Leaving a stable corporate job to step out on your own? The entrepreneurial spirit is thriving, as evidenced by the significant number of Americans choosing this path. Statistics reveal that more than one out of six Americans have embraced entrepreneurship. In fact, the year 2021 witnessed a historic surge in new startup applications, surpassing numbers from past decades.
Jordan Rogers built his dream career with Nike as a Brand Marketing Director. I worked with Jordan when he was a leader at Nike, and we collaborated to develop the FocusFit Challenge. He now owns his own business as a consultant and speaker, teaching athletes and executives about personal branding, leadership, and creativity. I recently got the chance to sit down with Jordan to talk about his big leap.
Jordan Rogers was a Brand Marketing Director with Nike before taking a leap into entrepreneurship.
Curt Steinhorst (CS): Let’s start with your first dream. What inspired you to pursue a career at Nike, and how did you make that dream a reality?
Jordan Rogers (JR): I grew up obsessed with sports, and the Nike brand was synonymous with sport. Michael Jordan, Bo Jackson, Andre Agassi, Deion Sanders … all Nike athletes, all on my wall. After recovering from addiction and incarceration, I started life over at 22. I reconnected with my mind, body, and spirit, and physical fitness was a HUGE part of my recovery that allowed me to heal. Nike inspired me, almost irrationally, and still does. I sought to inspire others through that same passion and aspiration.
Once I found the dream role I wanted, I spent four years just trying to get in the door. It involved making minimum wage (with a college degree) for two years, volunteering for every sports marketing event I could find, and eventually joining a marketing agency as a brand ambassador. I finally landed the dream job after four years.
And it was a dream. Nike trained me and empowered me with incredible opportunities. I feel like I got a Harvard MBA equivalent in marketing and branding just by absorbing knowledge from the smartest people at one of the best companies.
Jordan Rogers at the NFL draft. For Jordan, working at Nike was a dream. He was afforded incredible ... [+]
CS: Do you have a favorite memory or accomplishment while working at Nike?
JR: One highlight was managing Odell Beckham Jr’s brand within Nike and getting to take him to Paris Fashion Week. We connected with world famous designers like Virgil Abloh and then went to Real Madrid’s facility for an intimate meeting with his idol (lifetime Nike athlete) Cristiano Ronaldo. It was a surreal experience to say the least.
Another highlight was Super Bowl LI, where we spent most of our marketing budget serving the 3rd and 5th Wards of Houston, which was especially gratifying to invest in that community in my home state.
But more than those experiences, the people are what make Nike amazing. The company's dynamic atmosphere is fueled by the presence of brilliant and motivated individuals who share a deep passion for sports and the transformative impact it can have on the world. Those people make Nike an intoxicating environment.
CS: What were some of the challenges or frustrations you faced while working at a large corporate company?
JR: I think inherently in corporate America, there is a disconnect within creative corporate roles. One part of your brain makes you good at connecting with and inspiring people, pushing boundaries and being innovative. The opposite part of your brain is good at managing meetings, schedules, and internal politics. With the complex layers of management at a corporate firm, I found that I spent a lot of time just trying to impress people internally, when my role should have been more focused on inspiring people externally.
CS: Does corporate bureaucracy inhibit creativity or progress?
JR: It can. For example, post-pandemic, most people acknowledged that the marketing team did not always need to be in the office, but the bureaucracy in a large organization dictated that wouldn’t be fair to the sales or accounting teams, so marketing had to fall in line. That’s a challenge that a lot of corporations are facing today. If you’re trying to make it fair for everyone across a large firm, then you lose the ability to empower individual teams. So you create an average that hopefully works across the board, when in reality different teams would excel in different structures.
CS: What was the turning point that made you realize you wanted to leave Nike and start your own business?
JR: It was a three-fold decision for me. The first was prioritizing my family’s well-being. We needed to return to my home state to be closer to family and our community. Nike does really well at corporate wellness and improving the employee experience. But the reality is that having more autonomy and living closer to friends and family affects our lives more than corporate wellness programs can.
Secondly, I looked back over the amazing body of work that I had the privilege of doing over the last 10 years and realized there wasn’t much more that I felt like I needed to accomplish at Nike. I got to work on some of the biggest sporting events in the world with the best athletes and artists. I’ve done national television commercials and been on the sideline of every cool sporting event. But the higher I was promoted, the more meetings I would sit in. As a creative, I fundamentally wanted to produce things. It kept getting harder and harder to do that.
And lastly, when people asked me what the key to my success at Nike was, I often told them it was because I was entrepreneurial. So I had to call my own bluff and give it a shot.
CS: Tell us more about what you are doing now.
JR: I founded a solo consultancy for marketing and brand strategy focused within the NIL space (Name, Image, and Likeness). I help colleges, teams, and NIL collectives teach college athletes about branding and marketing. I host workshops that teach athletes and corporate leaders how to build a brand, and remove some of the mystique surrounding that term.
I believe the best personal brands are built on service. I teach clients how to use their platforms to serve others, and to find a cause that is connected to their story. For example, LeBron James is a great athlete, but his legacy will also be known for his I Promise Foundation, the school he built, the jobs he has created, and the platforms he has developed to serve kids and athletes alike. Naomi Osaka, a four-time Grand Slam winner, is known as much for her tennis victories as for her kindness to opponents, creating boundaries for herself, starting businesses to serve others, and building a school in Haiti connected to her father’s home country.
Lastly, I have some creative projects like making apparel and basketballs, and I am collaborating with a golf company. I love that this shift has allowed me the freedom to explore more creative outlets.
Naomi Osaka, a four-time Grand Slam winner, is known as much for her tennis victories as for her ... [+]
CS: What are some of the tradeoffs between working at a large company like Nike and running your own business?
JR: Health insurance. It is much harder, it’s more expensive, and there is no such thing as paid time off. As an entrepreneur, if I don’t work, I don’t make money. But there is also a good trade off. One aspect I love about being independent is the sense of accountability it brings. In corporate America, the inherent structure often involves numerous decision-makers, which can lead to a fragmented dynamic and mixed messaging. The lack of a singular accountability can strain relationships and hinder progress. Now, the buck starts and stops with me. If something goes wrong, it’s my fault. And if something is great, it’s also my fault. I really welcome that pressure and opportunity. So I will take that trade off every time.
Final thoughts by Curt Steinhorst:
I took the entrepreneurial plunge in 2011 for very similar reasons to Jordan. I have since had hundreds of conversations with others considering the same leap. Jordan’s interview beautifully illustrates my experience — there are incredible benefits, but you must be prepared for its demands. You have more flexibility to take time with your family, and you will pay for every minute you aren’t working. You gain power over your own life, and it is more exhausting, more satisfying, more overwhelming, and more rewarding than you can imagine.
On the other side, corporations need to take into account the underlying desires of individuals when they decide to step out on their own. It's not merely the financial aspects or job security that drive people to leave; rather, it's the yearning for autonomy to make significant decisions, direct their energy towards meaningful endeavors, and be duly recognized for their contributions. It is crucial for leaders to recognize the significance of these needs to avoid the potential loss of exceptional employees to the allure of entrepreneurship.
