Luke Buchanan - Co-Founder of Redi Health: Recruiting Great Employees, Landing Enterprise Deals, and Challenging Your Ideas

Luke Buchanan  00:00

The attitude within the organization is we always try and bring in the right person. We don't just bring in a person because we're feeling understaffed or we're feeling overworked. And when you take that mentality and you put it in place, you end up with just a group of people that are, in my opinion—I'm sure most founders say this kind of thing—I think it's the smartest group of people I've ever worked with. Every single person is unbelievable, and just when you get that kind of talent together, then success just follows that.

Callan Harrington  00:27

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 another episode of That Worked. This week, I'm joined by Luke Buchanan. Luke is the co-founder of Readi.Health. Readi.Health eliminates the confusion and complexity of the health journey through unparalleled access and support. Prior to founding Readi.Health, Luke was the Director of Pharma Account Management at CoverMyMeds. He joined CoverMyMeds before its acquisition by McKesson and helped continue to scale the team post-acquisition. This was a really fun conversation, and in some of these areas, we really got into the weeds and got some real actionable takeaways. We talked about how Luke and the team balance working on the core business versus building what comes next. And if you've ever been in a really high-growth, innovative company, you know how much this is a constant challenge. We also talked about Readi's process for recruiting great employees. And to me, there really isn't anything more important than bringing on the best people that you can possibly bring on. I love the breakdown that Luke provided in our conversation. Even with those two subjects, which are some of my favorites, the part of the conversation that I loved the most was talking through how Readi landed its first enterprise deals. For an early-stage company, this is an incredibly daunting task, and I loved how Readi accomplished this. In particular, the mindset and approach they took to landing these clients, I think, is excellent advice for not only anybody in a startup or early-stage company but is a great playbook on how to approach this in any size business that sells to enterprise. So, with that, let's get to the show.

Luke Buchanan  02:39

It was a group of individuals who had come from startup and larger company together that had now decided to launch their own healthcare company in a similar space to where we had all played. The launch of Readi—the day that we "launched" it—we announced it on LinkedIn, and we were all really proud about it. That's when we linked to our website. And so, all the founders, the first early employees, we all flipped our LinkedIns. We're really proud of it. The weeks leading up to that, we're combing over the website because it's the first step into displaying what this new, innovative technology is in the space. And so, every single sentence was scrutinized. There was not a single spelling error on the entire copy of the entire website, and we had combed over it so many times. And so we launch it, we're pointing everybody to it, we're not being shy about the fact that we're here, we're here to shake things up, we're here to disrupt, and all of a sudden, we start getting some texts. So we saw the pharmaceutical manufacturers, and there's a portion of our program that is going to be white-labeled to their product. The generic form of that that we were showing on the website for partners was PharmaPlus, and the design of that—which is not part of the copy of the website—had a spelling error in it. That was very unfortunate, very, very unfortunate. And so people started texting us. They're like, "Hey, you have a bad spelling error on your website." You know, here we are, having left our good jobs at our existing companies, and now we're starting our own thing. We're really proud of it. The last thing we want to do is launch with showing that maybe we don't know what we're doing. And so what it was was a small but very noticeable spelling error in the actual picture designs of our platform, not in the actual copy of the website. So we had missed it. Instead of saying PharmaPlus, it said PharmaPus. And right? This is announced to our networks on LinkedIn, potential customers that we want to buy that are in pharma. Yeah, they're seeing this thing. Everybody's seeing it, all of our former colleagues at our former companies—you know for a fact, right, that that's not intentional. It doesn't matter who it is, whether they know the industry or not. The launch of Readi on that day is one of my favorite stories of the company because it really represents the fact that in startup, you can do everything right, and you're still going to miss one or two things that end up going wrong.

Callan Harrington  04:51

It's so true. I'm just picturing you in that moment when you saw this and you're getting all of this. Was this a situation where, like, the body temperature just went up about 500 degrees, or was it an "All right, we just got to deal with it"?

Luke Buchanan  05:03

Initially, right? Your heart is dropping into your stomach, and your ears are burning, and you're like, "Oh my gosh," you know? But at the end of the day, it's really not that big of a deal, right? And we got it corrected fairly quickly. And now, honestly, I am so happy that happened. When I look back on it now, it is hilarious. We tell every employee at Readi that story, right? It's that no matter how successful you end up being, you're always going to have those kinds of things happen, and you need to shake them off.

Callan Harrington  05:30

When I think of that, it's funny. I used to do this thing as a sales leader. We called it the Cold Call Hall of Fame. And whenever a new rep would start, at the end of the week, we'd all get together, and we'd play some of these calls from the Cold Call Hall of Fame. These are all recorded calls. So these are all the top reps just bombing on these calls, and like the most embarrassing things. And it was to the T what you just said. It doesn't matter how good you become, there's just going to be things that are out of your control. Or where you're at now is just not where you're going to be later down the road. And so I love that story, and I want to circle back to this. I'd love to talk a little bit about your origin story. You were at CoverMyMeds, one of the most successful early—probably, I actually, I'd still say what—one of the most successful tech startups along this period. Walk us through that. What was that journey like, and how did that ultimately lead into starting Readi?

