Episode 742 | Normalizing Hard Things, Facing Your Biggest Threat, and Making it Fast (A Rob Solo Adventure)

Rob Walling:
Welcome back to Startups For, the Rest, Of Us. I’m Rob Walling. I’m on a solo adventure today and I’m going to be covering topics ranging from normalizing, doing hard things about just getting used to doing hard things about how bisons walk into storms. Not sure if you’ve heard about this, but it’s an interesting adaptation they’ve developed over hundreds or thousands of years, and then about making it work, making it right, and making it fast. Before I dive into that, the Kickstarter for my new book Exit Strategy, the Entrepreneur’s Guide to Selling Your Business Without Regret is Live and it closes next week on December 12th. You can head to the link in the show notes or you can go to kickstarter.com and search for exit strategy. The book is 260 70 pages of all the knowledge that my wife, Dr. Sherry Walling, who is a founder and executive coaching consultant and myself have gathered over the past couple decades of working with entrepreneurs, advising them, investing in them and having had an exit or two ourselves. 

So you can head to exit strategy book.com and also get a link to the Kickstarter there. It would mean the world to me if you’d back it. And also I think that everyone, whether you’re just starting out or whether you’re thinking about exiting or in the middle of exiting, can use some mental support, psychological support and really learn from not only Dr. Sherry and I, but the 15 or 20 entrepreneurs who have exited that we interviewed for this book. So I’m really proud of what we put together and I think for $30 it’s quite this steal in terms of the amount and the quality of the information that you’ll gather from it. In addition, MicroConf mastermind applications close on December 4th. You’ve heard me talk about Mastermind’s ad nauseum on this podcast about the tremendous impact that they’ve had on my entrepreneurial career, not only in the moment, but just keeping me going for the past couple decades. MicroConf masterminds.com if you want to get matched with like-minded founders who are bootstrapped and mostly bootstrapped but ambitious and looking for accountability, friendship, comradery, and frankly just looking to not feel so alone. So that’s microcom masterminds.com. 

Let’s dive into my first topic of the day. I want to tell you a story about a trip that my track team took to Hawaii in high school. I think I was a junior and this was a big deal. None of us had ever been to Hawaii and we went out there to compete in an invitational type thing, but we had to do fundraisers and such to afford the tickets and all that. And while we were out there one day, my coach was driving the rental car back to the hotel and the hotel was surrounded by, I think it was all sugar cane if I recall correctly. And there was this long road, of course it’s Hawaii, so there’s a mountains on this side and a beach on this side and just this amazing vista. But he’s driving back to the place that we were staying at and he sees one of the distance runners running the other direction running away from the hotel, and he’s just kind of trotting along and his name’s Brian. 

And so coach pulls up and he says, Brian, where are you going? And he says, I’m running down to this convenience store to get ice cream. And the coach says they have ice cream back at the hotel. There’s a refrigerator thing where you can buy it in the lobby. And Brian says, yeah, but they don’t have chocolate chip. And my coach told that at the end of year event, the reception where parents get together and talk about track and give people awards and all that, and I got a huge laugh from all the parents because the convenience store was a couple miles from the hotel and us track athletes. We looked around. I don’t get why that’s funny, and I get the joke now. It’s that wow, as an adult would you run two miles in order to get a thing of ice cream that is the flavor that you want? 

And most of the time, no you wouldn’t. But the thing was is when you’re running at that level, we were competing at a pretty intense level. I’ll say I wound up, I’ve talked about this, but I wound up breaking the school record in the hurdles and that record lasted 31 years. It just got broken this year about four months ago. So we were not dabbling in track. We were very, very intense about it, and as such, we had normalized doing hard things. There was such second nature that most of us didn’t get the joke when the coach told that story at the end of your reception. And the thing about it was our workouts were a mile warmup. Then you do some stretching and then you do a pretty intense workout of sprints and intervals and you’re dying at the end and then you do another mile cool down, you stretch and you leave. 

And that’s just what we did five days a week, sometimes six days a week. There were obviously days when I threw up once a week during the fall for a few months As you’re getting into shape, it’s just so intense and that was just what we did. We would groan when they would name a particularly hard workout, but we all showed up and we all did it, and the people that performed it was just expected that if we wanted to do great things, we had to do hard things and usually we had to do the hard things first. It was getting in shape and it was working on our technique and it was sometimes running ourselves to the point of throwing up, unfortunately, but in the end of the season when you’re trying to qualify for regionals and the state meet, you were thankful that you did the hard things in the early days, and there were some folks that came to the first month or two of track and it was hard and they said, you know what? 

