These VCs started a podcast to share the unvarnished stories of entrepreneurship in the Baltimore-DC area

Working in VC around the Baltimore-D.C. area over the last couple years, Mike Ravenscroft and Mike Leffer crossed paths often at entrepreneurial events. So inevitably they found themselves comparing notes. Eventually, one commonality rose to the fore.

“The thing that I found and that Mike found that we agreed upon was that the most interesting conversations that we had in a given day tended to be with a founder,” said Ravenscroft, who is currently a venture associate working with the angel network at the University of Maryland’s Dingman Center for Entrepreneurship in College Park, and has had stints with C5 Capital in D.C. and Northern Virginia’s CIT Gap Funds.

It could be a minute spent talking about getting a customer or a deep dive into a funding round.

“We found that there were so many of these stories that were accumulating that we were then resharing with our friends because we thought they were good stories,” Ravenscroft said. “It seemed like a really interesting place to start to think about — what does it actually take to build a business?”

The two Mikes also found a more tactical idea they had in common: Both thought starting a podcast would be a great way to surface the stories of these founders. Like most ventures, it percolated for a while. But this year, with a midseason shift to remote interviews due to the pandemic, they launched the podcast “Extreme Uncertainty.” So far, published episodes include interviews with Nick Culbertson of Fells Point-based healthcare analytics company Protenus, Matthew Bjonerud of Mount Vernon-based fintech company Cerebro Capital and Liza Rodewald of military spouse remote work platform Instant Teams.

Extreme Uncertainty is back with the Accidental Entrepreneur Liza Rodewald CEO of @Instant_Teams!#remotework #startup #entrepreneurship #bootstrap #motivation #innovation https://t.co/V3BuVCZ51S

— Squadra Ventures (@squadra_vc) October 8, 2020

Taking its name from “Lean Startup” author Eric Ries’ definition of entrepreneurship as the act of bringing new products or services to the world “under conditions of extreme uncertainty,” the podcast is rolling out with a season of 15 interviews with founders from the region.

As it came to be, the podcast gained a mission. Leffer, a former Baltimore Angels lead who is now principal with Baltimore-based VC Squadra Ventures, framed this in terms of myths they are looking to dispel: First, to share stories from region that might not be as well known in the wider tech world that’s believed to center on Silicon Valley. Another is to dispel the idea that “startup life is easy and glamorous” that’s perpetuated on social media and TV.

“Most founders we’ve spoken to start their companies because they’ve experienced a pain point themselves that gets so frustrating in their daily life that they make the deliberate choice to leave comfort and go try to solve that problem,” Leffer said. “If we can help future founders get into the game for the right reasons then that’s a big part of why I enjoy doing this.”

As they’ve interviewed founders, the realities behind that reasoning have come more into sharper relief.

On his takeaways for founders so far, Ravenscroft said, “the chances are it’s not going to be glamorous, the chances are it’s going to be a hard slog from start to finish and it’s going to be a lot longer than you think.”

While questions about entrepreneurship can be specific to a founder’s situation, “there are certainly targeted nuggets of information that founders in these ecosystems can take away and tweak the regular methodology and apply it for their use cases,” Leffer said.

And in the midst of a racial justice reckoning, they’ve heard how startups are embracing social movements. In their respective episodes, Bjonerud and Culbertson each talk about the Black Lives Matter movement and how they’ve shifted to build more inclusive culture and hiring. There’s lots to do concerning customers and investors and keeping the business running day to day, and Ravenscroft pointed out that the bias built into the system may lead one to believe that this may not leave room for wider concerns. Yet the interviews show how founders must address justice, as well. After all, they’re building teams of people.

“One of the best learnings I’ve taken away from this is, you don’t need to make excuses as a startup,” Ravenscroft said. “You can build an inclusive, diverse workforce that is addressing the challenges that are implicit in society and culture around you.”