Luke Buchanan  06:18

CoverMyMeds, incredible company, fortunate enough to be early there to the point where it was pre-acquisition, got to go through the acquisition and then even into post-acquisition. So being on a journey like that, it teaches you a lot, not just about a particular industry, but it gives you so much opportunity as it relates to learning about yourself, getting to flex your entrepreneurial spirit, being able to just do a lot of different things that might not be within your job description. And so I always say, like, a month there was a year of experience. That's what it felt like. And anybody who's in startup is going to know that mantra, right? It's just—you get so much experience, you learn so much. That was great. But I started there, actually, right out of college, and I majored in philosophy. I had no applicable skill to go get a job, but CoverMyMeds, they were hiring people in these entry-level positions that maybe weren't by the book as it related to their degree or their background, and that ended up serving them very well because they got a lot of these different perspectives, these diverse attitudes. And so I was hired into the lowest position there, a call center position, very quickly moved out of that, and had some data training from my studies. And so I just went into an entry-level data analytics role. Quickly there, like the opportunities I got, it just allowed me to grow the expertise as it related to data analytics and architecture, and that became sort of my wheelhouse for a number of years there. So my background is in data analysis. And being in that, you end up learning the product, you end up learning the industry so intimately, more intimately than really any other position at an organization, in my opinion, is those who are analyzing the data from your products and from the industry that you have—you get such an interesting perspective. And so it prompted me to dive a lot deeper into things other than just what CoverMyMeds touched. So the origin story of Readi came out of understanding what is known as patient support programs that are offered by pharmaceutical manufacturers. CoverMyMeds kind of played in that space. McKesson kind of played in that space. They had some more direct products. But during the acquisition period, I really dug into that and saw, like, "Hey, this is an enormously broken system. Talking about problems a little bit—you kind of glossed over their philosophy major. I've heard you talk about this. I'd love to dive into this, that you said that that actually helped you more than you anticipated when you got into the business world. What was it specifically? For one, being in a field of study like philosophy, or really any social science or humanity, it's going to teach you how to read fast, remember easily, and innovate quickly. That's essentially all it is, is sitting around and thinking how to solve problems, some of which are known to be unsolvable. That is essentially innovating in any industry. You're looking at something that is the status quo, and you're like, "How can I make this better? Or, how can I solve this problem that to date, nobody has solved yet?" And so it takes a lot of painstaking work to think through that. The other side of it is, like, philosophy in particular—there's a segment of it that is just known as logic. There's general logic and then symbolic logic, and that is just ripping apart ideas and arguments to really figure out if they're valid. And one of the biggest mistakes people make in startup is a false start. They believe and fall in love with their ideas so deeply that they're unable to see the shortcomings or the invalidities in it. And one of the things that I think studying those types of arguments in a really deep way, from having a philosophy background, it allowed me to take a very objective look at my own hypotheses. And the approach was instead, like, "How can I make this happen? How can I make this idea come to light? I need to prove myself wrong." I have to get to the point where I'm just trying as hard as I can with this idea that I have. How is it wrong? How is it not right? Where are the points of logic that break down? And that just helps you refine the idea so much to the point where you have the best chance of it succeeding. There's no guarantee, but it really helped, and continues to help, do that with new ideas.

Callan Harrington  11:19

Here's where my head's going when I hear that. On one hand, I love it; it makes total sense. You should be looking for all the reasons why this would not work. But on the flip side of that, if you're starting a company, you've got to have a lot of confidence, absolutely, that this will almost—you just have to believe that it's going to work when you know 90-plus percent of businesses fail. How do you strike that balance?

Luke Buchanan  11:40

I don't think confidence in your idea is blindly believing that it will work. I think that it is finding ways to better prove that it is going to work. There's a lot of different ways that confidence shows up. If you're just like, "This is going to work no matter what, I know that it will." You hear stories like that with some of the most disruptive tech companies in the world, and I think that that's great, but that is 1% of companies out there, and I think a lot of that ends up being bravado as well, too. Really good founders of companies, right? I don't know if I'm actually one. I believe that I am one, but they are always trying to prove their hypothesis wrong, and that's because every time you try and do that and fail, you gain more confidence that you're on the right track. And confidence isn't an overnight thing—you generate that after painstaking days, weeks, years of optimization and diving into your own idea and hypothesis. It also allows you to stay current on how things that are not within your control may be affecting your idea. Markets shift. The financial landscape of the U.S. shifts very often. Healthcare shifts every single day. And if you're blindly accepting that your idea is going to work, you're gonna miss out on how that may be affecting your hypothesis and the problem you're solving.

Callan Harrington  12:50

Is this a process that you are going through in a vacuum? Is this a structure that you've created for your team? Do you do this company-wide? What does this look like?

