Ep. 67

8 Lessons from 8 Years Building a Bootstrapped Business with Interact CEO with Josh Haynam

It has been eight years since Josh and Interact’s other co-founders sat in a pizza shop, discussing their college graduation that was just around the corner. At this point, Interact was just a fledgling idea that had yet to make any money. But that night, Josh looked at them and said, “Sooo, you guys want to work on this full-time when we graduate?” And without blinking an eye, they were like, “Yeah, we’re in.”

Since then, Interact has grown to millions in revenue with an amazing team, making a real impact in the world of marketing. On this episode of Creator Stories, Interact CEO Josh Haynam shares the 8 biggest lessons they’ve learned through the years. 

Read the blog: 8 Lessons from 8 Years Building a Bootstrapped Business

Jessmyn: Hey, and welcome to Interact’s Creator Stories podcast. Interact is the easiest way to convert curious people into loyal and happy customers by using a lead generating quiz. On Creator Stories we get to hear the entrepreneur’s journey. This is a podcast about how those creators took their knowledge and experiences to carve out a place in the world, owned what they know is special about themselves, and turned it into a successful company. I’m here with Interact CEO and co-founder Josh Haynam, who writes a ton of articles for the Interact blog about his experience building a software company, and how he takes care of his own mental health.
For this season, I picked a few of my favorites, so we can dive deeper into those topics. And today we’re discussing the article Eight Lessons from Eight Years Building a Bootstrap Business. You can grab the link to the article in the show notes or visit our blog at tryinteract.com/blog. All right, let’s get started. All right, so Eight Lessons from Eight Years Building a Bootstrap Business. So Josh, tell me what is a bootstrap business?

Josh: Yeah, it’s a good question. We were chatting before, and I was like, “No one has ever asked me what that means,” but it’s such a weird word, because bootstrap, I just think about I grew up with a bunch of… Well, we grew up close to each otherish in the Central Valley, and I think about cowboy boots with the spurs on the back. Do you remember those? People used to wear those, and it’s like-

Jessmyn: Mm-hmm, and they would spin in the wind.

Josh: Yeah, they’d spin, and they’re really spiky. And I always thought, I’m like, “What if you’re walking behind somebody that’s wearing those, and you accidentally kick it? You’re just going to be bleeding.” So that’s what I think of.

Jessmyn: Isn’t that the though?

Josh: That’s what think of when I think of Bootstrap Company. That’s not what it is. I mean, it’s basically I think the better word is self-funded, because I mean, there’s different schools of thought around bootstrapping a business, but I mean, no company gets by without any sort of funding. So bootstrap really means you’re just funding it yourself. And in our case, it came out of basically Matt, and Matt is our CTO and co-founder, our salaries the first three or four years. We just didn’t really make a salary, and so it was funded by the delta of what we could have made working at a company for those few years, and then over time it kind of evens out. So I think that’s what it really means is you’re funding it yourself, whether it’s with money that you already have or with foregoing salary, something like that.

Jessmyn: I love that. And I think that’s a good question, because I know we’ve said it in the time that I’ve been here, and at first I just pretended that I knew what it meant, and now I have a more formal definition. Just kidding, it didn’t take me five years to know what that meant. So before I go into sort of your guys’ experience having a bootstrap business, let’s go over some of the eight lessons that you had discovered throughout the year, and that you’ve written in one of our blog posts. I actually have them written right next to me. Do you want me to go through all of them?

Josh: Yeah, because I’m freaking out, because I can’t remember all of them. I’m like, “That’s really bad.”

Jessmyn: Pop quiz.

Josh: I wrote them, and I’m like, “hmm, I’m getting older.”

Jessmyn: Yeah. No, I hear you. Okay, so I’m going to run through all eight, and then I figured we could go through each and every one of them, because I probably will have questions along the way.

Josh: Yeah.

Jessmyn: So first and foremost… Actually, quick question before I do say this. Did you put this in a particular order, or was it just whatever came to mind first?

Josh: Yeah, it took a really long time to write this post. I probably wrote it over nine months.

Jessmyn: Wow.

Josh: And I kept changing it around, because I was like, “Do I want to rank them?” So it’s not ranked.

Jessmyn: Okay, in no particular order.

Josh: That’s the answer. It’s an unordered list. I’ve been learning some programming on the side, and it’s a UL is the tag, unordered list.

Jessmyn: I love that. Okay, so number one in no particular order is ask the scary questions. Two, persistence wins over everything else. Three, in the beginning you can only serve one type of customer. Four, mentors matter. Five, working with the right people is the only way to scale. Six, be the best in the world at one thing. Seven, people over profit is sustainable and happy growth. Eight, the company follows where your mind leads. Do those ring a bell?

Josh: I remember now. Which one do you want to start with?

Jessmyn: I want to start with ask the scary questions. I guess I’m just very structured, so it’s the first one.

Josh: That works.

Jessmyn: But what caught me with ask the scary questions is I guess, of course, what are the scary questions, and also what’s the significance of it?

