Devin Bostick - Founder of LuckyTruck: Validating an Idea, Raising Capital, and Replacing Yourself as CEO

Devin Bostick  00:00

I still remember the customer down in Stockbridge, Georgia hauling Vidalia onions. I remember us chatting about onion hauling for a while. And that was one of the best feelings I've ever had, just seeing that first sale in a company that I was working on where I was the CEO.

Callan Harrington  00:15

You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here. Welcome back, everyone, to a another episode of That Worked. This week I'm joined by Devin Bostick. Devin is the founder and former CEO of LuckyTruck. LuckyTruck makes commercial insurance easy for trucking companies to buy and manage commercial trucking insurance through an all in one digital platform. Devin is also an active pre-seed investor through his investment fund Paracosm Ventures and teaches entrepreneurial design at the University of Colorado, Boulder. This was a fun interview. Devin is incredibly reflective, and gives a very honest description of what it's like to be a tech founder, the good, the bad, and everything in between. We talked about the lessons he learned raising capital, how he pulled himself out of the day to day, and why he ultimately chose to replace himself as the CEO. He gave a great perspective on this. And it's a topic that I don't see talked about all that much. Now, my favorite part of our conversation was talking through how Devin validated the idea he had for LuckyTruck. He gave us the playbook on how to bring an idea to life. Having been in the startup world my entire career, people with an idea for a business often ask me what they should do to get started. I will tell you this, this is the episode that I will now point them to. How Devin turned LuckyTruck from idea to an actual company was excellent. And it's such a good way to validate that you're on the right track. So with that, let's get to the show. Devin, welcome to the show.

Devin Bostick  02:30

Thanks, Callan.

Callan Harrington  02:31

I feel we've had probably the most troubleshooting. So anyone who's ever done a podcast knows like, so you're going to lose some footage some time, and I appreciate the patience that you've had going through this.

Devin Bostick  02:45

It honestly reminds me of working on startups where you might lose a file or have to redo something. And there's a lot of learning every time you try it again. So thanks.

Callan Harrington  02:55

So true. I think we're experts at it at this point. Here's where I want to start out, I want to hear the story of when you lost a $300,000 prototype.

Devin Bostick  03:05

Oh God, that definitely caused some stress for some people, including myself. So I was at this food tech startup called In It. So picture the Jetsons, like this smart kitchen that can like plug in the recipes, tell like what food you have, and make recommendations, and then connect to like Amazon or something like that, or Whole Foods. So they had an oven that also connected to the system that they had paid some people to prototype. And we needed it for a demo. So they sent it from the- there's an office out in San Francisco, and then I was part of this New York office. We had a WeWork, but we had this demo space at this company called called Perch, where we could show exactly how the oven could cook, and it could go through forty-two cooks steps to cook a chicken, and it had different technology. Well I was tasked to take the oven out for a series of demos to different investors and other relevant people. Like Jacques Pepin, if you know Jacques Pepin, the chef, was there. Actually, Meryl Streep walked through at one point. So did Neil deGrasse Tyson, so there were a lot of famous people checking out what was going on. And I passed the oven off to the UPS guy to ship it and thought it was one and done. And I hadn't really returned a lot of items at that point and just sort of expected it to work. Well it turns out, he had a blurry image of the oven, and I didn't get the confirmation code on where it was moving. You would think that for a $300,000 oven, I would have done that. But I didn't. And my boss was Sam Kass, who was Obama's chef in the White House and really busy guy with a lot going on. And I remember there was like this office room, I'm sitting with him and the COO of the company and  the head of product experience, who built a lot of experience stuff on the prototype. And they're just looking at me, and I was just trying to tell my narrative of how I was on hold with UPS, and how I got this covered, and UPS couldn't figure it out. So I then reached out to one of the engineers out in California. He used a deblurring software. He found the predicament quite unusual, but he used a deblurring software to take the barcode and make it so that we could read it. And we ended up using that and figuring out the oven was at LaGuardia. And then I contacted UPS, and we got it back. But for a few days there, maybe a day and a half, two days, we were, especially me, I was pretty concerned with finding the oven. So it was a good experience.

Callan Harrington  05:31

(laughs) My favorite part is the engineer found this situation pretty atypical. What was this guy- one, how did you even get a response from him? Did you just look this person up on LinkedIn in order to kind of figure this out? Or how did you find this person?

Devin Bostick  05:46

The engineer?

Callan Harrington  05:47

Yeah.

Devin Bostick  05:47

He was actually internal in the team, but I didn't really know him. So picture me Slacking someone I've met maybe once and saying, hey, I need help with something, and then dropping it on him that I lost the prototype that was promoting the entire company.

Callan Harrington  06:02

Okay. Okay, okay, okay. So this was an internal guy at your company. And also, just for clarification, there's only one prototype is my guess. Is that right?

Devin Bostick  06:12

I think there was just one prototype.

