Tyler Gaffney Super Bowl Champion, MLB Prospect, and Tech Entrepreneur

Interview on the Jason Hennessey Podcast 06-22-2022 - Episode 31
Tyler Gaffney

Tyler Gaffney Champions Family, Athletics, Education, and Web3

Today, it’s my great pleasure to be sitting down with retired NFL running back, pro-baseball outfielder, entrepreneur, and family man, Tyler Gaffney.
Listen in as we trace his whirlwind sports career from playing college baseball at Stanford and being minor league captain, all the way through playing football for the New England Patriots and winning the Super Bowl.
But just because he went from taking the Megabus to charter planes doesn’t mean his life is all glitz and glamor.
Today, we get deep and vulnerable into the non-Facebook version of life, the rigorous reality of a pro-football player’s schedule, healing from a plague of injuries, having kids at 24, and the bold sacrifices one needs to make in order to win the game and live life to the fullest.
Please hit the play button at the top of the page, and thank you for following along to today’s humanizing episode.

In this Episode

[01:24] Jason introduces Tyler, and our guest promotes the use of public transit, telling us about his days taking the Megabus from Carlsbad, CA to using the metro today to get to Hennessey Studios. He divulges that his NFL career felt surreal, and is excited to now be in this “dad phase” of his life.

[04:45] Tyler describes how he realized his athletic gifts while he was in elementary and middle school, and the unconditional love and devoted support his parents showed him. He also mentions how his efforts outside the classroom helped get him into Stanford.

[11:30] Tyler discusses switching his focus from baseball to football during high school due to his disciplinary record. He began working out instead, improving his football skills, won a state championship, and scored his first collegiate touchdown against USC.

[16:00] Jason inquires about Tyler’s popularity during his senior year at Stanford. Tyler tells a couple stories that showcase his love of Stanford’s culture of “no-big-deals on campus.” He also shouts-out a couple friends who’ve succeeded after Stanford.

[20:46] Tyler goes into detail about his athletic journey in college, being drafted to play professionally in the Minor Leagues for the Pirates, and then into NFL for teams that included the Panthers and the Patriots.

[26:51] Jason hears the story of how Tyler grew his family. Tyler recounts meeting his wife in Downtown Palo Alto, finding out they were pregnant with their first child, and the amusing story of their civil marriage during their second pregnancy.

[32:04] Jason and Tyler share stories of how their sons have struggled in sports, and how it’s up to parents to guide them towards a variety of interests. Jason also tells his Karate Kid story, and they discuss how wrestling and sports can have disciplinary benefits.

[40:47] Jason asks about Tyler’s motivation for returning to the Patriots. Tyler explains how being away from his family, especially during COVID, made him realize that he was craving spending more time at home. He also praises Jason for being a family man.

[46:37] Tyler lists a couple reasons why he’s wary of social media. Jason gives us examples of how being vulnerable to his followers and business partners have created better relationships. Tyler argues that being vulnerable equates to just being human.

[53:55] Tyler tells us about the different ventures he’s involved in today. He’s working on learning and investing in IoT, Web3, e-commerce, and blockchain technologies. He also gives us a glimpse into his investment strategies and the people he relies on.

[01:04:14] Jason asks Tyler about who decides where to eat between him and his wife. Tyler reveals why they rarely go out to eat, what he likes to cook, and how his wife gets complimentary meals. Jason proceeds to recommend dining at The Magic Castle.

[01:06:23] Tyler reflects on his role model, the things that motivate him to be better, what makes his parents proud, being teammates with Tom Brady, and much more during today’s signature segment of “Hennessey Heart-to-Heart.”

[01:22:57] Jason and Tyler look forward to meeting each other’s families as they end today’s on-air conversation.


Jason Hennessey: Tyler Gaffney, thank you for coming down to Hennessey Studios. Drove all the way from-

Tyler Gaffney: San Diego, best place in the world.

San Diego, and you didn’t drive.

I didn’t. I’m a big proponent of public transit. Did it all while I was at Stanford.

My now wife, actually, when I was first signed in the NFL, we got back to go visit Stanford, have a great time.

I actually had booked the Megabus many-a-times before I knew her. Not that she was expecting anything, but I think she might have expected that we would drive or fly, and I’m like, “Nope, we’re taking the bus from-” It’s a 9-hour venture.

And needless to say, that was our last time taking the Megabus on a 10-hour trip, so I love it. I just get to zone out.

And I got a 5-year-old and a 4-year-old boy, so when you get some time to yourself to get some things done or even just take a mental break, I’m all for it.

Oh, that makes a lot of sense. You get a lot of work done, I guess. Yeah.

No, my wife, so when we first met, we went on a date, our first date, and I tried to take her to the Rio Buffet. I didn’t have a lot of money and she was not having that. [laughs]

It’s the thought that counts, I thought.

I had to splurge, so that’s the same. That’s my bus public transport story.

I want to get into, because we had met in Kentucky. There were some pretty fascinating people on the bus.

One was a World Series of Poker champion who has been a guest on the show.

And another one had a Super Bowl ring and I’m looking around and there’s only one guy that looks like he has a Super Bowl ring on the bus with us, and it was Tyler.

And then come to speaking with you or I guess you really didn’t have too much of a voice. You still are living a pretty fascinating life. Huh?

It’s funny that you say that because just in the car, we had a coffee date with my wife, I dropped the kids off, we go get coffee, and this is our time to just be with each other for 45 minutes before I left.

We were talking about just, I don’t know, I think maybe someone on the radio or something said, about the NFL and I said, “Honestly, that happened and it was so crazy and it’s a crazy lifestyle and it’s unrealistic for anybody to live through.”

And so, that’s a whole ‘nother conversation of why people have problems post-NFL, but it feels like a dream. I almost don’t even feel like that happened.

It feels like a dream. I almost don’t even feel like that happened.

Of course, I experienced it, but I’ve talked to plenty of guys, 50, 60 years old now, who played in the NFL for 10-plus years, and when they watch Hard Knocks and really advertised NFL media, they can’t even believe that happened in their life and that is all your life.

And so, for me, luckily enough, I played 5 and a half-ish years. That’s a pretty big percentage of my life where I only did one thing.

And still, we went on duck boat tours, Super Bowl, the Super Bowl Parade out in Boston, which is insane and I’m going to definitely go the next time they win, but it does.

It feels like it went right by and here we are now in our suburban Carlsbad home, having another phase, but it is the best phase.

Yeah. The dad phase, right?

Exactly right.

Before we get into the family, because I certainly want to know a little bit. I’m a dad, my family is everything for me too, but I want to go back to the 7-year-old Tyler.

Were you always just naturally gifted with sports? Just anything you played, you just excelled at or what?

Yes. The short answer is yes.

I definitely was gifted younger and it stood out. I think part of it was my athleticism, but the other part of it was I matured faster. And so, you can tell right away when you have-

In fourth grade, there’s a bunch of kids standing at 4-foot, and then there’s a kid standing at 5-foot. I had the peach fuzz mustache in middle school. I joke around that, I’m 31, I’ve looked 30 since I was 15.

I haven’t aged a day since I was 15, which it wasn’t too helpful when I was 15 but, I guess, for buying beer. So I was the guy to do that.

Seven-year-old Tyler realized really quickly that he liked winning. He liked, if we want to go deep, liked the approval of others by winning and I think that’s pretty natural, but it became clear to me as I moved up and played older kids in different sports that being athletic or being gifted or whatever you want to call that wasn’t going to get me to win.

And so, I started at a pretty young age of, I’d say 12, probably middle school, when I started, like, lifting weights, practicing more, working out, whatever, however you want to classify that, but it was.

It was just play as many sports as I could and try to win at them all. And it didn’t matter if it was racquetball in PE, track in PE or soccer, baseball, basketball. I didn’t play football till high school.

You learn how to win, and the game within the game, and then that is fundamental for everything.

You learn how to win, and the game within the game, and then that is fundamental for everything.

And what was home life like? Parents and neighborhood you grew up in and-

My parents are the best. We grew up very low to middle class, but I was the wealthiest person in the world. And whether I knew it at the time, I think as you become a dad yourself, you start to see the stresses, everything that goes into being a parent.

It isn’t as simple as just raising them. How do you raise them, what school do you want to go to, who do you associate with, make sure you bring them home to practice for the therapy that they just went through, the jiu-jitsu they’re in, baseball.

There’s so much that goes into it and my parents were the first ones to help me in all of those aspects. They probably drove tens of thousands of miles when I was doing travel baseball every year.

