Using a rubric for your next career move, shifting from startups to large companies, and the power of business cases with Dan Caldwell (VP & Head of Insurance at Cinch Home Services)

Callan Harrington 00:01
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.

Callan Harrington 00:21
Today, we have Dan Caldwell. Dan is the Head of Insurance at Cinch Home Services, and I've known Dan for a long time, so I'm really excited for this. Also, this is the first time I'm testing in-person recording, so we'll have to get some feedback on how that goes. Dan, welcome to the show.

Dan Caldwell 00:40
Thanks, Callan. It's nice to look into your baby blues and be here in person. Thank you.

Callan Harrington 00:45
You know that's the sole reason I did it right there, so I appreciate that very much. So tell us a little bit about Cinch and what you're doing for Cinch Home Services.

Dan Caldwell 00:54
Cinch Home Services is the second-largest home warranty group. It's been around for over 40 years and is privately held, with a lot of initiative to solve problems in different channels, one of those channels being insurance. I came over to Cinch, and I've been looking at the landscape of home risk and thinking about, as a traditional home warranty company, what we could do to solve some of the problems within the insurance value chain, if that makes sense.

Callan Harrington 01:20
It makes total sense. Now, Cinch is a very large company, right?

Dan Caldwell 01:25
Yeah, since it's private, we don't normally put out numbers, but it's near or around 800 employees, so yeah, it's of size.

Callan Harrington 01:33
So, a good-sized company. And prior to that, you were at Nationwide, which is a mega company. You may have heard of them, yeah, Nationwide Insurance, a large Fortune 500 company. Where I want to kick it off is, though, why I mention those is, you're really a startup guy, and that's very different. Where did this all start? Where did your kind of career kick off in general?

Dan Caldwell 01:54
Yeah, you know, I've tried to drop the labels of what kind of guy I am because I think, over the last few years, I've questioned myself, am I a startup guy or what? But I'd say where it started off was, I was at Bowling Green State University—Go Falcons—in Northwest Ohio. It all starts with starting a fraternity in college, right? So I checked out the market without knowing that I was checking out the market. And I noticed that there wasn't quite the product that I was looking for. Got some bids from other fraternities, saw an opportunity with my roommate. There was a colonization where we had an opportunity to start something and start recruiting guys that we liked hanging out with. Maybe opportunities to not have to go through the same rigor and rhythm of what a freshman would typically have to do with a fraternity, but really just jumpstart the value that we wanted to enjoy from being in a fraternal organization. And I'd always say that's kind of like my first startup experience because, without knowing it, I was putting together a value prop. I was testing it on guys on the floor. I was putting together the organization and the chartering documentation. We had some alumni that used to be there. So, thinking about how we were going to fund this, how we were going to get started, where we were going to live—all those things were things that, as a freshman, I was starting to think about. And by the time I was a senior, I had started an entrepreneurial organization at Bowling Green, and one of the gentlemen that had participated in that was a local entrepreneur who owned an extremely large label manufacturing business that you would never know was based out of Bowling Green, but they, at least at the time, did about 2 billion label print jobs. He had a real heart for kind of the underserved populations—India, Kenya, Indonesia, places like that. He had this concept where, just to show his heart, he went out and bought, I think it was $200,000 worth of solar lanterns that he had in his warehouse in Bowling Green. And when I met him, he said, "You know, I have this vision to distribute these through localized distribution networks, but I need a business plan." So I started in my senior year working with him, almost as a consultant, working on a business plan for him. We built a charter model, like I did a lot of research on franchises and charters and built a contract. And yeah, we started selling franchises or charters to investors who had hearts for or already had nonprofits focused in these areas, a training program to go train local entrepreneurs into building their own sales funnel and selling these highly sustainable technologies like solar lanterns and water irrigation systems and such. And I'd say that gave me an opportunity to not only just work in a warehouse where labels were being manufactured, but to take something from the ground floor, literally, a warehouse where I was boxing up solar lanterns and shipping them. I was processing the orders and putting them on the truck.

