Ep. #1054 - Second-Time Founders

Matt DeCoursey 00:00
And we’re back! Back for another episode of Startup Hustle. Matt DeCoursey here to have another conversation I’m hoping helps your business grow. So, 1-2-3, that’s how many different companies I’ve started. And that makes me at least a second, now a third-time founder. But the real question is: is it easier to do something big and innovative or awesome when you’ve maybe done it before? Or do you have to live up to weird expectations? Or, I don’t know. That’s what we’re going to talk about during today’s episode of Startup Hustle. Before I introduce today’s guest, today’s episode of Startup Hustle is powered by FullScale.io. Hiring software developers is difficult, and Full Scale can help you build a software team quickly and affordably. But also got the platform to help you manage that team. Go to FullScale.io to learn more. If you’re not aware, FullScale.io that’s my company. And we love talking to Startup Hustle listeners, so reach out. It only takes like two minutes to fill out the hire developers form. See if we can figure out some solutions together. With me today, I have the CEO and co-founder of another one of Kansas City’s top startups. That’s what we’ve been highlighting this week. I’m really excited to continue to highlight my hometown and talk to more innovative people. And, in this case, someone who has done it once before as well. With me today, I have Phil Reynolds, the CEO and co-founder of DevStride. You can go to DevStride.com. There’s a link for that in the show notes. In fact, why don’t you go ahead, scroll down, and click that now? And take a look at what they do, so while you listen to today’s episode, you get a little more perspective. Speaking of perspective, let’s hear a little bit more from Phil. Phil, welcome to Startup Hustle.

Phil Reynolds 01:45
Thanks so much for having me. And I really appreciate you showcasing DevStride on the list. It’s an honor. And we really appreciate it.

Matt DeCoursey 01:53
So yeah, well deserved. And you are an accomplished founder. That’s part of where our title for today’s episode came from. So why don’t we just go ahead and get into a little bit more about your backstory?

Phil Reynolds 02:05
Yeah, sure. So I see you’re backing up. Right out of college, I was a musician, actually. And a totally separate background from tech. I hadn’t spent a lot of time there. But getting a degree in Electronic Arts, digital media production, which turned out to be really valuable for the rest of my career. So I spend a lot of time presenting things to people and trying to, you know, portray my business in a professional light, a lot of things you do here. So yeah, I did that for a few years and then realized that being in the arts and music is kind of like being homeless.

Matt DeCoursey 02:41
It’s very similar to laughing. Because I, yeah, yeah.

Phil Reynolds 02:45
So you know, like closing out like for my fourth year consecutively every Saturday night, like shutting down a bar with a guitar, I was like, you know, I should probably do something better with my time. And so I decided to get into software, taught myself to code, and started a company with my cousin at the time, Chris Reynolds, called Bright core, and at the time, was called into web solutions. And we were just sort of like all entrepreneurs just trying to figure it out at first, doing projects here and there and landing a whole long, complicated story. I won’t go into where we landed an opportunity to do a web-based quoting system for an insurance company. And that went well. And it went well enough that their friends started calling us, and we started investing in the insurance space and did really well with these coding systems for a while. And that scaled up until, eventually, all of our customers asked us to replace their core ERP system. And that’s where the bright core was born. And so my first company was really founded and launched from this, like overwhelming market demand in this niche in insurance. From there, that company really scaled up rapidly. And we ended up in a situation where we went from just the two of us up to just short of 400 employees, and a pretty good sized company did a series B had an enterprise customer 43 product teams was big, and it did a lot. There’s a lot of fun. I learned a lot. I made more mistakes than I care to count. And as does every, of course, but definitely a lot of battle scars and a lot of lessons learned. And one of the things that I learned in that process was after you bring in a Series B sort of private equity capital partner, the nature of your business changes quite a bit. And if they get the startup entrepreneur DNA, there comes a point in time when the scaling mechanics of the business and what’s necessary to run the business isn’t as fun to them anymore. And so, I exited the company and spent a bit of time off. I went live to the beach in Costa Rica for a bit, and it was a lot of fun, and then I got to thinking it’s in your blood. If you’re born a startup entrepreneur just can’t help it. And I, just like every night, would dream about things I could do.

Matt DeCoursey 05:02
It doesn’t wash off.

Phil Reynolds 05:04
No, it doesn’t at all. It’s like it’s an acute disease.

Matt DeCoursey 05:09
It’s a disease. It’s probably a fair way to put it, honestly, because it does feel that way. Why was I made this way? Yeah, it’d be able to relax and stay on the beat.

Phil Reynolds 05:18
Yeah, yeah. I mean, literally, you’ll be like, like seven nights into three nights or three hours of sleep a night, and you’re in your rainlessness having to spend on some stupid problem that you need. If it’s in your blood, it’s in your blood?

Matt DeCoursey 05:28
Well, by the way, do you have sleepless problems? I’m, like, very well known in the organization. Sometimes I don’t want to be that way. Like, I would prefer to be a little peace of my mind. And so people like what’s that like to like, have all these ideas and energy I’m like, okay, so if you put a bunch of bottle caps, and a blender and turn it on, hi, that’s what it sounds like.

Phil Reynolds 05:56
Yes, yes. I tell you all the time. It’s a little bit like Like, imagine, like, like people running by your head sparklers all the time.

Matt DeCoursey 06:03
Like firecrackers. Sorry.

Phil Reynolds 06:07
But here’s the thing. So you’re feeling restless?

Matt DeCoursey 06:09
Yeah, I’m feeling restless. So you exited that company. And then once?

Phil Reynolds 06:14
Yeah, so actually, it’s an interesting story. I have a lot of mistakes. One of the things I tend to do well is I tend to be pretty strategic about the decisions that I make as an Executive leader. And so before we ever decided to raise capital in a Series A or Series B, we decided that we really wanted to make sure we did secondary in each of those rounds. And that’s advice I would give any founder if you’re doing a structured formal round, always structure secondary capital into it because every time there’s a change of control in your company, the nature of the business is going to change, the nature of your job is going to change. So you should take some chips off the table. You have a backup plan. And so we should describe that a little bit more.