This isn’t for me and that’s fine. It was a way of I guess weeding folks out and really only having those that cared enough to do the hard things that were really committed to the long-term vision because talk about delayed gratification, and I guess I should clarify, in high school it was only about, was it maybe five months? So it was probably from January to June you started working out and then you had the state meet in June in college was when there was fall workouts, and that went all the way through June, so it really was a full nine months or so of doing hard things, so to speak, and you kind of did it every day and got used to it. The reason I’m bringing this up, of course, in the context of startups is a lot of the founders that I see succeeding if they’re not relying on luck and they are the ones who are executing and building skills and putting in hard work, it’s just expected that you’re going to have to do some hard things. 

And sometimes that hard thing is digging into marketing approaches that don’t work right away or maybe that you’re like, I don’t really want to do that. Do I have to do SEO? I don’t really want to do the ground. I don’t want to do sales demos. I don’t want to focus on one product and push that boulder up the hill. I don’t want to try to run ads. That doesn’t sound interesting. The way my mind works is I really want to build a media company. Well, I just start a YouTube channel and be on Twitter and tweet about things and have that build my business. I don’t want to hire people. I don’t want to have to fire people. I don’t want to make the hard decision of having to focus on one thing. I don’t want to do b2b. That sounds boring. I want to build a two-sided marketplace. 

I’m not saying that’s not hard, that’s actually doing it on hard mode, but you get the idea. I get emails to this podcast about I have a good day job and I’m making good money, but I really want to be an entrepreneur, but I just have a tough time getting motivated. And I think to myself, then you don’t really want to be an entrepreneur and that’s okay. That’s okay. Just know that if you’re going to do this, you have to do hard things. I was in conversation with someone who had sold their company for nine figures, so that’s hundreds of millions of dollars. And one of the things that he does is talk to other founders who have exited for never have to Work again, money. I call it sunset Money. You can ride off into the sunset. Some people call it FU money, and that’s fine too. 

It’s all the same. And he said one of the big things he encounters, and this is similar when I have these conversations with folks, one of the hard things is if you sell your company for whatever that number is for you, maybe it’s 5 million for you, maybe it’s 10 million, maybe it’s 50 million. You sell your company, you’ve been grinding, you’ve been creating, you’ve been building, and you have all this money in the bank, and it’s really hard to figure out what to do next. That’s meaningful, but not so hard that you’ll just give up because when you have that much money in the bank, why do hard things? What’s the motivation anymore? So many of us had the motivation to build these companies of I want to build interesting things. I want freedom. I want to be in charge of my own time, and basically that means I have to get rich in order to do it. 

But that becomes a motivation for a lot of people. It’s not to get rich. It’s the freedom, right? It’s the ability to build and work on and do whatever you want for the rest of your life, and that is an amazing place to be in. Now the challenge is your motivation to stick through the hard times and to do really hard things like the mile warmup, the mile cool down, and the really hard workout in between or to grind for months and months on SEO or ads or focusing on a product, trying to find product-market fit, and staying up at night thinking, am I ever going to find product-market fit, dealing with an employee who doesn’t work out and you have to fire and rehire. There’s all these things that are difficult, that are challenging and finding that motivation, whether you have enough money to make to never work again, or whether you don’t and you just want to be an entrepreneur, but you don’t feel that drive enough to push you to want to do really hard things. 

It’s a challenge. And so I tell this story about Brian running two miles to a convenience store to grab chocolate chip ice cream. He did return with chocolate chip, by the way, and there were a couple people that wasn’t just Brian who wanted it. There were some parents or something that wanted chocolate chip, and when he went, he walked out in the lobby and they didn’t have it. He just took off. He didn’t even go back and ask him. He just left and ran a four mile round trip to get chocolate chip ice cream for these other people. So I hope that anecdote has you thinking about the hard things that perhaps should be normalized in your day today. My second topic for today is a fun fact. I heard the other day, and then I confirmed it with not only chat GPT, but with Google as well. 

And it’s about how a pack or a herd, technically speaking of bisons, if they see a blizzard coming or a storm, they will walk into the storm because they know that whatever direction the storm is headed, it will go by faster if they are moving into that storm. And think about that, there’s some type of really deep adaptation that has gone on there because I think for most of us, we don’t want to walk into the storm and most animals will run away from a storm or from danger or from something that is perceived as uncomfortable, but the bison knows that if they take this big challenge head on, it will be over faster. Hopefully. The parallel to running a startup is really obvious. What are the storms? What are the blizzards that are coming at you? The lack of product-market fit, the lack of growth, impending competitors that are going to eat your lunch. 

