What It Really Takes To Bet On Yourself, Build Community, and Grow in Endurance Sports with Jonathan Levitt

Welcome to the Everyday Ultra Podcast, a show designed to help you level up your training,

crush your races, and ultimately become a veteran endurance athlete every single day.

Whether you're an endurance athlete as a hobby or someone who wants to be the best in

the sport, this is the show for you.

I'm your host, Joe Corseon, and thank you so much for listening.

Now, let's get into it.

Once up, everybody, welcome to another episode of the Everyday Ultra Podcast.

I'm your host, Joe Corseon, and super excited for this episode, because we're bringing

back John Levitt to the Everyday Ultra Podcast.

John has been on the show many, many times.

He's a good friend of mine.

He's the host of the four-the-long run podcast.

And in this episode, we sit down with John, and he talks about what it really takes to

bet on yourself, how to find community in trail running, and how can you grow as not

only an endurance athlete, but as a person.

And there's a lot of really, really great lessons from running, from life in here, that

I think you're going to take away a lot of great things to bet on yourself more as you

align towards your big ultra marathon goals.

Also, I want to give a heads up as well to you.

This episode is actually hosted by my amazing colleague, friend, and fellow Everyday Ultra

Coach, Alyssa Clark.

She is on the other side of the mic at this episode.

So if you don't hear me in there, I'm just know you will hear the amazing Alyssa Clark

navigating the episode for you.

So excited to end this episode, before we do one quick thing.

Hey, everybody.

Before we end this episode, I need to address a question that I could ask a ton, which

is, how do you prepare to go number two when you're out there in the middle of race on your

training run or on the trails where there's no bathroom in sight?

And my piece of advice is always be prepared.

So for me, what I do when I'm out there is I always take wipes with me.

And not just any other wipes, I use specifically bare butt wipes.

Now, bare butt wipes is individually wrapped, eco-friendly wipes that you can use on the

go out there.

And they come in these really, really easy to carry pouches that do not weigh you down.

And they're easily stuffable in a vest or in a running belt out there.

And they have very good on the go convenience out there too.

It's also made with biosegradable and eco-friendly.

So they're very, very friendly to the environment as well.

And if you're out there in the bathroom, it's they're flushable and septic safe as well

too.

It's just your thick and durable for outdoor use.

So you really only need one to get the job out there.

So you don't need to take on tons of different things.

And also they are fragrance-free and made with really clean ingredients.

So they can be very, very sensitive to your skin out there, which is very, very good for

an ultra-entry outrunner as well too.

So if you want to get bare butt wipes, try highly suggest it.

I use them and I take them out on every single run even when I don't need them.

And when I do need them, I thank myself for taking them out there just in case they're

super affordable too.

You can get up to 30 individually wrapped wipes for only 10 bucks.

And guess what?

You can even get a 10% discount just by listening to this podcast when you go to barebutwipes.com

and use code EverDulchera for 10% off your order.

That's barebutwipes.com and use code EverDulchera for 10% off your order.

That way you can be be prepared on your runs, encase nature calls, and you can make sure

that you don't poop your pants out there.

All right, everyone.

Give me a try.

Thanks so much for listening and let's dive back in the episode.

What's up, everybody?

Welcome to the EverDulchera podcast.

I am joined by a familiar voice.

We have Jonathan Levitt on the podcast today.

He is the host of the For the Long Run podcast as well as his newer edition Long Run Labs.

He's a long time runner, very well known in the running world.

Has a lot of new exciting endeavors that I think we can definitely get into.

First of all, Jonathan, thanks so much for being on and what were you up to this morning?

Listen, thanks for having me back.

I love this podcast.

I tell Joe every time I listen to it, this show makes me want to run through the wall with

motivation.

I texted him that a handful of times while listening to it.

You guys do a fantastic job and it's an honor to be back on here.

What was I doing this morning?

Same thing we do every day, Pinky.

We were running the burrito league in Boulder.

I don't know, like three miles there, three miles over there on a 0.2 mile lap.

I run there at the back, so it's a five mile minimum commitment and then, yeah, it ate

mild run today, so I did a few over there.

