Reboot Podcast Episode #68 – Your Second Act – with Jason Jacobs

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.

Episode 68 // September 21, 2017


Jason Jacobs

Jason Jacobs

Entrepreneur, founder of Runkeeper

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Episode Description

Jason Jacobs, founder of Runkeeper, pursued being an entrepreneur with passion and maniacal focus. After starting Runkeeper at age 30, he now finds himself on the other side at 41 post-acquisition, finally reflecting back on the last decade of work. Knowing that he wants to experience building the next company differently, in a more healthy way and with more joy, Jason talks with Jerry about the conundrum of getting lost and consumed in the fire of work. And, how to dive into his work without being so unhappy. At this mid-life juncture of Jason’s time before his “Second Act,” they take the opportunity to pause and unpack deeply held notions about how work must be, what success is, and what it means to lead a fulfilling life.

Jason Jacobs on Twitter  | Jerry’s blog post on the Problem of the Potter | Man’s Search for Meaning

Show Highlights

Top Quotes:

“My bias was always: company, company, company.  I thought: someone can look inside my head some other time.’” – Jason Jacobs

“I love entrepreneurship. But I didn’t necessarily do it in a sustainable way during my nine-year journey.” – Jason Jacobs

“The journey of creation is quite grueling, and doesn’t necessarily bring happiness along the way.” – Jason Jacobs

“It was the company at all costs over the last nine years, which is not healthy.” – Jason Jacobs

“Buried within the pursuit of happiness, is our own undoing, because the pursuit of happiness, leads us to create a sense of attachment.” – Jerry Colonna

“I almost actively stamped out joy during points of time building the company because I viewed joy as a distraction. I was maniacal about focus.” – Jason Jacobs

“I didn’t view joy as productivity-inducing.” – Jason Jacobs

“Some of our first models of “what does it mean to work” get formed in childhood as we’re watching Mom and Dad go off.” – Jerry Colonna

“The opportunity at midlife – in this second act – is to pull up the parts of you that are defining you and examine them.” – Jerry Colonna

“If you really want to be effective in inspiring that joy around other people, you have to allow yourself to inspire the joy within yourself” – Jerry Colonna

“My nightmare is having great professional success and looking in the mirror not being proud of who I see.” – Jason Jacobs

“The answer to the conundrum of fulfillment or happiness is actually integration.” – Jerry Colonna

“The people who are most trapped … are using external yardsticks to judge their self-worth.” – Jerry Colonna