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Jefferson Smith’s young adult life sounds like the setup for John Grisham’s character Mitch McDeere in the movie version of The Firm.
After graduating Magna Cum Laude from Harvard Law School in the top 5% of his class, Smith got exactly what he had worked so hard for – a six-figure gig at a powerful New York law firm. Within the first few days, Jefferson made it known that there was a set of clients that would force him to “conflict out” of representing – Big Tobacco. This is where the movie switches from The Firm to another Tom Cruise movie– Jerry McGuire. Because shortly after Jefferson’s Smith attack of conscience, he was out of the firm.
“To this day, I don’t know if it’s one of the better or dumber things I’ve ever done,” Smith says ironically. “It was probably a good thing… I just didn’t know why yet.”
As it turned out, Smith’s “why” was waiting for him back in his home state of Oregon, where he moved after New York. Smith would discover that his moral compass was not misdirecting him but pointing him toward a life of service that would strengthen American democracy and make the world a better place for many folks.
Two decades later, Smith still lives in Oregon along with his wife Katy and his dog George (named after the main character George Bailey in the timeless film classic It’s a Wonderful Life). Jefferson shares his name with the title character of Frank Capra’s Mr. Smith Goes to Washington.
He’s faced wins and losses, successes and failures. He’s coming off a win – co-founding and selling a health tech company (Tryl) in the clinical trial space.
At 50, Smith looks back at an impressive resume as a social entrepreneur, political activist, startup founder, business consultant, public speaker, national radio show host, and dedicated agent of social change in a troubled world that might need more change agents.
We recently had the opportunity to connect with Jefferson Smith, who shared some insights from his exciting life and career in both the public and private sectors.
What would you say is your greatest professional accomplishment to date?
I have been fortunate to be intimately involved (as a principal or co-founder) in more than a dozen worthy organizations and initiatives, most of which have lived on to thrive and evolve. None of which I did alone. From “Getting on the Bus” in my 20s to launch the Bus Project, which evolved into a national network of pro-democracy organizations, to award-winning nonprofit radio stations, to a successful clinical research technology startup, to SuperThank, and multiple things in between, I have been fortunate to work with talented people and catalyze some innovations that improve systems and help people. And I’d measure my gratification not just by the immediate impact of the projects but by the energy and ability of the people gathered… and perhaps by the longer-term ripples.
With that in mind, the single contribution I’m proudest of would have to be The Bus Project, a pro-democracy organization that changed Oregon. We were then able to scale it to become a national pacesetter. We started the Oregon Bus Project at the end of 2001, which then spawned a host of initiatives and organizations – from PolitiCorps, Oregon Voice, Onward Oregon, the Washington Bus, Next Up, Forward Montana, New Era Colorado, and culminating in the national federation Alliance for Youth Action. It was a wellspring of an immense amount of pro-democracy energy and development.
I keep saying, but it’s really important to understand that my own journey was not just a personal success; anything done that was good represents a collective effort involving numerous individuals committed to democracy and social change. Indeed, just about anything impactful I’ve ever done had more to do with the collective work of other people. That said, given how many leaders were launched, how many people got engaged, and how much pro-democracy policy got moved… there’s nothing of which I’m more proud or for which I’m more grateful than what we germinated when we decided to Get On The Bus.
Can you walk us through your experience running for political office and what you learned?
I learned more than you probably have time and space for. At least, I hope I did. Here are at least a few things:
First, serving the public is a good use of time. I was talking to a friend of mine, Jared, who was serving in his first term in the U.S. Congress while I was serving my first term in the humbler Oregon House. He asked me how I liked it. I told him I had the chance to lead the charge to pass five bills (seven, I think, after the special session). Had I not been elected, it would have taken me everything I had to pass one… maybe two of them. But as a member of the House, I could do 5 (or 7)! That felt like a good use of time. When I asked Jared what he passed in U.S. Congress, he responded, “Oh, in Congress, we don’t get to do bills.”
Second, the system needs more public interest energy. When I decided to run for State Representative, I was motivated by what I saw happening in my district. I lived in one of the poorest districts in the State, a place that consistently got the short end of the stick, and I wanted to advocate for fairness for my neighbors. After I was elected, I learned more about why democracy and governance can be so difficult. Too often, self-interest, masquerading as principle, hijacks the process. Too often, powerful elected officials think first about the special interest groups, second about their colleagues, and third about the general public. And I say that not just to throw stones; I was part of the same dynamic. We need more public interest capacity to flip that dynamic. Democracy needs more democracy.
Third, start by improving as a person and working on problems you care about. People ask me about running for office somewhat frequently – I don’t just mean asking if I ever will again; I suggest asking for advice about their own interests, ambitions, and plans.
