Failure Often Precedes Success

Tim Ludwig: August, first of all, thank you for joining. I’m really excited to have the conversation with you today. And where I thought I’d start, because it was sort of surprising to me, is with your middle and high school. For a lot of people that go on to college, that seems to be sort of the transformative switch to grown-up land and really what defines a large part of their adult life. I got the sense from you that that occurred earlier, that the formative years for a lot of your personal development that have carried on into adulthood started way back in middle school even. And so, I thought it’d be great to unpack that a little bit and maybe have you share about your high school and maybe just some background first on it, the caliber of students, the rigor of the instruction. I mean, it sounds like an exceptionally special place.

August Felker: Yeah, thanks, Tim. I love chatting with you. I heard a while back, a couple of friends were talking, and they were saying, well, where did you learn more? Where did you learn more? Was it in college or high school? And all of them said college. And I always felt, well, I learned a lot more in high school, much more formative for me. And I grew up in St. Louis, Missouri, and St. Louis is really well known. We’re really lucky to have a lot of great schools, and especially high school. And one of those schools is John Burroughs, where I was really lucky to go. And it’s a unique setup where you start in seventh grade and you go all the way through high school and through senior year, twelfth grade. And it’s a small school, there’s a hundred kids in each class and co-ed, independent, and it was always one of those schools growing up that I really was excited about and really wanted to go to. And it’s interesting because when you’re in sixth grade in St. Louis, you have to sort of apply to all these schools if you want to go the private school route. So, it’s somewhat stressful as a sixth grader waiting to hear about where you’re going to get into, and I was really lucky to get into Burroughs. And Burroughs is full of exceptionally smart and talented people. I was not really one of them. I felt like I was right down the middle. There were so many bright people and so many talented people, and I felt like, at that time in my life, I wasn’t really ready to push myself. I kind of needed to be pulled. And Burroughs, it was such a special place, and it just sort of pulled me along. And I felt like I got into this fast current of people that were very motivated. It has a culture where kind of the cool kids get As. You weren’t made fun of if you were a nerd, you were celebrated. And that really motivated me and pulled me along to work hard, get good grades. And especially when it came to thinking about going to college, I really felt like, well, I’ve got to really work hard and get good grades so I can get into a good college, so I can go to a place where all my friends are going. So, I was really, really lucky to go through that whole experience. And I’m sure we’ll talk about it later, but one of my big drivers of coming back to St. Louis, where I live now, was so I could send my kids to Burroughs because it was such a unique place, and I really want to replicate that for my kids.

Tim Ludwig: Yeah, I mean, I think that last statement there is a testament to how impactful it was for you, that you actually wanted to relocate your whole family so that your kids could have the same experience. With being pulled along or sort of swept into that current, was the pressure that you felt, was it internal or was there a lot of peer pressure?

August Felker: Yeah, that’s a good question. I think for me, it was peer pressure. I felt like I had to sort of keep up, and I felt like I wanted to be able to participate in classes, I wanted to be able to play on the sports teams. And it was a healthy amount of- I wouldn’t say it was like unhealthy stress or pressure. They seem like they do a good job of kind of balancing that at Burroughs. It wasn’t just a grinder. Although we all worked really, really hard. But I really felt like they were able to get students there that are, again, very motivated and driven. And all the teachers are that way too. And so, there was no way, there was no way that they were the teachers, and they were going to let me fall through the cracks. I think I would’ve, but they didn’t let me. And many times I had advisors kind of pull me aside and give me motivation. They’d have these, if you weren’t performing in school, they had these things called blue slips that you had to get your parents to sign when you weren’t doing well. I hated that, bringing those home. I dreaded it. So, I mean, it was a healthy thing. I really had to avoid the blue slips. I really had to get those good grades and do well in school and be a good person. They have some really unique features of the culture there. One is every morning, the entire student body gets together and they have an assembly in one room. And all the students come up and give announcements, and the headmaster lets you say anything in assembly. So, it’s really pretty neat. You feel like the students are kind of running the show. And then at lunch, you’re assigned a seat at a big family table, and literally they pass around the food like family style, and there’s a teacher at each table. And it forces you to intermingle with everybody. You can’t just sit where you want to sit with your buddies. And also, you kind of engage with the teacher at lunch. And many people who went to Burroughs say lunch was their favorite part of school. So, it really helped build those bonds, and it was a very, very unique and special place.

Tim Ludwig: It’s interesting to me that it sounds like you were maybe not highly self-motivated then, but through external pressure and a desire, probably like a lot of teenagers, to fit in with your peers, that was an impetus for you to work really hard. A culture like that that’s really strong, I think, attracts a certain type of person and obviously creates an environment where they can thrive and be successful. But it also repels other people. And so, I’m curious if you saw that ever, with somebody that like the organism rejected them, or just what would make a poor fit in an environment like that for somebody?

August Felker: Yeah, that’s a good question. I think once you go through the process and get into the school, most of the 100 people that got in, I think probably 97 graduated. So most people went all the way through. I think Burroughs had a mindset like, hey, we’re going to- and they provide academic counseling and help for those people who might be falling behind. There were several people that said, oh, this just isn’t for me. And I think that’s why they have that, it’s a unique school where they have seventh and eighth grade to kind of try to figure it out before high school. And so there definitely was some people after those first years say, hey, this isn’t for me. And then there were some new people who came and said, hey, I kind of want that, and would join in ninth grade. So, I think that was sort of the natural time to figure it out, is seventh and eighth grade before you really get into high school where it really matters for grades and college.

