Early Stage Founders - How to Deal With the Mental Challenges of Building a Company?

On this week's episode of Inside Outside Innovation, we sit down with Dave Parker, five-time founder, and author of the new book Trajectory: Startup. Dave and I talk about a range of topics for helping founders go from ideation to product market fit. And this conversation was part of our IO Live Series recorded during Startup Week Lincoln. Let's get started. 

Inside Outside Innovation is the podcast to help new innovators navigate what's next. I'm your host, Brian Ardinger, Founder of InsideOutside.io. Each week, we'll give you a front row seat to what it takes to learn, grow, and thrive in today's world of accelerating change and uncertainty. Join us as we explore, engage and experiment with the best and the brightest innovators, entrepreneurs, and pioneering businesses. It's time to get started.

Interview Transcript with Dave Parker, Five-time founder and Author of Trajectory Startup

Brian Ardinger: I wanted to thank our sponsors for this event. We are part of the Techstars Startup Week here in Lincoln. So, we wanted to give a shout out to them and Startup LNK for making this all possible.

Also Inside Outside is sponsored by the Ewing Marion Kauffman Foundation. As many of you may know about the Kauffman Foundation, they run 1 Million Cups and a variety of other things, but they're a private, non-partisan foundation based in Kansas City. They seek to build inclusive prosperity through entrepreneurship- led economic development. 

So, we're super excited to have them as partners with us here. And you can find out more about them at kaufman.org or follow them on Twitter at Kaufman FDN on Facebook or Twitter. So, thank you again to the sponsors. Thank you, Dave, for coming on, we had set this up when your book was coming out and I said Hey, I've got the perfect time to do this during startup week. When we might have some startup founders who may be having some questions. 

You and I met eight or nine years ago through Up Global. We were with Startup America. And you were based in Seattle. You also helped found Code Fellows and you're a five-time founder, so you've got a lot of experience in this particular space. Eight years ago, the startup ecosystem, and what it was like was a little bit different than is today. So, what has been the biggest trends or things that you've seen that it's changed over the course of the few years that we've known each other? 

Dave Parker: Well, let me go a little further back. I started my first company in 98 in Seattle. And believe it or not bill gates and Jeff Bezos weren't really giving back to the startup community at that time. Oh, wait, they haven't yet. I mean, Bill gives back to like global change the world stuff. Right. But the idea there was, wow there's a bunch of us doing this startup thing, but there's not really anybody to give much advice. 

So, we did a peer cohort. Which was my first thing. And after a while I was like, wow, we need to level up our city. All of us tend to think of the next city bigger than us as like, oh, we want to be more like, Seattle doesn't want to be like Vancouver, Canada. We want to be like San Francisco. Where Portland's like, well, we want to be more like Seattle.

Because I grew up in Portland and then moved here to go to college and never went back. First startup in 1988. Built a software distribution company called license online. The company went from zero to 32 million in sales in 4 years. Which was ridiculously fast. And we went from 3 employees to 150 and in four years. And then we sold the company in 2002.

So then in 98 to 2002, if you remember back there, there was a tech bubble in there and there was 9/ 11 in there. So, it was an interesting time. Wasn't a great time to sell a company now, too. But got it sold anyway. And that was my first startup. First of five. Three of them sold. Two of them failed. One in a rather epic crater fashion. Which is funny. Because it was after the first one, that actually worked. 

So, you know, people were like, I wouldn't do this again. And they're like working on the next one? I'm like obviously got a serial glutton for punishment. So, 16 exits total. So as a founder board member advisor. So, my day job is helping companies and founders sell their companies. Which allows me to my 20% time to work on community building and giving back.

Which kind of got me to Startup Weekend and Up Global. Up Global was the merger of Startup America and Startup Weekend. And we did about 1,265 events worldwide, my last full year there, before we sold to Techstars. Including launching Startup Week globally. And we launched it in 26 cities globally, the second year. I ran it in Seattle.

Andrew Hyde started it in Boulder. And we ran it in six cities, the first year. And 26 cities the second year. So, startup communities stuff is awesome. And I love it. It's, as you know, though, it doesn't pay, so you have to have a day job. You have to have a side hustle, so you can keep your community building job, right. Or vice versa.

Brian Ardinger: Exactly. Yeah. I think we're nine years here at the Startup Week in Lincoln. We got grandfathered in when Techstars made it a global deal. But we found it very helpful to have these conversations, even if it's just once a year to get people connected and reengaged with why it's important to have a startup and why a startup ecosystem is so important in your own backyard.

So, you've got a great book out called Trajectory Startup. I would encourage you to take a look at this. There's a lot of books about startups out there. What made you say, I want to take a different take in this and give back to the community by writing a book about startups 

Dave Parker: Two big things about the book gap that I saw in the marketplace is one, I mean, you, you know, Brian, you've been around Startup Weekend. I'd see people coming out of Startup Weekend and they're like, woo. I met my co-founder, Charles. We're going to leave at eight and then go start our start up. And I'm like, yikes. Like, there are some things you can know before you leave your day job and your benefits and all those things, which allow you to really look at what do I want to know so I can de-risk this as the first semester, right. 

So, I got to do the market research and competitive analysis and look how big the market is and like, and how do I do that? The book's really focused on, the original title was Six Month Startup. And then I started delivering it in different formats and I'm like that doesn't work for the brand. So, it became Trajectory Series. 

But the program now is focused on a five-month program that takes you from ideation to revenue. And the idea there is, if you can't get to revenue in six months, it's probably not a great idea. There are exceptions to that rule. Like if you're a B2B or B2B enterprise and you need to build a really robust product, like that's an exception. Or biotech. Or you're doing B to C and you're competing with clubhouse and you're really about growth of users, right? You won't get to revenue in six months. 

But in general, you should be able to validate or invalidate your idea in six months was the goal. The second thing that came out of it, I kind of backed into was somebody came to me during my time at Startup Weekend. And they're like, hey, can I have your fi...