JORDAN McLEOD: Hey listeners. This is Jordan McLeod, executive producer of Masters of Scale. What you’re about to hear is a conversation we had in 2020 with Stephen Colbert, host of the CBS Late Show. We spoke with Stephen as part of our episode with Charles Best, founder of the education nonprofit Donors Choose. We call this type of interview a “cameo” appearance — short, but impactful. And in Stephen’s case, totally hilarious.

Previously, this uncut interview has only been available to Masters of Scale members. But we’ve decided to share it now with all of our listeners.

Why? First, because it’s the holidays, and a perfect time to give to the charity organizations you care about. Donors Choose supports teachers and their classroom projects across the United States. It’s a great place to do some end-of-year giving.

And secondly, we’ve been releasing our complete, uncut interviews with anchor guests for a while. But starting with Stephen, we’re now releasing our favorite uncut cameo interviews in the app. 

They can be found in the Masters of Scale Courses app, which you can download free in the App Store and the Google Play Store. 

We’ve had some unbelievable conversations with these cameo guests, like LeVar Burton, Chris Paul, Code for America’s Jen Pahlka, will.i.am of the Black-Eyed Peas, and many, many more. Inside the app you can listen free to hundreds of great episodes, and clip your favorite moments into shareable videos. And when you become a Masters of Scale Member, you’ll also unlock a collection of highly-curated courses designed to cultivate the entrepreneurial mindset. We have a 7-day free trial so you can get a taste before you commit. Download the Masters of Scale Course app to get started. 

Now, onto the show.

STEPHEN COLBERT: This is very professional looking.

It looks like I’ve just been given the nuclear football.

Okay. So here we go.

Microphone recorder, mic stand base. Okay.

McLEOD: You just screw that doodad in and then put the mic in it.

COLBERT: That goes in there.

McLEOD: That’s right.

COLBERT: Gotcha. There you go. That’s it? That’s the whole damn thing?

McLEOD: That’s it. That’s the whole damn thing. 

COLBERT: And are we rolling? Yeah. Six, seven, eight.

McLEOD: It’s recording. 

COLBERT: Look at that. Put me in coach. 

HOFFMAN: That was Stephen Colbert, comedian, writer, and host of the Late Show with Stephen Colbert. And what you’re about to hear is our complete, original interview so you can experience it in full. 

I’m Reid Hoffman, co-founder of LinkedIn, partner at Greylock, and your host. In each episode of the classic Masters of Scale, I prove a theory about scaling a company – through the story of our guest. 

We talked to Stephen as part of our episode on the “Power of small goals,” featuring Charles Best of DonorsChoose. Now, you won’t hear my voice in this conversation. Instead, you’ll hear two of our executive producers: Jordan McLeod, who just helped Stephen set up our recording kit, and June Cohen, who conducts the interview. You might also hear some laughter from the rest of our team.  

Stephen joined the DonorsChoose Board of Directors in 2009, and he’s helped raise millions of dollars for the organization. But the story you’re about to hear is how Stephen first got connected with DonorsChoose. And it starts with his satirical run for President of the United States, as host of The Colbert Report on Comedy Central.

Many of you told us that you’d love to hear the full interview. And now — you can. 

[THEME MUSIC]

JUNE COHEN: All right, Stephen, we love laughing with you, but I should ask you some questions, so we can stick roughly to our time we have with you.

COLBERT: All right.

Why Stephen Colbert satirically ran for President of the United States in 2007

COHEN: All right. So Stephen, it’s 2007. You decided to run for president. Take us back to that moment and just tell us why you decided to run.

