Hi friend,
This month, we stayed a little closer to home.
We sat down with Chicago-based owner Jim Hanlon, a serial entrepreneur who has built, bought, and invested in businesses across very different categories — from ice cream shops to firewood distribution to remodeling. On the surface, they don’t have much in common. Underneath, they share the same operator: someone who believes execution beats excitement, people decisions compound, and knowing your numbers is non-negotiable.
Jim’s story isn’t about a single breakout moment. It’s about the steady rhythm of ownership: placing bets on people, navigating doubt, reinvesting when you didn’t plan to, and choosing focus over the thrill of the next thing.
Before we dive in, a quick welcome back to Owner to Owner. This is a private email series for owners, by owners, and about owners. At NGP, the most durable insights consistently come from operators in the seat: people making real decisions with real consequences. Each month, we ask one owner five straightforward questions, followed by our Three Cents on what their experience might mean for how you lead and operate your own business.
INTRO: Jim Hanlon What does it look like to run multiple businesses without losing clarity? How do you manage the mental weight that comes with ownership while still moving forward? And when do you stop starting... and start refining?
Let’s get into it.
FIVE QUESTIONS
1. When did you get started as an entrepreneur, and what shaped the way you think about building a business?
I got started as an entrepreneur in 1995, after working in the ski and snowboard industry as a manufacturer’s rep and then getting the opportunity to build something of my own. But the mindset started earlier.
My mom used to tell me I “liked the finer things in life,” which was her way of saying I needed to figure out how to make money for myself. My uncle was a successful entrepreneur and he gave me advice I’ve carried ever since: “Position yourself well, then go out and execute.”
That combination of ambition and execution has shaped how I’ve approached every business since, whether I was starting one, buying one, or investing in one. Today, I own three businesses. Triple Scoop’d Ice Cream Shop, Chicago Firewood, and a remodeling investment company.
2. What was one decision you made that had an unexpected positive outcome?
One of the biggest inflection points for me was realizing how much growth comes from the people you choose to bet on. I remember one salesperson I hired years ago whose resume I had actually marked up with notes like “monotone, boring, and dull,” and on paper, he didn’t exactly jump off the page. But I took a chance on him, and he turned into a really strong employee. Experiences like that taught me that some of the best outcomes in business come from seeing something in people before it is obvious to everyone else. Over time, that shaped the way I think about building a company: if you hire the right people, develop them, and put them in the right roles, they can become one of your biggest drivers of growth. That’s why I believe so strongly in hire well, train well, and retain well.
3. Can you share a challenge you’ve faced and what it taught you?
One of the biggest challenges I faced was simply managing doubt. You can be doing the right things and still feel pressure, and like I say, you have doubts every month of your life. I’ve felt that recently with Chicago Firewood, where I had to put more money back into the business than I expected, and that creates real pressure. I also had my ice cream shop broken into, and it was actually the second time it happened. Although it wasn’t a major financial hit, it was tough to deal with psychologically because it had me thinking about what could have happened if one of my employees had been there. That type of thing is not easy to deal with. Those moments remind me that hard stretches are part of ownership, and you just have to keep going, keep improving, and trust the process.
4. What advice would you give to other business owners?
First, know your numbers, know your numbers, know your numbers. I’ve seen too many owners get themselves in trouble because they don’t really understand their P&L or don’t stay on top of budgeting. The other big one is making sure you have a real edge. Even if you’re in a business that sells a commodity, you still have to give customers a reason to choose you. That’s how I think about Chicago Firewood, we listened to chefs, figured out what they cared about, and changed how we deliver and serve them, which helped us build something different. Ultimately, you have to really understand the customer’s needs before you can expect to build something they’ll pay more for.
5. What are you focusing on next?
Right now, my focus is on execution, not starting anything new. My wife has already told me, no more buying businesses, and she’s probably right. I’ve got enough going on, and the priority is getting Chicago Firewood fully stabilized and consistently in the green each month. I do have a few ideas for Triple Scoop’d, including a vehicle for off-site ice cream sales and building out more group-event sales, but those are secondary right now. My main focus is continuing to improve the businesses I already have and build them up the right way.
Our Three Cents
1. Choosing where to focus is half the job. What stood out to us was the intentional narrowing of focus. With multiple businesses and new ideas on the table, the decision wasn’t to add more — it was to steady what’s already there. We see that at NGP too. The businesses that create long-term value aren’t constantly reinventing themselves. They get clear on where they can win, and they commit to improving that business month after month. Yes, innovation and reinvention has a core place in a business, but only after clear and focused activity rooted in real customer needs.
2. People decisions quietly shape outcomes. Taking a chance on someone. Investing in them. Moving quickly when the fit isn’t right. Those decisions rarely make headlines, but they change the trajectory of a company. We’ve seen that again and again. The right operator in the right seat can accelerate everything; the wrong fit can slow even a strong business. Leadership shows up most clearly in those calls.
3. The weight of running a business is real — and normal. Jim spoke about reinvesting more cash than planned, dealing with setbacks that aren’t catastrophic but still rattling, and the occasional doubts. All of that is...ownership. What tends to separate the steady builders is not the absence of doubt, but the return to fundamentals: knowing the numbers, staying close to the customer, and focusing on consistent execution of the fundamentals. If this season feels heavier than you expected, that doesn’t mean something’s broken. It likely means you care — and that you’re carrying responsibility the right way.
This conversation carries its own kind of weight and candor. Thank you for joining us as we stepped into Jim’s world and the realities that come with building and steadying a business.
If something here sparked a thought, a question, or a story of your own, just reply. We read every note. And if you’d like to be part of a future issue, say the word. We'd be thrilled to highlight you.
Until next month. We’ll see you soon.
- Victor & Brian
About Owner to Owner
This is a new private email for owners of B2B businesses in the US. Hosted by two longtime business owners, Brian O'Connor and Victor Saad of NextGen Growth Partners, we share personal interviews, honest lessons, and draw connections back to your work and life. Glad you're here.