Tim Ludwig: And Burroughs wasn’t just an academically driven institution, right? Its athletics was also a big part of it and you were a tennis player.

August Felker: Yep, yep, yep. That was a huge part. So, I played tennis all through high school and was really lucky to have some great coaches. I sort of fell in love with tennis as a kid, and around like eighth or ninth grade, I was like this is going to be my sport and went all in on it. And tennis is a very individual sport, and it’s a grinder. You have to travel to these tournaments, and I was going all throughout the Midwest in the summer, and it’s just you. You’re not on a team, and you’re having to go and do all this stuff. So, I felt kind of by yourself. So, when I got to Burroughs, you join like the Burroughs tennis team and that was just a riot. So, for the first time in tennis, I was like on a team and we were all, we were pretty good, and we had a really great coach, and I loved it. And so I really had to sort of balance school and sports, but that was really another formative part for me in high school was getting on the Burroughs tennis team. And we were sort of like, kind of quasi a bunch of nerds. We had never won like a state championship, but we all decided as a bunch of ninth graders, when we got in, we’re going to win this thing. So that was our mission for ninth, tenth, and eleventh trying to win. We finally did it our senior year, and it was just a huge achievement. And it was probably the best, one of the best athletic experiences of my life was winning that thing.

Tim Ludwig: What were the parts individually and as a team that you all committed to that you think made the difference? I mean, four years is a long time to sustain and keep your eye on the ball for a goal like that. What enabled you personally and with your team members to stay that focused for that long?

August Felker: I mean, we really- so what helped was there’s a rival school here in St. Louis, and they won every single year, and it just drove us crazy. And we had figured out in ninth grade when we knew we had enough- we figured out it was going to be tougher in ninth grade, tenth grade was going to be tough, eleventh grade, but twelfth grade was going to be our year because we knew we’d have some younger people coming on the team, and we knew our rival was graduating some people. So, we had it all planned out, and we really wanted to be the first and we really wanted to beat the school, and it was a huge driver. We also were really lucky. One of the very best at the time, the very best tennis player in all of St. Louis was also our coach. He kind of started right, the coach, right around the same time we joined the team. So, he was highly motivated. He was a highly motivated kind of guy. So, we were all in it and we were all pumped to say, hey, you know what, let’s do this. And he was just an exceptional coach, and it was a really fun ride.

Tim Ludwig: That’s really neat. One of the themes that I take away from all of this, I mean, you run an insurance brokerage. It’s not like the sexiest industry. People aren’t out there like high-fiving and there’s not a lot of excitement around what you do. And I think even in talking to you, your demeanor is just very even keeled and steady. And so, it’s interesting this whole- your whole journey is really interesting to me because there’s like this fierce determination that lives just under the surface here. I mean, like setting your eyes in ninth grade on winning a state championship, going to the elite academic school where you’re not innately gifted and talented to the extent that some of your peers are, so you have to work really hard to keep up. I mean, it’s sort of embedded into almost everything that we’re going to talk about, I think, that you’re- and even some of the words you’ve used now, like you had to be a driver, and there’s this grittiness to your story that would not be, I think, immediately apparent to people that get to know you, at least superficially.

August Felker: Yeah. I just got so excited by thinking about those things and dreaming. And I know it sounds sort of silly, dreaming about a tennis win, there’s bigger things in life, but I can just remember as a kid just getting so pumped about it. I could envision it, and I could see it, and that really helped me, that really got me all charged up.

Tim Ludwig: Yeah, for me, my dream starting in high school was to work for McKinsey and Company. And I worked really, really hard for a number of years to put myself in a position to even get an interview because I was at a non-target school. And ultimately, we didn’t have- I didn’t have the state championship winning finale to that story. But all of the other elements were still really impactful to me. And just having the focus and maintaining it and working towards something that was really deeply personal and meaningful to me. And I don’t know where that came from in me. I don’t know why I latched on to something like that. And it certainly in many ways is out of character, but there’s a lot of power in goal setting.

August Felker: Yeah, 100%.

Tim Ludwig: One of the other parts of tennis that I want to talk about, because you’ve been lucky, I think, to have a few meaningful mentors in your life, and I might pronounce the names wrong, feel free to correct me, but Toby Clark and Hobie Holbach were two people that were really instrumental, I think, in your childhood. So I’d love to hear more about them and how you got to know them and what that relationship was like and how it evolved for you.