Yeah, and that never changed up and through Stanford where we played the Pac-12 Championship in Arizona and beat them. My parents were there. And then they drove from Arizona, I think it was the next day, to Stanford.

I have no idea how far that is, but it’s 10 to 15 hours, and they were there at my senior ceremony where I accepted the awards and whatever, and then off to the Rose Bowl.

That is just what they did and who they were and so they were the prime example of just undevoted love.

Talk about proud moments. They’re probably there when you hit your first Little League home run over the fence.


Ran around the bases, looking up at mom and dad in the stands, seeing how proud they were.

Oh, yeah. “Here we go, buddy.” I could hear that. My mom would yell that, and I would hear it, and it still rings in my head.

And you don’t appreciate it until you do. You don’t realize it until you’re in it.

One of my biggest regrets actually, is at some point I told my parents, I hushed them and was like, “You’re embarrassing me.” And it was super sad, looking back on it, that I would say that because all you want to do as a parent is love.

I’ve told them that since, “I’m so sorry that I ever, like, did that,” because I noticed they started being quieter. And this was probably when I was in college that I said this, maybe in high school, but they were just so proud.

And it’s not like they were, like, yelling and doing all this stuff.

No, it was my dad would say at the Rio Buffet, “My son scored a touchdown today,” to the waiter and I was so embarrassed that he would say something like that.

And looking back on it, it was just a super cool moment by a super cool dad.

Looking back on it, it was just a super cool moment by a super cool dad.

Yeah. So, as parents, that’s what we do, is we live vicariously through our kids and you’re doing it now.

What did your mom and dad do for work?

They were in tech sales and tech distribution, and that’s how they met. One was selling, one was buying, and then they developed that relationship and now we’re here.

It’s interesting because not only did you achieve the ultimate high in, like you said, Little League, as far as getting a good education and taking school seriously because Stanford is not Community College of Southern Nevada.

And sometimes athletes are gifted with athletics but maybe not gifted in the classroom, and it seems like you had both of those skills.

Gifted in the classroom is a stretch, for sure. I worked for it. I definitely was on the, in terms of Stanford’s grading schedule, I was barely in.

I tested really well for SATs. My GPA just showed that I didn’t give a shit about homework at times. I didn’t put that extra effort in.

But also on that note, I’ve seen so many memes or little blurbs about you don’t need an A+. Those B+ students are usually because they’re busy doing other things. It’s not because they chose, “I’m just going to sit on my ass all day and get a B+.”

You’re spending more time lifting weights.

Yeah. Whatever it was.

It was working out. I was our vice president of our school. I was doing the broadcasting. I was doing other things, which actually got me into Stanford, was because I was doing everything rather than I wasn’t just an athlete and just barely made it, educational class.

It is tough. Then, you go to Stanford and you just get wrecked.

So, before you get into those Stanford stories, did you have an opportunity to play professional after high school?

I didn’t.

I got in trouble my junior year and I actually had my junior year of baseball stripped from me. I got to play 20 games, maybe, that year. No, not even 20. I think I had 20 at-bats, is what I meant.

I see what you’re saying.

Yeah. I got in trouble, too many referrals, too many detentions, and they made me ineligible for an entire semester. And so, I lost baseball. I wasn’t allowed to practice with the team. I wasn’t allowed to be in the weight room.

The dean of students at the time really had it out for me and he was looking for me to be in trouble so many times and I occasionally gave it to him.

That was devastating but really, I just worked in the weight room from there on, and then had the best senior season that I could have ever had in football.

In football.

Yeah. In baseball. I had a great season too, but football was a different beast.

So, football was your number one sport in high school?

Yeah. Baseball could have been, because I played baseball my whole life but as soon as that year happened, I went from, I don’t know, 1,600 yards as a junior to 3,000 yards the next year.

And I could just tell I was bigger, stronger, faster because all I did that season was work out.

I could just tell I was bigger, stronger, faster because all I did that season was work out.

And what position did you play?

In baseball?

So, both, I guess.

I played center field and right field in baseball.

And then football.

And then I’d bat 1 through 3, depending on whatever it was, and then football, running back.

Running back.

And so, senior year of high school, you had a great year. Did your school go to states or anything?


They did?

Yeah. We won state championship. It was the first one for us.

It was a little different back then as it is today, which I love the way they do it now with open division, Division 1, and you move tiers. For me, it was based on attendance.

Great year. Did you have options to go to other schools or did you just know you were going to Stanford?

No, I was actually pretty committed to USC at the time.


Yeah. You had the Reggie Bush, Matt Leinart, just “the era” of USC football.

And I was pretty convinced as a SoCal kid, that’s where I’m going. They had Joe McKnight at the time and I was ready to let him play, taking the next role. I only live running backs, but so do most teams.

My dad loved Notre Dame. I had a bias towards Notre Dame in a good way. But the problem then, which is very different now, is I wasn’t exposed to any colleges.

Social media was nothing. I think the iPhone came out at the end of my senior year. So, just being able to browse and look around- I got an offer from Auburn, and I think Auburn is a wonderful school.

My 17-year-old self that got an offer, literally just moved it to the side. “What’s Auburn?” And I wish I would’ve taken my trip down there, but I ended up being between Notre Dame, USC, and Stanford.

Then I got into Stanford.

Funny story. Junior year, I walk onto Stanford. I’m looking up with the flags. It’s the Pac-10 at the time. And I don’t know this, that they’re even in the Pac-10. And I look up. I’m like, “USC, UCLA, Oregon State, are they in the Pac-10?”

And that just goes to show how much you didn’t know. And I didn’t even know how good or bad their football team was. Their baseball team was always great. Every 4 years they were in the college championship.

And so, it was that moment. I was with my dad and we were walking in front of the baseball fields where the flags are. And I said, “So, maybe I could go here.”

And they had Toby Gerhart, who was football and baseball at the time. And so, it was like, “I can do that. He can do it, I can do it.”

You walked on, you said. Did you get much playing time as a freshman or what?

I got a little bit of playing time. Actually, my only touchdown I scored was against USC that year.

Wow. That’s cool.

It was the Pete CarrollJim Harbaugh “What’s Your Deal” debacle.

I was the last touchdown.

When Harbaugh basically- We were up by 25 or 30 and it’s 2 minutes left in the game and we’re just pounding them, driving down and we get down to the 5-yard line and they put me in, and I just pound my way to score a touchdown, just so he could score 50 or 60, whatever the next threshold was.

But yeah, that was my first ever touchdown.

By your senior year at Stanford now, now you’re a big deal on campus, right? You’re probably a celebrity on campus.

There is no such thing as a “big deal” on Stanford campus.

There is no such thing as a ‘big deal’ on Stanford campus.


No, it’s a tough pill to swallow as an athlete. And not that you want to be a big deal, but when you do really cool things in pretty tough circumstances, you want to be recognized by your culture and your family.

But we come back from the Pac-12 Championship on the bus. We have 17 people there.


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You look at SEC schools, the Big Ten, Big 12. They win a game, they might have 40,000 people waiting for them to get off the bus, just a regular game. We just won the Pac-12 Championship and it was depressing that there was 17 people, 10 of which are parents.

And so, anyway, but you can’t set a standard when you have Olympic athletes there, which there’s a dime a dozen Olympic athletes.

You have people dropping out or creating the Ubers and Adobes of the world as 19, 20-year-olds. You have prince and princesses of different countries, so you have all this melting pot of-

Big deals.

Big deals. What’s a big deal?

What’s a big deal?

Yeah. And what’s really cool about Stanford is nobody wants to really be a big deal. They just show up. I was with Toby Gerhart and Andrew Luck when they had gone to the NFL and they’d come back.

There’s a frat party. And a lot of times some of the frats will make it Stanford-only and so you had to have your Stanford ID to get in.

Toby Gerhart, Andrew Luck, both the NFL, both first rounders, can’t get in.

Can’t get into this party. [laughs]

No. No, Stanford ID. Yeah.

They’re just like, “I don’t really care,” and had to find people to do that, but in any other place in the world, those guys have a posse around them, just following them around.

Here, they just walk up and they can’t get in a party.

Huh. Different world there. Huh?

Damn right, in a really cool way.

And it’s small. There’s only 6,500 undergrads, so we’re not exactly filling out any stadium with students. Half the students don’t go. The other half bring their laptop and use the wifi.

And then you have a 1,000 or 1,500 that maybe really care.

Outside of the sports side of it, as far as the education at Stanford and the network of friends that you’ve built there, what are some cool stories, friends that went off to start big companies or whatever?

