Fears and Anxieties of Running a Business

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In this episode of Building Infinite Red, Jamon, Ken, and Todd touch on the fears, anxieties, and struggles of running a business. They share stories and thoughts on starting a business, managing stress, how success and failure impact focus, the difference between venture capital and other sources of funding, fear of missing out, and the importance of knowing what you stand for.

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TODD WERTH: So I thought a good topic today, one of the reasons because I’m personally interested actually, hear what Jamon has to say and Ken has to say, and of course I’m sure they’re interested to hear what I have to say. But the topic is when you start a new business or you’re an entrepreneur doing multiple businesses, or anything of that particular area. What are some of the biggest fears, anxieties, apprehensions, that you might have you know before the process, during the process, whenever? I find this very fascinating, because I imagine a lot of people, well maybe some people who are listening are experiencing these right now and A) it’d be great to hear someone else express the same thing so they know that they’re not alone in this, and B) it’s kind of interesting to think about yourself. It kind of, it’s not something you typically sit down and think about, so if you two don’t mind, that’d be a really interesting subject for today.

KEN MILLER: Sounds good.

JAMON HOLMGREN: Yeah. Well I think back to when I started by business. It was 2005, and I was working for a home builder at the time, so I had a, you know, decent job. It was an office job. I was doing I think cad design and marketing for this builder. Not really doing programming. But I decided that one of the things that … well I had, prior to this time, I had thought, you know I’d be really nice to own my own business at some point. It’d be something that I would aspire to. And I think that part of that was my dad owning his own business and knowing a lot of entrepreneurs kind of played into that. I thought it would be an interesting thing. I’ve always been a little bit independent. Want to kind of set my own course.

So I started thinking about doing this and talking with my wife, and at the time I had a six month old baby. That was my first kid, my son, who is now 13 years old. Around actually this time of year is when I decided that I was going to do this. What helped was an opportunity that came up. So the apprehension of how do I get my first customer was sort of already taken care of. My uncle had a bunch of work that he needed done, and he asked me if I wanted to do it kind of on the side, or as a business, and that gave me the confidence to pull the trigger and say, let’s so this. Because I had a built-in customer right away. But I do remember the first month sending my bill over to him, and it was only eleven hundred dollars, and that was all I had earned that whole month was eleven hundred dollars. And that was a wake up call to me that, hey I can’t just expect the money to come in, and that was definitely … I sat up and noticed.

TODD: Yeah, that’s really interesting. So when you started ClearSight, that was your first company, correct? At that time?

JAMON: That’s right. Yeah, ClearSight. There were other points along the way where I was sort of I got kind of gut-punched. Many times along the way. One was when … my first business was doing websites, but it was also doing CAD designs, so I had essentially two business, and the CAD design part of it, you know designing homes, designing remodels, those sort of things eventually dried up, because remember that was during 2008, 2009 the housing recession kind of came along and that impacted the designers first, because we were the first ones in the process. People stopped taking money, equity out of their homes to do remodels. They just stopped doing it. So basically the whole market dried up.

I remember my uncle told me, “I don’t have any work to send you anymore.” And I had a few accounts myself, but they were pretty slow too. And I kind of sat at home for a few days and felt sorry for myself. But in typical Jamon fashion, I was like, well I guess it’s time to go do this myself, so I went out and literally started knocking on doors at offices and stuff and handing out my business card. Wasn’t too successful at that, but it was at least doing something, and then things turned around eventually.

TODD: Since you had a new baby at home, and obviously you’re married, and you’re trying to support them.

JAMON: Right.

TODD: Did that add any worry to you at that time?

JAMON: Yeah, for sure. It certainly did, because any worry that my wife felt was reflected back on me because I feel very a sense of responsibility that I need to be making sure that we’re not losing our house. Making sure that we can keep food on the table, things like that. So that was a lot to process. My health definitely suffered because of it and a few other things, but there was a lot of stress involved with that. I think that if I were to go back now, knowing what I know now, I could very much have probably pulled out of it much faster. I could have found a better path, but you live and learn.

TODD: I’m sure there’s more to tell about that story, but I’m curious to hear your thoughts Ken.

KEN: For me the biggest worry was always money. Right? I mean, since I came out here to Silicon Valley, I had the dream. I had the Silicon Valley dream for sure. I wanted to start my own company. And to a certain degree, the Silicon Valley dream as sold is not sold accurately. Right? It’s sold as this sort of fantasy. And the truth of the matter is you have to have more resources than is reputed in order to do the Silicon Valley way effectively. You need to know VCs or people who know them. It helps to have affluent parents who can bankroll you not making any money for years and years and years. I’m luckier than most on all of those accounts, and even I found that very intimidating, challenging. And especially living in the Bay Area, once you have established a life in the Bay Area, the idea of not taking a salary for a couple of years is utterly terrifying if you don’t have a big pile of money.

