The Challenges in Building a Business with Family
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In Chapter 4 of 17 in his 2011 Capture Your Flag interview, education entrepreneur J.T. Allen answers "What Has Been Most Challenging Building a Business With Family?" Allen shares generational challenges as well as finding separation between personal and professional. Allen details how working with his mother has impacted how their relationship has developed over time. J.T. Allen is the CEO and co-founder of myFootpath.


Erik: What has been most challenging building a business with family? J.T.: I would say building a business with family always has challenges you know because you’ve got personalities of people and you know you’re going to see the family members whether the business succeeds or fails. So you’ve got to take that into account and make sure that--I think--that you got to make sure that you’re just open and honest with them about expectations of them to participate in the business or not, right? Financial commitment if any and understanding your sort of timeframe and you know how you’re going to measure success. And it’s hard you know because your family often times will be the ones to say, you know, “Why are you doing this? You can go get a job and make money.” It’s a known entity. You know I remember when I started the business I’ve – you know I told my father I was doing this and he said, “That’s the dumbest thing I’ve ever heard.” You know and here he was you know he’s an educator, life long educator, administrator you know he could see his career at 25, right? In his third year of teaching and then he could see his career you know charted out and this is what he was going to make and you know and what I realized was he really came at life just different than I did, right? I looked at it as, “What do I’ve got to lose? I can always get a job, right? I’m smart. You know somebody will hire me.” And you know maybe it’s not the perfect career track or whatever but I kind of looked at from the downside and said, “Yeah, it’s not that – it’s not that painful.” But you know that family and then you know he’s not really in the business you know my mother is in the business because they’re divorced and working with my mother is just you know she’s really become more of just an adviser to the business today. She was very helpful with the first two revolutions that we went through and now we’re on our third. The third one she doesn’t really know much about so she you know was happy to offer her opinion and encouragement and support but just not her sort of bailiwick but you know on the first two she was very much involved and so a lot of back and forth and you know you just work with them in ways that you never did but certainly I think is – for us I think it’s expanded our friendship, you know it’s expanded our relationship you know as mother and son and you know it’s always something, for me, it’s always something I like to talk about, right? So you know I’m not as interested in talking about you know okay, what happened to the high school grad that just got married and you know was in the paper, right? This is something where you know we can kind of relate and talk about it at a different level and really have a dialogue that you know is positive and you know it’s great. So she’s probably the biggest supporter of what we’re doing and you know hopefully it succeeds and you know we both make a little bit of money at it.