Fears and Anxieties of Running a Business

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.

Show Links & Resources

• YNAB: Personal budgeting software
• Four Yorkshiremen by Monty Python

Episode Transcript

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...