Why Dave Olsen Believes You Can Have Both Impact and Freedom

Dave Olsen’s entrepreneurial evolution began with a bold question: “Why can’t you have both?” That mindset shift sparked the creation of Nimbl, a modern accounting firm built to liberate founders from the grind of back-office chaos. His journey—from chief everything officer to architect of a self-scaling company—is at the heart of this Wantrepreneur to Entrepreneur Spotlight story. Dave’s success proves that with the right systems, leaders, and mindset, you don’t have to choose between impact and freedom—you can design for both and build a business that thrives while you sleep.

Hi, Dave Olsen! Thanks for joining us today. Tell us about your business. Who do you serve, how do you serve them, and what's the impact that your business and work makes?

I’m the founder & CEO of Nimbl, a modern accounting company that gives owners of sub-$10 million businesses back their time, clarity, and confidence. We combine people, process, and tech to run our clients’ entire back office, including bookkeeping, payables, payroll, tax, CFO, and even global staffing and IT. We enable founders to graduate from “chief everything officer” to true CEO because the numbers, compliance, and day-to-day admin are handled by a team that scales with them.

Tell us about the moment you finally felt like you went from wantrepreneur to entrepreneur.

It clicked the day I handed off my last client as the primary point of contact. For years I’d been the only face our clients knew, then I began gradually introducing them to a growing, trusted team. Watching that last client effortlessly embrace their new Nimbl relationships, without needing “Dave” involved in everything, was equal parts relief and pride. In that moment, I felt the shift from technician and wantrepreneur to true entrepreneur: someone who builds leaders and systems that outlive any single founder.

Describe the moment or period in your life/career that motivated you to make the entrepreneurial leap.

I began to see the bigger vision in 2015, when I expanded my offshore team to handle bookkeeping and admin. Overnight, literally, work continued while I slept, and a new possibility snapped into focus: with the right mix of people, process, and tech, I could offer fractional finance at scale to owners of sub-$10 million businesses who didn’t even know it existed.

Then the voice of doubt chimed in: Sure, you can build a bigger company… but at the cost of my health, my family, and my sanity.

Enter Brandon Craig, an executive coach who’d reached out as a prospective client. While I explained my either-or dilemma, he stopped me cold with one question: “Why can’t you have both?”

That challenge broke the spell. I realized the real limit wasn’t time or money. It was the systems and leaders I hadn’t built yet. From that moment forward, scaling Nimbl became my proof point that impact and lifestyle can coexist when you design the business on purpose.

Describe a tool, service, or software that has been a game-changer for your business. How does it contribute to your success?

Ignition is the quiet powerhouse in our tech stack. Every client engagement begins with an Ignition proposal that captures the scope, obtains e-signatures, and auto-charges the full monthly fee on the first of each month. Because cash lands before payroll goes out, we never chase invoices, carry receivables, or worry about working-capital gaps. Growth effectively funds itself. The platform also eliminates hourly billing and collections headaches, so our team focuses on delivering value instead of tracking time. Best of all, Ignition handles proposals, renewals, and payments in the background, allowing us to manage millions in recurring revenue from hundreds of clients with only a few hours of admin effort each month.

We know that success is very often a non-linear path. Tell us about a failure, pivot point, or lesson that changed your course or direction and helped to get you where you are today.

One of my biggest face-plants came as I began to “free myself” by hiring a client-facing teammate. I was buried in my own client work, so I transitioned a number of accounts to the new hire and got back to work. It wasn't long before hard-won clients began to cancel. Turns out my new hire had no idea what they were doing. That pain was the wake-up call: hiring and delegation without structure is just abdication. I upgraded the hiring, training, and performance management process, and, just as important, used the fiasco as motivation to exit day-to-day client work as quickly as possible so I could focus on creating the system. The lesson still echoes inside Nimbl: leaders build systems before they let go.

What unconventional strategy did you employ that significantly impacted your business?

We built a truly blended U.S.–Philippines team from day one. Instead of outsourcing tasks, we integrated offshore talent into client workflows, paired them with U.S. client relationship managers, and focused on culture + process so geography disappeared. The cost leverage is obvious, but the real win is 24-hour workflow and a deeper talent pool.

What’s something you wish you knew sooner that you’d give as advice for aspiring or newer entrepreneurs?

Lead with clearly documented agreements, not loose expectations. Clarity up front saves 10X the time and emotional energy later, whether it’s with clients, hires, or even co-founders. Write it down, agree to it, revisit it. Your future self (and team) will thank you.

Want to dive deeper into Dave Olsen's work? Check out the links below!

• Visit Nimbl's website: trustnimbl.com
• Connect with Dave Olsen on LinkedIn: Dave Olsen