Entrepreneurship Through Acquisition

Failure Often Precedes Success: On Resilience, Search Funds, and Starting Over

Listen to the full episode on Transitions, or browse more conversations on the Oberle Podcasts page.

Who I am

I am the Founder and CEO of Oberle Risk Strategies, an insurance agency in St. Louis serving a national client base, with a specialty practice for search funds and acquisition entrepreneurs. Insurance is in my blood: my father, grandfather, and great-grandfather all owned insurance agencies in St. Louis. Over the past twenty years I have bought two companies using the search fund model, sold one, and learned most of what I know by getting things wrong first.

Tim Ludwig invited me onto the Transitions podcast to talk about the pivotal moments behind that path. What emerged was a theme I had not fully articulated before: failure has often been the precursor to success in my life.

The school that pulled me along

People usually point to college as the transformative chapter. For me it was high school. I was lucky to attend John Burroughs in St. Louis, a small, rigorous school where you start in seventh grade and stay through senior year. I was not one of the exceptionally smart kids. I felt right down the middle, and at that point in my life I was not ready to push myself. I needed to be pulled.

"It was such a special place, and it just sort of pulled me along. I got into this fast current of people that were very motivated. It has a culture where the cool kids get As. You weren't made fun of if you were a nerd, you were celebrated." August Felker

The culture did the pulling. Morning assembly run by students, assigned family-style lunch tables with a teacher at each one, and advisors who refused to let anyone fall through the cracks. They even had blue slips you had to get your parents to sign when you were underperforming, and I dreaded bringing those home. It worked. Years later, one of the biggest drivers of moving my family back to St. Louis was so my kids could have that same experience.

Tennis, integrity, and the mentors who set my standards

Tennis was the other formative force. It is an individual sport and a grinder: summer tournaments across the Midwest, just you and your results. Joining the Burroughs team changed that. As ninth graders we decided we were going to win a state championship, and we chased that goal for four years before finally winning it our senior year. It remains one of the best athletic experiences of my life.

Two coaches, Toby Clark and Hobie Holbach, changed my trajectory. Toby was the highest-integrity person I had ever met. Junior tennis has no line judges, so players call their own lines and the gray area gets abused. Toby set the bar that we would be the most honest team in the game, and he enforced it, including making me walk back onto a court to concede a point my opponent had miscalled, even though it cost me.

"It set a bar and a standard that I hope to reach every day professionally. It's rare to find a great coach. I hope I pass on lessons like that to the people who work with me." August Felker

Hobie had a different tool: sarcasm deployed with love. Whenever I slacked, he would ask, "Didn't you say you wanted to be a state champion? I'm just wondering, because you're five minutes late." I hated it and I loved it. Both men were fully present, always on time, always giving 110 percent. The older I get, the more I appreciate how rare that is.

Camp Kieve: learning to lead in the Maine woods

In college, while my classmates chased prestigious internships, I stumbled into a summer job as a camp counselor at Camp Kieve, a renowned boys' tripping camp in Maine. I got the job largely because I showed up to the interview wearing a collared shirt. It turned out to be one of the luckiest breaks of my life, and I went back every summer of college.

My job was to lead twelve kids at a time on multi-week hiking and canoeing trips through the Maine woods, and I was no outdoor expert. My approach was to prepare relentlessly: before every trip I sat down with the counselors who had done it before, maps out, grilling them on where to stop, where to pitch tents, what to eat, what surprised them, and what secrets each route held. I took pages of notes.

"I leaned heavily on the counselors that had done it before. I wanted to know: where do I stop? What did you learn? What were your surprises? I took a lot of notes and grilled the counselors who had done it before." August Felker

Leading kids was its own education. Homesick campers, obstinate campers, kids from every background. The method that worked was giving them problems to solve together: how do we get from this lake to that lake? Appoint a captain, let them argue and debate, and let them own the answer. The goal was for every kid to come out of the woods having developed real leadership and collaboration skills. I also laughed every single day, which was new for a serious kid worried about school and tennis. I still chase that feeling when I think about the culture we build at Oberle.

San Francisco and the fork in the road

After college I moved to San Francisco alone, having fallen in love with the city on a childhood trip. I took a job at a large international insurance brokerage, five hundred people in my office, and the minute I got there I thought: I don't know if this is it. Coming off the energy of Kieve, I was not fired up, and I knew I had to figure something out.

Through friends of friends I heard about two Stanford GSB graduates, Josh Greenberg and John Fowler, who had used a model I had never heard of, called a search fund, to buy a small logistics business in a warehouse district of South San Francisco. They were hiring their first salesperson. I borrowed a car, drove down, and met them.

"I was like, this is it. These are the guys. I don't really care what we're doing, I want to work for these guys. That was my big break, honestly. It was a total gut feeling." August Felker

On paper it made no sense. I left an established institution, took a pay cut, and bet the next stage of my career on two guys with an ugly little company in an industrial park. But they were fun, transparent, and building something with real energy, and they reminded me of the people I loved working with at Kieve. It was the fork in the road that set everything else in motion.

Failing at sales before succeeding at it

My dad had told me sales was a skill I could use my whole career, so that was my job: cold call Bay Area businesses and convince them to ship with us. No lead list, no instructions beyond a general elevator pitch. And I was terrible at it. I got hung up on constantly. The one other salesperson hired with me, sitting right next to me, was having success while I was dying.

