Reboot Podcast Episode #166 – We Can Choose to Ride the Roller Coaster of Entrepreneurship – with Jean Smart

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.


Jean Smart

Jean Smart

Founder and CEO of Penelope

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Episode Description

For leaders, navigating the roller coaster experience of entrepreneurship can be flat-out exhausting. The constant fluctuation of riding highs and surviving lows often leaves little time for reflection, much less appreciation for how far you’ve come. But what if there was a different way? What if you didn’t have to ride the rollercoaster at all?

In this episode, Jerry sits down with Jean Smart, founder and CEO of Penelope, a retirement savings platform exclusively for small business owners and their employees. Jean describes how growing up as a child of Korean immigrants and watching her parents struggle to save for retirement served as the impetus for creating Penelope. She reflects on the responsibility she carries to be a good steward of her business and the new weight she feels to represent Asian women in the fintech space. Jerry urges Jean to return to the question, “Why do I do what I do?” when things get overwhelming, and provides guidance for how to view the rollercoaster from the ground versus strapping in for the ride.

Show Highlights

Top Quotes:

“You’re a daughter of immigrants, you’re an immigrant, you’re the oldest, you’re a mom, you’ve got a bunch of people who’ve taken big salary cuts, you’ve taken venture money, and you’re trying to be the best steward of it. You can’t mess up.” – Jean Smart

“I didn’t fully understand the stats around women founders, funding minority founders. I knew high-level, but I didn’t know how minuscule. I don’t think I understood the full weight of what that meant.” – Jean Smart

“I’m a coach. And part of my job is to help people be able to withstand the vicissitudes of what they’ve stepped into. And part of the tool set that I would give you, is the ability to pause and recognize what you’ve accomplished, the extraordinary experiences in which you find yourself operating. Not to hold yourself back and stay stuck in that space, but to just take a breath and realize, this shit is hard.” – Jerry Colonna

“When we endeavor to launch something brand new, and we convince people to take a pay cut to come join us on this crazy journey, we implicitly sign up for a certain kind of responsibility for their well-being.” – Jerry Colonna

“So you have this parallel process of structural racism, institutionalized racism, basically identifying who got the American dream and who didn’t get the American dream.” – Jerry Colonna

“I often encourage folks to hold an awareness of what their ancestors went through. Because they teach us in subtle ways.” – Jerry Colonna