Sept. 30, 2020

Season 1 Finale — The Game Plan: Greatest Hits

Season 1 Finale — The Game Plan: Greatest Hits

Be sure to tune into the final episode of Season 1 of "The Game Plan" as Jay and Tim take a look back and highlight some of their favorite moments from the past year including audio clips from Super Bowl Champions, Olympic Gold Medalists, All-NBA team honorees and Hall of Famers.

Listeners new and old will enjoy listening to these highlights, as well as the color commentary of The Game Plan hosts Jay Kapoor and Tim Katt. We explore why these moments really stood out in a season full of insight, authenticity, and emotion.

Featured guests include:

  • Hall of Fame inductee, Olympic Gold Medalist and Sports Innovation Lab Co-Founder Angela Ruggiero
  • USWNT member, FIFA Women's World Cup Champion, and Co-Founder of Re-Inc Meghan Klingenberg
  • Former All-NBA Shooting Guard, Team USA Olympic Gold Medalist, and Founder of Twenty-Two Ventures Michael Redd
  • 3x Super Bowl Champion, media personality, and Co-founder of "Mark's All-Pros" Mark “Stink” Schlereth
  • Super Bowl Champion and founder of The Wine MVP Will Blackmon
  • Former Major League Baseball player and Co-founder of Players for the Planet Chris Dickerson

Jay and Tim also wrap the episode with key takeaways from Season 1 of The Game Plan including:

✍🏿 Athletes-Investor strategy

🔌 The power of humility and authenticity

🗣 Dispelling the "Broke Athlete" narrative

🤸🏼‍♀️ The exciting future for women's sports

Special thanks to Will Richardson and Meghan Roxas for all of their help in producing and promoting Season 1 of The Game Plan.

Be sure to follow co-hosts Jay Kapoor (@JayKapoorNYC) and Tim Katt (@Tim_Katt) for all things sports, media, tech, and venture capital.

Follow The Game Plan on Twitter (@thegameplanshow) and Instagram (@gameplanshow) for show news and updates, to recommend guests, and for bonus content!


*Please excuse any and all typos, errors and mistakes in the following transcript as we use an automated service to generate this text*

Well, Jay, it's hard to believe we've done 34 episodes now in the game plan. And I'm really excited about this one. We're wrapping up season one with a little bit of a greatest hits episode.

It's kind of crazy to think Tim. There were so many times where we didn't know we were going to make it to 35, but here we are. We've got some big plans for season two, but I think before we get into that, why don't we do our greatest hits are our favorite moments from season one. Then we can wrap up with a couple of takeaways that we've had now doing the show for close to six months and maybe some reflections for what we'd like to see going forward.

How's that sound?

Yeah. So for listeners new or old, I think you'll really appreciate this. We cherry pick some of our favorite moments. I'm going to kick things off. Jay. I'm not sure if you're expecting this, but a little hidden gem we had the season was a reference to our current president, Donald Trump. And it was, it was not political.

It was not a political reference, uh, believe it or not, but I'm talking about episode 18, where we were speaking with us hockey legend and four time Olympic gold medalist, Angela Ruggiero. And she talks about the time. She had an opportunity to potentially work for our current president. Let's roll the tape.

 And I have to ask is we can cut this if you want, but, , you wouldn't have told yourself to take the job offer from Trump after the apprentice in 2006. 

No, you know, what's crazy with that. My, even my father told me to take that job. Everyone was like, you're crazy not to work for Trump. He wanted me to work with his kids downtown New York. Is before he's running for president. , and so, and I actually went to high school with Ivanka. So I already knew her from, from my Choate Rosemary hall, my or prep school.

So I had all, you know, all the cards are laid out. I'd be making a boatload of money, blah, blah, blah. And, , and I looked at all of his properties. I said, well, maybe the golf, maybe I could run him one of his golf courses or he had a foundation. I'm sure you've heard about the foundation, how that wasn't, um, invested in properly, but.

But I had to follow like my heart and by following my heart, I'm super proud of this. I went back to my fourth Olympics. I got elected on the IOC. It opened up a million different doors. I mean, I was at the Prince of Monaco's wedding. Who's an IOC member. Like I've done like. Insane things. I was, you know, I go to Buckingham palace and meet the queen and, um, you know, I've been able to go back to business school.

And I just, I look back at that one decision. Um, when the world was telling me go work for this guy named Donald Trump, because he's got a flashy name, he's going to pay a lot of money. And I was like, no, I need to play hockey. One more Olympics. , anyway, so follow your heart is my advice in, and don't follow the money.