August Felker: Yeah, they changed my path and got me to another level in tennis. And Toby was the coach I was mentioning that helped us at Burroughs. And Hobie didn’t work at Burroughs, but I worked with him a lot outside of Burroughs to get better at tennis. So, in tennis, one of the challenges is you don’t have line judges or referees at all when you go to a tournament. And so oftentimes, one of the ugly parts about junior tennis is there’s a lot of cheating in terms of line calls and it gets kind of ugly. And you call your own lines. So, during a big point, sometimes people would make a bad call or it was- it just got very, it could get and often did when we played juniors, it became very heated. And Toby, as a coach, was the highest, most purest, high-integrity person I’d ever met. And he established we were going to be the most honest, high-integrity team ever in tennis. And we all were, but I mean, he took it to a level that- so, for example, I was in a big match and I hit a ball and my opponent called it in, but I knew it was like really out. And I won the match. And he just missed the call, and if he would have called it properly, he would have won the point. And so technically you’re not supposed to call the other person’s lines in those situations. I just as a ninth grader, just walked off the court, and I was telling people after, and Toby heard me talking about it, he goes, you go back out there, you tell them redo the point, you tell them that you lost that point. It was just incredible. It set a bar and a standard that I hope to reach every day professionally. Tennis is one of those sports where there’s a lot of gray area on that stuff, and so having a coach like that was huge, and just a great, wonderful human being. And Hobie was very similar to Toby, but he really helped. Every time I wasn’t working hard or something, he said, I thought you wanted to be a- he would ask sort of sarcastically, didn’t you say you wanted to be a state champion, like didn’t you say that a couple months ago? I’m just wondering, because you’re five minutes late. And I needed that, and I love that. I hated it, but I loved it. And so, one of the things I was thinking about is I hope I’m as good as- I hope I pass on lessons like that, like they did to me, that I do to people that work with me or are in my life or my kids, because it’s rare to find a great coach. And I think about them, and I think about how hard they worked for me – always on time, always there, giving it their all, 110%, never- and it really makes me think, making sure that I’m hopefully that great. It’s going to be hard to do it, but I try to.

Tim Ludwig: It is really hard. I think in one of our prior conversations we were talking about being present, just mentally and physically. And I think part of being a coach is really being attentive to the people that you’re coaching and that requires tremendous presence. And they feel that. And as our lives get busier and busier, maintaining that level of presence is really, really hard.

August Felker: Yes, yes. And like you say, you’re sometimes at work, I’m talking to someone, and I can see myself thinking about something else. And it’s so hard to bring it back, be present. And they were that way. And they both had families and they could have had so many things they were worried about doing, but they really helped. And they got me to another level, and both as a person and as a player. And I guess the older you get, I don’t know if I totally appreciated them, but the older you get, the more you appreciate that stuff.

Tim Ludwig: The next chapter of your life I want to talk about, so high school was successful, mission accomplished, you got into a good college, and I don’t want to spend a lot of time talking about that, but what I do want to talk about that happened during college is your experience as a camp counselor.

August Felker: It was common at my school where people during the summer would do internships somewhere and there was some peer pressure on where you’re going to go internship and what are you going to do. And I don’t know if I was like lazy or I don’t know, but I didn’t- I didn’t have that figured out. So, I was looking for jobs and I found this job in Maine where they were looking for just a summer camp counselor. And I wrote them an email and I said I’d like to apply for the job. This is after freshman year. And I drove up to this camp in the middle of Maine, and I was wearing like a nice button-down shirt tucked in. And I arrived, and they said, well, you got the job, I mean, you’re wearing a collared shirt.

Tim Ludwig: You have shoes on, you’re hired.

August Felker: You’re just- you got it, done. So I was just lucked into that totally. And it just happened to be this camp called Camp Kieve. It is a renowned summer camp in Maine that just has a reputation for – it’s a boys camp – it has a reputation for being, it’s been around since like the 1900s, and it just has an incredible reputation as being just a wonderful place. And much sort of in a different way, but sort of like a Burroughs, it’s just a really special kind of place. And I totally lucked into it. And it’s also a camp where you show up and you kind of- the kids are on campus for a couple weeks, and then you go for two or three weeks for a trip out in the middle of Maine, so it’s like a tripping camp. And that’s the beauty of the place, is doing that. So, I was hired in as a counselor to lead these trips in the Maine woods, and I was not like an outdoor expert. So, it was really interesting. But I loved it. And it was, you’d have like 12 kids in your cabin, and you’re out in the woods of Maine, whether you’re hiking or canoeing, and your job is to kind of organize and lead and motivate and coordinate these trips. It was just an incredible experience. And I really was so lucky and glad I did that as opposed to doing something in an office. And I was so glad that I got outside, and I ended up doing that every summer in college.

Tim Ludwig: How old were the campers?

August Felker: A range of age. So, you’d have some first time campers that the trips wouldn’t be like two weeks, they’d be like four nights or something. And then you all the way up to high school where it’d be like a three or four week pretty serious outdoor trip. But I just had the best time. It completely opened my eyes to a whole new world. I walked in there, I didn’t know a soul. I walked out senior year, my last time I did that, and some of these people were just lifelong friends. Another feature of the camp is you have a lot of fun. I laughed every day. And I wasn’t like a laughing type at that time. I was very serious and worried about school or tennis or something. And I just really relaxed. And I had a lot of fun. And just, it was so wonderful. And I think about how much fun I had those summers. It was just pure fun. And I think about at work nowadays, I want to make sure we’re having fun like that. Now it’s hard to do; again, you mentioned we’re in the insurance business. But I really want to make sure we have a culture where people are laughing and having fun and just enjoying it. And so that was just a really lucky break for me that I got, I wore that collared shirt and I got that job.

Tim Ludwig: This is a little wonky from like my business nerd side of my brain, but what was your leadership and management approach like at that age and with kids of that age?

August Felker: I think it was- so before you go on these trips, your job was to pack all the food, organize everything. And so, what I did was I leaned heavily on the counselors that had done it before. And I would sit down with them and say, we’re going on this trip. Here’s the map. I wanted to know like, where do I stop? Where do we set up tents? What do we eat? What did you learn? What were your surprises? What are the best secrets about this particular trip? And I took a lot of notes and grilled the counselors who had done it before. And that helped a ton. And so that was sort of my- I was just trying to figure it out. There are a lot, all kinds of rules about camping, like leave no trace. I didn’t know any of that stuff. I had to learn all of that. And I think, I’m pretty sure there’s stuff still out in the woods I left out there. But I think I was just trying to learn as much as I can.