Josh: Yeah. And I’m curious to hear having been here for five years now, what your perspective is on asking scary questions too. For me, what I thought of when that one was bubbling up is we’ve run into a lot of points in the business where growth slows, or people aren’t becoming customers, or they’re not using their quizzes, or they’re having a lot of struggles with the quiz on the back end, or whatever it is. And I think the tendency, I don’t know why this is the tendency, but the tendency is just to try to pave over that, and just move on, and be like, “Okay, well, we can find somebody that will want to use it.” And some of that’s true, and this is why I think everything is an and, like all the Jim Collins books like Good to Great and Built to Last. Everything is an and, because you do have to figure out the answers to those scary questions, and you also have to focus on your customers who are having success with your product.
But I think there’s times where I think in particular the years where this resonated, and this was just before you joined. We had two back to back years of really pushing hard on doing outbound sales, and we wasted so much money and time on that and effort for pretty much two full years and probably a few hundred thousand dollars wasted on that, and we never really asked, “Why is this not working? What are the problems?” We were just like, “Well, everyone says to send more emails. We’ll send more emails.” So that’s really what comes to mind for me, and the thought behind that.
And then once we did, right? And this is where you came into the picture, is we figured out sales just isn’t going to work, at least not with the way this business is set up. It might work with somebody else who’s doing quizzes, but not for us. So then we pivoted and started doing partnerships instead, and then that has been a big part of the growth we’ve had over the last five years.

Jessmyn: Yeah, actually, I mean, mine is sort of similar, but it’s more from a marketing perspective, I guess, in it’s similar in that it’s still like what went wrong? Why do people feel this way? But it was more of if they didn’t want to partner with us, or if they didn’t want to use us as their tool, why? And actually having to go out and ask those questions I think is the scary part versus wondering, and you always want to think that, “Oh, what I’m doing is great, and I have a beautiful mind. I’m brilliant,” but sometimes it doesn’t work out that way.

Josh: Yeah. I mean, that reminds me of another story now that you mentioned the marketing stuff. The first time I wrote our course, which was just rewritten and is beautiful now, and super comprehensive, and very… You can probably resonate with this too, but the first time I wrote it, all the feedback was just like, “This is too long. This is way too complicated.” And it’s hard to ask those questions, and sit there, and be like, “Okay, why? Where are you getting stuck? How far did you get before you felt like this was too long?” And it’s the same kind of thing as what you’re talking about where it’s like, “Okay, why is the product not working for you? What do you need it to do, or how do you need it to function?”
And then you have to drill a layer deeper, because there’s always an easy answer, right? Which is like, “Well, just build this feature,” but it’s really usually not the actual answer. The actual answer is, “I need it to do this function, and I need to figure out how that works,” and so then you kind of have to drill way down. And I think that’s why asking the questions you don’t want to know the answers to, that was the alternative title was ask the questions you don’t want to know the answers to, because sometimes the answer might honestly just be the way you’re approaching things is totally wrong, and then to your point about the beautiful mind, then you’re like, “Well, sure, I might have a beautiful mind. I might be able to figure stuff out, but a big percentage of the stuff that I figure out is not going to work, and that’s fine. It doesn’t mean that I’m not smart.”

Jessmyn: But there’s also sort of there’s this… Oh, gosh, I don’t really know how to word it. Is it sort of imposter syndrome, like you think you have such a good idea, and someone tells you actually, “I want it to work this way, or it would be better if it was this way,” and now you feel that the ideas that you have aren’t as good as what you thought it was?

Josh: Yeah, I don’t know. I guess imposter syndrome could be it. I think the one for me that really hits is when we’re not growing, because then I start to second guess everything. I’m like, “Well, we have these values, right?” And if we skip around to the last one and totally ruin your orderliness, the last one or the second to last one, people over profit, and then the last one, the company goes where your mind leads, those are the ones that start to feel really hard when we’re not growing, because I look around, and I see companies that are doing things that don’t put people first, and just treat everyone like a number, and whether it’s misuse of data, or strategies that are just kind of slimy, or whatever it is, right?
And then I start to be like, “Well, is this even right? Does this stuff pay off in the end? Because it doesn’t feel like it right now.” And that’s another hard one that you can kind of internalize when faced with whatever I’m trying is not working. Do I really believe what I actually think I believe and what I’m telling people, or does it just not even work?

Jessmyn: I guess that does bring up a question in terms of saying people over profit, company follows where your mind leads. How do you sort of… Oh my gosh, this all comes together. I guess it also brings in sort of persistence wins over everything else, but how do you kind of keep going when you feel that your ideas aren’t that great or as great as you thought it was, you’re not making the profit that you wanted, you are helping people, but it’s just not the numbers that you thought you would be doing?

Josh: Yeah, I mean, really the only things I think that stick through all of that is one, actually enjoying whatever you’re doing separate from the numbers. So my thing is usually writing. That’s kind of my default, and then also product development. I love solving problems by writing out designs for product and just figuring out how can we make this thing that is hard easy using technology. So those two things are kind of the fallbacks, and that was the thing at the beginning of the company, and then also throughout time that’s not the only time we’ve struggled to grow. We’ve had lots of ups and downs, and so in those down curves, I think for me at least, it’s about falling back on what is it that I actually enjoy, and that I can see improvement on too.
If you write every day, and you’re getting feedback on your writing, it’s going to improve regardless of whether anybody is really reading it, or if it’s driving the bottom line, or whatever. I think that’s a really important skill in my opinion, and I feel like you’ve probably had to deal with that too, right? Especially with this podcast where your recording stuff, and it doesn’t even go out for several months. What’s your method for when you’re not seeing the immediate results of your work? How do you stay motivated?

