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!

Road Trip: Spending time with those we love


I just completed a drive home to Little Falls, New York originating from the San Francisco Bay Area.

With a few zigs and zags, it was about 3300 miles over 8 days.

This was my 9th cross country road trip, but the first with my son Jared since 1999 when our entire family relocated from Silicon Valley to my Upstate hometown by way of a 2 week cruise in an RV. He was then 6 years old so memories were a bit sketchy for him about that experience.

Now as a young man with an experienced traveler’s curious eye, Jared’s interest in a road trip evoked a positive reaction as soon as I brought up the idea.

While the ostensible reason was to transport a car we had in California to our home in Little Falls, I didn’t hide my interest in both the road trip experience and our spending some quality time together.

Because of winter weather risk traversing the Rockies this time of year, we took a southern route heading east along Interstate 40 and the old U.S. Route 66.

Desert and high plains from Las Vegas to Santa Fe were particularly scenic, and we veered off for side stops sometimes on a whim – like after seeing roadside billboards for the Billy the Kid Museum in Fort Sumner, New Mexico.

In comparison with cross country trips I did a decade or longer ago, I was struck this time by how much easier it is now with so many enhancements in the richness and ease of accessing information while on the fly.

We began the drive with no more planning than a general idea of the route and then made it up as we went along each day.

Google map features making it easy to pick up interesting attractions and stops along the route added to the process of discovery – so there was no difficulty in figuring out options we wouldn’t be experiencing back home, including dining in memorable settings like The Big Texan in Amarillo.

In picking the route we also stopped by to see a few friends, each of who had something to add to Jared’s experience. Our most memorable being time with my personal hero and mentor Jack Stack as we re-connected with him for the first time in about a decade.

The highlight for me though was the time Jared and I spent being together without distraction of outside influences. Sharing our observations, perspectives and thoughts in a relaxed way without the pressure of the next deadline or meeting.

We know that the convenience and relatively low cost of commercial air travel combine to put a big dent in long distance family road trips.

The wider range of leisure options we can easily find also builds a subtle time pressure to pack as much as we can into any time off period, perhaps sometimes with a feeling of being ready to tell others about where we’ve been over vacation.

Call me old fashioned, but I still like the road trip as a choice on the week or longer vacation menu. There is so much diversity in scenic beauty, attractions and culture right here in the U.S. Sharing with those we love is an experience best savored without tight timelines driven by flight schedule and limited time in a single location.

I’m a lucky guy to have a 23 year old son that shares that interest and still travels with his Dad. We made some memories together that will be with us always – and that’s what leisure time in our family is all about.

Embracing Public Company Readiness in Scaling a Private Company

TriNet’s IPO was the culmination of contributions from a ton of people over a very long time period.

Few outsiders were aware that our management team adopted a philosophy of being “public company ready” way back in 1994.

Over the two decades from then till going public last March, our leadership team had several themes related to readiness that served as key filters for decision making in both setting expectations and allocating resources.

Being accountable to a budget

Paramount on the list of readiness factors is defining a realistic growth budget and then delivering on the results.

While all CEOs espouse the importance of this basic principle, now that I’m an active early stage investor with an inside look into a large number of fast growth private companies, it seems only a small minority of those I see come even close to that deep commitment of learning how to deliver on budget expectations as they are scaling up revenue.

All companies going through a rapid growth phase encounter uncertainty around market adoption as well as unexpected bumps from the external environment – be it competition, market forces, technology changes and government regulation to name just a few.

And the faster the growth, the harder it is for the team to adapt as they have to evolve internal processes that affect consistency in how the company attracts, prices and services customers at higher volume – all of which ultimately drives the forecasted results.

But the public company principle is that as leader, I was never in doubt that my tenure as CEO was directly related to my ability to accurately predict the future in terms of where our revenues and profitability would be up to a year or further out from where we were at any point in time.

So developing competency in how to do that wasn’t something that I could learn in a single year or delegate to someone else, but instead had to work towards instilling commitment to setting and delivering forecasted results throughout the entire company every single quarter.

Institutionalizing Accountability Begins With CEO Direct Reports

Even if the CEO is “all in” on the importance of setting realistic targets and delivering on that, no single person can make that happen on his or her own.

