J. Kelly Hoey

Driving Into A New Venture: Insights From A Serial Entrepreneur

Brenda Stoner is the founder and “chief good guy” at PICKUP, LLC, an on-demand pickup and delivery service. Yes, she started PICKUP to solve her own problem (moving stuff across town quickly and inexpensively). Solving problems and innovating from need seems to be in Brenda’s DNA — PICKUP is her 7th startup. I met Brenda at The DEC in Dallas (she was a featured panelist at Capital One’s #StartedByHer event), then sat down with her post-event to gain additional entrepreneurial insights from her:

Q: You’ve had 7 startups. What drives or motivates you to start new ventures.

Brenda: I am addicted to the excitement that comes from new thinking and collaboration around a new idea. I thought after the last startup (hard landing) I was ready to hang up the sneakers, then I got the idea for PICKUP. And I stopped sleeping. Seriously, I wake up between 3 and 4 every morning thinking about how to ensure this seedling survives.

Q: Describe your current venture.

Brenda: We engage the services of some of the best guys around, the guys who drive pickup trucks. Many of them are military veterans and firefighters. Knowing we all need to borrow one of those guys and their trucks from time to time, we took that old economy and wrapped some nice tech around it to make it accessible to everyone — guilt free! Making that a perfect experience at a great price is the goal. Then repeat, repeat, repeat.

Q: How has having prior startups helped you launch and scale PICKUP?

Brenda: In some ways it helps not at all because every venture is so different. I guess the best carry-forward (not the tax loss kind, but I have a lot of that, too) is a degree of tolerance to living with complete uncertainly. Uncertainty is a fact of life in new ventures.

Q: Looking back, and knowing what you know now, what advice would you give yourself at the launch of your first startup?

Brenda: Do it. And don’t ever question doing it. Even if it fails.

Q: Any guidance on handling failure?

Like all things in nature, there are opposing forces. Without dark, we don’t comprehend light. Without failure, success is undefined, everything is mediocre. Recognizing that most things adhere to a normal distribution helps. The centerline in the normal curve is not where people like us aspire to be.

Q: At #StartedByHer, you said “starting is easy, finishing is hard”. What’s different now than when you launched your first startup? What’s easier? Why will growing a company always be challenging or hard?

Brenda: The pure excitement of a new thing eventually softens. As a kid, my dad would get irritated by the number of projects I would start and leave in various states of completion. Staying in the game, staying focused and keeping the energy up during the inevitable cycles is pure hard work. And what defines finishing is also key. Sometimes you don’t get to know until you’re finished.

Q: Another of your great quotes at #StartedByHer was an “obstacle is something you get around”. As someone who has bootstrapped 5 ventures, you know outside investment is not the only way to start a business or only resource entrepreneurs need to succeed. With that in mind, what’s your advice to entrepreneurs who are just getting started?

Brenda: It’s great to see all these programs for entrepreneurship in colleges and the encouragement to start new ventures. However, I would not recommend starting something without first having a stint in a legitimate business enterprise. The bigger the better. Starting my career at TI, I learned how systems, people and ethics work together. You can’t shortcut the experience cycle. You just can’t.

Q: Any guidance for entrepreneurs for entrepreneurs on scaling (and getting through the hard stuff to the finish)?

Brenda: I’m still working on that one and looking for daily guidance. The best thing I have come up with is to use (in a good way) the people around you. Success is only gained by leveraging others. So I try to re-engineer my own mindset, skill-set and approach all the time. I always thought you could only change mature people by little bits. I just turned 50. I’ve changed so much in the last year I’m throwing that idea away.

Read more on the Dallas #StartedByHer event in my column on Inc.com.

Thanks to my client Capital One for inviting me to Dallas to cover the #StartedbyHer event and more importantly, for funding the “Breaking Through” study. “Breaking Through” is a publication of the Center for an Urban Future made possible through Capital One’s Future Edge initiative. Capital One’s Future Edge initiative is a $150 million, five-year effort to help more American workers and entrepreneurs succeed in the 21st century economy. Through Future Edge, Capital One works with hundreds of leading community and nonprofit organizations in NYC and beyond, including micro-finance and micro-lending organizations empowering women entrepreneurs such as Grameen America, Accion, and the Business Outreach Center Network. Learn more at www.capitalone.com/investingforgood or join the conversation on Twitter at @YourFutureEdge #StartedByHer


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