Scott Shrum President & COO of Hennessey Digital and Jeopardy! Champion

Interview on the Jason Hennessey Podcast 10-27-2021 - Episode 2
Scott Shrum

Hennessey Digital President & CEO Scott Shrum Shares his Wit and Knowledge

Today we’re giving you a little behind the scenes insight. The audio footage you’re about to hear was supposed to be a rehearsal day with Scott and Jason in the studio, where they were going to just try out the gear, test out the audio equipment, maybe break a couple things, and just play around. But once they listened back to everything, they were in complete shock and awe. The sounds and rich textures they were hearing went straight through the nervous system and right into the soul.
It became increasingly clear that we potentially have a voiceover legend on staff, right here at Hennessey Digital, just waiting to be heard. So, it was decided. Scott Shrum would return to the studio, to finish the epic episode that he started. We just had to hear those vocals again, on these high performing mics.
The world, they deserve to know. They deserve to know how Scott went to space camp in Huntsville, Alabama, how he’s lived and visited various parts of the country, that he’s an alumni of MIT and Northwestern, about his incredible Jeopardy! championship, and that he’s a great father and husband.
So ladies and gentlemen, back by popular demand, Scott Shrum in the flesh, with us at Hennessey Studios. Please hit the play button at the top of the page and follow along below. Thank you for tuning in to today’s remarkable episode.

In this Episode

[02:17] Jason opens the show by informing us that Scott Shrum walked into the glass in the studio. Scott explains it’s an on-brand occurrence, and we learn a little bit about his background being President and COO of Hennessey Digital.

[03:56] Scott recalls that it’s been exactly 2 years since they first leased the space and studio they’re recording in. He and Jason think back on how they were able to transform the space into Hennessey Studios during the pandemic.

[06:57] Jason wants to know more about Scott’s personal life since they’ve been talking mostly business so far. Scott shares that he’s happily married with two kids and that they relocated from Chicago to Southern California.

[08:26] Jason invites Scott to look back on his younger days. Scott details his childhood growing up in New Jersey as an only child, spending time with his grandparents in Pennsylvania and Virginia, and his parents’ interesting and distinguished careers.

[12:03] Jason is curious about what Scott’s dreams and aspirations were as a kid. Scott remembers wanting to be an astronaut, going to space camp, and losing the opportunity to join the Air Force Academy due to a severe foot injury in high school gym class.

[15:00] Jason asks Scott when he realized he was smart. Scott recounts the days he was going to a private Catholic school and how they kept moving him to the advanced groups. In high school, he put in the time, effort, and accountability that held himself to keep on learning.

[18:22] Jason wonders if Scott was in the race to be valedictorian of his high school senior class. Scott reveals why he chose to come in 3rd in the race and how he had already been accepted to MIT before graduating.

[21:13] Scott describes his campus tour experiences and reasons for submitting two college applications. He also reminisces about the day his acceptance letter arrived, and when his mother told him the exciting news via payphone during gym class.

[25:50] Jason brings up the cost and asks if Scott’s parents had any doubts about being able to pay for tuition. Scott explains how teachers encouraged his family to sue the school due to his foot injury. The settlement was his scholarship to pay for MIT.

[29:49] Jason invites Scott to reflect on the events that led him to where he is now. Scott assures Jason that he inevitably would have ended up in the same spot. He reasons that every job he’s taken on has felt right for him.

[31:52] Scott answers a few more personal questions about the most influential person in his life, his most embarrassing childhood memory, whether he’d turn the volume up or down on a Taylor Swift song, and the latest concert he’s been to.

[35:35] Jason highlights Scott’s appearance on Jeopardy! and is interested to know about the experience, from the audition, to the callback, all the way to being cast. Scott divulges more about the interview and preparation process, and when exactly he started trying to get on the show.

[39:28] Scott shares the book that former Jeopardy! champion, James Holzhauer, recommended to him to help prepare for the show, among other subjects he studied before going on air.

[41:05] Jason and Scott talk about the answer that won “Final Jeopardy!” for Scott and how the question was referencing the 1983 Pritzker Prize and its recipient. Scott previously recommended an architecture tour in Chicago to Jason that mentioned the architect’s name.

[42:35] Scott expresses the surreal experience that was being on stage with Alex Trebek, and how comfortable he was after watching about 4,000 episodes of Jeopardy! He also tells us about the fun conversation he had with Trebek during a commercial break.

[44:30] Jason and Scott embark on a game of “Strip Jeopardy!” If Scott guesses the question incorrectly, he has to take an article of clothing off. Categories range from “Double Talk,” “Weird Town Names,” and “Epic Rap Battles of History Speakers.”

[53:42] After putting a few clothes back on, Scott joins Jason for a round of “Never Have I Ever.” They take turns reading 10 questions from a deck of cards and first to answer 7 questions truthfully wins. It comes down to the wire as we discover if they’ve ever taken Adderall, eaten out of the garbage, lost a fist fight, “Facebook stalked” someone, and other exposing have-evers.

[01:06:51] To close the show and as a thank you, Jason gives Scott a signed copy of Law Firm SEO, a book that manifested from Scott’s utilization of the COO Alliance’s “Big Idea Calculator” and relaying the idea to Jason that he needs to write a book of his own.


Jason Hennessey: Scott Shrum, although it wasn’t too smart when you walked into the glass here in our studio room. Tell me a little bit about how that happened.
Scott Shrum: Yeah, that was very on brand for me. I was just putting some of my stuff down. I said, “Oh, I’ve got to run back out a second.” Did a 180, “Bang,” right into the plate glass.

Your nose, I saw your lip mark on there…

Yeah, yeah.

…and your nosemark on there.

Oh, I left, yeah. Definitely left a mark on the glass. I don’t know. Later on, I’ve got to go to the bathroom, see if it left a mark on me. But I feel okay right now.

For those that don’t know, that are listening, we’re going to go back, back to childhood days. But first, tell me a little bit about what your world looks like now, professionally, personally.

Yeah. You know, but I’m President and COO at Hennessey Digital. I’ve been on this ride with you for a little over 2 years now. In that time, gosh. When I started, what did we have? 50-some people? Now we’ve got about 130 people. We lease this space. We’ve got so much going on, and it’s crazy.

I remember when I first got onboard, and saw everything that we were doing. First of all, I was impressed. Second, I was terrified, and said, “Holy crap, we need a CFO. I think I know just the person,” and brought Michele Patrick on, to join us in the adventure.

Since then, I’ve brought together a couple of my other old band mates from my last job. Including Blin, and Alex Trenchard-Smith. You’ve brought on some people from your past adventures, including Matt.


Brian, and Rob, and-

Yeah, Brian, yeah.

Yeah, mm-hmm.

Yeah, it’s been an amazing ride so far. Even what we’re doing right now, a couple years ago, true fact, tomorrow it’ll be 2 years to the day since I first visited this space, with Josh Bernstein, who showed us this space.

It was July 1st of 2019. If you told me that almost exactly 2 years later, we’d be sitting here, doing this right now, I wouldn’t even be able to envision it.

It’s been 2 years since you stepped foot into this space, right?


That was a pretty interesting time, because we didn’t know that there was going to be this pandemic. We needed a space. This was the first space. It seemed like it was perfect, but it wasn’t available. It seemed like everything else that we looked at felt more like an insurance company, on the 18th floor.

So we landed here, in the Television Academy campus. Here we are, 2 years later, and we’re making this happen, so thank you. You are the reason why we’re here.