Callan Harrington 05:00
Real quick, was this while you were at Bowling Green?

Dan Caldwell 05:03
It went from my senior year until about six months after I graduated. I worked there after I lived in Bowling Green after I graduated. And the reason was because I was just swamped in it.

Callan Harrington 05:15
How did you get there? For instance, if let's say somebody's in college, what was your story? How did you find this person? How did you get involved? How did he know that this was something you were even interested in?

Dan Caldwell 05:27
Yeah, I mean, I'd say something that I don't know where I got it from, but maybe kind of going back to even just my first day on campus, I went to Bowling Green because it was a sports management school. My first week on campus, I emailed the athletic director and said, "I want your job. How would I do that?" I was the only first-week freshman.

Callan Harrington 05:46
What did the athletic director say?

Dan Caldwell 05:48
He tied me in with the Head of Communications and said, "Start working the games. You'll get a good understanding of the organization." So I started my first or second week of college working in the press box. I was taking stats, with binoculars, keeping an eye on who touched the ball or who touched the puck. I announced baseball games at Bowling Green. I would run the stats from the locker room or from the press box to the locker room. I worked two days a week for free up there, basically just understanding the organization, understanding how a college sports athletic administration operated. It was a great experience. I was a first-semester freshman, and I was working with a bunch of seniors that were doing their internships. But it did a few things for me. One, it got me exposed really quickly. I also learned quickly that I didn't want that to be my life. So as much as I thought that I'd love sports management, I learned I think I just love the idea of being able to go into the gymnasium on the weekend and be able to go to all the games and be on the floor of the courts and stuff.

Callan Harrington 06:45
I think there's such a good learning in that—so many of the jobs that you think that you want, right? You almost create this ideal picture of what this job is, until you're in the job, and you're like, "This isn't that great." So I think that's excellent that you got that experience. What was it when you started to realize, like, this is not actually what I want at all?

Dan Caldwell 07:03
I mean, I think it's the trajectory, right? I think you start to realize, well, one, in order to get to where you want to go, these are the hurdles you're going to have to get over in order to get there. So, selling tickets, doing all the setup, I think being a freshman and doing it, it's one thing, you know, and it's nothing against the adults that do it, but watching other people's lives play out where that's their job. They go home, they see their kids after, you know, they wake up, they come back and do it, and that's their job—it's different than being a college kid. And so realizing, am I really passionate about this? Like, am I so passionate about the game, about the entertainment, about the setup, about the details that I want to do this day in and day out? No, the answer was no. I saw the hours they worked, and I recognized I love games. I love sports. I love the idea of how they put on a show. I love a lot of parts of it, but what I didn't love was the job itself. And so it became very clear very early. I'm glad I learned that sooner than my senior year because I saw a lot of seniors doing their internship there that they were learning it in their fourth year of college, and they had never really experienced what that was like.

Dan Caldwell 08:10
But to kind of get back to how I got in touch with this entrepreneur—very similar. He's active in the entrepreneurship program at Bowling Green. He was brought in to talk a little bit about starting his label business. I emailed him after and said I had a lot of interest in what he was working on and would love to learn more and how I could be of help. And that spurred a conversation in his office, and from there, I left with an assignment to go build a business plan. I said I could, and I had no idea. I mean, I knew from content organization how to build a business plan because that's part of some studies on entrepreneurship in college, is how to build a business plan. I'd say that's probably the only business plan I've ever built, as it relates to really following a content outline. But it was an opportunity for me to learn the ins and outs of a business while doing something that was completely pro bono. It was free work, but it was also something that I was passionate about putting together. I felt like it was a challenge, a deliverable to someone that I highly admired. I took it as something of extreme priority to try to prove that I could do it.

Callan Harrington 09:10
What ended up happening with the business?

Dan Caldwell 09:12
The business has continued. I think since then, it's changed hands. I think, in general, it scaled to multiple countries with charters. It still has a distribution network. I'd say it probably found hands that could be more hands-on in actually running the company. So there's still a presence of it in the countries where we sold charters, and there's still products that are moving to those individuals.

