Subscribe
Share
Share
Embed
Future-proof your leadership with High Octane Leadership, a place where business leaders—whether by title or aspiration—share cheat codes for unlocking workplace excellence, lessons learned along the way, and insider tips for future generations of next-level professionals. With a career rooted in building people and businesses, Donald Thompson is an award-winning CEO, speaker, and author who empowers leaders to scale with purpose. Over the last 25 years, he has helped startups and enterprises alike drive cultural change, unlock performance, and deliver exceptional results through strategic leadership.
Find him on LinkedIn, and listen here to learn how you can become future-proof too.
High Octane Leadership - Episode 185 [v1]
===
Chris Heivly: [00:00:00] Here's the one thing I know. The product that you're envisioning in your brain today is not the one that's gonna make you successful. I just know that. And maybe you're the one exception, but I don't really wanna say that because then they think that maybe they're the one exception, right?
Donald Thompson: Welcome to High Octane Leadership with Donald Thompson.
This season we're diving deeper with more solo episodes where I'll share the experiences that have led to recognition by EY, Forbes, Fast Company, and others. Not as a boast, but as milestones on my entrepreneurial path. From growing multimillion-dollar firms to successful business exits, and building high-performance teams with a global perspective.
I'll reveal the insights and strategies from my journey and share them with you so that we can win together. Alongside these solo episodes, we'll have industry visionaries and thought leaders, and we'll explore effective leadership.
Chris Heivly: Ready to empower your leadership journey with real success stories?
Let's embark on this transformational journey [00:01:00] together.
Donald Thompson: Hello, and welcome to another episode of High Octane Leadership with your host, uh, Donald Thompson. I am really excited today, and, um, I'm here with a good friend of mine, Chris Hively, who quite literally mapped how we navigate the world- ... right? And we'll talk about MapQuest in a minute.
Right? And now helps entrepreneurs map their journey building successful companies. As co-founder of MapQuest, Chris helped transform how millions of people find their way, and now is transitioning that into scaling businesses. The $1.2 billion acquisition would be enough to mint somebody, and they would go off and, and continue with their golf adventures and different things.
Chris decided to double down in ecosystem building, and as long as I've known him in, in the Triangle and, and obviously nationally, has been a champion for entrepreneurs, not only in words, but also in helping them through his teaching, through his writing, and through a lot of the startup summit work and different things that he does.
[00:02:00] His reputation now is as the startup whisperer, mentoring thousands of folks, $75 million in investment capital, serving as, uh, senior vice president at Techstars. Without going a lot further, Chris, welcome to the show. So glad to have you with us.
Chris Heivly: Uh, other than falling asleep at that long list of, you know- Actually, Don, I wonder if I ever said, you know, when I...
People ask me to characterize my career, I, I said, uh, I have a label. It's called career ADD. You know, it's only that long because I get bored easily, but anyway, uh, thanks for, thanks for having me. I'm gonna... I'm looking forward to this as well.
Donald Thompson: One of the things, Chris, and, and we'll jump into a lot of different, different topics, but I do wanna take that step back, and then we'll accelerate forward, right, of building that, that major business, having that major home run that, that kind of allowed you to, to really take it next level in building and startup ecosystems into different things.
But you started out wanting to be a geography major. [00:03:00] Your dad was like, "What are you gonna do with that?" Tell me that origin story as you went from kind of an idea and aspiration to actually building something super meaningful.
Chris Heivly: Yeah. Well, what you're gonna find out, Donald, is it's not unlike just about anything else that's been a success.
The long tail, you know, is longer than the hockey stick up, right? We all wanna think about the last three years and not the 15 years before it. Um, I was, or am, a geography major as an undergraduate. I actually got a master's degree in geography, uh, right afterwards. Um, made it down from Philadelphia, where I was born, and a state college I went to.
The interesting thing back in that day, kind of in the '00s, uh, we're gonna, you know- ... just kinda, you know, we're not gonna date anything here. Yeah, that's right. But, you know, I took a computer mapping class. By the way, this is in a mainframe era, right? This is how old this was. And, um, and so computer mapping was nothing like anything even [00:04:00] close to what we imagine.
But sometime- it's like I think almost all of us have that moment, whether in a college or somewhere, where s- like, this thing goes off and, like, I wanna do more of that, right? So I had that moment, and what was interesting, it was such the new day, that my... I had a, a geography, um, not a counselor, but you know, your, your, the person you work with.
I can't remember what, what that word is, but, uh, he was a geek, too, and he's like, "Let's figure this out together." So here's, like, a student and a professor as peers saying, "Let's figure this sh*t out," right? Um, but he made me go over and take some computer science classes.
Donald Thompson: Okay.
Chris Heivly: So for me, in n- late '70s, early '80s, here's a geography major that has, I can't remember, 12 or 15 hours of computer science in their brains.
And so when you rewrite history, at least the Hively history, what, what do big breakthroughs... Big breakthroughs are when you jam two things together that haven't been jammed together before. [00:05:00] And so for me and for the people that I... what I did for 20 years in that business is, you know, how do you digitize, computerize, how do you bring technology to mapmaking and then map delivery and all that kind of stuff?
So that's the long tail. So I was a geek. Yeah, I, you know, sat down with an IBM PC when it first came out and was like, "Oh, my gosh, this is crazy."
Donald Thompson: Yeah.
Chris Heivly: You know?
Donald Thompson: When it... As we, as we now take a step back from that history piece to now what you're doing today, and as you've really built out kind of your foundation around startups, Build The Fort, and looking at how to really minimize complexity of entrepreneurship, right?