The money will come though. Believe me.


Wow. I can't believe you came out of the gate swinging with that one too. Oh my God. Yeah, that was, that was a crazy story. And it just kind of makes me feel like, you know, the, the lesson there is. As an entrepreneur, you have to March to the beat of your own drum. You have to Zig while everybody else has eggs or vice versa.

And with Angela, she had a very clear. Idea of what she wanted to do. And, you know, again, you can always tell that revisionist history of, Oh, this thing might've happened, if that thing happened, but it seems like she's pretty happy. She went back. She's pretty happy that she got to play in the Olympics one more time and all the great things that have happened to her since started with her, turning down a job, offer that everybody told her she should take.

I just think it's funny because a lot of the things she mentioned that she ended up doing as part of her role with the IOC, she may have low key, also been able to do had she worked for Trump and had been part of this administration or something, but. I think she's happy with the path that she took. So let's go on to our next clip.

Jay, what do you got for me?

All right. So. I don't know if you're expecting this one, but this was one from one of our earliest episodes with broadcast or podcast or an all around personality, Mark Erath and Mark told a phenomenal story that I don't think he's told anywhere

I already know where you're

going with this. 

I want to make sure that our listeners hear this one.

So, so ultimately you recovered.


And was that, that was completely on your own,


or does it, you know, where their advancements from the doctors you worked with or,

No, it was just over time. You know, now they do a lot of blood transfusions for it and you know, they treat you, you would like a steroidal, you know, kind of concoction. And, but then they didn't, and I just recovered over time. But, you know, I went back to training camp in 1994 for the Redskins.

And I still had, you know, several toes that were still numb. Um, I hadn't, you know, it had dissipated creep down, but I remember weighing in, and I was . I was two 68. And so I was like, man, I can't weigh in at two 68. I mean, they're just going to go, they're going to go ballistic.

So I weighed in, I got a 10 pound weight, and, um, I, you know, put it, put it in my pants, they, my shorts. So it was just in my jockstrap that, you know, look at little 10 pound plate and weight in. So it was two 78 and I was like, yeah, I haven't gained all my weight back, but I'm on my way back, you know?

my God.


Like by late November, December, I started playing really well again, and I started feeling better again, and I started gaining my strength back and I gained, Oh no. My way back. I was back legitimately in the two eighties, you know, high two eighties. And so, , at that point I started playing really well, which was fortunate because it was right before free agency.

And then, and then, um, you know, it gave me an opportunity to go into free agency in, in 95. And, . Although I did, I hit free agency. I failed the physical in Chicago. I filled a physical in Atlanta. I felt the physical in Indianapolis, but, , Mike Shanahan, and I owe him a debt of gratitude. He basically just said, Hey, this guy's gonna pass regardless of what it shows up on his physical.

So, , so that's how I ended up with the Broncos, who I just failed physicals all over the place. Yeah.  


Yeah. So at first it was very serious right here. He is talking about a disease that he had, how it sidetracked his whole career. And then out of nowhere, he pulls this crazy story. I think looking back at it, you know, it's nice that he can have a laugh about it, but pretty serious at the time.

I know this show is so much about what guests are doing off the court. But I think in this case, why this story sticks out to me is like just the perseverance that he had and the perseverance that you have to have as an athlete. And we hear it from a lot of our guests where they're just like, Yeah, you just try to get better every day.

You just try to pick up and learn and be coachable and sort of all of those things that transfer over to being a really good entrepreneur, being a really good personality, which he is, you know, and, and podcasting and media, , Mark just sort of had that mentality of like, yeah, I'm going to make my way back.

I'm going to get better. and he, he was ready to do whatever it took to get there up to and including hiding weights inside of his jockstrap.

yeah, certainly a whatever it takes kind of story. So Well, switching gears a bit, I don't think we could talk about this first season of the game plan without acknowledging all of the things that are going on in the world, , between a global pandemic, the social justice movement and something that's very real that I think. People forgotten until recently because of what's going on with the California wildfires, which is climate change.

And we rock Chris Dickerson, former major league baseball player, and now CEO of players for the planet on this was right after the NBA players decided to strike during the playoffs. The Buck's team had stepped out of the game. Then as a result, there was a domino effect where other teams stepped out as well.

And. There's no doubt. This was our most raw and deep interview. So let's roll the tape.

 I mean, I grew up in Southern California and I mean, our state is on fire again, you know, it's just, it's crazy. This, the state is on fire. Yeah. Again, you know, the snow pack gets worse and worse every year. It's more unpredictable. I've been, I've been sick. I've seen it. Friends get really sick in the ocean from, from.