Callan Harrington 09:37
Why did you leave?

Dan Caldwell 09:39
I left because I reached a point in kind of, "What was I going to do moving forward?" The question was, I built the business plan, I was working on maybe trying to find new products to put into the market. I spent a little bit of time on the training program. There were interns, so we started having interns come from the university to help with some of the tasks and roles. But there wasn't really an operating model that had me in it, you know. And in the long term, there was someone that was already going to run the business as it relates to the day-to-day, and he was someone that had already been participatory from the management team of the other businesses. So there was already a lot of form and function already there. And as much as I was there, I was really consistently playing a consultant-type role.

Callan Harrington 10:24
Gotcha.

Dan Caldwell 10:24
And so I didn't see that role changing. I think also, you know, an opportunity to leave, maybe to finally spread my wings out of Bowling Green, and to kind of find the next thing was also framed in my mind of what I'd like to do. That's when I kind of continued the entrepreneurial journey and came to Columbus.

Callan Harrington 10:41
So what inspired the move to Columbus? Was it to start—because, correct me, you started a company right after that, right?

Dan Caldwell 10:49
So before I ended up starting that company. Why Columbus? Well, I'm from Columbus. Why Columbus? I was still dating my now wife, who was up in Bowling Green, so it was convenient. But when I came down to Columbus, it was right at the beginning of a lot of entrepreneurial surge in the city. I was really attracted to some of the ideas, the people, what was happening down here, and I got connected into NCT Ventures, where I actually—so it's kind of funny, but connected at NCT Ventures, and then also a small seven to ten-person company called CoverMyMeds. And, you know, CoverMyMeds, I couldn't really figure out what pre-authorization meant, so I didn't spend much time there, you know, because NCT was working on democratizing out-of-home advertising, you know.

Callan Harrington 11:28
Wait, hold on. So you would have been one of the first ten employees at CoverMyMeds if it was further explored, right?

Dan Caldwell 11:34
I think at the time, it was just kind of an intro. I was introduced to someone there, had discussed what I was looking for, you know, but at the same time, I met the guys at, you know, at DOmedia. And DOmedia was an early startup that had a lot of young life that came out of the Business Builders Club at OSU. And it was cool. I mean, they wanted to build the Airbnb for out-of-home advertising. You know, they resonated with me because I saw the vision of, could a fraternity sell a banner outside their house to Monster Energy? You know, I thought that was a novel concept, and one that maybe resonated a little bit more than the big macro problem that CoverMyMeds had been chartered to solve. And some of that's probably just, you know, age and maturity, but either way, they were operating almost next door to each other and trying to solve some problems. So I think it goes to show yet again, like, there was a lot going on. There was a lot starting to bubble here in Columbus relative to kind of that next wave of entrepreneurship. And I mean, I know you at the same time, you guys were working on insuranceagents.com. I mean, it was a cool time to come back to Columbus to get engaged in the scene. But yeah, I jumped on at DOmedia first because they were growing, and it was a fun role. And it was one that was insightful for me to go start my own thing. And honestly, so much of life is luck, and without that experience, I wouldn't have been able to start anything separate. Because when I was operating the supply side of DOmedia, I started noticing organic demand coming in because we had a lot of pages built. We had breadcrumbed a bunch of pages online that were better organized with more content than a lot of these suppliers had on their own. They didn't have their own websites, or if they did have websites, they were barely built. And so we were essentially building these web presences for small local supply billboard companies, park bench advertising, TVs in doctors' offices or dermatology offices, and we were giving them digital space to sell their product. And that was a new value prop that we, you know, that I'd say, hadn't really expressed with them when onboarding them, because I'd say it was still kind of early in the SEO days.

Callan Harrington 13:44
So real quick, you were at DOmedia, so you joined a fast-growing startup. So you came down to Columbus, got connected with a couple of people, and joined a really fast-growing startup. While you were there, you saw an opportunity within that that wasn't part of DOmedia's business plan, but you thought, you know, it's either we're going to go after this here, or I'm going to go do this on my own because you saw this as a unique opportunity, is that right?

