Jim Wilkinson, executive chairman of Trailrunner International, recounts his unplanned journey from a small Texas town to the highest levels of government and business. Growing up in Tenocht, Texas, he initially aspired to be a funeral director but accidentally entered politics after an internship with Congressman Charlie Wilson and later working for Dick Armey. He highlights that in government, “the person with a proposal wins every time” and that logistics and management outweigh tactics. During the 2000 Florida recount, he participated in chaotic, media-savvy tactics like renting costumes to influence coverage. At the White House, mentors like Karen Hughes taught him to always give unvarnished opinions, while Condoleezza Rice instilled intellectual curiosity. His time in Iraq during the war profoundly affected him, making him anti-war and prompting a desire to leave politics. He eventually joined the Treasury Department under Hank Paulson, expecting a quiet role, but was quickly caught in the 2008 financial crisis when the commercial paper market froze. Wilkinson emphasizes Paulson’s early foresight and leadership as vital. His career, shaped by luck and mentorship, underscores the importance of management, directness, and learning from crises across public and private sectors.
Welcome to Decision Makers, the podcast featuring conversations with leaders at the highest levels of business government media that explores how they made it to the top and what they learned about how decisions are made being there. I'm Matt Kalmanz, together with Sasha Samaton, the co-founders and co-co-seos at Apple Cart, and today we'll be talking with Jim Wilkinson. Jim is the executive chairman of Trailrunner International, a leading C-suite advisory firm. Jim began his career working on Capitol Hill and later in senior roles in the Bush administration under Condoleezza Rice and Hank Paulson. The later transition to the corporate world where he led communications at Pepsi and corporate affairs at Ali Baba during their IPO. His experiences behind the scenes during the Iraq War, 2008 financial crisis, and some of the most anticipated corporate transactions, give him a great view into how decisions are made at the top at the highest levels across both the public and private sectors. Let's dive in. Jim, welcome to Decision Makers. Thanks for doing this. We like to start by understanding where our guests come from. So can you tell us a little bit about your upbringing in Texas and how you ended up beginning a career in politics? Well, like everyone, first of all, excited to be here with you. I didn't plan it. You can't really plan your life. Life doesn't happen in linear fashion. I grew up in Tenocht, Texas, which is an Indian, means muddy water. It was around on the border of Louisiana, not that far from the Alabama, Kishada Indian reservation there. A little time with a thousand people and wound up completely accidentally. My congressman was Charlie Wilson. Charlie Wilson's war and wound up who was quite the figure. And then wound up working for a guy named Dick Army, Republican and home from there. But I was an athlete in college and completely and totally my whole dream was to be a funeral director and own a funeral home and do that and wound up in politics. How did you go from a funeral home to working for Dick Army in Congress? How did that evolution happen? Just total luck. I got an internship and then wound up going to DC and eating macaroni and cheese and ramen and starving the death like everybody at the time. What money I had, I spent on beer and food and tortilla coast right there right in the house. I think it's still there. Yeah, but you know, you can't plan these things that you know, I applied that's back before the internet. So you actually went to a library and checked out a book and you wrote letters to congresspeople asking for jobs and sometimes they called you back and sometimes they didn't and he did. Well, that was a good person to have return your return your letter. So what did you, while you were working for Dick, what, what did you learn about how decisions were made in government from the purchase working on the house side? The most important thing I learned that was at a time when Democrats and Republicans actually talked to each other. When Dick became a Jordi leader, one of my best friends, you know, George Stephanopoulos had been a floor assistant for Dick Gethart and I got to know him a little bit later. Great guy, but one of my best friends was Dan Turton who actually just died. Dan was a floor assistant with Gethart, a dear virtual friend. You know, Democrat, he sort of took me under his wing and really, really helped me. But the biggest thing I learned is the person that has a proposal wins every time. And what Dick was was a great leader in terms of certainly economic thought and philosophy. It was also a great manager. And I learned the saying amateurs talk tactics and professional stock logistics. Anyone can pop off and say whatever, but actually manage something to do a policy process. It takes management. I just became in love with large numbers of people working together to attack a problem. And how did you end up transitioning to the NRCC and starting to do more of that was on the campaign side? You know, I worked at that time, Dick Arming became a Jordi leader and you have a leadership pack. And what you do is you give money out to members of Congress who are running in hopes that they will vote for you for a Jordi leader. Because between the election day and then when Congress starts, they have a private election from, you know, Speaker the House, Majority Leader. And so, and so I knew all the political races around the country because, you know, typically a senior person in Dick Arming's office left for a year and then did that, right? You went and worked all the campaigns. He traveled around, raised money forms, happens today still with, it's pretty common. Democrats and Republicans. But, you know, I just wound up at the NRCC. It was a, it was a presidential year and wound up going over there to help them. In that case, we were trying to retain our majority. You know, it was Bush versus Gore and it was going to be a street fight in a close election and we had to make sure we'd retain that House Majority. And at some point in there, you took a trip down to Florida to help with their recount, right? And so did it play out just like in the movie? I don't know. There have been so many movies made, but what I'll tell you is that you had a bunch of people who weren't Florida, who's down there working in all kinds of mentioning things. I mean, one funny story that we actually rented, costumes, you know, like the John 316, out of the wig and kings and queens and marched them behind the cameras to try to de-legitimate as the process. But it was a street modem down there and you had the very best on the Democrat side and the very best on the Republican side fighting for what, you know, wound up being a few votes to win there. But yeah, it was down there when they had the Brooks Brothers riot and it was all across Miami and all over Florida. And it was a steam group of people