Callan Harrington  06:14

Okay. So there's one prototype. It's $300,000. And that is fantastic. I love that story. So I know New York was a big part of, of your entrepreneurial journey. Tell us a little bit about that. What was that like? How did you even kind of go on this entrepreneurial journey? What led you there to begin with?

Devin Bostick  06:34

I was hungry. I moved to New York, borrowing a family minivan we had. I put all my stuff in a locker in the Lower East Side. And then I got there and just started to try to figure out my career. I'd interned in venture capital, and I grown up with an entrepreneur. So I had some adjacent information from that experience. But then in New York, my goal was to pick a few startups before starting my own company. So that typically meant I would join a startup, I joined like a food tech startup, the one that I just mentioned, then I joined an insurance tech startup, I briefly helped a few friends in their startups, or I helped this other guy on this other financial services startup for a bit. And I was going to meetups and events. And then I would go into these modes, like a few times a year, where I rapidly try to figure out an idea. And I did that probably a dozen times. Until one day I was at CoverWallet, this InsurTech small business insurance platform in New York, and saw an opportunity to tap into the trucking vertical and provide this digital insurance platform. But I would constantly go on walks throughout New York, and New York is obviously an incredible place of stimuli where you just run into a lot of different ideas. So it was just a great spot to gain exposure to different ideas that people had come up with.

Callan Harrington  07:53

Yeah, I love that. After the food tech startup with a $300,000 prototype, you went to an insurance company next. It was just the most logical move of all time. (laughs)

Devin Bostick  08:03

(laughs) I was really into poetry. So.

Callan Harrington  08:07

I love it. Why New York instead of San Francisco?

Devin Bostick  08:09

 I was already on the East Coast. And I had been in New York a few times. And I just remember the first time going there, a friend who was a little bit older, we went out, I just met a bunch of different people, and I just found the energy extremely exciting. I hadn't been to San Francisco yet. So it was less about let's go to San Francisco and test it. It was more around New York felt right. So if it ain't broke, don't fix it.

Callan Harrington  08:32

Yeah, totally. I love New York. Always been a huge fan. So you got this experience at these different startups had the itch to create your own or walking around the Lower East Side trying to come up with different ideas. And you settled on trucking insurance with LuckyTruck? Why was that? Why was that the one that really stuck with you?

Devin Bostick  08:53

When I was at CoverWallet, I really learned to appreciate that timing is a large part of building a startup. So I saw where there were companies like CoverWallet, and another one was Embroker, and there's an even older one called Insureon, and then there were some newer startups that occurred after CoverWallet. But what I realized was that insurance, when it could focus on one area, could be highly effective, especially when marketing costs could be quite high if you're trying to pull in a bunch of different verticals, depending on your strategy. So that's where I was interested in doing something with an insurance. I liked that CoverWallet was customer facing. So you could take a percentage of the insurance transaction. So there was a very obvious revenue gain. And in trucking, I was looking at some other areas. Cyber is a huge consideration, and that's obviously growing and growing and growing, and I found healthcare interesting, and especially in the rise of different robots and whatnot helping healthcare professionals. But I saw a really unique opportunity in trucking, where you have: one, a ton of truckers. There's truckers- go on any highway, there's truckers everywhere, and they're mostly small businesses, something like 97% are businesses under twenty trucks. So I saw an opportunity because I was researching different verticals and saw an opportunity where trucking could use a customer facing platform to make the transaction a lot easier. And in my research, I actually found a few books written by truckers, and also some textbooks on the history of trucking, and trucking insurance, and converted them into an audio file, and had a lot of fun just like walking around New York. I was a New York Sports Club member at the time, that they're like a mid level budget gym in New York. And I would just go there and just listen to different aspects of trucking, and the more I got into it, I became really interested in it. Then I ended up calling a few hundred truckers. A lot of their information was available online, and only a small percentage really engaged with me, but like, the more I engaged with them, the more I got really excited about the opportunity.

Callan Harrington  10:58

What were those calls like? Are you catching them when they're on the road? Or...

Devin Bostick  11:02

Yeah, they're on the road. Yeah, it's something like you're calling someone who's getting lots of calls, because so much trucking is done over the phone, like the dispatcher's calling them, all kinds of people are calling them. And so I would call them, and you get someone who would answer the phone and be like, hey, this is so and so what's going on? And I'd be like, hi, I'm Devin, and I'm currently looking into challenges, and would you mind just chatting for a minute about challenges within insurance? And people would be willing to talk to you, and you'd hear things like, I have to work with my broker, and they're just unreliable. I hate that I have to wait for things. And there I am, like frothing at the mouth, hearing terms like "wait for things" and "manual transaction." And then I just sat down and started to draw out a diagram of, well, how can we take this manual process and start to put it into a digital model. And I went online and pretended I was a trucker for some insurance brokerages, just to try to see how the current process worked. And then I went back and deconstructed it and basically started out with a basic trucking brokerage, and then built in technology and slowly automated different functions. But I purposely started with the brokerage to understand how the current market operated. And then that helped me prioritize the product roadmap.

