How One Entrepreneur's Rollercoaster Ride Transformed the Digital News Landscape

Rick Stamberger is the co-founder and former CEO of SmartBrief, which publishes more than 200 newsletters reaching over five million executives. Stamberger founded the company in 1999 with Tom Wheeler and Dan O’Brien and ran it for two decades before selling the company to Future Plc.

I grew up in Poland, Ohio — a small town near Youngstown, which was a steel mill city. There was smoke in the air, but it wasn’t pollution; it was profit. The mills were working.  Poland was a quintessential small-town America and probably closer to the 1940s than the 2020s in many ways.

My dad was a sales manager at a steel company. Something happened in terms of office politics that I never completely understood, but he took early retirement at 50. It turned out for the better because the company went bankrupt a few years later. His experience convinced me that I never wanted to work for a big company. I don’t think I’m vindictive or hateful, but I never forgot slights against my parents.

We moved to Sarasota, Florida, and one year later, I moved to Washington, DC, where I went to Georgetown Prep. It’s more famous now because two sitting Supreme Court justices and the Chairman of the Fed went there. Not bad for a small boys' school. I was a Protestant in a Catholic school run by Jesuits. They certainly had an impact on me — they taught me to write as I speak, and they encouraged my interest in politics. I served as president of the student body and graduated in 1977.

While at Prep, I volunteered for President Ford’s campaign in 1976. I would get on the Rockville, Maryland, bus and head down to the election committee headquarters. I would help manage the phone banks for Pennsylvania and then take the bus back to study for history class.

I went to Northwestern University thinking I wanted to be an actor or politician, which is the same thing in many ways. I took a semester off after freshman year in 1978 and joined the congressional campaign of John Porter, a Republican, in Evanston. We lost by 500 votes, but John went on to win shortly thereafter and served for over 20 years.  I’d decided to leave Northwestern and headed to Williams College in January of 1979.

Over the years, I’ve met several people who set my career trajectory. One was Jan van Eck, the head of VanEck Funds. Jan was five years younger than me, and we met in Williamstown in 1985 after I had given a talk. We met again in Washington, and years later, he invited me to join the board of the VanEck mutual funds.

After graduating from Williams, I went to Los Angeles as a Coro Foundation Fellow. When the program ended, I thought I would go to law school.  A friend and mentor suggested I meet Rita Hauser, a prominent attorney when I was in New York. He told her husband, Gus, then head of Warner-Amex Cable, that I would be a terrible lawyer and needed a job. Gus told me I should go to work for Tom Wheeler, the President of the National Cable & Telecommunications Association.  I believe he told Tom that “you need to hire this kid. He’s from Ohio.” Gus was from Ohio, and so was Wheeler.

I had no plans to work for a trade association, but that one drink set 40 years of my life in motion. Tom and I later worked together at another company, and he was a co-founder at SmartBrief.

I started work at the NCTA in 1983 as the industry was fighting to be deregulated. It was exciting to be there, and I had a ringside seat. It was the entrepreneurial heyday of cable. As executive director of the PAC, I met with big personalities like Ted Turner, John Malone, and Bill Daniels.

Next, I applied to the White House Fellows program. I went to work as a special assistant to Vice President Bush. I think back on these years and marvel at what I would pursue, unburdened by fear and doubt. At 23, you don’t know what you don’t know. I found that I could pick up the phone and call anyone, and they would take a call from the White House.

One experience in particular paid off later. Craig Fuller was then secretary to the Cabinet, and he asked me to reach out to contact all the cabinet agencies and create a weekly briefing for the president. For a 23-year-old, this was a great project!  It didn’t go far, however. Craig told me that Ed Meese, the counselor to the President and his close friend, said that it was his job to brief the President, which he did daily off a 3x5 card.

But that little exercise put me in the knowledge business and got me to focus on how people could learn and absorb information.

I learned a lot by watching Reagan and Bush. Reagan didn’t have a problem surrounding himself with very smart people because he always knew he was president. He had quiet, deep self-confidence.

As I was leaving the White House, I realized I didn’t want to be in politics and impoverished. I could stay in the Administration, or I could do something else. I asked three people for advice, including Bill Donaldson, the co-founder of DLJ.

Donaldson said: “I’m going to tell you what you don’t want to hear. You need to go to business school — and you should go to Harvard, Yale, or Stanford.” I ended up at Harvard.  At 26, I was one of the older students in my class.

During our second year, two classmates and I decided to buy a chain of dry cleaners, which we planned to expand nationwide. Bill Donaldson was our investor. In the end, the deal fell through, but it became the topic of my commencement speech, “I Could’ve Been the King of Creases.”

I left business school with a new business partner, Dan O’Brien. Dan had been at Brown Brothers before graduate school and was the “brain” as we built SmartBrief.  For ten years, we did a lot of consulting in the for-profit and not-for-profit spaces before starting the company.

I’ve won by surrounding myself with people who are smarter than me. You can never be the smartest at everything.

Shortly after HBS, I seemed to hit a plateau. My career had been surging, and then suddenly, I couldn’t figure out what to do. I had this pedigree, but  I just wasn’t getting much done. I was surprised when I was diagnosed with ADHD. I won’t say it’s always been easy for my colleagues or me, but I’ve tried to address the challenges while seeing the advantages.

At this point, many of the things I’d worked on came together as we launched SmartBrief. We took the idea of a clipping service from the White House and created a digital news service for industries. We created partnerships with trade associations to build audiences.

We owned the data from the email service, and the trade association membership lists gave us an immediate audience. Along with a co-branded, highly valued service to their members, the associations received 15% of ad revenue. I pulled the 15% revenue number out of the air.  I had no idea if it was good.

The management book that impacted me most was “The Inventor's Dilemma” by Clayton Christianson. It was my Bible for creating SmartBrief. I was also influenced by several cases from Harvard Business School about Honda and Southwest Airlines. Specifically, Southwest only flew 737s, and Honda built six perfect cars. That contrasted with companies that had extremely complex systems. I liked the idea of making something simple and easy.

My idea of leadership was to hire great people who were smarter than the CEO. I wanted to set the direction and get out of the way. To inspire but hold people accountable. Communication was important. Every week I wrote a piece to the team, shareholders, and trade association executives sharing updates and subscriber numbers. We put it in a SmartBrief format.

We built a ‘strong, loose culture,’ which is something I experienced at Williams. It wasn’t based on wearing the right colors or showing up in a particular way. But I looked for smart and positive people, and they would then hire their friends. The first heads of sales and tech were recent Williams grads.  I think you hire what you know at the outset of a venture.

We sold the company in 2019. It was the right decision, and I don’t look back with regret. I was ready for a change, and the company needed new growth opportunities and a structure where I wasn’t at the center.