In fact, I wasn’t really able to do this until I had a little bit of a windfall from the Yammer acquisition to lean on. Basically just enough to let me barely scrape by for a year for which I’m still very grateful ‘cause I probably wouldn’t be here today if I hadn’t had that. And there were some scary fricking moments. There’ve definitely been a few extremely close calls financially. So I don’t … that fear I think was justified and surmountable. Let me put it that way. Right? You can definitely figure that one out, but I’m not gonna lie. It can be super scary sometimes.

For me, the biggest mental shift that got me where I am now is that I had always had in my head this sort of venture capital model, because that’s what I knew. Right? Because that’s the kind of company I’d worked for. I saw how that process basically worked. But it always felt wrong to me. Right? Like, I was always like, what’s so wrong with profit? What’s so wrong with actually making a business that can support itself fairly early on? And I think it was the Paul Graham post that was like, the difference between a start up and a small business. And a start up is specifically optimized for hundred S growth or nothing.

JAMON: Right.

KEN: And that’s what venture capitalists want for the most part. Right? No venture capitalist wants you to be one of the nine or ninety-nine that don’t make it.

JAMON: Mm-hmm (affirmative)-

KEN: Nevertheless, the model is set up that way. The model is set up so that only one in ten or less have to make it. And so once I realized, oh no all along I wanted to make the lifestyle business, basically, the small business.

TODD: I just wanted to point out that especially in Silicon Valley the term lifestyle business is a semi-derogatory term.

KEN: Pejorative, yeah.

TODD: Yeah to refer to a normal, actual business.

KEN: Exactly.

TODD: And I always found that amusing when they said lifestyle business it was insulting you, because you make a profit. I always thought that was funny.

KEN: Yeah, right. It’s sort of like the Silicon Valley model is for people who would rather be a billionaire or nothing. Right? It’s kinda like a shot at a billionaire is worth way more to them then a pretty good path to a millionaire. Once I realized that that was the exact opposite of me, I was much happier and I could actually work towards something that mattered. Right? And not even the millionaire part, right? It’s like, if that happens, that would be awesome, but it’s more creating the environment that I wished that I’d had.

JAMON: When it comes to fears and those types of feelings, do you ever feel maybe that you are missing out on those wild rides?

KEN: Do I have FOMO for the-

JAMON: Yeah, a little bit of FOMO.

KEN: Sometimes.

JAMON: FOMO being, of course, fear of missing out.

KEN: Yeah, living here especially. I think that’s inevitable.

JAMON: Right. Because we’re not set up for just rocket growth at Infinite Red.

KEN: I’ve been at enough companies that ended up making everybody thousandaires or worse. Right? Or negative thousandaires in at least one case. I had a friend, he seemed like he was living the dream. This was way back when in the first boom. Right? He seemed like he’d lived the dream. Right? He was just an engineer at a start up and he was suddenly a millionaire overnight. And then within six month, he was a negative six hundred thousandaire with a gigantic tax bill.

JAMON: Oof.

KEN: The whole model has kind of lured a bunch of people into the stock option thing. This is what I’m talking about specifically. I think there is absolutely a place for the venture capital model, but the stock option compensation model that a lot of people have done, is kind of a raw deal in a lot of ways, but that’d be a whole other topic, so-

JAMON: Yes

TODD: Just real quick, I own tons of stock and stock options that are worth absolutely zero-

KEN: Yes.

TODD: But, if I ever run out of toilet paper, I am set.

JAMON: So Todd, you started a business well before Ken or I, and you know I actually I don’t know if I’ve ever heard the story of your very first business and how you went from being a software engineer at a company to owning your own business, and I’d like to hear about that from the perspective of the topic of this episode which is about fears, and uncertainty and things like that.

TODD: Yeah. Yeah. That’s great question, so I’ve owned three businesses. This hopefully is my last one here at Infinite Red. My first one was in 1999. We started, it was three of us, it was also a consulting company like Infinite Red which lasted for nine years. It was a little bit different. Real quick, we did mainly enterprise, not start ups, larger companies, that kind of stuff. And our model was kind of to be subcontractors. So we had a lot of relationships with other consulting companies.

One of the things we did, is we did really hard things well. So all the other consulting companies, like especially at that time it’s gonna sound funny, but you’d have companies coming to us saying, “Look, we’re doing most of the project, but they want something on the web, and we have no idea how to do that.” And we did. And we knew Visual C++ and we knew all sorts of things. And so we specialize. We were higher priced because of that, and we’d come in and do the fun parts, in our opinion, which was really great. This is circa 1999. That one wasn’t … there wasn’t too much anxiety from it. It was a small company, so later I’ll talk about most of my anxiety at Infinite Red come from my worry of the 25 families I’m responsible for.

JAMON: Right.

TODD: It’s not so much myself, because I do not have affluent parents. Well, most of my relatives are dead now, but I never really worried about money. I mean worst case scenario, I can be a developer. I’m pretty darn good developer, and I can make good money at that. And I moved out of the Bay Area, so for me my lifestyle is much cheaper than it used to be. So I don’t worry about that so much, but I do worry about everyone’s families who work at Infinite Red.

My first company, we didn’t have that. It was all just high level people. There was three to six of us, depending on the time. And we kind of just slipped into it. We had our first few big customers before we even started. So that wasn’t really stressful at all.

