Watch: Entrepreneurship in Family Enterprises — Panel Highlights

Jason Packer: I wanted to thank everybody for joining us this afternoon for our Stride panel discussion, with some incredibly successful family businesses on the call.

On what it means to be entrepreneurial

Darrin Jahnel: My brother is my business partner. Our parents were school teachers, so they were not entrepreneurial. The way I look at it, it’s really just a desire to start businesses and to constantly look to solve problems and do things. My brother and I had 14 failed startups before we got a winner, so it’s almost an obsession — something we can’t control. We’ve got a portfolio of three companies now, and I’m literally starting a fourth because I just can’t stop. It’s a compulsion. Fairly intense, but you’ll see that as a trend in my answers today.

Nick Di Loreto: Fourteen failed startups, or fourteen learning opportunities?

Darrin Jahnel: Fourteen learning opportunities, for sure — but definitely failures, let’s be real. Some of them were the worst companies you could ever imagine. But with each one we got a little better, a little smarter. A lot of pain.

On a moonshot only a family business could fund

Arnaud De Coninck: This brings me to a project called Solar Impulse, the first solar-powered plane to travel around the world with a pilot. Solvay was one of the key partners in the adventure: something like 50 different products across more than 6,000 parts of the plane. It was really a flying research lab, in development for 12, 13, 14 years, with no revenue line and no guaranteed payoff. There was clearly risk in all of this, and I think only family shareholders who are anchored behind the business can really support initiatives like that. I say it had two payoffs. One, it was successful: a lot of the products that were in research and development then are performing super well for the company today. But it has also been an identity project, something we’re proud to tell our kids about. Entrepreneurship needs a story. It’s super important to have the story, and for those stories to be able to travel across generations. This one did, which is why I chose it as an example.

On a spreadsheet that became a company

Adam Holland: Our business is property management. A couple of years ago, during COVID, my father came to me and said he was struggling to keep track of everything that needed to happen — rent payments, work orders, leases — and he was doing it all in his head. He decided he didn’t like that, so I was going to get to do it now, which was delightful. I made a spreadsheet to keep track of everything, because I knew I couldn’t do it in my head. He liked it, our team liked it, and I set it up to be automated so it came in every day, color-coded to show them exactly what they needed. We showed some other people in the industry, and they liked it too. So we decided to turn it into its own product. Three or four years later, I implemented our third customer — the first one to actually go somewhere — this morning.

On the start that almost broke him

Darrin Jahnel: That was probably our 12th company. We had built an educational software program and pitched it to 12 schools. We took a week of vacation from our full-time jobs, and 11 of the 12 said, “This is awesome. We’re going to buy it.” We were high-fiving in the parking lot: we’re going to be rich, this is easy. So I quit my job. We were living in Manhattan, and my wife had a good job; she quit hers because we were pregnant with our first child, and we moved to Upstate New York, about two hours north of the city in the Schenectady–Albany area. We bought a house. We’d both quit our jobs, but I was going to be rich, so no problem, right? Then I realized that just because someone says they want to buy something doesn’t mean you’re going to close the deal. I was young and naive. I didn’t understand the difference between a verbal “yeah, let’s do it” and actually getting money out of a school budget. We closed zero of those 11 verbal commitments and went a full year without selling anything. My wife and I ate through all of our savings and went $70,000 into credit card debt. That was my start: no job, 70 grand in debt, a house, a wife, and a baby. It was brutal. But I was a software engineer, so I took two full-time contracts and did them both for 11 months — 80 hours a week — and dug out of the debt. It’s a story about grit. If you live in America and you’re willing to hustle, you’re going to be okay.

On growing through a crisis

Jason Packer: We began to predict: okay, we’re probably going to have to lay people off, lower salaries, cut back. My mom’s perspective was, no — how can we grow? What could it look like if we decided we wanted to grow in this moment? It was a mindset shift more than anything else. Instead of thinking about cutting costs, we started thinking about growing customers, growing product lines, and finding new opportunities. We were on a phone call with China trying to get a million dollars’ worth of face masks. A large portion of it was on its way to America, sitting at the Shanghai airport ready to be put on a plane, and the Chinese government said, “No, those are our face masks.” We had already placed the orders with our customers; they had put money down. So we scrambled, found ways to bring products to people, and ended up growing the business — historic revenue, historic profit. The next year was the same. It created a new muscle in the business.

The four S’s of an entrepreneurial family

Nick Di Loreto: Number one — we’ve already talked about it — is stories, and this idea of the oscillating narrative. If everyone thinks everything is positive all the time and you’re trying to develop an entrepreneur, the first moment they have a setback they’ll fall by the wayside. So find the stories that tell that oscillating narrative. The second is structures: how do you put structures in place that enable decision-making and clarify opportunity, especially in families that are further along — second, third, fourth generation? Process before people. All too often in later-generation families, if Jason is my eldest and he’s the first to ask and we say yes, and then Arnaud is my second eldest and he asks and we say no — did we say no because we like Jason better than Arnaud? Probably not. But without a process or a policy in place, it’s easy for those misconceptions to take hold. Three is support: financial, perhaps, but also non-financial — connections, know-how, mentorship. How do you build those networks early, so your next generation or your employees know that entrepreneurship is a feasible path? And finally, space. I’m the father of three daughters, and I find it very hard not to give advice every time they come to me with a question. The most important thing I’ve learned is not to give the answer, but to ask questions and help them solve their own problems. The same holds for cultivating an entrepreneurial mindset: give people space to learn, to chart their own path and, perhaps most importantly, to make their own mistakes.

On starting a company in the age of AI

Darrin Jahnel: The ability to start a one-man company now has 100x’d your odds of success. The new company I’m starting, I’m literally doing by myself, using AI to write the software. I’m absolutely obsessed — back to 70-hour weeks — and it’s not possible without AI. What I’ve done in the last four months would have cost me probably half a million dollars, maybe 750K. I’ve done it for about $1,000 in tokens. It’s unbelievable.

Advice for the next generation

Nick Di Loreto: What piece of advice would you give them?

Darrin Jahnel: It goes to something Arnaud said: never give up. Now, you might need to give up on an idea and pivot — that’s hard to know, when to give up. But if you say, “This is what I’m going to do, and I never give up; I’ll just keep pivoting,” all you’ve got to do is find one successful idea.

Jason Packer: Keep adjusting. The original idea may end up being a completely different idea. Keep recognizing what your customers need and adjust to that, because they’re really the decision-makers — they’re your boss. Keep figuring out what they need and how you’re solving problems for them, making their lives easier, making things more seamless.

Adam Holland: Ask more questions. That’s how we learn.

Arnaud De Coninck: Just go for it. It’s so easy right now to start a business. Try it out. Listen to your customers — like Adam said, ask more questions. Connect with networks. And, as someone in the comments said, educate yourself: by connecting with networks, you meet peers and learn from peers.