Which as I read and has ex- have experienced... And, uh, to the audience, I wanna share a quick story, and Chris may or may not remember this, but we had a cup of coffee, it's been maybe seven, eight years ago, and we were in American, uh, Tobacco Underbrown- Underground, one of the little coffee shops there. And I said, "Chris, I've, I've built a few things.
I'm doing a few things." How do you think about evaluating, [00:06:00] right, a product that's go to market, its viability? And I, I won't- I'll consensus into the thing that I've never forgotten. Said, "Don, sometimes people code things before they have something commercially viable. Talk to 100 people about your business, and through that 100 conversations you will then have enough understanding of what to build, what the market will offer you, and then are you the entrepreneur that should bring that business to market?"
And I remember writing that down previously and just locking in on that, and that has helped me tremendously as I evaluate things personally or for others to take out some of that complexity. And so what I wanted to give- Yeah ... to you, Chris, is number one, thank you, and then here's the question, right?
When you think about Build The Forward and think about how you're helping the entrepreneurs, what are some of the tenets that you use to help people really zero in on what their next sets of motions should be after they think they have that breakthrough idea? [00:07:00]
Chris Heivly: Yeah. It's a great question, and it never goes away.
Uh, think of all the technologies you and I have been through in our lifetimes already, right? You know, here sitting in the AI world. Um, I just did a talk at, up in Durham at All Things AI, couple thousand people. Yeah. Amazing experience. And I said... They said, "What do..." You know. I said, "What do you want me to talk about?"
"Talk about the intersection of startups and AI." Um, and so the, basically the talk was the answer to what you just asked, which is all the technology in the world can make you maybe go a little faster, make you a little smarter, but it's still fundamentally a human experience, right? So don't try to bypass the human part of this and think that AI can answer your questions like who's my customer?
Do they care? Um, and so when I sit down with a founder, the first thing I wanna know is how many people have you talked to and who? Tell me about those conversations. And there's still probably 40, 50% of new founders out there that think that they can kind of [00:08:00] bypass that, that, that thing, and they can just build something that's gonna magically happen.
And what I tell them is, "Listen, I've sat with literally thousands of entrepreneurs and tracked some of their journey. You know, not obviously in gross detail times a thousand, but enough to do some significant pattern recognition, and the patterns are that your idea's only so good. Um, the market, you gotta give the market a way to react to that, either by doing customer interviews or, you know, building an MVP.
But here's the one thing I know. The product that you're envisioning in your brain today is not the one that's gonna make you successful. I just know that. And maybe you're the one exception," but I don't really wanna say that because then they think that maybe they're the one exception, right?
Donald Thompson: If you're building something, and, and this is my view, and I- If you're building to be the exception, right, [00:09:00] then you gotta be credibly spiritual in terms of your, your luck and, and grow- Right, yeah.
Chris Heivly: It's just all
Donald Thompson: luck, baby. Yeah. 'Cause you're, you're now doing a different, a different thing, whereas the successful entrepreneurs and VCs and private equity folks, they develop pattern recognition, right? And, and do that. And as you looked at building out your newsletter, Build The Fort, the book, Build The Fort, you've used a childhood metaphor that kind of pushes against some of the MBA speak, if you will.
Chris Heivly: Yeah, yeah.
Donald Thompson: How did... I'm super interested, how did you come up with that metaphor? Why did it resonate? And then now over the course of years, how has that been working and, and, and acceptance with entrepreneurs?
Chris Heivly: Yeah. Well, I'm gonna attribute a healthy part of that to luck. Um, but with a little bit of smarts, you know, thrown in.
So, um, there's an, a fellow that wrote all the, you know, most of the original code for MapQuest that worked for me for a while. Um, you know, I left MapQuest right as we took it public. They needed adults on the board, so [00:10:00] my role, and it's really most of it ex- ex- you know, was, uh, most of its explosion was me from the sidelines.
But I, you know, obviously helped put the whole thing into place. By the way, I'm the classic zero to one, and at one I get bored sh*tless and I gotta go do something else, right? But anyway, um, Marshall Clark and I worked very closely together on a lot of mapping technologies as we grew towards the internet.
And, um, after we both left, we've now gotten together two or three times to do startups together. And so, uh, s- and we have this weird language when we talk business, actually when we talk anything, um, and like we can almost finish each other's sentences, and we love kind of speaking in like f- making each other laugh through metaphors.
Well, at one point, I believe he came up with the phrase, um, when we all were starting a new idea, as build... It's like it's building a fort, right? And I had built tons of forts when I was a kid. In [00:11:00] fact, when I do a lot of public speaking still, you know, at one point I usually say, "Raise your hands if you had an idea, a business idea," and 98% of the hands go up, right?
Um, but part of that question answer is like how many people build a fort, and like just about everyone's hands go up, right? So it's a, it's a, it's a metaphor that everyone kind of can feel, not just think about. And so Marshall would say, you know, "Hey, Chrissy, you know, we ready to build a fort?" The next questions are like, "Where are we going to borrow or steal the wood?
You know, my dad's got some nails. Uh, my dad's got a tarp." You know, like all those things. And so when I thought about writing a book and thought about what I think I'm good at, which is trying to simplify very complex things, like removing the noise that doesn't matter right now, I think for early founders is a big thing, right?
They're listening and they got so much stuff coming in and they're, they're trying to do it all, and it's like, okay- Let's not worry about a CFO right now.
Donald Thompson: That's right.
Chris Heivly: [00:12:00] Right? Like, you have nothing to count, so we can kind of, like, take that off your, your mind, right? So, uh, so I just thought about the building the fort and how, you know, I always say, you know, "Donald, you and I are in the same neighborhood.
We're 10 years old, 12 years old." You know, it's, it's the first week of summer vacation, and I say to you, "Hey, do you wanna build a fort?" And you say...
