055: Taylor Prokes | The Real Way to “Get Lucky” in Life

Summary

Podcast Episode Summary

Podcast: The Matt King Show
Host: Gobundance
Guest: Taylor Prokes
Episode: 055: Taylor Prokes | The Real Way to “Get Lucky” in Life
Date: April 14, 2026

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Overview

In this energizing and candid episode, host Matt King sits down with adventurer, entrepreneur, and endurance enthusiast Taylor Prokes to unpack the real roots of "luck" and the intentional strategies—and fearless leaps—behind a life brimming with serendipity, connection, and adventure. Taylor shares her unconventional journey from small-town Michigan to global endurance events, running wild challenges, and eventually building the Big Ass Calendar Company. The discussion dives deep into themes of risk-taking, the compounding magic of showing up, building extraordinary communities, and designing a movie-worthy life through memorable experiences—never mere happenstance.

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Key Discussion Points & Insights

1. Creating Your Own Luck

• Taylor debunks the myth of accidental luck, emphasizing relentless initiative and creativity.

  • Quote: “If you don’t have a seat at the table, make one. Don’t wait for luck to happen to you. It’s not gonna magically happen.” (Taylor, 01:09)

• Her journey began by boldly running 100 themed hill repeats (in costumes!) to earn an invite to Jesse Itzler’s iconic Hell on the Hill event, demonstrating the compounding effect of putting yourself out there.

  • Memorable Moment: Taylor’s commitment to 100 hill videos, “It was like embarrassing myself on the internet. I wasn’t embarrassed, but my friend…was like, ‘I’m trying to date, this cannot be on my profile.’ But I said, I just want to go to this race. I do not care.” (Taylor, 04:14)

• Proximity as power: Creating value and high energy without agenda leads to invitations and opportunities (05:24–06:40).

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2. The Role of Risk, Resilience, and Taking Leaps

• Taylor discusses her high risk tolerance—moving, living out of her car, and seizing new opportunities as they come.

  • Quote: “What’s the worst that can happen? If you have a good feeling about something…worst case, I go back home with mom and dad.” (Taylor, 10:08)

• She credits her supportive upbringing for this confidence:

  • Quote: “My dad always says, if you don’t like something, change it…he really pushed me to go and try and celebrated it the whole time.” (Taylor, 12:33)

• Both Taylor and Matt reflect on jumping at unique chances even in the face of skepticism from family and friends.

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3. Embracing the Highs and Lows

• Taylor describes living at a “ten” sometimes means crashing to "one" and loving the entire emotional range.

  • Quote: “If you want to hit the tens in life on a scale of 1 to 10, you’re also going to hit the ones, twos, and threes.” (Taylor, 15:22)

• Contrasts with “living at a 5 or 6” and the discomfort it brings her (15:00–16:30).

• The antidote? Community and deep connection. Her family, close friends, and teammates see her through “hard things” and business challenges.

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4. Building Community and Doing Hard Things

• Taylor details how shared suffering through endurance challenges builds true family, not just "business partners."

  • Quote: “When you work with people who know how to go through discomfort at that level and have chosen it…when something goes wrong at work, people aren’t stressing the same.” (Taylor, 18:03)

• The discipline and lessons from physical endurance events translate directly to business resilience.

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5. The Evolution of Adventure: New Forms of Growth

• After years of constant travel and high-adventure, Taylor’s newest challenge is building community and being present—finding discomfort in “slowing down” and nurturing local friendships in NYC.

  • Quote: “What’s uncomfortable for me is staying in one place…saying no to trips…It is hard for me to slow down.” (Taylor, 20:13, 22:37)

• Highlights the parallel between showing up for physical endeavors and intentionally investing in relationships.

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6. Being a Catalyst: Creating Experiences

• Taylor’s "why not me?" spirit has her launching flash mobs, spontaneous dance parties, and no-phone gatherings.

  • Story: Recruiting a stranger in the park to power a Taylor Swift flash mob. “We just trusted him…he showed up.” (23:27–24:41)

• Willingness to be the instigator rather than waiting for others drives both joy and connection.

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7. Big Ass Calendar & Living Deliberately

• Taylor gives an inside look into the "Big Ass Calendar," a product and movement helping people map their entire year for maximum intentionality and fun.

  • Quote: “Look at your year as a whole…really changes how you view time…all the best moments in my life over the past eight years have been planned.” (Taylor, 26:09, 34:52)

  • The power of anchoring one’s year around a “misogi”—a singular, significant challenge or experience.

• Community as a multiplier: Surround yourself with other goal-chasers and watch your own possibilities expand.

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8. Kevin’s Rule and Accessible Adventure

• Sharing Kevin’s Rule: “A mini-adventure every other month.” Not always grand or costly; just something novel to disrupt routine and spark joy.

  • Quote: “He just breaks himself out of his routine…The goal is to always have something to look forward to and break you out of your routine.” (Taylor, 31:06)

• Matt and Taylor stress: Most meaningful experiences are accessible; cost is often less than imagined.

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9. Fun as the Secret Ingredient

• For Taylor, integrating FUN is key to personal and professional relationships—a lesson from her upbringing and a pillar of communities she’s building, especially for women.

  • Quote: “Fun is such a big part of my life and business—it’s completely intertwined.” (Taylor, 45:20)

• Matt and Taylor agree: authentic connection and joy are more sustainable and impactful than purely transactional business goals.

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10. Advice for Listeners: Start Your Own Movie Scenes

• Taylor’s #1 actionable tip:

  • “Put something on your calendar that would be so meaningful that you’d say, ‘I can’t believe I did that this year.’ The most life-changing thing I’ve implemented is having that one year-defining ‘misogi.’” (52:00–53:00)

• Misogis are relative: May be a marathon, a new skill, or a creative project—what matters is making it personal and committing publicly for accountability.

• “Ordinary people can do whatever they put their mind to.” (Host, 58:44)

• “If you want to connect with people, do stuff…when you put things out there, people think of you and send opportunities your way.” (Taylor, 64:07)

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Notable Quotes & Moments with Timestamps

• On Luck and Initiative
  “If you don’t have a seat at the table, make one. Don’t wait for luck to happen to you.” (Taylor, 01:09)

• On Risk and Opportunities
  “What’s the worst thing that can happen? ….Worst case: I move into my parents’ basement. Right. I do have that. So maybe that’s part of it too. But…I just try something.” (Taylor, 10:08–10:44)

• On Emotional Range
  “If you want to hit the tens in life…you’re also going to hit the ones, twos, and threes.” (Taylor, 15:22)

• On Community as Jet Fuel
  “When people have been around you in those [ultra-demanding] situations, they can help you through anything.” (Taylor, 16:33)

• On Planning for Spontaneity
  “All of the best moments in my life…have been planned. Because it’s the journey of getting to something you care about.” (Taylor, 34:52)

• On Purpose and Authenticity
  “It’s more sustainable to start with the authentic connection…If you have actual relationships, you can do so much more for each other.” (Taylor, 50:56)

• Action Challenge
  “I would put something on your calendar that’s meaningful, that maybe scares you a little bit, that can anchor your whole year around.” (Taylor, 52:19)

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Segment Timestamps

• 00:03 – [Opening: Luck as Action]
• 01:09 – [Origin Story: Hell on the Hill & Creating Opportunity]
• 06:40 – [No Agenda, Just Energy]
• 09:17 – [Risk Tolerance and Moving Toward Opportunity]
• 14:46 – [Movie-worthy “Pinch Me” Moments]
• 15:22 – [The Emotional Range of Living Big]
• 18:03 – [Endurance, Business & Community]
• 20:13 – [Evolving Adventure: Slowing Down as Challenge]
• 23:01 – [Flash Mob Creation: Taking Initiative]
• 26:09 – [Building the Big Ass Calendar]
• 31:06 – [Kevin’s Rule: Frequent Adventure]
• 34:52 – [The Power of Planning and Spontaneity]
• 45:20 – [Fun, Gender, and Community]
• 52:19 – [Action Challenge: Design Your Misogi]
• 64:07 – [Visibility, Accountability & Attracting Opportunity]

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Final Takeaways

• “Luck” follows action, creativity, and risk.
• Communities of extraordinary people are built through shared experience, vulnerability, and mutual fun—not just by networking.
• Anchoring each year with one big goal or memorable adventure (a “misogi”) leads to a rich, intentional, and joyful life.
• Don’t wait for an invitation; create the experience you want—and watch the world conspire in your favor.
• Authentic connections trump transactional hustle, in both life and business.

