Reboot Podcast

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.

#53 – Transform Your Hustle – with Catherine Hoke and Brad Feld

Episode 53 // January 19, 2017

“I’m running from nothing, no thoughts in my mind
Oh my heart was all black
But I saw something shine
Thought that part was yours, but it might just be mine
I could share it with you, if you gave me the time
I’m all bloody knuckles, longing for home
If it weren’t for second chances, we’d all be alone”

Guests

Catherine Hoke

Catherine Hoke

Founder & CEO of Defy Ventures

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Brad Feld

Brad Feld

Investor

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Episode Description

Almost all successful entrepreneurs will fail – if not fail, fail, fail, and fail again – on their path to success. Every human being made choices in their lives which they regret, are embarrassed of and have caused them deep shame. What would your life be like if you were known only by the worst thing you had ever done?

Catherine Hoke is the founder of Defy Ventures, a program that helps incarcerated individuals transform their hustle to entrepreneurial ventures. Following a chance visit (as a guest) to a prison at the age of 26, Catherine left behind a successful investment career to launch a program to build on what she recognized were valuable entrepreneurial skills – simply applied to illegal businesses. Through the journey of building two wildly successful organizations, Cat had her own personal experience of failure, great shame and having to grant herself grace, and a second chance.

Nestled in this conversation about failure, mercy and second chances, is an important second discussion. Joined by investor Brad Feld, this episode also includes a heartfelt reflection on the lottery of birth, acknowledging our own privilege, and what we can do when confronted with these realizations.

Show Highlights

Top Quotes

We use entrepreneurship as a tool that brings people together to celebrate success. – @catherine_hoke

The more important work of @DefyVentures is holistic life transformation and making people feel human. – @catherine_hoke

So many [people] want nothing more than a second chance. Today I’ve learned to see that it’s really about a legitimate first chance. – @catherine_hoke

I asked myself the question, “If I had been raised in these circumstances, how would I not end up on this path too?” – @catherine_hoke

What would happen if they transformed their hustle? – @catherine_hoke

I used to always preach grace but I didn’t apply it to myself. I didn’t understand it. – @catherine_hoke

My own failure is my own superpower. – @catherine_hoke

What would it be like if you were only known for the worst thing you’ve done? – @catherine_hoke

Better humans make better entrepreneurs. Being more human is the path. Being more real. – @jerrycolona

One of my favorite reasons for working with our men and women is they’re so hungry and coachable and partly because of their shame. That leads to real humility. – @catherine_hoke

[Attending a Defy EIR graduation] was a top 10 peak life experience. – @bfeld

[The Defy EIR graduation] forced me to really confront the notion of privilege and the idea that it’s very easy as a successful white male who grew up in a middle class family with loving parents and went to a great college. – @bfeld

I don’t even have a beginning of an understanding of this. It’s fucked up and it’s not right. – @bfeld

[The Defy experience] changed my view on what is actually meaningful in that and how I relate to it. – @bfeld

A lot of what makes me good at my work is my rage. I stay really close to the rage. I intentionally engage in things that make me mad. – @catherine_hoke

Thank the fucking Lord that Martin Luther King got angry. – @jerrycolona

Change happens when we find the jet fuel of passion. – @jerrycolona

Part of my learning to be an adult is learning how to be in touch with my own feelings. – @jerrycolona

No one is irredeemable. No one is garbage. – @jerrycolona

Key Takeaways

Catherine Hoke is the founder and CEO of Defy Ventures, a program that helps incarcerated individuals transform their hustle to entrepreneurial ventures.

Brad Feld is an investor, partner in Foundry Group and has recently joined the board of Defy.

Catherine Hoke was working in investments when at the age of 26 she was invited on a prison visit. At that time, she recalls having a hardened perspective of people in prisons- viewing them with little mercy or grace and not believing in second chances.

During that visit and her interaction with one inmate in particular, she experienced a complete transformation of her perspective. She saw that most inmates had grown up in challenging circumstances and she began to wonder how that experience would have affected her. She believed these people were worthy of mercy and grace- while also recognizing that many of them possessed valuable entrepreneurial experience and skills which could be applied to legal businesses.

Shortly after that visit Cat left her job and founded a program in Texas that taught entrepreneurial skills to inmates. The program was a huge success. Five years after its launch, Cat made what she calls regrettable decisions- engaging in personal relationships with some inmates. She was forced to resign from the organization and publicly shamed.

As painful as that experience was, Cat believes it has made her more determined and better suited to do this work. She experienced first hand what it is like to be known by the worst thing she had ever done, just like Defy program participants. Until that experience she would preach grace but did not apply it to herself.

Jerry recalls the Buddhist tale of Milarepa, a quite unsavory character who underwent a transformation when he met Marpa. Milarepa is the featured character in many Buddhist stories. He recalls in particular one in which Milarepa faces his deepest fears, by putting his head into the demon’s mouth.

Cat mentions that one of her favorite reasons for working with our men and women is they’re so hungry and coachable and partly because of their shame. That leads to real humility.

Jerry mentions that entrepreneurs and people who are in the prison system share a particular common trait, which we at Reboot refer to as premature promotion. They are thrust into being an adult long before they are prepared to be that. Oftentimes they’re thrust into positions of having to take care of. That can be a power that does destructive things, but it can also be a power that creates powerful constructive things in people’s lives. It turns them into early leaders.

Brad connected with Defy Ventures through their application, and being a recipient of, a grant from the Techstars Foundation. Shortly after being awarded the grant, Cat came to Boulder, met with Brad, and Brad recalls feeling immediately invested in what she was doing, wanting to be more involved. She invited him to be involved in an upcoming program at a prison.

Of the experience Brad recalls, “characterize as a top 10 peak life experience. It wasn’t best life experience but peak in the context of the emotional intensity, what I learned from it, what it caused me to reflect on at many different levels versus just you have this amazing experience but it’s one-dimensional amazing experience. This was a multi-dimensional amazing experience and it was in a context that was in some ways completely foreign because it was in the gymnasium at a maximum security prison.”

Attending the Defy EIR graduation was deeply affecting for Brad. Through meeting and getting to know some of the program participants Brad recalls that it forced him to “confront the notion of privilege and the idea that it’s very easy as a successful white male who grew up in a middle class family with loving parents and went to a great college.”

Brad recalls watching at the end of the day as program participants took part in the graduation ceremony. The pride and excitement of people as many of them received a diploma for the first time, wore a cap and gown and were applauded.

Catherine mentions that a lot of what makes her good at her work is her rage. She intentionally engages in things that make her mad to fuel her drive and determination.

Jerry mentions that there is a place for rage. There is a place for anger. Change happens when we find the jet fuel of passion. Rage can express itself in inappropriate ways and it can express itself in appropriate ways. Part of learning to be an adult is learning how to be in touch with my own feelings.

Once someone goes to jail there is a 76.6% chance of being rearrested within five years. 70% of the children of people in prison follow in their parents’ footsteps to prison.

All people have universal desires for love, safety and belonging. One of the many, many expressions of the complications of being human is that we can pervert the wishes for love, safety and belonging into replication of that, which we see.

Punishment alone doesn’t work. We need rehabilitation.

95% of the people Defy serves have been convicted of violent crime. Once released, Defy participants recidivism rate is less than five percent. Graduates of the program who have been released are now creating jobs for other people on their release.