Tim Ludwig: How did you wrangle 12 kids? I mean, probably three want to go off into the woods and do their own thing, two are obstinate and angry at their parents and taking it out on you, one has to go to the bathroom at the most inopportune time. Like how do you-?

August Felker: It was really hard. And then there’s kids that are like homesick and crying, and then there’s kids- and the camp had a program where they brought underprivileged inner-city kids or something into the camp too. So we had a complete range of types of campers.

Tim Ludwig: Yeah, so that’s a complex environment. Like how did you do as a leader of a group like that?

August Felker: It was really- I think we did- I think I tried to just muddle through. We really- I think there was like a good sort of set up on how to do the trips. And I think, so another thing the camp did really well is you show up there and they give you this big basket and all the kids have to dump their electronics, their candy, there’s nothing like that. And so that really helped that they were sort of all on an even playing field out in the woods. And the goal for me was to try to get them to work together to develop. And you kind of set up these little problems during the day like, okay, how are we going to get from this lake to this lake? You appoint a captain. Maybe you try this. How are you going to figure out this? And then they’d come up with ideas and argue and debate. That was really how we did it. And I think at the end, the goal was for the kids to come out and think, wow, I really developed some leadership skills, I learned how to collaborate with other campers. And it was wild. But a great experience just because of the dynamic that you point out.

Tim Ludwig: I had a really influential job starting in high school, and then I worked there during breaks all through college. I was a fishmonger, worked at a local seafood market in my hometown. And it was exceptional. Reading through some of your notes about your camp experience and talking to you about it, there were a lot of similarities and things that echoed for me. There was a standard of excellence that was expected, but the support and training behind it to make sure that it was achievable for people coming in. It was a craft. It wasn’t just a job. How do you become the most excellent fishmonger possible? You learn all about the types of fish, where they’re coming from, how to identify freshness, the different ways that different cultures might prepare that fish. Please take home as much fish as you want every night so that you can prepare these dishes on your own so that when customers come in, you can talk about your own experiences in preparing those. Special requests, it was almost sort of the Nordstrom approach. If you want this done, it doesn’t matter how tedious it is, we will do it, no extra charge. Bones removed, filleted, skin off, you want it cut into hearts, whatever, we will do it. And intensely hard work, on your feet 8 to 12 hours a day. It’s smelly. The temperatures are going up and down. Customers are complaining. It’s busy. But there was this esprit de corps and this camaraderie among the people that had that shared intense experience that was magical. And same thing, like there are all these inside jokes and just the special jargon. And it was hard but it was fun. Man, it was fun. And I’ve been chasing that feeling as a part of a team ever since. Like it just has taught me how hard it is to create something like that. And I don’t know if any of what I’m saying resonates with that camp experience, but like that’s amazing. I wonder like how do you manufacture something like that, like how do you create that environment?

August Felker: I think it’s hard. I think that one of the things that that Kieve was lucky and you got to mention is they have like traditions and some of them are just strange, but they’ve been going on for so long you just kind of follow them and they really are like the spine of the culture. This is our tradition. This is how we do it. And everyone sort of buys in. But a hundred percent. And I had so much fun that summer. I was so committed all those summers. And I loved it. And everyone who worked there felt lucky to work there. Everyone loves it. And you talk to anyone who went there, they just love it. They rave about it. And you’re right. I chase that all the time. And I think about how much fun we had. And like I said, I think it’s so important to kind of create that, a fun place where your can not take yourself too seriously. Part of the goal is you got all these kids you’re working with, you got to make them laugh. They’ve got to have fun. You’ve got to tell jokes and they’ve got to be goofy and silly, and you’ve got to have some of that. And so I think about that all the time.

Tim Ludwig: I love it. Burroughs, talking about traditions, you mentioned traditions there, like the open forum where the students have a voice or the teacher sitting down at lunch and the family style meals. I mean, that place seems like it was just steeped in tradition.

August Felker: It is. It really was. 100%.

Tim Ludwig: One of the other things in listening to you just now, when I asked about your leadership and management style with these campers, you talked about all of the work you did to understand how other people had done it before you. And we’re about to switch topics and start to talk more about your entrepreneurship. And I think there’s an image of entrepreneurs as sort of these aggressive risk takers and maverick renegade decision makers that shoot from the hip. And the way that you’ve approached things, including that experience, sounds almost polar opposite of that, where it’s very methodical – I want to prepare as much as I can, I want to learn from those that came before me, I’m trying to eliminate as much risk as I can. And I think for some people that might be surprising, that with that kind of an approach, that not only did you end up as an entrepreneur, you’ve been a successful entrepreneur.

August Felker: Yeah, that’s interesting you say that. I think that some people have said, boy, that’s really risky being an entrepreneur. And many times, I think, well, it’s more risky not to be. And I think as an entrepreneur, you have total control. And maybe that’s something of why it really fits well with me. And before I decided to do a search fund and while I was going through that process, there was so much thought, internal thought, and planning and all this stuff. And not all the plans end up working out. You get in, oh man, that went sideways. I’ve got to go this way now. But I certainly have always been cautious a little bit on thinking ahead and planning and visualizing what it’s going to look like before I do it. And it’s the opposite of shooting from the hip. That’s for sure.