Jessmyn: Yeah, that was tough, because, well, it started with when you had the podcast you were able to go record every week, and it would go out the next week, and I could not keep up with that same schedule. So that was of my first hit of, “Oh, no, I’m not as good at this as Josh thinks I am.” And when you were so open, I guess, well, let me lead to my answer, but you were so open about, “Hey, whatever works for you is what you should do, and I trust that, that it’s going to work out the way that it should, and it’ll grow when it grows. And for me, that’s sort my answer is having a support system in which someone can back me up of, “Hey, it’s okay that that’s how your brain works, but just keep going and be consistent with that method, and it’ll all fall into place when it needs to.”
So that then gave me sort of it opened up my mind in a sense of, “Okay, so if I can’t do one a week, push it out the week after, because that schedule is kind of insane for me. What makes sense?” So I figured out a schedule. This is my structure, very orderly type of brain. I had to figure out a schedule of if I record for four months straight, and then I get a few months off, and in that time, we’re editing and reaching out to the guests who are on the show, schedule them out, and then we can schedule and create all of the graphics for the marketing, and then it’ll all fall into place, and that gives me a few months of decompressing and going from there. And so far it’s been great.
I think we’re at… I looked at it. It’s sitting on my desktop, and I’m looking at it right now. I don’t know what date this came out, but last time I checked we’ve reached 4,500, probably a little closer to 5,000 now downloads since we started the podcast, which was pretty big for me, because you think about it, and that’s how many times people have listened to me talk.

Josh: Yeah, well, and I don’t know if you’ve seen this stat, but 90% of podcasts never reach 3,500.

Jessmyn: Wow.

Josh: So that puts you top 10% just by crossing that number, which is crazy.

Jessmyn: Oh, Wow. I had no idea.

Josh: Yeah, yeah. And I think that point about how your mind and how your process works versus my process, and then the rest of our team each has their own process. That’s one of the middle points of the team is it’s sustainable and happy growth, and I think in my view of things, sustainable often is the results of different perspectives, and personalities, and approaches working together, because while I can go really fast, and this has been Matt and I’s dynamic since the beginning, I can go really fast, but I’ll also burn out. I can put out a podcast every week, twice a week, whatever it is for three months, but then I’ll burn out and not do anything for three months.
Whereas he and I think your style is more like this too, will slowly build, and it’s much more methodical, and it’s like, “I’m going to plan this out. I’m going to see what the next six months is going to look like. I’m going to execute on it,” and then you’re building in your rest ahead of time, whereas what I’ll do is I’ll just burn out and then have to rest. I’m Working on it, but I think that is a big part of it too, bringing up that point of the team, because you can’t build something sustainable. I think you can build something big if you hit the right thing at the right time with just a random hodgepodge of people, and you get lucky, whatever, right? But that’s not what we’re trying to do. We’re trying to build a business that actually lasts and sustains itself. And so I think you do have to have those different perspectives and approaches to things.

Jessmyn: And sustainability is kind of one of the biggest things I think we talk about in our annual sort of vision reviews of the company. How sustainable are we? How much… I guess what’s that number called where how many months can we go if for whatever reason we were making no money off of what we were doing?

Josh: Oh, yeah.

Jessmyn: How many months can we go? How sustainable is that? How is the team doing? It’s always kind of checking back in with your bandwidth. Is this too much? What projects can you take on? And if you can’t, when can we push this to? And I think that’s a big sort of deal for me at least, because I see how sort of these bigger corporate companies work, and it’s always, “No, we need results now. This needs to happen yesterday. You need to figure it out now,” but where is the sustainability in that?

Josh: Yeah and I mean, the point about shuffling, I don’t know, if it’s priorities, or projects, or whatever, shuffling those around so that you don’t overwhelm yourself and max out, right? So they have this thing where companies don’t fail because people don’t have ideas or whatever. They fail because they run out of energy, and one of the early episodes I did was with this guy, Paul Fishman, and he had switched to be a self-love coach, because he was a trainer before that, and he was like, “I burned out so hard. I had adrenal fatigue,” and I’ve never heard anybody say what that was before.

Jessmyn: Wow. Yeah.

Josh: He’s like, “Your body is drained of all of its stores of energy, so much so that you’re just basically incapacitated for six months,” because he was teaching multiple workout classes a day and doing the workouts. So he’s working out four hours a day.

Jessmyn: Oh my god.

Josh: Of course, you can’t sustain that, and I think you can totally have adrenal fatigue mentally too. And another talk that comes to mind is the guy who… Well, I won’t name the company, because maybe they’ll try to sue us or something, but this company that you would know the name of went on stage, and he was like, “We pride…” Wait, you might have been there. Like, “We pride ourselves on people joining our company, and then burning out after three months, because they love the job that they work so hard.” And I’m like, “No, I don’t think you should be proud of that. That just means you’re using people up like a sponge and then discarding them.”
And I think that solving really big complex problems too, right? Any of the stuff that you’re working on with building up content streams, oh my gosh, that takes forever, and there’s no shortcuts. It’s like Seth Godin’s thing of I’ll be a guest on anybody’s podcast who’s done a hundred episodes, and maybe now he would change it after the pandemic, because I feel like everybody did a 100 episodes between the pandemic, but it just takes a really long time. And so I think I don’t know if that’s encapsulated in one of these eight points, but I think the idea.

