Ambassador Gordon Sondland’s life is a testament to the power of resilience, ambition, and the pursuit of meaningful impact. Born to Holocaust survivors and growing up in an immigrant family, his drive to succeed was shaped by early experiences with adversity and his unrelenting ambition to do big things. After dropping out of the University of Washington, he entered the world of commercial real estate, and quickly rose through the ranks by reinvesting his earnings and capitalizing on opportunities in bankruptcy deals. His entrepreneurial spirit eventually led him into the hotel industry, where he made his mark. He was an early adopter of boutique hotels with his business partner and mentor Bill Kimpton. Long involved in politics, often as a liaison between Republicans and Democrats, he officially entered international diplomacy as U.S. Ambassador to the European Union in 2018. Along the way, Sondland navigated the complexities of business, politics, and philanthropy, always guided by a belief that building real relationships creates powerful results. From his diplomatic role during the 2019 impeachment proceedings to his ongoing philanthropic efforts, Ambassador Sondland’s career is a blend of passion and commitment, grit and humor, and an unyielding dedication to making a difference on the global stage.
Could you give us a brief overview of your background and what led you to where you are today?
I’m a first-generation American. My parents both escaped Nazi Germany, survived the Holocaust, and had me in the United States after becoming U.S. citizens themselves. I have a sister who is 20 years older than me, so I was definitely a surprise. I grew up in an upper-middle-class area but was lower-middle-class myself, and that difference, which I lived every day, fueled my drive to succeed. Never a conventional thinker, I spent two years at the University of Washington before dropping out to go into real estate, and I never looked back.
How did you get your start in commercial real estate?
I couldn’t get a job without a college degree, but real estate brokerage companies back then didn’t require one as long as you could make deals. I started at a regional brokerage company selling small apartment buildings in the Pacific Northwest. I didn’t know what I was doing but I did know how to talk to people and convince them of things. And I was good at saying “The price is too high!” which is what you automatically say when someone is selling you something. From there, I learned fast, lived frugally, and reinvested my commissions in the buildings I sold, building equity over time.
How did you pivot into the hotel business?
I was running a division for a regional company and one of my brokers brought me a hotel in bankruptcy. I knew little about hotels but had experience with bankruptcy-related deals. The property was in a prime location but boarded up. Instead of selling it to a client, I decided to buy it myself, raised funds from investors, and that became my first deal in 1985. This fueled a syndication of other hotels both branded and independent and along the way I formed a hotel management company called Provenance.
What inspired you to shift from business to politics?
A mentor in Seattle involved in the Republican Party exposed me to politics. Through him, I met President George H.W. Bush and became involved in his network performing low level tasks like making coffee and driving people around. I realized that everyone involved in politics that wants to work their way up the food chain starts at the bottom. I was part of that tradition. I also noticed that successful businesspeople appointed as ambassadors found the role deeply rewarding. I wanted to pursue that path but it’s not an easy one to navigate. I spent decades figuring out how to get there.
What were some of the most important moments during your tenure as U.S. Ambassador to the European Union, and how did your background as a political appointee shape your approach to diplomacy, especially when compared to career diplomats within the State Department?
During my time as Ambassador to the European Union, there were several key accomplishments that I’m particularly proud of, each of which contributed to strengthening the relationship between the U.S. and the EU but even more importantly aggressively advancing the interests of the U.S.
One of the most significant achievements was working on trade agreements, particularly the efforts to create a framework for transatlantic trade that took into account America’s desire to tilt the advantage the other way. I played a central role in pushing for an agreement that focused on reducing trade barriers and fostering economic cooperation between the U.S. and European nations. We were able to make real progress on this front, opening the door for more opportunities for American businesses in Europe.
This work as ambassador made clear the critical role that political appointees play in diplomacy. The media often paints political appointees as unqualified or as outsiders with no real understanding of international relations, but that’s a misconception.
Political appointees, like myself, often bring a different set of skills to the table, different, but valuable. My background as a business leader gave me a distinct perspective on how to get things done, especially in situations that require fast decision-making, strong relationships, and a willingness to make deals. Political appointees are more likely to have direct access to the president, which means that we can bring issues to the highest level of decision-making, quickly.