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To connect with Taylor:

• Instagram: @aylorprox and @hebigasscalendar
• Big Ass Calendar and resources at: bigasscalendar.com

Challenge for listeners:
Put one year-defining adventure or challenge on your calendar today. Don’t wait for luck—create it.

Transcript

[Host]

So most people would look at your life and say, you got lucky. Like, they're looking at the movie that you're living in, in this moment. But I don't think you got lucky. I think you created your own luck. Tell me about how you've gotten into the position you're in today.

[Taylor]

The position being just traveling around the

[Host]

world doing sauna tours, 29029s, bikes across America, Big ass calendar, Good Morning America.

[Taylor]

I think it's probably similar to how you live your life. Where it start, starts small, like a little snowball. And it just keeps the momentum, keeps building on itself. One thing leads to another. You do one event, you meet cool people who invite you to another thing. They find out, oh, you ran this race, you got to check out this, you got to work with this person. It's just everything. The business and the endurance sports all build on each other. So it started really small. I didn't know what I was doing at all about anything. And then it's just keep following the energy and.

[Host]

But how did you get that first door to open? Like, you're watching Jesse from afar, you're watching Sarah from. Like you're watching all these people from afar. How did you get their attention?

[Taylor]

So I found Jesse back in 2017. He was much smaller then. He might have had 60,000 followers. So he would see if I posted him, tagged him in the DMs. And I saw that he had this event called Hell on the Hill. And he had had it for several years at that point. And I had watched it somehow. I don't even remember how it got on my radar, but I was just getting into my first half Ironman. I had never run races before. I was learning everything brand, brand new. And I found Jesse. And he was so bizarre. And the things he was doing online, I just wanted to be in that energy. I didn't know how to meet these people, but thank God for the Internet because they were showing them to me. And at the time, he was. One of the things he talked a lot about was, if you don't have a seat at the table, make one. That was one of the things he would say all the time, don't wait for luck to happen to you. It's not gonna magically ever happen. Get yourself into the room. Be creative. So I, I thought he would be open to this. And he is. He's very open to new connections, new friends. He loves meeting, entertaining people. So I was living in San Diego at the time, and I had a friend out there with me. And I watched this race. So Hell on the Hill is an event where you run up and down a hill a hundred times. It's a backyard race he just hosted at his house. We just had the 10th anniversary anniversary last year. So you do it for four hours. A lot of people are going to hear that and say, that doesn't sound fun at all. But I thought it sounded so fun and I wanted to go to that race. So I watched it happen in 2018 and I told my friend, I have an idea of how we can maybe get invited to this. And it was to make 100 videos of us running 100 hills for hell on the Hill and post them online and try to get Jesse's attention over the course of a year. So we posted three. We posted 100 videos. Every video is a different theme. The first video we posted said, hi, Jesse, this is Taylor, this is Kate. We want to be invited to Hell on the Hill and we're about to entertain you for a year. And the rest of the videos, there was no ask, it was just entertaining. It was us running around in banana outfits and kind of costumes and making fools of ourselves in the public gym and running in through the streets of San Diego just doing crazy stuff. And he was seeing them. And a couple weeks out from Hell on the hill in 2019, he said, okay, if you two lunatics want to come, you're invited. So that's how I met him. I was working my full time job and my part time job was this. It was like embarrassing myself on the Internet. It's very hard to embarrass me. I wasn't embarrassed, but my friend at the time was like, I'm trying to date. This cannot be on my profile, but like super cool if you want to put it on yours. And I said, I just want to go to this race. I do not care. So that's how it started. And that is not an unusual way for me to live. If I have an idea, I'm not embarrassed to do it. That obviously opened me up to public failure. People watched me do something for a year. High chance I don't get invited. I don't know anybody at this place. And Sarah and Jesse were really important people from afar to me at the time too. So that's like a pipe dream. So got invited there. We were the MVPs of the weekend. I mean on the hill, highest energy, cheering for people jumping off the rocks into the lake, being MVPs at the party, I mean, just trying to make the most of it. It was One of the funnest weekends I have ever had in my whole life. And then it just builds off itself over time, but it's putting yourself out there over and over again. Like, Covid happened right after that. I didn't see Jesse for two years. I did other crazy things on the other side of COVID to get back on his radar. And I wasn't trying to work with him. I was just trying to be a part of the crazy things he does.

[Host]

Yeah. What I hear you saying is you recognize that proximity was power. And you're just like, I want to be around cool people doing cool things, because it's going to change the way you lived your life.

[Taylor]

They were just so fun, and I didn't want anything out of them but to have fun. I knew they had fun around me, too. So it just felt like, yeah, it was proximity, but with no ask except to have a good time.

[Host]

But you knew that you would have fun with fun people. You're like, those are cool people. That's powerful to be around cool people, not powerful.

[Taylor]

I want to be around these freaky people.

[Host]

Yeah. I just want to do cool stuff.

[Taylor]

Yeah.

[Host]

I want to live life a little different.

[Taylor]

And we think cool is the same thing. And I couldn't find who. I couldn't find those people in the wild on my own.

[Host]

Yeah.

[Taylor]

They're the only example that I had at the time. I mean, that movement has changed a lot in the past eight years. The. The do hard things, and those crazy endurance events have gotten a lot more popular. In 2017, 2018, it was niche. Like, ice baths were niche. People weren't signing yet. All. It was very different. So to see someone doing all of these things was so intriguing.

[Host]

Well, I think the coolest part is you didn't do it with an agenda. You weren't like, I'm going to get invited to the hill. Then I'm going to work for him. Then I'm going to help with the big ass. Like, you had no agenda. You're just like, I want to have fun in life. That looks really fun. And nobody around me is doing cool shit.

[Taylor]

Yeah, exactly.

[Host]

And so you went to hell on the hill. Then Covid happens. Where did it go from there?

[Taylor]

So he had launched a running company called all day running co. During COVID they did, like, short shorts, fun hats. And because we knew them, we got some early merch. Me and my friend Kate. Again, same once. We were living in Utah at the time. And then I said, okay. I think another way to get back on his radar Would be to do this challenge I came up with called 10 Hard Things, where we would wear the gear and do 10 hard things in the gear. So we did a 10 minute ice bath. We did an ultramarathon, like on a whim, untrained. We did a mile bear crawl. We ran like 16 miles to get a burrito. One day, just for fun. We jumped out of a plane dressed as bananas. I mean, it was 10 bizarre things in the gear. And so for us, if anyone has started their own companies, people doing fun things in your gear is awesome when you have no marketing yet or spend behind it. So. So they loved us for that. Got back on the radar. We paid to go to a couple events. So it just was again, just getting back in the swing of things. Got re invited to hell on the hill. And then I was trying to do work for the running company. I was trying to start my own company and I saw their social media for running company and I said I could do a way better job at this, like hire me to do it and that'll be my side gig while I start my own thing. And they, I did a bunch of work for free for them. I had no portfolio outside of my own, like TikTok and Instagram and which is pretty weak, but I knew I could do it, so I was doing free work. They went with a agency who could do a lot more than me. Email, all that. I said, fine, no, no hard feelings, but I'm going to turn pivot into a different direction and just go all in on my company. I went to move home for a little bit while I figured out how I was gonna have an income stream so I could start the company. And the day I found my manufacturer, Jesse called me for him. So that's how it started.

[Host]

And you moved down to Georgia in two weeks. Wow.

[Taylor]

He's like my one exception that I would ever want to work for because I, I would never. I don't want to work for anybody. I want to build things. I, I want to build things I care about, but I care about what he cares about. And I think he's unbelievably interesting. And after knowing him very intensely and intimately, I feel the same. He is one of the most interesting, awesome people I've ever met.

[Host]

Yeah. And what did you feel like when he called and said, like, hey, you want to move to Georgia?

[Taylor]

Like, my life's a movie. Like, to me that's like, duh, I'm moving to Georgia. And it's funny because I'm trying to Hire people to do certain things now. And that's not everybody's reaction. They're like, oh, I live here. I do this. And to me, I've moved a lot, and I'm very motivated by opportunity. So moving to Atlanta or wherever he was living was a no brainer.

[Host]

Yeah.

[Taylor]

I was like, I'm about to enter a wild ride. I know that.