Just the irresponsibility of the runoff in local beach side communities and developments. I been on field trips to the mountains and I understand what we're doing to these natural habitats. Like we're still shooting mountain lions that we've been tracking for 20 years and they're just keep falling off because we just feel like this need that they have no right to this natural ecosystem.

That is, that is earth. And when, whenever we feel threatened by. What is naturally supposed to do what they're supposed to do. We basically shoot them down. 

It's really difficult, you know? It's really tough. I feel like I all in it's honestly, to the point where you remember the matrix, when I forget the name of the character, but when he was basically trying to get out of the matrix and he's sitting there and he's like, you know, ignorance is bliss and he takes a sip of his wine.

It's just like, sometimes you're just better off not knowing. And the more that I've dialed in, in the more research I've done, like reading through the climate report was like one of the most depressing things I've ever done going to world oceans week and sitting through a two hour documentary on what's happening to the albatross and how just basically being killed off by plastic and then hearing the world leaders in these agricultural set sectors.

Talk about where, how, what the state of the oceans and what the state of their fishing markets looks like. Seeing that the tension and the despair and the body language and people at the UN, and this isn't like a backyard, you know, neighborhood, you know, environmental watch group. These are, these are the brightest minds in the world and they're cringing in their seats.

So it's, so it's difficult to hold your shit together when. No, you have, you know, you have kids and your friends have kids and, you know, you know, like the world is going to be completely different. They're not going to have what we have. That's the most disheartening part, just not only just, you know, having a biracial daughter, not understanding just that part of it, but understanding that a lot of these animals that you love, that you see on TV, aren't going to be.

Fucking tough conversations to have with little kids. You should shouldn't. We shouldn't have to have to have to have them. 


You know, that's why I started player for the planet.

You had said, you know, the only thing you can say there is. It's it's just amazing to see and hear how much Chris cares and that this isn't some side project or hobby, or, you know, you know, sometimes I think when fleets get involved in causes, people think that it's a PR thing. And like, this is his thing, man.

He is in it. He cares about it. He champions it. And just how much he understands about the damage that has been done, how. Environmental justice and social justice are intertwined and how it affects poor communities and minority communities. And it weighs on him and that he was able to just share that so openly with us and kind of trust us with that story.

Um, yeah, I know it was a recent episode, but, but it definitely is one that, that still rings out in my mind.

yeah, certainly worth going back to, for any of our listeners who are still catching up on the game plan. Chris is such a great example of an athlete using their platform. And actually bringing together the platform of other, maybe more well known athletes to do something incredible, which is what he's done with players for the planet.

So really thankful Chris joined us and especially thankful for how open he was willing to be with us.

Well, Tim, in the lens of those kinds of conversations, you know, one of the conversations that I think we don't have enough on this show. And I think you and I have had sort of talked about how we get to have it a little bit more is around the idea that a lot of our guests are black. A lot of our guests come from.

Experiences that they have faced in their lives that you and I just don't know. And how do we get to have those openly? And one of our guests that I think challenged us to think in that lens was Michael Redd, who is a former NBA, all star and gold medalist. And now with the work that he's doing at 22 ventures, challenged us.

So there has been a lot of conversation amongst the tech and venture community over the last couple of weeks on what that industry could be doing to better empower. Black and Brown founders, minority founders in the ecosystem. You know, we hear what you're doing, we love what you're doing, but how can the rest of the industry catch up to that and what can they do to help bridge that gap as well?

Care. Care, Care enough to hire care enough to forfeit power and authority care enough to invest. . Racism is not a nascent thing to our culture. It's been around for 450 years. You know, there's been this notion, , of integration. Right integration, like integration has been like the aim and goal of America forever. Well, it's not an aim and it's not a goal. It's a fact, it's a fact that has been received, refused to be received and embraced. So we've got to transition it from being a goal and an aim to actually being awakened to that. It's a fact, we've gotta be able to empower minorities and we've gotta be able to have minorities at a powerful position because the lens begins to be widened and it becomes expanded.

And then you'll see change. I was around, I was 12 years old when Rodney King was beaten was around. It's been 30 years. It's the same cycle. Right? And when you look at it from an economic standpoint, again, I mentioned earlier, whoever, whoever has the institutional power controls the narrative and there's over 2000 billionaires in the world today, there's only four African American billionaires, David Stewart, Robert Smith, this to equities, Oprah Winfrey, Michael Jordan. Until that gap shrinks. We're going to continue to see this cycle happen because with diversity at the top, there's more of an empathy in our distressed neighborhoods, on education, on access and opportunity. So that's my soap box, but I believe that's where we can start. 

yeah. Hearing Michael's voice again, and the things he had to say, you can just feel it. You can feel how much. This isn't just a one off new thing for him. It's something he's dealt with his whole life. And it's something that he wants to make monumental generational change in a way that is so much bigger than his basketball career.

