Discovering Self Inside a Super Maximum Security Prison

Pelican Bay Supermax Prison. I’m locking eyes with Gary, separated by a perforated metal screen as zero physical contact is permitted with residents of the Secure Housing Unit (SHU), the prison’s solitary confinement facility.

While I’m aware Gary has been “inside” for more than 15 years, I’ve no inclination to ask about his reasons for being here.

Instead, we’re focused on an exchange guided by Defy Ventures CEO Catherine Hoke as I’m part of a team of 20 volunteers who are all facing individual SHU residents and now engaged in a series of interactions advancing each resident’s ambition to change their life by taking advantage of Defy’s highly refined program featuring guided personal development with many check points for accountability along the way.

The warden tells us it is the first time a group exercise has ever been done at Pelican Bay SHU, as no organization has ever ventured in with a track record to suggest having an impact on this segment of residents who are as isolated from society as you could possibly find.

Defy Ventures is a seven year old non-profit committed to reducing America’s recidivism rate. More than two-thirds of those released from prison, returned to incarceration within 5 years.

This mind blowing rate of returning people to prison is just one of the forces propelling the U.S. to hold 25% of the total prison population of the planet, even though we have less than 5% of the global population.

While other forces like lack of opportunity in disadvantaged areas, broken families, substance abuse, underperforming public education, electoral politics and inherent bias in the criminal justice system all have layers of contributing factors that go beyond the scope of this post, no one would disagree that a primary goal of our prison system should be to rehabilitate the incarcerated so those released can be productive in society and break the cycle of criminal behavior that too often continues into succeeding generations.

Not surprisingly, as employers are reticent to hire released felons, a parolees’ lack of opportunity to progress in society erodes hope and triggers gravitational pull back to the relationships and environment, which too often leads to a subsequent criminal act.

Defy’s approach to addressing this seemingly unsolvable problem is to help both prison inmates and recently paroled join on a committed path as Entrepreneurs-In-Training (EITs) – enabled by a combination of tightly structured self development and hands on help from a cast of highly accomplished volunteers.

The results of this program are nothing short of astounding. Of the 2,000 Defy graduates, 166 businesses have been created, spawning 350 new jobs for people with criminal histories.

Defy has had only 3.2% of their graduates return to prison. When you consider the cost of incarceration in California is $70,202 per year per inmate and an investment in an in-prison Defy EIT is $500, that results in a 294x SROI for California’s taxpayers.

But the win is far more than dollars saved as the real victory is putting individual lives on a productive path, breaking a cycle of returning to criminal behavior and bringing positive effect on lives surrounding the EIT like their family, friends and others seeking to break away from criminal behavior.

Everyone Invited, Only the Committed Advance

Being an entrepreneur is an alluring path for many, especially people with a limited range of options available to them. But only the committed will thrive as the failure rate for small business is often cited at 80% within the first five years.

Defy has evolved their entrepreneur development program so that it combines online and in-person exercises requiring an EIT’s sustained commitment to advance towards graduation.

Parolees access Defy’s online learning modules over the web and because, inside prison this is typically not an option, Defy’s video based learning can be accessed on the prison’s TV network.

At each phase of development, EITs are given assessment exercises that are tracked for completion through Defy’s Learning Management System.

In both “inside” programs and those on parole, EITs form support groups where they are helping each other stay on track, forming relationships with those who share a common ambition of finding success through entrepreneurship and strengthening commitment to avoid returning to a criminal life.

Mutual Respect Begins With Shared Understanding

As EITs progress in their development, they are offered opportunities to participate in high impact personal interactions with a very impressive group of experienced entrepreneurs, executives and investor volunteers.

Through a series of interactive exercises, volunteers and EITs come to know each other and learn about each other’s lives in ways that highlight their differences and similarities. In one exercise, separate lines of volunteers and EITs face each other, then step to a center line acknowledging how environment, family and impact of selected circumstances played out with either fortuitous or unfortunate outcomes now determining their status as an EIT or professional volunteer.

It is the similarities more so than the differences that are striking for me.

Like most volunteers, it is a huge “aha” moment to wrap my head around the realization that, with just a minor twist in my own life circumstances, it could easily have been me standing in the EIT line or see EITs with the clear potential to have ended up on the volunteer line as successful professionals.

That shared understanding of each other’s position begins the process of building mutual respect that in turn powers advancement of both EITs and volunteers in our respective journeys.