Matt DeCoursey 06:52
And people will refer to that in a bunch of different ways. Sometimes they’ll say clawing a little back. But if you’re, you’re with as you move forward, and these rounds and you kind of sell a little bit of your control out of the way, you as a founder, it’s advisable to not just be in this well. Part of why people get stressed about startups is because the founder lives where you don’t get paid shit, and you don’t have any money. And that gets old in a hurry. You really had, and the thing is, people are like Dude, your company’s worth a gazillion dollars. And you’re like, that’s amazing because I’ve got like, $13,000, you know, yeah, but part of it, not only money, but it gets harder to take that money out when other people have to make the decision about it. And so part of that is when other people have some kind of control or something to say about your path. You might mean, who knows where that’s gonna go. So take care of yourself, take care of your family. If you’ve built something that’s bigger than you, it’ll probably end up being okay in the end, but that’s okay to do.

Phil Reynolds 07:58
Yeah. Oh, absolutely. And I like the advice I would give to anybody whose businesses succeed and scaling is, especially if you’re the founder, you ought to be having talks with Capital Partners on a regular basis if you’re ever planning to raise them. Even if you aren’t, yeah, oh, yeah. Because we learn a lot.

Matt DeCoursey 08:16
Why? Because a lot of those people are really sophisticated and will give you good input about your own business.

Phil Reynolds 08:22
I agree with that a lot. I hear that a lot. So I always put that into my calendar. So again, I’ll get to DevStride in just a second.

Matt DeCoursey 08:29
I was gonna say we were just at the conference. No, no, it’s great. It’s great. That’s what happened to people.

Phil Reynolds 08:34
Yeah. Well, I think that the history really leads up to why I’m doing DevStride now because I think it’s a fascinating opportunity in the world. I’ll get to that in a second. The thing that I learned from running a really large scaling software team is. So again, the company grew to 43 product teams for enterprise customers. And every one of those product teams has a roadmap that they’re trying to manage, right, that capabilities are trying to deliver to the market, you know, release over release. And we’re doing that in service of all these enterprise customers. We’re bringing on, you know, five to 10 enterprise customers in a year, being implementations, multi-year implementations. And as we’re doing that, you can imagine the complexity of those roadmaps and of all the dependencies that follow all of that. And so, ultimately, what really exhausted me about my last company was trying to keep the sparklers in the head problem. I can’t let go of the details, so I know what every product team is working on and what every customer is asked for. I’ve got 1000s of details in my head, but you can’t be the conduit for all of it.

Matt DeCoursey 09:39
Burns you out like a cert. Like it’s a circuit board with too much shit flowing through it. Absolutely. And it’s really well. It’s gonna burn out circuits. Yeah, yeah, well, your realizations as founders, we want to talk about, okay, being a second-time founder. And you know, like, what do you learn on the road? Well, first off, like I did the conduit thing, it’s very easy because you’re trying to do so many different things as a founder in so many different ways. Some of them you’re like, you’re like, sitting on the toilet and watching a YouTube video trying to figure out something you need to do in 15 minutes. And sound credible, while you’re given the details of it, you’re like, Oh, my God. And that’s really, like, a real and maybe a little too realistic of a picture. But it’s true. Yeah. And you’re and what happens is by nature is because you don’t have the people or sometimes the path or the or a moment to feel like you can rest is that you position yourself to do too many things. And then, unfortunately, what you run into as an organization that’s too dependent on you being the conduit. And that’s, and that’s really that is, a path for what’s not right. It’s if I’d say that something I’ve really learned over time is to try to get away from that. And that, for me, is almost as frustrating as doing it all myself. But eventually, you have to grow up. You mentioned 400 employees. We have 300 at Full Scale, which you know. The funny thing is, the United States government says that it is still a small business or anything under 500 people telling you to run it. Oh, my God, I talked to people all the time. Yes, a huge company. Well, apparently, it’s not that small a business. There’s nothing small about that. I mean, honestly, when you get past about 20, that’s a lie.

Phil Reynolds 11:33
Yeah, really, almost every time the staff, you know, something like doubling the whole nature of how you manage the business changes, it has to fit into your point, you know, building systems that don’t depend on you, as in exceptional, outperforming founders. It’s hard. It’s hard. So I was always frustrated by the amount of dependency that would end up back on either a couple of other key performers or me. And we tried to use every project management suite there was, which I imagine most people listening to this podcast use JIRA. On Monday click of Asana, there’s a bunch of them. What drove me crazy about every one of them, is that if you’re thinking in terms of one individual project, and you go into one project with the team, and that one project that goes with that one project, those systems work. They’re awesome. But the moment you’re responsible for execution, and planning, and Strategy and Performance, across a bunch of projects at once, and especially if all those projects have to coordinate, like in my case, it was like for your for your product teams, implementing for one big enterprise customer, those tools fall over. And you find yourself doing 1000, manual things, putting out fires everywhere, and it’s just awful. So when I retired from breakcore, for a second, went live on the beach and couldn’t stop thinking all the time. All I could think about was how impossible and how intractable that problem had been for the last 20 years of my life. And it drove me nuts. America laid awake at night, I started drawing, you know, screen designs and data flow diagrams, all this stuff, my wife was fine. Like, we should probably do something She probably wanted.

Matt DeCoursey 13:14
I wonder if that’s a two edged sword. It’s like my wife’s like the same way. It’s like, you need some damping to keep you busy. And then it’s like, hey, now we’re over here now. Yeah, it’s like, well, that.

Phil Reynolds 13:28
So I’ll give you a detail about my wife in a second. So actually, we work together. And always in half, for the last 12 years, we’ve worked together. So she was my CMO at Bright core CMO, again at Def stride. But we have a very different approach to work. And I tend to be more the sparklers in the head of a million ideas. Just run it the thing I ran around, like, why is this broken? You know, and she’s very, she’s this amazing operations person. She’s very methodical, very process oriented.

Matt DeCoursey 14:02
And the two of us together, actually, I think could contain my wife working on the business that I wrote about in Million Dollar Bedroom.

Phil Reynolds 14:11
And she was basically our coordinator manager, like she’s just got a level of someone. Yo, God, I’m pointing at him across. Well, that’s true.

Matt DeCoursey 14:18
That’s, and that’s tough to do. I mean, in a lot of ways, and you know, I did mention in that same book, I actually recommend that you don’t work with your family and friends if you plan on keeping them as your friend. But it’s tough. And I’ve had so many people say to me, I’m sure you gotta see her. They’re like how do you work with your wife, we would kill each other. Okay, well then don’t work with your husband or your wife. Like it’s that simple. If that’s the case, then don’t do it.