Callan Harrington  12:16

You know what's so interesting about all of this is, I love every single thing that you just said there. You know, and I'm sure you get asked this all the time, but I get asked this quite a bit, on if I have this idea, I want to start a company, how do I go about doing this? And the first thing that I say is go do twenty customer interviews. And I didn't make this up, right, Jason Lemkin has talked about this forever, but what you just said is the absolute best and number one thing that you should do if you want to start a company. You can go get everybody else's opinions all day long, but until you hear it directly from your customers, then usually it's whatever you start out with, it ends up being something that's like a couple of degrees away from that, that you find you start to drill in on kind of what the main problem is. So I think that's great. To that point, is that typically where you'll point entrepreneurs, when they ask you that question of how do I go about starting this kind of business?

Devin Bostick  13:11

Totally. So when I joined CoverWallet, I had grown up, my dad was a very sales focused entrepreneur, and some entrepreneurs are more tech focused, and so on. And what I really learned from him was that through selling, you could really understand someone's problems, especially by active listening. But I was also horrible at selling. So I joined CoverWallet, and my goal was do that for a year or two, just to figure out how to sell products. And it was really interesting selling insurance, and you get all kinds of different requests coming in. Like at one point, I remember someone called in and they were doing like ghost hunting, they needed like an errors and omissions policy, in case they created errors, and I found that really, philosophically fascinating.

Callan Harrington  13:50

Classic. That's a classic risk of ghost hunting. (laughs)

Devin Bostick  13:53

(laughs) What I saw was like, in CoverWallet was interesting, because the platform in a lot of ways was a sales enablement and service enablement software, where a lot of transactions were a combination of both manual and automated flows for the customer, where you may help the customer over the phone on something or they may go into the platform for different requests. What I learned from that was that salespeople are not to be underestimated. A lot of salespeople have a ton of vision. They don't always know, like, some are really good at structuring it, some don't. But I found a lot of value in just chatting with salespeople. So when I was selling, and then when I started LuckyTruck, I found that by just being the salesperson in the early days, closing a few deals, I wasn't- by no means was I good at selling commercial truck insurance. I was okay at it. But it helped me learn how to frame the problem and the solution, what sound bites made sense, and also how to gather information around different pain points. Where you might be on a call, and then start to build some rapport with the customer, and then start to ask them questions about their business, and then I feel like that's when I would get insight, and then I would take that insight, and then ask other customers similar questions. And if I sensed a pattern, then try to figure out how could I take what I saw as a problem and structure it into a platform oriented solution that was adjacent to the current business offering.

Callan Harrington  15:17

And one of the things that you hit, and I'm biased, of course, right? You know, my whole career has been in sales in leading sales teams. But one thing that, you know, a key thing that I think is awesome that you picked up on is that the best salespeople operate exactly how you just mentioned. The best salespeople, one of the better quotes I've ever heard on this is, they can be a consultant in their prospects industry, they know their prospects industry so well that they can consult them on it. That is the level. That's what separates the best from everybody else. It's not the, I've got all the closing tactics and everything else, which is typically the things that are portrayed, it's that I know your business as well as you do, in my particular area, I know it better than you do. I can listen to your pains, and I can provide a different type of solution in order to help you solve it. So I think that's excellent. One of the things I'm curious about is- so you came in here, you started to- you validated the problem, you did your customer interviews, you did your secret shopping. When did you start turning this thing into revenue?

Devin Bostick  16:19

So I remember, we made our first sale on March 2nd, 2020, and we had had a false start on trying to build the platform. And that's a long story. I had never built software before. So I tried to build the platform three times before finally, really getting it going. But I remember the early revenue I saw was crucial for business survival, especially being a founder without a track record, and without really understanding how to raise capital. So I needed time to learn, and the revenue provided that cushion. But we went after revenue. We started going after revenue in the second month. And then we got our first sale a few weeks later, maybe like two and a half weeks into starting to sell. I still remember the customer down in Stockbridge, Georgia hauling Vidalia onions, I remember us chatting about onion hauling for a while. And that was one of the best feelings I've ever had, just seeing that first sale in a company that I was working on where I was the CEO.

Callan Harrington  17:16

Was it more just like I was able to do this? Was it that this person took a chance on me? Or what was it, like what led to that feeling?

