Far better is it to dare mighty things, to win glorious triumphs, even though checkered by failure… than to rank with those poor spirits who neither enjoy nor suffer much, because they live in a gray twilight that knows not victory nor defeat. ~ Theodore Roosevelt

Sitting with his millennial sons — Hayden and Harrison — Tim Smith, owner of Detroit-based creative firm Skidmore Studio and author of Dare Mighty Things discusses the book, millennial entrepreneurs and pink bikes.

How did the idea for Dare Mighty Things come to be?

Tim: Just over a year ago Hayden was in my office at Skidmore Studio poking around at the stuff on my desk when he picked up the Wildsam Field Guide: Detroit produced by Taylor Bruce, and started thumbing through it.

Hayden: And I said something like, “It would be great if there was something like this for recent grads to help us map out our futures; find our path.”

Tim: At Skidmore, we were already studying millennials. We had clients that wanted to do a better job reaching them. We were really taking a deep dive to figure out why they were so misunderstood and how to zero in on them.

Skidmore’s research, plus Hayden’s casual remark really distilled everything for me. I had a book outlined within a month. A few more months and I was talking to publishers and then I was off doing interviews. It all came together quickly.


Is the book everything you imagined?

Hayden: It was everything and more.

Harrison: Except the author. I didn’t expect it to be my dad. We bounce ideas like this all the time and they percolate for awhile, but often nothing comes of them.

Hayden: This time I said it and 12 months later I was taking a PDF draft of the book with me on vacation. It was my first real adult vacation with my girlfriend and I couldn’t put it down. I think that’s high praise.

Tim: I have never been more nervous to have anyone read my material. This book was foremost for my boys and I wanted it to be something they could relate to.

The book profiles 11 entrepreneurs, five are from Detroit, and of those, four are women. Is that representative of the Detroit entrepreneurial scene?

 Tim: I think it’s representative of the kind of people that are making their way to finding successful, dream-making opportunities. Often women have a deeper sense of purpose that drives what they are trying to do. I was deliberate about telling stories that hadn’t been heard before. The women’s journeys were way more under-told, more interesting.


What was different about Detroit entrepreneurs versus the ones from the rest of the country?

 Tim: I think I’m biased (as he points to the “Detroit Made” t-shirts he and his sons are wearing), but I really do believe that we are a grittier community. We all get knocked down, but Detroiters get right back up again; we are unstoppable. Do I think that’s part of Detroit’s DNA? Absolutely.


How are millennials misunderstood?

Tim: I don’t think it’s a particularly new story — the generation before wants the current generation to do things “our” way. We don’t understand their relationship with technology and social media. In the workplace, we think they lack focus and loyalty because they don’t aspire to 25-year careers with the same company. We aren’t seeing their new path, as a better way, and honestly, the days of staying at one place for 25 years are gone.

Hayden: I’m only a couple of years into my career as an art director for an ad agency in Pittsburgh, and its engaging work. But I think I can speak for my generation: most aren’t completely fulfilled by their jobs — and that matters. I think many of us have become entrepreneurs or have side projects because we need to have an outlet for things we are passionate about.

I literally own a company called Side Projects that I can use to fulfill some of those dreams. Will it ever become something I do full time? I don’t know, but I love having it available to me.

What do you think is misunderstood about entrepreneurship, and how does your book clarify it?

 Tim: I think in general people believe that you have to be some throw-caution-to-the-wind, rule-breaker, glutton-for-punishment business shark to make it as an entrepreneur. And, that you aren’t successful until you have $100 million of venture capital raised and an IPO on the horizon.

Every entrepreneur has to gather enough courage to step off the edge, but it does not mean you have to blindly jump without a parachute. I wanted to express that there is no one way to be an entrepreneur, that whatever path you take is the right path if it fulfills you and leads to the success you want. Which for the folks in the book wasn’t ever really about the money. Your path is unique and special to you.

Hayden: I also like that the book doesn’t romanticize the process. It is going to be hard work. You have to make sacrifices, you might fail, and all of those things are okay. It is not the end.

Harrison: You can come from any walk of life. You can be a planner or a more analytical kind of person and that does not disqualify you from being an entrepreneur. Look at Hayden with his Side Projects, you don’t even have to do it full time. There are no exclusions, it’s not just for crazy risk-takers.


And what do pink bikes have to do with millennials or entrepreneurship?

Tim: I was 12 years old and I had saved money from my paper route, shoveling snow and babysitting the most difficult kid in the neighborhood. I was ready to buy my own bike, with my own hard-earned money.

I convinced my dad to take me to the Schwinn store in Mt. Clemens, Michigan. Hundreds of bikes were lined up in perfect rows on the store’s sales floor and off in the corner alone was this dust-covered, hot pink, 10-speed bike. I had to have it. I loved the idea that there was only one and that nobody else would have anything like it. I liked the idea that it was different. Neither my dad nor the shop owner could talk me out of it.

I think that’s why I identify with millennials. I’ve always had a desire to go against the grain, challenge convention, be different.


I knew I’d get teased about it, but I also knew that it would be memorable. Whenever someone saw the pink bike — at my job, outside of school, at the drugstore — people knew I was there. That bike got me all the way through high school and most of college at Central Michigan University.

Pink Bike has come to symbolize making bold moves. Writing the book reminded me about my earliest experiences of daring mighty things. It was time for Pink Bike 2.0.

I visited the incredible team at Detroit Bikes and they customized two bikes for me. They hang out at Skidmore Studio for our staff to use and this summer Pink Bike has been getting around town and leaving copies of Dare Mighty Things at terrific reading spots all over the city for would-be entrepreneurs to snap up.

I think pink is the perfect metaphor for being an entrepreneur; you know someone is going to give you shit for making that choice, but you don’t give a shit because you’re content doing your own thing.