COLBERT: I believe the first reason I decided to run was because I showed up in a poll. And in the poll I was beating Joe Biden. I believe that it was a poll specifically coming up in South Carolina and PPP, which often will just throw in a cultural figure just for schnicks, for sort of attention. And I think they’re a little sort of a left-leaning polling organization as well. They said, “How about Stephen Colbert, South Carolina?” And I got like 2.5% in the poll, and Joe Biden got like 1% in the poll. And we had already played several games on the show at that point. So this 2007, we’ve been on the air not quite two years because we started in October of 2005. We’d already had a bridge named after me in Hungary, or tried to. Ben and Jerry’s launched an ice cream with my name on it. Then I got in a competition with Willie Nelson with his ice cream talking smack, and Richard Holbrooke had to come in and negotiate a peace treaty. I got into a fight with Sean Penn at one point about him talking with George Bush. We had to have a game show that was moderated by the Poet Laureate of the United States, because it was me complaining about his poetry and it was …

So we had these different games and went, “Well, of course my character immediately sees that if he’s on the political map, I mean, listen, he didn’t choose this path. Destiny chose him and a polling company. And therefore, who am I to deny the American people, 2.5% of whom think I should be President of the United States. Well, let’s respond to the call of a troubled nation and give them what they want.”

So, now the network was not thrilled. They’re like, “No, look, you can’t run for president.” I’m like, “Well, we’re running for president. We’re 100% in. Stop me. Stop me.” I mean, literally there were several times over the years, and I’m not a screamer. I mean, you can go ask people like five times in 20 years of doing this, have I really lost my temper. But the Viacom lawyer got an earful from me when they said, “Well, look. Ultimately, we’re not going to allow you to run for president.” And I’m like, “Oh, so I’m canceled? Is that what you’re saying? Because I’m running for president. Because you don’t know anything about comedians if you think that you’re going to stop me from doing something because you don’t think I should.” But I said at a high volume, and there might’ve been a few salty words in there.

So we do it. We decided to run. But for me, I was very interested in corporate money in politics. So what I wanted to do was I wanted to run for president and to be fully sponsored by a corporation. And we’d already done an inclusive sponsorship in the show, like “Tonight segment is brought to you by Triscuits” or whatever. And then we would just talk trash about the product. But they would still get their product on the air. It was all great. So I said, “Let me find a corporation who will sponsor my presidential campaign. Because as far as I can tell, it’s not actually illegal for them to do so.” People think it’s illegal, but is it really illegal?

And so I set out. We went to Doritos. We want her to be the Nacho Cheese Doritos, Stephen Colbert campaign for president. And it turned out there were some legal problems there. And it became the Nacho Cheese Dorito coverage of the Stephen Colbert run for president with your host, Stephen Colbert. So they were sponsoring my coverage of my own campaign for president. And so that’s how we did. That’s how we got around those concerns. So we decided to do it, and I go down there, and I hold a rally, and I’m shaking hands. I’m doing all the things you do. I’ve got my little campaign team, and the car running around. I’m pressing the flesh with local leaders. And people want to give me money. And the one thing that our lawyers are saying, “Don’t take more than $5,000 from anyone. Because then you’re in a federal election, and then you will get in trouble. You. You personally.” I’m like, “Well, I don’t want that. I don’t mind Viacom getting in trouble, but I’m important.”

And so Craig Newmark comes on the show, Craigslist. He comes on the show. I don’t know if he was a board member of DonorsChoose at the time, but he was definitely very interested in it. And he said he’d like to make a donation to the campaign. We said, “No, no, no, you can’t give me any money.” And he goes, “Oh no, no, not to you. I’d like to give it to an organization called DonorsChoose. They’re just starting in South Carolina.” Because they weren’t in every state, and they were soon to start in South Carolina. “They’re just starting in South Carolina. So I thought perhaps people could make donations to DonorsChoose in your name. And that would be a way of them showing their support without running afoul of federal guidelines.” I’m like, “That’s pretty great.”

So he made a pretty big donation on air. And then, I don’t know, we raised like a quarter of a million dollars or something for schools in South Carolina in the next month. And it was terribly exciting. And then I got to know much more about it. My friend, Jonathan Alter turned out to be on the board. I had Charles Best on. I learned more about the organization. I thought it was fantastic. I loved getting the letters back. So that spring, I mean I had to drop out. I had to drop out eventually because the Democrats would not let me on the ballot. Someday someone will read the letter that I wrote the Democrats asking them for me to stay on the ballot. I couldn’t sleep the night before they were voting about whether I could be on the ballot.