Luke Buchanan  12:59

Well, first and foremost, I think it's more of an attitude than an actual process. The process is a really good product professional is going to take you through this in general. You're going to have an idea, you're going to have a hypothesis, you're going to do user and market research to see if that's actually true, and then you're going to build iterations of that to try and prove out that the idea is actually there and that it'll get adoption, or it'll solve this particular problem, or it'll increase sales by X amount. The attitude of trying to prove your hypothesis wrong, really, it's more of an attitude than it is an actual process. So the executive team at Readi, we are always going through that. It is very important that if somebody throws out an idea and everybody—all four of the founders—are like, "Yes, that will work." Somebody has to take the ball on at least playing devil's advocate. And we always do that very well, too. You have to beat up your idea because you're probably missing something. So there's no formal process that we put into place at Readi around this, but you always need to be trying to get better. We call it the "get better mindset," and you do that by questioning what you're currently doing. There's three values, and then there's—we call them belief, behavior outcomes. So there's three beliefs, and then there's behaviors that we believe exhibit those beliefs under each one of those, and the "get better" mindset is under "redefine the standard." That's our third value, and that is the vicious rejection that healthcare is broken, but we can't do anything about it. Healthcare is broken, but at Readi, we believe that we can, and part of that, on an individual level, is the "get better" mindset. Even if you're an expert in what you're doing, you have to find ways to get better. If you get better individually at Readi, you're going to raise everybody else's attitude and their "get better" mindset.

Callan Harrington  14:35

I love that. That's super interesting. I haven't heard that before. So Readi is getting off the ground. One of the things I'd love to dive into is—you just mentioned this—you have four co-founders, and as I understand it, you had one co-founder, and then you expanded that to a couple. Can you walk us through that process? How did you form that team? What needed to be there? What was the reason? I mean, that would be an exception to the norm on that. I'd love to hear about that.

Luke Buchanan  14:59

Yes. So it started with Jamin Gandhi and myself. And Jamin was at a company called Beam Benefits, which is another very successful Columbus startup here in town. I don't know if you could even call them a startup anymore—they've been so successful. But we just met through the ecosystem of startup in the space. We were both passionate about entrepreneurship, passionate about innovative ideas, and I actually recited to him the original idea of Readi, which was slightly different than it is now, but it was essentially streamlining the patient support process—still very much the same thesis. And a couple weeks later, he just recited it back to me and said that he had been thinking about it and came up with a couple of solutions that were almost to the level of somebody who had been in it multiple years, and he had been nowhere near. So I was like, "Okay, this guy's maybe one of the smartest people I've ever met. This is a no-brainer. I need this guy on the team." And I also think it was good—we didn't have a deep personal relationship before that, and I think it's great. If you have ideas with friends, everybody sat around and been like, "We should start a band. We should start a company. We should open a bar," right? But when you have that foundation of maybe more of a professional relationship to begin with, that was great. But we still had major gaps, one of which was on the business development side. I was not a salesperson; Jamin was not a salesperson. You had two relatively technical individuals that were coming together to build this. And so that's when I approached Nate Ream, who was at CoverMyMeds, about this idea. And again, Readi was nothing at the time—just an idea. And he immediately, as expected, started adding to it, to the point where, okay, this isn't my idea anymore. Nate just made it a million times better with his insight, and obviously his background on customer set. It just made a ton of sense. And when you're that early, you can decide, like, "Well, maybe it was Jamin and I that were co-founders," or maybe Nate. But if it's not off the ground yet, and there are people coming in and contributing to it, they're co-founders. And why not ask them to be co-founders? There's something very special about that. And so that just made a ton of sense. And then Nate said, as we were working through the idea, he was like, "Hey, I know Kyle Grimslet at CoverMyMeds, and I think he'd be interested in just hearing about this." And then in talking to Kyle about it, it just became abundantly clear—abundantly clear he was just going to accelerate things even further. And so I think, right—the norm is like one founder or two founders, or maybe even three, but four? Like, why would you do that? Well, if it makes sense, and you fill different roles and you fill different gaps, why would you go against it to say that you need to have two founders or no more than three? That's the same type of status quo attitude that entrepreneurs shouldn't have to begin with. We have four because it made sense, and it continues to make sense, and it's as simple as that.

Callan Harrington  17:31

With four founders, how do you make sure that you're not stepping on each other's toes, that the voices are heard or not heard, and be able to make decisions quickly still?

Luke Buchanan  17:41

It's not always perfect. You got to communicate often and honestly. In the same way that you have a team that's growing and it's not clear what that team does, you need to communicate with each other. So, you know, things move really fast in the startup, and I'm not going to say we've gotten it right every time, but you just have to make sure that if you have four founders, they're all going to be running in different directions. It's very clear early on when you're stepping on each other's toes, but as you grow and scale your organization, that becomes less clear because you have teams that might be doing the same things and overlapping, and so you just need to be so crisp on the communication. I know how cliche that sounds, but it's as simple as setting up—either technical teams often do stand-ups. Engineering teams do standups. Product teams do standups, where they take 15 minutes a day and they say, "Hey, what's everybody working on today?" I think if you have two founders, or three or more than that, you should do the same exact thing every day. You should start with your core group of the founding team or executive team or extended leadership team, whatever works for your organization, just by getting together and saying, "What's everybody working on? What's everybody's primary goal today?" From a team perspective, it seems really granular, but that's the only way you can ensure that you're not encroaching on each other's goals, counteracting them.