Donald Thompson: Hell yeah. It sounds fun.
Chris Heivly: Yeah, like, in a nanosecond.
Donald Thompson: It's like, it's like, it's just like, it sound- it sounds fun, I want a new adventure. Yeah. And we don't think about things when you're kids, and that's why I love the metaphor.
We don't typically think about the reasons something can't be done. Right. We just think about what we wanna do, and then you go forth and get started.
Chris Heivly: So let's, let's take that and let's now do the adult version. So you ask me if I wanna build a fort. Chris, do
Donald Thompson: you wanna build a fort?
Chris Heivly: I don't know. When, when we gonna do this?
Uh, uh, when we we're... Where are we gonna get the materials? I- we don't know anything about building stuff. You know, is there a video we [00:13:00] need to watch? You know, we gotta go get some data. Like, as adults, we just create all these barriers, right? We all think of all the... We make it more complex. And so the th- the thinking behind Build The Fort and the two books I've written and, um, you know, my speaking and all that is just like, like, like I slow down.
Let me help you remove the noise. Pretend you're 10 years old building a fort, right? Like, just shed all the crap. So that's, that's the... I feel lucky that I stumbled upon it. It's become my, my thing, my wedge, so, and, uh, it seems to work. That was
Donald Thompson: really awesome. You've talked to thousands of entrepreneurs.
What are some of the chara- When, and we talked a little bit about product market, right? Talk to people, talk to customers, interviews. That's your customer discovery. There's also a component on the emotional readiness for entrepreneurship or the em- the emot- the, the grit factor, so some of those different things.
What are some of the characteristics that you look for, [00:14:00] right? If you're gonna deploy capital, time, effort, energy in working with a team or a group, what are some of those intangibles, characteristics if you will, that you look for, uh, in, in somebody you'd partner with that's an entrepreneur?
Chris Heivly: Yeah, it's a great question and, and I, I think I'll qualify th- by, to this by saying I think it's different for everyone.
And so my way isn't necessarily has to be the only way or even your way. Um, but what I'm looking for is, like, curiosity. So I, I don't mind you being confident, but I also want you to understand that some of your confidence is created in order to get you up in the morning and get through the day. We all do a little bit of that, right?
I got this. I'm killing it. Um, and some of this is gone, like, I'm not sure what this next step looks like or these, the step two, two steps from now. And I want someone to be able to be curious- Um, a little vulnerable, um, humble enough to ask [00:15:00] people for help. This is why my work on community has been where I put most of my work in the last 10 years, because I think great communities kind of have all those people surrounding you that you can reach out and say, "Uh, uh, it's not working right now," or, "I'm confused."
And, you know, every- the- that's why we call it a journey. It's like different challenges. Yeah. So you need different people. So I need... I n- I want someone who kinda understands that at, at some level, and then is vulnerable, humble, you know, curious, all those kind of characteristics.
Donald Thompson: Back to s- s- similar question in terms of your experience talking with entrepreneurs.
You talk a lot about sharing your ideas, right? But a lot of people don't wanna share things. They treat it like they're a chef, right? They don't want artists. They don't wanna share anything till they think it's ready, right? Yeah. How do you encourage people to share where they are, their thinking, right?
I'll, I'll give an example and I'll be specific. Sometimes people pitch me as an angel [00:16:00] investor in different things, and they'll want me to sign a NDA or different things, and I'm like, "Well, okay," but, like, ideas are a dime a dozen. Like, what are you t- like, what do you think you have
Chris Heivly: Yeah.
Donald Thompson: Right? Yeah. That, that is so revolutionary that I can go take and, and, and build it.
But your premise is share your idea with those 100 folks. Get that good feedback. Yeah. What do you think holds people back from doing that?
Chris Heivly: Well, it's a combination of things. I mean, one, o- on, on, on maybe a, um... Actually, on a, on a good level, they don't understand how the game's played, and that you don't do that.
And so unfortunately they don't realize they've just put up a really big red flag that they don't understand how this works. Um, and usually that means they've spent too much time just with themselves, right? In their own room, in their own head. Um, I like to say, when you're the only one in the room making decisions, then every decision is perfect 'cause there's no one there to push back and call bullshit, right?
[00:17:00] Um, remember what we said earlier, like, half of the thing, half of the product you're thinking, no one cares about or wants. So why would you go out and build this thing only to understand that your market doesn't want it? What's that? That's a waste of time and money. So share... Um, here's the other thing.
There's this beautiful graph, and I'll see if I can do it backwards. You know, it's kind of like, you know, Y-axis, X-axis, um, and this is kind of time, and this is kind of like, uh, enthusiasm, let's say, right? So you're like, you launch your product or you're, you know, launch, launch your... You have your idea in a company, and you start working on things and, you know, confidence kind of wavers over time, right?
'Cause it's hard. And then it kind of wobbles for a while, and if you're lucky- All of a sudden you catch magic, right? Well, they call that wobble the trough of disillusionment. Hmm. Okay? So the question is, so, okay, so I s- to answer your question, half of it is not understanding. [00:18:00] You have faulty knowledge about how the game is played, that we don't need NDAs, and please don't sh- not share your idea.
Um, you can't get a- anywhere without it. The second thing is sometimes fear. Fear that if I put this out, people aren't gonna get it. And so that's usually stuck a little bit in the back. It's not out front. But, uh, and it's one of the first tests of an entrepreneur. If you can't get your idea out and articulate it in a way that potential customers go, "Oh my God, I'm, I've been waiting for you to walk in my door," right?