Ai, a rapidly changing landscape. Folks who can spin up a similar app to you in a week now because of copilot or cursor AI or all these coding tools, people building stuff with no code that is purpose built and perhaps solves a need better than your custom app that you spent years building can. So what do bison know that we don’t? Well, they know that if you ignore a threat or if you walk sideways or away from it, you’re just going to experience it longer. It doesn’t actually fix anything. And you as the startup founder or an aspiring startup founder, I think would be well-served to figure out what are the big things that make you uncomfortable, the things that stress you out, the things that keep you up at night. And instead of trying to ignore them, trying to run away from them, trying to hide from them, think about how can I attack this head on? 

Whether this is someone working for you who just isn’t quite working out and you let it go way too long. That’s a very common thing. The startup founders do. All of us do it at one point or another in our careers and all of us come to regret that decision of ignoring it is not a threat in this case, but I mean it’s a threat to our growth. It’s a threat to our business. It is just a hard thing that’s easy to ignore. Another hard thing is lack of growth, and your R is not going up into the right. Do you make excuses? Do you blame the internet? Do you say, oh, startup advice doesn’t work anymore? Well, in 2024, it doesn’t work the way it used. You used to just be able to do SEO content and AdWords and everything would just work out, and it was so easy, which in fact it wasn’t. 

But you convince yourself of this because you’re not having success, or is it hard and you need to figure out which direction to head and you need to persevere long enough and normalize doing hard things. Ooh, see the way I integrated those two but normalize running the four mile round trip to get the chocolate chip ice cream in order to face these things that are difficult. If you’re always running away or ignoring or making excuses or acting like these hard things don’t exist, you’re not going to find success. I can’t think. Now, maybe there’s an exception, but I can’t think of a single entrepreneur that I have worked with, advised, been around, invested in, and I’m invested now in, I think it’s 212 B2B, SaaS companies can’t think of a single one that has achieved success. And we can just say, what is that? I dunno. 

Seven figure and up a R seven figure eight, figure a RR. Can’t think of one that ignored these hard things that didn’t accept their current reality, even if that reality was not what they wanted to hear and didn’t make a game plan a, plan a, plan B, a plan C of how to deal with and address it. I’ve known founders, multiple founders that have received cease and desist letters. I know multiple that have been sued. I know many that have been threatened to be sued. I know several that have been hacked where their app has been hacked. There has been ransom situations where I’m going to release this on the dark web if you don’t pay us X amount of Bitcoin. I’ve seen embezzlement, I’ve seen employees rogue. The list goes on and on, and whether it’s any of those or whether it’s something as simple as, oh, hey, we’re not growing, and that’s the storm, that’s the coming storm is that if we don’t grow for too much longer, we’re done. 

We either have to lay everybody off or the app itself. We just need to shut down the company. That has to be the hard reality that you face on a day-to-day basis. And I am not trying to paint entrepreneurship as this terrible hard thing. You have to work 60 hour weeks all the time and be stressed. That’s not how it should be either. If it’s that hard, either you’re trying to build a billion dollar company or maybe your approach isn’t quite right, or frankly, maybe you’re running into some bad luck, but it doesn’t have to be hard all the time. I just want to level set for you listening that there will be ups and downs and when the ups are here, celebrate them. And when the downs are here and the difficult times are present for you, realize that that is part of this game. 

That is part of being an entrepreneur and learning and being willing to face those hard things head on is something that I wished I had learned sooner, and if only I had learned this tidy fact about bisons walking into storms years ago, perhaps I would’ve been better equipped. And that’s what I hope to convey to you here today. So I hope you continue your entrepreneurial journey a little better equipped to do so. My last topic for today is about first making it work, then making it right, then making it fast. And this is a quote or a paraphrase from the Comic Lab podcast that I have quoted in or paraphrased several times in the past. You can go check it out if you’re interested. But the co-hosts I find are very practical and pragmatic and the number of parallels between being an independent comic artist, which is essentially being an entrepreneur and making money from your art. 

Now it is B2C, so it doesn’t necessarily fit in the focus of this podcast, but a lot of what they talk about I find has parallels in the startup space and specifically in the bootstrapped and mostly bootstrapped SaaS space. So one of the hosts, Brad had this quote. He said, first, make it work, then make it right and then make it fast. And the context he was using was about art, was about drawing or writing frankly, anything that you would do to produce a comic strip or a comic book or a web comic and about how when you’re just starting out, just learning to draw or learning to write and be funny is hard. And so it might take you, it probably will take you years just to make it work, but you’re going to be really slow at it and it’s not going to be that good. 