Jessmyn: Yeah, I was going to bring up I feel like we’re sort of leaning into be the best in the world at one thing. I guess it’s a little bit of that and a little bit of being persistent, because you just have to keep going.

Josh: Yeah, yeah. I was listening to Nathan Barry from ConvertKit, another bootstrap company in our space, and he was talking about building one thing for a really long time, and it’s the way to become an expert at that thing is stay focused on one thing for a long time, but it’s like it’s way harder than you would think it is, because it can be boring at times. It can be monotonous. It can be really not fun. You can just run into all these roadblocks, and you’re just like, “I just want to do something else,” and there’s lots of things that go into building that sustainability, and I think that’s part of something our team does really well actually.
Everybody on our team is quite very invested in their lives outside of work. You would stick out a sore thumb if you were at Interact and you just wanted work to be your entire life, because everyone else would be talking about their trips, and their side projects, and their travels, and their friends, and families, and stuff. And you would just be like, “Well, I want to work more.” And it’s like, “That’s not our…”

Jessmyn: Please, don’t.

Josh: That’s not our vibe.

Jessmyn: It’s really not. It’s really not, but I guess that’s not really in here, but I was going to say something of having a work-life balance, and it doesn’t even have to be necessarily work-life like take time off work to do X, Y, Z, but finding a balance between what you really enjoy doing and actually making sure that you have productivity at work, you’re doing something that matters, and that actually is driving towards profit and trying to make money.

Josh: Yeah. And I mean, that brings to mind something that Mark, our coach for a lot of us, I mean, it’s Interact’s business coach, he’s always talking about is you only have three or four hyper productive hours in a day, and hyper productive meaning I’m dialed in on whatever I’m working on. So recording a podcast episode, that’s an hour. Sitting down and figuring out a flow for a marketing campaign, that’s an hour, or two, or whatever, right? You only have four of those a day, and so if you’re sitting down and working for 12 hours a day, eight of those hours, you’re just wasting time and not recharging, because in order to expend those four hours of hyper productive time, you have to recharge the rest of the time, and whatever that looks like. And I think it’s super different for each person.
Depending on your style, you might want to spend most of that alone, or you might want to spend it with people. You might want to be outside. You might want to be inside. You might want to read. You might want to play… Whatever it is, you need to invest in that time. I think that’s just as important as investing heavily in your work. Then, of course, if you don’t feel like investing in your work, then that’s where you got to pivot and work on different projects, which is also something we do a lot at Interact. Everybody’s role kind of changes as you’re developing in your career, and maybe you decide, “I don’t want to work on this area anymore.” Cool, let’s find something else that makes more sense, and you can continue to grow in your career as well as helping Interact grow.

Jessmyn: Yeah, I think every year I sort go through I guess a self-audit in a sense of what projects did I really like, what did I not like, and how does that relate to sort of where I see my career going in the long run, and what I see myself doing in the next 20 years?

Josh: Yeah, because, I mean, it’s important, right? And this is where the perspectives are interesting even between you and I, right? Well, and maybe it’s not. Maybe it’s very similar actually, where it’s like where are you trying to go with your career? What are you trying to build long term? So I think that’s actually the through line, right? I think people often separate out founders, and there is the separation, because it’s just a different role, but I think through line between everybody who’s trying to build a career is what are you trying to do overall? And if what you’re doing now is misaligned to what you’re trying to do overall, I think that’s where work starts to feel very cumbersome like I’m just doing this because I have to work. It’s not aligned with my overall values and purpose. When those things are out of sync, I think that’s where it’s really hard to stay motivated, and burnout happens so fast.

Jessmyn: Right. Right. Okay. So you mentioned Mark, and that is one of our eight is mentors matter. Can you go a little bit more into that?

Josh: Yeah, I mean who you listen to makes such a difference, right? And I mean, the amount of wasted time, and money and effort, that we’ve put in to strategies that have not served us and been out of alignment with how the business grows, it’s crazy. I mean, we stack it up, it’s probably billions of dollars and thousands of hours that people have spent trying strategies that just weren’t in alignment with what we want to do, and how we want to grow, and who we want to be as a company. Yeah, I’m thinking about examples of I mentioned the outbound sales stuff. That’s just not in alignment with how the company operates. We’ve also tried some other stuff with viral marketing things that have just backfired in a big way and cost a ton of money and a lot of technical resources.
And so without placing any judgment on good or bad, because it’s not helpful in my opinion, it’s really just who are you going to listen to? Who are you going to let influence you? And that’s where Mark has been a great influence as a business coach and leader in his own right to the company, and has a lot of experience, and works with other founders and other companies that he can pull in. Other coaches that I’ve worked with and mentors, I think in the article I mentioned looking at Geraldine DeRuiter. She’s a writer and basically her story being, she didn’t really get much traffic to her content for seven years, but she just kept writing, because she liked the writing, and the writing was tied to traveling, and she liked traveling, so she kept doing it, and then eventually Google starts to notice, and they’re like, “Oh this is good content.” It spikes up. Two years later, she writes a book, and it’s a best seller.
So I think it’s about that, which stories are you going to listen to, because you could also look at the other stories and be like, “This person built a company and sold it for $100 million after two years,” and it’s just really which ones are you going to let influence you, because whatever you’re looking for, you can find it.