Callan Harrington  18:49

I'm a huge fan of The Daily Huddle system, and I say system because that rolls up from the individual contributors to the managers, the managers' meeting, to the executives that lead, all the way up. And I do think it helps just create a much better pulse on what's going into the organization, definitely. So I want to talk about these different ships. You've touched it a couple times on how it's different at the early stage versus a later stage. Talking about the early stage, this is an enterprise product, and yeah, one of the challenges of an early-stage business that sells to the enterprise is oftentimes an enterprise product's 12 to 24 months to be able to get one of those in. How did you guys get through that period? How did you get the first couple of clients? You raised some capital, so you gave yourself some of the runway, but at that point, still, you've got that sales cycle. And then oftentimes there's a lot of security requirements. What did you need to put together to make that happen?

Luke Buchanan  19:43

It's interesting, and I can only speak for the pharmaceutical industry, maybe healthcare in general. I'm sure it's different outside of that, but there's two primary pillars of an organization early on that I think are critical: data and relationships. And if you can have those two things on your broad, and then externally, you have a much better chance of getting it off the ground. And those things tend to build, right? So the MVP, or if it's just market research, that's your initial data, to go to somebody and say, "I have something here." The relationships are having somebody to go to to say, "I want to be the innovative partner with you. I want you to be the innovative partner with me on this new thing." And we had that, right? When you develop these types of relationships in the industry, then you can go to these people and say, "I have this new idea. I respect you and how we've done business in the past. I want you to innovate this with me." Those people are extraordinarily rare. I want to be really clear about that. One of the things I always say is, right? You have 5% of an industry that wants to innovate. You have 80% of the industry that doesn't really know if they want to innovate, and that's really your target market. And then you have 15% that's never going to buy your product, ever, because they don't want to innovate. They just want to eat and skate. So that's fine. It's good to figure those people out, but that 5% that wants to innovate—if you're selling an enterprise product, you need a little bit of data. And then you go to those people and you say, "I think I have something here, and I want you to be one of the people that helped me do it." And there's a lot of downstream benefits to that, right? Early adopter pricing, maybe it's free for them in general, in terms of the security requirements, like they're probably going to work with you on that to help shepherd that through. Because if they're truly innovative and they want to make a change in their current role, then they're going to eat that up. You're coming to them with a new idea, and they get first dibs at it, not only to put it into their strategy and give their product a competitive edge, but also to shape that. And if it is something that becomes industry-wide, then they get to have their fingerprint on that, which is pretty cool.

Callan Harrington  21:34

Is there a great example of this? Is this the early adopter segment, or is this the innovator segment that you're referring to?

Luke Buchanan  21:39

I mean, I think the two overlap. Early adopters are probably a little further downstream from what I'm talking about. I'm talking like earliest, earliest. It's almost like a co-innovator, maybe like your innovative sponsor in the industry. I don't know if there's a particular stage in what you're referring to that's particular to that, but for us, it was like, here's a few trusted people that we know want to make change, which is rare in any industry, in my opinion, if they're not already an entrepreneur trying to do that. So you go to them, and they're not really an early adopter even yet, right? They're just sort of that person who's like, "Here's what you need to do for this to impact me to the point where I have to buy it." And if you can have that conversation, if you have the relationships to have that conversation, then you're golden. You will be able to create that product that they're willing to then buy or use, and then that gives you more data to then go to market and prove to other people you don't have that relationship with that they also have to buy it. And then the cycle continues.

Callan Harrington  22:32

Yeah, and so much of it is just getting that first one that is the hardest.

Luke Buchanan  22:36

Yeah, in my experience, there's typically a lot of fast followers. They're excited about it, but they just don't want to be the first. Yeah, well, you know, this is advice I would give to anybody who's starting a company, too. A lot of people say, "I want to be the first to market for something." They don't. They don't. They do not. They want to be the second to market but say they were first. And so you got to figure out who's actually willing to be first, right? And knock that pin down. And then you go to all those people who want to say they're first but are actually second. Go ahead and tell them they're first. That's fine, no problem. Let them say that. It's no big deal, right? But that first person, that's where deep relationships are really, really important—to figure that out. It's, in my opinion, the most critical part of starting a company.

Callan Harrington  23:14

So you had this with a co-founder. If a co-founder doesn't have this, is this leveraging your network as much as you possibly can—your investors, whatever that might be?

Luke Buchanan  23:22

Yeah, yeah. Well, I had some of these connections as well. I don't know if every industry is this way, but in healthcare and in pharma, in particular, anybody that you're spending time with and working with, you can either treat it like it's a job, or you can treat it like you're expanding your network and you're building relationships. I chose that second route. Whenever I was sitting down with a manufacturer partner or even a vendor partner in the space, I took it as an opportunity to try and build a relationship, rather than looking at it as just a part of my job. There's a couple of benefits to that. One, you build those deep relationships that if you decide you want to branch out and do something risky and innovative, they're likely going to want to help you along with that, or at least listen to you and give you feedback. Two, it's just more fun to treat people that way, to treat them like they're not just part of your job, but you actually get to build a relationship with them, and you're very likely going to do a better job anyway if you're treating it that way.

Callan Harrington  24:09

Approaching that with a long-term mindset, to me personally, has always been key. I'm constantly surprised relationships that started 10 years ago, you may not connect for a couple of years, but then you can reconnect at a conference, or whatever it might be. I'm amazed how much those come around. It consistently blows my mind.