We're all looking for that moment, for someone to say, "I desperately need your help on this." If there's not a group of people, well, y- you know, you gotta go out and talk to those people. And so I think fear sometimes prohibits people from ta- sharing this with other people. Uh, fear that they're gonna call your baby ugly.
And by the way, it is ugly, but you're gonna help it. We're gonna help you. [00:19:00]
Donald Thompson: I would add to that, and back to you describing people not knowing the game, also it's repetition and practice, 'cause you don't have a pitch until you've talked about it a lot.
Chris Heivly: Yeah, 'cause the first time you do it, right, the person sitting across you goes, "What?
Huh?" Or they ask a question, you're like, "Ooh, I didn't think of that." Well, that's the beauty of sharing it with people. You share it with 50 or 100 people, I promise you, by the end of that time period, you will know what you need to do considerably better than you do when you started out.
Donald Thompson: And, and, and I'm gonna go back to what you've, you've taught me.
And you're doing that discovery work without having written a line of code, needing any investment. Maybe you built a two to three slide PowerPoint, right? Right. But your only expenses were to just get ready to, to make that communication, and then you develop that confidence over time based on that feedback.
Chris Heivly: Yeah. So startups fail for one [00:20:00] of two, uh, one or two of the combination. They, they run out of time or money. So this 100 interviews may take you some time. Maybe it'll even take you three months, but I tell you, it's gonna save you time and money down the road. The worst thing I hate to see is someone who's worked really hard on something for a year and a half and still has not gone out and talked to many people, if any.
That's the most disappointing... I'm like, think of all that time. So NDAs, no, no real investor's gonna sign an NDA. There's maybe a couple... I always hate to do exceptions 'cause people go, "That's me. I'm the exception." You're not the exception. Um, you know, my exceptions are things like, you know- You know, some deep chemistry, pharma-
Donald Thompson: Right
Chris Heivly: me- mc- you know, medical device. And even then, you know, no one's gonna... Oh, the reason I brought in that chart, they also feel that someone's gonna steal their idea. Well, you just said ideas are a dime a dozen, [00:21:00] but even if it is a great idea, someone's gonna steal it. I'm gonna tell you, the first time that trash of- trough of disillusionment comes in, they're out.
Because it's only deep passion, understanding the customer, that drives you through that period. And if someone steals your idea... By the way, I've been doing this for 15 years. I've never seen anybody steal an idea.
Donald Thompson: Me neither. Ever. Me, me, me neither. And, and there is a fabric that I think knits together entrepreneurial ecosystems of respect for ideas.
Chris Heivly: Yeah.
Donald Thompson: Right? And, and that appreciation, right? And, you know, there used to be a time where somebody could write a physical check to someone, and the money was good, right? Yeah. And that's just how our society works, and I still feel that in the entrepreneurial ecosystem. And the, the higher level investor you get a meeting with, the more truth you're gonna get.
They don't wanna waste their time- Yeah ... or yours. Like, they're gonna give you- Do they, do they think- Exactly ... it's a good business? Fundable, not? Do they think you can run it, [00:22:00] right?
Chris Heivly: And so- I'd love to bring it back. To me, that's why I'm spending time in community, especially ours here in Raleigh, Durham, because I want you to understand the game sooner, and hopefully increase your chance of success by not wasting time or effort on things that end up you throw out or you suffer from, right?
And so know the game, and it's easy. Just talk to Donald or me, and we'll talk, we'll tell you about the game, and we'll give you 10 other people that will tell you the game. That, that's right. Right?
Donald Thompson: And the-
Chris Heivly: That's what a great community is ...
Donald Thompson: the thing here locally that I've experienced, and I, and I just believe it to be true, it's now decades, right, is people are typically open to a cup of coffee.
You might have to wait patiently to get on their calendar, right? They may give you a calendar. It might be two to three weeks out. You may have to follow up once or twice, right? But in general, if you've got a, any reasonable idea, right, our ecosystem locally has a lot of takers that'll help you s- suss it out, [00:23:00] right?
And, and, and, and go from there, and I think that's something to just remind folks that the reason you're afraid may not be real. It may be the boogeyman or the boogey person.
Chris Heivly: Yeah.
Donald Thompson: Right?
Chris Heivly: It's your boogeyman.
Donald Thompson: That's right. That's right. Now, I wanna jump, um, ahead to now some practicalities. You've mentioned in some of your work and writing the difference between mentorship versus hyperactive mentorship, and I haven't, I haven't really unpacked that term before.
What does that, what does that mean to you? How, how would you, how would you describe that?
Chris Heivly: Yeah. So there's a couple different angles I could take into this. Some, maybe we'll do a couple. But let me start with- An easy one. Government, city, county, state, federal even, across the world, but, y- you know, here in the United States, um, is trying desperately to understand that economic development, um, has to have a portion of entrepreneurship as part of [00:24:00] your kind of entre- you know, economic development, hopefully success as a city, county, region, whatever it is.
So th- there's, there's organizations and money and lots of things going. And, and the first thing that most of these people wanna do is f- with the wrong thinking that they can engineer outcomes. By the way, if you and I knew how to... If we had the playbook for engineering, we wouldn't be spending time on a podcast, we'd be building a Facebook every week, right?
So hint, there's no secret playbook or whatever. There's no magic fairy dust that's gonna make you successful. It's just you're gonna have to grind through it, learn, be fast and quick, and l- little bit of luck. Anyway, so as it rega- as it goes to mentorship, a lot of times what people do is they build mentorship, uh, in like an engineering.
You and I get matched up. I'm the founder, you're the, uh, grizzled, you know, experienced vet, and we get assigned each other, and now we have to, like, talk about the product, the company, marketing, all the challenges we have. Maybe I don't [00:25:00] like you. Maybe you don't like me. Doesn't matter. To me, true mentorship is peer-to-peer.
