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Family Office Podcast: Billionaire & Centimillionaire Interviews & Investor Club Insights

14 Aug 2026 · 8m · 5 chapters

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NFL Player Turned Lawyer Explains Why Letting Go of Control Was His Best Business Decision

In short

Otis Grigsby, a former NFL player turned lawyer, explains how letting go of control and resisting fear improved his performance and business life. He says he doesn’t rely on visualization; instead he “kicks ass” by focusing on the next play, staying upbeat after setbacks, and asking “can I get a little better today?” He claims fear causes paralysis and dumb decisions, citing his regret for not investing in Bitcoin/crypto after being warned by “smart guys.”

Notable examples

his Home Depot encounter where a man prophesied an administrative problem would improve if he stepped away; four months later he did, and “things started happening.”

Guest backgrounds

Otis Grigsby—six years in the NFL, based in the Austin area; practiced law for about six years at large firms; now works with his wife’s health-tech marketing agency, Distill Health, handling legal, growth, and strategy.

Written by AI. May contain mistakes.

Chapters

0:45

The Power of Fun and Resilience

Discussion on how having fun and resilience in challenging situations is key.

“But as long as I don't get down on myself, then I'm okay.”
1:46

Fear as a Limiting Factor

Otis shares insights on how fear can hinder decision-making.

“It's not like fighting someone on the football field, but it's pretty fun.”
2:13

Regrets and Lessons in Investing

Otis reflects on his biggest financial regrets and lessons learned from fear.

“I would say not investing in Bitcoin, not getting into cryptocurrency.”
2:59

Finding Purpose and Connection

Otis discusses the importance of connections and following a sense of purpose.

“I'm here because, to be perfectly honest, when I got invited to this, I was like, why are they inviting me to this?”
3:54

Letting Go of Control in Business

Otis explains his transition into working with his wife and the value of letting go.

“You know what happens when you're told to come and you don't go.”
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Transcript

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0:03Got Otis Grigsby to finish this update. Six years in the NFL. Yes. And you're, uh, you're rocking and rolling. Um, you're out of Austin area. Um, tell me, uh, tell me what visualization affirmation that got you to be a top one percenter. Yeah.

0:19Otis Grigsby: I didn't do any visualization. Um, what I, I just didn't, that's good. Tell me how it works. Yeah. So I went out there and just kicked ass. That's what he did. He's like, no, I'm just going to run you over. Well, you know, it's kind of like if you're having fun, then everything just happens for you, right? If you're in the place you're supposed to be, then you have fun. It's like, I'm going to play the next play. If I get hit in the mouth, okay, I got another play. Let's go back in there and do it again. Can I get a little bit better today than I was yesterday? I don't do that every single time.

0:47Otis Grigsby: But as long as I don't get down on myself, then I'm okay. So having fun is the key to that. And it's worked. But I mean, I'm not saying don't do visualization. but it's just, it's not for me. Okay. Yeah. Give me a$1 million lesson that you've learned. Man, fear is an absolute killer. I think I love just observing people. And I think no matter how much money you have, people are experiencing some form of fear about something that they care about. And it paralyzes us. It causes us to make really dumb decisions. You forget your training, You forget everything that you need to get you through whatever you're going through when you allow fear to step in and lead your path.

1:32Otis Grigsby: So for me, I'd say that it's a daily battle for me with a three-year-old and a two-year-old and a wife who's like, what are they doing today? And it's like a constant fight against that. And I enjoy the fight. It's not like fighting someone on the football field, but it's pretty fun. I mean, there's a difference between fighters. Like I was just watching bull riding, by the way, those people that jump motorcycles, you guys, you guys are crazy. Like, I didn't think I was that crazy. Yeah, we are a little crazy. Yeah. So, so give me, I agree. Yeah. So give me the, the biggest financial mistake you've ever experienced.

2:12Otis Grigsby: Man, there's so many actually. I would say not investing in Bitcoin, not getting into cryptocurrency. So going back to fear, I allowed fear to just kind of keep me on the sidelines. You looked at what was going on in the market. Really smart guys were saying, stay away from it, stay away from it, stay away from it. It's a scam. And then years later, they were like, oh, it's totally good. Let's get in it. And, you know, so I fell prey to that. And, you know, now I feel like I've learned that lesson and I'm smarter about it. But yeah, I wouldn't be here if I just invested in the cryptocurrency. I'd be on a beach somewhere, you know.

2:58On your own island. On my own island with my wife, yeah. She'd be swimming. Yeah, anyway. Okay, cool.

3:05Otis Grigsby: Why are you here? Yeah, why I'm here. I'm here because, to be perfectly honest, when I got invited to this, I was like, why are they inviting me to this? I don't know if you guys doubt yourself at times, but I sometimes doubt. And it's like, why am I here? And to be perfectly honest, I don't know, but I'm showing up where I believe I'm supposed to be. So I feel like God is basically saying, this is where you should go. And I'm like, okay, I'll go. So last night we had an amazing conversation. A bunch of other people we had great conversations with. So I'm learning things. I love learning. I love wisdom.