The turnaround came from advice I collected by asking successful salespeople how they did it. One man told me: you cannot judge a day by whether you got the sale. Judge it by whether you did the activities. Focus on the inputs, not the outputs. I took that to heart. I got excited about hitting a daily call target whether the calls went well or not. I learned that one no is one no closer to a yes.

"I cold called someone, and they said, is this a cold call? I said, yes, yes it is. And they said, you're pathetic, and they hung up on me. And I remember thinking, that's great! I'm closer to a yes. I went around the office giving high fives. Someone just called me pathetic." August Felker

I built little games to keep going: nine cold calls before 9 a.m., and my first two calls of the day always went to people I knew would say no, because I always stumbled early and those calls did not count anyway. Then the wins came. I landed a couple of major accounts entirely through cold calls, and the confidence compounded. Years later, when I was doing my search, cold calling business owners felt like nothing. If I could sell shipping, I could convince an owner to at least take my call about selling their business.

Launching a search fund in the middle of a financial crisis

When Josh and John sold the logistics business, I told them what was next for me: let's do a search fund. I had conviction around insurance, the industry I had started in. They said they would support me, and the structure we landed on was unusual. They raised the money, helped with the deal, and sat on my board. My job was to run the company we bought, day to day.

Their backing mattered more than the capital. This was 2008 and 2009, the depths of the financial crisis, a brutal time to raise a search fund. I had no MBA from a top program, which at the time was close to a requirement. They went to their investors, put their own names on the line, and said: trust August.

"They put a lot on the line for me helping me raise money. They went to all their investors and said, hey, trust August, do this. They planted the flag and said we're going to do this. And August is our guy." August Felker

My wife Mary was the other unsung hero. She was a rising star at Marsh, handling insurance for Apple, and she agreed to marry me and then to support the search, which came with a hard rule: if I found a deal, no matter where it was, we were going. She left her career, and we picked ten target cities. The business I bought, Murphy Insurance Group, was in Madison, Wisconsin, which was not on the list. Search is emotionally brutal; you come home euphoric or nearly depressed, sometimes both in the same day. One day I told her the Madison deal was off, and I watched her face fall because she had already started picturing our life there. I decided that night that as long as it was still a good deal, I was going to make it happen. We did.

The first acquisition: humbling lessons in leadership

I stepped into the CEO role at twenty-nine, and I was not ready. I struggled with the seller, who stayed on for three years. I did not have confidence in myself as a leader. I was not authentic, I did not listen well, and I came in acting like I knew it all, or at least like I should.

"I don't think I had confidence in myself as a leader. I don't think I was authentic. I don't think I listened well to people. I came in feeling like I knew it all. And I just learned so much by going through that first deal. It was very humbling." August Felker

What saved me was the board. Josh and John were on it, and we talked almost daily, not about fancy board matters but about the real stuff: how did this person handle that conversation, what would you do here. That built-in mentorship is the great beauty of the traditional search model. I also never had anxiety in my life until I bought that first business. It showed up physically, cost me sleep, and I had to learn to manage it. I have come to accept that some of it stays with you, and that a little edge keeps you sharp.

Selling, then starting over with a self-funded search

While I was running Murphy, insurance brokerages became hot acquisition targets for private equity. We ran a process and sold to a large PE-backed roll-up. I was excited to sell, and then almost immediately felt lost. Working inside a huge company after the total control of entrepreneurship was not the right fit for me, and that was a major learning. I still had energy. I still loved insurance. And I felt like the sale had interrupted a learning curve that was just getting steep, because, as Josh and John always told me, you become a far better CEO in your second ten years than your first.

So we did it again. This time self-funded, back in my hometown of St. Louis, and tiny: an agency with five people and roughly $200,000 of EBITDA. The logic was that buying something small beat starting from scratch. A foundation, the licensing, the early infrastructure, it let me skip the first couple of years of a startup and jump in around year three.

"It was tiny, $200,000 in EBITDA, very small business, but I felt like it'd be better than starting from scratch. At least you had something that had some foundation." August Felker

I underestimated how hard the early years would be. Going from a hundred-person company to plugging in ethernet cables myself was a shock. Mary's reaction mirrored mine in reverse: when I was high on the idea she was skeptical, and as we got closer to jumping off the cliff and making no money, I got low and she got high. "You can do this," she told me. It was exactly what I needed. That small agency became Oberle Risk Strategies in 2019.

The power of resilience

When I wrote down what I was most proud of, besides convincing my wife to marry me, it was this: I stick with things. And I failed at almost everything important at first. Sports, sales, leadership. Where does that come from? Some of it was tennis; you lose a set, and you still have two more to play, so you keep going. Some of it was school. Some of it was probably having no other choice.

"I failed at almost everything important that I set out to do at first: sports, sales, leadership. Now, after I screw something up, I'm like, I'll get it right the next time." August Felker

That muscle builds with use. These days I am even experimenting with meditation to start days more even-keeled, twenty days into a thirty-day program, and I am optimistic about it. Resilience does not mean never rattled. It means building practices, people, and habits that let you keep going when you are.

The most surprising thing about my life is that I ended up here at all. Out of college I did not know what private equity was, let alone that I would buy two businesses. What surprised me most is that it is not as hard as you think it is. Day to day is brutal, but in the big scheme, anybody can do it. If there is a will, there is a way. I never thought I could do it. I just sort of stuck with it.

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