The second company, which came after my first company, I went back and worked for companies, for other start ups as an employee, and that’s how I met Ken. Ken was my boss. And I was doing that mainly just ‘cause after nine years running your company, I was just kind of tired, and I wanted to be an employee for a while. And I did that for about three, three and half years. And Ken, sorry boss, it was super relaxing, easy. You work like seven and a half hours a day or whatever.

KEN: This has been noted on your permanent file.

TODD: You know, regular jobs often are pretty lax compared to start ups. As an aside, I was in a pizza parlor once, and I saw a sign behind the wall. It was obviously the pizza parlor was owned by a person, it wasn’t a chain, and the sign said, the only thing more overrated then running your own business is pregnancy. Which is true, if you do it for low hours and high pay, you really should rethink that, but there are lots of great reasons to do it.

Any who, my second company was venture capital backed company which means we didn’t use our own money. It was intentionally designed to do the hockey stick which means go from zero to very high very fast, and we had investors. And we had to pitch to venture capitalists and angel investors, and we had all the kind of normal Silicon Valley stuff. And that lasted for about a year and a half, and I cherish that experience, because it taught me a lot about that process from the inside. It was completely a failure which is fine. The fears in that, once again, were not personal, because as I did right after that, I went and got a job with Ken.

JAMON: Right.

TODD: And I made plenty of personal money. And because we weren’t investing our money, the VCs were, there really wasn’t a lot of anxiety there. I would say the main anxiety there was performance. Meaning it’s kind of depressing when you’re failing, and sometimes you have a great success. We did one month, especially. And we were shooting to the moon for a whole month, and it was super exciting. So it was just kind of a roller coaster of anxiety for that kind of business. Yeah, Jamon?

JAMON: I think it’s really interesting to hear you and Ken talk about the idea of, well I can just go get a job as a developer. Because for the longest time, I didn’t feel that I had that option. Whether that was reality or not, I don’t know. I was basically, I kind of thought of myself as just building websites. I just built websites for people, and I didn’t really think of myself as a software engineer. I just happen to be someone that happened to built websites.

TODD: Knowing you Jamon, and the quality of engineer you are, you are completely wrong. You could have totally got a job, but I get why-

JAMON: Yeah.

TODD: -from your perspective you felt that way.

KEN: Yeah, well and it’s a matter of … it highlights how important just knowing the scene is.

JAMON: Right. Yeah, totally.

KEN: If you know the scene, yeah if you’re an engineer, even like an old rusty engineer, like we’re going to be before too long.

TODD: Too late, Ken.

KEN: Right.

JAMON: Too soon and too late.

KEN: Even if you’re an old rusty engineer, you can figure it out. Right?

JAMON: Right, yeah.

KEN: The demand is so overwhelming and so consistent and so pervasive that-

JAMON: Yeah.

KEN: -if you know sort of the ins and outs-

TODD: Even you Jamon could get a job is what you’re saying.

JAMON: Even I could get a job.

KEN: No, if you’re half-way competent, and he’s more than half-way competent, about 60 percent.

JAMON: I appreciate it.

KEN: No, it’s-

JAMON: 60 percent. Yeah. No, and to hear that now. It’s something that is obviously more of an option now that I don’t need it, but at the time it didn’t feel like an option, and so especially when I started getting employees in 2009. And most of them were young. They didn’t have much in the way of family, but they would obviously still have … they needed jobs, and I felt that. I felt that in every part of me that if the business wasn’t doing well, that I was failing them. And that actually drove me for a long time. I think if I’d had the option to go work for someone, or felt I had the option to go work for someone, I may have actually quit at some point. But I didn’t. I kept the course there.

KEN: I will say, that I’m glad that I did not know everything that I should be afraid of going into it. ‘Cause there is plenty that you should be afraid of, and if I’d known all that stuff going in, I probably wouldn’t have done it, and I’m glad that I did it. And if I had to redo it now, I would do it again.

JAMON: Right.

KEN: And that’s an important distinction is that it’s not that I would do it again, it’s that only hearing the bad stuff at that point, would have been a disaster.

TODD: Ignorance and hubris are the two best tools of the entrepreneur.

JAMON: I feel like it’s both more stressful and more scary than you think, but also you’re more resourceful and more able to deal with it then you think.

KEN: Yes.

TODD: Hundred percent. I would say, talking to other people who are new to it, and I certainly had to learn this, the biggest problem is the buck stops here. Meaning in every other situation where you worked, you could always throw a problem up the ladder.

JAMON: Yes.

TODD: And when you’re a small business person, you don’t know accounting? Doesn’t matter. Do it.

JAMON: Someone’s gotta do the accounting.

TODD: Right, like there’s literally no excuse. There’s none, and you don’t have that money just to pay for people to do it.

KEN: I guarantee the IRS does not grade on a curve.

TODD: No, they don’t care about your excuses.

KEN: Yeah.