Phil Reynolds 14:47
Well, it’s hard even if you weren’t very practiced at it. And even then it’s hard because I think one of the things that’s really difficult is if you’re an entrepreneur everybody’s listening to this podcast and as an entrepreneur don’t know you never sleep, you never stop thinking about better business, you never stop thinking about whatever core problems you’re trying to solve.

Matt DeCoursey 15:03
Sounds like a great thing to sign up for. Right?

Phil Reynolds 15:06
Right. Yeah. Yeah. And also, by the way, you turn Monopoly money for a very long time.

Matt DeCoursey 15:09
Basically just describe what I think you would describe a crazy person.

Phil Reynolds 15:14
Yeah, more or less. Yeah. It’s a form of insanity. Right?

Matt DeCoursey 15:19
Well, hopefully not. I actually haven’t. crazier when you weren’t an entrepreneur. That’s true. And I actually haven’t really

Phil Reynolds 15:27
Are you done though? You did, right? Yeah. Oh, yeah. Oh, yeah. I mean, like I said, just part of my DNA. Have you ever read the book? The Rational Optimist before? I’ve not, it’s a really good book. It’s all about some of the gate reading from a few years ago. And I picked up and read it great. And it was all about entrepreneurial activity and sort of the general drive toward a capitalist ideal, which of course, there’s a lot of problems of capitalism that we could go on and on about but generally that has produced the greatest amount of overall enduring good in the world. Yeah.

Matt DeCoursey 16:03
I just talked about the fact that I just did an episode and I don’t like to discuss dates, because this is going to come out a month after we recorded, but I had a professor from Princeton on that was a palisade intercessor. Yeah, well, you heard him talking about that. But like man, like, says, Professor Derek Leto is titled The history of entrepreneurship. And I mean, he really made a remarkably compelling case for the fact that capitalism has propelled the most meaningful and innovative and important changes in the history of the world. It’s the time that, look, I have goosebumps talking about it. That’s okay. And if you got goosebumps thinking about that, you’re probably going to be an entrepreneur.

Phil Reynolds 16:45
So in a minute, I’ll circle back around to some of them if you remind me, I’ll circle back around to some of the really cool personal stories I have on that front. I agree, it really is that way.

Matt DeCoursey 16:56
So I can either way, the Rational Optimist: How Prosperity Evolves? is a book by Matt Ridley.

Phil Reynolds 17:02
Yes, it really is. Excellent. I highly recommend it. Okay, so they sent me to Costa Rica drawing 1000 ScreenFlow. And everything. Couple of engineers that had worked with me at Ebright Corp had been doing that same problem for a long time. And some of my good friends, some of the smartest people I’ve ever met in my life. And, so a group of us just kind of put our heads together and sort of thought about how you could reimagine thinking about work and work management and sequencing, you know, work in the kind of software teams we’d spent our lives working in. And we went out and we started writing code. And not too long afterwards. Again, because I did secondary capital series A Series B and had cash in the bank, I was able to do an angel round for the company, which funded the first 18 months of operations. And my wife and I just kind of work the company for free, as most founders do, to help cover expenses for our other two founders. We got all the way to a sort of an initial go to market offering very early, the initial go to market offering. And then about six months ago, I set out to start raising a pre seed round, which went well.

Matt DeCoursey 18:10
Yeah, well,

Phil Reynolds 18:13
and many, many thanks to fly over the capital here in Kansas City. They let us round and then a group of privates and strategics. And people that I know in the world followed on as well. And yes, we were able to pull together $3.3 million on a pre seed round. And that was great. And so that funded some initial scale up activities early go to market, which is right where we are now that all closed just a few months ago. And so yeah, so now I’m back in the seat of welcoming back.

Matt DeCoursey 18:42
Yeah. Welcome back. And congratulations, and I’m sorry. Yes, yeah. Thank you both are very fair responses to that now.

Phil Reynolds 18:51
Yes, celebration and condolences. Pause for a second. First off, I want to get something that I think all of you listeners, especially in smaller markets, need to hear.

Matt DeCoursey 18:54
Now before I do that a quick reminder that today’s episode Startup Hustle is brought to you by FullScale.io. And that’s because finding expert software developers doesn’t have to be difficult. Like you can come to our platform. It takes like two minutes to define your needs and it will match you up with highly vetted, experienced people that are going to help you solve problems and work only for you. It’s that simple. Just go to FullScale.io Now that the thing that I want to bring up here, okay, pre seed round $3.3 million, and you did it in Kansas City. Yeah. Okay, so Kansas City is much like Okay, so there’s only like, eight to 10 huge markets and then the rest of us are kinda like from Kansas City. We’re from some mid market that probably has in the year. How’s like the Kansas City Royals that are good like every 30 years we get the chiefs are spoiled with it. Yeah, we are. We are we are but with that, you know you’re complaining that You can’t raise money in your town, there’s no precede capital, blah, blah, blah. It’s not true. No, it’s not, it’s not true. You got to create something that has value, you got to have a plan with it. Now, with that, I think it’s probably fair to say that it was probably easier as a second time founder.

Phil Reynolds 20:15
Most certainly, so So my previous Seed Capital Partners, all had a 26x Exit opportunity in my series B. That helps.

Matt DeCoursey 20:27
So in fairness to my comment, yes, that helps. But the thing that founders and entrepreneurs make the mistake of is, is okay, the product in the companies is great, but those people are investing in you, Phil, right? Because you, you and your team. Oh, yeah. And these are proven people that have proven results. And you need to get out, you need to understand that people, especially in the preceding round, they’re betting on the jockey, not the horse. So you have to sell yourself, your team, your expertise, whatever it is, your passion, your vision, and make it a big vision, because you’re not going to get a huge amount of cash, or anything.

Phil Reynolds 21:11
If you’re like, well, I’m thinking that I need like, 50 grand to build my MVP bucket, I need $3.3 million, because this is we’re gonna crush it.

Matt DeCoursey 21:14
Right, but can you validate that you’ve got a lot more investor attention? Because you had a bigger vision?

Phil Reynolds 21:21
Yeah. So I actually talk about that a lot. One of the things that I’ve tried to do since I landed in Kansas City is I’ve tried to be helpful to other founders in town. Thank you. And yeah, thanks. Thank you, more than anybody here. And I really, really have enjoyed that. And to your point, there is a founder of what we’re talking about, the company necessarily isn’t sure if he wants me to share it all publicly, but he was struggling to raise money. And I went and visited with him. And I did not go out and do the pitch for him. I just sat down and I looked at his pitch deck and he hadn’t talked to me about giving me the pitch. And at the end I was like this is shit. This is terrible. Like you’re doing this all wrong.

