Reboot Podcast Episode #72 – Heading Life’s Speed Bumps – with Matt Tara

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 72 // November 30, 2017


Matt Tara

Matt Tara

Founder of Tucker Blair

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Episode Description

Matt Tara is the CEO of an e-commerce fashion company that failed but is still very much alive in his head. As a former venture capitalist in private equity, Matt thought he’d be swift to success as an entrepreneur. When the road turned rocky, Matt was forced to put his company to rest, and he was left with many multifaceted feelings — among them: failure, grief, and the understanding of what it means when an entrepreneur says “this is hard.” Most of all, he felt abandoned and at a loss for peers who could really listen to him. In this conversation, Jerry helps Matt conceptualize the latest speed bump in his life. They begin to unpack all of the gifts and lessons he’s received from this experience and propose tactics for keeping Matt’s inner critic at bay as he considers what’s next.

Show Highlights

Top Quotes:

“You have two choices when you come up to the speed bump, you can speed up or you can slow down.” – Jerry Colonna

“I had that intervention and that countered my incessant need to not give up and be persistent.” – Matt Tara

“No one talks to me. It’s a pretty lonely life afterwards, you know?” – Matt Tara

“It’s a weird position when you always feel pretty financially secure and then you go through this experience that you give everything because you think that’s what you should do.” – Matt Tara

“Are you happy doing what you’re doing? And that’s different from, is this an idea that could work?” – Matt Tara

“One person’s success could be totally different than another person’s.” – Matt Tara

“Don’t let the business or your entrepreneurial adventures take over yourself.” – Matt Tara

“So you hear these voices. You have these internalized parents. You have the true existing parents. You have your inner critic. You have the words that people are saying all around you.” – Jerry Colonna

“Sometimes his persistence is healthy, sometimes his persistence is unhealthy.” – Jerry Colonna

“So this need to be the Leonardo da Vinci of life… That’s where I get in trouble because not only am I persistent, I have drive, and I’m doing things that I’m not innately good at.” – Matt Tara

“One of the biggest complaints that I hear from entrepreneurs is that investors just don’t understand how hard it is.” – Jerry Colonna

“It’s harder than that statement is. I mean I woke up and dry heaved one morning. because we owed money.” – Matt Tara

“You woke up with dry heaves and as an investor, you had no idea of what it meant to actually have those dry heaves.” – Jerry Colonna

“See the problem with ignoring the speed bumps is that you’re actually going so fast … that you’re not internalizing the lessons, painful and otherwise, that you just went through.” – Jerry Colonna

“You can be terrific with the best idea, with the best investors and still fail because your timing’s off or because two motherfuckers fly an airplane into the World Trade Center and destroy your business and that wasn’t their intent.” – Jerry Colonna

“There are so many factors that go into success and failure that to spend the time beating oneself up creates a narcissistic infinite loop.” – Jerry Colonna

“Spend more time with how painful it was so that you can extract the lessons so that you can then close the door.” – Jerry Colonna

“Do you think you can compress grief and lessons?” – Jerry Colonna

“I feel like I gotta put it in the closet like the winter coat. I don’t wanna keep thinking about it but then I have no choice.” – Matt Tara

“By staying with it, you’re not prolonging it. You’re actually speeding the point at which you will get past it.” – Jerry Colonna

“By staying with it, you allowed your inner being to catch up to what happened to be able to then not have to carry it forward.” – Jerry Colonna

“I just wanna talk about it. Right now, I just talk with myself.” – Matt Tara

“Peers means people who have gone through a similar experience. People who can relate empathetically.” – Jerry Colonna

“When you find yourself coming up to a speed bump and you have the impulse to go quickly, I want you to slow down.” – Jerry Colonna

“The biggest part is I feel like no one cares about this whole situation and that I’m making a big deal about nothing.” – Matt Tara

“Sometimes in the midst of our own pain, we fail to hear the crickets that are actually out there.” – Jerry Colonna

“No, you are not alone even though sometimes all you hear are crickets. Sometimes all you hear is the lack of response from the world.” – Jerry Colonna

“Never ever forget that there’s a value in listening. Not fixing, not solving, not changing, just truly staying present and listening.” – Jerry Colonna

“The word compassion means being with the other person’s feelings. Not fixing them, not changing them, bravely staying present.” – Jerry Colonna