Dan Caldwell 14:11
Yeah. So I started noticing that small- to medium-sized businesses were coming to our website and wanting to engage directly with some of the suppliers that we were onboarding. And with that, there seemed to be—you know, at the time, cars.com, you had all these—so one of the things that became interesting to me was really this idea that, well, it was a lead business, you know, it was that, wait, there's this digital demand out there that's going and starting their search online. And when they can't find, especially in markets where price isn't highly transparent, they request for quotes. They can't find price, but they want price, and there's a high amount of intent in that. And so I looked at a lot of the different lead models or industries or sectors that lead the lead business was going on and thought, oh, man, you know, how much more demand is out there for this stuff? And so actually, the way that—so I ended up starting—it ended up being a company that we called AdFiki, which is, you know, taking Swahili for Rafiki, which is "friend," but of course adding, you know, "ad" in front of it because it was kind of kitschy and cool, so "ad friend." But the initial concept actually was built as a business case. I mean, one thing that DOmedia did really well is they had really, really strong quarterly and annual planning meetings. They did Rockefeller Habits. So that was a great experience, kind of straight out of college, learning that.

Callan Harrington 15:18
What is that and why is that important?

Dan Caldwell 15:20
Rockefeller Habits is a strategic planning framework. It's a framework that keeps a good eye. It starts at the very basics, right? Your core values, where do you want to be? What are your market promises? What are you going to do? What are you going to promise, internally and externally, that you're going to do? What are the numbers that you think you can hit from a market size standpoint? What are your goals? And then it boils it down from an annualized basis and a three- to five-year basis to an annualized basis, down to a quarterly basis, and really down even further into like an activity, like, what are my weekly activities? And that was something that the leadership at NCT always kind of carried forth as being the way that they would do business with a lot of their portfolio companies. It's what they expected when we would do our quarterly and annual planning is to follow that template. We would do offsites. We would spend days doing that planning, doing retrospectives on the past quarter. And that's a really good rhythm to get into, especially being young. I mean, I look back on it now and say, Man, I, you know, at the time, I don't think I recognized how important that was. And now, anywhere moving forward, it's something that I, you know, I've tried to actually emulate because I appreciate it so much.

Callan Harrington 16:27
Why in particular?

Dan Caldwell 16:28
Oh, I mean, the clarity that you gain from it, the feeling of team when you know what everyone is marching towards. And we went so far as we had a big whiteboard wall where we would actually design the scoreboard. So part of Rockefeller is that you should design a scoreboard. But we designed a scoreboard on a huge whiteboard wall, gave a theme, gave an end of quarter, end of year, what our reward was going to be. I think one year, maybe we didn't hit it, but it was a Rolex, right? Like we were all going to get roll—like, if we hit that one, I wish I would have had it. But no, I mean, you know, another one was that if we hit it, you know, we were going to take a party bus out and like, do a nice dinner and this and that. Like, that was like a quarterly one, hit that. Like, when you do that, I guess, and you really adhere to it. You adhere to it because you're talking about it on your weekly cadence team meetings. It's always in front of you. At the time, I thought, you know, I mean, I was too cool for school, and so I think sometimes I didn't appreciate it as much just because I was young. And I thought maybe it was kind of like, you know, you have a lot of facilitators in college and stuff that push things, and, you know, having a scoreboard like, Ah, this is kind of, you know, this is just a little bit overdone and overcooked. No, like now, looking back on it, I say that in many ways brought our team together, a small team together. It gave us focus, especially focus when we were still kind of in the woods of trying to figure out market fit and trying to figure out what our value is. So there are so many benefits to it. But as an outset of one of them, we also had regular business pitch, or, you know, kind of a kind of business plan, business cases. So we would have business cases where, you know, there was a template, and anytime it was rhythm, so that you could build a business case for any new feature on the platform.