Matt DeCoursey 22:02
So sounds do something I’d say to someone. And I do it a lot. I do it because I love you not because Yeah, same.

Phil Reynolds 22:08
Yeah, well, well worked out.

Matt DeCoursey 22:10
So you don’t get that enough with people though. Me. I’m like, look, if it sucks, tell someone.

Phil Reynolds 22:15
The last thing I want to hear constructively. Yes. It’s still the last thing I want to hear on the sales team. And last thing here on pitch feedback is a great job. That’s the last thing because what do I do with a great job? Yeah, another great job is okay, do what I did last time doesn’t tell me anything I want you to. I don’t care if it’s huge. It’s a microscopic drill, which I effed up in this because I want to get better. Every second of my life, I want to get better at what I’m doing. And that’s how over time you gain those advantages. So my friend,

Matt DeCoursey 22:44
which I have, can I have a couple of pieces about what I bet. There’s, I want you to really quickly think about three things that sucked. And I’m gonna take a couple glasses, and you can tell me if I get one of them. These are the top three things that sucked. Okay, it was too long.

Phil Reynolds 23:00
Absolutely. Too long. Okay. And in the wrong places.

Matt DeCoursey 23:05
Right. Right. Okay. Yeah. If when talking about what the business did, it talked all about the features, and maybe not the benefits of what it did for the people all product and feature all capabilities. Am I too? Yep. Okay. And third, it did a really poor job of explaining to the investor how they were going to either get their money back or benefit. Totally missing.

Phil Reynolds 23:27
Yeah, if it’s there. Now that you’ve seen these before, too, right.

Matt DeCoursey 23:36
You know, there’s nothing supernatural about that. That’s the problem with everyone’s pitch deck or pitch.

Phil Reynolds 23:42
We all fall in love with our idea. And we think our ideas are the things that matter. And I’ve heard you say this before on the podcast, I know you think this. I couldn’t agree more.

Matt DeCoursey 23:51
Those are really three for three. Was there something that you really felt like traveling?

Phil Reynolds 23:56
Yeah, that’s it. That’s it every time. It’s people talking about their idea and talking about it being so focused on what they’re going to do they forget that they don’t forget the people who are handing you money. So get a little bit ahead of myself, after I exited. My position is right, Cora had quite a bit of money. And I turned around and became an LP and a bunch of funds. So one of the things I can appreciate about going to raise money is I am frequently the person on the other side of the table investing in startups. Yeah, so I know what it feels like to be in a chair. And I know my job and that pitch is to convince this person that this is the right use of their funds, where they’re gonna get the greatest maximum return. That is all they care about. They don’t give a shit about your idea. They don’t give a shit about the company that you mean they do. But really, what they’re there to do is they’re there to deliver returns and their fund or for their own personal portfolio. So you need to make that case.

Matt DeCoursey 24:46
It’s capitalism.

Phil Reynolds 24:49
Right, right. That’s why we’re all here.

Matt DeCoursey 24:50
I mean, and it’s just a fair way to say like apply for a government grant. Well, right. And if you’re, well, if you find a fund that isn’t fun, customers don’t fight. Yeah, yeah. Yeah. On the flip side of that, actually, I’m gonna back that up a little bit because I have actually put money into things that are not pure capitalism, because I think it is important if you have the resources to support things for sure. On the social side, for sure ever, like, you know, Lauren has a regular show here. I’ve been a big financial supporter of that, because I believe in, you know, some of that it doesn’t always have to be, but I will say she has focused on helping entrepreneurs. So it’s still day by what do you call it transit or whatever the fuck yeah. Hey, but it makes sense. But you can still find ways to do that.

Phil Reynolds 25:44
Yeah, absolutely. All right. Yeah. So I really think that when you wrap my story up, my friend who had been trying to raise couldn’t raise, couldn’t raise, couldn’t raise. I helped him refine his pitch, and he might raise $1.8 million the next week. And I did not help. I didn’t think all I did was refined. He was still presenting himself because he’s amazing. His business ideas are amazing. Are these dudes amazing? He just wasn’t packaging it up in a way that helped an investor recognize here’s a mature successful founder that’s gonna go crush it. And so he needed to deliver that message in.

Matt DeCoursey 26:18
I just did something similar. Yeah. And it was a company that I had invested in that has actually grown to make the list of our top 10 cities, startups. Congratulations, that will be fair. And it’s not just because we invested in it. But yeah, we’ll tell that story in another episode. But a lot of it was. I mean, it’s, it’s, it’s amazing what you can accomplish in two minutes. So maybe you shouldn’t talk more than that for your pitch, you know, like, and some of it. So what’s really interesting is I talked about the second founder, whatever now. So I haven’t ever needed to bring in outside capital. The only time I’ve ever had a quote investor is Watson, who we own Full Scale. Right? Right. So that wasn’t really the same thing. Now, some of that’s just been my own choice, because honestly, I’m maybe better off to not have a bunch of people telling me what to do. It’s a big shift. But I’ve been involved in a ton of it. And on the check, the check ride inside and so much of it and, and you talk like my evolution, and what and how and the presentation should occur is just it literally exponentially has gotten shorter and shorter, and shorter, and shorter and shorter. Like don’t look, no one wants your 60 page business plan as an introduction. They could cool one pager, you don’t end the deal and the email, want that person to talk to you. And I can make it if you are running the risk. And everyone’s trying to, hey, how much text image charts graphs crap, can we get on this slide? Maybe have less?

Phil Reynolds 27:57
Yes. I mean, I think so. I told you, I started out in the arts.

Matt DeCoursey 28:04
So I was music and what do you play?

Phil Reynolds 28:06
Well, I play a little bit. Um, I was a piano major in college for a year.

Matt DeCoursey 28:14
And so I ran up to entrepreneurship.

Phil Reynolds 28:16
Yes, exactly. Exactly. Totally. You know, actually, it’s interesting.

Matt DeCoursey 28:19
I actually could make a case for the fact that there’s a lot of correlation. on many levels. It’s one of those things that requires practice is consistency and also a lot of showing up and doing those things on the days that you might not take away the feeling.