Devin Bostick  17:24

It was a sense of community feeling where, as we've covered a minute ago on salespeople, you know, we felt a rapport with this person. And they liked what we were working on and decided to purchase a policy through us. And then, over the next year, as well as several other early customers, I would chat with them on a regular basis and just check in with their business and just hear them out; could be anything from fuel prices are up, or they're frustrated with their dispatcher, or I would ask them about how the insurance is going, and you get blunt feedback. And the first sales were really clunky. Ther were lots of issues, there were a lot of- especially on the service side, truckers, because their insurance and risk is so tied to their core business, that moving around, and their margins are so low, and shippers have different requirements. Truckers tend to, even the one truck companies, will switch things on their insurance on a monthly basis. So you got to be ready. It was interesting in the early days, because I sold some of these policies unanticipating the amount of service required due to like those different forces. There was an inherent messiness. I was our customer support for the first seven or eight months and was doing the transactions myself. So when it came to like our CRM, I had a lot of opinions on like, what I thought worked and what didn't. And when it came to like our call system, I had other opinions on like, how well the call system connected to the CRM, and how text was enabled, or other calling features. But it was all around like how can I support a certain level of customer experience while continuing to grow the company and not getting totally bogged down by by the requirements of service. So it was it was very interesting in that sense. And it was also really helpful in working with a few early customers who felt that sense of community feeling and wanted us to succeed because it helped them operate better.

Callan Harrington  19:18

How did you get out of that? How did you fix that? Right? So if I'm playing that back, it's you got these first couple of sales, were super excited about it, did not anticipate that how much this was, how much it was gonna cost in time and resources, to service these business and keep these customers happy. How did you solve that challenge?

Devin Bostick  19:38

It was a very tiring period, I was working nonstop, especially during business hours. It's inherently jumpy. Like you're trying to do a whole host of different tasks, like say you're trying to like edit an Excel file, or put a deck together, or do other- or put a marketing plan together, or different aspects of the business, and then all of a sudden needing to get on a call, because the trucker needs stuff right now, and you don't want to like leave him hanging. And you got to make sacrifices going both ways, which may mean that you miss a certain number of calls. But like, that's also not a good look. So like, you hear about large organizations creating like an SLA or service level agreement, and like you work with us, here's like our turnaround time. Like, it's interesting to try to uphold an SLA when it's personally guided, and you're also getting fire hosed by all the additional opportunities that come with growing any business. It was a lot of work.

Callan Harrington  20:29

Was there something in particular that changed, whether that was hiring people, whether that was prioritization, and saying no to certain things, in order to say yes to others, but was there anything that you can think of that really was the turning point for that?

Devin Bostick  20:44

The best decision I made was I hired a remote secretary. Her name is Irish. And she was absolutely phenomenal. She took a lot of work off my plate, helped me with things like do industry research or figure out aspects of the market. Like I'd have her do a whole project on fuel cards, or I'd have her basically do things that would take a while that I felt necessary for my own understanding. And by doing that, especially in the early days, she was offshore, so a lot more affordable than hiring someone onshore. She provided phenomenal work and truly helped me, during the bootstrap phase, delegate some of my tasks so that I could get a lot more done.

Callan Harrington  21:24

So I'm really curious about this. You know, sometimes I go back and forth on this, I go back and forth, where sometimes I can see it's like, oh, I've got these X amount of tasks that they can work on. But once those are done, I don't know what I'm necessarily going to have. But everybody that I talked to says do it, you will find you will find work for them to do what's your take on that.

Devin Bostick  21:45

It certainly takes practice, and like working with any teammate, and also clear definition. That's where I found as a founder, I basically had a Trello board, where the first column was vision and goals. So it helped me understand just constant reminders around here's where we're going, here's where we want to go. And that stuff can change, it can tweak, but at least I had a direction. The next column was a backlog column of stuff that was probably good to do or necessary. But it just wasn't quite ready to be structured. I then had four columns in the Trello board. I had important urgent, then I had not important urgent, and then I had important but not urgent could be something like taxes, if those aren't coming up for a while. And then in the last column, it was just not urgent. And then finally there was like a completed column. But whileI wouldn't do a lot of the not important tasks, the prioritization helped me stay on tasks that are urgent and are important, or continue to think about placing stuff that is going to be important, and assessing if it's really important right now. I saw that, and like you hear about principles like the Pareto principle and the 80-20 rule, where 20% of your tasks give you 80% of the output, and like whether or not it's that it is twenty and eighty, or fifteen and eighty-five, or something different, I really felt that when I was building LuckyTruck, where some tasks had a lot more leverage over others. So when I worked with Irish, she would help me with stuff like, especially year two and three end of the business, I'd send her things like hey, can you calculate a cohort curve, where I'd send some of the loose data before we had Looker automating certain aspects of it. So she'd helped me with like some Excel modeling or weekly metrics updates so that we could scorecard metrics. When we were doing fundraising, I'd asked her to do briefing notes on who I was meeting with, in order to build rapport with them when I first met with them or understand their bias or, or even like, say we're meeting with a fund, I'd ask her to just look up the progress of some of the investments to help me understand where I think this funds head's at. So stuff like that. And I think part of it for me, there is an inherent productivity in her help. And there's also an inherent, just overall soup of creativity, where she would take some of the research off of my plate, and I would quickly look at some of it. But by doing that, I would have more hours to decompress. And I definitely think it's challenging when you're working all the time, to continue to feel fresh and keep the fatigue down. I think if you let the fatigue get too high, then you can start to make decisions that may not be optimal. So that's where there's definitely an admittance of I'm only human, and especially now if I have like a big decision coming up, I'll try to not make the day leading up to it as busy, just so I have time to really think through it, because that decision could have influence over the next six months or years to come. And that's where having someone on the side to help was just a constant optimization around how we work together as a team and then understanding like what was in scope and what was out of scope. And then it was a great example of me in the CEO role needing to structure roles or responsibilities by person, and at times like she would also come with different ideas and say, hey, I see this, do you want me to work on it? And it may have been something that I didn't anticipate. So there was always two ways in that feedback loop.