that were working on that that ended up in all kinds of interesting places later on, right? It wasn't Ted Cruz was down there. There were a whole bunch of folks that were involved in the recount, right? It's funny. They had a, at that time, they had this, they called it the Warwagon. It was this big RV. That they drove around places and the media was just convinced it was like this secret command center. There was nothing in there. It was like, "Nothing." Like, nothing. I think we had, you know, probably, I'm sure they went to Dr. Pepper because I'm a Texan. I love Dr. Pepper. That was too high. And I'm not a Texan. It was, but it was just the sinister thing that the media covered is, you know, there it is, the Warwagon, you know, and, you know, it was just full of members of Congress and people wanted to be down there, you know. But at that time, it was the biggest thing any of us had ever seen. You know, the Clintons had been in power for eight years. We didn't, you know, none of us ever been in the White House, you know. So it was just, it was just a fun thing to go be a part of. It's sort of, you know, and it's like our version of the military, you know, going and being involved and being a part of the biggest political thing happening. And so how did it transition? So you get through the recount, Bush prevails. How do you end up in the White House after that? Did you get a call? Yeah. So I'd go to grad school at night and I'm also a military officer. I'd been a reservist. And I, they, at that time, you know, the Bush team didn't know a lot of people in DC. They're governor of Texas. And so they have to build confirmation teams. And I worked a lot in Congress. So they put me on the confirmation team, given my vast experience of, I think, at that point, two years and military reserves. And so to help them get confirmed. So, you know, you go with these cabinet secretaries to be, this is during the transition, you go around meet senators, you grovel in their offices, ask them for support, listen to their views, and then hopefully they vote for you for confirmation. And so it was just assumed that I guess I'll go work at the Pentagon, right? I'll go find some job somewhere over there. And then, um, Rumsel and I really hit it off. He's dead now. God bless his soul. But about three days before you know, aggression, um, Rumsel, like, cut me off, wouldn't talk to me anymore. And it was really odd. And then I get a call that, uh, Dan Bartlett and Karen, he used to like to meet. I met with them. Um, and then they called and offered me the deputy director of communications job. And the White House, I was making 120,000 a year at the NRCC, um, that job paid 60 grand a year. I was like, I don't know if I can afford this. It's like, it's like, you're going to go playing the NFL, but it's a per compensation. They made it up to you later in life. Yeah. And then forget, um, they call me and say, let me think about it, which I call my parents, like, you don't think about the White House. You go to the White House, right? So I called them back and then it was funny. The next day, Dan Bartlett, come and say, Hey, you know, you've been working for us for a day now and you've gotten the raise every caliber. So we got, I got like, I think raised from 60 to like 70, but my point is just, it was an honor to work for President Bush and the team. But, but, you know, you just, you know, you get that call. You go play for the league minimum wherever you can. You don't care. You just want to get in the White House. So, um, and we were off to the races. So you talked about Karen Hughes, Dan Bartlett, um, people that, uh, we're doing and went on to do great things. I mean, who, who are your most important mentors at that time? Yeah, who are the folks that sort of taught you the ropes as you were coming up through the White House? Look, I think first off, Karen, he's is incredible. Um, she was someone we all respected. She's just larger than I figure, but she, you know, a mom, uh, but just a, a, a great, just leader and great counselor. And when she left the White House, she gave us all a piece of unvarnished wood that had the presence of seal on it. And I still have my insinu my desk at home and it said always gives, you know, thank you for always giving us your unvarnished opinion. And I think that's important. I learned from her just to call it like it is. Dan Bartlett was another one, you know, Dan had worked.
for Governor Bush for a long time, Dan's is still a dear friend. I hold him in high esteem, great respect with him, you know, for him. He was another one that was really became good. Kindly he's a rice, became a, wound up becoming a great personal mentor of mine. Even today, Godmother to my daughter, Josh Bolton was another one, Joe Kaplan is someone, Kristen Silverberg, he's not household names with these are people that are, you know, serious thoughtful leaders, who I just looked up to and respected Joe Hagan, who's deputy chief of staff with someone. So just, you know, the people, you know, Democrat or Republican, whatever your politics, these are hardworking people that, you know, we all shed blood in the same mud together and I have great respect for them. There's a few of the folks like that. Andy Card was another one. - And so Karen taught you to shoot it straight, or at least reinforce that instinct. What were the other things you learned from some of those other people that have been useful to you even today? - You know, the power of the visual, you know, Scott's forza was our person there who really worked on the president's visuals. I think that was, I learned a lot from Scott there. I think the power of logistics, you know, Joe Hagan and Andy Card as chief of staff and deputy chief of staff were on a very tight ship on logistics. I brought those lessons forward. You know, most people can't manage anything and watching their great management prowess as a CEO now, I take a lot of lessons just about managing things and, you know, no wasted motion, every penny of prisoner or watch what you're doing. I think, just like I think President Obama's house or White House as well run as well. At that time, I remember when the Clintons first came into power, I learned from one of their people that they didn't have a schedule for like weeks. They were like, "What even gonna be the day when we wake up?" Right? And so, I learned just some of those strong things. You know, from Connelly's to Rice, I learned, you know, we need to be intellectual curious and she is. You know, she says, "There's no reason why a black woman "from Alabama should have wanted to learn Russian "and become a Russian specialist," but she did. And so, you know, one of the tragedies of this current political climate is we've made being an intellectual, like not cool. And I don't claim to be an intellectual like you, Matt, or you, Sasha, but what I'll tell you is that, is that knowledge and reading and learning are important. And I was around people that sort of pushed those things. I remember many times, trading book ideas was a present of Bush. You know, he was obviously someone we all look up to and respected. And you know, one of the