Yeah. I think some really cool stories are- I just was in my buddy’s wedding. His name’s Jack Mosbacher. He went from writing a thesis and research in Jerusalem to New York theater, making the Broadway circuit or trying to do that.

Then he started his own band, which was going really well right up until COVID. And if you weren’t established and had a cult following you weren’t going to make it.

And so, he starts his own venture group with two other guys and they are crushing it, and that’s just one story.

Sahil Bloom, if you haven’t seen his Twitter threads, you’re missing out on life, @SahilBloom.

He is one of the most intelligent people I know, but also, he’ll listen, where a lot of those psycho intelligent people, you talk to them and I could ask them how they’re doing and they’re just still talking about whatever business, the next move, where he listens.

And so, he’s a dear friend of mine. He just had a kid, but he was a Stanford baseball pitcher and I’ve watched his progression through life, of all things life, go from 215 pounds, maybe a little stocky, little chubby to a extremely fit, well-groomed now dad, who has been just uber successful in the venture world, private equity world.

And so, I could just keep going on and on and on because the odds of making it professionally in sports are minimal.

The odds of making it professionally in sports are minimal.

Oh, they are, yeah.

Yeah. And even that, making enough money, if you do make it, making enough money to not do something next is even a smaller percentage.

And so, I think everybody who went to Stanford went to Stanford because sports wasn’t the end. Even if I had a 10-year career, what am I going to do from 34 to the rest of my life?

So, it says that you’re 31 years old and you’re retired.

Yeah. I like to be incognito. I’m retired from football.

So, you from Stanford and then you had an opportunity to play professional football or did you get drafted or did you have to walk on? How did that all work out?

When I was talking to you earlier about the dream, how it’s felt like a dream…


Junior year comes around for baseball and I’m All-Pac-12 or All-Pac-10, whatever it was. I hit .330, .325, whatever, 2 years in a row.


Freshman year, sophomore year, my numbers were so scary identical, that it’s eerie with the at-bats, the amount of doubles, the amount of triples, the amount of home runs, it was the same.

I got all this love from different MLB teams telling me I’m going to be a high draft pick.

My junior year comes around. We play in the Fiesta Bowl and for football, we play in the Fiesta Bowl and lose to Oklahoma State. That was Brandon Weeden, who was 30 years old as a senior, and Justin Blackmon who was just insane in college.

They beat us, and I really remembered not playing as much as I originally thought I was going to. I had this whole game plan, the Wildcat, all these other plans for me. I didn’t play as much as I wanted, and I was selfishly frustrated.

I had a great season. Every time I touched a ball, I was averaging 7, 8 yards, so I was like, “Why am I not playing?”


So, that emotion by a 19, 20-year-old going into everybody telling me that I’m going to be drafted in the first 10 rounds, depending how good or bad I do, I slump my junior year.

Like, I slump. I’m not hitting well, my coach and I, he was just very old school mentality, and we’re not having the best relationship in general. I’m slumping.

He starts pulling me from games. I strike out to lead off the game and I’m out. I’m on the bench, so to have that, first off hitting is impossible in general. If you hit 3 out of 10, you’re a Hall of Famer.


If you hit 2 out of 10, you’re not on a team.


Somewhere in between there, there’s greatness.

So, with all that pressure of just trying to get a hit in general, if I get out, I might be on the bench. I ended up hitting .250 that year.

Now I’m in this predicament. I don’t really want to go back to football because I’m frustrated with the situation there. I did not have a great year in baseball. I ended up getting drafted in the 26th round.

It was the new CBA, and so they didn’t really know how to do the draft either, because all the rounds were slotted now instead of being able to pay different rounds, different money.

Like, if they picked up Tyler in the 26th round, originally, a year ago; paid me a million dollars and there’s no penalty. Now, if you get paid more than 100K in round 10 on, it’s a penalty towards the team.

That being said, I’m like, “I’m leaving, no matter what,” so I went and played with the Pirates. Played short season; hit really well; was captain of the minor leagues.

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I had maybe, self-proclaimed MVP of the team. I don’t know. I did well.

Where were you living? Where’s the minor leagues team?

State College, Pennsylvania.

In Pennsylvania? Okay.

Actually, I lived right by campus and that was when the whole Joe Paterno issue came about…

Oh, okay.

…and they pulled down his statue.

I remember driving by his statue on the way to the game or practice, whatever it was, and then when I drove back…


…and it wasn’t just gone. It was like a well-manicured area, and you would’ve never known a statue was there. It became part of the campus, like the campus just ate it.


It just was a new entire section.


You were like, “Wow. I swear the thing was right there. The statue was there.”


So, I leave, I tell them I go to the Rose Bowl Championship with Stanford. They were in it and I was just a fan.


They tell me that, “You have a year of eligibility.” All my best friends are on the team still. They’re my year. They’re all seniors, and they said, “You could come back.”

They’re just joking around. We’re all drinking, having a good time.


So, I started thinking, “If I came back, how do I make this happen?”

And so, within that week I basically had made all the calls to my agents, understanding, “Do I have to pay for this, or can I get a scholarship, because it’s football and not baseball?”

Well, long story short, I could get a scholarship, because it was football and not baseball. So, I call Coach Shaw and I tell him. I call the Pirates and I tell them that I’m going to go finish my degree and play my last year of football.

So, I’m going to miss this upcoming season, which would’ve only been the fall ball basically of the season of baseball. Then I have a- Win the starting job, had a great season, got drafted in football.

Right when that happened, I was like, “I’m not going back to baseball. The minor league life?” In football, you go straight to chartered planes and big money, and actually being able to live.

In football, you go straight to chartered planes and big money, and actually being able to live.


That was an immediate answer, drafted by the Panthers, played 5 years, football.

Went back to baseball after those 5 years. That was a bad choice in terms of life, wife, two toddlers, like newborn and a toddler in the middle of Altoona, Pennsylvania, which is a coal mining town, and we lived in a dorm room.

Oh my.

Yeah, it was a six-person suite dorm room, but it was just us in a literal dorm room. You know the blue squishy beds…


…that are, like, foam? Yeah. That’s literally what we had.

The only blessing that really came out of there was some great hoagies and my wife got Sports Illustrated while she was there.

I think just part of her story of growing was built there, even though it was a very tough time for my entire family.

Oh, okay.

I went back to the NFL 3 years later; Niners. Patriots; got cut last season and was like, “I’m good.”

You brought up your wife and your kids, and so where’d you meet your wife? What’s that story?

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I met her in Palo Alto. She was working for Adobe doing the Silicon Valley stint. She was at Box, and then she was at Adobe.

She lived on University Ave., right by the whole downtown Palo Alto, the bar scene, which is, if you’ve ever been there, if you walk it 10 minutes, you walk.

It’s over?

Yeah. It’s that. It’s great for the culture there, but that’s it.

So, met her, her sister actually dragged her out. She didn’t want to go. She told them they didn’t want to go, and her sister was like, you promised whatever brings her out.

We meet that night. I talked to her. I talked to her again. I asked my friends about her and they were like, “We don’t really talk to her.”

Was this after you had come back to play?

This is when I came back right before my last year in Stanford football. Yeah, so after the minor leagues, right before.

Got it.

So, this is my fourth year going on my fifth year.

So, we start talking. I don’t have a place to live, by the way. I don’t have money or a place to live in Palo Alto.

I actually boarded SAE and I lived in the SAE house. They let me pay X amount of dollars, and I say X amount because I don’t know. I don’t remember.

Mm-hmm. Yeah.

But literally, I had a double room, not a single room, but two bedrooms. I had to walk through my roommate’s bedroom to get out.

That was Alex Blandino, who’s a big leaguer right now.

Yeah. Mm-hmm.

I shared a wall with Kevin Hogan, who’s the guy that actually got me back in the NFL just due to video.


Little did we know then. So, anyway, I’m dating this woman.


She is in the real world making a healthy six figures and I am bringing her back to the SAE house. If she’s coming to my side, that’s where she’s coming.

She was my sugar mama for the time being, because I had no money. I needed breakfast burritos and we really fell in love quickly and had the best time at Disneyland, post Rose Bowl.

That’s one of our favorite stories, and then here we are 10 years later.


Yep, still happy, still in love

10 years, and so did you get married quickly?

We did not get married quickly. Wouldn’t be a great story if I did everything backwards.

Thinking about getting married, like ring, research, all that stuff, pregnant with Jaxon. Jaxon Jet, my first son.

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I’m trying to think how old I was. I was probably 23 when I found out, and 24, when we had him.