Phil Reynolds 28:37
Oh, yeah. Well, so you think about, you know, leading as a CEO, or being an entrepreneur running a pitch deck. So in my previous job, I stood up, and I was the keynote speaker at the big annual conference all the time. And that’s very much to anything, delivering a presentation like that is no different than practicing a song on my guitar and singing and playing. I mean, it’s the same thing. It’s about understanding the importance of reps.

Matt DeCoursey 29:00
And so as a hobby, it’s just to give you an idea of what my hobbies are, like I’ve been over the last year, I’ve really been spending a fair amount of time studying the traits of genius that’s gone with that. And I’ve worked in the music industry as well. And there’s some very interesting people that, by the way, seem to be more fascinated with me than them. Which has been an interesting dynamic that I’ve gone through, like 10 years because at first I was like, they call me for advice. I’m like, okay, but the thing I learned is you can have all the talent in the world, but if you don’t have the discipline to sit down and polish it, you’re just going to be a kind of talented person. So if you really liked the people that do G even a genius and this is a very misunderstood thing because people look at a talented person and they’re like, That guy’s a genius. That is a genius. But a talented person can hit the target that everybody sees and a genius is hence the target no one even knew was there. And so with that there they go through this to the end, by the way they part of this is I’m not saying I’m a genius, but part of it is trying to understand maybe on some levels like what’s why it was I made this way. Because if you have the bottle cap, it’s in the blender kind of feels like the sparklers and all that.

Phil Reynolds 30:28
If you really do experience that, then you do get to step into that every now and then. I get into some weird supernatural stuff, again, sort of a flow where you’re crazy on it. But it’s hard to reproduce.

Matt DeCoursey 30:32
I’ve really been fascinated with musicians because you know, a world class guitarist has to get on stage as well. I like jam bands so that it’s not the same four minute and four second song. I say those guys have to get up there and kind of improv it like jazz. And if they mess up in front of 9000 people or 10 or however many then they have to deal with all the chat rooms and all the hate online afterward. I can’t believe they didn’t ruin my show. He missed one note, I’m gonna ruin your night. He played like 4 million great notes on those but you know, but how do you get around it and stay with that. And by the way, there’s one thing I like sharing because I think the thing that I’ve learned from now is you talk about the experience or some people say I’m getting old on Sundays, but I’m actually just getting a lot of experience. But the two things that hamper and restrain genius is self doubt and negativity. So self doubt can even be you saying negative things because that’s you expressing impostor syndrome.

Phil Reynolds 31:32
So many people are negative and the negativity is people around you.

Matt DeCoursey 31:35
So like I Okay, so for your first business, did someone along the way I guarantee you it happened? So there’s no way that’s gonna work?

Phil Reynolds 31:45
Oh, of course, like, yeah, of course, they were gonna pull this off your computer’s blah, blah, blah, blah, blah.

Matt DeCoursey 31:49
So at the time, I was going head to head and I am even more so in my new business and went head to head against, you know, 900 pound gorillas in the industry.

Phil Reynolds 31:52
It’s not like JIRA is like a startup and going up against Atlassian. Their big company, I think there’s some major flaws in their product design, I think they have massive respect for what they’ve done. Obviously, they’re tremendously successful and done an enormous good, but also there’s holes in their design. And so I yeah, I think there’s always going to be people telling you, what you’re trying to do is too ambitious, too hard, too difficult, too expensive, whatever. And if you let that voice guide you, then you’ll never do anything, because there’s always a reason you can’t do something. And I think the mark of a good entrepreneur is somebody who just says, I’m just gonna do it anyway. And the difference, I think, between successful entrepreneurs, and those who don’t, I think pretty much the I’m going to do anyway, kind of makes you an entrepreneur, there’s a lot of failed entrepreneurs, by the majority entrepreneurial field entrepreneurs, and the difference between those that are that are good, and those that aren’t into good ones. And they, while they are convinced that the direction they want to go is valid and viable. And they have their own conviction about that. They’re also sober about the world around them and about reality. And you have to learn to look at when I like your shit stinks too. And so you got to look at your own ideas and say, I thought this was a good idea. But this is wrong. This is wrong. It’s just that it may go back to the music analogy. Like it’s not like the first time you play a ripping guitar solo, you nail it, it takes a lot of time.

Matt DeCoursey 33:31
That’s why most people quit a musical instrument because they’re not good at it. Right? Like, no one was gonna keep it up. No one Dave Matthews did not pick up a guitar and kill it on day one. Like that’s not how it works.

Phil Reynolds 33:44
Maybe? Kirby VC drummer?

Matt DeCoursey 33:48
Yeah, well, yeah, he’s insane. But anyway, yes, I’m ashamed.

Phil Reynolds 33:52
Yeah, he really is. He’s incredible. I digress. Yeah, the whole but yeah, the like, there really is a lot to having your own conviction, running towards your dreams. And also recognizing that whatever you come up with out of the gate, is almost surely wrong. Unless you’re just very lucky to figure out where the reality is you’re gonna end up throwing away all of your original code.

Matt DeCoursey 34:13
Yeah. 100%. Yeah, what that MVP that you’re like, oh, resulted? Yeah, it’s gonna go to trash.

Phil Reynolds 34:24
Because there’s a better way. But you don’t know. You don’t know what you don’t know about your market. And so, you know, I’ve experienced this so many times in my career, where I think I have a great idea. All the swans are white until I read The Black Swan. And I’ve got a customer that doesn’t ever envision my data model is completely wrong, or my you know, my workflow is wrong, whatever. And so I mean, experience helps in the sense that you start to recognize patterns where someone says to me overly simplistic or overly specific to their business and you recognize that’s specific and there’s a generalization, and I call those echoes, yep.

Matt DeCoursey 34:54
Echoes are common in a number of different ways and Sometimes like, well, with Full Scale, you know, Matt, and I didn’t start Full Scale intentionally. He invested in Giga buck, we were going to help him build a dev team, we’re gonna mark it up a little bit gigabit burn rate, you know? And then we just kept hearing the echo of people saying, what do we need to do? Or what do I need to do to get some people over in your office in the Philippines, because I can’t find what I need here. And an entrepreneur, a good entrepreneur recognizes something like that and realizes there’s a problem that needs to be solved. And then we and then we went, you know, beta client one, beta, client two, beta client three, and we realized, okay, this is something we can do. We went into it sane. And both of us were second time founders at that point already and said, Okay, we’re only going to do this, if we can provide a world if we feel that we are going to rapidly progress to the point where we can and not even immediately, but everyone would like to provide world class value on day one, but you got to learn a lot of stuff do you do if you think your brand new business is already brilliant? You’re wrong, or you’re stubborn, or whatever.

