The journey is better together!

Editors Note: This is the first in an eleven-part blog series sharing some behind the scenes moments with each of the profiles in my book, Dare Mighty Things: A Field Guide for Millennial Entrepreneurs!


One of the most enjoyable things for me, during the year-long process of writing my book, was the opportunity to chat with and learn the intimate stories of some truly amazing entrepreneurs. While the book ultimately ended up with 11 profiles, there were so many more people I spoke with along this path who all helped inform the final content, concepts and learnings.

Since the release of the book, I’ve been asked many times about “my favorite” interview or profile. And the honest, although somewhat cliched answer, is that each profile has a favorite moment. I can remember all of the places we met. I close my eyes and recall the sights, sounds and smells of each diner, coffee shop, restaurant, bars and hotel lobby. This got me thinking about sharing some “making of” stories that go along with the profiles in the book. And because I’m going to be in Pittsburgh this weekend, signing some books in Courtney Powell’s store called The Kinsman Shop, I thought it made perfect sense to begin this series with Courtney & Joe.

I was introduced to Courtney and Joe by my son Hayden. Courtney was an employee at the same place Hayden now works in The Flats near downtown Pittsburgh. One day Hayden told me about this woman with a business degree from Penn State who had just quit her job to open a small men’s retail store in an up-and-coming area of Pittsburgh. He shared how her boyfriend, Joe, was also an entrepreneur and how they had a great relationship and support system to help each other succeed.

I found the idea of this relationship between Courtney and Joe incredibly interesting and a unique perspective, and asked if she might be willing to talk about being a part of the book. Courtney and I arranged to chat on the phone first, which I figured would last 5–10 minutes. The call lasted almost an hour while the three of us shared stories, philosophies and insights into the entrepreneurial journey. I remember ending the call and being incredibly impressed with their insights, motivations and personalities. When I finally hung up, I told my wife that they were going to be an amazing addition to the book.

Several weeks later I found myself sitting in a coffee shop in downtown Pittsburgh with this energetic and very impressive couple. I remember the distinct impression that Joe and Courtney enjoyed a very unique and special relationship. Somehow, they picked the lock to the code on how to be both supportive and motivating at the same time. They could challenge and disagree in one moment, and in the very next have a smile and a gentle touch on the hand to demonstrate their emotional connection.

The moments I remember the most about the interview, and the most engaging aspect of the three-hour chat, was how both Courtney and Joe wanted to keep putting the focus on the other partner. It was so clear how proud they were of the other, and how their support and cheerleading was authentic and heart-felt. They would finish each other’s sentences, correct each other with a smile and really seemed to be having a blast with their journey!

As a writer, I often worry that I don’t have the skill to accurately capture on the page those rea; emotional moments of an interview. I worried most about this issue with Courtney and Joe. As I listened back to the tape of the interview and re-read the chapter, I’m still not convinced I did them justice. But I gave it a good shot. Today, Courtney’s shop is doing great by all accounts, and Joe’s on-line fitness experience, Fitt.co, seems to be adding new cities faster that I can keep track! Congrats to them both for Daring Mighty Things together and proving that the weight of the trip is better with two!

Here’s the intro chapter from their profile in the book — page 88.

TL;DR SUMMARY: Joe and Courtney’s paths serendipitously collided in a local Pittsburgh coffee shop in 2012. This chance meeting grew to evolve and form a mutually beneficial relationship and bond that helped each other’s entrepreneurial spirit grow stronger and more complete. Joe, who successfully made the transition from his nine-to-five life as a teacher and found success with his own health and fitness businesses, helped Courtney realize that such an entrepreneurial transition is possible. This is the story of how the teamwork and trust of a couple makes each other stronger and an entrepreneurial dynamic duo.