[Host]

So, yeah, the cool thing is, is, like, my story is similar. Like, I didn't have an agenda to work for David Osborne, but I just, like, was like, this guy's up to cool stuff, and I'm just gonna find a way to be of value to him, like, whatever that looks like. And similar to you is, like, two weeks later he calls. Like, what would it take to get you to Austin? I was like, like, dude, I've never been.

[Taylor]

You're like, nothing.

[Host]

I was like. I was like, I've never been to Texas. Yeah. So we came to Texas, and like, my parents were like, don't do it. Friends were like, don't do it. You don't know this guy. Like, what are you thinking?

[Taylor]

What's the worst thing that can happen? I don't know. If you have a good feeling about something, what's the worst thing that can happen?

[Host]

Well, and that's literally what he said. He's like, I think you're talented. If it works, I got opportunity for you, and if it doesn't, move back to wherever the hell you came from. I'm like, okay, so heads you win, tails I lose. Worst case, I go back home with mom and dad.

[Taylor]

Like, I hired onto Jesse as a contractor and gave him some stupid rate for he. For him to just make me a no brainer. I'm like, let's just make this a no brainer, and we'll figure out the rest later if this works for us.

[Host]

So as you're hiring, why do you think people don't see the world that way? Because I have the same experience. Like, you're talking to talented people or at least you think are talented. Like, can I work remote in Ibiza?

[Taylor]

Like, no, it's not even that. It's like, can I work remote in Ohio? Is what I'm working with. And I'm just like, especially to people in their 20s. I think what I'm surprised about is using our world as an example. Jesse's world is so unusual and what you get to experience and the people you get to meet and the things you get to build and work on are so you can't find it at other companies. It's once in a lifetime and for people not to take a risk is. I don't know why I think I have a high risk tolerance. I've lived in my car, I've moved a million times. People have asked me why I move places and just like on a feeling, you know, I don't need a really deep reason to try something because worst case scenario I will say I have a great safety net, I have the best family in the whole world, I won the jackpot. So I do understand like the privilege of that is that worst case scenario I move into my parents basement. Right. I do have that. So maybe that's part of it too. But I don't know. You just, you realize when I read people's books that I look up to or people's journeys I looked up to, none of them are linear. None of them are people climbing a corporate ladder like this and everything working out for them like this. It's they're working in this job and they quit and they biked across America and they wrote a book about it and this company failed and then they met this guy because you know, it's a bunch of stories like that. So it makes me feel really confident that if I crash and burn. Oh well, at least I tried.

[Host]

Do you think you get this risk tolerance from your mom or your dad?

[Taylor]

Um, my dad always says if you don't like something, change it. And he really pushed me to leave small town Michigan for college. Even I knew one person in the four grades ahead of me that left the state of Michigan for college and she's the only person I needed. Shout out Aaron fueling like someone who doesn't even know I was looking up to her for that reason. But he was like go. Like I never left, like go, go see the world. So I wouldn't even say it's that he's super, he's not a high risk individual but he really pushed me to go and try and celebrated it the whole time. My mom too. But he was very verbal about like get out of here and go try things and if you don't like it, change it. He's never like, oh stay, it's safe. No, never.

[Host]

So you just described your life too as a movie. What would be your favorite scene thus far in the movie of your life?

[Taylor]

I would say, I mean the turning point in my life. So you have to understand like Jesse and Sarah were so they are still. But I know them at a very personal level now but before I knew them like they hero's not the Right word. But I looked up to them so much and very inspirational to me. And then I get a call and I'm. I moved down to Atlanta. I didn't have a place to live, so I was living in their guest house. So it's like I was living at their house. All of a sudden. Jesse would be like, let's go sauna before we go to bed. And I'd be in the sauna with their whole family, and then I'd be laying in bed going, like, what the hell is going on? Like, you know what I mean? I couldn't have written this myself. And so that was a very pivotal moment to me where I was like, if I could make this happen, like, this isn't. This isn't. This was not on the bingo card. I couldn't have dreamt this up then. What else can I make happen? But I could name a million examples. But I feel like that one is kind of one of those moments that felt like anything is possible.

[Host]

Did you ever have a moment where you were just, like, laying there, like, crying or cheering or jumping, going like, holy cow, I cannot believe this is my life.

[Taylor]

I feel like that all the time, though. I feel like that all the time. I feel like that on a weekly basis.

[Host]

Yeah. I think people that follow you or watch your journey, like, have a feeling through the phone of, like, you just live with energy. Like, you're like, I got an idea. I'm gonna go do something crazy. And you just go do it. And I think a lot of people see you smile and enjoy life and embrace all that life has to offer. Do you find any times where you're

[Taylor]

down, though, where you're feeling frustrated all the time? I think if you want to hit the tens in life on a scale of 1 to 10, you're also going to hit, like, the ones, twos, and threes. Before I came into this world, I was sitting at, like, a five, six a lot. I was living in San Diego, which has a lot of people, I think, that love living at a 5, 6. The weather is always the same. You wake up and are going to do the same thing. And year round, it attracts people who just want it to be like, even a six or seven. Life is good and it's the same and it's predictable. And I was. I didn't understand at the time because I hadn't experienced enough, but I felt so uncomfortable there, and I couldn't figure out why. I felt like I wanted to scratch my skin off. And it's because I like going up and down. And it's not like the adrenaline effect or chasing a high, but I love experiencing the range of human emotion. I like being like, holy shit, I cannot believe that happened. And then at the same time, that means I'm going to be like, my world is ending. Like, this was such a stupid idea. Like, I'm never doing this again, you know? But I think if you're shooting high, you're going to crash all the time.

[Host]

How do you get through the crashes? Is it people? Is it experiences?

[Taylor]

People, people? I have the best people, so I have my family. My family includes my sisters who were best friends. And then I have a best friend, Kate, who. Who is like, my whole life would be different without them. And I recognize that every day. And then everyone like, Jesse's amazing. Alex, sign on. My business partner is amazing, and I say business partner. But we do everything together. Like, we really live the essence of all of our companies. Everything's about connection. We've done so many. We've been in so many scenarios between, like the festivals we throw and endurance events that we do. Everyone that I work with, we've. Half of the people I work with, we've done 100 mile races together and have paced each other on these things or run them together. And you just see each other at the craziest times. So my lowest lows, while they're. I've run some long races and I've hit really low points in my mentality around these people. And even though that's a controlled environment that can just like end if you quit at any time, it's not like heartbreak or grief. When people have been around you in those situations, they can help you through anything. You know each other at a really different level. And I have a lot of people like that in my life.

[Host]

Yeah, I think that's one of, like the. The jet fuels you guys have in the businesses you're running is your family. You're not. You're not employees. You're not business partners like your family. You guys are ride or die. We're gonna go do hard things. We're gonna see each other through the good, through the bad, through the ugly. And then this business problem almost becomes irrelevant because you're like, hey, we got through that thing together. This is way easier than that.

[Taylor]

Also, a lot of people that we work with, when I say most people I work with have either done iron mans or 100 mile races. Most people I've worked with have done Iron Man's 100 mile races, which is really far and People have suffered a lot and they know how to train and they know how to do things when they don't like to do it. And when you work with people who know how to go through discomfort at that level and have chosen it, when something goes wrong at work, people aren't stressing the same. You know, it's just, how do we put out this fire? Or what's the solution versus panic? Doesn't happen even when I think it warrants it.

[Host]

Right. You just find a way to do extraordinary things by being incredibly ordinary but incredibly disciplined around the ordinary. Like, just staying disciplined to, like, we know we can get through this business problem. We just have to work a little harder, think a little differently, challenge ourselves a little more. And I think there's a really cool correlation between doing the Ultras and the Ironmans and the 29 029. Because you find those moments on the mountain in 29029 or in the water in an Ironman or on the bike. And then you take that and you bring it back to life and you're like, oh, this is just a part of the journey. I'm just going to.

[Taylor]

Jesse always says it about 29. He goes, if you do 29 or 29, go back home and think about, like, can you double your business plan? Because you just did something you never thought it wasn't on your radar before. It's so hard. And even if you're trained and ready for it, when you get on the mountain, it's so hard and you want to quit so much. And once you work through something that makes you feel like you're struggling that much, I think it makes you reevaluate how far you can go in other areas.