Tim Ludwig: So, talk a little bit after college. You moved to San Francisco where you didn’t know anybody. It was a real clean break for you. And unlike a lot of people probably in that area, you didn’t go and join a tech company. You went and joined another large business. And maybe I’d like to hear about the transition from that to this small search fund-backed business in a new industry. It seems like it was a period where there was a lot of stuff that you were figuring out professionally.

August Felker: Yeah, yeah. So, when I graduated college- as a kid, my parents took us on a trip to San Francisco, and I did Alcatraz and I thought that was like the coolest thing ever, the Golden Gate Bridge. Never seen a prettier city, and I was like I want to go live there. And so, I moved out there totally solo. A lot of my friends stayed sort of on the East Coast. I didn’t know anybody out there. I didn’t even know my roommate; I was sort of connected with some random guy that was a friend of a friend. I got a job at a big company in the financial district in insurance in San Fran. And the minute I got in there, I was like, I don’t know if I can do this. It was a very big company. It was like 500 people in my office. And I just remember thinking, I don’t know if this is it. And so, I was sort of struggling with that, and I wasn’t excited like I was at Kieve. I wasn’t fired up. And so, coming off Kieve to that, I’m like, oh my gosh, I got to figure out something. So, I got linked up from random friends of friends to a couple of folks who had, and this is like 2005 time frame, a couple of people who had just purchased a business in South San Francisco in the warehouse area, far from the ivory tower of the city, and they bought a little logistics business. And they were two, business partners from Stanford, and they’d used this model that I’d never heard of called the search fund. And they’re like, we’re looking to- the job and the email as it was sent to me, it’s like, we’re looking for a salesperson, our first salesperson. Come help us sell, it was logistics. And so, I went down there, I borrowed someone’s car, I went down there. And I met these guys. 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. And I also was really intrigued about learning how to do sales because it was a pure sales role. And I was kind of in an analyst job in San Francisco.

Tim Ludwig: Before you start talking about the sales stuff, I just want to sort of put a pin in that moment because I think that decision right there to say these are the guys, I want to work for them, is probably one of those forks in the road in your life. Because staying at Marsh, big established institution, nobody’s going to look down at you and say that’s a bad choice. And without knowing what’s going on inside your head and your heart, they’d think that you were on the right path towards this very successful mainstream life. And now all of a sudden, you’re borrowing a car to go to South San Francisco. These two guys have bought this, probably if it’s like all the other companies I’ve seen of that size, it’s this ugly little company in like a run-down industrial park. And you’re saying I’m going to leave all the good stuff, drive out of the city, and I’m going to bet the next stage of my career on these two guys.

August Felker: That was it, and that was my big break, honestly. And I just knew when I sat down with them, they were so fun. I think they reminded me of people I worked with at Kieve. They just were fun, great guys, and excited. They were ready to build this business. And they’re like, we need your help. I’m like, I’m in. And so, you’re 100% right, total fork in the road, and just it was a sense, it was a gut feeling.

Tim Ludwig: That’s what it was, so you hadn’t spent a whole lot of time with them, there was just-

August Felker: No, I just knew. I just knew.

Tim Ludwig: Just chemistry.

August Felker: It was, it was. It was a total gut feeling.

Tim Ludwig: Why do you think they chose you?

August Felker: I don’t know. I mean, I bet they were like- I don’t know how many candidates they had for the job.

Tim Ludwig: He’s got a pulse, all right.

August Felker: That’s probably realistic. I think that’s it. I think they- I don’t know. I don’t know, I should ask them that. But they were- I got really, really fortunate. It was just total gut, now that you think about it, it’s interesting to think about how lucky that was.

Tim Ludwig: And you tell this wonderful story about your evolution as a salesperson that I think is filled with lots of lessons, both sort of meta but also very tactical. And so, I’m hoping you can sort of recount that journey for me today as well.

August Felker: Yeah, so, my dad had given me advice and he said, you should really try sales. It’ll be a skill that you could use your whole career. And I was like, all right, well, I’ll do it. And so that was my job, to be sales. And my job was to get people to ship stuff with us. We were a shipping company. And I had to find clients. I didn’t have like a lead list. I had nothing. And they’re like, you need to cold call people in the Bay Area and tell them that we can do their shipping. And go to it.

Tim Ludwig: That was the instruction. Good luck.

August Felker: Here’s a general elevator pitch, general. And just go do it. And at this time, I was kind of dating my soon to be wife, and I took a pay cut to do this job. And a big part of my pay was commission. And I was thinking, I’ve got to make this happen. I want to get married. This is like a serious part of my life. It’s like now it’s getting serious. I’ve got to really make something of this. And so, what I did was I started just cold calling and it was demoralizing. I mean, I got hung up on. I would do terrible on calls. Everything, I just could not figure it out. And there was another person, there was one other person who was hired at the same time with me, and he was sitting right next to me, and he’s having success. And I’m like dying. I’m like how could this be possible? And so I was working extremely hard, and I just could not get traction and could not get success. And so, I started going around and I started asking people who were successful in sales, how do you do it? What do I need to do? And one piece of advice a gentleman gave me, he said, every day, you can’t judge it on whether you’re successful on did you get the sale or not. It’s like, did you do the activities you’re supposed to do? Like, focus on the inputs, not what you’re going to get out of it. So I really took that to heart, and I got really excited if every day I could make a certain number of cold calls, and I didn’t care whether they were awful or not. And I learned that one no is one no closer to a yes, and I totally had that attitude. And I was positive and upbeat on the phone. I wasn’t- part of it in calling people is you need to be- you can’t be down in the dumps. You can’t be expecting someone to say no. You’ve got to be expecting a yes because people will hear that in your voice. And so, I really took that to heart. And I remember 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.