Luke Buchanan  24:29

I think that's excellent advice. Definitely. Professional relationships also have this weird fortitude where you don't have to talk to somebody for years, like you were saying, and you see each other at a conference, and there's this enormous happiness that you both have. If you've done a lot of business together, they take a long time to get deep, whereas a personal relationship, sometimes you can meet someone and overnight, right—you feel like you're connected, and you have a lot in common, and you can start hanging out right away. Professional relationships take a lot more investment, and they're a little bit more guarded, but they tend to last, weirdly, a very long time, and you don't have to put a lot into them once you've established that.

Callan Harrington  25:05

That's pretty interesting. I never thought about it that way. I wonder if that has to do with the fact that it's like you have this camaraderie with people that have been in the same industry. I have it in the insurance space, you know, for years, because we've seen kind of the ups and downs and all that. And it sounds very closely what you're describing, certainly in the pharma space. So let's talk a little bit about the stages of the business. What was the biggest challenge that you had when you're growing this in the earliest stages?

Luke Buchanan  25:29

Yeah, so like pre-seed, seed—the hardest thing is just getting it off the ground, right? That first customer, without a doubt, is the hardest thing to do because you are trying to find somebody who is, frankly, very much willing to take a risk. And if it's a big risk, if it costs a decent amount of money, then right—their job could be on the line if you screw up. So you gotta have a lot of trust to make that happen, or a lot of data. So that is easily the hardest part early on. 

Callan Harrington  25:54

Did you go big on the first contract, or did you ease your way into it? 

Luke Buchanan  25:58

We went pretty big.

Callan Harrington  25:59

Love it. For our listeners that don't do a lot of enterprise, a pretty common enterprise motion is you do a proof of concept, then you do a pilot, then you go full rollout. Seems like you skipped straight to stage three on that. Is that right?

Luke Buchanan  26:11

Yeah, it was now. So pilots are great. I think they're very helpful early on, and we were in a position where we could get patients into our platform without having to sell into enterprise. So Readi is two-fold. It has a consumer platform that is available to everybody, whether or not we have a partnership in place with the pharmaceutical manufacturer. And then, of course, the experience is significantly more robust when a pharmaceutical manufacturer is partnered with us. What that allowed us to do, though, is get a lot of data on patients, in general, how they're behaving on our platform, and we were able to take that and essentially go practice a normal sales cycle. Now we did have relationships with the first adopters that came on, but those were strictly a little bit more pilots. They were more like market research initiatives. And I think that those would have been true pilots or free programs, but when we started taking this to market, we had just actual buyers end up moving quicker than some of those early co-innovative partners. I think that's just a product of our specific technology. But, yeah, it was standard sales that ended up coming on earliest with Readi, which I think is a great thing.

Callan Harrington  27:12

I think this also has so much to do with mindset. You're playing to win, you weren't playing not to lose.

Luke Buchanan  27:18

Yeah, big difference there. And sometimes you have to switch between those things. I think you should always try and play to win, if your market can bear it, for sure. And we did that, right? I think if you go act like a small company, I don't even like saying startup to customers. We're a startup. Okay? What does that really mean? Though you're a small company that's doing something really innovative? Maybe some people understand that. Most probably don't. So just don't even say that. There's no point. There's really no difference if you're behaving like a true organization, if you have the security measures and the certifications in place, if you treat your employees like real employees, and you're doing actual work and putting it in the market, and it's working, you're a company, a C Corp, an LLC, it doesn't really matter. So don't go in and say, like, "We're new around here," or "We're a startup, a small startup out of Columbus, Ohio." That was ridiculous. We didn't do that. We said, "This is the technology. We're Readi. This is what we do." Simple as that.

Callan Harrington  28:11

I love it, because you're right. You can't go into a big company and act small. They need to see this, just, "Okay, this might be where the company is at now, but they're all buttoned up. Yep, these are experts that we're hiring. There's the confidence or that they're going to execute, and they understand our needs and what we go through."

Luke Buchanan  28:29

Yeah, if during the buying process, they find out your company is small, and that's a surprise, that's a good thing, right? So I don't know why you would lead with that upfront. You want to be surprising.

Callan Harrington  28:40

I love it. Okay, so first client, and now the other challenges that you experienced in the early stages, pre-seed, seed?

