Ep. 279 – Ben McDougal, Author of You Don’t Need This Book on Startups, 1 Million Cups & Techstars

Ep. 279 – Ben McDougal, Author of You Don’t Need This Book on Startups, 1 Million Cups & Techstars

On this week’s episode of Inside Outside Innovation, we sit down with Ben McDougal, Author of You Don’t Need This Book: Entrepreneurship in the Connected Era. Ben and I talk about his portfolio-based career in entrepreneurship from founder to 1 Million Cups organizer, to his current role as entrepreneur In residence and ecosystem developer with Techstars Iowa. Let’s get started.

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Interview Transcript with Ben McDougal, Author of You Don’t Need This Book

Ben McDougal, Author of You Don't Need This Book: Entrepreneurship in the Connected EraBrian Ardinger: Welcome to another episode of Inside Outside Innovation. I’m your host, Brian Ardinger. And as always, we have another amazing guest. Today we have Ben McDougal. He is author of the new book, You Don’t Need This Book: Entrepreneurship and the Connected Era. Welcome to the show. Ben.

Ben McDougal: Thanks, Brian. It’s great to catch up with a friend and looking forward to connecting with your audience.

Brian Ardinger: Absolutely. You and I have known each other for a number of years in the startup ecosystem building world. You hang out in Iowa. And I hang out here in Nebraska. It’s been fun to see your journey. You joined Techstars Iowa as kind of a hybrid role as an entrepreneur residence and ecosystem development person. So how did you get involved in startup ecosystem development?

Ben McDougal: Thanks, Brian. Yeah, I’ve always been an entrepreneur. I came out of school, admittedly, thinking that we got expensive pieces of paper to go build someone else’s dream. But startup, wasn’t a word back in 2004. I got a computer science degree wanting to develop video games.

Ben McDougal, Author of You Don't Need This Book: Entrepreneurship in the Connected EraAnd so looked at that industry. Which led me to web development. When I look back at it, it was pretty entrepreneurial. I mean, talking with endless different industries on how to build their business online. And so, while I was in somewhat of a traditional kind of business development role. I don’t know what spawned the entrepreneurial spirit besides just recognizing an opportunity.

So, I created a 3v3 soccer tournament. I had played soccer. I was in a web development shop and could make a nice live event come to life. Ended up having two years of that before selling it to a local soccer club, as we had launched a social network for gamers. It was interesting looking back using entrepreneurship to wedge myself into an industry I was always passionate about. But there’s a whole community side that was emerging.

And so built Jet Set Studio. It’s still a small sliver of my career portfolio. Doing video game events around North America and building community in person and online. That was some of the early interactions of community building. I would stay in web development for eight years and retire out of that and go into another kind of traditional role inside the home building industry. Never really touched a hammer and kind of avoid manual labor, genuine.

In that home building world, we found a disconnect between Home Builders and Realtors. So, we built an open house scheduler, knowing that it’s not hard, but it’s recurring when they’re connecting that open house schedule. So that’s Open Open. Alongside of that, that intrapreneurial spirit was fed with that parallel entrepreneurial spirit ended up building Flight Bright in the craft beer industry, which was an electronic beer flight paddle.

It translated and continues to be that type of electronic serving system. But we added a beer festival app. And so that’s Flight Bright and that story continues to be written. You think about this diversified career portfolio that has a mixture of entrepreneurial and intrapreneurial activities. And the glue that brings it all together, along with myself is the community. Leaning into community and recognizing the energy of accelerating others.

And so that’s where you see my work in 1 Million Cups long ago. Like I was a part of a 1 Million Cups every Wednesday as an entrepreneur. But when the opportunity to lead emerged, I rose my hand. Got involved. That led to the chance of being a regional rep. So, we built this role to help support all of the different organizing teams across the United States.

And so, I’ve been the Midwest regional rep now for the last four years. And that has been remarkable. Supporting and connecting 45 different 1 MC communities across 12 states, has created an awareness when it comes to entrepreneurial ecosystem building, at a rural, medium, and large size environment.

Brian Ardinger: Absolutely. 1 Million Cups. I’ve mentioned this on the program, a number of different times, and I know a lot of people in the entrepreneurial startup side have maybe heard of 1 Million Cups. But on our corporate innovator side, it’s, it’s one of those programs that I think that more corporate innovators should become involved and that.

Maybe give a little bit of background about 1 Million Cups and why that’s so important, not only for the entrepreneurs in your community, but the companies and the other organizations.