That professor back at Westchester University was a friend and a peer. He also happened to be my professor for a couple classes, but we were peers. I've been lucky that I've always had a peer relationship with my boss. And as my wife reminded me last night, I've always had deep relations with my boss's boss, which sounds a little ladder-y, but it probably ha- you know, younger, e- earlier in your career may do that.
But back to mentorship. Great mentorship is not assigned, it's not engineered, it's not programmed. Great mentorship is two people sitting down, showing up a little vulnerable. Um, it ha- it should be two-way. I should learn as much from you than you learn from me. And so, like, like, at, like, a hyper level, I've always been lucky enough to have, [00:26:00] at any one time, three to six people that I could reach out to and say, "Hey, I wa- I wanna run something by you."
Um, and I'll give you a, a, a, an extreme example. I think some of the best e- uh, mentorship is not necessarily functional. How do I do a Facebook ad? There's lots of ways even today you could figure out how to do that. I think most of it is emotional support, and most of it's about I've been on that journey, and a lot of it's just listening, having empathy, of course, um, which is why I think the best hyper mentorship is, is peer-to-peer and founder-to-founder.
Um, but I'll give you an example. So Uh, and you'd probably have never heard this. So in 2016, Dave and I decide to shut down the Startup Factory. That was our accelerator. I spent many years building up the Launchbox version and the Startup Factory version, and you were part of that journey. And, you know, and it was exciting, and it, you know, I, I put on a whole bunch of other events, you know, around that all to help and, [00:27:00] you know.
I was, you know, I was the dude's dude, right? I'm out there. Everywhere you turn, there's- I'm like a bad penny. There's Hively, right? And then we decide, you know what? The community doesn't need this, and, you know, we were trying to fundraise at a difficult time and, you know, let's just park this and kind of turn it off.
And the next thing you know, I'm like, "Well, who the heck am I? I don't have the Startup Factory." This is how your brain works, right? Doubts start to creep in. What am I gonna do? I like this position. I like being the dude's dude, you know? What am I gonna do next? And I happened to be having lunch. I almost always during that period would have lunch with somebody, just to connect, right?
And I'm connecting with this friend, a woman, she does crisis management for, you know, politicians and big corpo- you know, when the you know what hits the fan. And we're just having lunch, and we sit down and she says, she says, "What's wrong?" I said, "What do you mean, what's wrong?" Now I have a choice here. The choice that most of us make.
"Nah, nothing's wrong. It's all good." [00:28:00] I know stuff's boiling in my head. She doesn't let up. "I wanna know what's going on." So I decide, you know, I'll open it up a little bit, and she's like, "All right. Um, let me cancel the next meeting I have. We're having lunch again tomorrow. Let's just talk through this." It's no big deal.
We've just... I mean, she fixed it because she got me out of my own head. Yep. That's a great mentorship story on a whole nother, a whole bunch of levels.
Donald Thompson: I really appreciate that. And you've mentioned a couple times just in our chat here about being vulnerable, what you just described as the example, right?
And that is such a huge risk to so many of us because we've not experienced the value of being vulnerable. We only have- Yeah ... in our mind the negative impact of sharing a weakness, sharing a concern, sharing something that we're going through. But as I've learned, that aha moment where you get, A, sometimes [00:29:00] some great advice, or B, you just get to offload something to somebody that you know keeps confidences, not judging you- Right?
Yeah. And then you can start to unpack it yourself, which happens a lot as well. Yeah. So I, I really appreciate that story. Grant Willard, my mentor, uh, was employee number seven at IQD, his firm, and we've remained friends, uh, even through several different transactions, and we still get together at least once a month.
And I pick his brain, but he will listen to me, and I can talk to him- Yeah ... without judgment, and I can be vulnerable, right? And that's such a, that's such an important thing. I really appreciate that, that, that story. When... We talked a little bit about Techstars, and one of the things I wanna share with the audience is not only in the US, not only the Southeast, but you did a lot of work working with entrepreneurship globally, right?
And we are in a more global economy than ever before. What are some of the things you learned about entrepreneurship that you'd share with our audience that is a through point, [00:30:00] right, as you look at it globally, and then what maybe are some of the differences that you've noticed and, and seen? But just love for, to hear about that global perspective, uh, to building forts on an international scale.
Chris Heivly: Yeah. The first perspective is that, you know, I got, I put an ass groove in American Airlines like you wouldn't believe. And I'm kinda happy to not do that anymore. I think one year I did nine international trips. Um, but, uh, you know, it was a really amazing experience. So I'll give you a little hint, assuming that many or most of your listeners are from the Raleigh-Durham area.
Um, one of the best things that happened after exploring, probably visiting 100 other cities and probably doing deep dives, probably speaking and doing kind of a one or two days with maybe 50 to 60 and maybe c- deep consulting on about 15 of them, um, it gives you more pattern recognition, right? Gives you more perspective.
And so the coolest thing about this is that, uh, [00:31:00] what you mentioned earlier, being able... You can get a meeting with anybody as long as you have a little bit of patience and a tiny little... You don't even need that much push. That is very unique to Raleigh-Durham, like, on a huge scale. Got it. So I... At some point, point, we'll talk about Raleigh-Durham Startup Week.
I will tell you that I started Raleigh-Durham Startup Week because I wanted to make sure that didn't go away, that connection that, you know, it, maybe it's a little southernly, maybe it's a little Southern gentleman, maybe it's a little bit we don't have to shout from the highest rooftop how great we are.
But that the fact is that everyone will take a meeting with everyone pretty much, at least your first meeting. Here's what I learned. Um, we, we started working on, you know, with some really super smart people, Brad Fell, David Cohen, Mark Nager. Um, we started working on kind of a f- a way to kind of- Put a framework around this, this, this kind of how do ecosystems grow and prosper?