If I was being measured by how accurately I could predict future quarters, it wasn’t a big stretch to say that should be the same approach in how I looked at my direct reports.

That put my focus on making sure I was getting that intense commitment from my direct reports to both setting expectations within their respective department, and that those commitments were direct linkages to support achievement of the overall budget – especially on how everyone in each department was contributing to growing revenue.

It was up to me to define the process by which we would define and track progress of goal achievement and set the example of holding my direct reports accountable by showing consequences to the reporting executive if goals were not achieved.

Consistency in doing so, as well as supporting systems to report and track goal progress both helped push this approach company wide.

Transparency with Investors and Team Members

Predictability in delivering forecasted results is closely linked to having enough detail in the assumptions driving the budget to be understood by key stakeholders.

Initially, this is the Board and management team, but we found it very high impact to expand the knowledge and transparency through the entire company.

We boiled down a set of business drivers appropriate for full team consumption internally and then constantly reported on our progress so everyone knew where we stood against a full range of operating metrics and budget assumptions.

Another aspect of transparency was our internal mantra of “no related party transactions” as we knew any hint of executives or shareholders having anything less than an arms length arrangement would be a red flag that blows management credibility with sophisticated investors.

Having a “Big 4” audit firm is a huge boost for transparency. We took that on 20 years before going public and never looked back, notwithstanding the extra layer of fees we paid even through the lean years just we could hold to that standard.

Earlier start builds competency

In TriNet’s case, our public company readiness philosophy got a big boost after taking on a large public company as our controlling shareholder in 1995.

Even though we were a small entity rolling up into a big corporation, the public company principles were very top of mind to us as we planned and executed corporate governance over the next 10 years.

Our public company readiness ended up being a significant factor in TriNet’s successful transition from the corporate controlling shareholder to General Atlantic, our financial partner and controlling shareholder since 2005.

I can look back now and see how critical these steps were to laying the foundation for managing through challenges of an evolving institutional shareholder base – the most important undertaking any CEO who wants to be around for the long haul can take on.

And while few high growth companies will find their shareholder exit in the form of an IPO, those same public company principles will insure a stronger company on every dimension that is important to success for both internal and external stakeholders.

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.

Numbers not the only measure of entrepreneurial success

While most of my inbound startup inquiries come from first time entrepreneurs, this one was different. Even though he was still pre-launch, the aspiring entrepreneur is on the founding executive team of a company that went from startup to a successful IPO in six years.

Now with a year of public company executive team experience on top of managing through multi-year hyper growth, his view of the challenges and decision making to build a true enterprise were things I could relate to right away.

He was getting ready to leave the public company and venture off to start a venture where he would be a first time CEO. Plus he was in the enviable position of choosing to self fund or take his pick of investors at the door with Series A checks in hand before he even showed a pitch deck much less form a company.

What was surprisingly refreshing in our conversation were the entrepreneur’s thoughtful questions, and even a degree of humility that I almost never see from someone with that success pedigree.

After discussing the topic that prompted his call, he shifted into asking me about insights I might offer for the chapter 2 journey he was about to embark on. This was kind of fun for me, since sharing with someone who had been through what he had could be done with a lot of shared context so we breezed through some heavy topics quickly.

Imagining if I were in his shoes, three quick highlights came to mind:

1. Take some time off between gigs. Even though his vision for the new startup was a burning ambition, he is coming off six years of continuously running full tilt. Taking the helm to build a startup from scratch is an all consuming endeavor. The opportunity to recharge now, especially with family, might not be coming again for potentially several years or longer. No matter how quick the market might seem to be moving, there is no doubt that opportunity would still be there for him even if he took 6-12 months off now – time that could never be recaptured again.

2. Finish Big means a lot more than liquidity. When you’re in the trenches going through all that’s involved in building a high growth company, it is way too easy to fall into the trap of thinking how great life will be if you exit someday with a big payoff. However, in my own experience of speaking with quite a few other exited entrepreneurs, I’ve found many more of them unsettled with their lot than those who were leading fulfilling lives. Bo Burlingham’s recently published Finish Big – How great entrepreneurs exit their companies on top, covers this phenomenon with such great insight that I am now giving it to every startup I work with as they approach Series A financing. That’s right, putting the lens on what makes a successful exit (beyond financial measures) can guide decision making on influencing the kind of company culture to build and how to set expectations with those around you that you will want to deliver on.