Oh, thanks. I remember, we fell in love with this space. They said, “Great, you should know that somebody just put an offer on it.” We were like, “Ugh.” That was July, August of 2019. Then I remember, we spent the next several months looking. Every few weeks we’d go out with Josh, and look at spaces. Like you said, we’d look at other ones. We were like, “I don’t know, this is okay. I don’t know, I don’t love it.”

The one probably that we got closest with, was basically the next building over, 5250 Lankershim. Remember, the space that used to be the Institute for the Arts?


They were just about to tear that down. There was a lot that we liked about that space. I think we like this better, but we liked it. We were getting close. Then suddenly, we got the call, “Hey, 5200 Lankershim, that fell through. Are you guys still interested?” We were like, “Oh my god!”

The funny story about that is, for those that are listening, when we went over to that, it was an old educational- what was the name of it?

Art Institute?

The Art Institute, right? They were like, “What do you envision this to look like?” I’m like, “I don’t really know.” I’m like, “Scott, come here. Let’s peek in. Let’s see what’s going on,” right? Then there was a studio, right?


It was exactly what we needed. But they were like, “Well, if you want it to look like this, you’ve got to let us know tomorrow. Because this thing’s getting knocked down and demoed.”

Yeah, there was rubble everywhere. It was in the center of the building, so there was no natural light. There was no power. We were lighting our way with our phones. We were like, “Oh my god, a recording studio. This is amazing.” They were like, “Yeah, this is getting torn out tomorrow.”

It had everything that we needed in there.

Yeah. We did like that space, but this was even better, and then this opened up. That was late 2019, yeah.

Then 2 years later, here we are. For the past year, obviously we haven’t been able to get in here. But I think it’s been on schedule anyway.

It could have gone a lot worse, yeah. We signed that lease literally weeks, several weeks before the world shut down. At that moment I was terrified. I was like, “Oh my god. What do we do?” But it’s worked out.

We signed that lease literally weeks, several weeks before the world shut down.

Tell me a little bit about- That’s the professional side. Let’s hear a little bit more about the personal side.

Let’s see. Well, I’ll start with the present. Happily married, with two kids. My wife, Anita, is an actuary. She was working out of our home way before it was cool. Way before Hennessey Digital even existed. She’s been with that company since the late ’90s. How’s that for longevity, right?

Whoa, talk about loyalty.

Yeah. We relocated from Chicago, to Southern California in 2008, when I took a job. Her company didn’t want to lose her, so they were like, “Well, we’ll set you up with a home office or whatever.” So, she got set up with a home office, at our home in Westlake Village. That’s where she still works, out of our home office.

When we moved in 2008, we had a 1-year-old daughter named Diana. She’s now 14. She starts high school in a matter of weeks, less than two months. We have an 11-year-old named Elanor, who starts sixth grade in the Fall.



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So it’s a big transitionary year, huh?

Yeah, it’s a big change of a year. But they’re both so brilliant and funny. They’re good people. More than anything, I can just tell, they’re going to grow up to be good people.

They don’t know- If you ask them what they want to do when they grow up, they don’t know yet. That’s just fine. But they’re so bright, and they’re just such good, conscientious people, both of them.

Well that’s a testament to obviously the parents, the grandparents, right?


Your childhood, your wife’s childhood. How you guys were brought up. I guess that doesn’t surprise me. I want to go back to “Young Scott.” When you were growing up. You grew up in New Jersey?

Grew up in New Jersey, yeah.


Just me and my mom and my dad. I was an only child.

Okay. Did you have grandparents that lived close by?

My dad’s parents lived in Western Pennsylvania, where my dad grew up. My dad grew up, he was born in a town called Roscoe, Pennsylvania. Then the family a little later moved, really the next town over, called California, Pennsylvania. It’s right along the Monongahela River. About an hour south of Pittsburgh. My grandparents still lived there.

My mom’s father passed away before I was born. But my mom’s mom, and her new, nowadays you would call him a “partner.” That word, they were a long term couple. But they weren’t married.

My grandmother, and I called him Uncle Gene, lived in Northern Virginia. I would see them at least a couple times a year. But in New Jersey, it was me, my mom, my dad, and then I had some aunts and uncles and cousins scattered around.

What did your mom and dad do for a living?

My dad worked in a steel mill. He was a plant manager, at a company that made steel tubing. Then when I was about 11, he moved to another job, just another company that did something similar. They made copper rod, in Port Newark. He was the plant manager for this company that made copper rod, called AmRod, for my whole life.

He came in very much as an entry level maintenance job, and then worked his way up to literally running the plant. He didn’t go to college-

Didn’t go to college, okay.

He didn’t go to college. He joined the army when he was 17, right out of high school, in Western Pennsylvania. Ended up serving in Korea. My dad was brilliant, but never went to college. [My dad’s] job in the army, in Korea, was doing maintenance on nuclear bombs.

[My dad’s] job in the army, in Korea, was doing maintenance on nuclear bombs.


Yeah, nuclear weapons, yeah.

Talk about a scary, responsible job, huh?

Yeah. Self taught, and then they trained him and everything. But yeah, that’s what he did. When he got out of the army, he ended up working different maintenance jobs. Ended up getting into manufacturing. That’s what he did.

My mom, when I was young, she was a stay-at-home mom. Then when I was a little older, and I was in school and I was self-sufficient, she worked in a bank for a while, as a bank teller. She was there for a few years. Then the job that she had, by the time I was a teenager, and she was there for, I think 15 years, she was a secretary at a prison, for the New Jersey Department of Corrections. That’s what she did.

Where we lived in New Jersey was kind of rural. A town called Annandale. Annandale and the town adjacent to it, Clinton, New Jersey, they’re known for- there’s a minimum security men’s prison, and a maximum security women’s prison.

My mom worked in the easier one, the minimum security men’s prison. It was so minimum security, there weren’t even fences.

So, your dad’s dealing with nuclear bombs, while your mom is dealing with prisoners.

Well yeah, that was in the army, yeah.

Okay, but still.

But this was minimum security. They didn’t even have fences.

Okay, I see.

An escape would be, a guy just walked away, and got in a car and drove off. So yeah, that was her job until she retired.

So growing up as an only child, what did you think you wanted to do, what was your dream? When people asked you, “What do you want to do when you grow up?”

When I was young, probably like a lot of kids, I was way into space. I was like, “I’m going to be an astronaut.” I was hellbent on being an astronaut. Let’s see, this would have been summer after eighth grade, I even went to space camp, in Huntsville, Alabama. I was all about space camp.

When I got there, at space camp, I didn’t know it, but the first thing you do is, you took a written test. They didn’t tell you that ahead of time. I took a written test. I got the highest score, so I got to be the commander of the mission, of the shuttle mission, which was really cool. I was hellbent on being an astronaut.

Then in high school, I was primarily math, science, math, science. My plan was I was going to go to the Air Force Academy. But when I was a sophomore in high school, I broke my foot really bad. This accident happened at high school. This was sophomore year. We were in gym class one day. If you remember, they had, the volleyball nets seemed to be held up by poles.

By cement blocks, right? Almost?

They just had these huge, I think it was a big metal, steel base, that was on two wheels. You could tilt the pole, and roll the whole thing around. The teacher asked me and these two other guys to go move the poles around.

This kid, Brian Whitmer, tilts the pole back. He didn’t do anything wrong. He tilts the pole back to move it, but the pole and the base were not attached to each other. There was a pin that was missing, and the base came off of the pole, crushed my foot.

Oh my. Left foot? Right foot?

My right foot.

Your right foot.