Callan Harrington  25:05

Yeah. So it sounds like starting to get some help and being economical about, it using somebody, as you mentioned that was offshore to help with that, while you were bootstrapped. When did you decide to raise capital?

Devin Bostick  25:19

I decided to raise capital when I started the business because we had no money. And I have a lot of opinions of raising capital now. So at LuckyTruck, I really wanted to get a seed round done. As I mentioned, I'd interned at a venture fund back in 2013, so I had been on the other side of that very briefly, as on that side. Then I'd worked for an investment bank, where I was helping different private equity funds and debt funds raise money. So I saw a little bit of adjacency there as well. But I'd never really been in the room with VCs, pitching to them directly. So I think I failed on our first 150 pitches. And yeah, for those of you if you are listening, and I failed on the pitch, thanks for taking it, but I just didn't understand what I was doing. And it was really hard for me to give a consolidated vision right away. Because I hadn't practiced doing that. I would constantly try to- there's old meat factory metaphor, where it's like, show the sausage sizzling, don't show how it's made. And I kept trying to show everyone how the sausage is made, and walk them through the factory and say why we built this structure and that, and I'd lose people. They wouldn't care. They'd be like, well, you can always hire a new product manager, we want to know about intrinsic aspects of why you, why are you the person to solve this? Is this really a big market opportunity? And why is the timing so good? And those were really the three questions that, as I went through different raises, I've learned, so critical. So why now, why you, and then is it really that big of an opportunity. So we re-did the deck a bunch of times, we probably re-did the deck fifty times. And in the beginning, I tried to design, and it was horrible. And then I went on Upwork and found someone to do that for twenty-five bucks an hour. And then it was better. And then we finally had a Silicon Valley type designer take a crack at the deck and polish it up. And it also helped with the overall communications. They've done that kind of work for other fundraisers so they knew what they were getting into. But there was one of the guys that- our partners over at Sensitech once told me, you're never going to like your deck. And it's always a challenge. I really tried to love our deck at some point, but I never did. And I didn't love it because they were always investors who found different loopholes especially- there's a book Venture Deals by Brad Feld that I'm sure you know, where he breaks investors into three categories. There's the curmudgeons who like to tell you why you're wrong, or there's those types of investors. Then there's the the agreeable people who might want to be your friend, but might not invest. And then there's the technical people, the analysts, who might want to get into the weeds. But I found that it's hard to find a deck that just simply works, you have different personality types and all that. But when I started to raise capital, I realized that, and I'm telling you what the context here and that raising capital is such a social activity, where you're trying to get different stakeholders as different fiduciaries with different interests into the same company. And it really puts stresses both positive and negative on the business, it definitely puts a lot of pressure on growth, as you definitely see with the work that you do. And like going into it, I didn't really realize that, and now I realize how milestone based fundraising is and how important it is to have a narrative around the milestones that are required. And then how important it is to update people well in advance, where you're saying, here's where we're going in twelve months. And if they liked the plan, and you can show that you continue to hit different stated objectives. That's a pretty strong signal. And then the last thing I learned was in the beginning, I would try to just go out and be friends with the investor, and chat with them, and see if I could convince them this was a great idea. But one of our advisors, a guy named Alex Levin, mentioned to me like you're only raising or you're not, don't ever half raise. And it makes so much sense, especially now where you want to create a group of investors at the same time, so that you have enough leverage to optimize the economics and then the controlling terms in the term sheet that they provide. You don't want just one investor with all the leverage, who knows it, to give you a certain type of term sheet. And some investors won't necessarily throw you a full true term sheet because they know that that's going to make it harder to raise additional capital, but others won't. So that's for now, I appreciate your raising or you're not.

Callan Harrington  29:25

One of the biggest things that I see founders struggle with, especially in the early stages, is that balancing act. In the early days, you're still very much operating the business. It's highly doubtful that you have a COO until series B, C, even, where somebody's really operating the business like that. And if you're doing a lot of fundraising, you're gonna be always kind of pulled in multiple directions. I think that's great advice for sure. So once you raised capital and you really started to hit that run phase, how did things change for you? How did things change for LuckyTruck? What that look like?

