Entrepreneurship Lessons From 40 Criminals

 At 6:40pm last night, I entered a room full of criminals. Ex-cons, to be exact. Needless to say, I couldn’t have been more conflicted about where to leave my laptop bag. I got over it by the time the hugging started. You might be wondering, how long after taking mushrooms is it safe to write LinkedIn articles? I assure you, last night was drug-free, purposeful, and life-altering.

The event was organized by Defy Ventures, a non-profit that trains ex-cons to be entrepreneurs and productive citizens. For me and about 35 other executive volunteers, the four hours flew by – as did the Domino’s slices. I’m not sure I can capture with words the intense, positive, and cathartic experience everyone in that room felt, so I’m not going to try. You can sign up and experience it yourself. Instead, I’d like to capture some powerful lessons from last night that might give you a new perspective on life, business, and purpose.

Elephant in the Room

Before diving in, let’s address the armed and dangerous elephant in the room. Why help ex-cons? Didn’t they hurt people? Yes. And they paid a debt to society. Now, we’re left with a choice: Do we create a population of outcasts who can never find work because of past mistakes? Or, do we suck it up like big boys and girls and admit everyone screws up and deserves another chance?

I can tell you what we’ve chosen. In many states, ex-cons can never vote and almost every single person I met last night told me they were either fired or rejected from jobs after their criminal record surfaced.

When ex-prisoners can’t find work, guess who pays the price? We do. Almost 80% of ex-cons are re-arrested within three years. That means they had to commit at least one more crime. It also means taxpayers pay between $29,000 and a ridiculous $168,000 per prisoner per year. For what? To be “tough on crime”? For moral bragging rights? Or, because we’ve got important Tweets to hashtag?


Even the staunchest law and order type can’t fight math. Wouldn’t it be better tocollect millions by creating thousands of new taxpayers (or employers of several taxpayers) than spend millions to imprison them?

9 Lessons

  1. Last night made it clear how rare soul is in businesses. Defy founder, Catherine Hoke, is an amazing leader who is driven in ways I might never be – or even understand. Her passion is contagious. That means it can scale and be taught to others, which I hope she does. In many ways it’s the exact opposite of the lifeless slugs that occupy desks at most government programs. Bureaucracy and passion don’t mix. Perhaps there are better uses for taxpayer money. Last night, I found at least one.
  2. Hustle beats books – For every three over-educated, over-thinking professional I’ve managed or advised, I would have preferred one hustler. As soon as ‘Mark’ sat down, he told me, “I can sell anything and I can find the best price on products people want.” Guess what, that’s exactly what he did. He finds deals on designer jeans, t-shirts, and anything else on sale. He marks it up and sells it through a network of connections. Why aren’t MetLife and New York Life recruiting ex-drug dealers and street hustlers to sell insurance? With some training and monitoring, they’ll outsell college grads in six months.
  3. You don’t need to innovate Even though I make a living in “innovation”, there’s a dangerous outbreak of Big Idea Fever. Last night, a few of the participants feared someone will steal theirs. Everyone thinks their idea must be protected like that egg ‘baby’ we carried around in junior high. (I suggest using hard-boiled.) As I’ve written before, it’s almost never about the idea. It’s about execution. A business has to be three things: profitabledoable, andsustainable. No one else will have the passion, expertise, or contacts to drop what they’re doing to steal your half-baked idea. They can only make it better.
  4. It’s under your nose. So many entrepreneurs look for exotic ideas in remote places outside their expertise. Sure, they’re out there. So are others sitting under your nose. They say “write what you know.” It’s why Woody Allen writes about relationships with younger women set in New York (…that only seems creepy in hindsight). It’s also why most entrepreneurs should solve problems they’ve experienced. Last night, my favorite business idea was for a trash removal business. The entrepreneur proposed an opportunity to expand his boss’s business to a new type of customer. The boss turned it down, so he began finding new projects, renting U-Haul’s, until he saved enough money for his own truck. My prediction: he’ll have 10 employees by next year.
  5. Never take learning for granted – I know plenty of people, including me, who “try” or “want” to learn something new. Imagine if your life depended on it. Or, you’re trying to take care of your family for the first time. In that room was a ravenous appetite to learn. Not for some esoteric reason, but to apply it in real life, today. That hunger is missing in so many. Privilege is a powerful pacifier.
  6. Always meet people halfway and help those who do. If someone makes a genuine effort, they deserve your help. And if you want someone’s help, write that screenplay, build that prototype, make those calls. Show you’re serious and others will go out of their way to help you finish the journey.
  7. Community is everyone’s responsibility. Of course, if you commit a crime, you are to blame. But if we do nothing to change conditions that perpetuate crime or recidivism, don’t we own a share of the blame? As the Rush song says,“If you choose not to decide, you still have made a choice.”
  8. Volunteerism is a marathon, not a charade. You’ve probably experienced at least one corporate “volunteer” outing. That’s where a company airs its employees out for a feel-good day of building houses (badly) or feeding the homeless. Then, real professionals who babysat you must spend the next few days fixing your mistakes. All in the name of laundering some donation money through charity theater. It’s far better to give money to committed experts – or commit for the long haul. If people like me don’t stay on, we’re just dabblers, or voluntourists. Take it for what it is – a serious decision with real lives at stake.
  9. Finding satisfaction and purpose is easier than we think. I’ve written some brutally honest articles about happiness. People seem to look for it in all the wrong places – work, gadgets, food. Happiness lives where it always has – with others. Last night started with a lot of strangers hugging. It ended with a form of gratitude that can never reside on Facebook. To get a piece, you have to leave the couch.

My hope is that after reading this, you put down the computer (assuming you were holding it the whole time) and:

  1. Volunteer for (or donate to) Defy or another worthy cause
  2. Do business with companies launched by Defy. (Hopefully they’ll get around to posting links and locations of their successes on their site, as suggested by my friend Dan who also attended.)
  3. Hire or refer someone who deserves a second chance for a job.

One of last night’s Executives-In-Training (EITs) was a 19 year old ex-gang member who grew up with a drug dealing brother as his role model. Another served 26 years. I never did learn for what. He just used a cell phone for the first time. At the end of the night, a few EITs were asked to share how they felt. One could barely express how much it meant to him that we (the executive volunteers) looked him in the eye. He admitted it’s not something he’s comfortable with yet. Another was grateful just to be heard. That we listened to what he had to say like it mattered. It did.

By the end, I successfully fought back a tear or two. Everyone knows macho men…and LinkedIn Influencers don’t cry.