That’s not to say that career diplomats don’t play a vital role—they absolutely do. They have years of experience, deep institutional knowledge, and an understanding of how to navigate the bureaucracy. But there are times when having a well-connected outsider can move the needle, especially when it comes to securing deals or pushing forward an agenda that requires speed and direct influence.
The differences between political appointees and career diplomats are not about qualifications but about perspective and approach. Diplomacy is about knowing the rules and procedures but also how to maneuver outside of those structures to get things done in a way that benefits the country. I believe that, at times, political appointees can bring an efficiency and pragmatism that really helps move things forward swiftly and effectively for the good of the country.
To serve effectively, what qualities do you think public officials need?
You must be in it for the right reasons. Some people become intoxicated by the trappings of power rather than focusing on their mission. The most effective officials use their access to leadership to drive meaningful outcomes rather than enjoy the perks of office.
Your role in the 2019 impeachment proceedings put you in the public eye. How did you navigate that period?
It was a difficult time, both personally and for my business. I lived in a liberal-leaning community in the Pacific Northwest where the assumption was that I was complicit in wrongdoing. In reality, I had no personal agenda—I was just doing my job in Brussels. There were people in the Administration who had the goal to undermine President Trump. The impeachment process was aimed at undermining his momentum, even though the so-called controversial phone call with President Zelensky was, in my view, completely benign.
Do you regret the personal impact the impeachment had on you and your family?
It was tough on my family. Looking back, there was nothing in that call that warranted impeachment, let alone conviction. Given what we know about the Biden family’s dealings in Ukraine, Trump’s concerns were justified.
What global challenges concern you most today?
China is one of my biggest concerns. The average American who loves buying cheap Chinese products does not understand how sinister the regime is. The public doesn’t understand that we’re already at war with China—not kinetically, but in terms of intellectual property, education, and military buildup. The U.S. needs to take a more aggressive stance to counter China’s influence. The World Trade Organization should not be treating China as a developing nation as they have been a developed nation for decades and have the world’s second largest economy.
What steps do you think the U.S. should take against China?
We need to be draconian. That might include limiting Chinese students in our universities, cutting information-sharing, and completely disengaging before renegotiating engagement on our terms.
Before diplomacy, you built a successful hospitality business. What lessons from that experience shaped your approach to public service?
I learned from my mentor and business partner Bill Kimpton, a pioneer in boutique hotels. He believed people wanted an experience, not just a room. That lesson—creating something memorable—applied to diplomacy as well. It’s creating moments and discussions between people that they will remember positively. Relationships matter.
What role did your family play in shaping your career?
My parents taught me grit like only those who have experienced real adversity could. My pregnant mother sailed from Europe to Uruguay, a country she knew nothing about. She didn’t speak the language and had to work while pregnant in a clothing factory. Having to separate from my mother for her safety, my father evaded the Gestapo and joined the French Legion. He worked on a railway for two years and fought alongside the British Army in Myanmar. He had no country, no home, no possessions, no money, but he had grit and he had a strong moral compass. Years later, my brother-in-law, Herb, was a big influence. He was successful, hardworking, and believed in ethical business. He showed me that you don’t have to exploit others to succeed.
How have you passed those values to your children?
I believe I have and I love watching my kids thrive in business and life. My kids work in private equity and venture capital, and I’m proud of their values and work ethic. Their grandparents would be too.
Are you looking at any new hotel ventures, particularly in Europe?
Previously, I operated a hotel management company across 12 states, which I later sold. The company now merged with another business that operates nearly 200 hotels in almost every state. I sit on the Board and am a significant shareholder, so I’m always looking to increase shareholder value there too. As far as European investments are concerned, having them on my radar is more recent, but having served there for a few years, I have a good feeling for which markets are likely to experience growth and provide robust returns.
How would you describe the relationship between business and government?
It’s evolving fast, especially with Trump back in the White House. It’s no longer just about regulation—it’s about collaboration. Government should open doors, ensure fair rules, and support initiatives that benefit society while allowing businesses to thrive.
You’ve been active in philanthropy throughout your career. What led you to start the Sondland-Durant Foundation?