3:44Otis Grigsby: I love knowledge. And I love people. So, so far, so good. Great people here. So yeah, that's pretty much why I'm here. I was told to come. Cool. Nice. You know what happens when you're told to come and you don't go. Yep, really bad things. I have a long track record of bad things happening when I don't do what I'm told. Yeah. Yeah. So tell me, I've had some experiences. So tell me why, what you're up to today. Tell me what you're doing. You're a lawyer. Yeah. Yeah. Underachiever. Yeah. You know, that's a, gosh. Yeah. I think we're all in this room overachievers and there's this kind of, I'm a lawyer.

4:24Otis Grigsby: Yeah. I practiced for about six years in large law firms. I was surrounded by people who were really smart and not really happy. They've got the money and they've got all this stuff. And it's just like, yeah, enjoy this time now because it only gets worse and worse and worse. And you realize the clients they get, the bigger the clients, the more they want. It's like, oh, hey, you want Christmas off? Sorry that we're not doing Christmas this year. Christmas is canceled. IBM needs this deal done. So I'm now working with my wife. She has a health tech marketing agency called Distill Health. And I'm really working on just letting go of control, right?

5:09Otis Grigsby: I think that's really what I'm focused on. Again, doing what I'm told. I am making dinners for my kids. I'm building things on our land. I'm doing things. I'm baking bread. I'm milling my own flour. It's crazy. Like the health benefits of like real bread, unbelievable. So, so like I'm doing, I'm doing those things. And, and just to, I know I'm like going over time here. I'm so sorry. Um, I was in a home Depot, right. And a guy comes up to me. I spent a lot of time in home Depot and I, and a guy comes up to me and he's like, he bought a lot of acreage outside of Austin, just to give you guys a context.

5:50Otis Grigsby: Yeah. Yeah. Yeah. We moved from East Austin. Yeah. And it was the best thing we could have done. So I'm in Home Depot and this guy comes up to me and he says, hey, God gave me a word to share with you. Can I like share it with you? And I was like, bro, I've heard of this happening to people. It's never happened to me. Please share what you have. And he said, there's this thing in your business, some big administrative problem that you're struggling with, you've been wrestling with, and you need to step away from it. You need to just leave it alone. And I was like, I know exactly what you're talking about.

6:25Otis Grigsby: And I do not want to. I don't want to. And I was like, OK, that's cool. I'll do that. I'll do that. And four months later, I still hadn't done it. And then finally, I did. And things just started happening. So my role with the company is part legal, part growth, part strategy. And I found myself kind of obsolete. Because they don't need anything. I don't need it. We don't like the business just comes. Literally, like I mentioned last night, chat GPT is telling people looking for services that we're the best for that service. I don't know how to program chat GPT to do that, but that's so anyway.

7:05Otis Grigsby: So like letting go of control and just being led is what I'm working on. And it's leading me on a wild ride. Love it, bro. Yeah. Nice. Thanks for coming today, bro. Yeah. Thanks for having me. Yeah. I appreciate you. Awesome. Give me a round of applause, guys. Join the Family Office Club by visiting familyoffices.com. We look forward to seeing you at our next live event.

7:32If you are a founder, raising capital, developing real estate, or you're an investor, we'd love for you to get involved in the Family Office Club. I've run this community for 18 years now. We've hosted 300 live events. We have 17 million social media group members and followers. We have the number one YouTube channel on Family Offices. We have the number one most popular podcast on Family Offices. You can learn more about us and our membership options at familyoffices.com. We have 30 in-person events planned in 2026 and another dozen events this year. Please go to familyoffices.com to learn more.

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Fear paralyzed him on Bitcoin. A decade in prestigious law firms surrounded by smart, unhappy people showed him what success without purpose looks like. And a stranger in Home Depot delivered a message that changed the direction of his business. Otis Grigsby played 6 years in the NFL, practiced law at large firms for 6 years, and is now part-legal, part-growth, part-strategy at his wife's health tech marketing agency - and watching ChatGPT recommend their services to strangers without any programming on their end.
In this episode, Otis delivers one of the most honest 10 minutes on this stage: fear is an absolute killer, it paralyzes your training, it makes you forget everything you've built - and it shows up daily whether you have a two-year-old at home or a nine-figure deal on the table. He talks about missing the Bitcoin run, what Christmas in big law looks like when IBM needs a deal closed, and the four-month delay before he finally followed the advice that unlocked his business. Family Office Club has hosted 300+ events over 19 years and $1 billion+ in community transactions - Otis is the kind of operator you only meet in rooms like this.
What is the one thing in your business you keep holding onto that you know you need to let go of? 

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____________________________

Otis Grigsby spends most of his time helping his wife raise two exceptional young children. When he's not making wildly helpful and entertaining parenting content for Parent Like an Athlete, Otis serves as the Director of Growth at Distill Health, a Healthtech marketing agency. Otis is a licensed attorney who spent five years at Taft Law and Pillsbury Law before working at two venture-backed Sports Healthtech companies, Players Health and Oculogica. Before attending law school at the University of Kentucky, Otis hit people for money in the National Football League for over six years, playing defensive end for the Miami Dolphins, Carolina Panthers, and Minnesota Vikings.

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