[Host]

Yeah, that's why I do something every year that scares me. That's why I wrote a bull. That's why I've done 29029. That's why I'm doing the ride. Like, when you do those things, it makes everything else almost seem like, irrelevant. You're like, this business problem isn't really a problem. That 2,000 pound animal wanted to kill me.

[Taylor]

Like, that's a problem I feared for life. Like, I can handle this.

[Host]

Yeah. Like, I can handle this. So as you think about your life, how do you constantly, like, raise the bar challenges? Like, what's the next adventure? What's the next thing you're gonna do?

[Taylor]

Well, for the past eight years, I've been doing a lot of physical things and you've probably had a similar thing. You talked about running a lot of marathons. And now you're doing this crazy bike ride across America. Physical things can snowball really easy. I started with a half iron man. And I mean, to train for that, you do a sprint, then Olympic, then the half, and then that turns into 100k and turns into 29. 29 turns into rim trim. Trim turns into 100 mile race like it snowballs. And I think even though maybe suffering physically isn't scary to me, because I've done enough things that I never thought I could would do, I really believe that I can do anything if I train and get mentally prepared for it. You do grow so, so much. So I don't know if I would be growing the same if I just kept down that path. And every year I was like, instead of 100, I'm doing 200 and 300. But for me right now, because I've been so nomadic for the past 10 years and have prioritized challenges like that and work so much, I've been really on the go and I' I haven't had a home ever. And for me, what's really comfortable is traveling, like several times a week and training all the time and working all the time. And I'm really focused right now and building community. I'm focused on dating for like, the first time in five years. So for me, like, slowing down, saying no to trips, because now I have all these friends who want to do all this cool stuff because I've been building them up of all these cool things all the time. So. So what's uncomfortable for me is staying in one place. And if I say that I want to build community, like staying home and doing it, which I think is opposite for a lot of people, but it is hard for me to slow down. So actually this year, I moved to New York City a year ago, and it's really important for me to build community. So I'm going so hard in the paint on that I'm like doing two things a day, six days a week. Like, what would be unsustainable if I was also training and also doing this, but because I want, like, hyper build the community. It's really important to me right now.

[Host]

Yeah, but like, you really want to be present, like, slow down and be present to home. A home that you're building a home.

[Taylor]

A home only gets built if you're putting time and effort into it. People want more relationships, they want friends, and the only way to get them is to put time and energy into it, like anything else. So I'm doing that at A very high level right now, I would say,

[Host]

how the hell do you think of this Taylor Swift dance party thing with a guy holding a speaker in some random party? Like, where does this come from?

[Taylor]

I don't know. I think I love getting people together, and I think it probably just crossed my mind. I wish someone else would do this. I wish someone else would throw a Taylor Swift flash mob to Ophelia. And I'm like, well, no one is. So I guess I will. I mean, that's it. Like, I want to experience that. So I'm not gonna wait for someone else to do it. I'm just gonna try.

[Host]

But talk to me about this guy that was holding the speaker. Like, how did you find that guy?

[Taylor]

I have a friend, Lindsey, in New York City. Have you ever met Lindsay Fritz? She's. She's crazy, but she'll go up to anyone and talk to anybody. And we were walking through Washington Square park and we needed a speaker. We were gonna probably rent one. We're all. We're flying at the seat of our pants, throwing this flash mob. And if you've ever walked through a park in New York City, there's a lot of people with speakers. Like, they come to the park and it's a whole situation. So I said, can we maybe ask a couple of these people if they would just come back with their speaker later? And Lindsay goes, yeah, no problem. So she walks up to the first guy we walked up to was like, yeah, I'll go charge it up and bring it back for you guys tonight. And so the whole day, we're just like, should we rent a backup speaker? We just invited a lot of people to this later, or are we going to trust this complete stranger to bring it back? And guess what? He showed up.

[Host]

So you just trusted him?

[Taylor]

We just trusted him. We just trusted him. I don't know. I think. I think we tried to make him feel special and a part of it and gave him every opportunity to tell us he wasn't gonna show up for us. And then. Yeah, you just gotta trust the rest. So, yeah, he. Alfonso, Shout out.

[Host]

He brought the speaker back.

[Taylor]

Yeah.

[Host]

And held the mob. And how many times did you do that? Two, three, four?

[Taylor]

Just one. I'm sure we'll do another one. I learned a lot from it. People need some time to catch on to things, and they do catch on. All of my promo that I put online for that got a lot of traction at, like, week two, so I would plan it a little further in advance. I don't know if you've seen any of these lookalike contests in New York City?

[Host]

No. What's that?

[Taylor]

There's like they just had. What's the Kennedy documentary that's out right now?

[Host]

Asking the wrong guy.

[Taylor]

There's like Timothy Chalamet look alike contest and the whole park will fill up with people that show up looking like him.

[Host]

And so what's your look alike contest? Who are you gonna do?

[Taylor]

No, I don't know. But people are just down to go do random things is the point. Yeah, people just put flyers around, put a couple tic tacs up and people just want a random thing to do.

[Host]

I think you should do a Jesse lookalike. Like, I mean, like it would be hilarious to see what people showed up as.

[Taylor]

I know. And he has some like very defining characteristics. So.

[Host]

Yeah, like somebody told me you ran with him in New York City and he wore socks as gloves or something like that.

[Taylor]

Yeah, he's very low maintenance. So he. And we're just always on the road. So gloves don't make it to the bag, but socks always do. So if it's cold enough, he'll just put socks on his hands.

[Host]

It's logical.

[Taylor]

Yeah.

[Host]

What inside of your life are you most excited about?

[Taylor]

I'm excited about so many things right now. I'm really excited about the big ass calendar that we're building. It feels like there's so much momentum and it's just fun. The community around calendar for those who don't know, the big ass calendar is our flagship product is a calendar that shows all 365 days on one page. And the whole idea around the big ass calendar is to get people to live bigger and better lives. We really want people to prioritize their life before their meetings. Put all the big goals on your calendar first. Everything else fills in around do the bucket list trips. Put time into planning your most valuable resource, your time. And I don't think people generally do that. They'll do like a vacation here or something there where they'll sit down and plan. But looking at your year as a whole really changes how you view time. But what's so fun about this is it's so positive when people go do that. They say, oh, I ran an ironman for the first time or I saw my parents more or I just did this thing I never thought I could do or I started my business. So the more the bigger we make calendar, the more just good energy that's coming our way. And right now it feels like a tidal wave. And I see where it can go. And it's just very exciting.

[Host]

Yeah. Jesse spoke at a gobundance event maybe four years ago. And my wife came because it was in Austin. And I've always been a super, like, goal oriented human being. Like always said a bunch of goals and that's just not who she is. But for some reason, the way Jesse talked about the misogi and Kevin's rules and like his plan for his big ass calendar just like resonated with her. And after that she ran a half marathon, then a full marathon. And so like we really adopted this whole lifestyle of plan your life and then let life kind of fill in the gaps. Right.

[Taylor]

And it does, it always does. You're busy, I'm busy. Like I. It's not a busy thing. You can still prioritize the things that matter.

[Host]

Yeah. Personally, and being able to see it on like one piece of paper. Like, what I loved about that first version that Jesse had folded up with the post it notes was you could see it all on a. On a piece of paper. What I hated was the post it notes always fell off and I was like, damn it, where was that? I can't remember. And so when you guys came out with the wall version, like, I adopted it immediately, but I was still that guy carrying around my desk calendar from FedEx. Like, I like being able to like write on stuff and move it around with you. Yeah. And so when you guys came out with the book, you know that, that book that people carry, that I carry around, it was like a game changer for me because I'm like, thank God I don't have to carry around this coffee stained FedEx calendar on the plane anymore.

[Taylor]

I mean, the planner that we made came out of because Jesse was also carrying around that same FedEx desktop calendar. Everywhere. Everywhere. And so the whole thing with the planner is it's a desktop calendar that folds up.

[Host]

Yeah.

[Taylor]

It literally is like, it's big.

[Host]

It's huge. And it still serves as like the big ass calendar. Like, it still serves as. You can see everything. I mean, I even track the heat cycle for the cows and when the calves are going to be born in my big ass calendar, like everything goes into it. And then like you said, you allow life to fall around the things you've intentionally planned because you don't go ahead and plan your meeting for October yet, but you know, the family vacation is going to look like, or you know, the hard thing you want to do. So put that on the calendar. And then when the meeting pops, they'll be like, Hey, I can't do that day because I got my kid's birthday or I got this trip or I got this event or I got this run. And I think, like, what you guys are doing with the calendar is even more important because you're creating community around it. What has community done for you in your life? Like, outside of just Jesse? Like, you must have been around community growing up.

