This Monday at NAPA 2024, Shark Tank icon Daymond John is slated as a keynote speaker.

That prompt sent us down a nostalgic path. Back in 2019, XBE was a newly born startup and was selected to participate in the BGSA’s Shark Tank Competition.

Despite no expectations, we won that competition – and 5 years later – a lot has gone right for our business:

• Truckers on XBE increased by 3521%; Drivers on XBE increased by 1541%; Total shifts managed on XBE increased from 20.3k to 1.3M.
• Expanded in many new markets, now serving over 30 large horizontal construction customers.
• Last week, we announced a significant investment from Banneker Partners, a leading private equity firm specializing in enterprise software.

In the spirit of Shark Tank’s “Where Are They Now?” series, which serves as a post-mortem on successful investment deals struck on the show, we wanted to pose a series of reflective questions to our Founder and CEO Sean Devine to share with the XBE and horizontal construction community.

Building a successful technology startup is often described as a “suicide mission that sometimes goes right.” We thought it would be fun to highlight the good, bad, and ugly of building XBE into the category leading platform it is today.

This post is the first in a series.

Part I – Good Fortune

Q: What would your fortune cookie have read in 2019?

Sean: “See the movie. Live the book.”

I could see what XBE would become and how to get there, but only to the depth and nuance of a movie. And from the outside, that’s probably what others saw too. But, the book - living it - was even better. Full of side quests, characters, and moments.

Q: Luck sometimes plays an outsized role in startup success. What is the single most fortuitous event that happened to XBE over the last five years?

Sean: The COVID-19 pandemic was terrible for the world, but it wasn’t terrible for our business. That’s an uncomfortable truth to wrestle with, incredibly lucky, and something I don’t take for granted.

During COVID, most contractors were deemed essential service providers, and so our customers continued to operate throughout. In addition, the IIJA infrastructure bill passed due to COVID-era feelings about economic stimulus, and that stabilized funding and increased the confidence of contractors to invest in their operations. Granted, there was some related inflation, and that created stress on our customers, but it didn’t last too long and created opportunities for XBE to add value.

In addition, while XBE was always a partially remote team, we went fully remote in 2020. This enabled us to more easily expand our team in India and anywhere else that we could find great talent. Also, my family moved from Chicago to Kansas City during that time, which was great for us personally and put us closer to Superior Bowen which led to some great relationships and collaboration. Finally, the pandemic made everyone (including customers) more comfortable with remote work which enabled us to serve a growing customer base with a small team and limited travel.

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Some of the outstanding members of the XBE team at a recent outing in Goa, India

To be clear, if I had a magic wand, I’d wish COVID away completely, including all of these benefits. I was terribly sick in 2020, as were so many other people during the following years. But, from the perspective of the business, COVID made us stronger, and for that I feel very fortunate.

Q: What other unplanned events changed the trajectory of where XBE is today?

Sean: My leadership and management style at XBE has been heavy on vision and culture, and light on planning. Perhaps that’s a matter of personality, but it was also a good strategy during our formative years.

For that reason, most events were unplanned, though few felt unexpected.

This sounds like an ironic approach for a software company that has pioneered a tremendously effective planning-heavy approach to operations management! But, I think it fits our context. We’re innovators, and we spend much of our time working in the uncertain frontier where heavy planning can limit upside and cause frustration.

Hey Kayla is a great example of this.

For years, we carefully documented new features with release notes, and published newsletters about various business topics. We did this because we believe in the leverage of content, and not because we foresaw the wave of AI innovation that hit in 2022 - 2023. We didn’t have a plan to build a support chatbot like Hey Kayla, but we were prepared to take advantage and agile enough to do so.

That said, things have started to shift. While we still do innovative work for which planning is difficult, our work is generally more predictable than it once was. We’re making plans to plan.

Stay tuned for the next post in the “XBE Five Years Later Series: Part II – The Trough of Despair.”