Entrepreneur 2 Entrepreneur: The Okiror Bros. On Mixing Business With Family



The Entrepreneur 2 Entrepreneur (E2E) series is curated by Sean Higgins and underwritten by Router Ventures.

Starting a tech business is like driving your car through the desert while your tank is almost always on empty and the next gas station is in 100 miles away.

Having the right passengers with you in the car helps, but you better be prepared to disagree, debate, and discover with them. This dynamic can push relationships to the brink.

So when you start a company with someone you are related to – how do you manage to keep business from ruining your existing relationship?

We catch up with brothers Simon and Jesse Okiror at Suprabook to learn more about how they are doing it:

Sean: Let’s dive right in! First off, just what is Suprabook?

Simon: Suprabook is an app that replaces printed litigation binders. So, it lets lawyers build them digitally, saves time, money and is more dynamic than the current process.

Sean: Jesse, how far along was the company/concept when Simon joined you? Whose idea was it originally?

Jesse: It was Simon’s idea to join me at Suprabook, and it came about in the best possible way for a startup in need of talent.

By September 2017, I’d built a prototype and was trying to raise money to build the MVP. But I knew it would be pointless if I didn’t have a marketing plan. I started asking marketing consultants about the costs to execute a product launch, and I asked Simon to help vet these consultants based on his experience. After every call with a consultant, Simon typed up his thoughts and emailed them to me. Then he just started sending me his ideas. After a while, he’d pretty much started writing the marketing plan. He was clearly excited about the project. I think this is what he’s always wanted to do. After about a month of helping out, Simon proposed taking over Suprabook’s marketing. I loved the idea personally and it was an obvious win for the company.

Sean: So the team is you, Jesse as CEO, and your brother, Simon as CMO. How would you describe your role, Simon?

Simon: I started as pure marketing, but coming in at the beginning of a startup I’m a co-founder. I’m doing a lot of fundraising, helping test the product, trying to get into accelerator/incubator programs like beta.mn, and now that we’re getting close to launch I’ll actually be doing the traditional marketing roles.

Sean: So, the question that I’m dying to know…people say, ‘Never start a business with family with because it creates too much conflict and risks ruining the relationship.’ How do you handle the conflict, the stress, from start to finish?

Simon: We’ve obviously known each other forever. We ended up going to undergrad together too so we crossed paths over there but this is really a business relationship. We get on the phone every day and we talk straight business and we don’t talk much about stuff outside of work. It’s kind of funny, we talk a lot more now than we usually did.

Sean: How did this happen?

Simon: Before I joined I was kind of helping him on the side by finding an ad agency for him that could help him with the marketing. And then I realized I could do a lot more for a lot less. It helps though that he’s my older brother and my boss.

I think it’s a good balance because he knows the legal side and as the CEO he ultimately makes the final decisions about stuff. But, I have more marketing and sales background so even if we’re talking to investors or agencies that’s where I have experience. We kind of balance each other out.

Sean: You both work across the country from each other right now. How does that affect the business?

Jesse: It’s actually been advantageous in the early days. Simon joined the company and immediately had to fly solo with customers and investors in Minneapolis. Now he can pitch Suprabook better than I can. That might not have happened if I’d attended those meetings and taken lead as the lawyer who invented Suprabook. That said, we’re approaching the point where we should be in the same place more often. The pitches are bigger. Adjustments and iterations happen faster. I may need to move to the Twin Cities.

Sean: How do you guys handle disagreements?

Simon: We come to the agreement that whenever we have issues we don’t try to settle it right then and there. We talk about it one day and revisit it a couple days later. We usually both come with an idea of how we can solve it and then we decide what we go with.

Jesse: We talk about it until we both agree. We can do that because we’re brothers. First, our conversations are fast because we use the same expressions, shorthand, and cadence. We literally need less words. Second, there is total trust. If Simon takes a position different from me, it’s because he 100% believes his position is best for the company. There is no ego or competition between us.

Sean: If someone were thinking about starting a business tomorrow with a close family member, what are the tips you’d give to help them stay sane through the whole process?

Jesse: Have the business conversations early and take them seriously. Simon is my brother. Every investor in Suprabook is a friend and many of those friends are like family to me. Their relationships to Suprabook are cleanly-documented based on arm’s length negotiations. Everyone knows where they stand in good times or hard times for the company. The friends and family you want involved in your business will respect that.

Simon: I think you have to make sure you have the different skills to balance each other out. If we were both lawyers and neither of us knew marketing we’d have a huge blindspot so whoever that other person is they need to balance you out.

Sean: So, to you, it’s less about what the relationship is and more about if they have the skill set to accomplish and implement what you want to do.

Simon: Exactly. And definitely don’t take things personally. It might’ve been trickier if our family already talked a lot but we didn’t so this business relationship works well.

Sean: You mentioned you haven’t worked together much. Do you guys still do joint family things like going home for the Holidays?

Simon: Yea, we’ll be going home for sure.

Sean: Okay, I’m going to paint you a picture. Imagine things are tense with the business next month…what is a holiday gathering going to be like?

Simon: Yea, I think we’ll do a pretty good job keeping the work and personal separate. But it is good actually getting together like we were during startup week. It was helpful to get a chance to work through some things we didn’t get a chance to work through. We’ll probably work over Christmas either way.

Sean: What’s the hardest part about having your brother as your business partner?

Jesse: It’s been great so far so I can’t say there’s anything hard about it. But one thing I’m curious about is whether we can turn off our business minds when we’re together and if we even need to. Thanksgiving is coming up. Will we be off to the side talking about Suprabook while the rest of the family has a normal holiday? That’s what we did last Thanksgiving and we got a lot of work done.

Sean: So in terms of keeping work and personal separate, what are the tips and tricks you guys use to do that?

Simon: We talk during our set times which helps. I think we know we need to be available. I think too, that could be one of the positives of not being right next to each other because by the time I get to talk to him I’ve already thought through and figured out how to condense my questions and ideas down. It’s kind of efficient that way.

Key takeaways from Simon & Jesse on working with family:

  • Just like any founding relationship keeping clear and consistent communication is huge.
  • Keep those conversations on track and you’ll be able to avoid some of the blurring between work/personal.
  • Do not work together just because your family if you don’t cover each other’s gaps it’s just not worth it
  • When you do get into heated disagreements have established ground rule beforehand for how you will handle it (hear the other side, then regroup strategy Simon and Jesse use)

Keep these tips in mind and you’ll have more successful founder relationships no matter who you’re building your business with.