Dan Caldwell 18:05
And then what was it? I think it was like every other Thursday we had a business case, or maybe it was once a month. It was probably once a month where it was like a business case meeting, and it was a Google form, and you had to put your business case through, and it went on. And then basically, you had the stage in front of the team. Sometimes there'd be some of the investors, and you had to present your business case. And that wasn't just like new businesses. That was, hey, I think we need a drop-down here that includes this menu. It was customer feedback. It was from the front lines, but it had to be thought out. I think the thing that there's a rigor and a rhythm, right? There was a rigor to you have to answer these questions. You have to go through and figure out why, and then you got to present it to the team, and then we have to make decisions on, where is it going to be prioritized? How is it going to get done? And so that was, again, yet another thing you kind of pick up where at the time, you probably don't realize how valuable that was.

Callan Harrington 19:00
I mean, I can tell you both of those. I like Rockefeller. I've done Rockefeller Habits, EOS, Enterprise—what is it? Entrepreneur Operating System and OKRs, you know. I tell people at times like, do whatever one just resonates with you. They're all good. They've got their own nuances, but they're all really good. And what I find—I did it day one of starting my business just by myself, and I still will revert back to those rocks because what ends up happening is, especially in an early-stage company—it happens at all companies, but especially in an early-stage company—there are 7 million different things that you can do, and everything feels important.

Dan Caldwell 19:34
That's right.

Callan Harrington 19:35
So setting those rocks early helps. Rocks—so for people who don't know—rocks are typically on a quarterly basis, it's your two to seven, although I recommend doing about three to five. I mean, if you only have two and they're really important, that's great, but that's what you're focusing on. So when you're thinking about, you know, how do I prioritize my time? Those should be kind of your north star for that. And you mentioned another thing on the business cases. I didn't start getting into business cases much later in my career, but I would tell you having a standardized format, and you're talking about it from the product perspective, but even in the internal perspective—

Dan Caldwell 20:10
Oh yeah.

Callan Harrington 20:11
I think especially when you get into more of the executive level, you know, it's not as easy as saying, "Hey, I need to get a CRM or a lead distribution platform," or whatever that may be. You can't go to the COO of a decent-sized company and say, "Hey, I need to get this. I just need this tool." It has to be in that standardized format. You could do it the other way, but the odds of you getting that through, it's going to be a lot harder to do. So I think those are two great, great takeaways.

Dan Caldwell 20:35
I think, you know, you can overbake a business case, I think. But the thing that I've recognized now, since going through a variety of different places, is that without having learned that process of business casing and going through thinking about how this makes sense to the business, why—the why behind it—versus the cost, right? The cost, the time, the priority, the why, like the lift, putting my name on something, it's a process that I think people expect. A lot of leaders expect people to be good stewards, good fiduciaries of the organization. Thus, they're going to be thinking about these things. I found that a lot of times organizations are highly lazy, though, because they're just making decisions on a whim. They're making decisions on reaction. They're making decisions, and then they're wondering why they did things. There are tons of retrospectives, "Why did we do this? How'd that happen?" And you think about it, and you're like, if you were more diligent on the front end—if we were more diligent on the front end to think, "What is the decision being made? What is the lift? Why? What's the why? Yeah, what's the cost? What's the time? When do we think we're going to break even on this? When do we think by implementing a CRM, this cost, the upfront cost, by doing that?" Even if you don't have to operate your business to find that break-even, knowing it will allow you to better understand how to resource it, to better understand what to expect from it, and to create a lot more ownership by the person that's sponsoring it. I mean, I think the world of operationalizing that into a culture now because I experienced it early, and I've seen it work.

Callan Harrington 22:00
I totally agree with that, and I think you hit on a really key point. And you can overdo a business case, I agree. The reality is, though, it's harder to do that because I can't tell you how many times I've went into a business case, and because, you know, you want to make them rigorous, but not too rigorous, right? Because you don't want to dissuade—actually, you kind of want it to be that. You want that to be kind of a filter, right? Am I willing to put the time—do I care and think that this is going to have as big of an impact for me to actually take the time to fill out, to do it? And a lot of times I'll go through it, and I'm like, "Wait a minute, this actually doesn't—this didn't make sense to do in the first place."