So then the next step is you’re not that good at it, but make it good. That’s the making it right step. So I think it’s like make it work, then make it good and then make it fast. But he says make it right. And I can say that, look, it’s his phrase. He can name it whatever he wants. So first step is to make it work, then you make it right and then over repetition, you make it fast basically. And I actually like thoughts or frameworks or statements like this that make me think, oh yeah, that’s totally obvious, but I didn’t say it. I haven’t heard it phrased this way this succinctly before, but I think the parallels run deep. I think this podcast, if you go back and listen, the first 20 or 30 episodes, maybe 40 or 50, we’re just trying to make it work. 

And we did shipped every week. There were a couple months where we shipped every other week, but you get the idea over the 14 year lifespan of this podcast and the 742 episodes, the first 20 to 40 were making it work the next, I don’t know how many were making it right? And then eventually we got to the point and later me on my own got to the point where I can record these really fast. That took repetition. That didn’t happen in the first a hundred episodes. The fast part was probably in the second hundred or maybe the third a hundred, frankly, these solo episodes. I didn’t start doing these until several hundred in, and those were excruciating and painful at first, and then through repetition, I made them write and made them fast. Same thing. If you’re writing and giving conference talks, your first one’s not going to be that good. 

You got to make it right. And then over time you get better. To the point where I’ve given talks that I have literally built the slides four days in advance and run through the talk once, and then I get up on stage. And that’s just pure repetition because the first talk I gave, I was working on weeks and weeks in advance, and I was practicing over and over because I didn’t know how to do it well, and I didn’t know how to do it fast. It’s the same thing with sales demos. First time you do it, it’s not going to be very good. You’re going to be super nervous and you’re going to potentially over prepare, spend a lot of time on it, and then over time, over repetition, you make it so it’s good. The making it fast maybe doesn’t apply here, but I do think maybe making the deck for your sales demo applies, right? 

That you would get better a second time building a deck for it. Marketing approaches similar. First you just kind of stumble through and you don’t know what’s going to work, and eventually you make something work just enough that it keeps you alive for another month and then you start getting better at thinking strategically and about thinking like a marketer. And then eventually you get to the point where you can spin up new marketing approaches. I’ll say quickly, right? That’s the fast part. Now the analogy doesn’t necessarily hold up. It’s not a piece of art. And so thinking that you can spin up five or six marketing approaches just because you’re good at it isn’t reality in most situations. Most companies don’t have that many, but you get the idea. You do get better at moving fast and doing a lot of things. A r and I talk about the most successful founders across the tiny C portfolio of 192 companies are those founders that do a lot of things relatively quickly. 

They put a lot of things into the world, and they’re right enough of the time. And Ruben, the founder of Sewell, mentioned to me that he liked that analogy, but he felt like I was leaving something out. When I say that the founders who do a lot of things and are right enough of the time, and I think enough is 50, 60, 70%, it’s somewhere in there and there’s asymmetric upside when they are right? But Ruben was saying, yeah, but even those founders, one of ’em for sure, even those founders that do it, they’re not necessarily right immediately out of the gate when they try a new thing. Usually it’s off a bit. And every approach needs to be honed unless you get really lucky, you launch a new sales effort, a new marketing effort, a new landing page, a new feature, a new product. 

You hire someone new, there’s a certain level of refinement, maybe some experimentation, but of putting something into the wild and realizing, oh, that’s not quite right, and I need to tweak it according to my founder gut and according to the taste that I have in my mind of what a landing page should look like or what a feature launch should be or how a marketing approach should be executed, I’m going to take the signals that I’m getting back and there’s a feedback loop and I’m going to iterate, I’m going to tweak. And then eventually, you’re right enough of the time. So don’t think that right out of the gate, founders who are doing exceptionally well are just right all the time, but you do build your founder gut. I use this phrase all the time, and the editor for the SaaS Playbook was like, that’s not a real thing, and it has to be founder’s Gut, right? 

It’s a possessive that the founder possesses this gut instinct. And I was like, I guess, but almost it’s like capital F, capital G, it’s like founder gut. It’s a thing that I name of over time, you can develop this. Some people probably have it from the start. I think like Jason Cohen Heat and Shaw probably Dharmesh. There’s some people that I know David cancel that at least as I saw them going on their journey, they just seemed from the start to kind of know what they were doing and to generally work on the right things with asymmetric upside ship, a lot of things really smart people. I was not that I was stumbling around blindly for years and years in my twenties and early thirties, not really knowing what I should be working on. And my founder gut was not great. And the way that I developed it was through people giving me advice. 