Stephen Colbert’s letter to the Democratic Party

COHEN: Will you send that to us?

COLBERT: No. No, I won’t send you that. It’s too personal. There’s nothing funny about it. It’s actually very heartfelt because I was up all night going, “Well, everyone is raised in America with the idea that any child could grow up and be President of the United States, but not you, Stephen Colbert. The Democrats won’t let you on the ballot.” And I know it was just a joke, but it still felt bad. And so the Democrats kicked me off. I mean, the other candidates basically got together and muscled the Democrats of South Carolina to not allow me to be on the ballot.

But that spring, when it came down to just Mrs. Clinton and Mr. Obama, and Pennsylvania was going to settle it. That was going to be the big thing. Pennsylvania is going to settle it. I don’t know if you remember that. It didn’t of course, but it’s all going to come to a big battle in Pennsylvania. We took the show to Philadelphia, and we had people donate to DonorsChoose either in the name of Hillary Clinton, Barack Obama, or John McCain. And all the letters that the children sent to us because you get letters from the children whose projects you fund. We said, “Don’t send us letters. Send us drawings of the candidate for whom the donation was made.”

And our set in Philadelphia was just covered with all of these children’s drawings that were just absolutely beautiful. And Mrs. Obama, when she was on before she was the First Lady, she was on one of those shows, and I gave her a framed copy of one of those and just one of the most beautiful drawings of the President ever seen by just an eight year old girl from somewhere in Pennsylvania. So that’s the first thing we did, was that campaign year. First running and then Pennsylvania. And by the way, both in Pennsylvania, Obama’s people smoked everybody else.

COHEN: Totally. I do remember.

COLBERT: Was that too long of an answer? Sorry.

[Ad break]

HOFFMAN: We’re back with our special bonus interview with Stephen Colbert. If you’re enjoying the episode, why not share it? Just tap the share button in your podcast app. And to hear more complete interviews like this one, become a Masters of Scale member at mastersofscale.com/membership. 

All right, back to the interview. 

COLBERT: Can I give you one more data point about running for president, of the Doritos run for president? We also found out from our lawyers that you can’t eat any free Doritos products given to you on air because that would constitute a corporate donation to the candidate. So I had a bag of Doritos that I bought and a bag of Doritos that had been given to me by the company. And I said, “I can eat these, but I can’t eat these.” And I put them below the desk, and then I shuffled back and forth and brought them back up and started eating one of the bags, daring anyone to sue me because there’s no way to prove which one I was doing.

It was such a delightful … One of the great joys of that show was that we didn’t do anything fake. I was fake, but everything I did had to be real. I had to really run for President. I had to really testify before Congress. We had to really hold a rally. We had to really file for the federal election commission to grant me a super PAC. Everything had to be real because we wanted to take the things that are assumed to be okay when you don’t think about them because they’re below the counter and put them on top of the counter and say, “Does it still look okay when you see it happening?”

COHEN: Which is why you win Peabodies.

COLBERT: I guess so.

COHEN: Because it’s brilliant.

COLBERT: I guess so.

How DonorsChoose engaged in Stephen Colbert’s satirical game

COHEN: All right. So Stephen, let me ask you one or two more questions just to kind of follow up on a couple of things you said. So DonorsChoose comes to you. They come to, I’ve forgotten that it was in the form of Craig Newmark, but they come to you, and they proceed as Charles recollected, who is of course a great fan. He recollects that you had a challenge that they were filling, that you wanted people to support your candidacy, but you didn’t want or couldn’t take actual money from actual fans for a parody campaign. And so his perception is they were helping to solve a problem for you.

COLBERT: Yes.

COHEN: Is that why you said yes?