great tragedies is people don't understand how big an intellect he is 'cause he was constantly reading and referring books to us and things. So, those are a few lessons. - What was the best book that President Bush referred to you? - There was a great book on, I got called, "Gaddest," which was about terrorism at the time. It really was looking at it from a thoughtful intellectual perspective and how to approach it. And I remember that, that was one he recommended. - Great. And so during the Bush administration, you play a lot of different roles, but one of them was a key communications role on the national security team during the rock war. To this day, what do you think was least well understood by the public about what was gone on in the White House during that time? - Look, I think that, look, I was a military officer, my brother was enlisted served on the front lines of the rock war, so obviously I took every day of that very seriously. I think what's most misunderstood is the degree to which we had not been graded intelligence for a long time as a country. And you know, it wasn't about connecting dives, we needed more dots to connect. And so when you look at 9/11, Afghanistan is a place where you typically lost. The Russians had lost there. If you go back thousands of years, people would go in Afghanistan and lose there, right? From a historical perspective. And so we won there. Our teams did a great job and we had this great global consensus. But at that point, you know, if there were flat planes in the building, and they'll certainly use biological weapons, they'll use chemical weapons. So now I'm saying, you had to use chemical weapons against the Kurds and the North. So at that time, there's pretty much personal consensus that you had to go. And one of the great tragedies is that they all turned out in a way I think, which is, we can all agree is not a consensus when it wasn't done. But people forget, at that time, we had a no-fly zone in Iraq and every day, we were, our pilots were engaging, you know, the Iraqis every day, they were getting shot at. And so it's just those are things that I think, you know, it's, I call it the fog of war, you know, I have great respect for any president, Democrat or Republican on the National Security Council because you only know what you can, you know, you can learn from intelligence perspective and you have to make decisions based on the best until you have. - And how did you move from, you were on the national security side and then by time we were into the bladder part of the administration, here at the Treasury Department with Hank Paulson. And so how did you move from what you were doing on the national security side over to that role? - Look, I came back from, I took a year leave and went to Iraq. I was with General Frank's there. And you won't find a more anti-war person than me after that, okay? I'm a military officer. I'm a proud support of the military. You know, if my kids went to the military, I'd be honored that they would do so. But when you see something, and I wasn't in combat, okay? I didn't, it's not like I was getting shot at every day like my brother. But when you see a war up close and personal, you go, I can't believe human beings do this to each other, all right? And just the effects of it, or mental effects, the real death, the destruction. And so I came back after the Iraq war and I didn't want to work in politics anymore. I wanted out. I just wanted out, okay? Because it just, the fact that people do this to each other, it was almost an existential moment for me. And Connolly's a rice, actually, we're going back to the White House. And I wanted to work in for her, an Ashory council. And the day after the election, I went in to quit because I had enough. I don't want to stay with her. And she wanted to stay. So I went with her to stay, because she's someone I reverend look up to. And she's a big believer in diplomacy. You'll remember, she said the time for diplomacy is now. And, you know, I'm a huge believer in engagement. You know, someone that looks different than you, maybe has a different color skin than you, maybe speaks a different language than you. They have great values. They're smart. They matter. They're voice counts. And so I wouldn't be a part of that team. And then I had made a name for myself as someone that could like manage people and things and interactions. And obviously I learned a lot of that from Dan Bartlett and others. And then I get a call about the Chief Staff at Treasury. And at that point, I knew I was probably going to be employed when the administration was ended. And I wanted to get role management experience. I moved over to be Chief Staff for him. And when you first took that role, did you realize what a consequential period that was going to be from a financial perspective in the country? I actually didn't want the job. And again, I'm pretty direct. I took the job because it was 2006. Nothing was going to happen. It was going to be done in two years. After I got to the lead job, I'm going to talk to him all the time. So I figured, okay, I'll do this job and I'll go be an investment banker and make a bunch of money. I literally did it because, you know, and Hank was a guy who I fell in love with. I agreed with his approach. He was a serious stupeful, it's amazing financial leaders, a chance to learn from someone like that. But, you know, Treasury's typically a sleepy place. It's not really a deal shop. It's, you know, the adoption's dead. The mint reports to it. The Bureau of Engraving and Printing, you have the Financial Management Service, which every check that goes out of the government goes through. I mean, these are not the lamerous things. (laughs) I liked it, but, but, so no, I didn't know we were going to have a financial crisis because having built the 911, and I probably wouldn't have done it. But, but here we go again in 2007, Commercial Paper Market freezes up and no eight happens. And when did you first realize there was going to be a major economic problem? Do you remember the moment when it hit you? I do, I remember I was in a hotel. I was on vacation in California. I was in a hotel room outside San Francisco and Hank Paulson called me and said, the Commercial Paper Market's a freezing. And I mostly kind of understood what that meant. I was googling in, of course. (laughs) You know, I was a political freshman, not a finance group, but, but, and that's when I really began to know, and Hank, God bless him. He was, our country was in Paulson, a debt of gratitude for his leadership, and what he did because he saw that early, and, you know, he and Tim Geitner, and others really worked so hard on that, but it was because they saw it early. And, you know, I learned from Hank how these things happen fast, and you think they will. But, you know, privately being a part of those meetings for that next couple of years was, was incredible, obviously, and was proud to serve as part of that team, with such a great leadership team at Treasury. These many women that worked at Treasury, like Michelle Davis and Kevin Fromer, and, you know, and Phil Swagall and, you know, David McCormack and, you know, folks like that were just unbelievable. It's still a leavey on the terrace from hand side. I got a chance to work with these people who are just incredible leaders. People like Michelle Davis, who had to go out and explain this to the world, what was happening, and I dare say she did an incredible job. And so, you know, quite the time. - So, was Hank the first boss you had who came out of, you know,