TODD: So Jamon, Ken, and I come from very different places. So Ken obviously went to Harvard. He’s impressive on paper. I actually did not. I didn’t finish college. I started making way too much money as a programmer to be honest. But when I first started out in 1996 as a professional programmer, you know I wasn’t making tons of money, but it was plenty for me, because where I’m from, it’s a lot of money. And at that time, I’d probably be more like Jamon meaning I didn’t see myself as really deserving that kind of stuff, but this was in San Francisco in 1996. So I saw the first boom, and then I saw the crash, and then I saw the second boom. And after a while, you start to learn, although I don’t have Ken’s personal background. I do have Ken’s professional background.

JAMON: Mm-hmm (affirmative)- Yep.

TODD: And so, one of the things I’ve noticed when talking to Jamon, because he’s in Vancouver, Washington, and not around that stuff as much, is he feels a little bit like an imposter. He’s totally not. And I bet even now in his mind he imagines that those people working at Google somehow have this huge, amazing, genius to them, and Ken’s probably in the middle. He probably thinks some of them do. I personally have yet to meet one of these fabled geniuses. So the more you get involved with that, the more you realize they’re just humans, and you’re just as good as they are.

KEN: That is true.

JAMON: I think that’s been something that I’ve become more and more aware of over the past several years. And it’s funny because I don’t usually think of myself as having imposter syndrome. I’m actually quite a confident guy, but in that regard I definitely did not really realize … it felt like they were a different breed. They were a different type of person. And I always felt like I could probably learn anything, but there was still this degree of separation. But, anyway, coming back to the topic at hand, I think that sort of uncertainty and fear can be a motivating factor. But one of the things, so one of the things I’d like to talk about, is there are healthy ways and unhealthy ways to handle that stress, and I’ve done them all. Believe me.

TODD: Like cocaine?

JAMON: Maybe.

TODD: Jamon’s mother, he’s totally joking. He’s never done cocaine.

JAMON: Yes, thank you Todd. And my mom does listen to this, so thanks Todd.

TODD: He really has not, trust me.

JAMON: You wouldn’t want to see me on cocaine.

KEN: Oh god. Yeah, that is the wrong drug for you my friend.

JAMON: Yes.

KEN: Oof.

JAMON: But you don’t want to transfer stress to clients. You don’t want to transfer stress to employees. You don’t want to transfer it to your significant other. To your family. And unfortunately, I’ve done all of those things, because I’m human and that’s what happens. You get a lot of stress, and then you feel like you need to let off steam. One of the things that I actually really appreciated about this partnership is that we’re able to let off steam with each other. And in a way, that is healthy. That isn’t transferring to someone else who has nothing to do with it or has no power. Where I have two partners who are actually in the same spot, and they can help. It’s been really, really helpful. So that is really important. I think how you transfer stress. Yeah, Todd?

TODD: I agree. I don’t kick the dog. I kick Ken. Which is better. The dog appreciates it at least.

JAMON: You don’t even have a dog, Todd.

TODD: I don’t have a dog, and I’ve never kick a dog by the way. I’d kick humans all day long, but never a dog.

JAMON: This is true.

TODD: Just to be clear.

JAMON: Yes, Todd is the one who canceled a meeting because he had to bring a bird to the hospital that had hit his door, actually one time.

TODD: It’s true. It is true, and that bird is flapping happily today.

KEN: As far as you know.

TODD: I hope. Back to my story, because it’s all about me. Anxiety at Infinite Red really does come around to team members mostly, and you two Ken and Jamon because I don’t want to let you down, and I certainly don’t want someone’s family not to be able to have a Christmas because of something stupid I did, or because I was acting emotionally when I should have been acting rationally. That kind of stuff.

JAMON: This year, me not having Christmas had nothing to do with you Todd, so I can let you know that.

TODD: Jamon’s house was burglarized and burnt down. Not burnt down, but set afire on Christmas Eve.

KEN: Torched.

TODD: So, if you’re feeling good about humanity up to this point, now you can feel bad about it. So, there you go, but they’re back in their house.

KEN: You’re welcome.

TODD: Everything’s good.

JAMON: Yes.

TODD: You’re back in your house. Everything’s good, and he has a wonderful family, and all is well.

JAMON: Yeah, it’s really nice to be back. Anyway, I cut you off.

TODD: But so that’s a lot of my anxieties about it. At my age, I’m 46, and I’ve done this a long time. I don’t stress as often. Like I used to get very stressed out doing sales calls or that kind of stuff. I’ve done all that stuff enough where it doesn’t really bother me too much. Even tough things where you have to be really tough with the client, or vendor, or something like that. It doesn’t, I mean it bothers me temporarily of course you get the adrenaline going and no one likes that. But it’s really the things that give me anxiety and up at night is if I make a mistake that will cause us not to be able to pay payroll.

JAMON: Yeah.

TODD: Now, one note. We’ve always paid payroll.

JAMON: Yeah.

TODD: But that is something-

KEN: There’s been some close calls.

TODD: That is something that-

KEN: Yeah.

TODD: That makes me work harder, and it makes me worry. Me, personally, I could figure it out, it’s not as big of a deal to me.