Dan Caldwell 22:32
"Is this a battle you want to fight?"

Callan Harrington 22:33
Exactly. Even just by doing that, creating a filter on, is this a battle that I want to fight? Additionally, you start to flesh out a lot of—you know, I mean, sometimes it's really good to flesh out intentions. We want everyone to be of quality intention, but some people want to do something maybe for their career's sake, maybe for a new skill. Maybe it's something that they want to get into. Maybe it's an area they want to own. When you objectively make—you know, force everyone to look under the lens of what's best for the business, though, and how's this best for the business, even though a lot of it's suesaying, right? Like, you're saying, "We're going to get this done within this timeline. And this is going to be the net result. It's going to have a multiplier effect on productivity." Like, that's looking forward. That's a forecast. No one can know if this is always going to do the thing, but you've spent the time to think about it. And I would bet more often on the things that people spend the time to think about on the onset than just running and, you know, sometimes running and gunning and hoping that it all balances on the back end.

Dan Caldwell 23:29
The business that I started was a business case. So that business I pitched as part of the business case, I started calling our supply and asking them, "Would they buy leads?" I tested sending them leads, and I built a business case that was saying that DOmedia should have gotten into the lead business. And as an outset of that, it would have been destructive as a new business model, which then got me the funding by the VC to go and build this on the side with a domain, billboards.com. And we built billboards in, and we built a whole network of new build—or new domains as a separate business, separate funded with separate goals that was based on a business case that was not a VC pitch, that was pitching in front of a VC, a business case for the business that I was working on.

Callan Harrington 24:16
So you tried to build it in the business that you were in first, yeah? And then when they realized that this is probably better off on its own, it's going to be a distraction to the company that you were at, got a mutual investor, that investor said, "Hey, let's spin this out, and you focus on this." Is that right?

Dan Caldwell 24:33
That's right.

Callan Harrington 24:34
I love that. I love that. That ties that together really well. And I think the power of the business case just in general—and you try to do it, you know, it's always tough. Do you do it in the company you're at, or do you just go on your own? I don't know. I'd be interested to see how many times that goes the right way or people are just like, "Kill it. It was a good idea," say that this won't work, and it's like, "Oh, okay."

Dan Caldwell 24:57
Well, I guess you got to remember, I was still young. I wasn't as jaded by, you know, by the politics of things or, you know, the bureaucracy of things. I think I was still naive enough to want to bring a solution to the company that I was working for. And in some ways, you know, I think there's probably a lot of opportunity left on the table because we're not fostering—in some organizations, we're not fostering that business case mindset like we could probably extract more good ideas out of the people that are sitting in the seats if we didn't just close ourselves into management team meetings and think we're going to solve it on our own and hope that we're going to have someone with the tenacity to just shout it out. I think that's a wishful hope, but I think to build a structure to start to get our talent, the people on the front lines that are noticing these little things—that had I not just kind of started noticing, started tinkering, it would have just been, you know, business as usual. And so I think without that facility, without that rhythm, without that process, I think a lot of other businesses could probably leverage, you know, thinking about how do we extract insight, do it with, you know, do with integrity instead of just doing it opportunistically.

Callan Harrington 25:58
For sure, that intrapreneur model, I think, is really interesting, and we've played that together at other companies. I want to fast forward a little bit, you know, I'd love to spend the time talking about some of the times we worked together because we worked together for a number of years. But I think one of the more interesting things that a lot of listeners can relate to and have questioned is your move to go from a startup environment to a very large company. And you know, I consider myself definitely in that startup vein. I've really only done startups, and I've always had it on my mind. I think a lot of people do well. I think a lot of people, when it gets pretty tough in startups, like, "Right? Should I just go to a big company?" Like, I see people, they usually have much better work-life balance. But then again, am I idealizing something? Maybe, is not the truth. Why did you make that change?

