What My First Business Taught Me About Failure

It was just one step on a longer journey

When I was a junior at the University of Maryland in 2007, I took a class that altered the course my life.

I was majoring in mechanical engineering, destined for a career in project management when a business professor opened the door to an alternative choice. He told me and my classmates that life is not about following a path. It’s about creating one.

That moment set into motion a story line in my life that led to my first business, a passion and career in entrepreneurship, and the confidence and skills to create agency and purpose in my life.


Last week, I sat down with two of my former classmates — Allie Armitage, an emotional intelligence facilitator and coach — and Vlad Tchompalov, a software developer and UX (user experience) designer. We’re now close friends, but we met in that business class in 2007, and along with our friend Yasha, turned our class project into a company called weBike.

I wanted to reflect with Allie and Vlad on how starting weBike shaped their views of entrepreneurship and how those views have evolved since. I wanted to know which lessons were lasting, what business advice didn’t pan out, and what impact weBike has had on their lives and careers since its closure in 2012.


From Class Project to Budding Business

If you’ve seen the roaming fleets of bikes and scooters for rent that have taken over most major cities in the US, you have a pretty good idea of what weBike pioneered over a decade ago. But our idea didn’t start out that way. At first we simply wanted a better way to get around our sprawling college campus, and we looked to the of bike sharing systems in Europe for inspiration.

I wanted to know from Allie and Vlad what it was about our school project that motivated them to pursue it beyond the classroom.

“Our professor, Dr. Gerald Suarez, was the differentiator that separated that project from every other experience I had in school.” Vlad shared.

“Suarez taught us how to think. He told us that in five years, our grades wouldn’t matter. That when we graduate, there wouldn’t be a rubric or a guideline for how to live your life. We’d have to figure it out for ourselves.

“He challenged us to go out into the world to find a problem we wanted to solve, and work on it during the semester. That’s how weBike was born.”

The weBike team — left to right: Brad Eisenberg, Vlad Tchompalov, Yasha Portnoy, Gerald Suarez, Allie Armitage

The weBike team — left to right: Brad Eisenberg, Vlad Tchompalov, Yasha Portnoy, Gerald Suarez, Allie Armitage

I wondered, was there a moment they felt that weBike made the transition from class project into business? Allie responded. “There wasn’t one moment. The seeds were planted with the amount of momentum we were able to create by the end of the class.

“Our passion was a source of fuel for us. We shared our ideas often and loudly with friends, other students, and university leadership. The more we talked about weBike, the more the energy behind the project intensified until the momentum grew to a point where it didn’t make sense not to pursue it beyond the classroom.”

You Can’t Be Taught Real World Experience

With the support of Dr. Suarez and motivated by the feedback we were receiving, we decided to take the plunge.

“We didn’t really know what we were doing, but we had the belief that we could figure it out,” Vlad said.

  • We met at nights and on weekends honing the design of the system.

  • We performed surveys and focus groups with over 1,000 students.

  • We scheduled meetings with every administrator and university stakeholder we could to pitch our idea to.

  • We talked to tooling shops to figure out what it would take to develop a bike station.

  • We took entrepreneurship classes and wrote a business plan.

We followed every step from the “playbook” of how to start a business. But we weren’t making any progress. People told us they loved the idea, but nobody was willing to take action.

“I remember six months or more of frustration trying to pitch the university,” Allie recalled. “So we went back to Dr. Suarez, heartbroken, not knowing what to do. He sat us down and reminded us about using design to remove challenges.

“Suarez asked us, ‘If the stations are your biggest obstacle, what would happen if you removed the stations from your design?’” The shift in perspective was the breakthrough we needed.

We Pivoted Before We Knew What a Pivot Was

We pivoted to a dockless model that removed the need for the expensive stations that were holding us back. We realized we could buy some combination bike locks and rent out the bikes through text messaging.

The weBike Beta Fleet

The weBike Beta Fleet


With a $2,000 grant that we won at a pitch competition on campus, we built our beta program. Vlad and Yasha wrote the software that automated the rental process. We partnered with a community bike shop to buy and refurbish a bunch of abandoned and beat up bikes. We outfitted them with bike locks and homemade wheel inserts. Then we released the fleet on campus.

We learned from that experience that it’s not the resources you have that matters. It’s your resourcefulness.
— Vlad, quoting Tony Robbins

The beta program was a huge success. We landed on the front page of the Diamondback, The University of Maryland’s student newspaper. We were featured in local media, on MTV-U, and in major press outlets like the Huffington Post and Washington Post.

From the weBike Cover Story in The Diamondback

From the weBike Cover Story in The Diamondback

“It gives me goosebumps,” Vlad shared remembering the moment the Diamondback article came out.

The recognition paid off. A new apartment building had just completed construction in College Park when their Property Manager read that same article in the Diamondback. Thinking it would be a great amenity for her residents who commuted to campus, she reached out to us and became our first customer.

An Idea is Not a Business Model

Selling is one thing, but sustaining a business is another. As proud as we were of our early successes, it wasn’t enough to keep us going after five years of hustling without a paycheck. We chose to close the business at the end of 2012 and move onto new endeavors.

I asked Allie and Vlad if there was anything they wish we had done differently.

“We pivoted to a great idea,” Allie responded, “but we weren’t successful at finding a great business model.”

“We had so much resistance trying to sell to the universities when the strongest interest always came from the students. I think there could have been a different model selling directly to riders, but we ran out of bandwidth before we realized it.”

Vlad agreed. “I wish we knew not just how to create a business, but how to run one.”

weBike’s Impact is Still Being Felt

Wrapping up our conversation, I asked Allie and Vlad what lasting impact they think weBike left on them that they’ve taken through the rest of their careers.

“It’s given me perspective,” Vlad answered. “I can look at those around me in my life now and see the people who are afraid to try things. I scuba dive, and people constantly tell me that they could never do that. But what they’re really saying is, ‘I think you’re crazy for doing that.’

“But that’s what separates entrepreneurs from others. Entrepreneurship is being able to envision something that’s better than today and having the courage to find out if you can make it a reality.”

Allie responded, “weBike is fundamentally a part of me even though I don’t think about it on a daily basis. The learning I gained from pursuing weBike for five years… I can’t put the weight or words to it. We may have fumbled our way through the first time, but we’ve all come out on the other side successful professionals because of it.

“The result of weBike wasn’t something pretty you tie up in a bow. It was a richness of experience.”

Brad Eisenberg