you by the things that you ship into this world, and that can be content, but it doesn’t have to be. 

And here’s the thing with doing all of this; you are putting value out into the world, especially if you’re teaching educating. And please don’t be obnoxious and start teaching and educating from day one and saying, “I’ve done this and this is how everyone should do that.” Like, “Oh, I tried freemium and it doesn’t work, therefore freemium doesn’t work.” And it’s like, come on, this topic, there is prior art. Can you at least read some of the prior art and not try something once and then write it off, or not try something once and then say, this is the only way to do it? Because it’s just obnoxious and annoying. However, coming at it from a beginner’s mind and saying, “Ooh, I tried this experiment and this is what worked. What do y’all think about it?” Or, “I tried this experiment and this is what didn’t work and I’m learning and I’m on my journey.” 

There are ways to couch this and talk about it, that as you do become an expert, you can then talk like an expert. But you don’t need to fake it till you make it. You need to fake it till you make it internally to feel confident, but you don’t need to fake it… I hate people when they fake it online, and I know it’s like that person doesn’t know what they’re doing and they’re acting like it, right? So all that said, I think doing some stuff in public, and it doesn’t just have to be content is beneficial for you in the long term. And you might be wondering; Rob, did you know that when you started blogging, blogging in 2005 podcasting in 2010, MicroConf, 2011, TinySeed 2018 and Drip was in the midst there too and hit tail. There’s all these other overlapping things. 

Did I know that the 2005 start of my blog that it would lead me to write four books, put out 700 podcast episodes, start micro comp, all that? No, absolutely not. And I didn’t know what this podcast would turn into when we started it 14 years ago. Almost. I think by the time this comes out, it’ll be within a month of our 14-year anniversary. And no, I didn’t, but I realized along the way that I was onto something. That’s the thing is there’s this book about a startup founder. I don’t remember the name, and the book wasn’t very good, so even if… I remember it not being great, but he built and sold a startup really quickly, and this is probably written in the early 2000s. And it might be even be called Lucky or Smart, that might be the title of the book. 

But in it, he has a quote that I’ve remembered forever. This is 20 years old, and his quote was, “People ask me, were you lucky or were you smart?” And his conclusion was, “I was smart enough to know that I was getting lucky.” I’ve always loved that. That’s how I feel about my career. That’s how I feel a bit about playing long ball is you’re going to wander, you’re going to put in hard work, 700 episodes of a podcast, four books, whatever you want to call it. All these events, 30, 40 in-person events we’ve run. It’s been hard work. Has it required skill to market and building on it? Yes, Of course. Have I gotten a little lucky? Absolutely. And along that way, I’d like to think that I eventually became smart enough to know that I was getting lucky. I’m going to admit Mike and I did… 

I don’t think we realized what we had with MicroConf for the first seven years. We started in 2011. It wasn’t until 2018 that it really hit me what we had built and how hard it is to build a community like that and how you unique of a community it is, and how many people’s lives we changed through this podcast and that event. It makes me feel very weird to say that sentence. I don’t want to feel like I’m bragging. I don’t want you to feel like I’m congratulating myself for patting myself on the back. But I think that was to my detriment for those years that I kept saying, “Oh, it’s nothing. No, it’s not a big deal.” It is like the person you compliment and they can’t take a compliment. That’s kind of how I was with MicroConf. It was just this thing that we did and we show up and the podcaster just show up every week and ship. 

And in 2018, I had left Drip, I sold it in 2016, left in ’18. And we received a seven-figure cash offer to sell MicroConf. And we seriously considered it. And I’ve talked about this on the podcast before, but this was a turning point because I had basically sold everything really to fund Drip and then sold Drip. And so the only things that I had left were a blog, robwalling.com that I hadn’t written an article for in years. This podcast. And those are the things that we had left. And so the idea of selling it all and just moving on into the tabletop gaming space, which is what I was going to do. It sounded kind of appealing a fresh start, and I think it would’ve been one of my deepest regrets in my life if I had done it. I took six months off in 2018 and I went on a founder retreat. 

I talked to Sherry a lot, but I gave a ton of thought about what is the next chapter of my life, potentially the rest of my life look like my professional career anyways? Do I want to be known in the tabletop gaming space, become a game publisher, whatever it is, whatever I was going to do there? It’s a hobby that of course, I would turn into a job so that I wouldn’t enjoy. But on this founder retreat, I went away for a few days and I realized this is what I’ve been doing for free. This is what I’ve had to do for now 13 years. Because I think about starting the blog in oh five as kind of the start of all this for me. I know it wasn’t when the podcast MicroConf started, but it was that idea of I want to be involved in this space. 

