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Lessons in failure: 7 innovators share hard-earned wisdom at BIW’s Fail Fest

Squadra Ventures COO Margaret Roth Falzon recaps the insights and advice that founders shared during the session she organized for Baltimore Innovation Week 2022.

Participants in the Fail Fest session during Baltimore Innovation Week 2022. (Courtesy photo)
Full disclosure: This is a guest post by Margaret Roth Falzon, the COO of Baltimore-based, early-stage venture capital firm Squadra Ventures. It covers a panel she organized for Baltimore Innovation Week, which takes place this week at ETC Baltimore. BIW was previously organized by, which now serves as the event's media partner.

Every entrepreneur has heard the stat: 90% of startups fail, 10% of startups fail within the first year. The stat less acknowledged, because it’s much harder to talk about, is that 100% of everyone who has ever had a good idea or done a hard thing has had a failure.

Back from the Baltimore Innovation Week archives, this year’s Fail Fest brought seven innovators to the stage to tell the story of a time they failed and what they learned from it.

Each of the stories shared came in the form of a transformative situation. Some were big, others were small, but each one offered a lesson that massively impacted how these entrepreneurs were thinking, how they were problem-solving and, ultimately, how they now make decisions. While told with honest, light-hearted flair on the microphone, these innovators bared the real truth with the audience.

Here’s a collection of gems from these hard-earned lessons:

  • “Find advisors you really trust and show them your whole deck — show them everything. They can’t give you great advice if you’re not sharing with them the information they need to help you.” — Rob Wray, founder of Whitebox
  • “It’s up to you to know what you are capable of, and that you can delegate what you are not. And use your calendar and a project management tool. The world is not over when you fail unless you decide it to be.” — Ana Rodney, founder of MOMCares
  • “We live in a society where people expect us to be on all the time. In an effort to be on all the time, we feel like we have to respond all the time, and so we move at the speed of chaos. But, relationships move at the speed of trust. When I broke that trust, I had to slow down.” — Jay Nawachu, CEO of Innovation Works
  • “Our sustainable competitive advantage is that we celebrate failure. In other countries, if you fail, no one will touch you. In America, that’s part of learning to live through adversity. That’s a checkmark for upside and our markets are built to sustain that.” — Chip Gaskins, CFO of Onyx Point
  • “Share bad news early and often. If you can’t sleep, you’ve been up for four sleepless nights, call them. Text them. Right then. If you wait for the board meeting, it’s probably too late and it’s certainly worse than it would have been if you’d picked up the phone.” — John Timken, CFO and head of investor relations of Squadra Ventures
  • “I know now I can’t just jump out into an industry that I don’t know — even when I think I have a great idea and am pretty savvy at it. [There is no replacing] doing the work prior to make sure that I have the connections, I have the resources and I am knowledgeable about what I am getting into, so that people can believe in us and in our product.” — Lashauna Jones, owner and operator of The Sporty Dog
  • “Remember that investors invest in lines and not dots. Every interaction you have with an investor, that’s a dot. The most successful entrepreneurs I see today are sending out newsletters, updates on what they’re building and how they’re doing over time. They’re taking investors out to coffee to make sure they actually invest in their area or vertical, they’re learning about the investor.” — Anne Balduzzi, founder of SameGrain and managing director at TEDCO

From the perspective of this writer — who also happened to be the MC of this event — a key lesson emerged from across the talks: Some failures are massive, some failures feel massive and some failures affect you massively.

Regardless of where you are in your company or your career, remember to think about those moments of failure. That’s the place from where the learning, the changing, the growing and, eventually, the winning will come.

This event was hosted jointly by Innovation Works and Squadra Ventures through their recently announced partnership. For the two organizations, each of which provides in-depth mentorship and guidance to entrepreneurs in which they invest, this event is just the first example of the kind of community-based startup and leadership development programming that they plan to host together.

If you missed the Monday event in person, you can see it in the livestream of that day’s sessions below (Fail Fest starts at 6:12:37):

Companies: Squadra Ventures / Innovation Works (Baltimore)

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