Phil Reynolds 36:07
And that’s kind of your point about the Capital Partners are investing in you the founder, but they’re really investing in your ability to Figure Figure it out? Yes, you’re going to go in there, we’re gonna honor the customers. So with DevStride, I’m experiencing this all over again. And it’s both exhilarating, terrifying, all the things that are right. That’s all.

Matt DeCoursey 36:28
So I said, congrats. Yeah, sorry.

Phil Reynolds 36:30
And I love it. I love it. And so. So, you know, we had this idea for what we thought a practical portfolio management system should look like for a software team. But now you’ve got it in the hands of some real power users. And we’re seeing a lot of and you know, what, it’s something different. Oh, my gosh, what was so cool is, and I would recommend this for any founder today, especially when somebody’s going into an enterprise software space. We pulled together just a killer group of strategic advisors, which are like, you know, some early adopters and customers and experts and people like that in the field. And we do a monthly call with several groups of them, where we’d spend two hours and we walk them through everything we did. And we ask them for their feedback and their ideas and tell them all the things we’re about to go do and ask for all that. I’m amazed that with my I feel like I am one of the more qualified experts on this topic that there are and and I can talk about all the different project management frameworks, I can talk about the processes, what’s good and bad in engineering team, why you shouldn’t measure lines of code is productivity. I can talk about all these things really well, and I’ve lived them all. I still get on a strategic advisory call every week. And somebody tells me something I never considered.

Matt DeCoursey 37:42
I haven’t been given this every time I record this podcast, that’s part of why I do it. Well, that’s gotta be so much fun. I mean, well, it is because it’s also why we have the format that we have, because as you can confirm, I literally tell a guest before we hit record, this is not an interview, this is a conversation. We’re going to talk about a bunch of stuff, it might go one direction and Miko another, we’ll figure it out along the way. But that’s the value that I mean, I actually dropped out of five colleges, but I may have graduated from Startup Hustle University. Honestly, I mean, it’s the point, they say you have to do things for you know, 1000s of hours before we get into it. And, you know, I want to go back to the Black Swan comment and realize that maybe your idea isn’t as great as you think it is. Or maybe it’s not going to gain the traction that you hoped it would or that there’s some real flaws, and whatever it is, okay, so founders that fail, ignore all that, and just keep plowing forward. And that is the equivalent of like, you and I in a boat. And I’m like, Dude, we’re going really fast. And there is a giant rock or an island right there. And we see it, and we’re like, Yeah, but you know what, I bet if we go faster, or just ignore the rocks, the island will be alright. And that’s not the way it went?

Phil Reynolds 39:05
No, but you can never you should never ever this is this is a real balance. And you have to be careful who you can give this advice to because some people are so wracked with self doubt, you have to be careful how much you know, they’re already doubting themselves to begin with.

Matt DeCoursey 39:20
Because you get one point of feedback doesn’t mean I need to hurry up. I tend to start hearing. Yeah, when you start hearing your users, listen to your investors, listen to the end, by the way, if you’re outside of those two, well, other than your people, your employees. Outside of that, I might not care as much about what you’re saying. Because like the people that matter, okay, if you lose your users and you lose or you lose your employees, then you’re gonna have a really hard time running a business that’s bigger than just you.

Phil Reynolds 39:51
Yeah. Oh, yeah. I mean, I can’t tell you how many times I’ve told a founder Look, your business is not your code, like your code is. Honestly I know you don’t think this and I’m a computer scientist from the computer scientists listening, your code can be replaced, it really can.

Matt DeCoursey 40:13
And what can’t be replaced is the engine that produced the code into the culture engine that went out and found the customer built the relationship, you know, the critical thinking that existed that saw that spotted a problem we’re solving.

Phil Reynolds 40:20
Yes, that’s right. That’s a big critical thinking to innovate.

Matt DeCoursey 40:25
And once again, I hope you want to dive straight.com There’s a link in the show notes for that. But if you just do the exact same thing that you’re in Atlassian do not stand a chance. I mean, unless you’re, you’re better than euro was one point. Yeah. You know, it’s like in, you know, I mean, that’s the thing you got to figure out there’s but with that, the advantage you have, alright, so I often compare this to the game battleship. What’s the hardest boat to sink, man, that little, little two pegs soccer that you can spend all day because the big company is when they have to make a change or make a move. It’s like doing a U turn. It’s like turning around a battleship inside a swimming pool. So again, anecdotally, you can now maneuver and you can do something different. And you can find those couple little things. And, and look, if you’re okay, wrote Matt DeCoursey. His role in building software is annoying? And if the answer is anything other than No, go back and fix it because if there’s like a brilliant product that 99% kills it, but you remember the one little annoying thing, and on many days that’ll make you literally stop using it. Oh, yeah, absolutely. It’s true either. UX is so sometimes that one little thing can be what?

Phil Reynolds 41:43
Well, I think there’s another good book on the thing you just said called The Innovator’s Dilemma. You read it before Clayton.

Matt DeCoursey 41:50
I mean, really, really sounding like a non read.

Phil Reynolds 41:55
Oh, no, I’m just talking about things I happen to read something about.

Matt DeCoursey 41:58
So I have to give you some perspective. I buy the books that and by the way, the innovator’s dilemma is by Clayton Christensen. But yeah, I buy all of my guests that have been authors, I have their books, and I have a bunch of other books and yeah, and honestly I haven’t got any services. Yeah, like Audible or like I’ve been I listened to the only time I stand a chance on some of that is on that long plane ride to the Philippines. And I’m usually just trying to fall asleep on that.

Phil Reynolds 42:30
So I’m a member of some service, I can’t move. It’s called I should build remember right now we can shout out to him. But there’s a service, I subscribe to that where you can have any book and he lives in 20 minutes with a little app.

Matt DeCoursey 42:41
I have that for a while. I wasn’t even doing that.