I love being an entrepreneur. I love talking about entrepreneurship. I want to talk with other entrepreneurs and just be around them all the time. And there was no community. And so first we built an audience, then we built a community. And it was at that moment in 2018 on this founder retreat where I thought, I’m going all in on this before this. People don’t remember. MicroConf was just an event. We ran once a year and then twice a year in the US and Europe. That’s it. We didn’t even have a Slack channel that lasted year round. There was no state of Indie SaaS, there was no MicroConf YouTube channel, there was no mastermind matching. All the stuff that we’ve launched that people now think about MicroConf as this community. All of that started in 2019, and it was that decision in 2018 that I made with incomplete information, by the way. 

But there was a bit of founder gut and there was a bit of founder vision, right? Hey, this is where I want to go. And also the realization of I think now this is my legacy. And over that next year or two, that’s where this statement of my professional mission in my life is to multiply the world’s population of independent self-sustaining startups. That became the thing. And that’s when I realized, oh, MicroConf does that. What else can we launch out of MicroConf? And we started thinking about the video vault and the YouTube channel and all this and that. During that time, it became obvious. I was writing personal angel checks to Bootstrap SaaS founders, and that’s where the idea of, well, if we raised a bunch of money, we could do that at scale. Because again, in five, seven years I had written 20 checks, that’s kind of the money we wanted to put into startups. It takes so long to come back. 

TinySeed, we’ve written 151 checks. So you’ll see over the past four or five years, we’ve been able to help and impact so many more founders on that mission to multiplying the world’s population of independent self-sustaining startups. And so if you’re listening to this, you might be thinking, how do I know that I’m in the right game, that I’m playing the right long game in the messy middle days? If I’m in the middle of all this, is it obvious? In my experience? It wasn’t until it was, and in fact, in hindsight, it should have been obvious. Someone should have told me, “Dude, do you realize you’ve been doing this basically for free on the side as a hobby for more than a decade?” 

And by this I mean blogging, then writing books, MicroConf, which was essentially run at breakeven. It made a little bit of profit, but the podcast certainly didn’t take sponsorships, actually drew money. It feels like someone should have come along and told me, but eventually I did realize it right in the messy middle, I did this retreat and had this whole realization of like, oh, that’s where it is. And so is it only in hindsight that you can realize that you’ve been playing the right long game? I’m saying this to you as a listener. Are you thinking about what long game you’re playing? Whether it’s that fractal of I’m working on the SEO effort that’s going to pay off, or I’m working on this pivot or this move-up market, or am I thinking more about my career over the long term? What seeds are you planting today that can take you through for the next five, 10, or 20 years? 

What things would you prefer? What seeds would you prefer to be planting? Where do you want to be in that 10 or 20 years? And it’s a big question. It’s often hard to know. It’s that whole metaphor or the analogy. I forget which one of those it is, but it’s the airplane taking off from New York to LA, and making course adjustments along the way as you gather new information. That’s how I think about playing the long game, is you’re not going to know it at the start. And I don’t know that you… you could choose. I tell you what, consider yourself lucky if you choose the long game that you want to play. Because I don’t know that I did. It was more of like, eh, the people are blogging. I’m like, Paul Graham and Joel Spolsky are blogging. I’m going to start writing and see what happens and publish a blog. 

And I spent much time and it was super nerve-wracking. And eventually I took the next step. So I wasn’t choosing it along the way, but at a certain point I did realize, ooh, I really like this and this is fun, and I like this more than most of the other things in my professional career. And so, if you are very certain what long game you want to play, that’s awesome. Congratulations. I wish I was as lucky as you. It definitely took me many, many years to kind of realize that I was already playing a long game. I was in the middle of it, and I looked around and realized; oh, this is the one that I want to keep playing, right? It was really driven home for me in 2018. I will say that during those years though, really starting in probably 2002, 2003, I did start stacking skills. 

And when I think about playing a long game, I do think about are you acquiring new skills along the way, or are you stagnant? I’ve often used the metaphor of which tools do you have in your tool-belt? In marketing, it was like I learned SEO, and then I learned AdWords, and then I learned display ads. Is it a tool belt or a skill belt? Trademark 2024, Rob Walling. Which skills do you have in your skill belt? I hate that word already. I’m not going to be able to use it with a straight face. But you get the idea of… I was thinking back, things that I learned in order are the following hard work. I learned upfront that my parents taught me, “You’re not going to get anything without hard work.” So that was a skill that was instilled in me from time I was very young, and I’m glad they did. 