I had to go to the emergency room. I had to-

You can still feel that pain from that day, right?

Yeah. Well, I had to immediately, 1 second later I had to rip off my sneaker, because my foot just expanded to 5 times its size.

Of course, yeah.

Long story short, I had to have two surgeries. I was on crutches, and in a cast for months. I had to do months of physical rehabilitation. That injury is what kept me out of the Air Force Academy. I got recommended by my senator, which is kind of the main step.

Of course, yeah.

Senator Bill Bradley of New Jersey, I got recommended by his office. That’s the main thing. But I got a call saying, “I have some bad news.” As soon as the call came in, I knew what they were going to say. It was like, “Yeah, that injury, your foot. You’re disqualified. We can’t accept you,” so I knew. But I wasn’t devastated, because I figured that was going to happen.

Because there is so much physical activity that takes place at the academy.

Right, yeah. Even if my long term at the Air Force Academy, maybe I would go into the Air Force and end up being an Intelligence Analyst. Still, to make it through the academy, they were like, “You’re deemed physically unfit because of your foot.”

That was it, so I didn’t get in. I was like, “All right, Plan B.”

But before we get into the “Plan B,” let’s take a step back.

As a kid, you wanted to be an astronaut. You obviously had a gift in school. When did you pick up on, “I might be smart. I might have a gift here in school”?

I’ll tell you a funny story. When I was 8 years old, my family, we actually moved to another part of New Jersey. But up until I was 8, up until the middle of third grade, we lived in a town called Plainfield, which wasn’t the greatest town. My parents sent me to Catholic school, just because it was better than the public school.



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I was going to Catholic school. Every year, there were families that would donate a lot of money to the Catholic school, so their kids would always get put into the advanced group.

We didn’t have a lot of money. We weren’t poor, but we didn’t donate excess money to the school, so they’d always put me in the middle group, not the advanced group.

Not the advanced group, okay.

Two weeks into the school year, the teacher would say, “Why aren’t you in the advanced group? I don’t understand, what the heck happened with you?” Then they would move me.

After this happened two or three times, I realized, “Huh, there’s something about this system that is trying to keep me down.” But the teacher thankfully is recognizing, “Hey, you’re advanced. What’s going on here? We’ve got to move you ahead.” I’d end up getting the best grades in the class.

Even by the time I was in third grade, I realized, they keep pointing me out as, “You shouldn’t be here. You’re advanced.” That just became a running theme.

I realized, they keep pointing me out as, ‘You shouldn’t be here. You’re advanced.’

Everybody’s different, right? But for me, I would have to study, index cards, memorization. Even writing things on my hand. School didn’t come naturally for me. Did you have to study real hard?

I studied hard.

You did?

I did. I did study. I think that’s something that, you know how when you learn about great athletes? It’s like, “LeBron James isn’t just great because he’s gifted. The guy also puts in more work than anybody.”

Especially thinking of high school, I would say elementary school and middle school weren’t particularly hard for me. But by the time I got to high school, just being honest, I think I wanted it more than other kids. I put in the time. I really did. My parents were- it wasn’t the pressure, you hear about “tiger moms” or something, who would pressure their kids.

Of course, yeah.

It was me. The pressure came entirely from me. In fact, my parents would even, they didn’t tell me this until I was an adult. But my dad was worried, “He should be out with girls more,” and stuff.

No, because it’s probably safe to say that 80% of the valedictorians that you hear about, the parents put all the pressure on them, right? For you to have that self accountability at such a young age.

I entirely put that pressure on myself. I honestly think I wanted it more than most kids. I was a nerd. I studied, I was not getting the girls. I was getting the grades. Whoop-de-do.

I was not getting the girls. I was getting the grades.

There’s a lot of those that would have preferred to be in your shoes now in life, right?


It’s your senior year.


It’s probably a race to be the valedictorian. Did you know that there was somebody that was going to have-

Have I told you this story?

No, I haven’t heard this story.

It’s not the race that you’re picturing. This is true.

My freshman year, I learned that, “Oh, at graduation when you’re at the end of senior year, the valedictorian and the salutatorian, number two, give a speech.” They each give a speech. “I ain’t doing that.”

So I called my shot. I was like, “I want to come in third.”

You told them that? Seriously?

I mean, I just said to my friends. It’s not like I told the teacher or the administrator.

I see.

But it was like, “I’m not giving a speech, oh my god.” Because that terrified me. I’m a lot more comfortable public speaking now. But 16-, 17-year-old Scott didn’t want to hear about giving a speech at graduation.

The last week of senior year, it took a while for them to tabulate the grades, and this and that. They told the top five-ish of us, “Start thinking about what speech you might give. You’re not going to know until 48 hours before graduation. You might have to give a speech.”

I’m like, “Oh no, oh my god.” I was terrified. I didn’t even lift a finger towards writing a speech, because I was in denial. I didn’t want to do it.

Then I think it ended up being the day before graduation, they came out. They were like, “All right, here’s the rankings. Scott,” they sit me down, “you won’t be giving a speech. You came in third. But when I say, “You’re-” I’m like, “Yeah! Oh my god, yeah!” I was already in college. I’d already gotten into MIT, so I didn’t give a shit.

Yeah, it didn’t matter, right?

I came in third, which is what 14-year-old Scott predicted.

See? Go figure.

I didn’t have to give a speech.

The fear of public speaking. They say that most people would rather be in the casket than give the eulogy at a funeral, right?


It is. My wife is deathly afraid of speaking in front of people.

That group, we’d all gotten into college. I don’t know, I’m trying to remember if any of us really cared what our rank was. We kind of didn’t care at that point. I didn’t.

Yeah, I think we had a class of 900 maybe.

Oh my god.

It’s small, right? I was 792 in that class.

Oh, that’s a big class. Mine was tiny. My high school class was only 290.

Oh, is that right? Okay. Yeah.

Yeah, so we were tiny.

I was definitely- But then again, I guess if I would have tried a little bit harder. I certainly didn’t have the natural ability. I had to work real hard in school.

You didn’t necessarily have the aptitude for the stuff that school wanted you to do.

No, that’s right.

Yeah, but in the real world, you’ve got more of the aptitude that matters.

That’s right, I think so. Yeah.


So you applied to how many schools?

I only- I applied to two: MIT and Caltech.

What made you decide those two?

At the time, I was all math and engineering. Because I was an only child, I was very close to my parents, but there was no way in hell I was going to go to college close enough that my parents could come visit every weekend, so I needed to at least be a few hours away. MIT was a 5-, 6-hour drive. Caltech was obviously on the other side of the country, in Pasadena.

My parents indulged me. I said, “I want to go look at Caltech,” so we flew out the spring break of, I think my junior year of high school. Yeah, it was spring of ’92, we flew out here. We looked at Caltech, and we looked at Harvey Mudd College, which is out in Pomona, the Claremont McKenna colleges.

Caltech was awesome. It was cool. Then I went and visited MIT. Caltech’s campus is beautiful, by the way. MIT’s campus is not beautiful. But across the river from MIT was Boston, which is the greatest college town. It’s a real city, but it’s also, there’s countless colleges in the area.

We walked around MIT for an hour, and I was like, “Yeah, this’ll do. I like this. Let’s go across the river. I want to go look at Boston.” We went, and just did everything in Boston. Ate seafood, and went to a baseball game, blah blah blah, and that was it.

When I say I only applied to two colleges, it’s less daring than it sounds because I applied early to MIT, and got in early. By December, I got into MIT, of my senior year. That took all the pressure off.

