There’s an old folk tale of a man who was a very clever smuggler. Every day, the smuggler would come to the border with his donkey and the official there would say, “I am pretty certain you’re trying to smuggle something.” And every day, the officer would pull apart the donkey’s bundle—but find nothing of value. This went on for 15 years. Eventually, the border official retired. One day, he happened to meet the smuggler at a marketplace. The retired official begged him, “Please, just tell me. What were you smuggling all those years?” The man replied, “Donkeys.”

Jeff Buenrostro is like that donkey smuggler. His interactive group programs “smuggle” consciousness, cognitive behavioral therapy, and personal development to people who have sentenced themselves to the corporate rat race. And he works with men who have been sentenced to do time in prison. In both environments, he works in “containers” in which people: face fear, failure and inadequacy; heal old wounds and traumas; and become the optimal version of themselves.

I know Jeff through my son Jake. The two young men first met in the Beta Theta Pi fraternity at Vanderbilt University. They had a shared interest in creating change in the world and joined each other on international development projects like rebuilding Buddhist monasteries in Mongolia and education projects in Africa. Jeff had previously worked on the issues of affordable housing and energy in the non-profit world. While working in Mongolia, he met someone in the biofuels industry, which led him to work in the biodiesel world, which led to alternative energy work in venture capital. It was only then, after travelling and exploring the world, that he decided to go to Stanford to study at the Graduate Business School and the Institute of Design.

I don’t think Jake ever understood why Jeff turned to academia. In a conversation I had with Jeff in 2020, he told me, “I’ve always been fascinated with people and the psychology of organizations. I just wanted to know what I was really good at and really passionate about. Learning about design thinking changed my life. And when I started to work on healing my own childhood wounds and traumas, it dawned on me that I could combine my passion for personal growth and organizational change. My work in the world is around healing and ‘smuggling donkeys’.” In addition to his MBA, Jeff eventually got certifications in cognitive behavioral therapy, addiction recovery coaching, and psychological spiritual integration coaching.

With his new MBA in hand, Jeff was hired by Meltwater Group, a raging successful global software company, to start an incubator for their next product. After finding an interesting gap in the digital marketing space, he architected and incubated a business for Meltwater. In 2012, the company stopped funding the startup. That day, Jeff and three others took it over and co-founded Metric Theory.

As the COO and CPO, Jeff’s used Metric Theory as a petri dish to run “social experiments”, literally smuggling his personal development work to 20-somethings inside corporations and discovering what worked (check out his key learnings below). By 2018, Metric Theory had made Inc.’s 500 list and Entrepreneur’s Top Company Cultures list. By 2019, they were one of Inc.’s Best Workplaces and Search Engine Land’s Best Agency of the Year. In 2021, Metric Theory merged with MightyHive and S4Capital. Metric Theory now operates as Media Monks, a global media company with over 10,000 employees. As the Global Senior Vice President of People Operations there, Jeff is now working on strategic projects, one of which is leading the buildout of a global coaching program for all employees to work on personal and professional development.

As things were taking off with Metric Theory, Jeff began smuggling his unique form of conscious healing work into the non-profit space. (Full disclosure: Jeff has sat on the board of my non-profit Cultivate the Karass since its inception in 2016.) In 2018, Jeff joined the non-profit Inside Circle as a board member to work with incarcerated and formerly incarcerated men to heal communities in the United States. Working inside New Folsom Prison with mostly “lifers”, he began experiencing empowering “circles” in which inmates and outsiders could heal their trauma and anger, find purpose, and build meaningful lives. From the get go, the inmates made it clear to this founder COO that they were running the show.

“If you came here to help or save us, get out. If you came here to show us where you struggle and how your existence is connected to ours, join us.”

He stayed, learning from the men what he had come to the prison to discover. They, like him and many others, came from a place of trauma: he was there to learn by sharing his experience and witnessing theirs. Over time, many of the inmates trained to become healing circle facilitators qualified to work inside and outside the prison. One of them, Eldra Jackson III, was inside Folsom serving multiple life sentences. The inner journey he began in those circles eventually led to his rehabilitation and a reduction in his time to 24 years. Now outside, Eldora is Inside Circle’s Executive Director, as well as a mentor, facilitator, advocate and public speaker for at-risk youth and effective criminal justice rehabilitation.

Key Takeaways

I’ve pulled the following wisdom on being a pioneering leader from conversations I have had with Jeff in the last few years.

1. Develop self-awareness. You are going to be more successful in your career and your life when you know who you are—especially when you understand what your wound is and what you’ve built to protect yourself.
2. Iterate on everything you release. Look at what the real need is. Design something to meet that need with the understanding that, 99% of the time, what you first put out there is never going to work. Keep iterating. Keep thinking.
3. Take yourself out of the picture when necessary. Recognize that sometimes a “credible messenger”, someone who looks like the people you are trying to connect with and who grew up in the neighborhoods they did, can do a better job of communicating than you ever can. For example, if you’re a founder CEO, send in an analyst who worked her way up the ranks or a formerly incarcerated man who has served 25 years and doesn’t give a s**t about what you think about him.
4. Build social contracts with employees. Instead of signing actual contracts, come back to people after a year or two of working with you and, together, design an agreement outlining what the business needs from them and what they need from the business over the next year and half to two years. Six months before the agreement is up, reconnect to either create a new contract or transition the person out. Understand some people will break their contract, especially if they don’t have feedback on their performance and visibility into their career prospects.
5. Accountability is essential for changing people and systems. The likelihood of individuals and groups succeeding is very small if they are not held accountable. In groups, develop strong peer-to-peer accountability practices around making commitments, creating smart goals formalize them, following up, and charting progress over time. Invite individuals to create their own personal board of directors to hold them accountable for the things they’re doing.
6. Create intentional communities inside your organization. The dynamics of an organization shift as you grow. When you reach 25 employees or so, the drama starts. Get agreement on the fundamentals, the values of the culture. As you open the doors more, be like Burning Man. Allow communities to form. Use facilitated circle work to keep these communities alive and to do work around unhealed issues like the gender divide. Let them be dynamic collections of all the individuals there. Let each community figure out how to maintain the core values of the organization while also incorporating their own desires and values. Gather monthly surveys from these small groups to identify what needs to be addressed next.
7. Invest in “the whole person”. Not only invest in your people’s professional development. Invest in their personal development. If you create a culture of personal growth, the bottom line will grow. The more a person knows themselves and operates from a place of awareness, the better team member they will be. The better the individuals on a team, the better the team will be and the better the team’s output. The better the team’s output, the better the company results. If the individual’s compensation structure is tied to the results of the company, then this all comes back around to benefit the individual.