I watched my parents basically see other kids or their son have a baby or get announced a baby, and they’re so excited.


That was not the case for us. It was a very stale, dry room when my parents found out.

I’m the first, so I’m also young and we’d only been together for, I don’t know, 2-and-a-half years or so, something like that. Found out in a middle of nowhere podunk McDonald’s parking lot because she was feeling really sick at my friend, Sahil Bloom’s Thanksgiving party or something.

So, we’re driving back, pull over. Let me tell you what, when we found out we had about 2 more hours of driving and it was a long, quiet drive of-

“What are we going to do?”

“What are we going to do?” Yeah, exactly.


You never know. It’s your first one. We’re not married. We don’t know what’s happening. She’s newly moved out there.

So, we have Jaxon, I end up proposing in between. I told her, “Once we have this kid, I want another kid.”


So, I wanted him close together, so that’s where I’m at.


And so, proposed, got pregnant again.

Then we got married in the courthouse while she was 7 months pregnant and our son was, like, jumping around. We had a 20-year-old marry us or whatever, officiant.


My parents were there as witnesses.

My wife actually was laughing so hard and just because you’re pregnant, and I guess women that have experienced that, she peed her pants a little bit.

Is she okay sharing that story?

Yeah. Yeah. Well, she is now.

She is now.

No, I’ve heard her tell it a couple times.

That’s the reality of being a mom. If you’ve had kids, things go crazy.

That’s right.

Our kids are both 9-and-a-half pounds. I can’t imagine a 9-and-a-half pound watermelon…

Baby, coming out of you, right?

in my stomach. Yeah.

We still have not had our wedding, we will. We went back and forth about when we want to do that, but I think it’s like we have nine weddings this year to go to.

I think it’d be a lot of fun to wait 5 years, and when everyone’s done having weddings, it’s like, boom. It becomes this grandmaster wedding where everyone’s 35.

They hopefully have more money, more of their shit together, and we can really have an extravagant, but very intimate wedding, because I only want 50 people there.


We’re excited. We’ve talked about it.

Now, you’ve got a baby and you’re still playing college football, right?

No, this was the next year after.

Oh, so this is the next year.

This is right after.

Right after.

Yeah, yeah.

Okay. So, now you’re playing professional football at this time.

Yes, yeah. That was my rookie season-

In Carolina.

I hurt myself, first play of Carolina training camp, actually turning back to that, and like a 20-yard run toss left; get tackled, knocked out of bounds.

I stand up, so excited, this is the first run ever.


I go to turn, like I jump and turn and I felt my knee pop. I run back to the huddle and I was like, “That was weird,” but if you play football, shit’s going to pop.

I get back to the huddle, and I’m doing squats. My coach can tell that something’s wrong, but it’s not coming back.


Normally, you get hit and you just know you’re okay. You’ll feel around.

It wasn’t coming back, and I was feeling unstable and I tore my lateral meniscus right out. That was a plague of injuries that had started.

I tore my lateral meniscus three times in my NFL career, all non-contact, all during practice, never been hurt before in my life. Never had surgery. Then all of a sudden, here come 3 and 5 years really quickly, and they’re all season-ending.

So, honestly, one kid and just a wife with a baby is very simple living, still.

Yeah, of course.

Might as well be like an accessory. I tell people one is easy. Two is, 1+1=10.

Yeah, of course.

All of a sudden, it becomes so many things are happening every day.

How many months apart are the two boys?

Almost 19.

Nineteen? Okay…

Almost 19 months.

,,,so my boys are 21 months apart.

Yeah. Yeah.


They’re “Irish twins.” Is that what they’re considered?

Irish twins.


Yeah. So, my one son got held back in first grade and my other son was the youngest in the class.

So, they actually went through school together in the same grade and they graduate this year. Right.




Like you, I played baseball in high school. I played football. I was a big wrestler in high school, but I love baseball, and so-

Everyone should do wrestling.

Did you do some wrestling?

I did not.

You did not?

I regret, not that I wasn’t just sitting on my ass.


I played other sports. I think wrestling, jujitsu, gymnastics, which is what I’m putting my kids through, minus wrestling, jujitsu and gymnastics.

It is so good for your body awareness and with wrestling, like leverage.

Oh, yeah.

I watch these old linemen that have wrestling backgrounds and they just manhandled other grown men, because they understand, and they don’t need to be that strong.


You have your Trent Williams of the world who are damn-near 7 feet, 400 pounds. He doesn’t need wrestling.


He’s just going to be a block.

That’s right.

Where I watched these only 6’2,” 300-pound guys just manhandle people because they get it.

So, similar to you, I was 7-years-old and a friend of mine was into wrestling I guess since he’s 4. His parents kind of got him in, and I got asked to go to a tournament just to watch him.

It was almost like The Karate Kid story where they’re like, “Are you in for this tournament?” I’m like, “Yeah,” and like here’s a belt kind of a thing.


So, I ended up wrestling in the tournament and I won the tournament.

So, I’m like, “Maybe there’s something here with this.”

So, from that time, I just pursued wrestling and I attribute a lot of my business success, if you want to say success, to wrestling days.

Just the dedication, no one to blame kind of a thing.

Where I was going with that story is so when I had children and we got them into Little League, the goal is, “These kids are going to be amazing in baseball and sports,” and that wasn’t the case, man.

So, my one son got up there and he was the kid that if he foul-tipped the ball, the whole crowd would say, “No!” [laughs]

Yeah. Yeah. Yeah, of course.

The kid in right field, the only one that’s wearing the helmet.

Yeah. Yeah. Yeah. I love that.

But it wasn’t his thing, but as a proud, I’m like, “Man,” but they’ve got their own talents, right?

Of course.

You use it-

You just try to navigate-



So, your boys, what are they into? How old are they?

Yeah, they’re 5 and 4.

Okay, so they’re still young.

Yeah. Jaxon Jet and Conway Bo.

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Love it.

So, Conway is still, he’s 4 going on 2. He loves being a baby.


He loves being mama’s boy, he loves cuddling. This is not to lessen the fact that he is Bamm-Bamm from Flintstones.

Yeah. Yeah.

This guy will run through a window, break everything, make messes, he is nuts.

But when he wants to be loving and a baby, he’ll literally talk to you regular, and then he’ll turn this voice on where he’s just a baby. He’s talking like a baby.

So, he’s into whatever everyone else is into at the time.

Okay. Yep.

Where my older son just started playing sports and wanting to go back, so that was the first goal.


Have fun…


…want to go back. He quit.

We tried soccer 2 years ago. We tried gymnastics 2 years ago, little too early. He just didn’t want to go after a couple weeks. He was just so adamant and cried about it.

What had happened was we took a step back, let him just do whatever he wanted again for the time being.

Then we introduced baseball, and now we just introduced jujitsu, and we like the fact that he wants to go back. I don’t care how good you are, because honestly, he was probably one of the worst on his baseball team.

It was his first year, and it wasn’t all those kids’ first year. As a dad and someone who’s played baseball, I can easily tell you he is the worst, but solely for the fact that he looks at his shadow when he is trying to hit.

Oh, really?

I was “dad pitching,” like doing this and I’m watching him, he’s a lefty and he’s looking at me, and then he starts looking down at his shadow and he is wiggling.

I’m like, “You’re never going to hit the ball if you’re not looking at this right here.”

“Hit the ball.” [laughs]

Yeah. So, long story short, he’s figured that out and now he hits it and a couple people have cheered for him.

I think it’s that, I don’t want to say drugs for a 5-year-old guy.

It is.

That’s exactly what it is.


Yeah. It’s that confidence. It’s that reassurance. It’s that gratification and same with jujitsu now. When he wins a spar or he does the right move, their coaches are really good at reassuring them.

But they’re also good at ripping some of the older kids’ ass, because it’s 6 to 10. So, these 10-year-olds who should be leaders are mouthing off or doing whatever, 10 pushups, they yell at them.

My son gets to watch that, because he’s easily the youngest for 6 to 10 and he’s 5.

They don’t listen to dad. I could yell at him and he just cowers, where someone else yells at him, he’s like, “I’m going to do better. You just keep yelling.”



The beauty though, I guess from the bright side of being retired is you’re there to see the games and stuff, because most professional athletes are on the road, right?


While they’d love to be at the games and stuff, that’s their job-

Of course.

They’ve got to get on the plane, right?

There is no off days, sick days, whatever you want to call it from about July to January.

If you’re on a good team, through February, you miss anything during that schedule. I missed countless weddings, bachelor parties, events. I missed pretty intimate events that I wish I could have been a part of, but there’s no off days.