Then I applied to Caltech, because I was still interested, and I got into Caltech, but I had already made up my mind, I was going to go to MIT.

Now, when you were applying to MIT, for those that are listening, probably know that MIT, it’s the top 1% of the top 1%. It’s extremely hard to get into that school. Was there any doubt that you might not get into that school?

Oh yeah. I didn’t know if I’d get in. I was the first in my family to go to college. I didn’t know.

I was the first in my family to go to college.

When we went and visited MIT, we didn’t even know how to properly do a college visit. We didn’t contact the admissions office. We just showed up. It was spring break at Caltech, and we just walked into the admissions office. My parents said, “All right, here’s our son. He wants to go to Caltech.”

To their credit, the admissions people at Caltech were the nicest people. The associate dean of admissions sat down with me for a half hour, and got to know me. They could have just chased us out and said, “Get the hell out of here.” I had no idea what I was doing.

The day that you- I’m sure you remember this day very clearly. You got something in the mail, and it was either going to be a good message, or a bad message, right? Walk me through that. Did Mom get the envelope? Did Dad? How did that happen?

Our mail would typically come in the early afternoon. I remember, it was the first week of December of my senior year. I had sports practice after school. The week when I knew the letter would be coming, every day after school, I drove home from school just to check the mail and see, and there’d be no letter. I had to hustle back to school for practice. Did that 3 or 4 days in a row, no letter.

Then one day, either I’d stopped bothering, or I just didn’t have time to run back home. Of course, that’s the day the letter comes. So right before practice starts, I remember, I was at a payphone at North Hunterdon High School. Dropped a dime in, called home.
“Hey Mom, it’s-” She was like, “It’s here. There’s a letter from MIT.” I’m like, “What is it? Is it big?” She’s like, “It’s little.” I’m like, “Oh, shit.” She said, “Do you want me to open it?” I said, “Open it.”

Wow, so Mom opened it?

Mom opened it. I’m on a payphone at school. She starts reading the first five words, and it’s like, “Oh my god, I got in. I got in.”


Then I just went back to- I walked into practice. This kid, Jeremy Gasper, standing next to me. He’s like, “Hey, are you okay?” Because I just was…in a daze. He was like, “What? Hey, what’s going on?” I said, “I just got into college.” Then everybody started celebrating.


But I just was, I didn’t- It was just hitting me, and I was all freaked out.

Such a big moment. I guess at that point, obviously Mom’s proud, right? Then Dad gets the phone call probably.

That would have been the time, he was driving home from work at the time.

He’s driving home from work, right.

He probably got home within an hour, and found out. Yeah.

He must have been- Obviously, the parents must have been very proud, but then the expenses come. Like, “Whoa, how are we going to afford this?”, right?

Yeah. Well, that’s where my volleyball scholarship came in.

That’s when the volleyball scholarship came in.

I’ll talk about that. I don’t mind.


Part of the reason for wanting to go to the Air Force Academy is, the military academies are free. Tuition paid, you don’t pay a dime. That was part of the appeal.

But my parents, to their credit, said, “Get into the best college you can get into. We’ll figure it out. We will figure out how to pay for it. You’re not going to not go to a college like MIT because we can’t afford it.”

When I broke my foot, I was in the hospital, having surgery on my foot, and there was a teacher, one of my high school teachers happened to be there because his wife, I think, was having some procedure done.

He came and visited me. That was the first person who- it was a teacher at school. He was like, “You should sue. We’re all in the faculty lounge. We’re all talking about it. Unbelievable what happened. You should sue.”

I was like, “Oh, no. I don’t want to sue. I don’t want to get in trouble.” It was intimidating. My parents were like, “Oh, we don’t, I don’t know.”

We kept talking about it, and everybody, people at the school were urging me to sue, so we ended up going- We just opened, how is this for SEO, right? There’s no internet yet. We just opened a phone book, and-

Found the first lawyer with a magnet in the back, right?

We just found a listing, “This guy sounds good. John Coyle, in Phillipsburg, New Jersey.”

There it is.

We actually interviewed three different law firms. They were the local big firm. We weren’t getting the main guy. “You’re not getting John Foy. You’re getting one of his minions,” right?

Of course not, yeah. Mm-hmm.

We didn’t like that. Then we went to another one, and the guy seemed a little too bookish. We wanted somebody who was an aggressive bulldog, you know what I’m saying?


The second guy seemed a little more like a law school professor. The third guy was like, “Yeah, F the school. We’re going to sue them. We’re going to sue the manufacturer.”

Sue everybody.

“Take down their insurance company.” I’m like, “You’re hired.” That was, the interview happened in early 1991. The case didn’t settle until summer of 1993, when I was already out of high school. But then we settled- but we knew the settlement was probably coming, because the negotiations were happening for probably the better part of a year.

We had to go to court. I had to sit on the stand, and talk to the judge-

Depositions, mm-hmm.

Because I was a minor, the judge had to interview me, and make sure that I understood what was happening and everything.

I was up there for one minute, and he was like, “Okay. You’re not a little kid. Do you have any questions?” I was like, “No.” He was like, “All right, you’re good. Get out of here,” so that was it. That lawsuit is how, well– it paid for MIT.

That lawsuit is how, well– it paid for MIT.

That paid for MIT.

Yeah, it paid for grad school too. But yeah, so that was my- what our mutual friend, Tim, calls my “volleyball scholarship.” It paid for when I got an MBA later, too.

That’s interesting. Your high school paid for your college.

Yeah, my high school’s insurance company, yeah.

But I guess at the same time, you ended up hurt, right? You didn’t go to the college that you wanted to go to, with the Air Force Academy. But I guess everything was meant to be.

Oh yeah, absolutely. My experience in college, I wouldn’t trade it for the world. Culturally, it fit me perfectly.

I met my wife at MIT. She was a year behind me. She was a 17-year-old freshman, and I met her-



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So she was a really smart one then, huh? Okay.

She pursued me, for the record.

As did my wife. We could talk about that too.

A couple of hot commodities-


But yeah, it all, it really did work out for a reason, and it was for the best.

Do you think about that a lot? Do you think about the slightest little decisions that happen in your life? You getting injured, not getting into the Air Force Academy. Ending up at MIT, meeting your wife, having children. Do you think about the littlest things that really impact your life like that?

I do. I also- a lot of the life that we live feels kind of inevitable. Part of me feels like I almost would have just ended up in the same spot, doing this right now, because that’s what I’m supposed to be doing.

I know, it starts to get very weird and philosophical. I think about it, but not to the extent, I don’t think of a lot of, “Oh no,” what ifs. Or, “Am I on the right path?”

I’ll just give you another example: working with you at Hennessey Digital. Since college I’ve had five main jobs. Five real jobs. They’ve been in five different industries. I’ve had, really, five different jobs, in five different industries.

I remember, when I started talking to you about this role, and I was talking to some friends, and some mentor types. They would say, “Oh, but that’s not what you’ve done. That’s very different.” I was like, “Yeah, that’s right. Yeah, but that’s what I want to do.”

The people who know me well know, “Yeah, Scott’s just going to-”

Do what he does.

“Do what he does,” yeah. Any of my past jobs, or my past adventures, they’ve all been me. They’ve all felt very consistent with me. I’ve never felt like, “Oh, I’m doing something weird, or out of the norm.” It feels inevitable, or it feels right.

Any of my past jobs, or my past adventures, they’ve all been me.

Yeah, I feel the same way. I feel as though your life is going to happen, and you just act it out, right?


Decisions that you make will lead to things. Then at the end of the day, you’ll be able to picture it all together, like a puzzle, right?