Devin Bostick  30:01

So it was the first time I had a board. And the board was interesting. And every member, it was actually their first board, we'd raised money from a company called Sirius Point, that is a public company where they had, or they have a an investment arm where they'll invest in different insurance acts. And a lot of the time, they'll provide different investment by different insurance capacity, if you're like an MGA or an insurance carrier, etc. It was really interesting having a board member with that background. And then also Julie Zimmer, who's CEO now, where she had been the CEO at Embroker, and I asked her to come in as independent, to basically help me figure out how to optimize the operations for the company. It wasn't really struggling. After getting a round done, I learned so much about fundraising, I felt better there. I was decent at wooing employees inward. And I had a lot of ideas. And I love to work on the product. And I was decent at figuring out like sales flows and whatnot. But I hadn't really run a business before. So I didn't really understand all that. So when we raised the money, there was a bit of this awkward first few board meeting period, where I was learning how to put a plan together, and then offer it to the board. And that's where I really appreciate now the different fiduciaries, where you almost have this hourglass like model where the top of the hourglass is the board, which is representing the shareholders. And the bottom of the hourglass is the employees and the customers and the other side. Like at times, like I say it's an hourglass because the interest can be divergent, where the board may want to optimize certain margins like getting the marketing spend down, but revenue up, and the employees may want raises, and the customers may want faster service time. And those both obviously cost money. So that's where just understanding how to juggle that, and then positioning the structure of the company to the board to have them stress test it, was something that I definitely struggled with in the early days. And I learned a lot about it, and ended up studying the topic quite extensively in order to improve it. But I highlight that towards your question because that's where the CEO's job is to execute on a vision. And once you raise money, you did promise different forecasts to the investor. A lot of investors know that pretty much every company misses their forecasts, but you still really want to try to hit them and definitely exceed them. So that's where it was different growing the company and figuring out how to delegate activities. That's where we created a list. Julie, who I just mentioned, who came over from, she was actually heading insurance at Flexport after Embroker, now she's CEO at LuckyTruck. But she came over and took some of the Amazon style, long range planning and Amazon style framework that Flexport had adopted. And we created like a list of roles and responsibilities, we redid parts of the org chart, and then we created a few adjustments in  how we looked at KPIs, which are output based metrics, and OKRs, which are input based metrics. Like a KPI, if anyone wants context on that could be like, we want to grow revenue by this amount, whereas an OKR could be like we want to improve functionality around like the engineering team's capabilities. So it's a little bit more input based, whereas the other ones a bit more output based. But yeah, there's the answer for you.

Callan Harrington  33:13

I love it. You gave me like thirty good examples on that. So you brought in Julie to be the CEO. And you've talked about this quite a bit. And of course, you introduced Julie, and Julie's been on the podcast as well. And she's excellent. What led to that decision for you?

Devin Bostick  33:28

So when I started the business, I'd just turned twenty-six, and I felt this deep need to successfully build, grow, and exit a startup. And I saw truck insurance as the first one of several. And it was an interesting situation in that we'd raised capital in the fall, a year before Julie came. And the trucking market wasn't quite as friendly. We also had, with any startup, we had our own internal challenges. So we were growing revenue. I think we did something like we doubled it or got it to two and a half times what it was, something like that. We were still missing our projections. And I found that I was calling Julie nonstop for advice. I had met her a few years prior in New York at the insurance insights event. I basically said hey, do you mind if I call you here and there? And she said yes. So I would come with preset questions. I would call her once every two weeks, we'd have like a regular meeting. And over the years, she really got to understand the LuckyTruck. We were growing and I was trying to do a ton of different things at the same time. I also hired a few VPs and was delegating a lot of the activities that I was doing to them. You know, I was running payroll, I was doing financial modeling, I was doing parts of our product roadmap with Adam, the VP of product. I was doing like literally touching everything like all the time. Then I hired VPs and when I started the business, I didn't have any management experience. I was always a direct contributor. So like a bank or at a startup. I never I had like a team under me. So there was a lot of learning curve and figuring out how to get people into the right processes. And that's where I was really, really impressed. And Julie really mentored me on how to understand the team. And I actually asked her twice, I said, do you want to be CEO? When she finally said, yes, I then approached her board. She was on it. So there was a humor there. But I basically approached the board with a serious point and said, hey, here's an idea, what do you think? The idea was received well, and I was very happy with it. I was struggling to grow revenue based on the projection. So I felt a sense of insecurity. And I was being very hard on myself. And I saw Julie coming over as a great way to learn, and also a way to de-risk the business, as well as all the attributes that Julie's brand brings in. Being at Flexport, she had learned a ton about shipping. They have, I think, like something like 20,000, or they have a bunch of trucks that work with the Flexport platform. So it was intuitive for her as an industry leader to come over. And basically, I proactively told the board, I was going to give up some of my equity to her to keep her incentivized. It's interesting, looking at other examples, but I think equity is, you know, typically a great incentive. I really want Julie as a CEO to have enough incentive. And then after working with Julie for- really, I left in March 2023, she became CEO in in October, in the first week of October 2022. We realized pretty quickly that one, I had trouble giving up control in terms of the CEO responsibilities. And then yeah, as the founder, I was like, this is my baby, I started this thing, it's really hard for me to not play a little bit of dictator at the time and say we're doing this, it's just what we're doing, and try to in a way that's like, socially nice but firm. Julie and I were actually at a place in Chicago, working for the week, and I basically said to her, we're arguing a lot, maybe I should shift to like, advisor or something. And she agreed with the decision. It gave her a lot of room to breathe, so then I basically decided to leave the business based on that.