Dan Caldwell 26:46
Yeah, I'd say, I mean, it was during 2020, COVID year, right? It was an interesting opportunity because it was presented in a way that it was an opportunity to be an internal entrepreneur, to think ahead of the curve, to present business cases, to build new investment models. And so it was an interesting opportunity to see the inside of a beast. And I've spent a lot of time, you know, when we worked together, and we were partnered with a lot of the big insurance carriers, or we were, you know, pitching them. And so to sit on the inside, I was generally curious what made those businesses tick, how decisions were made. You know, I think you recognize that it's going to be more bureaucratic. You hear all the stories. You think you know. On the outside, it sounds like that—the MTV, true story, right? "True Life, you think you know, but you have no idea." I mean, in general, people think they know, and they typically have the right idea, but they don't know kind of the machinations as to why. I found with myself that I'm best remaining curious. But when I start getting into it, then I start to mire in and want to change—I'm best sitting at that curious level, getting in, getting into a large company. There's a lot of benefits, to your point, but there are also a lot of things that you are decidingly going to have to pick your battles. You're going to have to decidingly look away at just, you know, bad decision-making. You're going to have to look away from just kind of a culture that sometimes—I think the thing that I enjoyed in early stage was the meritocracy of thinking that you're going to build something and then you're going to reap the reward from building something good. Even intrapreneur, you know, like you want to have a model where you're incentivizing people to surface good insights, to build new models, to take things to market, and upon success, you want to share that success so that they're equally incentivized to continue to do that and to do it in the first place. Some of that doesn't exist. There's a lot of philosophy, there's a lot of thought about it at large organizations. But it doesn't always exist like that.

Dan Caldwell 28:30
But the why I think it was a good adventure for me—I wouldn't probably do it another way, because I think equally, there's a lot of early-stage startups—you get cocky on one way of doing something. I think there's a lot to disrupt. There's a lot of big companies to disrupt. We've seen that, but we've also seen a lot of startups disrupt themselves. We've seen them show to not be viable. We've shown them to not be scalable. We've shown them to maybe not have leadership that can understand how to, how to kind of rein the horse. And so to race at one speed is great for a time, but getting inside of a big organization, you start to learn, "God, there is something about how the hell did they last this long to be in an organization of such size and scale?" There are certain things that they do, right? And sometimes that doesn't mean innovating. It doesn't mean being on the front end. It doesn't mean—but you also realize that they have a ton of risk too. So while you think they just have unlimited capital, there's risk in the sense of core business risk, you know, core service risks, downstream sales channel risk. The things that pay a lot of people's bills and that offer a lot of people protection are not a chip that they're going to put on the table. So you can easily sit on the outside and provide a lot of conjecture about all the things that they're not doing and all the problems that they're not solving and all this, you know. And I think, like, my theory on that is that we're like a generation that watched Amazon go build an impossible dream of Prime to get two-day shipping. I mean, I remember circling the JCPenney catalog and my parents calling in my Christmas gifts. And then in my lifetime, I've watched two-day, one-day, same-day shipping. And to do that in a vacuum, you go, "God, that's corporate innovation." Like, oh my god, that's amazing. But then to step back and realize that they lost a ton of—like, they decidingly bet on themselves, and they decidingly took profits from web services. They've done things strategically that put them in a position to have to take loss while building new gain and attacking a market in a different way. You know, we haven't seen that from financial services. And I think it's fair to say, "Well, why not?" But it's equally important to understand, "Why not?" So I guess, you know, all things considered, it was extremely enlightening to me to see that inside edge. It's changed me as to how I look at go-to-market, as I look at the startup ecosystem, funding models, pitches. I think, you know, it's definitely left me with a good taste of what they do well, what they don't do well, equally as much as how to get stuff done inside there, how to sell into them, how to use them as a partner. I had to operate in that function. So it's given me a lot to leave with and now kind of work off of.

Callan Harrington 31:00
So you went to a really large company, and then fairly recently, joined—still a large company, as you mentioned, 800 employees, but it feels like you kind of hit that sweet spot, right for you, in that this company is large, but it's not Fortune 50, and you get to be in that intrapreneur type of role. So for those, the intrapreneur is really—it's somebody that's really building something new within a very large, established company, and that's really the role that you're in now. Is that right?