Here are two things I offer:
- a) Start by working on yourself. When I lost an election, it was not just because of the forces lined up against me or those I threatened to disrupt but because of my weaknesses, failings, sins, and inability to come to grips with them. So, start by dealing with yourself. Don’t just look at the slivers in your neighbor’s eye; notice the log in your eye.
- b) Pick something you care about and work on it. When I was a law student, I met with Senator Ron Wyden earlier in his service in the U.S. Senate. I asked him about the path to elected office. He told me: “Do something entrepreneurial.” I didn’t immediately appreciate or grasp what he meant; I understand it better now. If you want to lead, lead. Focus not on glorifying yourself but on solving a problem. Convene people to help. Make some progress. Not only will you build leadership muscles, but you’ll also build a set of “friends of the good,” as Aristotle would say. And even if you lose an election, you’ll have worked on something you care about… and maybe done some good.
What emerging trends in democracy and governance do you find significant?
One glaring trend is the increased instability of democracy itself. Since WWII, the Western world has mostly taken democracy for granted. We can’t any longer. Today, we are seeing systematic efforts to undermine democratic principles not just in our country but in many democratic countries, and we need to recommit to those principles as a world.
A silver lining is that there’s also a reawakening, particularly among younger generations, about the importance of safeguarding democracy. This renewed focus is critical to rebuilding democratic institutions. Initiatives like Portland Forward, Onward Oregon, Honest Elections, and the Bus Project – just to name a few where I’ve been actively involved – are aiming to do their part in that very thing.
What’s a unifying factor behind your varied roles in public service and the private sector?
If there is one, I think it’s attempts at problem-solving, sometimes at the edge. That is, seeing a gap that ought to be filled and poking at something to fill it. Sometimes, that has manifested as “innovating at the fringe” or starting from scratch.
And when I’ve done anything well, the unifying factor has been other people.
Aristotle taught that there were three classifications of friendship. Friends of Pleasure – those are friends you like having a beer with. Friends of Mutual Benefit – those are friends who serve each other’s self-interest. And Friends of the Good – these are people who work together around a shared value or objective — or to make the world better. And the highest form of friendship is Friendship of the Good.
I do my best work among other talented humans. Whether it’s the Bus Project, electoral reform, or nonprofit media ventures like The Numberz, the Honest Elections work, or the Innovation Network, even Tryl, the best part has been to gather friends of the good around shared objectives. When we’ve done that well, we’ve had some impact and found some joy.
When I’ve failed, I’ve tended to fail on that score. But I’ve seen firsthand how a group of talented, committed people can galvanize community support and inspire collective action with a multiplier effect. And that’s in a nonprofit setting as well as a for-profit enterprise.
Can you share a moment from your business ventures that you found especially rewarding?
Giving back… directly. One of my most recent projects was called Tryl – a health technology company with the potential for some social impact. I was one of three co-founders, and it was my responsibility to lead the fundraising effort – to ask a diverse group of investors to believe both in the company and in our team.
When the company was successfully acquired, I got to call up each of our 30+ investors, which included some fancy folks as well as some decidedly humble friends and family, and tell them, “I didn’t lose all your money!”…and in fact, I was able to hand them a check a lot bigger than the one they handed me). Generally, in the nonprofit sector, the returns are social improvements or emotional gratification. And this time, it was a genuine thrill to be able to hand something back.
Do you have a professional experience that was particularly impactful for you?
It was when I clerked for Judge Alfred (“Ted”) Goodwin of the U.S. Court of Appeals for the Ninth Circuit after law school. The work required rigor, the subject matter required mental processing, and the output sharpened my writing.
Judge Goodwin passed away in 2022, but his impact on me and all the people who clerked for him lingers on. The day before his memorial service, we had a gathering of his former clerks, which included some amazing people, and we all shared “Judge Goodwinisms” – from the profound to the mundane. It was a reminder of how much he taught all of us.
That gathering had me revisit one particular example he set: he never uttered a harsh word in the chambers, even amid deadlines and in times of stress. It was a lesson not just in propriety but, more importantly, in the value of composure, of maintaining one’s dignity no matter what is going on around us. It established a baseline of behavior and character that makes it possible to weather any storm and come out of it intact. It’s not easy to do, and to be sure, I’m no Ted Goodwin.
What was the worst job you ever had, and what did you learn?
My first job was my worst job – picking strawberries. It’s hard work, but that’s not why it was my worst experience. One time, my brother got reprimanded for using the inside bathroom instead of the port-o-potty. I stood between him and the boss, explaining to the boss that the instructions weren’t clear.
The next instruction from the boss was crystal clear: I was fired. I probably took too much pride in that moment… and maybe learned too little from it.
What is one habit of yours that makes you more productive?
I have a habit of finding and working with people with skills and talents that outpace my own.
What is the one thing you do over and over and recommend everyone else do?
