‘I had to learn to step back’: Lessons in ‘leadershit’ from Founder Factory 2021

How do you deal with a good leadership day versus a challenging one? For at least one Philly founder, it’s the difference of exercise or a drink.

Philly Startup Leaders‘ Founder Factory event returned IRL earlier this month, and about 100 entrepreneurs gathered to share ideas, hear from investors and growth experts, and connect with each other. While most think of these moments as an opportunity to share successes, one of the half-day conference’s sessions was instead focused on failures.

Corporate wellness company On The Goga founder Anna Greenwald led a panel of local founders and leaders on their biggest “leadershit” moments — that’s right, those moments that make up the not-so-fun, not-so-shareable parts of running a company. Joining Greenwald was Saxbys CEO Nick Bayer, Lula cofounders Adit Gupta and Tom Falzani, and Kaela Blanks, a DEI culture strategist at Wawa.

“When I’m having a positive leadership experience, I’m probably celebrating that by doing pilates,” Bayer told the crowd at the Nov. 17 event. “If it’s a tough day? Probably with a martini.”

The rest of the panel shared their own not-great-day reactions. For Gupta, it looks like locking himself in a room and making a lot of to-do-lists. For Blanks, who’s a foodie, it’s shaking off the day with a new restaurant experience. Falzani said he probably “just looks like a maniac pulling out my hair.”

All founders have been there, Greenwald said. But those moments can also be learning experiences.

“What moment, do you realize now, was a mistake?” she asked the panelists. “And how would you handle it now?

Can folks I’m leading give me constructive criticism? How am I prepared to hear that and respond?

Earlier in their career, Blanks said, they were a “serial volunteer” — someone who took on more and more responsibilities, saying yes to advisory boards or leading different teams or volunteer efforts.

“I’ve since learned how to motivate people in interesting ways, and the intrinsic value of motivating them,” Blanks said. “But I had to learn to step back and hold folks accountable, when the work is not just for money.”

For Bayer, some mistakes came when the company was growing and he went from running every department in the business to managing and leading others to do those things.

“You wear every single hat, then you start to hire people to do things better for you,” he said. “It’s changed and evolved. Now I spend a lot of time with investors, stakeholders, people creating the learning platforms. I used to be connected to the most important part of the business, and now I am less connected to it and that was a big, at times clumsy, change.”

Looking back at past missteps in leadership moments, Blanks said they’re now cognizant of having an accountability partner who allows for truthful, respectful feedback.

“I think I’m a good person and good leader, and you can have the best intentions, but how are you hearing a different point of view?” they said. “Can folks I’m leading give me constructive criticism? How am I prepared to hear that and respond?”

For the cofounders of Lula, one of their biggest “leadershit” moments have also lead to their biggest lessons. Gupta said a year and a half ago, their first investor pulled out at a critical time. The pair learned to stay in contact with investors, not just when they’re actively looking to fundraise, but even to call for advice. It also lead to the way they shape their environment with their team.

“Adit and I have gone through a lot, [but] we make sure to have a fun, safe environment,” Falzani said. “It’s tough to own a mistake. But we want to make sure to create an environment where everyone can own up to it — where everyone feels comfortable talking about something that went wrong and how we can ultimately learn from it.”

And the perspective that can only come from getting back up after a leadership flub, per Gupta: You will have these days, but don’t beat yourself up about it.

A tidbit from @startupleaders’s Founder Factory earlier this month from @lula_delivery’s Adit Gupta pic.twitter.com/mNW47A3DlA

— Paige Gross ✨ (@By_paigegross) November 29, 2021