You can’t call Bill Belichick and say, “Hey, I think I’m going to be gone for 2 days.”

For a bar mitzvah.

Yeah, for a bar mitzvah.

He would say, “Okay,” and someone else would be on the team and I’d be done playing.


So, yeah, I think it is, it’s tough for a professional athlete. I don’t know how baseball guys do it, and they got 160 games in 180 days and they’re on the road all the time.

Football’s a little more 9-to-5-ish. There’s no day off, but it is just Monday through Friday, more or less 9-to-5. Then- It’s more like 7-to-6, but then you have a game on the weekend and…


…back at it. Yeah, so it’s a little more manageable, in my opinion.

Bill Belichick, because we didn’t really talk about that. So, you had a chance to go back and play for New England.


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You just tried out?

Yeah, so did the tryout, literally, you fly out. With COVID, it was a 5-day lead time, which was awful. You just sitting there in a hotel room for 5 days, you quarantine and get tested every day,

But without COVID you fly out and literally, you land, you go to bed, and you wake up at 6 a.m. and you’re on the field sprinting.

They’re full evaluation, like what you see on the combine kind of, but it’s only four players.


Sometimes it’s your other position and you’re just competing with these guys, and so it is. It’s a stressful situation for sure.

No one hears about it, because they try guys out every single day, every team does. There’s four or five guys every day trying out.

What gave you the motivation to want to go back and do that again?

Honestly, unfinished business.


Yeah, I think that. I ran routes for Kevin Hogan, who I alluded to earlier, so he could send his film in for being a quarterback during COVID, because there was no in-person tryouts, so you would just send video.

And I was the receiver in his video, he asked me. And some teams saw it and were like, “Is he ready to play?”

Started getting tryouts. I sent in my own videos, and then I ended up getting picked up by the ‘Niners during COVID season when they were in Glendale, which is a bizarre experience.

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But part of that was, I was in, Christmas and New Year’s in Glendale, Arizona locked in a hotel room, and that was a really, “I made it, and now I’m just sitting in a hotel room.”

Surreal world.

Yeah, exactly. I’m not even in Santa Clara, which is where their headquarters are. I’m in Arizona. I’m not with my family.

And that was the first little bug that got into me. It’s like, “Is this worth it?”


So, 4 weeks later, I’d made it late in the season, 4 weeks later their season’s over, no playoffs. Two coaches tell me they can’t wait to have me back, bring me in, personal meetings.

John Lynch calls me 2 weeks later and is like, “We’ve got to release you. We had someone come off COVID and it was an oversight,” COVID restriction or whatever it was.

And so, they released me.

Back to the drawing board. Do I want to do this? I keep training. I’m training during COVID, running on concrete because I don’t want to run outside in parks. COVID might be there.

Who knows? People are wearing, like, space suits.

Yeah, but it’s definitely not in the middle of the street where my local policeman kicked me off the park and said I could run in the asphalt.


I was like, “Yeah, that’s going to go well, just running routes and sprints on asphalt.”

But why isn’t the COVID here? Why is it only in that green grass area that’s wide open?


Yeah. And so, yeah, I started training and I came back to score touchdowns and help a team win.

Couple teams go by, try out, try out, Patriots bring me in. It’s going really well, but I’m also battling that bug. Away from my family for a month again.

And what year was this now?

This is 2021. This is last season.

So, recently.

Yeah, this is the last season during preseason.

So, I went through them with OTAs, training camp, and then, day before the first preseason game, which is the worst time to get released, is when I got released because they had two safeties pull their hamstring or whatever.

And it was the two guys that was probably going to play in that first game, and they weren’t going to have Dev McCourty, who’s their captain for 12 years, play an entire preseason game.

So, they needed to bring them in. We had six running backs at the time. What I love about Bill is he’s just very honest. He’s very dry, very honest. You’re going to get exactly that. Whether you like it or not, it’s just like, “Here’s the deal.”

And I think at that moment I felt a little relieved that my direction was like, “Do I keep going or am I done?” And right then and there, I decided I’m done.

You’re done.

I want to be home. And when we say ‘retired,’ now I just get to do what I want to do.

When we say ‘retired,’ now I just get to do what I want to do.


Different projects, different ventures, but mostly just being Dad and being a husband and making up for lost time, it feels like.

I’ve never felt fulfilled, whether it be impostor syndrome, that I’ve made up for any lost time. I’ll go to Disneyland all day, 7 a.m. to 9 p.m. I’m like, “That wasn’t enough.” Yeah.

And then the next day I have to send him to school early because I have a meeting an hour early and I’m like, I just throw him around like he’s nothing. it’s that battle.

When you care, it’s that battle.

I love it. The family is everything.

Actually, that’s why I’m here. The family is everything.

I learned that about you right away when we first met in Kentucky, and then watched your social media and stuff. And I was like, “I freaking like this guy.”

That’s cool, man.

Yeah. Not anybody, but there’s so many people that have successful businesses.

So, what differentiates you? And it’s usually- I just say it’s the north star. And there’s a multitude of things that equal the north star, but when you have that, it takes all of them to get there.

Sure, sure. So, thank you. I’m honored.

Of course.

I really am. I didn’t know that. So, thanks for sharing.

Yeah, I came from a childhood without a father.


And so, now I’m compensating and I’m trying to give my kids the life that I never had.


And so, I spend so much time, we do everything. And same with you, I looked on your social media.


I know you’re trying to come off of it, you said, a little bit.

Yeah, I’m just detoxing from it all.

That’s so good.

Only so many hours in the day.

That’s right.

So, right now that’s not time for me.

And I know it’s very lucrative and extremely important nowadays to be alive and have a personality, but I’m not there, and maybe one day.

So, one of the things about social, in most cases it’s the facade, it’s all the positive stuff that’s happening in everybody’s life.

And recently, I decided to be vulnerable on social.


I think it was Facebook, because life was not going well.

We had this huge flood that happened in our house. We have to move out. My wife got into a car accident. My son ended up spraining his ankle.


And I’m just like, “Why just post all the positive stuff? Let me just be vulnerable for a second.”

And you’d believe that had the most engagement ever, people texting me, calling me. And it just felt good just to be vulnerable.

First off, authentic and relatable is number one on any social media platform. If you can do that, everyone’s engaging.


But number two, I hate that it has to be called “vulnerable,” which is the definition today.


Just being human.


You’re just being a regular human, and you experience good things and you experience bad things, and we learn from both, and how we move forward is based on that experience.

You’re just being a regular human, and you experience good things and you experience bad things, and we learn from both

And so, being vulnerable by talking about just a very honest thing that 99 out of 100 people have gone through.

Same thing, yeah. Right now.

Most people have been in a car accident. Most people have had someone they love sprain their ankle and whatever it may be.

But it sucks that that has to be the word, is vulnerable.

That’s right.

Because it’s not normal. It’s only the positive and the highlight reel. I wish there was a platform that it was, like, “This is just real.”

And you can’t, because you get all the people that want to flex and private jets and talking their Bugatti cars and whatever. And that’s not relatable.

It’s not.

That’s a dream that people are just watching and being sad over.

Same thing, even the reality shows everybody tune into, you know what I mean?

They only show the highlights. They’re not showing the real shit that people are going through. You know what I mean?

Of course. That’s what I hate. That’s why I’m honestly off social media as much as I can.

I’m human, but it is, it’s like the only thing on news or any media outlets is like, “How can I get a click? Can I get a click bait?” And the click bait can be great as long as the story represents what I just clicked on.

I think a lot of times they’re only looking for the death or the race.

Oh, they are.

Or the negative, the really grindy negative thing that hurts us at our core.

And then you read through the entire article and you’re like, “Man, it didn’t feel as bad as that headline was.”

That headline.

And I hate how that is. It used to be, you just reported.

And Instagram used to be, you remember on Instagram you used to take a picture of like, I would take a picture here.


Like this, post, done. That’s what I’m doing.


Or I’d take a picture of the sunset. Instagram was filled with sunsets. And it was just like, “No filter. Sunset.” Like, “This is what I’m doing.”

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Now there’s 5 million apps that can edit you to look like Tom Cruise.


Yeah. And so, they spend hours doing that for 100 likes and then they’re sad. And I’m like, “Hey, just let people know.”

And I talk to my wife about this all the time, because she posts a variety of things. The ones she gets the most engagement on bar none are just real family, authentic posts.


Where she’s talking about the not so glamorous side. How she’s walking around at Trader Joe’s and she had poop under her nails because she had just cleaned up our son.