[Taylor]

Yeah, I grew up in a place called Milford, Michigan. And it's. It was a very community oriented place. I had amazing friends and the community shows up for each other in big ways. So I guess that was my first. That was normal to me. And we do at the calendar and in the Jesse universe, bring together people who just want to have fun and enjoy their life. And we've created these systems, these methods around ways that we know work, like, so that makes sure that you always have something to look forward to, to make sure that you're shooting for a big enough goal. And I know you know this too. When you're around other people who have big goals, you make bigger goals and then you attract more people who are doing that. So it all feeds on itself. It's so important. You can't do these really hard things all the time in a silo. And you also won't be inspired or understand what's possible if you're operating alone. So.

[Host]

Well, it's. What's crazy to me is like you talk about doing hard things. You know, one of Jesse's things that he preached at that event that we've adopted in our life is this thing Kevin's rule, right? And there's this like mysterious creature, Kevin, who like randomly will pop up and randomly disappear. Like, this Kevin guy's a freak.

[Taylor]

Kevin's a freak.

[Host]

Like, Last man standing races 29 oh 29. Like, this guy is a freak.

[Taylor]

Yep. And he's so low key about it. So Kevin is. He's a cop. He lives in Long Island. Jesse met him on a run. Basically, they just hit it off and again, it's a snowball effect. Just started doing crazy things together. But Kevin's solo key. If you hung out with him, he's just the guy who's always down. You want to have a beer down, you want to go on a bike ride down. He's. You want to just like go on a walk and talk. He's down. He doesn't want to sit on a couch though, I'll tell you that. He wants to be doing things all the time. So when him and Jesse started being friends, they did this infamous trip to Mount Washington, which is on the east coast with their kids. And they did this overnight backpacking trip in the mountains. And I think people assume this about Jesse, but he doesn't camp a lot. Like he's not doing things like this is very out there for him. And they went up and they camped in the snow for the night and he just thought it was insane. And he goes, Kevin, how often do you do things like this? And Kevin said, oh, I do think I do a mini adventure every other month. I've been doing it since college. And he said he just breaks himself out of his routine. Whether it's a camping trip or the local polar plunge, or you go take an art class, or you do like a staycation. It can be a lot of money or it could be free, but the goal is to just always have something to look forward to and break you out of your routine. And it might sound so simple, but it may think about the last time you tried something new or put something on the calendar that you can look forward to that's not just like a big trip. These little things add up so much to just have day to day. They can be local to you. They could be like the dinner with a friend you haven't seen in a while, but putting on the calendar to make it happen. So that's Kevin's rule. And he lives it so hard. He does so many cool things in his life and also lives a very normal life, but makes such a priority to do cool things.

[Host]

Yeah. It's just six times a year. And like you said, a year. It's not. It doesn't have to be a ton of money.

[Taylor]

No. Or it could be, it could be a ski trip to Aspen or it could be on the 4th of July. There is like a local 5k and you just are going to do that, you know?

[Host]

Yeah. And I think a lot of times when, when I witness people trying to live life, they think they need permission from a financial perspective to go do cool things. But I mean, backpacking the Grand Canyon's not. I mean, getting there, sure it might be expensive, but your car is not ridiculously. Like there's always a way to do something.

[Taylor]

The first time I did the Grand Canyon, I drove there, I slept in my car. The toll trip probably cost 100 bucks for like, I mean, exactly.

[Host]

You found a way to disrupt the normal for not a lot of money

[Taylor]

and make like a lifetime memory. So. But we. That only happens if me and my friends look at our calendar and figure out what works for us to go do something and put it on it and train and prepare and whatever. Like, it still takes planning. And I. I'm a very spontaneous person and if anything, I'm more spontaneous than I've ever been because you just meet people and get invited to things and the more you do. But all of the best moments in my life over the past eight years have been planned. They've all been the most special. They've been events that I've prepared for, parties that I've planned for, races that I've trained for. Because it's the journey of getting to something that you care about and getting to look forward to something and then it like climaxing at the date. There's nothing like it. It's the best thing in the world. So I know after trying this for so long that that's not a coincidence.

[Host]

Gobundance is a community of over 800 high performers, entrepreneurs and investors with a combined net worth of over $5.7 billion. But look, it's not just about the money. We're about building lives of abundance. If you're ready for a tribe that challenges you to achieve a higher standard for yourself, visit gobundance.com tribe that's G O b u n d A N C E.com T R I B e to apply today. What's crazy is I think most people live their life saying, I have to be planned or I have to be spontaneous. And what you have done is said, I can be planned and still be spontaneous around the plan. Because you know, when the things are that you really want to do, they're booked, they're on the calendar, on your big ass calendar. And then you go build spontaneity around that.

[Taylor]

Yeah. And you meet more people and you get out of your house more and you're more energized because when you have things to look forward to, life's just way more fun. I think it just opens you up to more newness when you're doing more, when you have more planned newness and more newness comes into your life, period. Yeah. Versus waiting for some random invite to come out of nowhere, you know?

[Host]

Yeah. Like you said, you wanted somebody to create a flash mob and you're like, well, nobody's gonna do it, so why not me? Like, somebody's got to create this. And I mean, I think, like, it's just such a cool statement of it must have been partly how you were raised and partly how you're wired that you just are like, I don't care if I Look like a fool. I don't care if I look like a genius. I don't care if this crushes it. I don't care if it flops. I'm doing this for me.

[Taylor]

But I will be super clear. I still am very scared, and I still, like, sweat through my clothes before and feel anxious that nobody comes or that people think it's stupid or I get nervous around the events, but it's not enough to not try.

[Host]

Do you think you get nervous because you're afraid nobody will show up, or are you just nervous and an anxious person?

[Taylor]

I'm not a nervous, anxious person at all. I just want things to ultimately be fun and kind of I want my vision to come to life. And my vision is for people to show up to a flash mob, not be at a flash mob by myself. Right. If I'm gonna put effort into something, I want it to happen. So I feel that pressure, but I'm not an anxious person.

[Host]

Yeah. Because you're down here for south by Southwest in Austin, and you've planned this crazy no phone party. So is that something, like, you're nervous about?

[Taylor]

I feel pressure to give people a good time.

[Host]

You just want people to have fun?

[Taylor]

I just want people to have fun. So, yeah, like, there's some nerves around it because you can only control what you can control. But I think we've done a good job preparing for doing the best we can there. Am I gonna do some random stuff for the next 48 hours trying to make it even better? Yeah.

[Host]

Yeah. So what I hear you saying is, like, the pressure you feel is almost self created just because you care so much that people have fun.

[Taylor]

I care about everything that I do.

[Host]

Yeah. Always. Have you always been like that?

[Taylor]

Yeah. So I have to focus on how many things I'm doing because I don't do anything I don't care about. So the more I can focus down, the better.

[Host]

What would you say your superpower is?

[Taylor]

I think I'm really, really good at connecting with people, and I think that would be number one, because I think that's how I get people to come out to things. I think that's how people like to interact with me. Like, to be a part of whatever I'm doing. It comes down to just connecting. I'm very good at that.

[Host]

And is that your mom, your dad, or none of them?

[Taylor]

It's both of them.

[Host]

Both of them. Both of them are good connectors.

[Taylor]

Yep.

[Host]

Because you constantly, like, bring these different stories together in the world you're living. Like your mom and your dad are like a very big part of your life. Your sisters are a very big part of your life. Like, you're constantly bringing these little pieces in, but it seems like they're foundational pieces that are always there.

[Taylor]

Always there. They're always there.

[Host]

Like, you even got your dad to do marketing for the big ass calendar.