And I really admire that. I admire his aspiration. I admire his focus and I admire his authenticity in his effort.

I think one of the best things about the show for me personally, is. Just the insightfulness and reflectiveness that we hear from our guests. And, you know, when you grow up and you know, you're a Milwaukee guy, you were watching Michael red and, and you sort of see him as his hero on the court. And to hear him talk this way, I mean, I'll put it like that.

He's, he's a hero for me now with the work that he is doing and like, to just be inspired in that way you realize like athlete or no, this is somebody that. Has a mission has, has a cause. And, um, you know, he's, he's going to go out and accomplish it and we're excited to support him as he does that.

Yeah. And I'm thankful. That we're able to have these types of conversations. And we talked about it in some of these episodes, how they're not easy conversations for us to have admittedly, we're just trying to learn. So we've asked that our listeners be patient with us and learn with us, and we just want to build the game plan in a way that can present those every, every kind of issue and really help.

Us learn, help our audience learn. And that's really, really our goal, but on a lighter note into your point about, you know, talking to some of our, maybe childhood heroes, so to speak as a lifelong Packers fan and a big advocate for wine, or at least enjoy drinking wine. Uh, I had a lot of in our conversation with Superbowl champion and founder of the wine and VP will Blackman.

He tells us about an interesting time where he first started getting into wine and how that played out.

so every away game. it didn't matter. The magnitude of the game, all the defensive backs, we will all go out to dinner and Charles will pick the restaurants and the texts like, Hey, meet everybody.

Meet here, leave your suits on. We're going to go to a really nice place. So every weekend we did. And, we played Minnesota, I think there was 2008, and we, we, you know, there are usual fine dining, good wine. And then we just kept having more wine and cause I guess we had a, it was a short trip, so into Minnesota from Wisconsin.

So we got there early enough time before we had to go back for a meeting. So we, we had so much wine that night. It was just crazy. And then it got to the point where, I remember when we were almost done, we heard music and the waitress like, yeah, there's this, actually there's a huge lounge upstairs.  . We were like, we looked at our watches. We were like, all right, we still got like another half hour. So we all, the defensive backs went upstairs and when it was me, Charles Woodson, Jamal Williams, Nick Collins, Patrick Lee, I think that was, that was pretty much it.

We all went upstairs and we got more wine, and then we saw a Troy Aikman. And, and Joe Buck, they were there too, and they came by and gave him a glass. And so, where are they living? Like we have nothing going on tonight or tomorrow. So then I remember we get back to the, to our hotel, and I was like, man, I looked in the mirror and I was just glossy eyed.

And it was like, damn, dude. And we have a noon. I think it was a, Well, I think it was, I think it was, it was a primetime game. And I was like, damn, dude, like I don't know what I'm gonna do tomorrow. So get up the next day and I feel like absolute trash and I, I'm talking to, I'm talking to Charles, talking to all the Charles is fine, but your mind or he wasn't feeling well and Nick Collins and so we get into the game, you know, drilling kicks down, warmed up, hydrate. Then immediately Charles Woodson gets a pit,


know, and we're like, no, but we're like, that's Charles of Queensland of course. And you get to pick like this. I mean, there was nothing new. He was taking stuff off every week, and then I think a quarter later Tamana gets a pic and I was like, Aw, dude. Like, like that was a nice job.

You know? He had a lot of momentum that season. I think he got a contract the next year, and then third quarter, Nick Collins had a pick six.

No way.

And I'm like, yo, I'm like, what is going on right now?

seriously. What was in that line?

no, but I'm like, damn, that's

No, it

all through so far, everybody did something, you know? And then I'm like, well, shoot, like I got to do something now, you know?

And, and I go back and I receive a punt and I take it to the house too. So then we're on the sideline, like losing the whole mind, like, yo, we got to go every night. 

so I said it gets better. I remember that game.  

Wow, man. What a story? And to hear it, like, I mean, not just, well, but obviously Charles Woodson is. Now gotten into doing his own wines and hopefully we'll have him on the show sometime. But to also hear that, you know, he's a guest that took a passion of his and turn it into a business with, with the wine MVP.