Callan Harrington  37:06

Which I can't imagine how tough of a decision that was internally. And you talked about it, you talked about how you felt that a lot of that was the right move to do, but it was really difficult because this was your baby. Now that you've kind of had this chance to- and we've, of course, spoken quite a bit in between the times that this has happened. You know, I look at a lot of the stuff that you kind of post on LinkedIn, and a lot of these reflections. What are some of those things that you've taken away now when you look back at that?

Devin Bostick  37:35

So I think the mind having a physical presence within in the body, say it's a combination of electricity across different nodes and neural nets. And whatever it is, it's like any other any other part of the body where if you train it, it will go through changes, or if you abuse it, it might need time to recover. And what I felt from LuckyTruck was that I needed a break to just process everything. And because it's hard when you're going all the time, like I would take vacations here and there to decompress. But like you're always thinking, at least for me, I was always thinking about aspects of the business. I didn't have a lot of discipline in just turning off and losing myself in a novel or doing something to decompress. I was I saw it as like, if I take these few years and work like crazy, I can produce like exponential results that will have lifelong positive implications. That also it took a toll and I felt very mentally tired. And I spent time- I was actually spending time working with a coach who works with different founders. And we just went through different beliefs and perceptions. We met an hour a week for three months, and just drew out: here's the circumstance like capital raising, and then how am I feeling? How am I thinking based on that? And then based on that, like, what actions do I take? And then based on those actions, what results do I take? I just spent a lot of time restructuring parts of that. Like there were definitely times at LuckyTruck where I'd be really stressed, and like, then call a friend, and have some pints, and order like a late night burrito. But it was also healthy to a degree; it wasn't entirely unhealthy. But I think that what I really learned after leaving LuckyTruck, and working with a coach who specialized in helping founders gain like a broader sense of self acceptance, happiness, and different positive attributes was the power in mental modeling, how circumstance affects one's perception, and how those beliefs are created. What I learned from the experience was how to really cut through all the labeling such as like branding around a fund, or where someone went to school, or aspects of the customer that may be biasing how I'm seeing it based on my own experiences, and to really listen a lot better, not only to myself but also to the people that I engage with. And a lot of my posts have just been thoughts around that and I realize a lot of my posts may have errors in them, where, years later I realize, wow, I don't believe that anymore. But I was posting, and I was trying to copy out different posts with, here's stuff that I'm thinking about, I find it interesting, I'm finding it meaningful in the context of building a company. So therefore, like, here's some information on what I was thinking.

Callan Harrington  40:16

You know, it's so interesting that you say exactly what you just said. One, I appreciate you sharing all that, just in general. And I can empathize with that, especially of like never being able to not think about it. It's really, really, really, really tough to disconnect. And the thing that you've mentioned, specifically, and I just wrote, coincidentally, a newsletter that went out Tuesday on this. And I talked about how, one month ago, I wrote a post on LinkedIn that said, you know, essentially, I've brought in more deals at the hotel bar than I ever had the tradeshow booth, right. And I was at InsureTech Connect, which is a big, you know, this conference. But for our listeners, it's a big conference in the InsurTech space. About one week before that, I was in ER with some stomach issues, and the doctor's like, yeah, you're not going to be able to drink. And I'm like, I've never done a conference in fifteen years of being in sales without drinking. So I had a ton of anxiety around this, like, I don't- what are people gonna think, you know, am I like- is this going to be a waste of money? Because I'm a business owner, I care about how much I spend on conferences. And then I went, so I was like, okay, I'm gonna make an experiment out of this. Went to the conference, of course, didn't drink. And I did everything the total opposite. I met with people early, I went to sleep after the dinners. And I went to the trade show floor early, when there was hardly anybody in there. Ended up being one of the most productive conferences I've ever had. And not but one month ago, I literally posted I've closed more deals at the hotel bar than I have at the tradeshow booth. So anyway, that's a long winded way of saying like, I think that's such good advice in that, it's okay to change your opinion, when you've got new information. I think that's excellent.