If you haven’t learned that yet, hopefully me saying it today convinces you of it. But then the next skill I learned really was web development. Two years out of school, out of graduating from… I went to public university in California, and then I learned how to hack together a UI and HTML by reading some books and some online tutorials, and then kind of launched some small efforts that didn’t do anything. And I learned how to blog. Five years after that, I then realized I needed to learn how to do conversion copywriting. I learned it from info marketers, but no one in the startup space was talking about it. And I realized in order to sell anything, I needed to know how to write copy to get people to click or buy or do whatever. So that was about a year later around the same time, how to structure a marketing website. 

I learned SEO. A year or two later, I started messing with pricing, because I had either built or acquired a couple products. I learned AdWords, then how to acquire small products, on and on, until… then, I started leveling up, right? Audience building, writing books, podcasting, in-person events and whatever it is I do today, just being on camera and such. All of this was me stacking more skills into that tool belt. And hard work, luck and skill. These are the three things. I can control hard work. I think most of us can. You put in more hours? Not to the point of being stupid, like a Silicon Valley startup, 90-hour weeks. That’s not what I mean, but you know what I mean. Focused, attention and just doing the work and putting in the time. Luck, much harder to control. Let’s just be honest. You can get luck, or you can’t. 

We can talk about making your own luck, luck surface area, yes, all that’s true, but that is the one you can least control. I think hard work’s probably the one you can most control, and then skills are in between. If I’m playing a long game, am I building skills and learning along the way and getting better at something? Like I just described that long series of things that I learned. Those all point towards me playing this game of building startups and then teaching others, encouraging others, educating others, and now investing in others who are doing the same thing. So I never could have guessed 20 years ago that this is where I’d end up. But I do think that as you’re going along on this journey, thinking about does my next step tie into my last step? Or am I just bouncing all over the place and not building new skills that relate to each other in a way that if I do look ahead five or 10 years, that I’ll be better off playing this game? 

All that to say 700 episodes of a podcast. When I get interviewed, people ask me, how have you done it? How have you never missed a week? And the answer is, I don’t know. I just kept recording. Once we were six months a year in, it was just a thing we did. And I know that’s not helpful, but I will say the feedback loop, what was helpful is there was a feedback loop. We didn’t just record into the void. We didn’t record a podcast over and over with no comments, no feedback, no listeners, no responses. There were signs along the way. The audience was becoming a thing. Hundreds of people after the first year, it wasn’t a lot, but I think we had maybe 600 listeners after the first year. And I had 25,000 RS subscribers at the time and a few thousand on my email list. 

And I was like, this is so not worth our time. But it was fun. I enjoyed it, and people were listening and that had an impact. And then at a certain point, it just became, especially in… I think there were several times between 2010 when we started this in 2018, where I thought just throwing in the towel and ending it. And I have never thought that since 2018, since having that big reckoning with this is what I do now. And I don’t think we should feel that way necessarily about companies we start. I think all of us exit, right? Everybody sells eventually. And I don’t think that we should be so attached… like starting a software company and then being that attached to it, I think see the talk from Dr. Sherry Walling a few years ago where she talks about how founders look at their logo and it stimulates the same part of their brain as when they look at pictures of their kids. 

So kind of literally lending credence to the idea of, oh, my startup is my baby. And it’s not super healthy. It leads to emotional entanglements that I think are not the best. But with a podcast or with something that I do think I’m going to do for a long time, am I going to sell the podcast? It’s not a SaaS app. So I think I’m able to manage that. It is more a reflection of me than I think a SaaS company should be for most founders. All that to say, thanks for being along on this journey. I almost didn’t record a special episode this week, because it just happens to be an episode with two zeros at the end. But I do feel like reflecting on progress and giving thoughts are warranted, and I think celebrating your victories… As much as I tell you to celebrate those victories, whether it’s on your own or whether it’s with that spouse or significant other who has been by you, your original investor, your first investor, as Sherry says, if I tell you to do it, then I need to do it too. 

And so here’s to 700 episodes of this podcast. Thank you so much for being along with me on the journey from the early days of Mike and I recording them together, to the transition that I thought might implode the podcast back in 2018, through the interviews, the solo episodes, the format changes, the audio quality changes, all manner of craziness. I really appreciate you sticking around. It means a lot to me. I wouldn’t keep recording if it didn’t impact people. These days, I don’t do things that I don’t think are impacting the broader entrepreneurial space and that are impacting folks like you. So thanks for being here this week and every week. This is Rob Walling signing off from episode 700.