And he's kind of become the NFL wine guy where he's helping other players out and making sure like when Saquon needs something in his cellar, like he's helping them get stocked. The really cool thing is like demystifying. The idea of, Hey, if you're an athlete that wants to be a. A startup founder. You want to share your passion?

Like it doesn't have to be this thing. Oh, you have to understand social apps and building a technology. Like, no, you, you have a passion, you have a platform and you can turn that into a business to share with people, even after you're done playing football. That was the coolest takeaway. I mean, I love the parts where he was talking about what he looked at in a wine and how he's getting his w set.

And, you know, he's learning how to be a som, but like, that was just a really, really cool story.

Yeah. And we'll talk more about the humility. A lot of our guests have had to have in getting into these different interests. We'll talk about that and kind of some of our overall season takeaways, but you can tell what will even now he doesn't pretend to be the smartest wine person in the world or. You know, I have this like deep understanding that is, is unachievable by anyone else.

It's actually quite the opposite. And I think that's why he's having so much success in what he's doing in the wine business. Although I will say for the record that the Packers actually lost that game where the defense dominated and he had a pot writer. And I think that was pretty funny when we went back and he mentioned that.

That is, that is a rough one. Ma'am well, anyway, so we'll close our best of, with one of my favorite stories from Megan Klinenberg world champion and co founder of rethink 

Wow, I love that. So it sounds like defining what re stands for and understanding who you were making this for came naturally, but where did you even begin as it related to building out the supply chain, including everything from product design. To material sourcing, to manufacturing and fulfillment.

Oh man, we, we really had some, interesting roadblocks at the beginning as every startup does, right? Like, it's just hard. It's just so hard when you're new and you're trying to figure it out and you're leaning on it. People that you hope you can trust, but you don't know if you can trust. So it's, it's, I mean, we did not do a perfect job of it at the beginning, and we're certainly not doing a perfect job of it right now.

We want to keep getting better and make better clothes, that fit better and feel better and, and are better for the world. So it was really difficult at first. I don't think we really hit the Mark that we wanted to. I think we fell short with our, with our. first line. And that's really hard to say because we're really proud of it.

We're really proud of what we did and a really short amount of time, but we also knew that, Hey, if this was soccer, that wouldn't be good enough. And for us, we have this bar that's not just here like, good enough is not good enough for us. Right? Our bars up here, we want to be excellent. And so that means, you know.

Always talking about the fit, always talking about things that went wrong with the thing, with the previous line. How can we make that better? How can we design it better? What materials can we use better? Was fulfillment good enough? Was customer service good enough? And we'll go through every aspect of the customer experience, whether that is, you know, the website all the way down to returns.

And, we'll just be like, Hey. We heard from people online that this wasn't good enough, and even if it's maybe just one or two comments, we do our best to try and fix it. 

How cool is it that here we have a world cup champion, one of the most recognizable female athletes in the world, and she's sharing her story about doubt about the grind and also just being so open and honest about it. I mean, she could have just as easily. Said no everything's been perfect from the start.

Like we always had it figured out. No problem. We, we went into this with an idea and we executed it perfectly, but just sort of willingness to share. I mean, it speaks to what a genuine person Meghan is and why she's one of my favorite all time guests that we've had on the show. But it's also the reason I think we do the game plan.

Yeah, it reminds me. And I think hopefully reminds us as investors that like a startup is a journey, not a destination. And so in that you kind of have to realize that the more honest you are with yourself about like, Hey, when things aren't going well, okay. Let's talk it like you don't, you don't come in.

To building a startup with every problem solved. That's not what this is, and that's not what building a businesses for Megan. It was like, I had this idea. I know that I want to make it a reality. That's enough. And now, okay. I have one in front of me. How do I get the rights I'm going to solve that problem?

Oh, I need to get, you know, my teammates on board. Great. I need to figure out what roles my team mates are going to have. I'll figure that out too. And so with her and her, co-founders all of whom are world champions, all of whom have these amazing platforms for them to come together and say, we believe in this.

We believe that there's a company unlike any other that we can build. And that's enough. I think that's like the cool thing. That's like the reminders, like, yeah, you don't have to have everything figured out on day one, as long as you have the passion to keep going and figure it out sometime soon.

Yeah, and I actually think that's a good segue into this next segment. It was a lot of fun. Looking back those clips, I'd recommend anyone listening to this. Definitely go back and check out some of those full episodes. If you enjoyed any of the clips we just highlighted. But one thing we don't get to talk about enough on the game plan is our role as investors.