And one of the things we realize [00:32:00] is that the cultural elements that make up how people connect, um, do they connect? Do people hoard? Do people try to control? Um, all these kind of important but kind of squishy kind of concepts which we throw into the cultural bucket, that those things are different in a lot of different places and sometimes it's not their fault.
Um, super smart, uh, guy in the industry, um, said, "You know what? If w- we were gonna do work in kind of the Norfolk area." Well, what's Norfolk? Heavy, heavy military, right? I mean, structure out the gazoo, right? Right? You know, permissions and, you know, hierarchy and, you know, my view is that entrepreneurship is the opposite of all that, right?
We, we, we, we destroy hierarchies. We disrupt the status quo, right? So how do entrepreneurs gonna think when their parents and their parents' parents all grew up and [00:33:00] lived in this kind of hier- So the approach to, um, community... Communities have personalities, and they have history, and that you need to be-- work within that as part of this.
Now, there's some commonalities that you want to achieve, but how you get there are different. Um, did work in Lima, Peru, right? And, and sometimes it's not just culture, sometimes it's government policy. We take it for granted that we can do anything we want to start a company here in the United States.
Well, what if I told you in Peru a few years ago when I started working that you needed to actually create a company before you were allowed to have your first conversation, and you were not allowed to move on from that unless you officially closed that company down, right? So, like, you think about the constraints that they're accidentally-- They're trying to manage things, but by managing it, you're saying, "I just wanna go out and talk to 100 people and see what they [00:34:00] think," right?
Why do I have to spend X number of hundred dollars to set up a company and probably hire a lawyer? And so there are just so many elements that are unique to every area that what I found is you really have to figure out that, that cultural thing. By the way, isn't this like every company or every idea?
Like, you have a team. You gotta figure out how to bring them together. You gotta find commonalities. You know, you gotta have respect. That's it. Like, it's all the same whether it's a company or a community.
Donald Thompson: That is, that is beautifully put, and I think that often we over-engineer things that we natively know.
So back to your example as kids. Do you wanna build a fort? Yeah, man, that sounds cool. We're actually all not different than that, and so if you're not getting that feedback, then maybe your idea's not super cool. Right? Yeah. Yeah But, but that ability to go out, you don't have that apprehension 'cause you're just looking for a few s- few friends to go shoot a basketball or to- Yeah
build a sandbox or [00:35:00] whatever the, the case, the case may be. Chris, there is a tsunami of information about AI, a tsunami of information about how AI is going to disrupt, no more jobs for young people. AI is going to end, end, end. What is your view on how... And, and I, I, I know I'm rambling a little bit, but I'll say this.
You and I, to date, myself, the Y2K crisis, right, was just gonna cha- just destroy the world, right? When the internet hit, all malls were gonna disappear immediately, right? Like, everything. What is your... How do you position AI in your mind and what you're seeing f- both from a macro and then a, a local level in terms of what its impact is?
What's your opinion? I'm just interested in how you're thinking about these new tools.
Chris Heivly: Yeah. I mean, so you and I have lived through the first computers, probably in college. Um, uh, then the computers came to our desktop. Then [00:36:00] they became laptops, so you could carry them around. Then, you know, we had CD-ROMs, which all of a sudden we had access to lots of different information, right, all at our desktop.
We didn't have to go get it to the library or somewhere else, right? Encyclopedias, atlases, you know. Um, you know, then we get, you know, smaller and smaller, right? Yep. The phone, right, starts to change things. The internet changes things. Internet 2- Yep ... changes things. You know, Web3, blockchain, right? Like, AI, in some respects, is just another technology that will apply.
On other re- aspects, it's hugely disruptive. Um, I'm gonna s- think of that in a positive way. Um, yes, I'm a fan of some, a little bit more controls, um, I, I would love to see. Um, but it's the next tool at some level. I use it to write. I use it to think. I am curious about it, more curious than I've been [00:37:00] about a lot of technologies.
Like, I don't care about crypto or blockchain, but I care about this one. So I'm curious about it. Um, I'm telling my kids, my adult kids about it. I'm asking them what they... I'm trying to get them to apply it. The only thing I fear is some people deciding that it's just another technology and they could bypass it, and I don't think anybody should do that today.
Donald Thompson: I, I appreciate that. We are very much aligned, and I'll g- I'll tell you why in a different fashion. You're busy. I'm busy. I got a lot things going on, and I like it that way, but I'm real particular with my time, and I took a 10-hour prompt engineering course. Mm. I spent two days at, at Harvard and invested in an AI strategy course.
Right? I'm playing with the technology every day because I think it's- I'm jealous ... so disruptive that I wanna be on the front end of how it works in a application-based way, [00:38:00] not just AI for AI. Yeah. How does AI work for creative work I'm doing? How does it work- Yeah ... when I'm working with developers and different things, right?
What are the different tools? Yeah. Because I'm both enthusiastic and afraid. So my motivation- Yeah ... in my learning in this space is both enthusiasm, 'cause it can create something new. I built and published a website in eight hours. I had my folks at, at Walk West, uh, one of the companies I'm investing with, go through the security stuff and diff- and, and kind of button it up.
But in terms of the design, the content, the look and feel- Right ... right, I'm now- Yeah ... a web developer. Right? And, and that to me is, like, amazing, right? And I'm, I'm building- Yeah.
Chris Heivly: I, I got a couple hundred dollars.