KEN: Well, I think also a big stressor that I didn’t … it makes sense in retrospect, but it wasn’t one that like occurred to me, is how hard it is to maintain focus over time-

JAMON: Mm-hmm (affirmative)

TODD: Yeah.

KEN: -when you don’t have a boss doing that for you. I was a small scale boss at my previous jobs, but this experience definitely makes me want to write a nice little note of apology to every boss I’ve ever had. Like, however bad they were, I have more sort of sympathy for what they were dealing with then I did before.

TODD: That’s so true.

KEN: Yeah, and the surprising thing is how hard it is to cope with success. When you’re doing well, that’s when the monster of de-focusing really starts to rear its head. It’s like driving a car fast. If you’ve never driven a car at 150 miles an hour, it’s a different thing from driving it at 60 miles an hour. It takes a little getting used to that state, oh things are going well, but that doesn’t mean that I get to take my eyes off the road.

TODD: Mm-hmm (affirmative)-

KEN: So.

CHRIS MARTIN: Can you guys go in a little deeper on how you manage some of these things? ‘Cause you’ve talked about having the feelings of stress and fear, but maybe some of the ways that you manage it, a part from kicking Ken.

KEN: That’s Todd’s favorite.

TODD: Well, Ken mentioned that success can be hard to deal with, and I have a tried and true technique I’ve used for many years with dealing with the problems of success. And here it is. And I’ll share it with you. I normally would charge for this advice, but I’m gonna share. Don’t be successful. There you go.

KEN: Yeah.

TODD: You’re welcome.

KEN: That one we’re still figuring out. Having co-founders you actually trust is probably the number one.

TODD: Yeah, it’s hard to do, and at one time in my career I said I would never ever had a partner or a co-founder again. And here we are, so.

JAMON: I think getting together in person is important. Of course, we’re a remote company. So I’m up here near Portland, and Ken’s in the Bay Area, and Todd’s in Vegas, but we did get together a couple weeks ago to talk. And there was a stressful situation going on, and that was something that we went through together in person.

TODD: Well, we also hang out in zoom a lot.

JAMON: Yeah.

TODD: Every week. And that’s similar. But, yeah having good co-founders who are your friends, and you become almost married at a point, because when you’re in business together it is like a marriage, and you know everyone’s finances. You know if someone’s spouse is having problems with the way the company’s working. You have to deal with that-

JAMON: Mm-hmm (affirmative)-

TODD: -at least as an auxiliary person in that particular thing. So it’s a very intimate thing for sure. I definitely choose that very, very, very wisely. I’ve had bad experiences, and of course I’ve had great experiences here.

JAMON: I think that one of the things that we actually do fairly well is we will say when we’re stressed. You know, we’ll say, “Hey, I am currently feeling a high degree of stress.” And then the other co-founders can say, “Okay, what is causing this.” And we can talk about it more objectively. And just saying it out loud sometimes is a way to kind of like let go of it a little bit.

TODD: We also know how to fight which takes a while. That’s a hard one to learn.

JAMON: It is.

TODD: But we’ve learned how to fight. Yell at each other, and know that afterwards we’re going to be okay, and that’s important.

JAMON: Yeah.

TODD: The trust that you would gain with a girlfriend or boyfriend or your spouse-

KEN: Sibling

TODD: -where you can have an emotional throw up as it were and know that you’re still gonna be loved as it were.

KEN: Well, and also it’s sort of on the focusing issue, actually. It’s relevant there too which is that I’m pretty ADD I would say. I think that’s probably pretty common I would say for entrepreneurs. Entrepreneurship is one place where you can actually challenge your ADD tendencies. However, I also know it’s like, “Hey guys, I’m having some trouble focusing and motivating on x, y, and z-

JAMON: Right.

KEN: -can I have help with knowing that there’s not going to be any judgment coming along-

JAMON: Right.

KEN: -with that help?”

JAMON: Right. Yeah.

TODD: To be clear, it’s all not roses. Sometimes one of us gets irritated with the other person because of these issues and-

JAMON: Right.

TODD: -but ultimately once we get talking to it, we’re not super human. Sometimes I get irritated with Jamon or Ken and vice versa. But the whole point is, when you get to the end of that, you’re supportive.

JAMON: Another really important thing is to have some really core principles. Some kind of tent poles so-to-speak that you can come back to. One of the things that we really strongly believe is that the core of us three is one of the most important things about this company. And so we can come back to that. I mean, if the most important thing that we had was some technology or some financial goal or something like that, then it would put a lot of stresses on our relationship, but since we’ve made that relationship such a high priority, it’s extremely important. And another thing, along those lines, is we recognize that we are human, and that sometimes it’s actually a personal situation that’s contributing to work stress.

TODD: Yes.

JAMON: You might have situation where maybe a family member has health issues or you’re having trouble with a relationship, or anything along those lines, and we … I was actually talking to an employee recently who talked about a personal situation that they were having and how it was contributing to their stress, and I had noticed the stress that they were going through at work, but I didn’t know about the personal situation, and it’s okay. I told them, “It’s fine. It’s a normal, human thing to have situations that arise. I understand. It’s something that you can tell us, if there’s something going on, you don’t have to be specific. You don’t have to tell us private information, but just tell us that something’s going on, and we will do our best to be as understanding as possible.”