Phil Reynolds 42:45
Okay, so the innovator’s dilemma. It describes the exact problem we’re talking about and describes why and why it is that as companies become larger, more sophisticated, they inherently become more. Yeah, less innovative, and therefore more ripe for disruption. And my anecdotal story on this for my business is that I’m at my former company, bright core, again, a big company, with a lot of team members. We were an Atlassian shop, and we had JIRA. And there was a point in time as a CEO, where I had two full time, JIRA admins, just keeping track of permissions and boards and users and all this.

Matt DeCoursey 43:25
Salesforce is like Salesforce. Same thing we tried to put on Salesforce had to shut it down. And why is it so complex? Trying to simplify the sales process? No. I’ll take Trello for free and do more with it than I absolutely love Salesforce. Yes, by the way, I want to point out user interface problems. So when I googled the innovator’s dilemma, I ended up and by the way, this is not a plug for you chegg.com Because it says here that I can buy the book for 1199 or I can rent it for 1199 and then it has okay it’s right there it says Best Value is highlighted that I should rent the book for the same price like that is that is a great example of losing your credibility that due to a bad user interface, do better Chegg.com. Check it with it. Yeah. Yeah. So okay, so All right, that was bad.

Phil Reynolds 44:27
So I had two full time JIRA admins, then all these projects were running in parallel. And I had to go to my board, because it was hey, so my last round. At bright core, I raised about $60 million for the business. And of course, my investors, again, they’re investing to get a return, they want to return on that money. So now I have to go out and activate these 43 teams to go build all this shit for my customers. And I go to start asking my product organization for reports. And they’re like, Well, I don’t know. It doesn’t give us that. I might like, Wait, you’re telling me I’m spinning. $30,000 a year in software licenses, I’ve got two full time salaries admitting this thing. But yeah, we’re going to need some, we’re gonna need some, an ETL team to go pull this out during these reports.

Matt DeCoursey 45:14
So then we had to hire a couple of data engineers, and basically the company after spending a half million dollars a year to get one report for my board.

Phil Reynolds 45:17
It’s terrible. And so I was there. This is dumb, it is dumb. It’s dumb, because, again, this is not Alaskans fault. Atlassian brilliant company has done an amazing job of a lot of stuff, they have fallen into the exact same cycle that every business including me, a DevStride will fall into when I’m successful, and I get bigger, we will fall into the same trap most likely, which is you’ll end up with bigger and bigger and more sophisticated customers. Big sophisticated customers asked for more and more and more features that are very specific to their enterprise. And it just makes the system untenable and unwieldy.

Matt DeCoursey 45:57
Everybody else to Salesforce, and you know you out while I’m in Kansas City, I used to live in Indianapolis, that’s where I met my wife, that’s where the million dollar bedroom was. But that’s where Salesforce has a tower. There. And you know, and like, the thing, you have your own high res and that’s the biggest building in the city and all that, you know, it’s just like, No, but that’s the thing. That’s the whole point is there’s just like this, like, I mean, I open up Salesforce. And I’m like, What the fuck? Like, how do I do this?

Phil Reynolds 46:27
Do you know that in Salesforce?

Matt DeCoursey 46:31
If you turn a lead into, you know, I don’t, I literally spent 10 minutes on that thing.

Phil Reynolds 46:36
And I was like, no, the data model is incoherent. It really is. It’s just rough. But anyway, so So I believe there’s a ton of opportunity for entrepreneurs in many, many enterprise software segments, where there’s some established leader that’s been out there for 20 years, 30 years doing their thing. And they have created so much feature bloat. And or even worse, they’ve been acquired two or three times by a private equity firm and maybe gobbled up by a bigger private equity firm. And now everything’s run on a margin. And there’s 45 million features in the licensing fees that are absurd. And it’s overweight, and it’s horrible to use them. It’s slow shit. And all you want is something that does the thing you need to do. So my whole career has been going in and looking at verticals in this case in depth tries universe, agile software teams, what does an actual software team need? What do they need the system to do? Let’s go have it do that. And only that, and exactly that. And let’s do that. And I’m not trying to be a system for, you know, manufacturing or for travel companies. I like it, it is Project Portfolio Management specifically for agile software teams. And so we just make all these decisions. And all these workflows just baked right in. So there’s no admin, there’s no like huge permissioning schemes and all make it all function and set the thing up in a couple of hours. And everyone I show it to is like, oh my god, I love this. But of course, over time, the call has the bigger customer and the more features will always come from me too. And eventually you need to show investor return and all those things. And so there’s a real challenge for you know, entrepreneurs and figuring out, how do I build something compelling, lightweight, nimble, that then doesn’t suck? Like how do I? How does 10 years from now not suck?

Matt DeCoursey 48:20
Well, I mean, I think you’ve got a lot of good points, and you’ll probably go for another hour on that. I don’t know, man, I gotta say like, when I, we got to kind of as we kind of wind down the episode and I look at, you know, I, like I mentioned gravity with the pitch deck, like, I mean, and I’m really just trying to simplify things. I want to take steps out of everything I do, anytime, every time. How can I reduce the number of steps? How can I have I don’t know, man, clarify explanation, because you because, you know, they’re one of the simplest ways to compare the complexity of what you’re doing. There’s just a simple formula of talking about all you take the number of steps, you multiply it times yourself at your score. So if you let’s say, let’s start with, let’s sex isn’t easy, six times 636. Okay, three times three is nine. It’s actually four times harder to implement a six step process and you know, four times less likely to get people to actually do it or complete it. And that’s three steps, like but that’s a big, big, big difference in results. And that’s how important simplicity is to my patient. What about what about, what about a two step process? Right, right. So now now, that’s nine times harder, nine times harder for just a few more steps and you get back into that like back to the pitch deck, and are all of it like the more the more you get people to think about and the thing that was my mind and frustrates me on a remarkable number of days is just how bad people are following instructions.

Phil Reynolds 50:01
I mean, there’s a reason that Amazon has rapidly moved to our world where you can just click one button and it comes to we’re going, we’re all overloaded man, like, we’re hit by our phones and by every, you know, admirals following us around and every social platform and I mean, like, like, we’re all overloaded. And it’s, it’s true. On the wrist thing in our, in my dev stride pitch deck. One of the big money slides in there was, I show the aggregate probability of success and how it diminishes count within each handoff step, you only have a 2%.