All right, I just want to end here, with a couple of quick questions. Who do you say had the most influence on your life? If you had to pick one person?

If I had to pick one person? Oh man. I would say my dad, because like I was describing earlier, somebody not college educated. The way he- I didn’t realize this when I was a kid, but especially in retrospect as an adult, he moved his way up, just by learning and working hard, and being so valuable that they needed him, you know what I mean? They couldn’t function without him. Eventually to the point where he was running the whole operation, without a formal education.

That- Sometimes, when I get a little intimidated by something, and absolutely- I’m in my mid-40s. I absolutely still get intimidated by new challenges. I’m like, “Oh, I’ve never done this. I don’t know-” I think about, “Well, my dad just taught himself everything, and I’m half him, so I can do that.” So probably my father, yeah.

I absolutely still get intimidated by new challenges.

Dad, okay. Most embarrassing childhood memory?

Oh man. Well, it wasn’t running into plate glass. Let me think, most embarrassing childhood memory?

I remember one time, I was on the bus for school, going to school. The bus, I think, probably, there was a detour on the road, so the bus took a different turn than normal. I was probably 6 or 7 years old at the time. When that bus made a turn, I thought, “Oh my god, we’re all being kidnapped,” and I just started hysterically crying, and asking for my mom and dad.

When I got to the school, the teachers had to surround me. They were like, “He’s having an episode. What’s wrong with him?” But I just had been so convinced myself that we were being kidnapped, because the bus took a slightly different path to school.

Some kids I think always remembered that about me, so that was probably my most embarrassing moment.

Yeah, if that’s pegged to Scott, right? When you think of Scott, he was thinking he was getting kidnapped, right?

Yeah, the bus took a left, and Scott flipped out.

Okay, so you’re in your car by yourself, driving home from our beautiful studio here in Hollywood, California. Taylor Swift comes on. Do you flip the station, or do you turn it up and jam out?

Flip the station.

Flip the station.

Yeah, yeah.


I’m more- I listen to Sirius XM. I listen to Lithium. I’m an old fuddy-duddy now. I’ve got my Spotify playlist I listen to. I don’t know anything about new music. I’m listening to my ’80s music, and my ’90s music, some ’70s.

Yeah, it’s always fun. You’re driving in a car, you see a grown adult jamming out, and you’re always wondering, “What the heck are they jamming out to?”

I do that. I sing in the car. It’s not Taylor Swift.

It’s not Taylor Swift, right.

Nothing against her.

The last question that I have, since we’re on music. What was the last concert that you went to?

Oh man. Last year, right before the world shut down, there’s a live music venue near my house called The Canyon Club. It was the lead singer of Fountains of Wayne, who’s my favorite band.

Yeah, “Stacy’s Mom,” right?

Yeah, that’s their known song. But they have a lot of songs. The lead singer of Everclear, and two other bands. It was those four guys, doing a storytelling thing. Where they play some songs, tell stories, and the audience can ask them questions. They play each other’s songs, and just jam. It’s cool. That was the last show that I went to.

Something fascinating about Scott that some of you may not know, is that Scott is a major Jeopardy! champ. He went all the way to the end, and actually won the game. Not only did he win the game, he also did it while Alex Trebek was still hosting, right?

Yeah. Well first of all, you’re too kind. “Major Jeopardy! champ.” A one time Jeopardy champ. But yeah, I’m very proud of that.

That’s right, yeah. We taped that in late August of 2020. About 2 months later, Alex Trebek stopped recording, I think at the end of October of 2020. Actually, his last day of taping was the day that my second episode aired nationally. That was it, and he was dead 10, 11 days later.

Oh my.


Tell me, what was that whole experience like? From auditioning, to getting the call, to going down. Tell me how that went down.

I started, I could go way back. I started trying to get on Jeopardy! back in the early ’90s, when I was in high school. Back then, you would send in postcards to try to get on. Never heard a peep from them. Never got a response.

I started trying to get on Jeopardy! back in the early ’90s, when I was in high school.

Then sometime in the 2000s, maybe the early 2010s, they transitioned to an online test. That you could do this 50-question quiz, that they would do that a couple times a year. I would faithfully do it every time. You don’t know how you did. You don’t know how you did relative to anybody else. I would never hear anything back. Always would do this.

Then in early 2020, it was early in the pandemic. After doing one of those tests, I got an email, inviting me to the next step. I was like, “Oh my god, oh my god.” Of course, it being the pandemic, it was a Zoom audition.

The next step was a one-on-one interview with this woman. If you watch Jeopardy!, they have these two people who are the Clue Crew. They’re the people who will stand in front of the pyramids in Egypt, and introduce a clue. Sarah from the Clue Crew did a 10-minute interview with me.

You were probably starstruck just by her being there, right?

Yeah, immediately. I just started laughing. I was like, “I know who you are.” I did the next 50-question quiz, which was on Zoom. She wasn’t delivering it, but so we did that. She interviewed me some more, and it ended.

Again, you don’t know how you did. You’re like, “I don’t know. I think that went fine, I don’t know.” Then I forgot all about it. A couple months later, I get an email inviting me to the next step, which is another audition on Zoom.

That one was in a group. There were maybe 15 of us. They would take us three at a time, and we would play a mini version of Jeopardy! Just for a couple minutes. They just wanted to see, “Do you get the game?” It didn’t matter how many you got right or wrong.

Did that, it seemed fine. They do a mini interview to make sure you’re not a bore. Again, seemed to go fine. I forgot all about it.

Another couple months passed, and then in early August of 2020, my phone rang. It was an LA number. I was like, “I’ll pick that up,” and it was Jeopardy! saying, “You’re going to be on Jeopardy! in 2 weeks.”

How cool is that?

They just give you the date, “Be there or be square.”

Who was the first person you told?

I ran downstairs, and just announced it.

To everybody who was around.

Yeah, yeah. So my wife, Anita, and our two kids, they all just heard it. I just blurted it out, and yeah.

That’s a show that you’ve been watching since you were a kid, right?

Yeah. I thought about it at the time, and I estimated that I’ve seen over 4,000 episodes, going back to the ’80s. Yeah.

Do they ever repeat questions on that show?

They don’t repeat questions exactly, but there is a finite amount of stuff, you know what I mean? You might get some Shakespeare questions that, if you go back 7 years, it’s like, “They basically asked that same question.”

In just a different way.


How do you even- knowing that you watch the show, so that’s partially training, but how do you even train or practice for a show like that?

From when I got the call, to when I was going to be on air, was only 2 weeks. I didn’t have a lot of time, but I did two things. One, there’s a guy named James Holzhauer, who’s one of the all-time winningest Jeopardy! guys.

He’s a “major Jeopardy!-”

Yeah, he’s a “major Jeopardy! champion.” I’m a “small-time Jeopardy! champion.” He recommended a book that he read before he went on Jeopar dy!. It’s called The Secrets of the Jeopardy! Buzzer. It’s just a whole book devoted to the Jeopardy! buzzer. It’s really more of a pamphlet.

But so, I immediately bought that book, and read it. You learn the optimal- This guy tested the optimal way to hold the buzzer. I used that way of doing it.

The other thing I did in that short amount of time, is I just tried to bone up on some categories that I knew are weaknesses for me. Just to try to- I knew I wasn’t going to get from poor to expert. But I would just try to get from poor to not embarrass myself.