TODD: And it’s a matter of trust. That particular person trusted Jamon. That’s fantastic. It’s trust that we build up between founders. It’s trust with the team, and to some extent, trust with your customers, and your vendors. Especially with customers and vendors, if you can do that, that’s fantastic, but the others you can do with time. Just to give you an example, trust. I try to be trusting even when I shouldn’t be. I picked up this guy the other day, in my car, he gets in the backseat. I just picked him up. I didn’t know him, and first he gets in, understandably he’s like, “Thanks for picking me up, but how do you know I’m not a serial killer?”

TODD: And I just looked at him. I’m like, “What’s the chance two serial killers would be in the same car?” Pretty low. So, yeah trust is very important.

Any other tools or techniques that you all have for dealing with these anxieties or stresses or whatever?

KEN: Drinking. Drinking is important. Water. Water.

JAMON: Lots of water.

KEN: What do you think I meant? Oh, come one.

JAMON: Yes, stay hydrated.

KEN: Yes, stay hydrated. Yeah.

JAMON: Actually, along those lines, I started working out a couple years ago, and that has been a really good help for my stress level. When I get through with a workout, I feel better about myself. I feel good. There’s probably some endorphins or something that come with that. And it’s really hard when you are really critically needed at work to take two hours to go workout, but it’s also extremely important for your long-term health. And so you have to prioritize it very high. And you can basically justify it to yourself which I had to do with if I go and do this, I will be better equipped to handle the issues that come up, and it’s so true. Working out has been a very good thing for my stress level.

TODD: A lot of people might be worried about their finances or their spouse’s opinion and that kind of stuff. Which can be super challenging, so you have to deal with that. Another thing that I’ve noticed is, and this is pretty common, especially in our world, and I have to remember that 110 years ago, Ken’ll tell me a real number, but somewhere around there. Most people worked at home, and most people had their own business. They didn’t call it their own business, they were just a blacksmith, and people paid you to hoove their horses or not hoove.

JAMON: Shoe.

TODD: Shoe.

KEN: Shoe.

TODD: Shoe their horses. Thank you. It’s been a while since I’ve lived on the farm about 30 years, but anyway-

JAMON: It’s that a farrier or something?

TODD: Huh?

JAMON: Ken, isn’t it-

KEN: A farrier.

JAMON: Yeah, it’s a farrier.

KEN: That sounds right.

TODD: Whatever that means. Anyways, so you would just do that. You’d just offer your services and that was a home business quote unquote. But, you know, since we all grew up in the late 20th century or the 21st century, for our younger listeners, you know that has been not the normal but the minority. And so a lot of people I’ve talked with, they said, “Well, can I do that? Do I have the permission to do that or whatever?” And it is kind of hard to get to their skull like who are you asking permission from?

There isn’t … there is the government who has rules, but despite what you might think about the government, the rules are actually fairly basic and the IRS of course wants you to pay the money, but that’s actually not the difficult to be honest either. So it’s just really an internal stumbling block. You don’t have to ask anyone. You can go right now. Get a business license, and sell bottles of water at a popular park. Right now, and you technically have a small business.

JAMON: Regarding the personal finances side of this, one of the things that my wife and I did early on that really helped was we did a monthly budget. So we used the tool called YNAB, youneedabudget.com, and we sat down every month together, and we entered all of our receipts and we had categories and we split everything up. We were kind of finance nerds during this time, and that was helpful, because it gave us a sense of control over our finances. We knew where we were. We knew whether we had enough money to pay the mortgage. We knew how much, we could specifically tell you what day we would run out of money if we couldn’t bring anything in, and that was helpful.

Now, sometimes the math brings its own anxiety, but at least you know where it is, and it’s not this unknown out there all the time. Actually, more lately, we’ve gotten away from that. After almost 15 years of marriage, and I kind of want to go back to it, because there are some stresses that come from not knowing.

TODD: Yeah, sometimes everything is just fine, but just don’t know it, and you assume the worst because-

JAMON: Exactly.

TODD: -people do. So I have a question for Ken. I grew up very poor, just some background, but later in my early 20s and stuff, my family actually started doing pretty well. My mom and my step-father ran a couple businesses. My brother started businesses and has done very well for himself. So, although, in my younger life, we were almost less than working class, to be honest. Later in life, we had a lot of experience with business. So me being in business was very natural to me, and my family understood, and they actually didn’t understand when I was working for someone else. It was weird to them, but Ken, I know from discussions with you, the opposite was true. From your family, there wasn’t anyone who were business people and that kind of stuff, and it was kind of outside your culture. I would love to hear if maybe that caused any particular issues for you?