For in-prison events, volunteers provide coaching to EITs on topics that include articulating their personal elevator pitch, resume feedback, mentoring on the business idea the EIT is developing and participating in pitch competitions.

Volunteer support for those who are released include those activities as well as supporting and tracking an EIT’s progress and linking EITs to resources that can help their business succeed.

In all situations, EIT contact with volunteers follows a strict protocol managed by Defy in a way that preserves privacy and security considerations.

A Different Kind of Volunteer Impact

Since I was already deeply engaged in helping lots of first time entrepreneurs, the fit for me to check out Defy was pretty easy. While the audience was different than the startup world I am typically engaged in, the activities seemed right within my wheelhouse.

My expectation before volunteering was that my ability to have impact would be based on my knowledge, entrepreneurial experience and relationships I could bring to the program.

But beginning with my first event, the nature of my interactions with EITs were in such sharp contrast with the traditional world of helping startups I began to understand this was less about my professional qualifications than it was an opportunity to grow by being vulnerable and giving without expectation of return.

You see in the traditional startup-coaching scenario we don’t spend much time showing personal vulnerability. We go right to diving in with the help and expertise we think we’re there to give.

And even if we tell ourselves we have a “pay it forward” mindset, we know the startup world has so many interconnected relationships there are paths where our volunteer contributions may come back in some form of unexpected reciprocity – be it new deal flow, a helpful entrepreneur or investor contact, or referral to a highly valued source that can help us.

Defy Interactions Can Be Transformational

The Defy personal interactions are humbling in their effect of acknowledging vulnerability and rethinking about forces that led to how I arrived at the stage of my life where I can qualify as a Defy volunteer.

And when there is zero expectation of reciprocity, it forces the commitment choice on what my real reason for volunteering is – am I sincere enough in my values to walk the talk of pay it forward, or not?

Locking eyes with Gary and continuing our discussion through the perforated metal screen brought home that realization on how any impact I was having wasn’t about my professional experience, but instead my ability to show understanding, compassion and commitment to someone otherwise cut off from society.

I’m thinking that after our exercise concluded, Gary replayed the interaction in his mind as many times as I have. For different reasons, perhaps we both came away feeling we grew as a result.

So my own success measure for Defy volunteer participation is now flipped from where I was at the outset.

These powerful in-person interactions have done much to alter my personal outlook in a transformational way – something that I simply don’t get in the traditional role of mentoring startups headed by people that have already been dealt a pretty good hand.

But that benefit of a transformational outlook comes only as a result of participating with Defy in person.

It’s alluring enough to keep me coming back for more, and is probably the underlying force behind Defy’s high rate of returning volunteers – which is the only kind recidivism you really want to see!

CatskillsConf: Fun mashup helps build startup community

Just came off a very fun and worthwhile weekend at the inaugural CatskillsConf – a three day affair that brought together an eclectic mix of creatives, tech people, foodies and startup community supporters.

Was cool not only because the organizers were able to successfully pull off marketing to assemble 120+ people that touched on all those themes, but the diversity included an audience nearly evenly split between Upstate and NY metro.

This was the first ever such gathering in the Hudson Valley/Catskills area. It came about after founders of the Hudson Valley Tech Meetup (Dan Stone, Daniel and Sabrina Shutzsmith and Kale Kaposhilin) met Aaron Quint, (web entrepreneur and former Paperless Post CTO/Chief Scientist) who recently transplanted from NYC to the Hudson Valley.

Pooling their combined organizational talents, passion for bringing people together and lists of contacts is what catalyzed CatskillsConf and their joint marketing outreach filled the room.

Leveraging Local Assets

Whether it was musical talent, farm to table culinary, wood crafts and natural settings of the Ashokan Center, this was a thoughtful mashup that brought diverse elements together with common themes that spoke to the millennial target.

On the learning side, my personal favorites were Dennis Crowley’s “put it all out there” story reflecting struggles at different stages in the startup journey, and also an amazing education segment featuring live birds of prey doing their thing.

birds of prey

When you’ve got a group together for more than a day, it gives opportunity to go beyond a large group learning setting to do some things that can be hands on, fun and social – all adding to the potential of building on strong relationships among participants.

The Catskills flavor for small group activities included options like foraging, blacksmithing, cider making, bookbinding, and drone piloting to name just a few.

Institutional ownership not a requirement for success

More than just a well run event, what’s unusual here is that the outcome wasn’t oriented towards benefiting a particular organization – but rather to just grow the relationship networks for participants, while having a fun time and creating many memories.