3. The reward is the journey. In the 20 years of my serving as TriNet’s CEO, this became a mantra incorporated into my closing remarks at our quarterly all hands meetings. The thought is often attributed to Steve Jobs and to me embodies belief that reward isn’t measured so much by the imagined big exit, but instead by the little successes experienced by team members at every step we took along the way. No matter how hard we worked in constantly adapting to change, we sought out ways to reap reward from things like crazy ways to make meetings fun, hiring people we enjoyed spending our time with and friendly competitions to do things we could see made a difference for our customers and their employees. Memories of those shared interactions and successes will last a lifetime for me and many others who found intrinsic reward from being part the TriNet journey.

I’ll be watching with interest on how this new startup entrepreneur’s journey unfolds from here. He has the maturity that points to the right stuff. Those getting on his team are likely to benefit in ways they’ve not yet imagined.

Prior post with related themes – Startup to IPO: An Entrepreneur’s Reflections

Building Relationship Capital

With a big chunk of my time devoted to accelerating Upstate NY’s startup ecosystem, I think a lot about how starting new relationships is critical to making a successful startup community.

The ease in which strangers can drop into a place like Silicon Valley and meet the right people is a dynamic that outsiders aspire to, but don’t seem to put much energy towards figuring out in second and third tier markets like ours.

So among other initiatives, I’ve been playing up the importance of building relationship capital when I’m interacting with first time entrepreneurs who are usually pretty light when it comes to the relationship network they need to build a company.

Relationship impact may not be obvious at initial interaction

Any entrepreneur who has built a serious company will have their own stories about key people they met along the way who ended up having a significant impact on their success, yet their initial interaction seemed fortuitous.

In contrast, I’m seeing a lot of first time entrepreneurs focus maniacally on pursuing relationships they perceive will lead to capital, but with too narrow a focus that puts them at risk of overlooking others who might be possible mentors, advisors and referral sources. These are the relationships that eventually lead to capital providers, customers, channel partners or other highly prized relationships vital for a startup’s success.

A person I just met might open one door, many or none but I won’t know what will unfold until a relationship deepens over time. That means planting lots of seeds, nurturing the right first time interactions into relationships – especially with people having a mix of capability and interest in advancing a dialogue.

Relationship Capital Fueled By Being Proactive & Crossing Boundaries

Figuring out who to meet has never been easier. In this transparent world with such readily accessible information about people in business, how hard is it to come with a top 10 list of people that would be good to know, or the intel on who their friends are or where they hang out?

Supplementing a targeted list of people would be organizations/groups and events populated by people likely to include the profile of those having some things in common with your interests.

Again, a bit of research is needed – just don’t fall into the common trap of thinking that the only relevant groups are those somewhere within immediate view such as your university, local area or industry.

Developing high impact relationships are well worth the time to invest in targeting, crossing boundaries to new organizations and even traveling as needed to interact with a group of like minded others to tap into new networks and forge new relationships.

You give before you get

The principle of reciprocity captures the essence of what it takes to turn a chance encounter into the first stages of what could become a productive relationship.

Think about the casual interactions you might have at a reception event. In these settings, the most successful people I know are naturally curious and usually not the ones opening up unless questioned by others. Instead they query you about your interests, often times subtly honing in on the areas where they might possibly be able to help you.

Can you uncover something in your dialogue to offer up (even if at a later time) to that successful person asking you these questions?

Once you know more about the other person, your give might be a relevant article or post you came across, a recommended place or event or best of all – an introduction to someone else or a resource that you’ve figured out would be helpful to who you’re talking with.

Being Systematic

Planting lots of seeds and nurturing a whole bunch of recent contacts into productive relationships takes work that most people won’t do. Those who are truly connectors are organized with disciplined contact management and calendaring of follow ups.

In the TriNet world of referral generated sales, we learned to get highly systematic in building processes around keeping our reps constantly identifying and nurturing their top relationships – a foundational element of our building a referral based culture and company.

More recently, that systematic approach to relationship building is incorporated into IntroNet – an app which helps people connect others and track what happens with the introductions they make.

Any one of these relationship development tactics would produce some results in helping meet and come to know more people who could help you.

Put them together and you’ll be on your way towards achieving that next big thing, no matter what that might be.