COLBERT: Yes. I mean, well, it wasn’t so much that they were helping me solve a problem, it was that they were engaging in this satirical benign game. They became players in the scene. Every show, people would ask me how we wrote the show or how I conceived of the character. I said, “Oh, it’s all a scene. I’m not a talk show host, I’m an actor.” Now I’m a talk show host, but then, “I’m an actor.” And what I was doing was a scene with the audience, and the audience was the other player, and they wanted to improvise with me.

And so the audience donating to my campaign was accepting my initiation and then yes-and-ing it. And then I had to deal with their initiation, which was actual cash. And then Charles and DonorsChoose come in to say, “Hey, here’s our acceptance of your audience’s initiation. We’re going to add this to the scene, which is a very sort of positive, benevolent way for them to engage in your game that is good for the people of South Carolina and is, in a strange way, kind of the thing that a politician might do, which is engage with an educational organization.”

So what I loved about them was their understanding of how they could engage in it in a positive way that had real impact in the world, yet lived in the fantasy world of the character as a positive action that would also fit with his ego. And so I just loved … their playfulness was actually an excellent tool to do something good in their mission.

COHEN: I love that, that it was actually a beautiful collaborative, active improv.

COLBERT: Yes. Yeah, exactly.

Why Stephen Colbert got involved with DonorsChoose

COHEN: One last question, Stephen, because I know we’re a bit over. So that one first engagement with a DonorsChoose led to a much deeper engagement. In fact, you’re now on the board. So what about that first specific engagement pulled you in for the next one and the next one?

COLBERT: Well, I was actually, I was very moved by the letters I got from the children and from the teachers. And I saw the immediate and quantifiable difference it made for these people. I mean the whole idea of DonorsChoose puts you and the people who you are helping directly in contact with each other. And I found that very powerful. And I think everybody on a certain level wants to do what they can or use their position in some way to help people who need any variety of things. And those letters from the children, the letters from the teachers made it very real for me. And I didn’t want that to end. In fact, the next year when we took the show to Iraq, Charles said, “Hey, we’re actually expanding to military bases. What if we gave money for just very specific military bases?”

And so that was his understanding that we were doing something special, which would call for perhaps additional kinds of actions by the audience, ways the audience wanted to participate in this adventure we were going on. And we raised half a million dollars for military base projects. And then the year after that when we were doing the rally on The Mall, we raised another half a million dollars for DonorsChoose to get … People on Reddit saw that we played games with DonorsChoose. And someone from Reddit came to me and said, “Hey, if we raised a half million dollars for DonorsChoose, will you do an Ask Me Anything on Reddit before you go to the rally?” And I literally did the Ask Me Anything on the train down to go to the rally because right before it started, they made it to half a million dollars.

So what do you want more? A way to play your own game that does something good in the world and makes people happy and feel included in the art that you’re creating? It had everything. And a lot of that came from the leadership of the organization that was willing to take a risk on us because satire has always got a little bit of a knife in its hand, but they understood where we were poking it, and they were okay.

COHEN: That’s so awesome, Stephen. I want to respect your time. You’ve given us an incredible story and such delight. Any last thing you want to share that you’d want people to know about DonorsChoose or any last thoughts that you want to add?

COLBERT: It’s a great experience to give to it. Just do it, big or small. You don’t have to pay for the whole project. Some parts of the project. They all have the little status bars of how close they are to completing it. In your community, go look at the school you went to as a child. Go give to somebody in that classroom that was your homeroom. Give back to the child that you were. Go give yourself a hug as a child by giving to this child now, especially if you were somebody as a child who needed that hug. You can do it. Go help that child.

COHEN: Love. 

COLBERT: Thank you.

COHEN: Stephen Colbert, you give so much to so many with your comedy. Thank you so much.

COLBERT: Thank you. What do I do with this? I just put it back in the thing and throw it out the window?

McLEOD: Yeah, you can just turn it off the same way you turned it back on. Put it in the thing, and yeah, a pigeon will come by and pick it up.

COLBERT: Thanks. Bye.

HOFFMAN: I’m Reid Hoffman, thank you for listening.