And didn’t realize, you wash your hands but it wasn’t like, “Oh, I’m going to get under my nails and fix this.”


But just very regular things.

And that’s what most people associate with.

Yeah, everyone’s been through that.


I talked about her peeing her pants and here I am talking about it again, but a percentage of people have gone through something similar, whether it be embarrassing or whatnot.

And so, that’s the type of people I like engaging with, again, why I’m here.

Thank you.

So, I had joined a group, it’s called YPO.

Yes. That’s a slight flex, by the way.

If you want to say so.

You can only be in YPO if you’re a big baller.

So, there’s a lot of big ballers in YPO.

Of course.

Some of which are way bigger ballers than I think I’ll ever be.

And so, you go through this vigorous, first of all, you’ve got to try to qualify to get in. And then after you qualify they’ve got to audit you to make sure that you’re legit.

That’s true, yeah.

And then after that, then you’ve got to go through one audition with one person. And if you pass that, then you’ve got to go onto a group audition.


And so, I remember very clearly, I’m on my group audition for YPO and they say, “Hey, Jason, I’m so and so, I’m so and so.” Like six people introduce themselves. “So, tell us a little bit about yourself.”

And I’m like, “Oh, okay, great. Well, Jason Hennessey, I’m an entrepreneur. I started an agency, I’ve got 160 employees, we’re doing this much in revenue,” blah-blah-blah. And I went on for about 7 minutes.

And they’re like, literally this is what they said. “Okay, that’s great. Can you tell us the non-Facebook version of your life?”


And I’m just like-

“I didn’t prepare for that.”

Yeah. And I’m just like, “Whoa.”

I’m like, “So, if you want to know that,” and then I just started getting into the real shit.

Of course.

You know, the real shit at the time was my father was kind of starving himself in Florida and I had to go back and forth, and I didn’t really have a relationship with my dad. And all the real shit that was going on.

And I think it was that, that I’m starting to learn to be more human.

I’m just like, “Wow, if all these really smart, successful people are just being human or vulnerable,” whatever word you want to use, then I guess that’s what we should all be doing.

No doubt. It works even in business. You’re not the only person that has built a great SEO business.

And so, when someone’s choosing, they’re picking between .001% of who’s better, it’s like, “Who do I want to work with?”

That’s right.

“Who do I want to be around all the time?”

And a lot of times you’ll take, if you were less than the other guy but you were way better to be around and more human, they’re going to pick you.

That’s right.

That’s why sales guys are always the chatty, smooth, sometimes douche, but they know how to talk and have a good time. And that’s what people want to be around.

So, what keeps you busy these days? What does a-day-in-the life look like for you today?

Yeah, I have a lot of projects rolling on, typically things I want to do.

I told you I’m heading to Oakland later today to shoot the actual first athlete shots of an athlete-to-athlete coaching app. Athletes showing other athletes how to be great athletes.

And so, we’re filming the 120 most common workouts, warmups, whatever it may be. So that when coaches go on here to fill their workout, if they’re a coach or if an athlete goes on there, they can just click from the repository rather than have to fill it themselves or whatnot.

I think it’s really important to get an athlete’s perspective, but also these athletes are going to be able to monetize their business so well because they’re going to work out no matter what.

So, how do we capture that? How do we build those programs for you? And that’s all moving forward.

I think the really cool aspect is, every single city in America, in the world, has 100 locally famous athletes that went to that high school, went on to college, did great things, and then maybe stopped because they couldn’t go on to the next level, or professionally, it didn’t make sense financially.

And so, how can we change the fact that geographically you are not there?

There are 10,000; 1,000. Whatever the amount of athletes that know about you in that town. You’re in the hall of fame for your high school. They definitely know you.

How can we monetize those athletes? It’s easy if I put Jerry Rice up on TV or any, insert Hall of Famer, they’re going to get athletes to follow their program.

But when you hear somebody you haven’t heard about but he’s from Bozeman, Montana and he was the best linebacker to ever come out of Bozeman, people in Bozeman are going to follow that.

So, that’s ultimately what we’re creating out there.

And then really big into IoT, Web3 space, really learning right now. Iterating probably 25%, but learning, majority, because I don’t think there’s an answer yet. But there’s a wave coming and it’s a massive, massive wave, in my opinion, of all things web3, crypto mining, IoT devices, blockchain.

And so, I just take an hour, two hours a day to learn, whether I listen to people, whether I read things, whether I just dive in on a technology that’s already doing it and just go through their whatever, their website.

And so, being able to create in there and be on the forefront of that is really important.

I think it was the whole dot-com, nobody knew what that was going to entail. Pets.com failed. You definitely know that story because it was just the wrong time.

And so, I want to be on the forefront of this happening.

And so, I have a couple partners that we’re building different projects out in different countries as pilot programs. And then we’ll go from there.

And in other countries, why they’re there, less bureaucracy and a lot easier to get actual infrastructure built, where if I want to build something next to you in LA-

Permits, oh, yeah.

Might take a year to just get permitted before I can even break ground.


Yeah. In other countries you can pay someone that day and it’s built. [laughs]

Sure. Sounds like you’re living the entrepreneurial life at this time.

Yeah, exactly.

And I do a lot of things where I’ve invested in, I’d say zero-to-one startups, whether that be seed, series A, somewhere in there. I find, usually in the e-commerce space because I’d built an e-commerce brand. So, I understand that mentality.

But for me, as you talked about wrestling, there’s fundamentals, you learn about things. And for me it was taking complex information and making them simple. And that applied in sports, but that also applies in business.

And so, when we’re trying to problem solve for things, I can take that situation and be like, “Okay, well, this is the first brick we have to put down to get to that Empire State Building,” or whatever it is.

And so, operations and marketing is where I lean on, but I love wearing multiple hats and helping out in all regards, going from marketing to operations, to, I’m in there with a screwdriver building a mining device, Helium was the one I’m talking about.

And so, I’m having to put the router in, it’s not working. How do I do this? How do we put a fan in there so it doesn’t overheat? Because it’s going to be up high in Latin America during whatever. And so, we’re doing that too.

And that is not, I know how to build, I really know how to build kids’ toys really well. Fastest kids’ toy builder in the world.

But yeah, so I just love learning and being a part of new things. And especially in that industry, whether it be sports tech or all things web3.

I just love learning and being a part of new things.

It sounds like you’re, like you said, learning, which is good. Some stuff will be wildly successful, others won’t, right?

Yeah, exactly. And there’s thousands of projects launched right now. Thousands of NFT projects launched, 1% of them are going to be successful.

So, who’s your “no person”?

Who do you mean? Who tells me no?

Yeah, who tells you no? Is it your wife?


Because there’s so many opportunities in the day, right?

Okay, yeah. So, when you talk about opportunities, I always talk to her and she does do a good job of playing devil’s advocate.


But in retrospect, she knows little-to-nothing about web3. So, it’s hard to talk about the opportunity when-

She might not understand it.

Yeah, she doesn’t quite understand it.

And so, for me, when it comes to e-commerce, there’s a couple things I look at. You look at financials to make sure they’re trending, profitable, whatever, at the stage of business they are.

But the number one thing I learned when I’ve talked to people much smarter than me, the guys I talk to, Jack Mosbacher, Sahil Bloom, who invest in people, what is that founder like? What is their personality like?

Oh yeah, they invest in the people.


Oh, for sure.

And they invest in people, and that’s exactly what I’m doing.

And it’s almost like the number one thing you think about is, “Would this person rather die than let this business fail?” That’s only a little bit of an exaggeration.

And are they crazy enough or simple or stupid enough that when there is a hardship, they don’t abort mission?


I know so many jackasses that own $50 million, $100 million businesses, and it should have failed 20 times along the way, but they were honestly too stupid to realize they’re in debt $2 million,”Tthis is failing, that’s failing.”


They just didn’t understand the ramifications of that, but because they kept going and kept going, something hit.

Mm-hmm. Yeah.

And that works.

But when you have, honestly, those valedictorians, as soon as the time gets tough, they might pull out because they’re in $100,000 debt, 12 months down the road it looks like they’re going to be in $1 million debt, whatever it is.

And they understand that too well, so they bail.


So, you’re looking for a mixture…

Oh, yeah.

…of that, right?

I saw a TED Talk recently, it was a woman, I can’t remember her name.

We’ll include the link on this post, but there’s a woman talking about, is it better to be bold or smart?


And she built up an argument that it’s better to be bold than to be smart.


Because what happens is, when you’re so smart, sometimes you think about all of the what ifs, like what if this goes wrong? What if that goes wrong? What if this?