Some basic Shakespeare things. European and British royalty. A good one to just try to commit to memory is world capitals, and bodies of water. You just learn the longest rivers in Asia, and what are the capitals in South America? Things like that. I just spent those 2 weeks trying to bone up on that stuff, and that was it.

But really, it’s just all the crap you’ve accumulated in your head over, in my case, the first 44 years of your life, before I went on air.

You told me a story about how, just going to Chicago and taking the architecture tour, was-

Yeah. My wife and I, we lived in Chicago for 6 years. The game that I won, the “Final Jeopardy!,” the category was “Awards and Honorees.” The “Final Jeopardy!” clue was, “He used his 1983 Pritzker Prize money to fund a scholarship for students from China, to study their profession.”

Then the music starts playing, and I’m like, “Pritzker Prize, Pritzker Prize. Crap, what the hell is the Pritzker Prize?” I was winning going into “Final Jeopardy!,” but I was like, “I have to get this right if I want to win.”

Then suddenly, it just popped into my head. “Pritzker Prize is for architecture.” We’d lived in Chicago for a long time. I recommended that Chicago boat tour to you.

You did.

The architecture tour. I think it was somewhere in there that that’s why I knew what the Pritzker Prize was. Then the Pritzker Prize popped into my head, and immediately I was like, “Okay. Modern architect. Chinese male. It’s got to be I.M. Pei. That’s the only architect I know who fits that description,” so I wrote down, “Who is I.M. Pei?”, and I got it right.

You went big, right?

Yeah, I had $17,800 going into “Final Jeopardy!” My opponent, the returning champ, had $12,000. The other person had bombed out before “Final Jeopardy!,” she had negative. I knew I had to beat $24,000, if he was going to double his money. So, I bet $6,300 and I ended up winning $24,100.

That’s amazing. When you first get there, and it’s surreal. You’re on set, and in walks Alex Trebek. Were you nervous? Or confident? How were you feeling?

You know, it’s so funny. Of that experience that day, playing the two games that I played, I remember maybe 20% of it.

Sure, you’re just in the moment.

I don’t even remember it, yeah. The game happened so fast. The clues come. If you happen to ring in and get it right, you just immediately pick another clue. You’re just flying. You’re not even aware of the scores. You’re barely aware of what’s going on.

Trebek himself was awesome. You had a little bit of interaction with him, but he basically- The music would start playing, and you didn’t see him. Then he would come out and say a few words, and the game starts, and that’s it. You’re off to the races.

But I felt like, after 4,000 episodes, I got the game and I knew what to do. I felt very comfortable.

That’s awesome, and everybody that knows you saw it back home. You were a star for a couple days.

I have a funny Trebek story. They do those little interviews after the first commercial break. He interviewed me about improvisational comedy.

By the way, you don’t know what he’s going to interview you on. You give them five topics. You have to come up with five interesting things. He can ask any one of them. You don’t know what he’s going to ask.

He asked me about improv comedy, and asked, “Don’t you have a lot of jokes up your sleeve? Don’t you kind of cheat?” I said, “No. Honestly, it’s truly improvised.” Then we went on, we finished the round. Then you go to a commercial break.

Alex just started talking to me again about improv. He’s like, “Really? You don’t have canned jokes? I would have canned jokes. That’s amazing.” I was like, “Oh my god, Alex Trebek is honestly interested in my story.”

I was like, ‘Oh my god, Alex Trebek is honestly interested in my story.’

Jiving with you, that’s cool.

He kept talking to me. It was so cool. He was terrific.

Based on that, if you haven’t guessed already, Scott, we’re going to play a version of Jeopardy!.


This is where you’re going to be able to show off your vast trivia skills and knowledge.

Bring it on.

And of course, showcase that silky sweet voice of yours. You in?

I’m totally in. Trust me, like I said, I’ve been training all my life for this. So it’s the one thing I’m good at.

All right. But also, you may have guessed that we’re going to play our Jeopardy! version, but it’s got a little extra spice.


Today at Hennessey Studios, for an audio audience only, no cameras please, you’re going to engage in a yet sophisticated version of “Strip Jeopardy!”


Instead of getting points for correct answers, you’ll have to remove an article of clothing for every incorrect answer.


I hope you brought some layers here today.

Is it too arrogant to say I like my chances?

Not at all. But for real, jokes aside, let’s put the witty, the clever, the uber smart Scott Shrum to the test to see how many trivia questions he can get right, of these very, oh so tricky, 30 or so that I have here in my hand.

30? Whoa. I should have worn layers and layers, and mittens, and earmuffs, and everything.

All right, so these are the categories, Scott.

You’re not going to do the Jeopardy! music? We probably don’t have the rights for that.

Yeah, I don’t know. Maybe we could do something.


All right, so here’s the categories that you get to choose from.


“Double Talk.” “Play On Words.” “Who’s the Boss?” “Weird Town Names.” “Epic Rap Battles of History Speakers.”

Let’s start with “Who’s the Boss.”

All right. You have 100, 200, 300, 400, and 500.

Let’s start with 100.

This Facebook boss once had, “I’m CEO, bitch,” on his business card.

Who is Mark Zuckerberg? Let’s take the same category for 200.

There’s debate as to whether this English boss’ recent 50-mile trip counts as losing his space virginity.

Who is Richard Branson? 300.

This quantum chemist is sometimes described as the de facto leader of Europe.

Who is Angela Merkel?

I’m impressed.

Let’s do 400.

This rapper served as boss of Def Jam Recordings from 2004 to 2007.

Ooh, who is P Diddy?

I would have guessed that too.

No, I got it wrong. Who is it?

It’s Jay-Z.


Hold on a second, you’ve got to take off an article of clothing.

All right, so we’ll do that again.

It’s not so easy here, man.

Okay. Oh. Take off my hoodie?

There you go.

Okay. I dress like Mark Zuckerberg, but now the hoodie’s coming off.

This Enron founder was still the boss when it collapsed in 2001.

Who is Jeff Skilling? That’s not it?

It says, “Who is Lay?”

All right, what are my remaining categories?

You’ve got “Double Talk.” “Play On Words.” “Epic Rap Battles of History Speakers.” “Weird Town Names.”

Let’s do “Double Talk.”

A cartoon version of a Roman emperor uses this slogan to sell pepperoni pies.

What is, “Pizza pizza.”

Nice job.

Let’s do “Double Talk” for 200.

Also known as the common dolphin fish, its name comes from the Hawaiian for very strong.

What is mahi-mahi?

Dance frequently done by a line of dancers to the music of Orpheus in the Underworld.

What is the Can Can?

He’s currently serving a life sentence for his 1968 assassination of a presidential candidate.

Who is Sirhan Sirhan?

Pretty good, man. You’ve still got a lot of clothing on here.

Yeah, all right. 500.

Washington state‘s second largest prison is at the ominous address of 1313 North 13th in this small city.

What is Walla Walla?

That’s frigging impressive.

See, that’s an example of one that, I don’t know the answer, but when you’re watching that show, Jeopardy!, you just triangulate it. “Oh, I know there’s a town in Washington called Walla Walla. I’m going to go with that.” I didn’t know it.

Oh, I see.

That was a guess.

You seemed pretty confident though.

You’ve got to sell it.

You’ve got to sell it.

All right, so we’ve got “Epic Rap Battles of History Speakers.” “Weird Town Names.”

Well, I’m really feeling myself after Walla Walla, so let’s go with “Weird Town Names.”

Let’s hope I can pronounce some of this stuff. Zzyzx, the alphabetically last town name in the United States of America, is located in this state. It’s spelled Z-Z-Y-Z-X.

What is California?

