Stephen Wakeling

As a wireless industry entrepreneur, Stephen Wakeling has been developing disruptive, technology-powered services for more than a decade. He holds a BA in Journalism and is an alumnus of Harvard Business School. A journalist by education, a technologist at heart and a gifted entrepreneur, Stephen thrives on start-up culture and has a passion for building things better. He is an avid pilot who has lived across the U.S., Australia and Asia. Stephen currently resides in Atlanta with his wife and two sons.

Where did the idea for Phobio come from?

The idea for Phobio came pretty clearly after I had a bad experience on eBay. I sold an Apple MacBook Pro to fund the purchase of a new computer and the buyer wanted to return it immediately. When it was returned, I opened the box and inside was just a piece of paper. PayPal automatically refunded the account as soon as UPS delivered the empty box and I lost my computer and the proceeds from the sale. When I followed up with Ebay and Paypal they made it very clear that I had been scammed but there was no recourse. After spending an evening considering driving 300 miles to confront the scammer, I decided to build a solution so no one else could fall prey to peer to peer markets.

What does your typical day look like and how do you make it productive?

I schedule my day in 5-minute increments and include everything from eating to working out. I use Omnifocus to ensure that I’m lumping activities together. Typically, I schedule phone calls in the afternoon and meetings that require a lot of my focus in the late morning. Other than that I try to be mindful about keeping big chunks of time open to deal with things that can’t fall within my rigid schedule. I am also conscious about turning everything off so I can be present with my family and making time to spend with my friends.

How do you bring ideas to life?

Through brute force, and trial and error. When neither of these work separately, I try both at the same time.

What’s one trend that excites you?

The broader adoption of working from home/anywhere. I think getting out of my normal routine can be super restorative, and I hope that more people can find their way to take longer trips, blending work and travel in a way that helps them work better and be happier.

What is one habit of yours that makes you more productive as an entrepreneur?

I have a high tolerance for risk when it comes to my team. I like to let people try things even if they’ve never done it before. I think it helps people grow and builds confidence when they succeed and even when they fail.

What advice would you give your younger self?

Simple, I would tell myself one thing: Trust yourself and worry less.

Tell us something that’s true that almost nobody agrees with you on.

Not related to the business, but I do believe that The Silmarillion is J. R. R. Tolkien’s best book. I don’t a lot of people would agree with me on that.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Try things even if you think they may not work. You never know what the outcome will be when your expanding your horizons.

What is one strategy that has helped you grow your business?

Trusting people around me. I think most entrepreneurs are very focused on control and make it hard for their teams to be successful. I probably have the opposite inclination for better or worse.

What is one failure you had as an entrepreneur, and how did you overcome it?

So many failure, I don’t think failing is a big deal. I try to make sure failures are small, that I learn something and that I keep my momentum. I think most people get too precious about ideas and projects.

What is one business idea that you’re willing to give away to our readers?

Sticking with recycling, I’d like to see a more mainstream method of recycling plastics. Between the different types not all of them can be reused and end up in landfills or the ocean. It’s really quite a shame we’re putting so much to waste.

What is the best $100 you recently spent? What and why?

Nothing beats a great pair of headphones. I splurged on an Airpod Max recently and I can’t believe I almost didn’t pull the trigger.

What is one piece of software or a web service that helps you be productive?

The main piece of software I use is Omnifocus. It helps my organize all my actions.

What is the one book that you recommend our community should read and why?

If could recommend one it would have to be Daring Greatly by Brené Brown.

What is your favorite quote?

“Pride costs us more than hunger, thirst, and cold.”
– Thomas Jefferson

Key Learnings:

• Try new things and take risks – it helps you grow and gain confidence when you succeed and even when you fail.
• Trust your team and the people around you.
• Failure is not always a bad thing – learn from your mistakes and continue to push forward.
• Trust yourself and try new things even if you think they may not work.
• Schedule time out of your day to prioritize things you need to do and set aside time to be present with family and friends, that’s important too.