Donald Thompson: Right. It's, it's just amazing, but I'm a big fan of AI. I think that the opportunity that we're seeing in some of the work that I do is around the overall literacy in education, because we're all afraid- Yeah
of things that we don't understand, and I think we should broaden the folks that understand how it can [00:39:00] be used, right? So more people can participate.
Chris Heivly: Well, it's funny, I just had a conversation this morning with a guy, partner of mine, um, that we formed the Raleigh Durham Startup Week, uh, thing. And, uh, he's very technology-forward and proficient and has built tech companies and worked for large companies.
And we got riffing about something and I, and I said, "You know what? Over the next couple years, there'll be a lot of consultants out trying to help existing organizations apply AI in lots of different ways." But I said, "Who's gonna help the Donald Thompsons and the Chris Hivelys who are kind of single proprietors in a way?"
Yeah. You know, I might have a, someone do something for me here and there, but basically who's gonna help me? I, I'm probably not gonna sit down there and figure out Claude Code. Though I could, but, you know... And so I'm like, so the next thing you know, we'll see. We'll, we'll see what happens in the next weeks or months, but maybe there's a Harvard course in, in, uh, in Raleigh Durham that, uh, a couple of us put [00:40:00] together for, for the old guys like us who need our hands held, right, through the process.
Donald Thompson: And, and back to your point, and I know we're riffing a little bit, but I, I wanna extend on it, but we should think about doing something like that and also as a way to build community. One, you identified a persona, right? Those of us that are still curious, but we're, you know, we, you know, got a few gray hairs on us, right?
In terms of, you know, we've been doing some things we've been doing. But also, I think those are really nice ways when you learn together to continue to expand community. And, and, and growing. And so as we wind, I could talk to you all day, and so we're gonna have lunch- ... so I can do that. I'm gonna buy you lunch and, and we're gonna catch up and just family-
Chris Heivly: The longest
Donald Thompson: podcast ever.
Yeah, exactly, and then family and, and different things. But I do wanna give you an opportunity to talk about RDU Startup Week, which is one of the big things that you're working on now. I, I wanna help promote that. Um, not maybe last year but maybe two years ago, I was a speaker at, at one of the different things, and you're, you're consistently in give back mode.
And so I wanna give you some space just to talk about RDU, uh, [00:41:00] Startup Week and then how folks can get in touch with you.
Chris Heivly: Uh, that sounds great. Thanks for asking. I'm, you know, it's easy to say this, but I actually think I mean it, that it's... I'm more proud of that thing than all the stuff I've done in the past, and I've had some pretty good success in the past.
And what I'm proud of, so five, six years ago, um, right before the pandemic, you know, I'm th- I'm going all over the world. I'm slowing that down. I wanna come back to my community and put my efforts into that. And, you know, understanding what I had learned from kind of taking my foot off the Raleigh-Durham Accelerator and doing all these other things was that, um, the most important thing in a startup community from a meta level is to have sustainable leadership, that leadership's gotta grow and, and build.
And, and I looked at myself and I... You heard me earlier saying that I like being the dude's dude. I didn't mind being at every event or trying to help organize or co-organize events. But what I realized is y- you're only as [00:42:00] powerful as each one of those individuals. That's not really good shared leadership.
And that though I'd like to think I was open to helping other ideas, I wasn't very intentional or proactive about helping new leaders emerge and supporting them. So when we started Raleigh-Durham Startup Week, Archie O'Connor and I, um, which was a, you know, a lunch conversation, he was, you know, in the area six to 12 months, so he's fairly new, and, you know, I was trying to connect him with people, and we decided we w- might do this together.
I wanted to organize it in a way that it was less about any one individual. You've been there. You put some event on, it's like two or three people do the whole, like 90% of the work. And after X number of years- They burn out ... they just kind of get burnt out and fade away. That's not super smart. So I said, "How can I, how can we organize this in a way that isn't about any one of us, that any one of us, like a network, can be [00:43:00] swapped in and out and the thing would go forward?"
And, um, uh, I'm sure you know Craig Stone, and I, I remember after the second one, I think we were at Pendo, and, you know, at our big meeting and, and, uh, you know, had... Everyone's there, and he says, "I know what you're doing." You're building the next generation of leaders. And like, shh, shh. That was my little side, so now more people know.
So fast-forward, first year, you know, you grab the b- you put the band back together. You grab the people that you know will step up, right? There's eight of us. Then, you know, the next year... And we probably had 3 to 400 people. The next year we did, um, I think we're up to about 16, 18 people. And it- fast-forward, we now have 49 volunteers.
Donald Thompson: Awesome.
Chris Heivly: Okay? Every task that you need to do in a four-day, four-and-a-half-day conference has at least two captains on it, so they share the burden, right? And so if you have a... You know, we have a strategy [00:44:00] content track. There's two, maybe more. I'm on the keystone track today, right? Our keystone. Um, I'll tell you why I'm at keystone in a second.
Uh, the keynotes, right? So there's three of us, right? That are out there recruiting, and organizing, trying to reach out and find the five keynotes. We have one ev- every day. Um, volunteers has two people. So no one person feels overwhelmed by the task, and it's become a family and a great group. We had 1,500 people, uh, attendees last year, probably 125 speakers.
If you asked me today, "Chris, y- you're coming up in three weeks." Yes, all our speakers are already locked in. "Who should I go see?" I will tell you, I don't even know who the speakers are because there's six to eight other people divided across three or four tracks that all built that with just kind of guidance and, like, rough lanes, and go do your thing.
Um, and, uh, it's just an amazing organization. We're [00:45:00] now a nonprofit. Um, and, uh, and by the way, we do the whole thing for, like, 25 to $28,000, right? Uh, I expect this number to go to 2,000 this year. Um, and I almost forgot the best part. When I started this, I'm like, "All right. Back to where you started.