Yeah, I’ve seen that.

Yeah, we see that-

On the drive from Vegas.

Route, the 15? Going to Vegas.

Yeah, you see it every time.

Zzyzx Road.

I would get that one right.


A one letter town name, Å, with a little circle on top, is located in this country.

What is Sweden?


Oh, okay. I didn’t know. I just guessed something Scandinavian.

All right, take off your watch.

Sure, if that counts as an article of clothing, I’ll take it.

I’ll make it count. In 2010, this town briefly swapped names with Google.

What is Mountain View?

Topeka, Kansas. See, you’d think I would know something like that. Topeka, Kansas.

Can I take my ring off?

His wedding ring came off.

Sorry, honey.

On Saturday Night Live, “Celebrity Jeopardy!,” Sean Connery was asking Mademoiselle to see a mispronunciation of this Lancaster County, Pennsylvania town, or maybe not.

There’s a few funny town names in that. I don’t know.


Oh, “Le tits now.”

L-I-T-I-T-Z. “Le tits.”

You know what? Pennsylvania has Intercourse. It has Blue Balls.



They have towns like that?


Are you serious?

In Pennsylvania, yeah. All right, took a shoe off.

His left shoe came off, for those that are listening.

To promote tourism, and this is 500, to promote tourism, this Welsh town decided to make its name the longest place name in Europe.

Like I’m going to know that.

This isn’t even fair. You can’t even pronounce this.

All right, I’ll just take my other shoe off. Dah, dah-dah. Okay. What was it?

I want you to try to pronounce that.

Oh, come on. Oh my god.

I’ll let you put your shoe back on. If I can’t pronounce it, then that shouldn’t count.

Thank god. Okay.

This is the last category. “Epic Rap Battles of History Speakers.”

I’ve been avoiding this one. This sounds bad. All right.

This is a web series, depicting historical figures rapping against each other. You must identify the historical figure who is portrayed as speaking the lines.


Okay. “I keep my rhymes pure like my food and drugs, and I’ll bust a trust fund lush with my American muscles.”

I’m not getting it. I don’t know.

They named a teddy bear after him.

Named a teddy bear after him?

Didn’t they name a teddy bear after Theodore Roosevelt? For 200. Well, take your other shoe off.

It’s getting dicey here.

All right. “You need to take control of your life you’re given. They call me Übermensch, because I’m so driven. You need to take control of your life you’re given. They call me Übermensch because I’m so driven.”

Friedrich Nietzsche.



I think you did pretty well. You still have your pants on. You still have your shirt on. You did well, way better than I would have done.

All right, so we’re going to play one more game. I think we know each other pretty well, from a business perspective, and a professional level. We’ve worked together for a couple years now, but I think I’d like to give our listeners a little bit more of Scott Shrum, with a game that we’re going to play called “Never Have I Ever.” Have you ever played this?

I don’t think so. Not the card game version, at least.

Pretty simple game. We both have 10 cards. You have to answer the question honestly. You get three passes, and then the first one to seven, with a truthful answer, wins.

Okay, and my clothes stay on? I’m asking. My clothes-


Okay, cool. All right.

Yeah, there’s no taking off any clothes here, for this one.

I’m in business.

You’re good to go here. I will go first here.

“Worked at a kid’s birthday party?” Absolutely. I was a DJ when I was young, all the way up until my 20s, basically. I worked at many kid’s birthday parties as the DJ. That was a pretty easy one for me.

Was that a good job? Did you enjoy it?

Loved it.

Or was it- Okay.

Oh, it was the coolest job ever. I was 16 years old, going to sweet sixteens every Friday and Saturday night. How awesome is that? Getting free food, gourmet food. Getting to meet girls that were my age. It was the coolest job ever, and I got paid on top of that.

Nice. All right, “Been hammered at a movie theater?” I have never been hammered at a movie theater.

I don’t think I have either. Do they even sell, well, I guess some of them now, Movie Tavern.

Oh yeah, that’s a big thing. Yeah.

Nowadays they have that but back when we were growing up, they didn’t have that.

No, and I’ve never been-

Unless you got hammered before you went to the movie theater, right?

I can’t say I’ve ever been hammered at a movie theater.

Okay. “Done a keg stand?” Who hasn’t? That’s one of the things that we did when we visited my buddy at a college. The same buddy that also gave me the mushroom. Man, talk about a bad influence, this kid was. Yeah, we’ve done keg stands there. That is, “Yes.”

All right, my next one. “Ran out of the office to have diarrhea somewhere else?” I’m going to say no, although I can come close. One time, this was in my last job, I was in a meeting, and somebody was talking about something. I just said, “I’m sorry, I don’t care about this,” and I just got up and walked out.

When you walked out of our door to our suite, you were outside. I just walked up to a bush and threw up in this bush twice. Just two large volumes; threw up. That’s as close as I’ve come.

Got it. So you never had an accident in the back of your pants?

No, not while I’ve been a grown-ass man.

I don’t think I’ve ever. I was with a friend that did once. We were working on- He had a job, and he was delivering sodas or something. He’s like, “Man, I’ve got to go so bad. I don’t know what to do, man.” I’m like, “What do you mean?” He’s like, “I’ve got to go.” He goes, “I think I just went a little.”

Oh Jesus.

Then he goes, “I just went a lot.” He’s like, “Oh my god, what do I do now?” I’m like, “Oh dude, I don’t know. Go to the bathroom.”


Yeah, that has never happened to me but I was with somebody when it happened.

Oh, brutal.

Which was not fun to watch. “Danced drunk on the top of furniture?” No, I don’t think I’ve ever danced drunk on the top of furniture. I’ve danced drunk, but not in that setting.

All right, let’s see. “Opened a beer with my teeth?” Wow, I’m not that much of a man. So no, I don’t think I’ve ever done that.

You still have all your teeth.

I still have all my teeth. Wow.

Do people even do that?

That’s hardcore.

I have opened a beer with my ring. That’s a trick, right? You just pop it, and it opens?

Yeah, yeah. I don’t know, I’ve opened cheese sticks for my kids with my teeth but I can’t say I’ve opened a beer with my teeth.

“Worn Reebok Pumps?” Yes, I was just, actually, I am not even lying, man. I will show you this right now.

Those are so fresh.

We have a mutual buddy, his name is Alex Valencia. It’s so random that this question would come up. I was texting Alex, because I bought a bunch of shoes. I was at this sneaker store recently and I was buying a bunch of shoes. I sh*t you not, I texted him saying, “I just got the new Reebok Pumps.” Right there, there’s a picture on my phone. You can verify it.

Yeah, yeah.

I was kind of kidding, I just was being a little bit nostalgic. But that’s funny that this would come up here, just like that.

Oh, I remember in high school, the first kid who had those. He was like a celebrity.

Right, coolest kid in the whole school, man. Rocking those Reebok Pumps.

Nothing cooler. All right, “Made breakfast for someone in bed?” Yes. Yes, I have done this. I’ve done this actually for my wife, and for my kids when they haven’t been feeling well. Yeah.

See, you’re a good husband, and a good father.

“Gambled my rent money?” I had a time where I was pretty addicted to sports betting for a while but it wasn’t rent money. I guess it would be mortgage money, back in those days? When I was young and I had a couple houses, I had multiple houses, and I didn’t probably have enough money at the time to carry all of the houses at once. So, I guess I was feeding into mortgage money when I was gambling, back in those days.

That was after your keg stand, you did that.

“Gone a year without changing the Brita filter?” Oh, I don’t think so. No, I’m a by-the-book kind of guy.