Dan Caldwell 31:30
That's right. Yeah, when I was looking at leaving one big organization to go to another, I kind of told myself, after the one large organization, I'm not going to go to another large organization. I did my time. I got my stripes. I now know a little bit about myself. I know about them. I know what may work, what may not work. I built a rubric. I know I've told you this in the past. I built a rubric of what I'm looking for in my next. And instead of thinking of it so much so as the size of a company, it really came down to opportunity. In my rubric, it was more of like requirements on this opportunity. If I'm to spend time on something, here are the things that I really want to be true, what must be true for me, and that's based off of my other experiences, my past experiences. So, you know, I built a rubric that had me scoring out the type of leader, the type of team, the type of company, the quality of team. Intentionality is a big one, I think, kind of walking your talk a little bit. There's a lot of fluff messaging, so finding intentionality. But I took Cinch through the rigor of my rubric, and I wasn't going to make a decision on jumping onto a company, especially one that had ideas towards a highly autonomous, new opportunity-type build. I wasn't going to take a jump on that unless it seemed like there was high intentionality, high integrity, high support in doing that. I, you know, I had a chance to meet their board or their board chair, their CEO. I had time to spend with my direct boss and really hash out from each of them in their own terms, what they were hoping to achieve, what they saw. And what I saw through all of that was that there's a lot of support and autonomy that they were wanting to give to solve the problem that we all mutually see. But the problem wasn't fully diagnosed. The problem was there's a market, and that we have some things—the question was up for defining, and that's what really excited me was, you know, what? The how, the why—it was very blank slate, very blank canvas. And I think that when fleshing out a good opportunity, it's understanding the biases that are internal. It's understanding ego. It's understanding what's good for a board deck versus what's good for the business, and finding people that want to support what's good for the business, that sees a vision or sees a highlight of what could be. That's what I found in coming here, and that's what really differentiated it as an opportunity for me, regardless of business size.

Callan Harrington 34:02
Yeah, to tie a lot of this together, I think one of the things that's interesting, and I see this on a lot of these shows, right? But people a little bit further along in their careers, it is taking each or something from every stop along the way that you're looking for, you learn what you do like, what you don't like. And you brought up a great one, and this should be used—or I should say it's used well, a lot of times, you know, creating a scorecard, creating a rubric when you're interviewing people for a particular position, so you can make it objective. And I like that you did that. I think that's great advice to create that on the other side when you're looking for a place, because one of the biggest challenges is on both sides. You can get really excited about a particular opportunity, and you may act on emotion on there, and having that helps kind of keep you objective. And not saying that that emotion shouldn't be a factor, that really should be a factor on the rubric. And you know, how excited, how energized are you about this? But having that helps you really lay things out. I think that's excellent. So the last thing I want to ask here, before we wrap up, is, if you could give advice to your younger self—and I'm purposely leaving that open—what advice would you give?

Dan Caldwell 35:03
Yeah, I think, you know, I mean, I think it's advice that's probably a bit cliché. It's easier to see now, I don't regret any of the opportunities I've had or taken, but I do think it's easy to get caught up in trying to race other people when you don't know exactly what game they're playing. And by that, I mean I found myself being younger, working with a lot of older people that were, you know, sometimes 10 or 20 years ahead in their career. I've had the good fortune of sitting with them as partners. And you start to compare, you start to think about yourself, your accomplishments, what you need to be doing. You're trying to compete, and you're trying to compete sometimes with people that just have had more time. And it's a really bad measuring stick. You're always going to be a little—you may know a lot. You may be perceptive, you may be intuitive, you may have learned a lot, but there is something about time.

Callan Harrington 35:53
Dan, thank you for coming on this show today. This has been the last—again, first in-person, so if anybody has any feedback, you're more than welcome to shoot that over. Always appreciative. Thanks for coming on today.

Dan Caldwell 36:04
Yeah, no problem. Thanks for having me.