Jessmyn: Right. I actually in the same season, there’s another episode with one of our guests where she mentioned having a business coach, and she’s a coach herself, which I just loved because it’s no one is perfect, right? There’s stuff that you’re going to miss. There’s stuff that you need advice on, and like I mentioned earlier, you need of a support system in order to kind of keep going and do things that you’re unsure of, or how do I problem solve this? And ever since I started working with Mark myself, I feel like within the… I think it’s almost been two years now, which is crazy. It hasn’t felt that way, but in the two years that I’ve worked with him, I’ve just grown significantly in my confidence and even with how I work with the rest of the team. I think before working with him I was deadly scared of telling you or Annie that I did not… Annie is our COO by the way.
Telling you or Annie I didn’t want to work on a project, or I didn’t feel right about something, and through working with him, I was able to communicate that properly where it was sustainable and also in a healthy way for us to actually collaborate with each other. And ever since then I was like, “Wow, this is actually really awesome having sort of feedback,” but also it encouraged me to start looking kind of elsewhere at what kind of people do I follow on social media, and I want to start my own podcast. Who do I want to sort of not necessarily mimic but gain inspiration from in terms of how I want to do it when I finally get started? And, of course, there’s no perfect way. You’re going to realize you don’t like people as much as you thought you did, but even figuring out, okay, what are not my values, and what do I not align with is going to help you figure out what your business and branding is going to look like.

Josh: Yeah and I think the way that I’ve thought about it with having a coach like Mark is it gives us a common language to speak when we’re working through stuff, right? When we’re trying to figure out a problem, we can use common language to be like, “This is what’s going on, or this is how I’m feeling about this,” or just being able to express how you actually feel about something, and then also know that it’s a psychologically safe space, right? And that has now been taken and used by companies, and now it means nothing, but it’s supposed to mean that you can say what’s going on without worrying about the ramifications of it to your job and your career, like you’re not going to be dinged because you’re like, “I don’t feel right about this project. I don’t feel right about what we’re doing here. Why are we doing this?”
And I think the thing that I don’t quite understand from companies that don’t do that is it’s really detrimental to your growth, right? I don’t know if this story is in there, but one of the longest standing stories that I really remember is from Toyota, and they reward employees heavily if they solve problems. And so somebody figured out that during lunch times everybody goes into the break rooms in the factories where they build the cars, and so they can turn off the lights in the rest of the factory. Turning off the lights in the rest of the factory during lunchtime saved them $5 million a year. And so they gave this person a new car, and a massive bonus, and a promotion, and it was a story exemplifying if you reward people for saying something, then you’re going to go so much further. And I think it’s very shortsighted when companies don’t have an environment where people can say something, and I miss stuff all the time.
Everybody misses stuff all the time. Just because you started a company or you’re a high up at a company doesn’t mean you’re going to stop missing things. And, of course, you have to have tools for working through things if there’s different perspectives, but there’s so many things that you don’t have to mess up, because everybody can say something and be like, “Yeah, I don’t think this is a good idea,” or we’re like, “I don’t have capacity for this, and if I try to take it on, then nothing I do is going to be great. So let’s talk about it.”

Jessmyn: Right. And I think even alternatively, if you have that safe space, say you… For those who are listening, if you’re hiring maybe a VA, or you have someone working under you, or you hire another contractor to help you with something in your business, being able to open up communication of, “What do you think I’m doing wrong,” but also, “Hey, I actually need help with this,,” or “Where do you think I need more assistance,” et cetera, et cetera.

Josh: Yeah. And on the flip side too, being able to say when you do feel really strongly about something. That’s another big one, right? To be able to say, “I have this idea. I’m like nine out of 10 sure it’s the right idea. Unless you feel really strongly that we shouldn’t try it, let’s try it. And then you put in place structures of testing, right? And there’s a great blog post, I forget who it’s by, but they’re basically talking about a marketing experiment structure. So everything is fine. You just throw it on this list. You see if it works, and if it doesn’t work, then you scratch it off the list, and I think that also is more enabled when you’re able to just talk about things, and you can have a tool like that to use when there’s not full agreeance on we should try this or we should try that. It’s just like, “Well, let’s try it and see what happens.”

Jessmyn: I think one of the biggest things for me was having someone to process projects, emails, conversations, things that I’ve read or learned, having someone to process all of that with, and it wasn’t just sort of me on a whim kind of throwing stuff at the wall and seeing what sticks. It was, “Okay, now I have a coach who, hey, I’ve come across this situation.” It doesn’t even always have to be a problem. A lot of the times it’s like, “Ah, something really great happened,” and we process that even of how did it feel, what was that like, how can you recreate that, and even seeing the progress of how that worked, and how you got there has always been super helpful for me in the last couple years, because then I start remembering, “Oh, last time something like this happened I had a really great feeling,” or, “Last time this happened I had a really crappy feeling. How do I work through that?”