Tim Ludwig: Not with that person, but with someone else.

August Felker: Yes, and I remember going around the office and giving high fives, someone just called me pathetic. And that sort of got me over the hump and just got me sort of on the right mindset. It ended up being that I got a couple lucky breaks where I won a couple huge really, really nice accounts all on cold calls. And it gave me so much confidence, and especially what we’ll talk about later when I was doing my search fund, like cold calling is not a big deal. And I think I learned that. And I learned being okay about rejection. I learned you got to reach out, you got to pick up the phone, you got to go for it. And it really helped me when I was searching. It gave me a major leg up, because if I could do that, if I could sell this product, I could probably get a hold of a business owner and convince them to sell their business to me. So, it was a huge part. I built all these little games with myself. Like I’d say, I’ve got to make nine cold calls before 9 a.m. I had a strategy where my first two calls were always people I knew would say no, because I always messed up my first. I would like stumble, and oh, that was terrible, and I’d go that doesn’t matter because they weren’t going to say yes anyways. So, I had a ton of fun doing it and it felt so good to get those wins.

Tim Ludwig: At what point did you start to have the confidence and develop the itch to want to maybe be an entrepreneur yourself? I mean, obviously the two guys you were working for were great role models about this new model called the search fund that you’d been exposed to, and they were probably still pretty young and not that far apart in age from you, so it’s sort of a peer-like element that maybe made it feel more possible. But there’s also inner conviction and belief that you have to have.

August Felker: Yeah, I think that was it. At that moment, those two leaders of that company are just exceptional, Josh Greenberg and John Fowler, and really well-known in the search world. And they completely like brought me in to their thinking, what they were dealing with, their issues, I got to know their families, and they were like that with everybody. And I just was so pumped up, and I was like I want to do that. I want to be like that. And that was it. And I think they were so transparent. They were having fun building this business, the ups and the downs. And I felt like what I was learning in sales was going to be a great path. And I think just kind of rubbing shoulders with them every day, I was like that’s what I want to do. I knew it. I was like I want to follow them. I want to do a search fund or continue working with them or however that they decide to do, I’m going to follow them and follow in their footsteps. And sales is kind of entrepreneurial too, so you start having success and it becomes like really, you kind of crave that. You kind of crave that competition, you kind of crave the competitiveness, the independence, the ability to, in sales you can do as well as you want. I love that. Some people are like, oh, because I don’t know how you do a job where you don’t know what you’re going to make every day. Well, how do you do a job where you know what you’re going to make every day? So I think that kind of attitude got me really, really intrigued about being an entrepreneur.

Tim Ludwig: And they were champions of your first search effort. So did you go to them and say, I’m thinking about- that’s got to be scary. These are guys, you’re working for them and now you’re saying I want to go and do this thing, I want to leave you. And there’s a lot of grace in there somewhere where they said, we’re supportive of this, not only are we supportive, we’re going to help you.

August Felker: Yeah. So, kind of the timing worked out where they ended up selling that business. And so, they were sort of winding down their period with that company. And they were leaving and exiting out. And I was really like thinking, okay, what’s next for me? And we talked, and I talked with them, and I go, let’s do a search fund. And I really had conviction around insurance, which was the industry I had been in before. I said, guys, I’d love to go try to buy an insurance agency, and I think they sort of felt the same way too, and they said, we’ll support you. We’ll help you do it, it’ll be like a three-person search kind of thing, where it was those two as sort of the working, raising the money, I didn’t know how to do all that stuff, and helping me with the deal, and being on my board, and my job was to go out and run and be there day to day in the company that we bought. And that really was how that went, and again, just a huge break. And I think they felt like we worked so closely together, I think they had a lot of trust. They put a lot on the line for me helping me raise money because they went to all their investors and said, hey, trust August, do this, and put their name on the line for me. And it was huge. And this was like 2008, 2009, right in the financial crisis, right where it was tough to raise money to do a search fund. And there weren’t a ton of them. There were a lot then, but not like today. Everyone kind of knew each other. And so, it was a challenging time to raise money. And they were sort of right there, planted the flag and said we’re going to do this. And August is our guy. We’ll help him do it.

Tim Ludwig: I’ll share also that this was not a straight up the middle search fund given the sort of mentorship dynamic that was a part of it. And they were known quantities to the investor group. You were not. The traditional, it’s obviously changed a lot over the years, but having an MBA from a top program was also almost a requirement. You didn’t have that. Like, they really stuck their necks out for you.

August Felker: They did. They really did. And it was, yeah, and I got to search, we all got an office together, so I was searching with them in the office. It was fun for us, because after that, their business wound down, we were kind of all back together, working together, and that was so fun. But yes, 100%.

Tim Ludwig: And ultimately it was successful. You bought an insurance agency in the Midwest, ran that for a few years, had a good outcome, but not like life changing, it’s not something you’re going to read about in the newspaper. And so, I want to hear maybe when you got married along this path because I think having the support of a spouse that you’re dragging all over the country and doing these wild entrepreneurial things is worth at least a note in this conversation. And then maybe what your takeaways were coming out of that experience.