And how often we interact with entrepreneurs. And that's really why we wanted to start. The game plan was to shine a light on athletes, both as investors and entrepreneurs. So in that vein, I thought it would be a fun segment to get into just kind of our takeaways from the season, the things that we maybe didn't see coming, but we kept hearing again and again, from the different guests we had or specific highlights of.

The advice that our guests had, that we really want to make sure we kind of reiterate with our own perspective.

Yeah, why don't we start with some of the conversations that we had about the investment approach that these athletes took. So for me, that was, I think, An interesting learning where, you know, you're talking to guys that have made millions of dollars in their careers and they're very public.

And so they have a lot of access to really interesting deals, but whether it was one of our first guests, Derek Morgan, or our most recent guests, Matthew Dellavedova, it was interesting to hear very similar advice, which was start with smaller checks. What did you think about that?

It's funny because I, in some ways had a similar experience as I started to enter into investing what you want early on when you're doing direct investing is experience. Obviously you want to. Make an incredible return. Like that's why you should, that's the only reason you should invest, right. Just to be clear.

However, these athletes are in some ways pursuing it as just something they're interested in. And so if that's the objective for them or secondary objective beyond making a return, the more you can just get reps early on and get exposure. And understand how the deal process works, the conversations you need to have with the founder, the things you need to be asking for what term sheets look like, how the process of actually like administrative things like wiring the money and then tracking it and taxes and accounting.

Like we've talked about this stuff before, but you can gain all of that experience with smaller checks and the benefit of that experience after having done that for two or three or four years. Is now you can go out and make a bigger bet, have a more clearly defined strategy of, okay, this is exactly what I want to get into.

Or ah, now I see that it really does take seven to 10 years for these companies to materialize. I didn't realize that I thought this was a for sure thing, like overnight winter. So. I loved hearing that I wish, you know, I could have told these athletes that earlier, but hopefully through this show, we'll have some athletes listening that maybe pick up on that advice.

Yeah. It's one of those things about investing that I think every young venture capitalist learns, which is you cannot escape the power law. That's just how it works. 65% of companies don't return. The initial capital 25 will return between one and five X. And then it's the ones beyond that. So what are we left that like less than 10% that you're actually making most of your return on?

So yeah, the more. That's you get to place. The more you get to spread the risk around the more the portfolio theory works in your favor.

While we're on the topic of athlete as investors and given all the conversations we've had. What's your kind of takeaway should the athletes and we're generalizing so we can pull specific examples if we want, but is this something athletes should continue to pursue directly or should they look to gain exposure?

Let's say through a fund, either as an LP or maybe some. Deeper more strategic type partnerships.

So I think it's worthwhile for athletes to consider venture capital as part of their portfolio theory. Right? So maybe they're in stocks and bonds and they have a manager that manages that they are in real estate. They have a manager that probably takes care of that. Like that's the stuff that. Some folks are really interested in Pat Cunnington is really interested in, so he's managing his own real estate stuff, but maybe there are other guys that don't want to do that, and they want to hire Pat to do it when it comes to venture capital.

You know, the thing is like all these guys grew up with social media and technology. All these guys grew up in the age of, you know, online angel syndicates and the social network and venture capital. But all this is stuff that they're interested in. So to me, it's like, You know, why hand that off to somebody else?

Why be a passive LP when this is something you're actually interested in and passionate about? Should a hundred percent of your money being there? No, absolutely not. Right. But. If you are going to take an active role, then really do take an active role. I mean, Matt, Matthew Delvin never talked to us about how he spends time with the founders themselves.

Baron Davis has shared the same thing where he really gets in on what makes this company unique. Why, why is he the best person to invest in it? Like those are the kinds of questions that yeah. I think athletes should get involved in. And then most importantly learn how to say no, because most of the stuff you're going to get pitched as an athlete.

Is probably going to be stuff that you don't want to do. And then maybe it's going to be like sports team related or whatever it is, learn how to let people down and learn how to say no, that's going to serve you the best when you're an athlete or investor.

Yeah, I think it was the junk yard dog. Jerome Williams that had. Like a specific strategy on how to say no, but we heard that from, from other guests as well. That was, that was fun.


So another takeaway that I have from the season and our guests that I really want to hit on is humility and authenticity. You could see it with our guests kind of come through. I mean, I guess that's the whole idea of humility is you're not actually talking about how humble you are. It just kind of comes through.

Right. But like Stuart Bradley, for example, NFL linebacker,  and then he takes a job as an analyst at Goldman Sachs working like 80 hour, weeks or seven, you know, I'm probably exaggerating like really hard work weeks


he was, he was in the TMT group.