Luke Buchanan  28:46

The other one's talent, right? Getting good people is always hard, there is no doubt about that. But in your earliest stages—I'm talking right, sub 10 people, sub 15 people—you're convincing others to take a risk and essentially come build this new thing that is very uncertain with you. It's important to be transparent about your company at that stage, right? Some people might have 24 months of runway. Some people might have eight months of runway, right? True innovative people who want to kind of take that leap, but aren't themselves sort of founders, they will do that, but you have to convince them as to why. And so some of the earliest challenges we had were just getting the right kind of people into the organization. It's hard to do. We luckily had good networks here within Columbus, and were able to quickly bring in just the most amazing early team that I could possibly imagine. I mean, everybody that is coming to Readi, I look at them like, "Wow, this person is so much smarter than I am." That's always a great thing. But in your early pre-seed and seed stage, you're charged with growing the business right, ensuring that the business is well-capitalized, but then also doing all the work around bringing the right people into the business. And those things should work all together, but you'd be surprised how they stretch you apart sometimes, and you can't focus on any one thing in its entirety. And that kind of leads me into the last challenge in the early stage, which is just your time management. You can be stretched so thin and not be able to focus on one thing. That's where having multiple founders has really played to our favor in terms of right, you can lean on each other to pick up the ball, even if it's not in someone's particular wheelhouse, to be able to do it. So pre-seed, seed stage—you have your first adopter. Very, very difficult. The talent, incredibly tough to get in. But when you start finding your own network, and you'd be surprised just reaching out to people, "Hey, I've started something. You're amazing. I've always loved working with you. Would you ever be willing to take a risk on something instead of just staying on your normal career path?" When we started doing that, you'd be surprised how many yeses we got. People are so hungry to do something either risky or innovative or something just exciting. And that's great. Part of it too, though, is the Columbus startup ecosystem is pretty great, and so there's a lot of people here that want to go join something early. 

Callan Harrington  30:54

The recent use cases of CoverMyMeds, Bold Penguin, Root—you’re seeing a lot of exits now so people can start to see that, "Okay, this thing is actually possible." Yeah, of course, this has been out in San Francisco, New York, a number of other cities that have seen that a lot, but we're starting to hit now. I totally agree with that. And in the conversations that we've talked about, and you just highlighted it again, you talk a lot about your team. And one of the things that even just in prepping for this, like, "I want the opportunity to talk about my team." Why is it so important to you?

Luke Buchanan  31:23

I think that the reason why Readi is successful is because of the team that we brought on. It's important to me because we put a lot of time into it. And so one of the things that Kyle Grimslet, our Chief Strategy Officer and also co-founder, he's always said, "We don't hire for people, we hire for talent." And so there have been times where we have months and months searching for the right person for a role, and we get down to the end of project days or code days, and we say, "None of these people are meeting the mark." Make no mistake, there's a big gap that needs to be filled, and it's burning other people. But the attitude within the organization is, we always try and bring in the right person. We don't just bring in a person because we're feeling understaffed or we're feeling overworked. And when you take that mentality and you put it in place, you end up with just a group of people that are, in my opinion—I'm sure most founders say this kind of thing—I think it's the smartest group of people I've ever worked with. Every single person is unbelievable. And just when you get that kind of talent together, then success just follows that. Everybody's bought into the mission; everybody's bought into just being very good at what they do. People don't talk about that very often. If you can just get people who are just really excited to get good at what they do and be good at what they do, you have a much better chance of success. And actually, our first belief at Readi is "We are all patients." Everybody's a patient, and part of that is empathy through expertise, which means like, everybody at Readi is going to be an expert in something better than everybody else in the company at something, and that's where you need to show your empathy—is that you bring expertise to the table. You know more than everybody else here, and you have to take an empathetic approach paired with that expertise in order to create a positive outcome for our patients. So when we bring people into the organization, we need to make sure that they're empathetic and that they have expertise in something, that they're true experts in it. And so far, at Readi, we've done that with every single person. It's something I'm incredibly proud of. The empathy aspect, though, that's really the thing that I'm most proud of. Everybody takes an approach where they are trying to make everybody else better based off of the thing they are best at. It's rare, and I just think it's amazing.

Callan Harrington  33:23

Using an example, Amazon has a very tight structure around hiring to capture a lot of what you're talking about. And one of the questions they ask is, "Will this raise the collective average of the team? Will this additional hire raise the collective average of the team?" Do you have a process that you do, whether it's an interview process, scorecard process, hiring process, whatever that might be, to ensure that that level stays high? It's got to be something there. Because what I'm hearing you say is, like, if we've got additional open spots, we're not just filling those spots with somebody that can fill those—it's got to be the right person.

Luke Buchanan  33:56

Yeah, well, I mean, a hire that doesn't fit—first and foremost, a hire that doesn't actually fit what you need is going to end up costing you a lot more than if you just take a little bit more time. And so that's more of, I think, a recruiting and hiring mantra than it is sort of the empathy through expertise. Getting that out of somebody, figuring out if they have sort of the grit or the hunger or the, I guess, the moxie to take on the startup attitude, and then finding out if they're empathetic—that is not particularly easy to do. So I think it just comes from having a lot of conversations. And I know that interview processes can be pretty stringent, but the way that we kind of approach it is an initial phone interview, which is great, right? That's really to screen out people who are serious about joining the company and want to join Readi, don't just want a job. Very important first step, get that out of the way. Secondarily, though, we go through multiple interviews with those who are closest to the role, and then panel interviews with the executive team, either the founding team, or those that are just in leadership over that particular business unit, depending on the role. And right, while you can't really question specifically for empathy, it's something that we all watch for. So those that are interviewing, that's really where you need to ensure that you're driving like, "Hey, you need to make sure that this person has the grit, the hunger, and you need to make sure they're empathetic." It's difficult to actually ask questions to figure out if someone is empathetic, but if you get enough of your trusted people in front of this person to have a conversation, they should be able to figure that out. The last step is a project day or a code day, and we make those pretty robust, pretty strict, and frankly, a decent amount of work. If somebody says, "This is too much," then you know that they probably don't have the grit or the real desire to come work for Readi. If they knock it out of the park—and oftentimes we put mistakes in those projects that we do right or we question in a way that could even be a little bit frustrating. If somebody gets frustrated, if you see that they get angry, they probably don't have empathy because you're asking them questions as if you know less than them. And if somebody recognizes that, then they're going to be very patient with you and empathetic. That's really how we finally get to that last step. It's during the presentation—sort of, even if you're smarter than the person in that particular aspect, you act like you're not, and you see how they respond.