the C-suite, the private sector versus, I know, Condi was an academic, Dick Armey came out of academia. Was he the first person you worked for with that kind of experience? I've never even thought about that, but you're right, he was. And now, you know, Condi had been on some corporate boards, but that's a great point. Never thought about that. So I'm curious, when you got there, obviously, very different remit than the one you ended up with near the end as the economy started to crater, etc. What was different about how Secretary Paulson ran Treasury versus some of the other folks that you worked for? Was there anything different about how he led or how he made decisions? Yeah, look, he, first off, he's a man of great integrity, and which is important. Number one, number two, he had, you have to understand, and I actually wrote, when I was a professor, I wrote some of this, in the first term of White houses, systemically, typically in our system, the White House is dominant. Okay, cabinet secretaries are typically not, don't have the power, the White House, everything is kind of run from the White House. In the second term, typically, everything devolves to cabinet department. That's just kind of a truism of American institutional politics. I studied a lot of this in grad school at my wonderful Johns Hopkins. I love Johns Hopkins. But, and so Hank was coming in at time when typically authority is devolved. He's also quite a figure. Okay, you know, Coral Roe, is someone I learned so much from. Coral Roe was just an amazing man. You know, historian, brilliant intellectual. I learned a lot from Coral, Josh Bolton, and others who were in Joe Kapp and others who were the leaders at the time there. But they always kept kind of a pretty strong control over it. You couldn't control Hank. Okay, he kind of hired who he wanted, he fired who he wanted, and he kind of did what he wanted to do there. And so the first thing he did is he brought much more of a, I learned so much from him, much more of a disillusioned approach, I think, to just day-to-day operations, which isn't for everybody in politics, right? Remember, in politics, your P&L is information. Okay, and it a place like Treasury, which is not a deal shop. That's why he had to bring all the people in in the financial crisis to help. You've got people there that have been in a long-term, the career people, amazing friends to this day. I still love that place. It's still my favorite place I've ever worked as a Jersey barman. But it's just different than Goldman Sachs where you kind of get what you want when you want it and do what you want. And so I thought Hank, at most people that do what he did, which coming from a place like Goldman Sachs, I can't do it, he did an incredible job. Those are a few things. So how did that form of leadership manifest itself when the crisis occurred, right? Because I know at the time you guys took a lot of flack over tarp in the time since, I think most people recognize that tarp probably saved us from a much larger economic calamity. What was it like in the room sort of trying to figure that out as it was happening? Well, first off tarp, I mean, I'm a communications genius, right? That's like the worst name ever tarp. You do what I'm saying. We have to, you know, we have the amputeil, you have tarp, I'm sorry. Let me back up. I think from Hank's perspective, I want to talk about Hank and the team. From Hank's perspective, he saw it early. He knew what to do. I think people in the ununderstand having him where he was and Tim Gagnar where he was. And so they're Bernanke. But Paulson and Gagnar were incredible. Okay. And so just to see it early, I think that that was super important. Number one, number two, to systemically understand, let's just take AIG. I remember walking in Hank Paulson's office and saying, "A.I.G is in trouble." And I said, I was really upset. Why are we going to let an insurance company make us like do something that we oppose policy wise? And he said, "Jim, you don't understand. AIU holding is made, you know, insurers, most major projects are on the country. A lot of construction projects and all kinds of other projects would just stop if we let it fail. You don't understand that the job." And so Hank had this unbelievable knowledge at a strategic level, but also at a front line level. Of what was happening in the economy. And he was a data fanatic. I learned from him. Words like very extremely, I don't know what that means. 1397, I know what that means. Numbers, right? And so he was able to do that. But then you had someone like Kevin and Frommer. You know, Kevin and Frommer ran legislative affairs for Treasury. Without him, that doesn't get approved by others. Kevin just knew what to do there. Okay. Bonnie Frank, you know, who I probably wouldn't agree with the most things. You know, Bonnie Frank was a big part of that at the time, as was Charlie Wrangler and others. And so not to mention it closely. And so Hank was smart. He put this team together. Michelle Davis, you know, Michelle Davis ran communications at Treasury. He was able to delete because at this point, Treasury was kind of in charge. I mean, President Bush had given a lot of authority to Hank and his president. Hank, every day working together to do this. But Hank really, and President, the president was such an incredible leader in this time. But, you know, I remind people, this is an important point for your listeners. The only reason we didn't have mass street panic in America was because of the personal computer and people say, how can you say that? My grandmother called me in the middle of all this. She's dead now, but she called me and said, are we going to have bank lines like we're doing as a kid? I said, that's ridiculous. Well, here's why when she was a kid, people lined up outside of banks. Okay. Because of the personal computer, everyone who's listening to this podcast right now, they all move money during the crisis. They did it on a computer. So you didn't have the scary visual. Does that make sense? We didn't have the scary visual. Because otherwise, you'd have had people in the streets. I remember that great line. There's a lot of people out. I think it's the Indie Mac, one of those banks to get their money. And this reporter asked us, guys, is why are you standing on line? He goes, I want my money. He said, well, how much do you have in it? Because I got like $5,000 in it. They said, well, you know, it's insured by the government. You don't have to worry. You can go home and he goes, well, it's okay with you. I'd like my money. It's just very human. And Hank had this great ability to understand the very human nature. But you had, people like Dave McCormick working internationally to make sure