Reboot Podcast Episode #44 – We Are Designed to Fail – with Nicholas Russell

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 44 // July 8, 2016

Our capacity to fail is essential to what we are. The gap between what we are and what we can be is also the space in which utopias [or our entrepreneurial endeavors] are conceived. Ultimately, our capacity to fail makes us what we are; our being as essentially failing creatures lies at the root of any aspiration. For, in a sense, the capacity to fail is much more important than any individual human achievements: It is that which makes them possible. We are designed to fail.”


Nicholas Russell

Nicholas Russell

Entrepreneur. Previously Co-Founder and CEO of We are Pop Up

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Episode Description

Startups fail. We hear it all the time.  Failure is good. We hear that all the time too.  But we rarely hear about the pain, the shame, and second-guessing.  And even worse, we rarely hear about what opportunities may lie for our own growth in something ending beyond the pivot and lessons learned….A startup failing is not proof that something is broken within you.  In fact, it’s an opening and opportunity to find something new within you and for you.

Nicholas Russell was co-founder and CEO of UK based We are Pop-up. yes, I said was. Nick joined Jerry on the very day he handed over the keys and closed up shop on his startup of 3+ years.  In this discussion, Jerry and Nick talk about what he’s experiencing now, what he learned and wishes he had done differently, and a surprising path forward for that supported me through my own painful ending, and one that could be helpful for you in your own transitions.

As Nick said on the episode, he welcomes anyone who would like to chat with him to email him at Nick AT

Nicholas Russel on Twitter


Show Highlights

Top Quotes:

“As of today, we have sold [the business] and handed over the keys.” – Nick Russell

“I have thought about the [Reboot] Bootcamp every day since going on it.” – Nick Russell

“A lot of times we are afraid of failure, but we are afraid of a kind of conceptual failure.” – Nick Russell

“I thought we were quite advanced after having spent 3-4 years on this thing and pushing it forward.” – Nick Russell

“I let go of the team, cleared the bank accounts, let go of the company, and tried to sell to some competitors.” – Nick Russell

“Looking back, I see that we had just scratched the surface of the journey.” – Nick Russell

“I go back to the original genesis, and I would have said that we accomplished about 70% of what we wanted to do, but now I look back and I think we accomplished about 2%.” – Nick Russell

“You love the founder title and the energy around having a tech company, being a tech person, and that whole kind of halo.” – Nick Russell

“It is like you trying to get to the moon, you launch enough test rockets to know you can get there, but then your funding is cut.” – Nick Russell

“The hardest part is letting go, and what to let go of.” – Nick Russell

“Do you want to continue the journey if it is somebody else’s journey?” – Nick Russell

“We sent out an email to 50,000 people announcing that the site was closing, and it was for sale.” – Nick Russell

“We made a decision as a founding team that we didn’t understand the consequences of.” – Nick Russell

“The business needed more, but it was going the right direction.” – Nick Russell

“If it had been a hard failure, it would have been easier.” – Nick Russell

“The hardest point was the decision to pull the plug.” – Nick Russell

“There came the moment where I said I can’t take any more money on this cap table.” – Nick Russell

“Living with it is the difficult thing because it’s so easy to imagine the other outcomes.” – Nick Russell

“If I keep going in any fashion, would that be just another compromise?” – Nick Russell

“I’m very proud of myself for seeing it through to the end. We tried so hard, and we never gave up.” – Nick Russell

“It feels like we got robbed.” – Nick Russell

“We did some due diligence, but they liked the guys, it was a good working relationship, and felt like we were aligned.” – Nick Russell

“I remember the meeting when we said the terms were a bit rough. There was another discussion to be had there.” – Nick Russell

“Shit inevitably hits the fan.” – Jerry Colonna

“A lot of times, people will take bad terms in order to get a good valuation.” – Jerry Colonna

“Take your time and really understand what you are signing up for.” – Jerry Colonna

“Raising capital is a consuming process. Even in the best markets and times, it is always a consuming process.” – Nick Russell

“I needed a better picture of the investment scene and that investor.” – Nick Russell

“It sucks because I don’t want to be the martyr start-up.” – Nick Russell

“You can get hamstrung by bullshit.” – Nick Russell

“Everything you worked for can fall over because you didn’t prioritize everything.” – Nick Russell

“The way we deal with the pain of our own lives is to use it as a means to reach out to someone else.” – Jerry Colonna

“Maybe we were never going to be the Airbnb or the Uber.” – Nick Russell

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