August Felker: Yeah, so I did a search and we were just focused on buying an insurance business which had the classic kind of recurring revenue profile and sleepy service type business. And my wife was just an incredible supporter. While I was doing all this crazy entrepreneurial stuff in South San Francisco, first of all, she agreed to marry me, which is just amazing. And then she’s like, yeah, I’ll support you on your search fund, like go for it. And I had met her in my last period at Marsh when I was sort of leaving, and she was like a rising star at Marsh. I mean, she was really- she had a career, she was doing the insurance for Apple Computer, and she was just a star. And so, she was just amazing to say, hey, go for it. I don’t know how she- I remember telling her dad, my father-in-law what I was doing. He looked at me like, Mary, I hope you made the right decision on this one. And so anyways, it was great. So, we had to say, when we signed up to do the search, that if I found a deal, no matter where it was, I was going to go, I was going to move. And we had to uproot. She had to leave her job. Working remote was not really a thing. There probably wasn’t like an office where we were going to be that she could work at. So, we picked out like 10 cities and I really focused on those 10 cities. Randomly, the business I ended up buying was in Madison, which wasn’t on the 10 cities list, but she was very excited about it and so was I. And I think one of the big stories for us was she was just so supportive, so consistent, so steady. Every day you come home from a search, either you’re really happy or you’re almost depressed, and you’re like, why do I care? And it’s like, it can happen multiple times in a day. You think you’re going to be moving to Dallas. No, you’re moving to- it’s a wild experience. I tried to sort of compartmentalize it, but it’s really hard when you come home not to like talk about, oh, I got this great lead, it’s in this city, and I could see her going to look on real estate, schools, and like already start to think about it. So, her journey was so hard to go through all that, and I had a deal, this deal I ended up buying in Madison, and I really fell apart one day. And I told her, I came home, I think this is off. And she was so bummed. I could see it in her face because she’d already sort of started thinking about it. I thought to myself, well, I’ve got to figure out how to make this deal happen. And so long as it’s still a good deal, I’m going to make it happen. And so, we ended up buying the business. And a lot of it was because I really wanted to land in a place that we were going to be really happy together in and a town that was going to be great. So I totally married up, Tim. And she’s been a huge supporter and seeing the plan and been along for the ride.

Tim Ludwig: That’s great. That’s a huge- I think they’re the unsung heroes of these entrepreneurial journeys oftentimes, the spouses and significant others, and without their support, it feels like it would be impossible.

August Felker: I know, I know. And many times, in some of the most important meetings or dinners, I would bring Mary to meet the seller or something, and oh, with Mary, Mary’s- we’ll do the deal. Mary’s, Mary’s, we love Mary.

Tim Ludwig: The closer, right.

August Felker: I know. And she’s just great.

Tim Ludwig: So what were your takeaways after you sold that business?

August Felker: I sold, and we sold to a private equity backed roll up. Insurance became, while I was operating this business, became very popular as an industry or type of business to buy by private equity. We did a process and we sold to a company that was a very large insurance brokerage, huge. I felt very excited to sell, but then I felt really sorry for myself and depressed because I was working. And I was like, I really, for some reason, struggled in those bigger companies. And that was a major learning for me. And it was a great company, I just don’t think it was for me. And so, I started thinking I still have got all this energy, I love insurance. I really do love insurance. I know that’s hard to say. I love the business. I have a lot of conviction around the business. I think you can really- so I thought to myself, I really want to go do this again. And that sort of led to my next thing.

Tim Ludwig: What did Mary think?

August Felker: At first, she was like, I don’t know. I mean, really? Like, we’re going to quit? We had a couple kids. We’re going to be entrepreneurs again? I thought we were done with that. And then so I was really high on it, she was kind of low, and then as I got closer and closer to buying the second deal and moving to St. Louis, and jumping off a cliff basically, making no money and starting over again, I got really low and then she got really high. She says, you can do this. And again, it was like the perfect, perfect is what I needed. But I don’t think I was- the first business, there were so many hardships as a leader. I struggled with the seller. The seller stayed on for three years. I struggled with him. 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 think I came in feeling like I knew it all and I gave off that kind of a vibe, or at least I should know it all. And I was 29 when I stepped into that role, and I just learned so much by going through that first deal and those experiences, and it was many moments, very humbling. And it was huge. And again, I had these two guys, John and Josh, who were on my board, like every day teaching me, helping me learn, talk about things, and trivial stuff. Not like fancy board stuff. It’s like, oh, how did this person handle that conversation? That was what we were discussing all the time. And so, I learned a lot and I did a lot of reflection on it and I really felt like the sale was good, but I felt like it interrupted a great learning experience for me, and I wanted to keep that going. And I think John and Josh have always told me that you become such a better CEO the second 10 years than the first 10 years. It’s like unbelievable. So why would you stop? You just keep getting better and better. And I think that’s true. And so, that was part of it, like I think I can- all the stuff I learned, all the stuff I didn’t do well, I’d love to try it again. And this time I’m going to do it as self-funded. I’m going to try to do it on my own because I’ve learned so much. And so that was a huge experience. And we love living in Wisconsin, too. Madison is such a great town.

Tim Ludwig: Yeah. And so that’s a big decision. You’re going to relocate. And then I don’t know if it was luck or design or both, but then you ended up finding this much smaller insurance agency in your hometown.