My sister and brother-in-law were big philanthropists and set a great example that I have tried to follow. Giving brings me more satisfaction than making money. I focus on tangible results and it’s great to see my donations having an impact across sectors including funding entrepreneurship as we did with donations to Duke University. Also, to medical research. It’s incredible to witness results of cures that I have helped fund. I believe in what Benjamin Franklin once said, “An investment in knowledge always pays the best interest.” I may be a college dropout, but I understand the value of education for all.
Can you share a philanthropic initiative you’re particularly proud of?
Sponsoring the Auschwitz exhibition in 2023 at the Reagan Library. It was one of the most attended exhibitions in the library’s history and helped educate thousands about the Holocaust. We have so few Holocaust survivors left, but we have to continue learning about history. It must be both, “Never Forget” and “Never Again.”
Looking back, what moments stand out as turning points in your career?
Becoming an ambassador after decades of effort was a personal achievement. More importantly, realizing that I could genuinely move the needle for U.S. interests was incredibly rewarding. In Brussels there was a wall of formal portraits of the twenty U.S. ambassadors to the European Union. The first nineteen had incredible educational backgrounds, many having more than one Ivy League degree. Number twenty, that would be me, was the only dropout.
How do you hope to be remembered?
Well, I’m still in my sixties, so I hope I have a lot of time left to discover and perhaps serve my country again. But when I look down the road, I don’t focus on legacy, but on setting a good example. I want my children to believe they can achieve anything, the right way, and they’re already showing that mindset.
What are some of the biggest changes you’ve seen in business, politics, and philanthropy over the years?
Technology has accelerated everything. In politics, traditional diplomacy is giving way to more direct, results-oriented interactions. In philanthropy, there’s a growing focus on efficiency and effectiveness—poorly run charities should disappear so that effective ones can thrive.
Your book “The Envoy: Mastering the Art of Diplomacy with Trump and the World” offers a detailed and personal account of your time as U.S. Ambassador to the European Union, but it also delves deeply into the broader dynamics of diplomacy, leadership, and the personal challenges you faced. What ultimately motivated you to write this book?
The motivation came from my desire to share an honest and behind-the-scenes look at what it’s really like to serve as an ambassador during such a pivotal time in history. There’s so much that the public does not see including how policies are shaped, how personal values intersect with professional duties, and the human side of navigating the complexities of international relations. It’s not just little flags on desks, lots of sparkling water consumed, and months of frustration. I wanted to provide an unvarnished account of my journey, not just to reflect on the challenges and controversies I faced but also to highlight the broader lessons in leadership, resilience, and diplomacy that can be applied in any field.
What is one of the most memorable moments you had as ambassador that you recount in “The Envoy.”
There were many, but one that I think about often, because it showed the kind of effective, speedy, and offbeat diplomacy that President Trump likes to practice—and that politically-appointed ambassadors are often good at—is when we negotiated with German car manufacturers. In 2018, the EU was unwilling to make any material concessions to help reduce the deficit between us. One of the biggest offenders was German cars, which Americans buy a lot of. Trump had an idea to go directly to the German car makers, do a deal with them, and bypass the EU and its red tape and regulations. He brought them to the U.S., invited them into the Oval Office, and made the meetings impressive because of the White House, yet casual because of Trump’s demeanor, and very impactful. And at the end of it, we’d negotiated with the three largest German car manufacturers to build factories in the U.S. and avoid tariffs. I was really proud of that.
It’s a very candid book. It reads very much like you speak: unscripted, humorous, no holding back. What do you hope readers take away from it?
First, I want them to gain a deeper understanding of the intricacies of diplomacy, the importance of building relationships, and the difficult decisions that diplomats and public servants must make on a daily basis, as well as how to use your position for meaningful impact. Second, I hope readers walk away with a better appreciation for the complexities of the political world—how things are not always as they seem from the outside—and the importance of maintaining integrity, even in the face of adversity. Above all, I want my book to inspire people to think critically and work for what they believe in, whether in their professional or in personal relationships.
Ambassador Sondland’s best-selling book “The Envoy” can be ordered online at https://www.amazon.com/Envoy-Mastering-Diplomacy-Trump-World/dp/1637585284