Matt DeCoursey 50:25
It’s a similar thing. Yeah, I mean, it’s a similar thing over like, the scientific and scientific accuracy, because honestly, I will, I will say that it’s kind of like the Pareto principle, the 8020 rule, I can probably shape that to be about however I want you to. But for better general, as a general metric, I mean, that is it, I find that what I described in the, with the steps and all that really is true, like in so many things in life, and, and it’s like, I don’t know, man, I just try to think if you so I’ve mentioned row one. So is this annoying? Rule two, I call five or 75? Can a five year old or a 75 year old figure out how to use whatever you’re building? Yeah. Oh, that’s a great rule. I mean, cuz some of that’s like, you know, that that’s a good point. Because is it simple enough and intuitive enough? And, I mean, I think that’s the thing that, you know, I’ve, I’ve seen so much software, and so many things finally move towards, you know, everything from E commerce purchases, like how many how many sales did your ecommerce business miss, because you don’t have buy as a guest, because I don’t want to fill out another form. All right. So here we are, we’re, we’re, we’re, we’re approaching the landing pad here, I did a couple things I give any founder they offered, I like to end my episodes with what I call the founders freestyle, and give and give you a mic. And you can do whatever you want. With it, I got a couple of things that I know that I wanted to point out about that came out today that I thought were pretty impactful. So with that, it’s your chance to say whatever you want. And you can see we’ve had people saying rap and not you might actually take us up on that.

Phil Reynolds 52:18
You need to have been sitting here drinking bourbon this whole time.

Matt DeCoursey 52:21
Yeah, we are not drinking bourbon here. No, no, no, not yet.

Phil Reynolds 52:28
Yeah, so that man, there are so many things that I have come to know, for myself in the world. And I’ll say this, I’ll use my time. I think probably a lot of people use this time to pitch their company. Their strengths, cool.

Matt DeCoursey 52:43
It’s awesome. A lot of times, it’s just shit. Yeah. But they’re like, wow, this went fast. I forgot to say. Yeah, I was gonna say I’m gonna go a different direction with it.

Phil Reynolds 52:49
So obviously, you should use their stride if you’re an agile Dev, and he’s what you said, is awesome. But actually, I think it’s much more important to say, if you’re founder, and you’re out there, your job is hard, you are tired, and you are worn out, and you’ve got a million things against you. But I mean, both of us sitting here at this table are proof that if you stick with it, and you’re nimble, and you just are honest with yourself about what’s working, what’s not working, you keep innovating. You’ll make it to the other side, just have to stay with it. Don’t let those dark days pass. Like you know, when you lose a sale, you thought you’re gonna get or somebody you know, some employees mad about something, don’t let that take your eye off the ball. Like, it’s up to you like you are the heart, you’re the soul, you’re the thing that keeps the company moving. I keep your eye on that, be the soul, be the spirit of the company. And just keep driving, drive, drive, drive, drive, always drive like every morning, keep driving. And if there’s one thing until ready, just just keep at it.

Matt DeCoursey 53:53
Well, it’s amazing who said that, because actually what I had for my freestyle was. So for those of you that aren’t aware, I recorded six podcasts in two days with some of our top Kansas City startups. And I’ve been to three today, this is the third one. Now, earlier today, I was in here with Toby rush, who’s a very well known founder here in Kansas, to build successful exits, and use the same word that he used earlier, because he’s talking about why it’s important to have conviction, conviction equals passion, and some of that and that’s that keep driving. And that was literally what I wanted to bring in. Because I think that talking about what’s your advice or input when you’ve done it a couple of times? Well, you’ll see me and the videos we publish online or any of that if you’re not passionate about the business that you’re thinking about starting getting involved with, and Phil’s looking at me and shaking his head, because don’t do it. Don’t do it because you’re gonna quit. Yeah, you will 100% Quit. It’s harder than you think. You will quit. It’s the passion and conviction. I usually describe it as passion more so than the word convexity. So when I think about conviction, I think about going to jail, maybe I’m trying to avoid that to try to avoid quitting the startup or getting convicted. No, but, but that passion is that driver because you really do. I would give this advice to so many entrepreneurs like you have to be able to; that’s the thing that’s gonna drive you through the hard moments. And it is, and it is like, it really is a Yo yo, and dude, here’s the thing, it doesn’t matter if you have a bunch of money in the bank, and you’re going back and doing it again, because you’re gonna go through the same thing, close that off with a personal story.

Phil Reynolds 55:38
As you know, I did exit my last company. And one of the things that are kind of cool, and a lot of people don’t get to experience this is I had a 20-year career running a company and doing all the things we just talked about the last little bit here. And when you finally retire and step out, it’s, in some ways, it’s kind of like going to your own funeral. People have an opportunity to tell you all the nice things that they never tell you day to day, and I got to have this really amazing folder in my email inbox that I still save. And I probably got 200 personal messages and stories of just like, you know, we hired people from all over the world, out of sane situations, you know, help people go from, you know, I grew up, you know, out in rural Missouri somewhere and then now I’m, you know, making 20 $30,000 a year as a VP of engineering or whatever you would have bought it. And it was just an opportunity to feel amazing about what we had been able to accomplish over the timeframe. And so on those hard days. Like, I just haven’t done it. It is so worth it. Oh, yeah. In the end. Yeah. Like, like, you’re changing people’s lives.

Matt DeCoursey 56:50
Oh, dude. I’ve told people about Misery. And they’re like, Well, why do you do it? But it’s that, and that’s the thing is, and you know, the main, so you look at Startup Hustle. And before you even published an episode, I made a promo video that was kind of like a slow pan on a lemonade stand and talked about how a lot of us are entrepreneurs. I’m getting goosebumps again about entrepreneurs and, like, you know, and how we feel, that’s what we need to do. But your goal needs to be to build something bigger than you know. At least, I recommend it. And you know, that’s not always what entrepreneurship looks like for a bunch of people. But with that, the feeling of getting it right and having it’s like it’s almost amazing. I mean, it really is, and it’s I don’t think even it’s hard to describe, and the best thing that is a comparison is literally Maslow’s hierarchy of needs. And that fifth little thing is self-actualization very. What does that mean? That means that you’re doing the things that you knew you were always capable of. And it’s a maximization that is, that is a very indescribable feeling, really, I mean, I mean, I, I, I’m sitting here like what code described it as like, now, I’m going to kill my credibility maybe. Yes, I’ve tried drugs before. They weren’t as good. No, they weren’t, as you know, that was the best thing. The best thing is. Yeah, yeah. So there’s, there’s a little open transparency. Yes. Being successful as an entrepreneur is way better than drugs. I’m ending this episode now, and I’m out.