August Felker: Yes. Insurance, so I really wanted to be in St. Louis, and so there weren’t a lot of insurance targets there to buy, and so I had like 20. And the one that we ended up buying was tiny, like five people. I think it was like-

Tim Ludwig: Was there a plan B? Like if you had 20 targets on your list and wanted to be back in St. Louis-?

August Felker: That was it. That was it. And I was back to the sales mode. I was cold calling every day and working. And it was tiny, $200,000 in EBITDA, very small business, but I felt like it’d be better than starting from scratch. At least if you had something that had some foundation, some of the licensing, some of the stuff that the first couple years, if I could skip that stage of a startup, kind of jump in maybe in year three or something, and that’s kind of what we ended up doing.

Tim Ludwig: That’s amazing. And the family’s relocated and some of your kids are at Burroughs now?

August Felker: Yeah. We left a great life in Wisconsin, back to St. Louis, and it was very different for me being a leader of a very, very, very small business with three or four people. It’s different than being a bigger, I think we had like 100 people or something at the time when I left between a couple offices at the Murphy, the old Murphy thing. And so I felt like- my Wisconsin business, so I felt like it was totally different. It was harder, plugging in ethernet cables, like everything that you- every little thing. And it was really, really difficult. I didn’t know how hard it was going to be. I underestimated that those first few years.

Tim Ludwig: One of the things that you wrote about that you said you were most proud of besides convincing your wife to marry you was that you’re really proud that you stick with things and also self-identified that you failed at almost everything important that you set out to do at first, sports, sales, leadership. Where do you think that belief to keep going comes from?

August Felker: I don’t know. That’s a great question. But when I was kind of thinking about talking to you, I was reflecting on that. And I think I’ve definitely noticed that some of the bigger things that have happened that didn’t go well at first and were very difficult, and I don’t know if that was sort of maybe sports, going through the tennis thing, and you’ll lose a set. I mean, you’ve got two more, you’ve got to keep going. Or it was school early on. Or probably I just had no other choice. And yeah, I think I’ve learned that. And now I’m a little bit more, after I screw something up, like okay, I’m like, I’ll get it right the next time. And that’s a little more comforting now that I’m a little older than it was when I was younger.

Tim Ludwig: Yeah, I think you build that muscle to have that resilience and you know that if you keep trying, you have the capacity to be successful.

August Felker: Yes, yes, 100%.

Tim Ludwig: Just a couple more things I want to talk about. One, this is a total non sequitur, but the last time we chatted, we talked about meditation. And I’m just curious how your meditation practice is going.

August Felker: Yes, great. So, when we were talking last, for the benefit of everybody, one of the things we were chatting about was I never had anxiety until I bought my first business. I never had it in my life. And it was something I had to learn how to deal with. And it was very difficult navigating that. And it was a physical, horrible feeling that I couldn’t sleep and worried about things at the business. And I don’t know why it showed up then in my life, but it showed up then, and I think I’ve learned that it’s going to be with me forever now, which is fine. And sometimes being a little anxious is good because you stay sharp. It’s like that paranoid, only the paranoid survive a little bit. But one of the things that I’ve wanted to try to do is like some way to sort of go into a day feeling more even keeled and less anxious. And I’ve been trying this meditation, and I think it’s- I’m like 20 days in of the 30 day thing that you recommended. It’s been great. More than anything, it just helps give you focus and clarity and just breathing and taking deep breaths. So, I think I’m optimistic, Tim. I’m optimistic. I’ve never done it before. I’m definitely optimistic.

Tim Ludwig: I remember, and I’ve fallen off the habit a bit more than I’d like to, but I remember when I was first starting out, it felt like a leap of faith to start doing it because the changes are so gradual that most of the time, they’re imperceptible. So, it constantly is in my head saying like, is there any benefit to this? Is this working? Am I getting help? And then there would be, after a few weeks of it, I’d have like five seconds where I was like, oh, something just happened there where I felt a little bit better. And maybe I was just making it up and attaching things that weren’t really there, but it was enough to keep me going and say, okay, the experiment is worth continuing. And the time that I’m spending on it is so minimal that I didn’t have much of an excuse not to continue forward. So, I’ll be really curious to check in with you again in another month or two if you keep with it and see what comes out of it. And then to wrap up, given everything about your life journey so far, what’s been the most surprising to you about your life?

August Felker: This is a great question. I don’t know if when I started out of college if I knew I was going to be an entrepreneur. And I really felt like that was such a hard thing. It was like this thing I never- I didn’t even know how to do or buy a business. I had some friends in private equity, but I really didn’t even know what private equity was. And I had no idea that I would end up being an entrepreneur who bought a business or two businesses. And I think the surprising thing was is it’s not as hard as you think it is. And of course, day to day is brutal. But in the long, big scheme of things, anybody can do it. If there’s a will, there’s a way. And it has been just such a fun experience, so hard, but it surprised me that I’ve sort of taken this path and that it’s been something that’s brought me so much joy. And I never thought I could do it, but I just sort of stuck with it.

Tim Ludwig: Yeah, that’s great. Well, we’ll close on that. Thanks for the time and the wonderful conversation, August.

August Felker: Yeah, thank you, Tim. Love it.

Tim Ludwig: If you enjoyed today’s episode, you can find transcripts and show notes at transitionspodcast.com. Please also feel free to share this episode on your favorite podcast player with friends and colleagues who might share an interest in exploring the most critical moments from the lives of today’s business leaders.