they all has didn't freak out. And you just had a lot of different people doing these things from a team perspective and watching Hank build that team of people of which I was lucky to be a small part of, who's just incredible. So it's hard to believe it's been almost 16 years. I want to say, within the next month or so, we'll hit 16 years since all of that transpired. It's amazing how time flies. One thing I think people forget is that Hank and President Bush, you major testament, frankly, to their leadership. We're able to circle the wagons, not just with Republicans, but with Democrats too. I mean, I remember Obama came off the campaign trail and McCain came off the campaign trail. Like, what was it from a leadership standpoint, communication standpoint that allowed them to break through? I mean, President Bush was not terribly popular in September of 2008, certainly not with Democrats. And yet here we are at this seminal moment and everyone's on the same team trying to figure it out together. And that seems very foreign to where we are today. A few key points. Hank, number one, thank God we had a lame duck president. Okay, because the president running for office for another time probably couldn't have done it. Okay, I mean, President Bush, Hank went to see President Bush. I was in the private meeting and he said, how hard is going to be politically in presence? He let me worry about the politics. He do a try for the country. As well as great moments. I remember President Bush. That's why I love and reviewer. I'm so many moments like that, but just great personal leadership from from so that's the first thing we had a lame duck president. Second is people didn't understand the problem. Okay, with all due respect to investment bankers, most of them don't understand derivatives. Okay, rocket scientists that go to MIT, it was much better to go to Goldman Sachs or to Credit Suisse or someplace like that and make structured products than it is to go be rocket scientists. It probably won't surprise you that pays more if you go to one of those places, right? And so you had a lot of people with these exotic products that frankly no one was good. Okay, second, a third thing you had the entire super structure of the American political ethos, going back probably for the lifetimes of everyone on these listen to this video, was buy a house. The American dream is own a house. And so the whole super structure of our economy was built around getting a house. It's always going to go up in value. Defined benefit plans were going away from retirement perspective. So you knew you'd buy a house. It would it would be very well. You make money. I give an example. Before I joined Hank, in 2005, I bought a condo in Alexandria, Virginia. Okay, I paid $494,000 for that condo. I also bought a Nissan pathfinder car this same week. I spent five times as much time buying the car as the house. Okay, I walk in there, they call a guy, they approved me for a loan, having never met me. I never filled out an application. I go to closing and I sign, I sign, no, because I was leaving to go to Russia that day with the secretary of the rights at the time. It's a work in state department. Okay, that condo, a couple years later, went from being worth $494,000 to worth about $194,000. Okay, and so, but that was happening all across America. That this is systemic thing happening. I think, you know, Bill Gross and Themco, they did an amazing job. They actually went out and walked the streets of Michigan and saw all this was happening. And that's why I think they went up making a bunch of money because they saw this was happening on the front lines. But people that had $65,000 or your jobs are getting million dollar mortgages. Okay, and Hank saw, Hank saw, you know, a lot of those things. The other thing is, I was on a lot of the calls when we briefed.
Um, presidential, uh, at that time he was running for president Obama and McCain. Okay. Um, I actually voted for president Obama because when we brief paling, Susan's not a serious person. And at that point, I was watching Hank Paulson, a leader, president, Bush, a leader. Um, and there was this big, great moment where one night, president, he's running for office. Obama calls the Treasury switchboard and gets on the phone with Hank Paulson. They talked for a couple hours, I think, about derivatives. Obama was really trying to understand this. Okay. And McCain was older and I thought, "Hell, he could die." And she just won't be president. And I don't agree with Obama's policies on pretty much anything. But I saw a serious person trying to solve a problem. And I was surrounded at Treasury by serious people trying to solve problems. And there were clowns in Congress on all sides of the aisle, but you had people really trying to actually solve solve problems at that point because everyone was scared to death. And so I saw T candidates in the last 30 days getting brief. There's this famous scene in the White House as you know, when they come back for the White House meeting and McCain blows up the meeting. Okay. Now, John McCain's an American hero and I love him and I adore this man and I own his book and will always revere him. But, you know, Palin was so scary that the idea of giving someone like that the keys to, frankly, anything was just not something that I could support. So those are just a few things. I'm trying to give you some sense of the mail strum that's in that period. The other thing is, is, you know, because of Tim Gaihtner, who again, I think will be a lot of gratitude to when he has picked this Treasury Secretary. I worked on the transition as part of a team that helped, obviously, all of our Treasury team get the seriousness of which, the President of President like Obama took that transition. It was important. Okay. And President Bush had wanted to be the best transition ever across all the agencies who were all instructed to work well with them. You know, but sometimes transitions, you know, you meet the transition team and then you meet another one, you meet like three or four before they actually do it. Because it threw on bodies at the problem. That wasn't the case here. Tim Gaihtner was going to be an amazing Treasury Secretary and his team of people were very serious. So that's some of the reasons it works. I'm sorry for the long answer, but I'm trying to give you some of this. No, it's it's super interesting. When you left the administration at the end of the Bush administration once the transition was complete, you went to my understanding, you went to Brunswick, you went to the private sector. What was different? What did you learn or what did you see when it came to communicating around a crisis, the kinds of complicated situations that folks were coming to you and getting advice on? How were people approaching that differently than the way your teams approached it when you were in government? Well, first off, I had to go through detox. I'd been thinking 9/11, I'm thinking of an answer crisis. When I interviewed with Alan Parker, I said, look, he or she in the movie say anything. I don't know if you've ever seen that movie. Sure. And then John Kisex says, I