Josh: Yeah. And then you can almost… I don’t know if hack is the right word, but you can stack the positive things, and I think that’s the biggest trick of your own personhood, right? You don’t always have to, and this was an interview with the guy that started Compass on how I built this, and he was like, “The best advice I ever got was to stop trying to fix the things I’m not good at, and just focus on the things I am good at.” And I think there’s a huge push of, “You should fix everything that’s a problem, and you should not be triggered by your things, and you should not…” And, yes, it’s important to have tools to work through when hard things happen, when something out of your control comes up, but I think it can almost put you in this state where you’re purposely putting yourself in situations where you’re struggling, because you’re supposed to somehow overcome that or whatever.
I just think that’s so dumb, and just stack up the things that you’re great at, and what’s going to end up happening, especially if you’re starting a company for a lot of our audience, you’re going to end up being so successful that now you can just bring people in to do the things that you’re not great at. And that ties back to the other point about team, which is the things you’re not great at are the things that someone else is great at. And those are the things that are going to make them feel really energized. So you’re serving everybody best by focusing on the things that really energize you and you’re great at, and of course, going back to the bootstrap thing, we all have to do stuff in our roles that we don’t love, and that’s just part of the gig, but if you can stack up as many things that you do love, then you’re going to be much more energized to get through the stuff that you don’t really like.

Jessmyn: I agree. This did lead to a question that I had, which I don’t think we mentioned which point the teams thing covered, which was working with the right people is the only way to scale. And my question for you is how do you know you’re working with the right people?

Josh: That’s a good question. I think the biggest thing is a quote from Paul Graham, which is when he’s investing startups, he pretty much just looks for something that’s very intangible of how easy is it to talk to the founders? And if it’s difficult, then it’s really hard to quantify what that means, but there’s a negative correlation to success if it’s difficult to communicate with the founders. And again, I think this is where I find it very important to not pass judgment and be like, “Oh, there’s a right way to communicate and a wrong way to communicate. This gets into some interesting waters, but again, Jim Collins, the Good, Great book, his thing is basically the way that companies become valuable is to have values that everybody agrees on, and then he’s like, “It doesn’t matter what the values are,” because Marlborough had values that were smoking is good for you, and smoking makes you all these good things, and everyone believed that, and it helped them grow.
Now, I don’t agree with that. I don’t buy into you convincing people that something that hurts your body is good for you, but they did, and that was the rallying point of the company, and so I think for us, that’s why we have really set values, and we reference them all the time, but if you do know what those values are, and you align on them, then it’s really easy to just jump into a conversation with somebody. If that person doesn’t align, then it’s really obvious really fast, and you’re like, “This isn’t going to work.”

Jessmyn: Right. Something that I want to bring up in this topic is sort of figuring out when you don’t feel like you align, at what point do you just sort of let it go? And I think this happened to me a lot when I first started kind of getting into podcasts or getting into working with people where I had to kind of have a conversation like this, or work with people, or even Jessie on my team. For those of you who know her, shout out. When she edits this she’s going to be like, “Oh my god, it’s me.” But I think there was this… For me, it’s kind of weird. I guess I’m a little more intuitive about it, because I’m an empath, so I feel a lot of the feelings that people project even through their body language, right?
And so when it would happen to me where I’m like, “For some reason I just don’t…” Not even that we don’t get along. I just don’t feel like we’re on the same sort of energy levels, and for me that’s where I’m like, “Okay, I need to think about if I want to move forward with this. What does that look like? What does it not look like, and how do I work through that?” Which is also where having a coach comes in, because then you can process all of those feelings. But I guess a great example would be in Jessie’s case, not to throw her under the bus, but it’s not really throwing her under the bus.
But we had worked together sort of on a part-time basis for six months before we hired her on full-time, and I was a little hesitant because of previous experiences where I was like, “I just don’t know. I’m second guessing everything that I’m thinking. I’m second guessing everything that I’m feeling.” And not to say that it would take me six months now to figure it out, but give yourself sort of time to figure out what are the cues that I’m looking for of do we align on the same values without getting on a call and asking them, “How do you feel about X, Y, Z,” and interviewing them on if it works or doesn’t work.

Josh: Yeah, and I think that’s really interesting perspective, because from my view, the thing that I think Jesse brings to our team that is super valuable is the patience and persistence, right? She runs the Instagram channel. It’s a slow grind. You have to be super consistent, and it’s just a very slow process, and we crossed 1,000 followers this year thanks to her consistency there, but it takes a certain type of personality to be able to keep going when it’s just really slow like that. So it’s interesting your perspective of what you were looking for, you’re actually looking for what it is that she brings to the table, which is like, “It’s actually okay if you need more time to figure this out. I’m just going to keep moving forward.” And then that’s perfect for the role, because that’s what the role needs.

Jessmyn: That’s a good point. That’s good point.