KEN: Yeah, for sure. I grew up in what I would call kind of professional slash academic class household. Right? College degrees going very far back in my family. Doctors, lawyers, scientists, illustrators, artists, also but professionals of various kinds. Going back quite a while. There was a flavor of business being looked down upon a little bit, and that was definitely, even when I got to Harvard. There was that divide was still there even though Harvard certainly has both types. The professional type to kind of like, well I’m good at something. I’m really good at this, and I’m so good at it people want to pay me good money for it. And that’s a perfectly good life. And I’m actually here to tell you right now, if you have those skills. If you are happy doing them, you’re in a good position. Should you start a business? The answer is probably no. Right?

I did it because I couldn’t stand not doing it. Right? It was just this terrifying but enticing thing for as long as I could remember to be … I just wanted to be on my own. I want to do this. Ah. Right. It was this dragon inside that I couldn’t contain. In some degrees, it made me a bad employee. Sometimes. Right, because anybody who’s not doing what they’re sort of supposed to be doing is not happy. Right? Jamon, do you want to interject?

JAMON: Oh, I just want to say in Ken’s family if you say someone is a painter, that means that they are an artist, and they paint on canvas. In my family, if someone’s a painter, that means they spray paint on houses.

KEN: Yes.

TODD: In my family, if someone’s a painter you’re like, “Oh, he’s got a job. That’s wonderful.”

KEN: Yeah, so the three of us we talk about this class stuff all the time because when you start talking with people who grew up in different backgrounds, you start to realize what your blind spots are. Like, I remember Todd saying, growing up people who went to the movies were rich or something like that. Todd, do you remember what some of your things were?

TODD: Oh, there’s a long list of what rich people do that most people would find amusing.

KEN: For me, not only … I grew up in a fairly prosperous town. I would say. Right, but I wouldn’t call it, there weren’t a lot of rich, rich, rich people, but it was prosperous. And then going to Harvard, of course you get exposed to all sorts, and you start to realize how high the ladder goes. Right? And that gave me I think a sort of warped perspective on life. And Todd’s perspective was warped in a different way. And by sort of, not like the three of us, by any stretch of the imagination, now encompass an enormous swath of life experience.

JAMON: No.

KEN: We’re all white dudes for one thing. Right?

JAMON: Yes.

KEN: But nevertheless, it gives us sort of perspective on things that helps. It blunts some of the fear.

JAMON: Mm-hmm (affirmative)-

KEN: To have that breadth of perspective.

TODD: I’d like to ask Ken, because your family culture wasn’t business-oriented, and as you just mentioned, almost a little bit looked down upon business people, I guess for the crassness of it all.

KEN: It wasn’t overt, but it was definitely outside of our purview.

TODD: And definitely your friends from Harvard who weren’t in business school or that kind of thing … do you, like for me. It’s easy for me. The bar was so low. I surpassed almost everyone I grew up with long ago.

JAMON: Yeah. Similar.

TODD: I don’t have to prove anything to anyone.

KEN: Well, so at this point I don’t care very much. At this point, I’m doing my thing and that’s that. However, I will point out there is something very interesting about Silicon Valley. Which is that Silicon Valley is a business culture that was grown by people kind of like me-

JAMON: Yeah.

KEN: -from the professional and scientific culture.

JAMON: That’s true.

KEN: And as a result, that is where, I think, I’m not a sociologist. I haven’t studied this or anything, but my theory is that that’s where that sort of disdain for lifestyle businesses comes from. I think it’s seen as sort of a grind. Where you’re getting paid for the brilliance of your idea, you’re just getting paid for hard work.

JAMON: Yeah, I think that this idea of a lifestyle business, which I don’t have any negative connotation whatsoever. In my world, a lifestyle business sounds like a luxury.

KEN: Luxury.

TODD: Luxury.

JAMON: Okay, we’re gonna have to link to that YouTube video.

TODD: Yes.

JAMON: But some Monty Python there. But I think that’s actually something that was really, really helpful was when we merged was the idea that we can design this business to be lower stress. That doesn’t mean we take our eye off the ball, which we kinda did for a little while there. That doesn’t mean that we don’t work hard, cause we do when the situation demands it, but we can design the type of business where the general day to day things are not drudgery. They are things that we enjoy doing. That we’re good at, and that we can contribute to the success of the business. And I think that that’s something that’s actually overlooked a little bit when you’re owning a business that you do have the ability to change things. You have the ability to enact change. It may be painful. It may be hard. It might be expensive, but you can look at something and say, “You know what, this isn’t fitting for me, and I’m gonna change it.”

Whether it’s cutting off a client that’s being too stressful. Whether it’s hiring someone to do something that you’re not good at. All of those things are things that you can do. My sister started a small WordPress website company. So she’s building WordPress websites. And she asked me for a lot of advice along the way, because she knew I’d kind of-

TODD: Is this Meredith, Jamon?

JAMON: Yeah. That’s right that’s Meredith. And one of the things I told her was that you want to stay with your kids. You want to be at home. You want to build this business that does not interrupt those things, so make those very core priorities. When you make decisions, they should be based on whether they enhance that or take away from that. It kind of gave her permission to look at things through that lens. That you don’t have to necessarily measure it on dollars and cents or even things like customer satisfaction. That may be a goal and you don’t want to let people down, but ultimately you don’t want to let your family down. And that’s something that I think is really important. So for her, you know her husband’s an engineer, a mechanical engineer. He makes good money. It’s not something where they have to have the business, but she wanted something that challenged her while she was also able to be at home, and I think it’s done that.