don't want to process anything, manage, manage, you know, that whole space. I didn't want to manage people. I didn't want to be in charge of anything. I didn't want to be a part of any crisis, which is funny. I went up at Brunswick. I can almost immediately wind up going to the UAE. Brunswick helped manage the Dubai got bailed out by Bidabi. I had to go help believe that. When is this going to end? But look, I want to live in California. I'm a marathon runner. I wanted to move to California, live in San Francisco. Hopefully, I found a wife, someone to marry me. I'm still single at my late 30s. I had not had good luck in dating. I wanted to go and be a runner in San Francisco and work at Brunswick and work on clients and kind of be left the hell alone for a while. And I had great guys there like Steve Lippen, who you probably know. Mike Buckley and so many people who I worked with there to learn how to do crisis work. And what's interesting, a corporate client with Collins, we have a crisis can you get on like, yeah, I'll be right over there. No, no, we can meet next Tuesday. The crisis in the government is like, it's happening now. I tell people, the government is so much faster than the corporate world. It's just so much faster than the government. Because it's, you know, if you're no matter who you are in the White House, Democratic Republican at nine o'clock, you're working on Libya at 10 o'clock, you're working on steel tariffs at 11 o'clock, you're working on tax cuts at 12. You don't get lunch. You're working on, a spring court nominee at one, you're working on abortion at two, you're working on, I mean, so it's just, it's, it's, it never stops, right? And so that that's what's different in the corporate, the corporate world that I saw. You see, you spend some time at Brunswick. And as I understand it, since you didn't want to ever manage anyone again, that's why you ended up going straight to one of America's best known companies, Pepsi, right? For you. Yeah, like I spent three years at Brunswick. I love that firm. Great people still have many friends there and they're just so kind. And Alan Parker is a great, I think great statesman and just a one, I'm talking a long time wonderful man. Yeah, by swore, I'd never work inside a big company. I didn't want to do it. I wound up working inside a big company, right? I'd gotten married. I now have a 10 year old and a 12 year old, at that time, they were born. And so we move, we get on a plane and we go to Connecticut. My wife is from iOS, she's a farm girl. She's never been to Connecticut. And so here we go. And we go up there to PepsiCo for Inja Nooy. What was it like working there? I mean, a very different set of challenges, obviously, universally known name. But what was that like running comms there? Yeah, so look, it's interesting, you know, I'm in Inja Nooy, this is an incredible person. Okay, and I didn't appreciate it. I appreciate her more day and day now. You've got chips and drinks. Okay, you've got Doritos, Cheetos, Fritos, okay, and then you've got drinks, right? Trust me, if you get run over, you want to get run over by a Frito Latre, not a Pepsi truck, because it's not as heavy, right? Because it's a lot more air in those chip bags. But in all seriousness, she's just this amazing leader. And here we go again, Nelson Peltz tried to break the company up. So now I'm fighting an activist investor. We wind up winning that, but I had a great team there, you know, people like Jamie Callfield, who's now CFO there. Keith Johnston, Inja Nooy was amazing. You know, just wonderful people all around the world, who Al Carrey, I mean, these are iconic names. I was able to learn from there and work for them. You know, I was a bit of a hero at home. You know, I don't do drugs. I've never smoked weed. It's just not my thing. I'm married to girl who's a weed smoker from Iowa and Doritos and Cheetos are part of the staple of that. Actually, it was awesome. No, it's just, you know, what are you going to do? Right? So, but, you know, so it became, I was very popular, but, you know, I just loved it. I mean, I learned so much from so many of those smart people there. I just learned so much about the corporate world, right? And that's a really iconic company. Of course, did you learn anything in particular about how you communicate effectively around an iconic brand like that? Where there's a hundred years of history, right? Everyone has an opinion on Pepsi. Everyone on the street knows what it is. How do you have to communicate differently around that versus like a, you know, an esoteric policy issue that matters to 13 people in DC, but may not be on the minds of normies on the street. Sasha, look, there's an important, which I think we need to study more as communications leaders. There's an important academic construct called interpretive location. That can be, you know, if I'm Christian and I'm talking to a Muslim or someone who's Jewish, we see the world differently. Not just Israel, we see the world differently. Okay. Age, gender, geography, all these are a part of interpretive location. Okay. Same thing inside companies with brands. So here's an example, right? Your average Pepsi person that worked at Pepsi was up at four in the morning at the office early, suit and tie, you know, a little left of center probably, okay, politically. Your Mountain Dew people were got to work about 11, you know, I don't know if they had a suit, you know, they, you know, would do things like have a skateboarder skate off a dam in India and get us attacked by the Indian government. Okay. You're, you know, you're free to lay in a free to lay's machine based in Texas, the US Army and free to lay. Okay, that free to lay is a huge thing. Think about if you're listening to this every store within a mile of your house, that's a lot of seven 11s and, you know, places has got Doritos and Cheetos and have you ever gone and then seen those things thrown ever they are always orderly. Okay, they are good at this. Okay, they're really, really good. But even there, Lipton T person is not going to hang out with the Doritos person. Okay. So, so I learned about different people, different things there in terms of working inside corporate brands and everyone's different. Okay. Very, very, very different. So you've got to pick a team that's diverse. That's where I came with my idea that, you know, you talk about DE and I, one of my problems with DE and I is I get tokenized as people. Okay. If you treat women or people of color or Latinos like corporate social responsibility, I think that's frankly racist is my view. I believe in DNI because I grew up in a town where black people were the majority Latinos were second and white people were third. I was, I was the minority. Okay. And I watched black growing up black people be a hundred percent of the population in some cases and zero percent of the power. Okay. And I thought that was wrong. Okay. I thought that was, I've always thought that was, I always thought that was incredibly wrong. Well, inside organizations,