And you end up starting to talk yourself out of the opportunity. Whereas if you’re bold, you just go.


You just try to make it happen. And it was pretty fascinating. I never thought of it like that.


And for me, I’ve always been the bold person, and my secret to my success is hiring smart people.

You need smart people. Do not discredit that. I’m not looking for a bunch of simple-minded jackasses to invest in.

I’m not looking for a bunch of simple-minded jackasses to invest in.


And then I’ll take another look.

Yes, uh-huh.

You’re right. Smart man. Never be the smartest person in the room.


I don’t ever want to be.

Uh-uh, right? And so, when I said, “Who’s your ‘no’ person?”

So, I’ve got a “no person,” and he’s my COO of my organization, not just my one company, but my whole company, all of my companies. And so, he’s the one, because opportunities present themselves every day, right?

Yeah, of course.

You know what I mean?


And it’s like, “Oh, this is great. This could be the next big thing,” but sometimes they just become either distractions, or just more time away from your family. Right?

Yeah, no doubt. You only have so many hours in a day. I completely agree.

So, but it’s nice to have that “no” person in your life, and he overanalyzes a lot of things, and MIT grad with a Kellogg MBA, he just went on Jeopardy!, won the game, so.

Yeah. So, now that you say that, I have four people that I really lean on, and I take an aggregate of, and honestly, none of them are really “no” people though, is the issue, because they’re not invested with me, typically.

I just take their information and I create a “no,” or I create a “yes,” and I always want it to be “yes,” I always want “yes.”

And so, it’s really helpful for them to break things down in different regards. Some have different backgrounds, but they all have my best interests. That’s all that matters.

Oh, love it.

So, you’re in the car, you got your wife, your two boys, dinner time. Who’s picking where you’re going to eat? Who wins that battle?

Love that you brought this up. We don’t go out to eat.

You don’t go out to eat?



I cook probably 90% of the time. I usually cook a meal for the kids.

I’m not cooking anything special. I’m talking pizza, chicken nuggets, teriyaki chicken bowl, very simple for them, and then I cook our meal.

But the thing I have with my kids is, they have to try our food.


“I’ll make you your own food, but you are going to eat some of my food and some of your mom’s food, because I need you to try it and realize you like this. I’m not going to force you to eat. I made it, that’s what you’re eating.”

I get it. I’m trying to find the happy medium, but they have to eat some off our plate. So, yeah, we don’t eat out, ever.

That’s the best way.

Except for date nights. When we have a date night between us, that’s the number one thing we want to do.

And so, to answer your question, she usually picks, because she normally has a deal with that restaurant, or business, or industry that we’re eating or we’re getting paid.

She’s getting paid to eat, and it’s all compensated. And so…

That works.

…that’s good with me. Yeah.

Yeah. So, next time you guys are in LA on a date night, you want to go to the Magic Castle. Have you ever been there?


Yeah, I’m a member.

Oh, wow.

So, it’s a cool experience, for sure.

Wow. Yeah, I’ve heard of it. That’s like a Soho House type like-


Similar. I mean, I know not the same, same, but in terms of being a member and getting in?



It’s really cool. You go there and nobody has the same exact experience.

You go in, it’s a very exclusive private kind of a club, and you never know who’s going to be there, and you just kind of have a nice dinner, and then you go into different rooms.

Where is that?

It’s up in Hollywood, right off of- behind the Highland area.

All right. So, we’re going to play, it’s not a game, it’s just called “Hennessey Heart-to-Heart,” where I ask questions, and then the first thing that comes to mind, you just say.

Do I answer it quickly, or?



You can give a little thought, but whatever first comes to mind, intuition. Right?

Can’t wait.

What is the best concert you’ve ever attended?

Genesis, because it was the first concert with Phil Collins.

Phil Collins. You got to see him live, huh?

Yeah. I think at the Hollywood Bowl.


I’m pretty sure.


I was young. I didn’t even know what weed smelled like, and there was weed everywhere, for sure.

Uh-huh. He just had his farewell tour. I don’t know if he’ll be playing much more, but man.

So, did the dude, or not the dude, Bruce Springsteen.


He had his farewell tour like 2 years ago.

“The Boss.”

The Boss.

Not the dude.

Yeah. Sorry. “The dude.”

The dude.

The Big Lebowski.

In California, we call him “The dude.”

Yeah. We call him the dude out here, yeah.

In Jersey, “The boss.” Right?

Yeah. Yep. So, yeah. Phil Collins, for sure, Genesis.

That’s cool.

I vividly remember they do the drum scene at every concert, and-

Oh, “In The Air Tonight,” right?

Yeah. Yeah.


So, before he starts, the drummer does a full ordeal, and then they start the song, but yeah.

Who was your role model growing up?

My dad.




For sure. I mean, and he’s become even more of a role model when him and I are very, very different people.

I eat everything, I’m very social, I like talking to people, being on a podcast. My dad would do none of that.

No, huh?

No, and he eats probably less than 12 items.

So, picky, huh?

Yeah. So, not that he’s picky, he just doesn’t-

Creature of habit?

Yeah. He doesn’t want to eat anything else. It’s like a steak and pancake. Very American, simple diet.



And so, your parents live close to you?

Yeah, they live probably 25 minutes from me, like south.

Oh, that’s cool.


And what about your wife’s family?

They live in San Jose. Yeah. So, by Stanford.

I got it. What thought or practice gets you through the day?

Working out.

My wife could tell you easily, by how I’m acting around 1 to 2 p.m. if I’ve worked out that day.

Oh wow.

1000%. And I know too, I need it for my brain to turn on.

When we talk about coffee, I still chug coffee, but I need a workout to have clarity and to emotionally be stable for that day.

Not that I’m unstable, but I’m a little snippier. It’s kind of like you’re hangry is how I would describe it, but I’m just hangry for the rest of the day, until I’ve worked out.

Side note, we were at Kentucky at a dinner, and they did a push-up contest, and there’s fit people there, right? And-

One of the trucker guys was mass- I thought he was definitely going to win. He was like a bodybuilder.

And he gets up there, and it kind of starts out at like 12 people, and 6 people, and 4, and I’m like, “My money is on Tyler, for sure,” and sure enough, you were not going to give up, huh?

No. Yeah, I was going to die before I was going to lose.

I thought it was going to be a bunch of lawyers up there, but it was kind of like the people who were invited, there were a couple lawyers up there, but yeah, there was like an Ironman up there.

Yeah, there really was.

I thought that guy might win.


Because he’s 145 pounds.

Exactly. Seriously, that’s like all mindset, right?

For sure.

Like when you’re in there, it’s just like sometimes your mind is controlling your body, right?


Even though your body’s about to give up, but you’re like “Uh-uh, I’m not losing.”

No. I mean, all of those crazy psychos that you can follow, the David Goggins of the world, they’ll tell you every time that we quit, 60% or whatever the percentage is, before we’re done.

You’re supposed to-


Yeah, before you can. Yeah.

Everything in your body’s telling you to quit, “It sucks, it’s cold, it hurts, I’m tired,” but you’re not done.

Just like when you’re starving because you didn’t eat for a day, you can actually live for 10 more days with no food.


It’s not that big a deal.

Mm-hmm. So, true.

It pisses me off, I’m hungry though-

Speaking of food, what’s a favorite food that you could never live without?

That’s a good question. Favorite food, right off the bat, was sushi.

Sushi? Okay.

Yeah. But live without? If I had to be very particular, peanut butter.

Ooh. Okay.

I make my own peanut butter on the regular.

We joke around that if my kids were allergic to peanut butter, they might just go up for adoption.

It would be a tough choice. Yeah, it would be a tough choice.

That’s a quote.


What’s the most important lesson to teach a child?

We tell our kids that you never give up.

We tell our kids that you never give up.

Never give up.

Yep, and I think for a child, it’s just so basic that you just never give up, and that goes with a lot of things.

We have a lot of multidimensional sayings like, “You always clean up your mess.”

Right now when you’re 4 and 5, it’s like an actual toy mess, but when you’re 10, 15, 20 years old, then you have life messes, and you always need to clean those up.

So, I hope they last forever. So, always clean up your mess, and never give up.

Got it. Have you ever done something so spontaneous that you surprised yourself?

No. Maybe two-fold, because I think about everything I’m going to do, right then and there. Yeah.

And so, spontaneous? No.

It’s like I made the decision, even if it was a 5-minute decision, for 5 minutes in my brain, it was full…

Deep thought.

…1,000 person-

Conversation up there.