People that were ahead of me, watching people who have really strong founder guts and seeing how they made decisions. It’s just a refinement and a learning and an iteration of myself, a constant search for self-improvement. And part of that I’ve talked about on the show in the past, which is knowing yourself not having blind spots. We all have weaknesses, but a blind spot is a weakness that we’re not aware of. And so even taking the personality tests, the Enneagram and the StrengthsFinder and the Kolby A and there’s a few others, do those unlock everything and all the magic to make you a high performer? No, but they give you one more data point, and if you can read through the descriptions and say, oh, yeah, the strength side of this certain attribute is that I really focus on things and I really focus and get it done. 

And the shadow side of that is I focus too long and I spend years working on stuff that isn’t working. And knowing that about yourself goes a long way towards helping you improve as a founder and improving your founder gut. Now back to first making it work, then making it right, and they’re making it fast. I do see people try to skip this and they see much like in the stair step method, I often say, Hey, if you see folks that are playing in the major leagues and you haven’t played T-ball yet, you don’t want to go try to play in the major leagues right away. You want to play T-ball and then little league and then junior high ball and high school ball, college ball, minor leagues, major leagues, right? There’s a bunch of steps along the way, and I see folks, I guess it’s on Twitter, I hear ’em on podcasts, whatever, who see an entrepreneur that is 5, 10, 15 years ahead of them or someone who has assets that they do not such as, well, you have half a million Twitter followers and I have 500, but I’m going to try the same approach because that surely that will work. 

It’s like trying to jump to the end without putting in all the time to first make it work, then make it right, and then make it fast. I mean, what’s interesting about this phrase is just how much it does align with the stair-step method. It hadn’t occurred to me until right now as I’m saying this, it’s crawl, walk, run. Don’t try to run from the start. Don’t try to play major league baseball from the start. Don’t try to quit your day job and have a burn down of all your money. I had six months to launch a standalone SaaS and get traction. I’ve never done this before. It’s like, well, hold on. How about you make it work by just launching anything? And whether that’s a plugin in an app marketplace or an ecosystem, whether it’s an ebook or a course or whatever, just build enough of an audience or learn to market well enough or build enough of a network that you just get something out there and then get better at it, right? 

That’s the make it right. And look, that might take a few years. This is why I say think in years, not months. As an entrepreneur, as a bootstrap founder, especially think in years, not months, don’t be in such a hurry to get to the end result because then you’re trying to jump to the make it fast. And that’s where this ridiculous idea that I should spray and pray one thing every week. I’m going to launch 50 apps this year and just see what sticks. I’m going to see what’s going to make it work that’s wanting to get to make it fast and take a shortcut to get there and not do the learning and not put in the hard work and not face the hardest things that are the blizzard that is marching toward you. And I think people that are trying to skip the line and get there are doing themselves a disservice and are much less likely to be able to repeat it again in the future, are much more likely to need to rely on luck and are much less likely to succeed in the longterm and to be able to do it again, even if they do. 

Now, am I saying you have to grind it out and put in years. It’s like you got to go through high school and then you got to go through university, and then you got to go through, get your master’s and then your PhD, and then you got to work 10 years before you have seniority. So that’s just what we all did. And so you got to put in 20 years. No, that’s not what I’m saying. Obviously the beauty of entrepreneurship and what we’re all doing is you don’t have to take the same path that anyone else did. But I do see early stage folks making the mistake of thinking that they can just jump to the make it fast. They can just jump to that end. But if you can’t make it work and make it right, it doesn’t matter if it’s fast because you’re shipping something crappy, and whether that thing that’s crappy is a product or ebook or whatever it is, if it doesn’t work and it’s not right, what’s the point of trying to make it fast? 

I gave a talk after I sold Drip, and it was called 11 Years to Overnight Success, and it measured the time from launching my first little micro product wound up doing a thousand, 2000, 3000 a month until Sunset Money, right until selling Drip and never having to work again. And the title was Tongue in Cheek, obviously 11 years to Overnight success because people think this stuff happens overnight and almost without exception, or maybe without exception, it doesn’t, doesn’t happen overnight, crawl, walk, run. You stair step your way up, you first make it work, then you make it right, and then you make it fast. Thanks so much for joining me this week and every week on the show. If you keep listening, I’ll keep recording. This is Rob Walling signing off from episode 742.