you have to have diversity because by the time a problem gets to Sasha, you or Matt or me in my job now, or the head of any agency or a C sweet person, it's a hard problem no one can solve. You need to need young people, old people, gay people, straight people, black people, white people, you need everybody around the table. Okay, and I find when you focus on that, you know, different perspectives matter, I'm CEO of trail runner my company. My people that work in our Texas office are different than the people that work in nothing, California. And that's just okay. And I think we need to celebrate that. You know, celebrate that and love people who look in and talk and sound differently, but I learned that it Pepsi go. You know, they're one of the things that shocked. I think Pepsi goes, I asked as a white male Texas Christian who owns more guns and most gun stores. I asked to lead the ERG, LGBTQI ERG, because an ass wise said because you know, I believe in equality for everyone. And a gay person fighting for gay rights is not really interesting. A straight Texas Christian male fighting for gay rights is interesting. So I believe in unconventional messengers, if that makes sense. And I learned that there and I was so proud to lead that ERG and to do so much with, with, you know, that community. And so, but it's just, you know, I think we as leaders can learn from some like engineering. You've got to lead this whole kind of bar scene in Star Wars group of brands, 22 brands that were a billion more dollars each with a team of people that are all very diverse and type A. Gotcha. You bouncing around a little bit. One question for you in the time since you started trail runner. You work with a lot of major corporations and, you know, other groups that have complicated communications challenges. How have you seen artificial intelligence change the landscape or not at this point? You know, I think that. You know, there's a go on a great, this great proverb I heard do the day Turkish proverb that says, don't let clowns in your palace. If you let a clown in your palace. The clown doesn't become a king. The palace becomes a circus. I think that's very powerful in terms of management. And so. I think humans are always going to play a big role. It's a bit like when human when when cloning first came out and they said we're going to clone him as I said, no, I think for a lot of reasons, we're still going to probably have kids the old fashioned way. You get a subtle joke there. And so, but so I think what we've got to train people to do is to lead groups of people. And so you're always going to have judgment. So things I think AI is important. I think it's crucial. I'm a huge believer in technology. I think the communications business is slipping into basically low margin business and high margin business. Okay. When you've got a major communications crisis, AI ain't going to fix that for you. And you got to do basic corporate stuff, AI can do that all day long. And it's not. It's not hard. And I think I think what it's going to do. I love this in our industry because communications and what like what Apple car does what we do a trial runner when he confirmed does that used to be a cost center. It's now become the spinal cord of the PNL. And so within that spinal cord of the PNL, where the other mega trend of finance PR comms litigation all kind of crashing together that nucleus and spinal cord is where Apple car frankly is the best world. But that's where you want to be working. You're making cars while the rest of world makes buggy. And so how we train young comms people is amazing. I tell people this is important for your listeners. I'm 54 years old. I was expected to run something in my 40s. Okay. You could sort of clown around in your smoke weed party and do whatever I didn't do that part of you have to wait. You could do that in your 20s and then figure it out in your 30s. Not today young people are expected to run something their early 30s. And so that that's just a systemic change in the from an academic perspective in the economy. And so that internship program is now a lot more important because it gets you early hiring decisions that are very important and it gets them up that value chain faster. So the kinds of people you're looking for are going to have to be trained. I think you need to need enough at a out of use it, but it's not going to replace things. I think you'll be able to say, Hey, Apple car. Who are the 100 most important influencers and influence X product or company and get that in two seconds. Okay. But then how you use that. I think it's still going to be human human driven. Understood. Last question we like to ask everybody a lightning round just about their own personal experience dealing with different communications tactics what they think works what they don't think works. I'm going to run through some of some of those things you want to just tell us what you think about these things whether whether you think they're effective whether you think they're worth doing when you're trying to get a message through. When it comes to DC and breaking through on Capitol Hill, you know hosting events with publishers or others. Do you think that that's a meaningful way that the company is able to break through. No, you're eight or weeks. Members of Congress is either constituents at home more than ever. Because, you know, members of Congress, Tindale by anecdote. I was not 10 people that again, I go back to my training in the financial crisis. No one knew what was inside those derivatives. Okay. Those financial products. So many many times I'd go out and tell CNN. Hey, this is this is a neat guy and repeat what I said on there because they didn't know either. Okay. So, so, somebody we didn't know. Telling someone who certainly didn't know about informing people who needed to know and what great. So I just don't think that that works. I think the best communications is outside the belt. So when it comes outside the beltway, like do you think that, you know, when those grassroots intercepts happen at indistrict events. Do you think that those make a difference break through to members. Only if so. This is either the greatest thing that worst thing ever happened in the world because everyone has a mobile phone now. Everybody who's listening to this and all of you. We all have our own ecosystems. It's 100% possible now only to surround yourself with people that agree with you. Okay. By way, that's bad. So the most powerful people are the connectors of the ecosystems. Okay. If I took five of your listeners there who are listening to this and we sat down and really looked at our ecosystems. We might be completely different, look different, come to parts of the country. If we could find crossovers those ecosystems and bring them together, you're unstoppable. It's frankly what apple car does so well. And so events will work in local areas if they're bringing ecosystems together. If you're in Texas and you got a bunch of pro gun, gun rats, people like me talking a bunch of other pro gun rats people this wasted motion. Okay, we call that preaching to the choir. But if you can sit down with someone you don't know. And has someone say, yeah, you know, I don't agree on this, but I kind of agree on that. Then