Go to the Public Library. I know it sounds corny, but it’s not. They are one of the great, underappreciated resources in America. It literally hurts me when I see a library get closed. The internet has put massive amounts of information literally in our fingerprints, so it’s easy to understand why people might see libraries as old-fashioned.
But the internet has also diminished the value of something that libraries still offer – a shared experience. We surround ourselves in media filter bubbles, gated neighborhoods, private schools, and segregated political circles. The public library is a social leveler and a community builder. It’s a place where the walls come down.
And in practical terms, It’s also a cost-free and pretty quiet place to work. The quiet study rooms keep the brain from chasing too many squirrels. (And if you procrastinate, at least it’s by getting lost in a book rather than a screen.)
Can you share an impactful travel experience?
I was invited to Liberia to observe and support some democracy work there. Eddie Jarwolo visited the Bus Project, which I started in the United States, and stayed as a visiting Fellow for a year. Upon his return to his native Liberia, he started his own Bus Project and grew a pro-democracy organization in Liberia called NAYMOTE.
Eddie was an incredible host, his team was amazing, and I felt proud as hell to see that the Bus Project work was having an impact on the other side of the world. We met with contingents from the legislative branch and the Supreme Court.
I gave a commencement address to a graduating class of a leadership program for new leaders and elected officials. The topic was “the benefits of avoiding bribes.” While it might seem too obvious, bribes have been a standard way of getting things done politically. Pointing out the upside of not taking bribes is foundational to democracy and shifting the political culture.
I had a chance to see the work and struggle to grow a stable democracy, and it really highlighted how privileged-ridden and small my own work seemed in comparison. And underscored why we shouldn’t take a strong civic culture for granted.
Best $100 You Ever Spent?
Well… I’ll tell you a great $100 I spent recently in the spirit of Fall and Halloween.
For years, my dad imposed a tradition that required trick-or-treaters to deliver some performance – a joke, song, dance, or skit – a trick to earn their candy treat.
My dad’s rationale for putting the poor kids through was, “Otherwise, trick-or-treating would just be begging!”
This was embarrassing to my generation in the family. For years, we were forced to play along with the “no free candy” rule. Finally, after many complaints, we succeeded in regime change. We didn’t oust my dad from his position or from the family, but we did become a typical Halloween family.
So that same year, we had upended the tradition, a 5-year-old girl dressed up as a fairy princess. Holding her mother’s hand, she walked up our many steps and knocked on our door. We opened the door, and she said, “Trick-or-Treat!” Without any demands, we dutifully placed a piece of candy in her bag.
Her eyes filled up with tears. We were confused. Then her mother said, “You don’t understand… she’s been preparing her skit all year!”
From that day, we reverted back to the old rule. No one gets a free piece of candy without first delivering some performance — be it a joke, song, skit, poem, piece of trivia, or dance.
That said, I did impose one change. We give bigger candy now. Since we ask more from the kids, I figured we ought to give more. So now we give full-size candy bars.
My 87-year-old dad still answers the door and prompts the performances. And we urge him not to judge too harshly.
I buy the full-size candy. This past year, it cost about $100. Best 100 bucks, by far.
Who has been a significant influence in your life?
Outside my immediate family, I’d say my uncle, Hyrum Wayne Smith. He was the founder of Franklin Quest (previously Hyrum Smith & Associates, later FranklinCovey), most famous for the Franklin Day Planner. He was one of the finest speakers I ever saw. He didn’t just communicate important ideas. He conveyed wisdom through his words. He could inspire people to become better people.
He bequeathed to me a prized possession – his binder of favorite poems, quotes, scriptures, and anecdotes – material he used for his speeches. (What he called his “I.P. book” – not just as in Intellectual Property, but as in Instant Preparation.) I’m still trying to learn from it – and him.
Are there any books you might recommend to others?
Getting to Yes by Roger Fisher – It’s a practical guide for effective negotiation and conflict resolution. Roger Fisher was a professor of mine, and I was a teaching assistant in his Harvard program, so the book also brings up happy memories.
For something lighter but still insightful, Where the Sidewalk Ends by Shel Silverstein is a great read.
Meanwhile, I should probably read more. Maybe back at the library.
Conclusion
Jefferson Smith, of Portland, hasn’t gone to Washington. He might not be Tom Cruise from either The Firm or Jerry Maguire. But as a gifted speaker, serial entrepreneur, and former lawmaker, he has been a co-founder, leader, and supporter of an unconventional array of impactful projects. Like any leader and disruptor, he’s seen ups and downs.
His startup endeavors, from the upstart nonprofit Bus Project to the clinical startup Tryl, remind us of lessons in innovation and the ripples they can have. His work in civic participation, from nonprofit media to voter registration to Honest Elections, reminds us of the impact a person can have on their democracy. His work with close collaborators, including SuperThank, Portland Forward, and the Innovation Network, reminds us of the value of Friends of the Good.
And only time will tell Where The Sidewalk Ends.