My boomer generation just isn’t used to seeing grass roots organizing like this without institutional ownership and resources.

New relationships will yield downstream benefit

As I browsed around, a frequent comment from local tech people sounded like “I used to think I was the only person around here like me. As a result of the groups forming and events bringing like minded people together, I’ve now got a growing network of supporters to help me.”

As I try to calculate the number of “creative collisions” that occurred and what happens when like minded people stumble into each other for the first time, there is little doubt that startup formation and growth will include some life changing outcomes sparked by what seemed like chance encounters.

Good things happen when a few people step up to lead

Kudos to the organizers as they took financial risk and put in a ton of hours along with a full supporting team of volunteers.

They set an inspiring standard for others to follow and their leadership adds further fuel to my optimism about why it is the millennials who are making the difference in powering Upstate towards a big jump in the number of new industry companies and jobs that will rise here from humble beginnings as people meeting at an event that then lead to collaborating on a startup.

We pledge our resources at Upstate Venture Connect to support their efforts and look forward to doing the same for all others ready to lead the charge in their own local market.

Confidence and humility are not mutually exclusive

As I meet entrepreneurs seeking to launch their first startup, I’ve begun noticing behavioral traits I wasn’t paying much attention to before.

Signals I’m picking up more frequently are from entrepreneurs coming across as super confident (even aggressive), perhaps in an effort to show they are hard driving and ambitious.

While confidence in one’s beliefs is indeed a critical asset for a startup entrepreneur, my BS detector begins kicking in when I see a total absence of humility. The tells are things like:

– working their accomplishments into the conversation
– no hint of what they don’t yet know or are seeking to learn
– expressing no curiosity about whom they’re interacting with
– interactions appear motivated only by potential self interest – no evidence of “pay it forward”
– how they interact with others who serve or bump into them seems different than their style of interacting with those in a professional context

Because I’m an investor who looks hard at leadership qualities of the CEOs I want to work with, my mind gravitates towards thinking: “If this is what I’m noticing now, I wonder how it translates to future interactions this entrepreneur has with others they seek to recruit and lead?”

Humility as a leadership trait

If you’re looking for thoughtful insights backing up the quality of humility in leaders, check out Jim Collins’ Good To Great and his work profiling Level V leaders. His research supports the thesis that CEOs embodying the unusual combination of fierce resolve and personal humility ended up being a critical leadership trait for top performing companies in the study.

My own view was shaped most by my Dad and my wife Krista, but also the good fortune of having close contact with a bunch of exceptionally strong leaders who personify humility in how they lead and interact with whomever they meet.

Jack Stack, Founder/CEO of SRC and visionary behind the Great Game of Business would certainly top my list in exemplifying resolute commitment and personal humility. SRC is not only a phenomenally successful company that has transformed thousands of lives, but beyond Jack’s Southern gentleman’s humble style, his open sourcing of the GGOB and open book management practices empower a generation of entrepreneurs like me to embrace principles around getting everyone in a company to think and act like owners – the ultimate management humility as it means running an organization with the power bubbling from the bottom up.

Back in 1995, Anthony Martin, now retired Chairman/CEO of global staffing giant Select (and subsequently Vedior) picked TriNet to invest as one of the 40+ companies in his portfolio. Much to my benefit, he traveled “across the pond” for 10+ years to sit on TriNet’s Board of Directors. Soft spoken with never a wasted word, his gracious, gentle, almost patrician manner helped set the tone for our board meetings with wisdom that came through penetrating observations and questions that were so much more effective than the contrasting style of boards featuring competition to demonstrate who is the smartest guy in the room.

In the emerging tech world, anyone that knows or interacts with uber VC Brad Feld (@bfeld) will attest he gives so much of himself to so many causes (building entrepreneurial ecosystems, women in tech, computer science education and entrepreneurship globally to name just a few) and notwithstanding an incredibly packed and productive schedule and contact list, still shows an uncommon curiosity and willingness to pay it forward with each new person he bumps into.

Humble, super successful people stand out

So I take notice when I encounter a super successful person who isn’t showing the expected trait of being the center of attention in a dialogue among a small group.

My respect grows as they instead show curiosity in others and demonstrate care and concern for people they don’t know, as well as how they contribute talent towards things not driven by self interest.

Encounters like these also reinforce my not losing sight of humility in what I say and do.

Paying it forward is going to be a theme I hope to keep shining more light on. Not only to help keep me centered, but also my belief that raising awareness of success beyond financial measures is the real story behind entrepreneurs with the most impact.