Ben McDougal: I think intrapreneurship at existing companies, small, medium, and large is a critical component to any entrepreneurial ecosystem. Having employees that are the champions of change for their existing company, plugging into community activities, helps them stay in front of the innovation curve. Fuels like their innovative energy. And creates opportunities to collaborate with entrepreneurs that in a way that helps their companies.

And so, whether it’s the energy. Kind of the network and human capital that can come from this type of active. All the way over to the financial capital and opportunities for those companies to benefit from their interactions with startups is real. One quick tactic, Brian, that catches my attention is larger companies treating activity within a startup community as volunteer hours.

So, removing the barrier of PTO for someone who wants to go to 1 Million Cups on a Wednesday morning. Or to that startup event. Instead of restricting that type of activity by saying they need to take time off. It’s celebrating that activity, knowing that while it’s a little less time outside of the office, the energy, the activity, the connections, the progress that has made through that activity, benefits the company, perhaps even more. There’s some value when you think about giving intrapreneurs, the freedom to explore their curiosity.

Brian Ardinger: Absolutely. And that’s one of the things that we talk about a lot is not only entrepreneurs have to get out of the building, but intrapreneurs as well. And you can’t build anything without actually getting out there and trying things and testing things and being a part of the communities.

We talk about this concept of a portfolio career and more and more folks I believe are going to have to be transitioning to this concept of, you know, you don’t do just one job for 20 years of your life. It’s a series of different side hustles and projects and people you work with and that. As an early adopter to this portfolio career type of lifestyle, what are some hints or suggestions you could make for people trying to transition into more of a portfolio type of approach?

Ben McDougal: Yeah. The Diversified Career Portfolio is something that allows you to use energies from different activities to maximize the outputs. And sometimes that means it’s the full-time job paired with a couple of side hustles. Complemented by some volunteer roles. Knowing that those kind of shapes within that pie chart, that’s how I like to visualize it. Are always changing.

And the interactions between them are something to be conscious of. So they don’t necessarily need to directly connect because they connect through you. And so, recognizing that even if they’re different activities and completely different industries, that passion that you’re feeding translates into good things for other areas within that pie chart.

Another thing to always keep in mind is your personal bandwidth. I write about this in the book, a complete section for side hustles. And knowing that your personal bandwidth is something, if you can do a lot, then everyone’s going to be asking to do a little. You know, and so all of a sudden you can potentially get diluted to mediocrity.

And I think there’s a good exercise of imagining that you have timed to swinging an ax 100 times. With those hundred swings, are you going to hit 100 trees once? Or perhaps a strategic collection, a few more times to make the impact. Knowing that it doesn’t just need to be one tree. You might be able to make a positive impact on a collection of trees with those hundred swings, keeping your eye on that personal bandwidth as you add, or remove things from that career portfolio.

And lastly, I think the value of transparency. There are other things to talk about here but being transparent with the way that you spend your time avoids the exhaustion of secrecy. And so, whether that’s an entrepreneur sharing that side hustle with their boss and exploring that interest. Or it’s easiest from the beginning, right. So, as you bring on a new project or enter a new contract, being very clear with the way that you spend your time, so that there’s not tension down the road.

Brian Ardinger: So, Ben, let’s get into the book a little bit. It’s called You Don’t Need This Book: Entrepreneurship and The Connected Era. What made you decide to write a book? And give the audience a little bit of background about what they should expect from it?

Ben McDougal: There was a time where I started to feel a sense of potential regret. I had enjoyed some fun ventures on my own. But really it was the stories from thousands of entrepreneurs that I had interacted with. Whether that was on my own journeys or within 1 Million Cups. And learning from these different perspectives and the activity of so many remarkable entrepreneurs, it became to the point where if I wasn’t able to pass that on to my little one, right. My startup that pays in love that this experiential wisdom would just be lost.

And so that was kind of my why. To synthesize everything that I understood about entrepreneurial. But specifically, within our connected era. Driven by community and the ability to do so much more with less, through the network of a global economy.

And so, I crafted an outline. It sat on my phone for a while, and I was encouraged by Victor Wang to build into it when it started to keep me up at night. And that’s where I had reached. And so crafted the manuscript. Had a beautiful forward by Victor, that explains that moment. But also, a contribution from Brad Feld in the very thick community chapter. Which is number two out of 10. I think it’s such an important piece.

And so, it’s been called a nice guide for first-time founders and entrepreneurial ecosystem builders, exploring that professional field. Whether it’s the ideation process right out of the gate, all the way through to what I would consider a wild card. And that is persistence. And so, you know, marketing is in between research, customer discovery, and like I mentioned, community. So, it’s really provided a strong sense of peace and I’m so thankful for how it’s coming from.