TODD: And the people she worked with on her team are similar, correct?

JAMON: Yeah, that’s right. So she not only provided a business that works for her, but also for the people on her team. So she actually has people that do code. That do design. That do content. And in many cases they are people who stay at home with their kids. And that’s kind of a cool concept that there could be a business that enables that.

TODD: I think that super important to mention the reason why, because people think that their business has to be like they see on TV or they read about it in a magazine or a book or whatever, and it doesn’t. What principles you base your business on is up to you, and then your job is to figure out a way to make that happen. I think it’s awesome that she wanted to help herself and her team who want a particular lifestyle and still be able to have this business, and she’s doing it, and that’s wonderful.

KEN: Yeah, and I think it’s worth saying on the list of reasons to start a business, getting rich should probably not be your number one. If getting rich is your number one reason, well I mean that’s fine, and depending on your personality, it at least has that as a possibility.

JAMON: Sure.

KEN: Whereas most jobs done. At least not on any sort of short time frame. The number one reason to do it is ‘cause you want more control over your life. And that’s why we did it. So the first year that I took off, when we were still trying to build an ap and we hadn’t done the consulting yet, my daughter was two, and to save money we took less daycare. I had to still have some, ‘cause we both work, but did less daycare. So I spent time with her. I cooked for the family. I found all these ways to save money, and I was sort of part-time house husband while this was going on, and even if the rest of this fails, right? Even if we crash and burn, the chance to have that year and do that will be with me the rest of my life.

So, part of our mission here at Infinite Red, and something we’ve always agreed on is that we don’t just want a successful business. We have to do that in order to make the rest of this work. And it’s a perfectly good goal in itself, but that we also want to be an example of how work can work. Right? Not that there aren’t others, but this is us. This is what we think work should be like. Not that it’s never intense. Not that it’s never hard. Not that it’s some sort of walk in the park. It is not. But that it can co-exist with the rest of your life in a much more harmonious way than has been the model for 20th century corporate whatever.

TODD: Yeah, there are other ways to run a business, all of them are wrong.

CHRIS: Ken do you think that when we … that struggle occurs when we move away from those principles and values and what’s important to us as business owners or whatever that label would be? So like, when you move away from maybe wanting to spend time with your family or building a company where it fuels the lives of your employees. You know, do you think that fear and intention is magnified if you move away from those things?

KEN: What do you mean by move away from those things?

CHRIS: So that they’re no longer a priority. Maybe you’re making decisions that go against those values.

KEN: That is definitely a source of stress. And the fact of the matter is, we are still a business. We still have to operate in the same environment that every other business does. And we have to compete against businesses that don’t operate the way we do.

JAMON: Right.

KEN: And to whatever extent our values create, like I said, put us at a disadvantage, and I think sometimes in the short term that is true. We sometimes have to make hard choices in order to survive and work another day. And I think there’s probably kind of a core, not exactly explicitly articulated, there’s some core that we won’t push past, but when we have to hopefully temporarily do things that are different from our stated values. Yeah, that’s rough. Absolutely rough.

JAMON: Yeah.

KEN: The trick is to kind of figure out … this is why it’s so important to figure out what your real values are. Right? And we’ve had to sort of narrow it down in certain places, because if you have this long list of things that you claim to care about, but that’s not actually true. Right? Then, when it really comes down to it, there are some things that are more core than others. If you die on the hill of one of the non-core ones, and it causes you to fail, that is an unacceptable outcome. And so, figuring out which hills you’re really willing to die on and which hills you’re not willing to die on is super important and there’s not really a shortcut. It’s something that you figure out as you go along.

TODD: If you’re getting chased by zombies through a forest and the zombies are starting to catch up to you, sometimes you have to give grandma a cookie and push her down the hill. That’s all I’m saying. It sucks. It’s against your principles, but grandma’s lived a good life, and she loves those cookies. Fact.

JAMON: I don’t even know how to follow up on that one, but one of the things I was asked early on when I started my company was, what are your core principles and I kind of fumbled through an answer, and I don’t even remember what it was at the time. But I actually think it was probably not reasonable for me to even know what those were at the time other than personal values, but over time, taking lumps here and there and bruises, and the stress and anxiety of various situations, it’s made it very clear what is really important. At the time I was young, I was idealistic. I didn’t really understand what could go wrong. What mattered. What didn’t. But I think that all of those stresses and fears eventually taught me a lot of things and so in a lot of ways, even though they kind of sucked at the time, they were necessary to get me to who I am today. You know, I don’t want to go back and relive them, but I wouldn’t trade them away.

TODD: Yeah. Yeah. For sure. Well that was super interesting to me. I knew some of that. I learned some new stuff which is always fun, and I hope it has some value to the listeners for sure. You know, our experience. At least it’s hopefully an interesting story if nothing more.

JAMON: Absolutely.