Devin Bostick  41:56

Totally. It's on the flip side of your story, I remember when I was at the height of switching over from CEO to President and feeling the disappointment, I was really disappointed in the progress. Like LuckyTruck had done well, but it didn't hit my personal goals. So I felt a sense of failure in my own execution. But I was at ITC and definitely met up with some founder friends and partied a little bit each night. And I missed a lot of opportunity from doing that. So I had the reverse of the lesson from you. But you know, I feel like you got to accept it. It was a fun week. I look back to it fondly, but you learn from these things. So.

Callan Harrington  42:34

Yeah, and I said in the newsletter, for me it was like very much not a post of like, don't drink. Like I'm the last person to ever like to say anything to everybody. But it is more of, you know, your previous assumptions can be wrong, and you don't know how things are necessarily going to go. And as you get new, more information, it's okay to change your mind based off of new perspective, which I love that, I love the story of how it kind of changed and once you got together with other founder friends at ITC, I think that's fantastic. So Devin, last question I have for you is, you know, I know we could talk all day and talk about- I know you're getting back in the game, and I'm not surprised to hear that when I hear about the passion that you have for founding companies, and especially then that early stage, and how you did this walking around New York and, and calling 100 truckers. That'll be the thing, I probably will- of course outside of the prototype, but like that will be the thing that's like, listen to this, right? Like that's where if people ask me, I'll point them  to this episode, to hear that part, the secret shopping, like that's how you're really going to get to the root of whatever it is. But if you could have a conversation with your younger self, what would that conversation be? What advice would you give them?

Devin Bostick  43:46

I would start by handing my younger self, there's a book called The Courage To Be Disliked. In The Courage To Be Disliked, it's about the story of Alfred Adler, where it's this Japanese professor, and one of his students really liked what he was saying and turned his lectures into a novel. And in the book, he basically says that humans are happiest when they create community feeling. He says that most human problems are interpersonal problems, that if say, you die at forty, and the average age is seventy, well, that's a relative problem. You died young. But if you went back thousands of years, that would have been older. So you had an old happy life, potentially, at forty. And that's where he basically says in order to be happy, it's really important that you freely opt into different tasks, and that you separate your task from your relationships. And that way, he says that every human is equal but not the same, and that everybody's walking on their own horizontal timeline. So picture everybody, just focusing on their tasks, doing it great, and not being comparative. And that's where I think a lot of the errors that I made in comparing myself with other people, and comparing where I raise capital, or hire a guy, or am I actually solving a really important problem, or just other insecurities around my abilities. But on the flip side, I think the insecurities drove me to improve. So there's definitely a bit of motivation from the fear. And then there's also motivation from the hope. But I think I would have been a lot happier if I had realized at a younger age that one's ability to wake up and look at what they have, and that's what Adler calls teleology, is often more productive than constantly obsessing about what happened in the past, which is etiology, and like things like status are often past assessments, because you're looking back at what people have already done, instead of showing up and going forward. And, in a final comment I'll make there is, I played D1 tennis back in college, and I didn't play for necessarily like a top school or anything like that. But I still had a D1 level of activity. And it really helped me appreciate one's ability to lose, and then forget about it, and then show up at the next meeting, you learn from it, but you don't dwell on it. But show up again, get up to the line, plan your shots out, and try to execute. And that's where I really connect that back to Adler, in that I would tell myself to forgive the sophomore. And to continue to recalibrate and focus on here are the assets I have in front of me. How could I take them and build something new that's aligned with what I want to do?

Callan Harrington  46:17

Yeah, I think that's such good advice. And, you know, you talked about comparison, and there's a zillion quotes on comparison. But the the thing that, you know, you were kind of talking about this, but with that comparison trap, the biggest challenge is like you could never win it. Because the second, if you're comparing yourself to one person, and you get to that point, there's always going to be another example that you'll start chasing again. You never win that game. And I know that because I've played it personally. Like, just as you mentioned, I played it the same exact way. And it always feels like you're never enough, and it's hard to ever get there.

Devin Bostick  46:54

Totally. And then you realize that your values are different than the person you're comparing to, because they have to be, you have a different way of experience. So it's apples to oranges anyway. It's just stories inside one's head.

Callan Harrington  47:06

I love it, Devin. Thanks for coming on, man. This has been excellent.

Devin Bostick  47:10

It's always a pleasure. Thanks for having me, Callan.

Callan Harrington  47:12

Yeah, absolutely, brother. I hope you enjoyed Devin and I's conversation, the story of Devin calling 100 truckers hit home with me, there is no substitute for the value you get when you talk directly to your ideal customers. If you want to learn more about Devin, you could find him on LinkedIn in the show notes. Also, if you liked this episode, you could find me on LinkedIn to let me know. And if you really want to support the show, a review on Apple Podcasts or Spotify is very much appreciated. Thanks for listening, everybody, and I'll see you next week.