Brian Ardinger: What I liked about the book is a lot of startup books are about the tactics of how do you increase your sales or grow XYZ. Yours brought in not only those tactical aspects, but also the bigger picture of it’s not just about the entrepreneur. It’s about the team they bring together. It’s about the community that they have to support. And that are supporting their efforts. And it gave more of a holistic approach to what it means to be an entrepreneur, rather than just the blocking and tackling of the business side of things.

Ben McDougal: Yeah. The amount of activities as an entrepreneur is kind of like everything, right. So, I talk about the term Career Nirvana. Which is where, you know, your work feels like play to you, but looks like work to others. It is in balance with your community, with the team that you’re working within and with the life that you live. Entrepreneurship is not something that you learn. It’s more of a lifestyle. It’s more something that you just bring into your daily life.

And the practice can be, become something that leads you to maybe the first time that you need to pivot, right. You either succeed or we learn. Not being afraid of failure, knowing that you’re continuously optimizing that career portfolio to have the right slivers in that pie chart. And tweaking the size of each sliver along the way. So, I appreciate that, Brian. It’s definitely fueled from learnings, from people like you. From remarkable entrepreneurs and community builders that have taught me so much.

And it’s been neat to hear their responses. Similar to what you shared. There’s some heart within it that explores the tactics, but also some of the mindsets. Some of the community aspects, that will give you the resiliency to play longterm games with long-term people.

Brian Ardinger: Great advice. You hung out with a ton of entrepreneurs. And you’ve seen them at the earliest stages and that. What are some of the biggest myths about entrepreneurship that you’ve uncovered or things that you wish that early-stage entrepreneurs would know earlier?

Ben McDougal: You’ll see it in the book. I call it the Headline Trap. We see entrepreneurs raising a million here and a kabillion there. Right. We see them in the media and that is a well-deserved and of course, an important recognition of people’s own successes. But that can also become paralyzing for someone who feels as though they’re not allowed to tinker.

The opportunity of a side hustle or a startup, or even a full-time effort, doesn’t always need to rely on financial capital or global impact in order to positively impact your life and your career portfolio. And so, giving the permission, that’s not required, but sometimes needed in order for people to explore their passions. Without the weight of feeling like this has to have this huge global impact to make it something that really provides purpose and provides a sense of gratitude with someone’s career portfolio. The way that they spend the limited time. And so, I think the Headline Trap and avoiding that is one way to get started now, instead of like the dreaded someday.

Brian Ardinger: Yeah. Trying to line up the perfect plan and then launching the perfect plan is never the perfect way to make it happen. I mean, the plan is never going to be perfect from day one. You’ve got to go out and stub your toe and figure it out most of the time. You don’t seem to have much fear from the standpoint of, you’re always willing to try something. Swing a different bat. What gives you the confidence to do that? Or what have you learned that gives you confidence to step out in the unknown and try something different?

Ben McDougal: I don’t know if there’s one thing that would be like, this is how I have become confident. I think it’s a mixture of having stepped out and it doesn’t hurt. It’s exciting. You know, the enthusiasm of building something that you care about. And that can lead to the resiliency we’ve spoken about. You know, I think there would also be a collection of skills that give me confidence. And I write about that in the marketing chapter of You Don’t Need This Book. Because it makes us dangerous as individuals.

Linebacker doesn’t play wide receiver. Right? So, recognizing your role. What you’re good at and filling the gaps so that you’re not cloning yourself when you’re building as a team. Or working with contractors as lone wolf. But there are six skills that I think have given me a lot of confidence and abilities to build on my own, knowing that adding more fuel to the fire along the way is always possible.

I start with writing. I think writing is a powerful skill that you can learn just by doing. Also I think of photography. Videography, not just taking the videos, but being able to stitch things together so that it’s digestible and tells a story that connects to a broader narrative. Graphic design. Right? Bringing all those multimedia things together.

Creativity, knowing that everyone can take a photo, but it’s that angle or it’s that ability to publish, is what separates with that creativity. Organization is another one that comes to mind and knowing that as you collect this mountain of media, being able to keep track of all of it in a good way is another valuable skill set.

And then lastly, when it comes to content creation is just bringing it all together and recognizing that there’s a practice in staying creative and building the content. So that you can create stories that sell and having the ability to do that on your own allows you to do a lot with a little, even if you don’t plan to do all of it hands-on. You’ll recognize what needs to be done for whatever the project is next.

Brian Ardinger: You’ve been around in the Midwest Startup Ecosystem since the early days. You know, a lot of stuff that’s happened in Iowa has gotten a lot of traction over the last four or five, six years. And now you’re involved with Techstars and that. What are some of the trends that you’re seeing when it comes to startups in the Midwest? And what are you most looking forward to?