Callan Harrington  36:06

I think that testing for the anger, which is tough to do. I've been through that. I've done those tests, and, you know, I've given constructive feedback. Nothing I thought was very aggressive to see, and depending on how defensive somebody can come to that—and it's not to say that sometimes it's not warranted, right? If I went into that the wrong way, then I deserve that. But I hear what you're saying on that to the team.

Luke Buchanan  36:31

Well, I want to be clear too. It's not like we're pushing people to get angry or anything like that.

Callan Harrington  36:35

Well, you're punching them, no kidding.

Luke Buchanan  36:38

It's more so just right, like trying to understand more of what they're saying, or asking them to say it in a different way. And most of the time, people have empathy, and you're just trying to figure out if they're able to pair that with the expertise that they have—that is a skill that not everybody has.

Callan Harrington  36:52

Yeah, I should clarify. I'm looking to see how they take feedback, because feedback is incredibly important to me, and telling them, of course, to highlight the parts where we caught them doing it, doing it right? So I love that you're in kind of that scale phase at this point. What is on your mind now? What are the challenges that you're dealing with now, and you're thinking through personally as it feels like you're kind of shifting out of that founder to a CEO position? Is that right?

Luke Buchanan  37:18

It shifts back and forth on a daily basis. That's part of the struggle of, I think, like the scale phase in some ways. But, you know, the thing that I'm focusing on most now is—this is going to sound contradictory, and it is, but you have to figure out a way to do it, at least I feel like I need to—is, how do you both stay laser-focused on improving what you currently have, but also think about and act on what's next? Those two things don't always work. Good companies, they are always thinking about what's next. They are never reliant only on their core product or the thing that they feel like is kind of working. Readi is in a scale phase, so for us to roll out net new products right now maybe doesn't make sense, but we need to think about how we're positioning the organization long term to be able to act on opportunities that are, you know, quote, unquote, the next big thing, or the next thing for Readi. The staying focused part is just ensuring that everybody's aligned to innovating and optimizing what we know is working, and trying to figure out the things that we think maybe are holding our product back today. And so there's a lot of processes in place as it relates to technical teams, our product teams that are doing a fabulous job at that, but thinking about what's next can be very difficult because there's a lot of ideas you may have out there, and this is where a good founding team has to kind of keep each other in check that might, in some way, shape or form, actually hold your current product back or distract from it in a way that could be really detrimental to it. I don't have the answer for that right now, but one of the things that I think has been great is with Kyle, our Chief Strategy Officer, we have 90 minutes every Friday, if we can make it work, that we just call a weekly deep dive. And we talk about, right, the industry, what we think is next, how Readi can play in different spaces. And it's quick little bits as to, here's an idea. What do you think? Bad idea? Here's why. Here's an idea. What do you think? Bad idea? Here's why. 90% of the ideas are not good—philosophy, right? 10% of the ideas might be good, and those are the ones that we kind of write down, create a catalog of them, and then we chase them down a little bit later when we talk about the long-range planning with the broader leadership team.

Callan Harrington  39:16

Is this something that you're organizing for? What I mean by organizing, like McKinsey horizons for success, right? You've got horizon one, core business. Horizon two, emerging business. Horizon three, that future state business, and you're actually organizing teams around these. So you've got a team that's really thinking 10 years out. You've got a team that, once that starts to get, you know, the first kind of POCs and things like that, it goes into horizon two. Once that becomes almost kind of—you have product-market fit on this next product that moves into the core business team. Or is this a portion of people's time is dedicated towards thinking about what comes next?

Luke Buchanan  39:51

Given the stage of the business, it doesn't make sense to devote people specifically to thinking about that far ahead. And frankly, when you are right in an industry where your product isn't as established as a company that's been around for 10 years, right? That's doing hundreds of millions of dollars in revenue, you have to take the approach of—the people working on your current product are also the best ones to understand what the next step is. So if we were to split that up and have people just thinking about the future, they wouldn't have the intimate knowledge to be able to change with the current product and understand how that's playing in the company, and how that may impact any sort of idea as to what's next. And if you don't include individuals who are just working on the product in that conversation about what's next, then you're probably going to end up with a next that doesn't make sense for your now, and that's really important. So it's a portion of people's time, but it's not even really organized, right? Because you can't schedule good ideas.

Callan Harrington  40:47

Which is true, most of them come on a walk or something like that when your mind's completely gone.