Yeah, I can see that.

Yeah. No, that sounds gross. I’ve never done that.

Had sex on the first date? I have had sex on the first date, yes. That’s pretty easy.

Look at you. “Eaten something out of the garbage?” I have definitely done that, yeah.

What was it?

This actually just happened, in the last couple weeks-

It’s something that you do currently, okay. It wasn’t when you were drunk at the movie theater.

I’m nibbling on something out of the garbage right now. This just happened in the past week. We were at In-N-Out, and I took all the stuff. We were done, and then I threw everything in the trash. Then my daughter said, “No, those fries. We were still eating them.”

Then I looked in, and I was like, “Well, they’re just sitting on top. They’re not really touching anything.” So, I pulled them out, and we just kept eating them.

Yeah. In-N-Out fries? You can’t throw those out.

Yeah. I’ve also, I think I’ve fished pizza crusts out of the garbage.

Have you?

Not something that’s been in there for 3 days. But I’m like, “You know what? No, I’m going to nibble on that. I’ll pull it out.”

I had a friend that had this weird thing, where he would only eat four french fries at a time. He’d have to pick up four french fries, and eat it. Then if he came down, he had three left? He would throw it out. That was just his superstition.

That is full blown OCD. Geez.

Yeah, it totally was. Yeah. We’re tied at 6-6 right now.


“Taken Adderall to be the most productive person ever?” I’ve tried Adderall one time. Somebody gave it to me, and I just wanted to see, what was this whole thing about? It’s the weirdest thing. You take it, and you go to the bathroom, and your whole pupils are dilated. They’re just huge. The next thing you know, you’re just talking to everybody.

I was at a conference. It was one of the legal conferences, and I’m really tired. Paul, a mutual friend, I won’t say last names, gave me this thing. He’s like, “Here, why don’t you try one of these?” I’m like, “Okay,” right? I’m like, “Will it wake me up?” “Yeah.” “Okay.”

Then sure enough, I was talking to everybody. I should do that. I drummed up so much business because of that pill.

I know who you’re talking about, and this person, Paul, zips around conferences like a dragonfly. Now I understand why.

“Fallen off a boat?” No, I’ve never fallen off a boat, although I fell off a dock into the Charles River, in the pitch black one time, when I was in college. I almost drowned, yeah.

Did somebody have to jump in to try to save you, or what?

They couldn’t even see me, because it was so dark. But I was able to, I got the wind knocked out of me when it happened, but I ended up being able to pull myself back up. That was actually a little scary, yeah. No, I’ve never fallen off a boat.

“Given a homeless person money, just because they had a dog?” I don’t know if I’ve given them money just because they have a dog. But sometimes you see homeless people out there, and they’re in a wheelchair. They’ve got one leg, and they’ve got a dog. You feel bad for the person, but you also feel bad for the dog, right?

Yeah, for their pet, right?

Because they didn’t really choose that life. Sometimes I will donate both to the dog and to the human being that’s with the dog.

That’s tough. When I see the pet, that tugs on my heartstrings. Yeah.

“Set my hair on fire?” What am I, Richard Pryor? No, I’ve never set my hair on fire.

“Called in sick because I was hungover?” Oh, I used to do that once a week, when I was in high school, man. Yeah. I’ve done it.

You had a more fun high school experience than I did.

“Got sucked into a pyramid scheme?” Oh my. No, I can’t say I’ve ever been sucked into a pyramid scheme.

I can’t see you, you’re very skeptical about stuff like that, right?

Yeah. Yeah. No, not my cup of tea.

All right, so it’s a tie here. It comes down to this last question here.

“Created a fake Twitter or Facebook account to stalk another person?” I’ve never created another fake Twitter account to stalk somebody. I have created fake Twitter accounts before, to try to get in touch with different people, but never to stalk anybody.

So your definition of stalking goes around.

All right, “Lost a fist fight?” Oh, god. I think in my life, I’m 1-0 in fist fights. I was never really a fighter, but the one time I got into a fight, I won.

I was never really a fighter, but the one time I got into a fight, I won.

What was that like? What grade was this in? What the heck did the kid do?

You’re not going to believe this story.

Do tell.

I was in second grade, and the kid was, I think, in seventh grade.


It was on the school bus. I was this little kid, with this impossibly large backpack. This kid who was way bigger, we were all- It was a Catholic school, where it was K through eighth grade, all on one bus. Really big kids next to really small kids.

I got up as we were getting off the bus, and this huge kid pushed me over. I tipped over, and I got up. The backpack was no longer on my back. I just jumped up, and I nailed him so hard. He staggered, and then just got so embarrassed that he ran off the bus.

Everybody was laughing. He never messed with me again. That was barely a fist fight, but yeah.

I was waiting for the Christmas Story

Oh, like Farkus? I just unloaded on him?

You just got him, yeah, and you just, yeah.

No, it was just one blow. I mean, a second grader, how hard was I hitting?

Of course, yeah.

He ran away and he was just permanently embarrassed by that story. Then I was like, “Yeah, I’m kind of a badass,” and that was it.

“Don’t mess with this second grader.”

So I’m calling it 1-0.

Well, I’m going to say that you won, because the Facebook, Twitter account was a dodgy answer.

It was a little dicey there.

So, I will give you this game here.

Thank you.

There you go. Since you drove all the way down here, I do have a gift for you. This is a gift that you played a major part in because you went to the COO Alliance, and there was a thing called the “Big Idea Calculator.” It was line four on the “Big Idea Calculator.” What was the “Big Idea Calculator”? What was that?

When we get together for the COO Alliance events, run by Cameron Herold, he gives you this “Big Idea Calculator.” Every time an idea occurs to you, or you hear somebody else say something, and you’re like, “Oh, that could have a big impact on my business,” write it down. Then you try to quantify it. You just, “Oh, that’s a $10,000 idea. That’s a $2 million idea.”

One of the ideas, that for some reason came up during the course of our conversations, when I was at that event, was you writing a book. I wrote it down. I was like, “I’ve got to talk to Jason.” Because I think at the time we kept- We were going to do it, and then we didn’t do it.

We were interviewing cool people, remember?

We were going to do it. Right.

We were like, “Should we do it?”

There were some-

“Should we wait?” Yeah, mm-hmm.

Right, there were some false starts. Then I was like, “No, we’ve got to just do this. This is a no brainer.”


Yeah, that was-

So that was- it was I guess, accountability. It really was. Then what happened was, you had to put that in an envelope, and send it to me.

Right, yeah.

So I received it.

That’s what I did.

I’m like, “What is this?” It said, “Number seven, Jason needs to write a book,” and I’m like, “Okay, well I guess we’ll get started.”

We ended up engaging the company, Scribe, to help us out. It was published under Lioncrest. Eighteen months later, we now have a physical hard copy book here.

Thank you.

So, thank you for that.

Thank you so much.

It’s signed in there for you and everything.

Awesome. I’ve got another physical copy coming from Amazon.

Oh, do you?

But now I’m going to-

Well, now you can leave me a review.

Yeah. That’s right.

So see? There it is.

I’m a verified buyer. Thank you.

Well, Scott, I sincerely appreciate you coming into the studio. It was really fascinating. I’ve known you for probably 5 years now, maybe a little bit more, but it was interesting to learn a little bit more about your childhood.

I can see you going back to your childhood, your eyes were lighting up. When you got into MIT, you were reliving that moment. It was fascinating to watch, so thank you.

It’s a highlight, for sure. Thanks, Jason.

Yeah, I appreciate you being on the show.

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