[Taylor]

Everyone's done marketing for the big ass calendar. Whether you've seen them or if they're behind the camera and I'm doing it, or they're holding scripts. My mom has done so much stuff, everyone's on board. But I would say when you ask about, are you anxious? Do you worry? Are you afraid of getting embarrassed? Because I've thought about this a lot. I've never seen my parents get embarrassed. I've never seen them care about things that I would say, frankly, don't matter. For example, they host a lot at their house and the house will be clean when everyone comes over. But my mom's not trying to be perfect. Like, our house was always the house all the kids were at and entertaining and no one was stressed. Like, it's okay that there's some mess. If, like the turkey lights on fire. No one's having a meltdown. It's ultimately about having fun. So I was raised in that same environment that I live in now. It's about like, what, what actually matters is the human connection. Making sure we have enough food to feed everybody so that they're happy, but not because we're putting on a show. They. They always. And they're not worry worriers. They're very solution oriented. They're never stressed, even in stressful situations. My family is going through some health problems right now and the attitude around it has been, well, this is a new experience. It's insane. Like, that's not coming from me, that's coming from them. But, you know, that's what I'm saying. It's like other times I think people would be having a hard time. And that's the attitude coming from the top in the family right now. I was like, this is a new experience.

[Host]

And that's kind of where you get it from. That's how you would look at it too.

[Taylor]

So, yeah, like the risk taking and stuff, it's just because nothing's that deep, I guess. And ultimately we have what matters. So they've been teaching that without trying to the whole time.

[Host]

Let's go back to this concept, though, of your life being a movie. So if that is true, what scenes are you most looking forward to? That have not yet been played.

[Taylor]

I think so far. It's just. I'm excited to see what can happen because I couldn't have written anything. That's what's funny about making goals is I do make goals, but then it's like, how do you make goals without limiting what's possible? So I'm just excited to see, like, how far I can take this, like, what mountains I can end up being on top of or what weird situations. I just want to, like, get into everything. Like, I want to do weird scuba diving trips, and I want to be doing, like, a sports game with one of the best in the world, you know, and just seeing what, like, side quests I can make happen and then the normal things, too. I think if you're talking about the full range of human experience, I want to meet a partner. I want to have a bunch of kids. I would love to have, like, a crazy farm like you have and just try all those different things. I've been so nomadic. It'd be cool to have a place to host people like Eric Hinman is. I feel like, in the Austin community is such a prototype for that. I want to do that, and I want to do it for women, not excluding men. But I think there's a lot of things in this space. This space meaning like, wellness culture, entrepreneurship, where it's so male heavy. And what I think the guys do. Right. Is the way they network and the way they do business is ultimately, in my experience, rooted in fun. Whether it's a golf trip or going to Eric's house or sonning, they're doing things. Even their dinners is to have fun first, and then you get to know each other and do business together later. And a lot of the women's groups I've been a part of or events, it's very like, this is a networking event, or we're learning. And I want to bring more fun to women. I want the women to have fun first and then do business later. And trying to feel. Trying to figure out what that looks like because I haven't found it yet myself.

[Host]

Yeah. Yeah. And as a father of two daughters, two girls, like, I want you to create that because I've seen it on the male side.

[Taylor]

Like you said, they're doing it very well. And again, it doesn't need to not include men.

[Host]

Right.

[Taylor]

But I want that to be more normalized. Yeah.

[Host]

And it's not from, like, a sexist perspective. It's just like, men coming together to do cool stuff, not because they don't like Women or not, because they don't deserve to be there. It's just a different conversation. And women doing women's stuff is just different. But the way that I think you could create it for the women, I think the world needs more of. And that's coming from a guy who's seen it on the men's side in a very big way. I was looking at my 6 year old and my 1 year old going like, I hope somebody creates this for you.

[Taylor]

Yeah. And I don't think I've been around a lot of men that they don't mean to exclude women. It's just like, if I'm going to go on a run, I'm going to call the guys or I'm going to go on a sauna, I'm going to call my guy friends. You know, they're not thinking about it. And I think the more I want to get into those rooms so then I can just bring women into the rooms. And I think that's a way to start. Yeah, right. So I know how to get into them because for some reason I keep being in these situations where I'm with like 10 dudes going across the US over and over again and like I'm with 10 guys in fit. Like, I'm with them all the time and I'm. And now it's up to me to bring the women in. And by the way, guys, like, you can invite girls to these things too. Like, I have some guy friends who said to me the other day, I have a friend, Cole in New York, and he puts on a lot of events and he was working with Ann who started Solidcore. Do you know?

[Host]

I know the name, but I don't know who she is.

[Taylor]

So he was saying that he was doing an event and he asked Ann to speak at it. And she's like, send me who's coming? Or like, who's speaking? And she goes, I don't want to do this event. There's no other women. And Cole told me it's not on purpose. I just didn't even think about it. And it's just thinking about it. And I think being in the room makes them think about it. Yeah, like, you know, it doesn't need to be forced. But that's something I'm looking forward to figuring out because fun is such a big part of my life and. And business, it's completely intertwined with business. Like the person doing my website I met in Asana and the person who helped me with like the staffing company, I'm Working everybody that I'm doing work with and have hired on our content team, We've run races together. That's how it starts.

[Host]

So, yeah, you build relationship through doing cool stuff. Having fun is like, well, what do you do? I build websites. Like, I need a website.

[Taylor]

Great. And I trust you. And, like, I would like to work with you because, you know, you're my friend. Why would I rather go to someone I don't know? So, yeah.

[Host]

So if you were giving advice to men myself, like, let's say you're looking me in the eye saying, like, hey, this is how you're going to. To help this movement, help this wave. How do men embrace that more besides, just think about it?

[Taylor]

I think even things like this, inviting me on your podcast and not because I'm a girl, just because you like me. And, like, if you know women who are building or are out there just inviting them to things, that's it. Like, it's so. It's such a simple thing to do. And just know that they want to be in the room, but I don't think they're asking enough yet or they're not going to force themselves into the room. So just creating an opportunity for them to be in those rooms that are already built.

[Host]

Yeah. I mean, this. This has been a really cool experience for me because I've admired what you've done from afar. Like, we were. My wife and I were, like, glued to our phones when you were crewing Kevin for his hundred mile run. Right. Like, we were following your story because you provided such a unique lens of, like, fun and humor, but there was, like, the heaviness of, like, holy shit, he's doing this hard thing. We haven't slept. I don't know how much longer he's going to go. Right? And so, like, for me, it was like, we've got to get Taylor on the podcast because I've admired how you lived a life. It doesn't matter if you're a man or a woman or identify as anything. Like, I don't care. I just want to be around people doing cool shit and living authentically. And I think you are one of the best examples of living authentically that I have seen.

[Taylor]

Thank you.

[Host]

And I've seen a lot of cool people, but. But most people live one way online and then a totally other way here. And I mean, we just did the. On the ranch and you did it in high heels.

[Taylor]

Like, they're kind of short, but.

[Host]

Yeah, but you're like, should I change? We're like, now you're like, okay, cool. I got it. Like, driving a tractor, feeding cows, holding puppies. Like, high heels. Like, that's just. You, like, yeah, cool. I can do it differently. I can. I can challenge the status quo. And I just. I admire people like you. Like, people like you go, like, I'm just gonna do what I want to do. I don't really care what the world says.

[Taylor]

Yeah.

[Host]

And so, like, for me, I totally can see what you're saying, though, because I've been in those rooms, too. Like, I've even, like, created some of them. Being the CEO of GoBundance, which is. Has a men's organization, has a women's organization. But most of the meetings that I run and facilitate are men. And I think there's power in that. Like, men talking to men can be a little bit more vulnerable. It's a little different conversation. But at the same time, there's a lot of really cool things that are going on that there's no reason women shouldn't be invited to.

[Taylor]

Totally. I believe men for men, women for women, too. And I think there's a lot of rooms that everyone would benefit in if there was both.

[Host]

Yeah, I totally agree.

[Taylor]

And again, like, I just know, like, funds the answer. So just finding ways to bring people together. My friend Ben invited me to this poker night the other day. I thought, for sure, we're new friends. I thought, for sure there's going to be other women there, because I just said. I was like, if I'm getting invited to a poker night that I don't know how to play poker, it's not. Like, I said, I'm going to come kick your ass or anything. Just. He's like, yeah, come to poker. And I walked in, and it was all these tech founders, and they were all guys. And I said, thanks for inviting me. Like, this was so fun, and it goes so far. And I don't think he has any idea how far that goes for me. Like, I was high on that experience for, like, weeks.

[Host]

Did you win?

[Taylor]

I. I came out up. Yeah. No, it was very exhilarating. I texted Jesse after. I was like, I know why people have gambling problems, because that was, like, too fun. I'm gonna get really good at poker now. But again, it's just. They had so much fun. I was like, this is so fun. Work didn't come up one time. And I know all those guys work together. You know what I mean? And they would make any call, and when anyone's trying to do any marketing or staffing or they're all calling each other, but work's not coming up at all at those things.