You know?

Yeah, yeah. He's banging the keys or like punching in Excel, like work working with 2223, like a guy that I know that I've worked with was like 23 and Stewart's like 32 at the desk and they're working together and he even admitted, I probably wouldn't have had that opportunity to work at one of the top investment banks in the world if I didn't have the NFL pedigree or piece.

And that's why it was important for him to make that decision. Quickly when you realized his football career was over. So it's the stories like that, that I was just kinda like blown away from, but I was like, yes, we need more of that. Like, if you want to be successful as successful off the field, as you were on it, you really need to embrace like, okay, I got to roll up my sleeves and I got to do what everyone else is doing.

And I got to do it to another level. Cause they're all gonna, no, one's gonna take me seriously because they all know me as the athlete.

Yeah, I think the. Important thing to remember from some of our guests is that they know so how to handle setbacks because you know, when you're going to play a sport like football or really any sport, you're going to have setbacks injuries are a part of life. Losses are a part of life. And so in some way you have that level of humility that you just, you have to have.

Cause you know that there are times when even with best of intentions, she's at best of preparations. Things are not going to go your way. And what am I describing? I'm describing the startup journey. That's, that's exactly what it is. And so when you have like halal Rosen joins us and talks to us about like getting a media company going in the midst of a global pandemic or Megan Klinenberg, as we shared earlier, talks about all the challenges they had, just getting an apparel line stood up and all the mistakes that they made, or even Donnie Jones Tahani shares his story.

With tackles the globe and like not knowing how to make a TV show and figuring out on the fly, you have to come in from a learner's mindset and you'd have to come in from the mindset of like, yeah, I'm I don't, I don't know anything. Tell me. Right. And, and sometimes I think, you know, a lot of these athletes, like they are a lot more red in and I think folks give them credit for, and hopefully we get to share that on the show, but sometimes you do get to like play innocent.

And say, yeah, I don't know, please. Mr. Venture capitalists explained to me how this stuff works. Right. And, and, and the smartest ones use that to their advantage. And then when we get to have them on the show, we hear that like, Oh, they're, they're a lot more read into this stuff than, than most people realize.

You also reminded me, I forget exactly who it was, but when we talked to baseball players, they're like three out of 10 hall of fame, like the hall of fame career. Right. So it is, there is just that mental fortitude that they've obviously not just built up, but they, you know, almost like a predisposition towards that, , cause of their success on the field.

Yeah. What did you take away from just in terms of like our journey, doing the show? We had a lot of conversations early on about this like narrative at the broke athlete. And I'm curious how your perspective on that has shifted over the last six months.

yeah, that term broke athlete was something I just took at face value and that's on me for not actually. Pressure testing, you know, any of the, as Eric Winston, former NFL, PA president and guests on our show was saying, he's like, find me that find me the data, because it's not, it's not accurate or it's not out there.

It doesn't exist. It's not true. And he would know, because as in that role, you had to structure a lot to help ensure the safety and protection of retired NFL players. So yeah, it's changed tremendously for me. And I hope that. In learning on my own that also some of our listeners were also able to see that.

I think the other thing that maybe I didn't fully appreciate because I've gone through my own journey in this conversation. I remember like four or five years ago when I was leaving the NFL, I was thinking, Oh, these guys it's like steakhouses. Like they shouldn't be getting involved. And I personally, as I've talked to more of these athletes and gotten to know them, realize like, You know, a lot of this broke athlete narrative has been weaponized and it's been weaponized by business managers and money

Yeah, like who's writing the articles.

who's actually benefiting from the idea of saying you who excelled at one career, cannot Excel at this other career can not spend the time to get there. Well, because they're going to benefit off of. The management fees that you give them. Right. So we're not, we're

not saying we're not saying everybody

your money to me because you can't be trusted with 

I'm not saying everybody does that, Tim. But what I am saying is that I've become a lot more wary of when people use the dumb jock can't invest, you know, narrative. I, it puts me a little bit on edge because from the 35 episodes that we've done on this show, What we know to be true is that there are plenty of guests out there.

Plenty of athletes out there that defy that and sample size bias says they can't all be on our show. So clearly there's so many more of them that are out there that are thinking about this in much smarter way. And as we've said, are going about investing in a way that protects them and creates, you know, generational wealth and security for their families.

You know, another very real conversation we had, that's tangential to this topic. And I don't know, maybe this will come off as virtue signaling, but I'm just going to say it anyway. When we spoke to Angela Ruggiero, who is literally the hall of fame of hockey, golden medal, multiple gold medalists does like from a, just a pure quantitative standpoint has done anything you could possibly imagine to be the top.