Ben McDougal: Yeah, so the Techstars role emerged from that community building that we talked about earlier. And I was already an entrepreneurial ecosystem builder. So, when there was some room to get involved with the accelerator, I jumped at the opportunity to partner up with Techstars. And leaned into that Entrepreneur in Residence role paired with Ecosystem Development.

So while I’d always admired Techstars, this was a cool kind of side door to sneak into the rocket ship that is Techstars. And so, when you see these founders coming in, wherever they’re from, and you start to think about the Midwest entrepreneur, I think that we could talk about things that everyone always talks about.

Right. We don’t have quite the access to people that are interested in getting risky with their financial capital. We can talk about some of the resources that may or may not be the same as some of the larger hubs like Boston or San Fran or some of the other ecosystems. But one of the things I find liberating is using a framework that we see in the Startup Community Way, by Brad Feld and Ian Hathaway, the Seven Capitals.

And releasing ourselves from thinking that we have to have money. Okay. What do you have? Right. It’s that abundance mindset and leaning into that holistic kind of positive sum approach to entrepreneurial ecosystem building. Allows us to use what we have to attract more of what we want.

And so, I see a lot of entrepreneurs almost being set free. To think big. To build something that can be scalable. Not being afraid to tinker and fail, right. But also knowing that it’s going to be a process. And one of the easiest things that I would say we have in the Midwest is almost natural. Give first mindset. Without preconception or without alternative motives.

When I talk to someone, I almost have immediate, almost natural, positive, intent. That I want to see you succeed. That type of give first positive sum. If you win, we win approach is prevalent around the Midwest. And it allows us to do more with less through the connected era.

And so, while there might be less of certain types of capital, in some cases, there are also more types of capital in the Midwest that allows people in rural, medium communities, and even the larger cities that we have throughout our Midwest region. Knowing that we can connect to the global community and make an impact no matter where we’re at.

Brian Ardinger: Yeah, I think it’s so important and we see it every day. And you guys sent a message to some of the folks here in Lincoln saying, hey, we want to come out with Techstars to promote the fact that our applications are open. Can you set up some meetings and that? And you guys came out last week and toured some of our ecosystem.

We’ve done that back and forth over the years. It’s nice to have an ability and an environment that fosters that type of relationship that it’s not just about keeping everything in my own backyard.

Ben McDougal: It’s still inviting. Cheers to that group that we enjoyed time with there in Omaha and also in Lincoln. And that type of interaction, like you said, is not uncommon. A couple of friends who want to show you around leads to an entire day of inspired activity. In fact, not knowing when you’re listening to this, but our applications oddly enough, open today, Brian.

And so, if you are building a team. You’ve got this startup and you’re ready to scale. I did not come onto the conversation, planning to promote such a thing, but the applications are open and the Techstars experience is remarkable. It’s really geared towards those who are looking to scale up. Maybe looking to raise venture capital in order to support a growing system. And the amount of mentors at a global level. The amount of give first and kind of Techstars for life. That culture is real.

And our hybrid program allows folks to participate in Des Moines, Iowa, but also online throughout the hundred-day program. And boy seeing these entrepreneurs and their teams, and their companies emerge and raising serious capital and going on to continue to do big things is another way that I’ve energized my own career portfolio. Because I’ll say it again, folks. The energy of accelerating others is unmatched.

For More Information

Brian Ardinger: Absolutely. I appreciate you coming on Inside Outside Innovation to share your enthusiasm and acceleration path. If people want to find out more about yourself or the book, what’s the best way to do that?

Ben McDougal: It’s very easy. Benmcdougal.com. Has my activity throughout the social media landscape, but also has my weekly writings that are called Roasted Reflections. And there’s a quick link to take a look at the book, whether that’s in the signed soft cover format or the e-book, or most recently released the audio book that I narrated. And so, you can enjoy You Don’t Need This Book and I’d love to hear what you think.

Brian Ardinger: Excellent. Well, Ben, thanks for coming on the show again. Looking forward to continuing the relationship and seeing you out there on the field as well. And I appreciate you coming on the show.

Ben McDougal: Hey, may the best of your today’s be the worst of your tomorrows and keep building.

Brian Ardinger: That’s it for another episode of Inside Outside Innovation. If you want to learn more about our team, our content, our services, check out InsideOutside.io or follow us on Twitter @theIOpodcast or @Ardinger. Until next time, go out and innovate.


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Episode 279

Ep. 279 – Ben McDougal, ...