those are the most powerful people. So if you call it letter campaigns make any difference. Yeah, because they sent their symbols. Okay, meaning we had election in our local town here. The guy ran from mayor call me and said, I got an anonymous letter in my mailbox. Oh my god, what do I do? What do you do? Somebody defend your mailbox. What if they send it to everybody? They didn't send it to everybody. You know, no one's going to go spend thousands of dollars for the West Lake mayor's election. It's not that important. And so, so it's just I think they can be symbols. And so, you know, the, I am just on a complete and total campaign to get rid of junk mail. They're completely wasting money and killing trees. But it's just, you know, sorry. But it's just, I think, so I, I, I, I think right now. Sasha, I call it the barking dog theory for my childhood. When one dog barks at three in the morning, they all start barking in the neighborhood. Okay. So if someone gets a letter and they post it on social, then yeah, that works. If that makes sense, if it's bringing ecosystems together. Got it. You think that that TV ads in a member's district make a difference? Depends. I tell people run them during football games. Yeah. But like, you know, Doug Flutey, Info Marshalls, I doubt they sell much at three in the morning, although the person that's up at three in the morning, probably is going to use Doug Flutey in Frank Thomas's. Life enhancement, whatever the hell that stuff is, they sell right? And so, you know, and so I just, I, I, I think what's much more important is being in their social platforms. Again, I go back to interpretive location. When Apple cart does so well, I think is you understand interpretive location. Get to people where they're having the discussion. I get all the times. Someone will call me and say, hey, we need a, we need a website. Why do you need a website? Well, because we need one. Why people are going to hold hands in American come to your website and go, thank God I discovered you. Okay. I'd much rather be on the social media platforms of the hundred influencers that decide the conversation. Then, then that I would rather. Okay. I don't even watch TV. Okay. Like I love the sopranos. I love the wire. I watch baby reindeer, which I wish I could unsee. That was crazy. I watch series and I watch, you know, the greatest sport ever created in the history of the world football. And so, you know, you got to be, you got to be careful there, right? So I just think go live on the mobile phone where people are. Well, Jim, listen, really appreciate your time. Thank you for answering all of our questions and sharing all of this insight with us. Well, to have you on again.
But I just want to say something, I just met my career working with some of the most amazing people in the world like you all, but people have been kind to me good to me explain things to me. You know, taught me how to write when I was a great writer taught me how to write press releases taught me how to do influence of work. These are wonderful people and. I just want to say to thank you to them, but just see these are people who like Hank Paulson and Kandi Rice and President Bush and Michelle Davis and Kevin from her and you know carry nine all these people I learned from. None of that good. And you know, especially when you have kids I've actually fought Terry. I have a 12 year old daughter trust me it's hard and so you know so. You know it is what is I'm grateful to you and congratulations on what you all built it's amazing and I think you got her on the cutting edge. We appreciate it. Thanks Jim. If you enjoyed this episode and are interested in listening to more conversations with decision makers, you can subscribe to the decision makers podcast on Spotify Apple podcasts or www.applecart.co/resources. Until next time I'm Matt Kalman's and this was decision makers. [BLANK_AUDIO]
Podcast Summary
Key Points:
Jim Wilkinson’s career began accidentally, from a small Texas town and a dream of owning a funeral home, to an internship in Congress and working for Dick Armey.
He learned that in government, the person with a proposal wins, and that logistics and management are more important than tactics.
During the 2000 Florida recount, he witnessed intense political maneuvering, including using costumes to influence media coverage.
At the White House under President Bush, he was mentored by figures like Karen Hughes (who taught him to give unvarnished opinions), Dan Bartlett, and Condoleezza Rice (who emphasized intellectual curiosity).
His experience in the Iraq War was transformative, making him anti-war and leading him to leave politics temporarily, later serving under Condoleezza Rice and Hank Paulson at Treasury.
He took the Treasury role expecting a quiet tenure but was thrust into the 2008 financial crisis when the commercial paper market froze.
He credits Hank Paulson’s early recognition of the crisis and leadership as critical to the response.
Summary:
Jim Wilkinson, executive chairman of Trailrunner International, recounts his unplanned journey from a small Texas town to the highest levels of government and business. Growing up in Tenocht, Texas, he initially aspired to be a funeral director but accidentally entered politics after an internship with Congressman Charlie Wilson and later working for Dick Armey. He highlights that in government, “the person with a proposal wins every time” and that logistics and management outweigh tactics.
During the 2000 Florida recount, he participated in chaotic, media-savvy tactics like renting costumes to influence coverage. At the White House, mentors like Karen Hughes taught him to always give unvarnished opinions, while Condoleezza Rice instilled intellectual curiosity. His time in Iraq during the war profoundly affected him, making him anti-war and prompting a desire to leave politics.
He eventually joined the Treasury Department under Hank Paulson, expecting a quiet role, but was quickly caught in the 2008 financial crisis when the commercial paper market froze. Wilkinson emphasizes Paulson’s early foresight and leadership as vital. His career, shaped by luck and mentorship, underscores the importance of management, directness, and learning from crises across public and private sectors.
FAQs
He grew up in Texas and got an internship with Congressman Charlie Wilson, then worked for Dick Armey after applying for jobs by writing letters from a library.
He learned that the person with a proposal wins every time, and that amateurs talk tactics while professionals talk logistics.
He helped at the NRCC and traveled to Florida, where he witnessed the chaotic recount process, including using costumes to influence media coverage.
He helped with confirmation teams during the Bush transition, and after being offered a deputy director of communications job at a lower salary, he accepted to join the White House.
Karen Hughes taught him to give unvarnished opinions, Dan Bartlett emphasized management, and Condoleezza Rice inspired intellectual curiosity.
He learned to always give his unvarnished opinion and call things as they are.
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