From Cincinnati to Appleton: a founder doubles down on the Midwest

David McFarland’s career has always been about risk and tradeoffs. As an actuary he chose roles that paid less but taught him more. “Very few people get rich in their twenties,” he told me. “But you are ripe for learning your craft. Optimize for that and let the money come later.”

That mindset carried into Coterie, the company he founded in 2018 to simplify small business insurance. Since then Coterie has earned national recognition on Insurtech 50 and been named one of Inc.’s Best Workplaces with over $100M raised to date. The growth is impressive, but what stands out is how much it reflects the same philosophy David followed early in his career: sacrifice up front, discipline in the middle, and conviction that it will pay off over time.

Why the Midwest

David grew up in Fort Lauderdale but found his true fit in the Midwest. When it came time to pick a home for Coterie he wanted an insurance town, a good airport and a family friendly environment. Cincinnati checked every box.

The timing didn’t seem ideal. He was leaving a startup that was rocketing upward and his wife was expecting their third child. Advisors told him not to do it. An investor even pulled out the week of his going away party. Through it all he says he was fortunate in one way that mattered most. “I’m probably one of the most fortunate founders out there. Having the right spouse makes so much difference. The fact that my wife is like, oh, it’s cool, we can live on beans and eggs… that has helped me immensely. We’re gambling everything we have, a few kids, like that’s okay, we’ll be fine. It’s refreshing.”

Later, when Coterie was stable and fully remote, the family chose Appleton, Wisconsin. It was a return to a community they loved and a place where raising six kids felt more sustainable. “Every day we’re just so thankful that we moved back,” he said.

Building Remote 

Coterie has been remote since the start. For David it was not about a competitive edge but about how he manages. He looks for experienced people who can manage themselves. He sets a clear vision and expects them to run with it. Accountability is not optional. The company’s KPIs flow down into business unit goals and then into individual actions. People are measured by what they can control, not just the outcomes.

How He Hires

David goes beyond just first principles thinking when hiring. I asked him what he expects from his team that might surprise other founders. His answer was clear: “I value both first principles thinking and experience.”

He explained that many founders only hire for the ability to think from scratch. “It’s gotten pretty normal in founder culture to only focus on first principles thinking. However, people with experience tend to pattern match faster than those who can just think through the problem. In sectors like insurance this is invaluable.”

To illustrate, he used sports. “If you go up to someone who is a D1 basketball player, and you try and play them in basketball, they’re just going to destroy you. A D1 football player is still a great athlete, but they’re not going to understand some of the very basic things about basketball.” In regulated industries, the landmines are real. 

That balance is what he looks for. “I still believe you need to have first principles thinking, but experience is vital as well.” In practice, that means hiring people who have been tested early in their careers, who have quality training and who still have the drive to push forward.

He is realistic about the arc of a team. Founders, he said, should not expect the people who helped start the company to be the same people who take it public. 

Leading With Data 

David’s actuarial background shows up in every decision. “I’m absolutely a data junkie. I love data,” he told me. When a decision is on the table, his instinct is to ask, “What is this? And this? And this?” Once he has the numbers, he runs them at the high and low ends. “At the high end of the range, this is what the expected value is. At lower than range, this is what it is. So we know that it’s between this and this. So let’s make the decision based on that.”

He explained the value of this approach: “Once you just lay out the data the decision makes itself. Our mind’s hyperbolize everything. But when we shrink down into what the reality of the situation is, we can be like, oh, well, this really isn’t that hard of a decision.”

Advice for Founders

His advice is clear in principle and courageous in practice.

“Do things that are first order negative, second order positive,” he said. Saving for retirement, eating healthy, or exercising all feel like losses in the moment but deliver benefits later. The same pattern applies to company building.

He pointed to firing as one of the hardest examples. “So many people, you talk to a founder and they’ll say, oh, well, we didn’t fire that individual because we really needed them to continue our growth. Okay? That’s first order positive, second order negative because we know what’s going to happen in three years when the culture is terrible.”

Board relationships are another test. For David, hiding bad news is never an option. “That dashboard that you’re saying you just do not want to show anyone because it’s so bad. Just copy paste it, put it in the board deck and be like, we need to talk about this.” Before meetings he recommends calling board members directly, not just to flag problems but to walk through the strategy he’s considering. 

It all comes back to the same principle. “Trust the long-term game,” he said.

The Takeaway

David’s story is not one of perfect timing. It is a story about discipline and conviction. For founders here in the Midwest, the lesson is clear. Risk sometimes looks intimidating in the moment, but with the right discipline it compounds into something enduring.

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Amanda Daering is a builder by instinct and operator by experience. For nearly two decades, she has worked at the intersection of business, technology and talent. As CEO of Newance, she works with founders and VCs to grow high-context teams that can scale.