Founders first. It's gotta be free." I hate people forcing founders to pay to access knowledge or connection or whatever, resources. So, um, I'll end here. The m- my, the most favorite feedback, and most consistent feedback I get from people, um, when they know that I'm involved is, "I can't believe how much I've learned in the last two days versus the last two years," or something to that effect.
And then my heart sings. I'm like, "Now I'm not helping one entrepreneur one-on-one. Now I'm helping a thousand," right? So-
Donald Thompson: Chris, that is, um, powerful. That is a [00:46:00] living, breathing example of what we started out talking about in terms of building community, uh- Yeah ... and being part of an ecosystem. And I'm really, really proud to know you and to, to call- Oh
you friend. I mean, I, I've, I've always respected what you're doing. I've always- referred back to notes of conversations we've had over the years, and, and I, and I get a lot of email, and I still read your newsletter and just g- k- tweak and all the, and just all the things because when you're sharing knowledge, to your point on charging entrepreneurs, yes, you're a for-profit individual, you want to, like, uh, of course, but you also realize, and, and I wanna emulate this also, is the give back can also exist- Yeah
in the capitalist of us, right? Like, you can do two things. You can build things to create money and wealth and take care of your family and all the things, and you can give back and be a part of a growing and thriving community. It's not a zero-sum thing.
Chris Heivly: It's not one or the other. And I'll tell you, in this, um
[00:47:00] At TechStars we call it Give First, um, because we want you to lead the, the giving, right? Um, and what we say is, "Listen, I ... It's not that I don't expect something in return. I, I expect something to come back. I don't know where and how and from who, but this give back is not totally charitable." That's right.
"I'm investing my time and effort into this by doing this, and at some point, it will, I will be on the other end of that and get it back." So when I called up those first eight people and say, "I wanna put together a Startup Week," right? They say yes for lots of reasons, but one of which is I've spent a lot of time helping them build their businesses, right?
And they said, "All right. I wanna, I wanna do this."
Donald Thompson: Chris, last thought. Um, how can people get in touch with you? How can they sign up for the newsletter? How can they, uh, get in touch with, uh, RDU Startup Week? How can we keep the conversation going with the folks that are, that are listening with us today?
Chris Heivly: Fantastic. Um, so [00:48:00] raleighdurhamstartupweek.com. Um, go to the site, sign up, get on our mailing list. And so we'll ... The, the fifth installment of the Startup Week is April 20th through 24th. Um, two days in Durham, two days in Raleigh. One day, Monday, is kind of a all over. To give you a sense of the kind of speakers, um, that we bring in, uh, Monday we'll have back-to-back little mini keynotes with Rani Chatterjee, chief economist for OpenAI, um, who's a former, kind of current Duke professor and a good friend of mine, and, um, Jeff Jackson, our North Carolina attorney general.
Um, so that's kind of, you know ... And every year our goal is to bring 50% of the speakers from outside- 'Cause you know what? You can find lots of sh*t me talking. It's got, it's got decreasing value over time, right? 'Cause we all do our own schtick, but we wanna get other people's schtick. So, um, lots of [00:49:00] cool speakers.
Rolling Der- Um, for me, uh, I have a, a website, uh, which is my last name, .com, heively, H-E-I-V-L-Y.com. I have a blog. Sign up there, put you on the mailing list. There's 6 to 8,000 people that kind of graciously listen to me or at least let me email their inbox once a week. Um, if you're geeking out on startup community, I still work with Techstars.
And, um, uh, in fact, I was just working on it be- here, here every two weeks we put out a little podcast, which is just me talking for 14 to 16 minutes, really small, narrow issues. Uh, I think we've, uh, uh, done 12 or 13 episodes, so every two weeks. And, uh, I, I, I'll, I'll do a little bit of pimping something out.
Uh, much to my fear for the last two years that I've been considering doing this, um, I just wrote the first draft of a novel.
Donald Thompson: Awesome.
Chris Heivly: It's about a founder and a super angel, and 18 [00:50:00] months of their journey. The notion is you can tell more truth with fiction sometimes than nonfiction. I can write all these business books behind me to, to, um, you know, and you might kinda read them, but we all love a good story.
So, um, at some point I'm gonna start another email newsletter around people interested in the novel and, and I hope that it'll be a series, you know, 'cause we always run across another founder story we can tell, right? So that's how you reach me. Oh, by the way, I also do open office hours. Open to anyone, 20 minutes.
Go to my blog, you'll see open office hours. Sign up. I do them every week. Um, like you said, if I'm booked the next two weeks, you know, sign up for the third week, and we'll talk about anything you wanna talk about.
Donald Thompson: That is awesome. Chris, thank you so much for your time. I'll reach back out over the next couple of weeks and, uh, and get our coffee or, or our, our lunch together.
But I really appreciate you being gracious with your time and energy as you always have. And, uh, I, I, I was always gonna f- get my little outro. Kaylee [00:51:00] was gonna come on and, and different things. Chris, your work is a reminder that while technology evolves, the core of leadership remains deeply human. The leaders who win aren't the ones chasing complexity.
They're the ones building with clarity, trust, and a bias towards action. That's the definition of high-octane leadership, and we really, really appreciate you spending time with us. Thank you for joining us on High Octane Leadership with Donald Thompson. Today's episode is a step in our collective journey towards leadership excellence.
Remember, every story we share and every insight we gain is a piece in the puzzle of our leadership journey. For more insight and detail, hit the subscribe button so that we can stay connected. For deeper information and more episodes- Go to donaldthompson.com. Continue to lead with vision and purpose, and until we meet again, embrace your role as a high-octane leader in the ever-evolving world of [00:52:00] business.