[Host]

Yeah, yeah. It's like you're living the life that I try to live, which is chasing return on joy, not return on investment.

[Taylor]

It comes back way better.

[Host]

Well, and I tell people all the time, like, go to a funeral and show me a U Haul. Following a hearse with everybody shit in it. The only thing following a hearse is the family and the friends that you made memories with along the way.

[Taylor]

Yeah.

[Host]

So why don't we just create more of those? Like, why don't we just chase those relentlessly? And yeah, business is gonna get sprinkled in along the way. But have business be the thing that fuels the joy, fuels the fun. Not have, you know, these things that we're chasing just so we have this next asset or this next watch or this next car. Like, it's all about joy. It's all about memories.

[Taylor]

It's about memories. And I also think in just a pure business sense, it's more sustainable to just start with the authentic connection. Because you don't. With no other motives. If you just get used to doing that all the time. So many people that I met when we had nothing or no momentum, we both have a lot of momentum in different areas. And now we're helping each other, but we already have this foundation, so we know we're not like using each other. And you can do so much more for each other if you have actual relationships.

[Host]

I totally agree. And if people listening to this now are like, man, I want to live like Taylor, I want to go buy the big ass calendar. I want to go try to run Hell on the Hill or 2902. Like how do people follow your journey and keep in touch with you?

[Taylor]

I'm Aylorprox on Instagram and then we're Hebigast Calendar, also on Instagram on all platforms. But Instagram's our biggest platform.

[Host]

Instagram's the biggest one. And if you could challenge people listening to this to do one thing different tomorrow, what would it be?

[Taylor]

If you haven't already? We didn't really get too deep into this, but I think the most life changing aspect around the calendar that we've seen from people talking to us for years now is the idea of the misogi. So that's what like your bike, I'm assuming is going to be. It's that year defining moment on your calendar. So if you haven't put something like that on your calendar, it doesn't matter. Like whatever time you're finding this podcast, think about something that would be so important to you or mean so much to you that at the end of the year when we're in December and you look back on 2026, you could say, I can't believe I did that this year. Or that meant so much that I did that this year and forever. You remember 2026 like that. I can do that for every year since I started implementing the idea of misogi, which is one year defining event. If you've never done one before, a physical challenge is a very easy way to do it. I say easy in quotes because you can sign up for a training plan. It just tells you what to do. Like you don't need to figure everything out on your own. There's so many resources. But I would put something on your calendar that's meaningful that maybe scares you a little bit, that can anchor your whole year around. Because if you do that every year, when you look back, when you're 50, 60, 70 years old, you'll have, you'll have 30 year defining experience. 40 year defining experiences. And that just leads to a richer life, a more intentional life. You draw really cool people around you because you're really leaning into your interests and your curiosities. But that's been the one of the most life changing things I've ever implemented in my life. And I know a lot of people feel like that.

[Host]

Yeah. And when I talk to people about that, they're like, well, what would I do? What would I do? I think you guys do an incredible job of like throwing out there what people are doing. So like, what's the coolest, craziest thing you've heard? And then what's like the simplest but yet cool thing? Because people think misogi, you're defining. It's going to be expensive, it's going to be really hard. It's going to take a really long time.

[Taylor]

But yeah, like you're. How long did you say your bike ride is going to take?

[Host]

Hopefully 13 days.

[Taylor]

Yeah. So raising a million dollars, 13 day bike ride across the United States. Obviously they making a YouTube video every day about it. Like lots of time, resources. So 150 miles a day on a bike is no joke.

[Host]

Yeah. Just to be clear, Taylor said I will fail. Like I'm gonna look at the calendar and say Taylor said without words, but with her eyes and her body action, like there is no chance you complete.

[Taylor]

No, I said with my eyes and my body that I cannot wait to tune in. Like this is gonna be Entertaining and watch you fail for sure. I can't wait to show up for a little bit of it. I would. You're. What was the question?

[Host]

What's the cool. Like, what are some cool ones that you see examples of?

[Taylor]

So some examples like I have a friend who got their pilot's license. Obviously that also takes time and money. But this is the thing, I'm not going to tell you anything that doesn't take time or money. Mistokes require sacrifice. There's no such thing as an easy misogy. Okay. Like if you want to throw a lot of money at it or not, that's up to you. If you want to run a marathon, you can sign up for a marathon, buy the nicest shoes, hire a coach, join a gym, or you can plot something out on Strava and run it. And what you know, you can spend a lot of money or no money. Yeah, a marathon's really hard for some people and it's really easy for other people. So it's what's relative to you just pick something that's hard to you, but don't look for something that's easy and you can just do tomorrow some cool things. So we had this guy come to our house, to Jesse's house to film a YouTube video the other day and he said that the physical masogis haven't resonated with him very much. So he was really trying to think of something he could do. And he said he took six months. And by the way, he's 38 years old and have never played the piano before. He took six months of lessons to learn one song and can read music now and can play the piano now. But he showed up and he said that learning this song was my misogi. And he played. I grew up with a piano and like love piano bars, by the way, the most beautiful song I've heard on the piano in my life. Like me and Jesse were bawling, crying, and then we got Sarah and brought her downstairs bald cried. It was crazy to see someone who's had no instrument background pick up a song by pickup, work really hard. He was like, I was walking into these classes with my music book and six year olds were walking out and I was walking in to see my piano teacher again. Like some people might think that's embarrassing or I don't think a lot of 38 year olds are like, I'm just gonna pick up piano. But it just shows like anything is possible. So what is that to you? Have you always wanted to play the guitar? I have a friend who just did a live comedy show. He said he's always wanted to do it, and he signed up for a class and went for three months and then performed stand up comedy like this looks so different to everybody else. But I think if you spend any alone time with yourself, off your phone, going on any walks, and actually think about things that move the needle for you, you'll. You'll have some underlying idea of what that is.

[Host]

Well, and what you said was gold is like, if it's worthwhile, it will take time or it will take money or both. Yeah, but like, anything worthwhile is going to take time.

[Taylor]

Right. And don't be afraid to commit to something. Like, the payoff is so worth the commitment.

[Host]

Yeah.

[Taylor]

I think people are so afraid of commitment for some reason and saying no to what they're used to, whether that's going to happy hour every night or whatever. Like, listen, I love going out, but I also love locking in sometimes. So I can do something really sick, right? Yeah, you can have different periods of time. Oh, my God, the dress with it.

[Host]

Can you say hi?

[Taylor]

Can you say hi to Ms. Taylor?

[Host]

So she takes her four wheeler down to the gate and checks the mail every time she comes here.

[Taylor]

Wow, those are really good outfits.

[Host]

What do you say? All right, we'll be out a minute. Okay. Ry. And I think what's really cool is, like, you said, you have to put a flag in the ground and commit to it. Like, when I committed to this bike ride, I didn't even get on the bike before I committed to it. I just started talking about. I'm like, this is what I'm gonna do. And I literally had people. And I've kept this in my journal. I call it my receipts. I've had people call and tell me how terrible of an idea it was, how I'm doing it all wrong. And my first question is, like, so tell me how you did it when you rode across America.

[Taylor]

Right?

[Host]

Well, no, I've never done that. Like, I had a guy literally call me and say, like, I'm gonna give you advice. I'm like, okay, did I ask for this advice? No. Okay, cool.

[Taylor]

Have you done this before?

[Host]

Yeah, continue. He's like, my wife and I were talking and we both think it's a terrible idea. I was like, okay, cool. Thanks for letting me know. He's like, the amount you're gonna have to sacrifice, the amount your family's gonna suffer, the amount work's gonna suffer, the amount your body's gonna suffer, it's not worth it. You shouldn't do this. I was like, okay, cool. Thanks so much. Hung up the phone, wrote all of that in my journal, and I'm taking that journal with me on the ride. So, like, when it sucks, I'm gonna pull that out and be like, okay, this date, this person said, this thing

[Taylor]

you love operating on bite.

[Host]

I love. I love. I love, like, having a chip on my shoulder. Like, people.

[Taylor]

Jesse always says that, too. He's like, no, I want the chip on my shoulder.

[Host]

I want people to think I'll fail. Like, I want people to look at me and say, he's a college dropout. He'll never make it. Like, I. I want to be able to prove to people that ordinary people can do whatever they put their mind to.