One of the top, all time hockey players, not just female, like all time hockey players, and yet, like, she never made millions of dollars from any of that. And so I'm hopeful and. Excited in like our conversation with Hailey Rosen who started a publication to address that specifically just women's sports.

And I loved what she had to say, which was like this isn't like a social good exercise. Like women's sports are rad and I'm like, you know what? Maybe there's something to that. Like, you know, I'm a typical sports fan. Oh. You know, like blue blood sports, NFL, you know, Pascoe, NBA, whatever. But like ever since we had that conversation with her and like the NWSL came back and were playing, like, I was like, yeah, this, this sounds pretty rad.

And so I hope, you know, it's early, but like, I hope that it's true and can come to fruition that by drawing more attention to women's sports, They can start to make the kind of money that can set them up. Right. And, , you know, Meghan, Klingberg another example of that. Cause we've seen in, through talking to her too, like all the things the us women's national team has had to do to say like, by the way, we're driving way more media interest in soccer, we're getting way more attention.

And like we're not getting paid this much less the same, like we should be making more. So, , I don't know, again, maybe that's just seen as virtue signaling, but I thought it was worth mentioning because it's something that came up in, in multiple conversations we had. And just something that I've been thinking about since doing the

Look, we, we wouldn't be good at our jobs as investors, if we weren't challenging our own biases. And so we don't like to hear you say that. I don't think it's virtue signaling at all. I do think that. We learn as we get new information. And I think the fact that we get to hear it firsthand from somebody who is so passionate about what she is building or what any of our guests are building, it should give us a moment to reflect and say, yeah, maybe I have been thinking about it in one way.

So I guess why don't we use that as a, as a good place to close, you know, beyond I think our takeaways from our guests, we've also been putting together and producing a show. For almost six months. Give me some of your reflections and maybe some of your hopes as we go into season two.

it vests in a high quality microphone. That was, that was a good learning early on. Now look, no, there's obvious. I see plenty of things that you and I talk at length about often like that I'm not going to bore our listeners with, but I am really, really excited for season two. I think anyone who's listened to the show over the course of the season would agree that we've gotten more refined as the season's gone on, have done our best to ask deeper, more meaningful questions where we have some really exciting guests lined up.

And, uh, you know, can't quite hit on it yet, but looking forward to maybe some bigger things in season two.

Yeah, I think for me, Tim, the most exciting thing about this as like, we didn't know what this was going to be when we started. Right. And I think you and I joke about this a lot is like, Oh, we said, okay, 10 episodes. There'll be season one. We'll figure out what we want to do. Here we are three times that length.

And, , I think, you know, some of our listeners have, , if they follow us on Twitter, probably heard the story, but like we thought this was going to be done when COVID happened. And we were going from recording live together in downtown New York to, you know, I was recording from a supply closet for a couple of weeks until I had my whole setup ready


so what I will say is like, The biggest learning for me in this is it just gave me a tremendous amount of respect for podcasters, for content creators, for people that just put out quality content with consistency. It's tough, man. And the fact that we've been able to build the listenership that we have, that we have folks that come back episode after episode, they DM us, they share their thoughts.

They reach out and say, Hey, I've got a startup. I'm working on that. I think this guest would love to hear about. That's something I'm hoping to carry forward in the season two that we make this not just about the episodes and about the content that we put out, but you also make it about the connection that we can hopefully provide our audience to our guests.

And there's probably some cool things that we can do there. And hopefully we'll be able to talk about those soon as well.

Totally. I think that's a great place to wrap. And it's also a good reminder for our listeners, especially if you've gotten this far into the recap episode. Thank you for, for making it with us. We love hearing from you guys and your encouragement is what keeps us going. We'd love ideas that you have, whether it's for the questions we could ask for the type of guests we could have.

So please keep that stuff coming. Best way to reach us is through Twitter. Or you can also follow us on LinkedIn, where we post about the episodes quite a bit and have some commentary there, but, shout out to you as the listeners. We really appreciate you guys also want to make sure. That we think our production crew so big shout out to will Richardson.

Who's just been dialing it up all season for us, uh, helping edit, cut, put the show together so that you guys can enjoy it as listeners. , Megan Rojas as well has been a huge help just in promoting, , helping us on the content side and both Megan and will are going to be with us into season two.

We're excited to be working with them. Jay. That's all. I got anything else from you?

that's great. Thanks so much, Tim. We're excited to see you all in season two. 

Thanks, Jay.