Luke Buchanan  40:51

That's right. But if you're constantly trying to think about what is next, eventually you will find out what is next for you. But if you're just expecting it to come to you, much less likely. If you don't have a practice in place to pull out good ideas and then act on them, it's much less likely that you're going to execute on the good idea that you do have. So it's more about just putting the structure in place to be able to empower your people to tell you what's next, or to figure out if an idea that they have is the thing that you should chase down as the next iteration of your product or a new product line that you end up devoting resources to.

Callan Harrington  41:24

How did you need to evolve personally to be the right CEO for this phase of the company?

Luke Buchanan  41:30

Well, that's still ongoing. I want to be really clear about that. Frankly, a lot of it is just trying to fill the gaps of the work that, frankly, you don't have someone to do yet, and then when you feel like you're doing a bad job at that, it means that the business has grown to the point where maybe you need to step out of it and bring somebody else in. So I never really had to do founder-led sales because we had Nate, but I was supported on that. Good example. Early on, I did a lot of the demos for our product, building them in the design platform, Figma, and presenting them to clients. And then it got to the point where it was—what they were asking for and what we needed to present was so far out of my expertise, I didn't have a prayer of executing on it. So we brought someone in specifically to do that, and I stepped out of it. So my gauge on it is like, okay, what work needs to be done? And as soon as I feel like I'm doing a very poor job at that, that's probably my cue to step out. And sometimes it gets to the point where you're trying to hang on to something because you think you're doing a good job. And it takes your founders coming to you to say, "Hey, Luke, you're dropping the ball on this man. It's not your thing. The business has matured beyond the CEO having to do this thing." So the thing that I feel like I've had to adopt is just a good resiliency and humility to be able to admit to myself and be able to take the feedback from my founders as to when it's time for Luke to let something go. It's time for him to step into this thing, or he's just not focusing on the right thing. The CEO job description changes dramatically. So does the Chief Strategy Officer. So does the CTO, and so you need to make sure, as a founding team, you're calling each other on, "Hey, your role maybe needs to be a little bit different now." And I feel really grateful that I have founders around me that are willing to do that, and we put that structure in place, but I've had to adopt a humility that I didn't really understand when I started the company, which is just, "Hey Luke, in every single thing that you step into, you're going to get to the point where you're not good enough for that particular task, and you need to be okay with people telling you that, and you need to be okay stepping out of it."

Callan Harrington  43:29

Matt Wickhouse said something very similar on the show and saying he's like, "When I start to feel the pain of me doing this thing, it's time to put somebody that's better than me into that position." So Luke, last question I got here for you is, if you can have a conversation with your younger self—age totally up to you—what would that conversation be? And what advice would you give them?

Luke Buchanan  43:52

I will pick me that as Readi started. So this would have been May, June-ish, timeframe of 2021, and my advice would be really simple. It would be double how long you think everything is going to take. But here was my mindset early on, we're going to move really quick. We don't need to raise as much capital as what people are telling us. That was a mistake, right? Because we're going to move so fast. We have the expertise. We have this good technical talent that we're bringing in. We're going to be able to do what most teams do with 10 people. We're going to be able to do it with five or 20 people. We're going to be able to people. We're going to be able to do it with 10. That was true. That was all true, but you can only move as fast as your fastest customer, and it doesn't matter how agile you are. It doesn't matter how fast your team is. If your customer is a certain speed, that is your speed limit. And I didn't realize that early on. I just thought that, because we were going to be able to move quickly, we could do things in double the time, but the customer is the customer, and they're going to move just as slow as they always have. That was a tough lesson to learn early on, and I wish I could go back and say, like, "Hey, think about your buyer's process to this product, not your ability to build it, or your ability to put it in the market. You have to stop thinking about how you're going to disrupt this space. How is the space going to adopt it? How is the space going to accept being disrupted by this product?" We didn't think about that early on. I wish we had because it is all the difference in making sure that you raise enough money, you hire the right people, and you just don't get frustrated.

Callan Harrington  45:22

I mean, I think it's an interesting point. If it's not the customer, there's almost always going to be something for somebody else. It might be the ability to get in the right talent set. For somebody else, it might be the market. I'll use myself as an example. 2021-2022 was on fire. I was like, "Oh, this is going to be easy. We're going to grow this and sell this in three, four years." And then 2023 hit. We're very much in the tech startup space. It's like, "Okay, now this isn't going to happen. This is going to be longer than I thought," which now, at this point, I accept that, and I actually look at it totally differently, but I totally agree with that, man. The highs and the lows just happen. You can't avoid them.

Luke Buchanan  46:01

No, they happen when you do expect them, when you don't expect them, it's just all the time. But you got to enjoy those too—the highs in particular. Obviously, it's important to take a moment and look back on what you've built because you forget to do that when you're moving that quick.

Callan Harrington  46:13

Couldn't agree more. Luke, this was a blast, man. This flew by. So thanks for coming on. I'm glad we could finally get this together.

Luke Buchanan  46:20

You bet, anytime. Glad we made it happen.

Callan Harrington  46:29

Absolutely. I hope you enjoyed Luke and I's conversation. I loved Readi's mindset to landing enterprise deals—they 100% play to win, and I think that is critical to landing very large deal sizes. If you want to learn more about Luke, you can find him on LinkedIn in the show notes. Also, if you like this episode, you can 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.