[Taylor]

But you know what? No person who's done that has called you and told you not to do it. Anyone who has suffered or done something really dumb or it went really wrong. None of them, even when it goes wrong, are never the people calling you not to do it because you're like, he's going to be fine.

[Host]

Well, it's. I mean, I talked to Jesse about it, and he's ridden his bike across America.

[Taylor]

Yeah.

[Host]

And he didn't say, bad idea.

[Taylor]

No.

[Host]

He didn't say, why are you starting in May at the end of May in South Texas? Like, he just said, that's dope, man. That's so cool.

[Taylor]

And no one who does hard things will ever, like, no one who's done it will ever tell you otherwise. Even if it was a disaster for them, because they just realized it's not. Again, not that deep.

[Host]

Like, and it's.

[Taylor]

Why wouldn't you just try?

[Host]

It's all about who you become on the journey of life. And I think, like, what you said is so important. Like, just commit to something. Commit to something that's going to define you. You're playing the piano, running a marathon, running a 5K, becoming a chef, learning how to make sourdough, which is like this new fad. I mean, mahjong. My wife's big into this mahjong world that's going crazy.

[Taylor]

I'm trying to get someone to invite me to one of these.

[Host]

Oh, my gosh. Well, we have. My wife started a mahjong company. We have tiles. You can have a set of tiles.

[Taylor]

Amazing.

[Host]

She's a mahjong lady now. But do something that's different than what you would usually do and meaningful to

[Taylor]

you and don't compare it to anybody else. It could be.

[Host]

That's the big yeah, that's the big thing. And then put it on that big ass calendar with beautiful stars and exclamation marks and look forward to it, train, stay committed to it, whatever, tell people.

[Taylor]

I think people like to listen. I love who this works for. And I know it works for some people to like, what's it called? Move in silence. Yeah, but I don't do well moving in silence. I have to move in by telling everybody. I want like public accountability for anything that I'm doing. Also, I get really energized by it when people are asking about it, I get to talk about it. A byproduct of doing something big and committing to something is when people ask you, what's going on? What's new? How are you? You don't say nothing. Like, nothing. In quotes you say, oh, I'm learning how to swim or oh my God, my balls are chafed so bad because I just ran. Did 200 mile bike rides back to back weekends for the first time. Like, I'm so messed up. You won't have a boring conversation for the period of time you're training because you are always learning something. You're always experiencing something new, meeting people that are new. So you become a way more interesting person when you're learning and doing something for yourself. Like, my least favorite thing is that people feel obligated or it's a social norm to just say the word nothing back. Like, tell me what you're up to. Like, tell me what you're excited about. Like, I want to get to know you. We're talking to each other and I think when you have a masochi on your calendar, you have something to talk about the entire time.

[Host]

And like you said, the public accountability. I think the hardest thing for people to do is keep their word with themselves in private or silence.

[Taylor]

Yeah, no, I'm like, tell everyone. Like tell the world everyone.

[Host]

Yeah, as soon as the bike rides over, I actually have to ride one of those stick ponies. Have you seen this? Like there's like stick pony competitions where you like ride a fake pony and go over these jumps.

[Taylor]

Yes, I've really seen it because I made a video a long time ago of me doing it. So people send that to me all the time.

[Host]

So I said if I didn't finish the 100 mile race, which I quit at mile 41, that I would go into a stick pony competition. So as soon as the bike rides over, I'm going to learn how to jump a jump on a stick pony.

[Taylor]

That's a brutal Punishment, Honestly. That's so funny.

[Host]

I mean, it's fun.

[Taylor]

No, it's. It's fun, but, like, you also don't want to do it, I'm sure.

[Host]

No, I have no desire to be on a stick pony.

[Taylor]

Like, what's the worst thing I can think of? I'm never gonna quit the hundred and

[Host]

people are sending me videos. People take this shit serious.

[Taylor]

Seriously. No, people are really, like.

[Host]

I mean, like, their stick pony is a real pony. Like, like, it's. It's a thing. So.

[Taylor]

I know. I know more than you would think about that specific subject.

[Host]

Well, I'm calling you for training. Like, all right, Taylor, I need a trainer to help me with the World Championships stick pony jumping competition. But I think talking about it, telling people what you're up to, like, you said, A, to be interesting so that people can be interested and maybe give themselves permission to go do something sweet. But B, for that accountability, like, when you. When you talk about something, it becomes real inside of you. Your subconscious mind goes like, oh, shit, I'm talking about this bike ride. I mean, when I started talking about the bike ride, one of the first people I told about it was like, when was the last time you rode a bike? I'm like, ah, about 18 months ago. He's like, oh, that's cool. What kind of bike do you have? I'm like, I don't know, but it's white. He's like, send me a picture when you get home.

[Taylor]

I white and it's heavy.

[Host]

Turns out the bike was black. Never realized that, like, didn't even know what color the bike was, but it was about, like, this is what I'm up to. And what's cool is when you talk about it, like, the craziest people show up. Like, this guy I was talking to turned out to be a bike tech all through college. So he's now become somebody that's giving me a ton of advice because he's like, what are you working on? I'm like, riding my bike while tanging on the wall. But I'm going to ride it.

[Taylor]

I put out that I really want to dive with whales this year. And the amount of people that I don't know that send me different places to see whales, different whale videos, want to plan trips together. It's just if you want to connect with people, do stuff. And I get asked all the time, how did you find out about this next thing? It's because I told everybody about this one thing, and then strangers, new friends, tell me about the next thing. I should do. And you just get flooded when you put things out there because they think of you. It's like when someone has a good personal brand. If you're always wearing a blue hat and people start thinking about you when they see blue hats. Same thing. Anything that you put out there, anytime they hear about or watch a documentary about people going across the United States or doing something really hard, or they're gonna think of you and they're gonna send it to you, and it gives people a reason to connect with you.

[Host]

Yeah. And, like, when you talk about stuff, I swear, the world, like, conspires to help you. Like, it all collides and is like, hey, Taylor's gonna go do this crazy flash mob. Let's put this Alfredo or Alfonso guy in her path, and give him a speaker, and he'll show up like. Like, God, the universe, like, whatever you want to label it.

[Taylor]

Yeah.

[Host]

I swear, the world just wants to reward people, like, living, like, actually doing life. And. And then when you talk about it, cool people show up that are like, hey, this is how I trained. Hey, this is what I did. Hey, let me connect you to my friend who is the producer for Mr. Beast, who can help you guys think through how to produce this.

[Taylor]

Like, oh, this is my favorite thing I ate during it. I could keep these down. After three days when you don't want to eat anymore. It's just, like, why I think it's so fun to put things out there because you get. Get cool things back, but you also get the hate. But who cares?

[Host]

I mean, the hate. The hate is a sign that you're doing things right. That's my.

[Taylor]

Or you're giving people something to talk about at dinner. I guess.

[Host]

Yeah. I mean, I've gotten some messages, and I'm sure you've gotten exponentially more where I'm. Like, you literally took time out of your day to send me this. Like, I'm almost flattered that you were watching me, sent me this, and, like, thought that it would carry weight for me. Like, I'm flattered.

[Taylor]

You know what, though? I. I haven't had that yet.

[Host]

Good.

[Taylor]

The people. I've had nothing. But some people go, I can't believe you're doing that. But I can't wait to see what happens. Like, I have a lot of. Really. People have been really positive towards me.

[Host]

Yeah. The hate I get is, like, the other day, I posted a video of, like, hanging my. I rode for three hours, and so my bibs were, like, soaked. Like, it was disgusting. And I was like, I should just put a glove on and carry these things. Like, these things are nasty. I'm like, I'm just gonna make a video. And the guy's like, a guy kind of was like, it's your own sweat, bro. Don't be a bitch. I'm like, dude, it was just kind of for fun. Like, it was kind of like, this is disgusting.

[Taylor]

Like, I block those people.

[Host]

I just enjoy it. I'm like, really, dude, you should come check it out yourself.

[Taylor]

I'm in a bubble of positivity, and I'm an excuse.

[Host]

That's the way to live. Whatever you're doing, my only encouragement to you, not that you need my encouragement, is just keep doing it like, people are watching you. People are inspired by you. People feel motivated by you. My wife talks about you. Her friends talk about you. I talk about you. Like, your life is living proof that you can do whatever the fuck you want. And I just want to thank you for living that way. The world needs more of it.

[Taylor]

That means a lot. It.