Josh: And I think it’s interesting how that stuff works out sometimes, where it’s just not necessarily intentional, but it’s like this actually worked out because I was wanting to look for a certain type of person, even though I may not be able to articulate that’s exactly what I’m looking for, and then this person filled that need in a certain way where it’s just a great fit, and then it’s been awesome. And having her run that stuff is super important, because it does matter, but it’s also just like it’s a grind.

Jessmyn: Right. Right. And I think also something that I learned in the last couple of years was sort of learning when… Not really learning when to say it’s not a right fit or it’s not a good fit, but feeling okay with saying it’s not a good fit, and it’s still something I think that I am learning, because I try to make everything fit as much as possible. I’ve learned that I am one of those that’s like, “I can fix it. I can do it. I can do it.”

Josh: Yeah, and I think-“

Jessmyn: And if you guys are Listening, you should have seen Josh’s face right now.

Josh: It’s interesting because we have a blog post coming out about what makes meaningful work, and most folks on our team contributed to it. And the biggest one is helping people across everybody on our team. And I think that the potential pitfall of that is that you’d want to help everybody, and you want to make every situation work, and I’ve been learning a lot from Brene Brown about this, because she’s a natural helper fixer too, but she’s just gotten so bold with it now to where she is like, “I can go,” and she told this story about getting a massage, and she’s like, “They ask you if you want more pressure or less pressure, and you don’t want to offend the person and be like, “Oh, you need to work harder,” or it’s, “You’re not doing a good job.” And she’s like, “No, actually now I just say, “More pressure please, and I don’t want to talk.” And I’m like, “Oh gosh.”

Jessmyn: That would give me so much anxiety.

Josh: Right? But then I started practicing it in conversations, and someone says something, especially when somebody assumes you’re going to do something, and I’ve started just responding like, “Actually, no, I’m not going to do that.” And depending on the state of the working relationship, if it’s a new partner, I’ll just be like, “I’m not going to do that. If that means the partnership doesn’t work, then that’s fine,” or if it’s further down the line, and I have trust and rapport with that person, I’ll just say, “Well, actually that doesn’t work for me,” and not say anything else, not give an out, not fix the problem, not be like, “Give an alternative.” Just be like, “No, that one actually I’m not okay with. Can you leave it?”

Jessmyn: That definitely reminds me of sort of just setting your own boundaries and sticking to it.

Josh: Yeah, and that’s, I mean, the fear. I think the underlying fear there is, “Well if I don’t work with this person, then we’re not going to hit our numbers. We’re not going to grow. We’re not going to x, y, z.” And I think that’s where that people over profit one really comes to play, because we’ve passed up, I don’t know, hundreds of opportunities for faster growth, because the way that we would grow or the people that we’d be partnering with just didn’t work for us and our values. And so you end up saying, “No,” to a lot of things, and I think at first it’s really scary, because you’re like, “This could tank the company.” And then you start to do it and you realize, “Well, first of all, there’s a million reasons the company could tank, and there’s nothing you can do about that.” So it’s like you know the guy on Parks and Rec? Have you watched that show?

Jessmyn: I did.

Josh: The guy who eats a lot of meat. He’s the manager. Wow. I don’t know. I can’t remember his name.

Jessmyn: Are you thinking of Ron Swanson?

Josh: Yeah, Ron Swanson. Yeah. But that guy in real life, he tells this story about his sense of humor, and it comes from growing up on a farm, and he’s like, “You develop a really dry sense of humor growing up on a farm, because literally every year a rainstorm could ruin your entire paycheck for the whole year, a rainstorm at the wrong time. So you just get in this mode where you just joke about it. You’re like, ‘Well anything can happen. We can lose our entire wage for this year, and then we’ll just go hungry.’ And then you make a joke out of it, because what else are you supposed to do?” And so I think that’s where I’ve started to get to, especially with things that feel very threatening.
And that’s almost always the case with these relationships or situations, partnerships that don’t work out. It’s like it feels very threatening, but then I’m just like, “Whatever. Nothing is threatening and everything is threatening, and probably if something crazy did happen, it would be the last thing you would expect anyways, and so there’s nothing you can do about it.” And then you just proceed.

Jessmyn: Right. I can think of a million things that we were not expecting and happened, and it was not what we thought. Okay. The one that we didn’t go over yet, which I really wanted to ask, but I think it would be a good sort of rounding off point to the episode is in the beginning you can only serve one type of customer. So tell me what that means.

Josh: Yeah. I mean, so I think when you came on was when we were first really starting to feel this, and it’s ironic, right? And I think this is another point that’s not in here, is the concept of the upward spiral, which is it’s not a downward spiral where things are getting worse and worse. Things are getting better and better, but you keep spiraling around to the same problems over and over again. So I got this advice from the VP of Pandora back when Pandora was a big company, and she told me this before we started Interact. She’s like, “Just do one thing the best,” and I was like, “That’s great advice.” And then, of course, we didn’t actually do that. For the first four years of the company, we tried to work with every type of customer. We built all these custom quizzes. We were working with giant nonprofits, and SaaS companies, and just literally everybody, and that was getting us nowhere. We were spread way too thin, weren’t growing.
So then we decided to go all in on one market, which is the… Well, it’s called the creator economy now, but nobody called it that back then. It was really just marketing coaches, and people who are creating courses for marketing, copywriting, social media, all these types of things, alternative education. So we went all in on that, and that was really where it unlocked the key to growth. And we were talking before the show, we’ve grown 7X in the last five years, so just massive growth by any standard you look at, and that really was because we went all in on one market, and we’re just like, “All right, we’re going to serve this market super well.” And then there’s a million things that come along with that, right?
All of our marketing, all of our onboarding stuff, all of our community stuff, all of our coaching stuff, all of our copywriting, the entire product is built for that one market. And now we’re slowly expanding the edges and moving outward to e-commerce, and some other types of coaching, and online services. Yeah, I don’t think you can really, especially if you’re going to bootstrap, you can’t afford to build a product for a bunch of different industries.