Yeah. Yeah. I’m trying to think of anything.

The one thing I really want to do is, next time we get pregnant, is not find out the gender, because there’s not a lot of surprises left in life as an adult, like you’ve experienced 99% of what the world has to offer.

And so, being surprised by something is like, savor those things.

Yeah. That’s true. That’s a good way to look at that.

So, having a gender reveal as the baby, is one of those moments in my book. It’s not in my wife’s. She wants to know, so.

I live a completely spontaneous life. My wife and I got married after knowing each other for a month and a half.


It was just April Fool’s Day, I came home, said, “Let’s go get married,” and we did. And so, 23 years later…

I love that.

…3 kids later.

One time I was driving down the road, and I was doing sports betting at the time, and I had, I don’t know, like $15,000 in cash on me at the time.

And so, driving down the road, and there’s this sign that says “Palm Trees For Sale.” And so, I pulled over, I’m like, “This big palm tree would look amazing in my front yard,” and I bought like a $8,000 palm tree, just because, right?

So, yeah, I just kind of, sometimes I guess I just live this spontaneous lifestyle.

I envy that. I think I’m institutionalized because of sports, that this leads to that, that leads to this.

That’s true.

I talked to my therapist about it. So, I’m working on it. [laughs]

What makes you angry?

When people don’t take advantage of what life has to offer, and that’s another way to say like weak, dumb people, because most of us were given two feet, two ears, two eyes, two hands, very similar opportunities.

Yes, there are people that were ahead, whether it be because of their parents or whatnot, but I know thousands of people that were successful in a terrible upbringing, and I know thousands of jackass kids that came from wealth, and they’re not.

And so, I hate when people just do not take advantage of what’s right in front of them, big things like that, but also small things like not turning right on a red light, and just, what are we doing? Yeah. What are you waiting for?

There’s a saying, right? That at the end, whatever you believe in spiritually, at the end of your journey, when you transition, there’s a saying that you’re probably going to meet the individual that you were destined to become.

Love that.

And you want to try to be as close as you can to that individual.



I love that.

Live life to the fullest and take risks, right?

Yeah. Be bold.

Mm-hmm. What helps you decompress if you haven’t worked out?

Working out helps me decompress, but playing with my kids, I put digital stuff away, and it’s kind of like, live in their world, because I mean, I’m not too old.

My wife says my memory is too good for these things, because I remember my kindergarten teachers, people in this class, first and last names. I can remember them all, but I can vividly talk to you about a lot of them.

I remember playing with bugs and dinosaurs, and creating these little arenas where I would harvest them all in, and so, I like to join into their world.

And it’s not always easy. You’re tired, they have attitude, whatever the friction is, but I feel so good about being with them and being in character, and being that action figure he wants me to be.

That’s cool.

I love that.

What’s your favorite movie?

For entertainment, either Billy Madison or Happy Gilmore.

Oh yeah, huh?

Yeah. Oh, Adam Sandler all day. Number one.

My wife is being an actress, or trying to fulfill that dream of hers, she wants to be #StrictlySandler, and it’s just all Adam Sandler movies.


Entertaining, Happy Gilmore, Billy Madison, maybe the best movie.

I also like Guardians of the Galaxy for overall entertainment. It’s funny, action. I’m a nerd at heart. So, I don’t know.

A Few Good Men sticks out. Shout out to your law SEO guys who’ve all seen that movie a million times. It cycles, right? There’s a lot of movies I could talk about, but I just saw A Few Good Men, a year ago. It sticks out.

If you had to live somewhere other than California, where would it be?

It would be somewhere in the forest or jungle. Very tropical, like Costa Rica, or like a Montana. I know those are two opposites, but I fell in love with Jackson Hole.

Probably be in the forest like that, mountains, forest.

What’s your go-to karaoke song?

So, actually, my favorite one is “The Real Slim Shady” by Eminem. I know the words from my 10-year-old self, or whatever it was.

So, it’s just passion, and everybody loves it, it’s a party favor, and I’ll get into it.




You would’ve seen it in Kentucky, but I had no voice for the first time in my life.

No voice. Yeah.

And when I say, no voice, people couldn’t hear me whispering in their ear. Yeah.

No, it was real bad. I remember.

Yeah. Never experienced anything like it.

Do you have any lame dad jokes that you use on a regular basis?

Lame dad jokes? I think the best dad jokes come naturally…

They just do.

…when you can just take a situation, someone says something and you’re like, “Perfect.”

No, I don’t, off the top of my head.

There’s an Instagram handle called “Dad Jokes” or something, and every day, there’s just amazing dad jokes.

Oh, the two guys talking?

So, that’s one. I’ve seen that one.

Yeah, you know what I’m talking about, they’re talking to each other?

This is just, it’s just a joke that they place every single day…

Got it.

…and some of them are just like, dads appreciate it.

Oh, 1000%. Yeah.


There is a guy on there who always talks about like, “Showed my neighbor how to cut his steak in front of the rest of the neighborhood,” like on the power, or whatever.

Just yeah, little things like that.

What motivates you to be the best version of yourself?

So, now my kids, like my family.

I try to be better for them every single day, and sometimes that’s a lot for them, because it’s a lot for me, and I know I’m not easy to be around all the time, just because I’m constantly putting the pressure on, whether it be putting on you, whether I be putting the pressure on myself, but you can feel that being around me.

So, my friends, my family have both told me that.

Got it.

And of all the things that you’ve done in your life, from having children, going to Stanford, playing professional football and baseball, what’s the one thing that you think your parents are most proud of you for?

For the dad I’ve become, for just the man I am now, and I only know that, I know that because I think it, but I know it because they told me, and just the life I’ve cultivated, which is a very normal, regular life.

It’s just the love and affection, and inclusion of everybody that they really appreciate.

And then one last question, off the script here, but what was it like kind of playing ball with, like, Tom Brady? What was that like?

Yeah. Tom and Bill are the best fundamental leaders in the world for very different reasons.

Bill knows how to take anybody’s strength in the room and use it, and formulate it into the game plan.

So, if you’re a pass rusher, like you’re going to pass rush. He’s not going to put you in pass coverage.

If you’re a run stopper, or if you’re a man coverage guy, those are the situations you’re going to be in, and it doesn’t need to be a surprise, because if they’re really good at it, then it doesn’t matter.

And then Tom, in a similar regard, he just, for the last 20 years, there’s people that are better athletically than he was, and better, in many regards of different things, but he just out-behaves everyone.

And what I mean by that is number one, he’s leading you by example, like meeting starts at 8 a.m. It’s 7:59, and he’s jogging down the hall, so he’s not one second late.

I’ve been in plenty of locker rooms that the star players show up 10 minutes late, and it’s no big deal, and once that happens, it’s like the next star is kind of like, “Okay, I can show up a couple minutes late. I’m almost as good.” Next star is a couple minutes late.

No, there’s no games played in there, and Tom leads by example. He’s a great human, he treats everyone really well. You would’ve never known who’s a rookie, who’s a ten year vet.

And so, that’s the reason both of them are successful.

Is he the G.O.A.T.?

Easily the G.O.A.T.


I mean, there’s no question about it, and I’m a big advocate of, would he have survived in the game back then? Would other players have survived in the game back then?

But also, there’s a lot of players that wouldn’t have survived in the game today. It goes both ways. It was a very different game.

Those 260-pound dudes running their face through your face. They would just get run around, like these Tyreek Hills, and these little running backs of the world now would just run around them, and they wouldn’t be able to touch them.

So, there’s a very dynamic and you can talk about the Joe Montanas, which I think is the next G.O.A.T., when you talk about those things, but I mean, the guy’s been to like 20% of the Super Bowls that have ever happened or something. Some ridiculous number.

He’s won like 8% of them, and he’s been to like 20% of them or whatever the number is. How do you not say that guy’s the greatest? How do you not say that he’s won for like 20 years?

I remember I was in my rookie year, and I was listening to a song and I was like, “This was my high school pump up song. I love this song.”

We turn it up, and Tom comes over while we’re working out, and he heard that and he was like, “This was like my fourth year in the league.”

When this song came out?

Yeah. Tom is in the NFL right now, longer than the rookies have been alive, which is just nuts to think about.

And still plays at such a high level.

Still plays at such a high level. Yeah.

That’s amazing. Well, Tyler, man, it means so much that’d…

Of course.

…you come down here on the show, being time away from your family, and I look forward to meeting your wife and kids, and getting together offline too, man.

I can’t wait. I really appreciate it, and anytime.

Awesome. Thank you.

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