Jessmyn: Right. And I think what comes to mind is if you are trying to sort of hit everyone, how can you really figure out what your brand is if you’re trying to fit every single mold and there’s too many things to try to do at one time? Whereas if you pick that one market, right? That helped us, I mean, it wasn’t until we brought Francine on that we actually organized all of these thoughts, but we started thinking, “Okay, this is the type of customer. This is what they like to do on the weekend. This is what they like to do in their business. These are the type of people they like to work with, and this is the type of values that they would have.” So I think figuring out that one market and going after that one market helped us figure out our branding, and then we were able to sort of expand out from there when the time was right.

Josh: Yeah. And I think this is the appeal of software. Software companies get this reputation where it’s like, “Well, you can now work with the entire world, so you should.” And I think that it’s a disservice to everybody, because you’re going to deliver a subpar product to your customers. It’s not really going to do what they need it to do, You’re not going to be able to help them, and then on the other side, why would you want to work with a company that’s working with everybody, right? And it doesn’t serve your needs, and I think there’ll actually be a very much a breaking down of SaaS in the future where instead of having one company that does let’s say email marketing for everybody, you have 50 companies, and you’ll do an email marketing company that’s for whatever industry you’re in, like if you’re a photographer.
I think companies like Showit have done this really well with the web design space, where they focus on a couple of industries, and that’s the approach we’ve taken with quizzes, because there’s certainly other quiz builders that have more features, or are advanced, and whatever, but they’re built for everybody instead of being built for one audience. And so it’s just going to take you way more time. It’s not really built for you trying to always fenagle things to work, and so I think that’s where things are headed.

Jessmyn: I totally agree with that. I mean, even when thinking of content for our blog, I’m always thinking of, “Okay, fine.” I just came up with this idea yesterday of the perfect toolkit for an e-commerce, a small e-commerce business, or the perfect toolkit for a coach on a budget, something like that. And when I talk to people, there’s certain email marketing systems, for example, that they would use based on what type of industry they are, how many people are in their company, what their budget is. So I could totally see that happening where people are just going to find those specific markets, and that’s what you should go for.

Josh: Yeah, totally. I mean, the same thing. I mean, tool is a good word for it, because if you’re at home doing a DIY project, and you need to cut a board, you might not need a super fancy saw that costs $3,000. Just use a hand saw and a thing to hold it in place, so it’s a straight cut, right? It costs you 10 bucks instead of 3000, and I think we’ve done a really poor job with software, especially because the software that costs 3000 probably has the most money to do marketing. So they’re going to reach all those people and be like, “Hey, buy our saw.” And in reality, you just need the simple one, but the simple one doesn’t have money to do marketing, and so it creates this situation where everybody is buying stuff that they don’t really need, that’s way too expensive, because those companies have the money, and it creates this crazy self-perpetuating cycle, which I don’t know how to fix that problem, but I think that’s kind of where things are at now, and it’s just starting to proliferate and get broken down into more pieces.

Jessmyn: Right. Love that. Love that. So my last question for you based on this article is do you think there is another lesson sit coming in the coming years of having a bootstrap business?

Josh: Totally. Yeah. I mean, I think the one thing that is consistent is that the more you know, the more you don’t know, and that’s another thing from Mark where it’s like if you think about the amount that you know as a circle that expands, and then everything you don’t know is the surface area that your circle is touching. So every time you learn something new, you just learned five more things that you don’t know, and so I think as much as this article is a bit of a sign post on the trail, it’s just that it’s like it’s at mile two, and there’s another 100. So there’ll be lots more sign posts where we learn other things and realize all the things that we thought we were so certain of, that turned out to not really work out that great, and we’ll write about it when that happens.

Jessmyn: Love it. Look out for that new article, 25 lessons. I’m just kidding.

Josh: 400 lessons.

Jessmyn: A million lessons of having a Bootstrap business. I don’t know. That might work really well.

Josh: Yeah, perfect.

Jessmyn: Well, Josh, thanks for hopping on, and I think next time we are going to go over another article that you wrote, so this one will be linked in the show notes, and we’ll see you guys then.

Josh: Cool. Thanks for having me on. This was fun.

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Jessmyn Solana

Jessmyn Solana is the Partner Program Manager of Interact, a place for creating beautiful and engaging quizzes that generate email leads. Outside of Interact Jessmyn loves binge watching thriller and sci-fi shows, cuddling with her fluffy dog, and traveling to places she's never been before.