Yeah, maybe your listeners have, yeah, so Boulder League or burrito league in general,

just listening to the Boulder Boys show talk through it and Adam did a fantastic job

of explaining it.

And it's essentially the evolution of what existed last year with the Chipotle challenge

where people were running crazy amounts of miles in front of Chipotle's nationwide.

And this year, Chipotle for some reason didn't choose to do it again.

So Jamil Curry said, we're doing it again and just started doing it out in Arizona and

it's happening in a bunch of other cities.

And the idea is you run a 0.2 mile lap as many times as you can in a three week period.

And the person who has the most laps wins a burrito for a year.

So here in Boulder Scratch Labs Cafe has a wonderful burrito and they're a supporter

of the one that's happening here.

There are local burrito shops contributing in other places.

There's some shoe brands that have been contributing and John G is contributing in Boston.

So it's cool.

It's a cool community effort where it's getting people to do more than they would otherwise.

And I've been talking to a handful of people here in Boulder and some people are doing

it just for the community vibes.

And as a way to meet people, talking to one woman who's actually leading and her name

is Kelsey.

And she's like, despite growing up in Boulder and living here and running competitively

for a while, like she doesn't have a big running community.

And so she goes to runners-ers every morning for between two and four hours and gets to meet

people.

And she's, I've run with her four times now.

And I'm sure there are people there that she's run with 10 times now.

And so it's like a fast track to meet some new running friends because you're out there

doing this lap in a parking lot, effectively, stirring up mountains.

And yeah, it's really cool.

And then a handful of personalities have gotten involved in each city and a couple of brands

have gotten involved.

And it's one of those things that's like really cool in the way that it's not super commercialized

and very grassroots.

I love that.

That's such a great description of it.

It is all over the US.

It's actually made it out of the US.

It's worldwide now.

I see it in many ways as I have heard, of course, I can't speak for Jamil, but that he's

very interested in bringing the idea of kind of that six day walking, running event that

we used to see in, I believe, 1800s come back to fresh and I mean, we're seeing it in

the 200-mile distance and I see this is kind of a little bit of an extension of that.

Obviously, he was very a part of the movement last year.

I'm shocked to pull him dropped out of it.

I actually know that they weren't involved anymore.

But I'm curious.

I'm curious.

See, it's incredible earned marketing for them and they're getting so much benefit this

year at let, let, let, they're not even doing anything.

Yeah.

We're talking about Chipotle right now.

We are.

Well, that's actually something I want to ask you because you have, I mean, I would say

and correct me if I'm wrong in your space, you're very thoughtful about marketing that

you make a lot of brand connections in the running world.

Where do you see this being an opportunity for businesses to come in?

So I think there are a handful of different ways where it can work.

I think of running partnerships or partnerships in running in two buckets, endemic.

So shoes, apparel, nutrition, watches, things you need to like do the thing and nonendemic,

which is all the, all the other things that we as runners need, but we need them because

we're humans, not because we're, we're runners, we're humans who run.

So like kitchen appliances and cars and airplanes and all these things that like Chipotle,

yeah, food that's not like in gel for the simple carbohydrate form.

And so I think there's like an obvious like category for each, for each city, like a

watch, a shoe brand, something like that that is helping, sorry, there's a very low-flying

helicopter going over my house, so I was looking at that.

There's, there's, there are these boxes to check that are just like, it just makes sense.

We should have a watch company involved.

Amaze Fit is probably giving some watches here in Boulder.

I'm also working on that.

I'm, I'm tapping into that and I'm like, hey guys, hello, yeah.

And then shoes make a lot of sense, particularly shoes that are like ultra folk, like Mount

to coast, it made sense for them to jump in because that shoe was designed for road ultra,

right?

If you're gonna, so if you have a way to, to manifest the like best use case of your product

and it's in something silly like this, you should definitely be involved.

And then there's all the other stuff that like helps, helps the thing happen.

So recovery products, I was joking, I'm working on a partnership with a dairy company called

Pioneer Pastures and they make A2 Milk and the A2 Milk is easier on the gut effectively.

And I was joking, like, so they're trying to find all these like things to fill time,

right?

So how do you, how do you get someone excited for a certain hour?

How do you get people motivated who are not atop the leaderboard?

Well, most laps in this hour or fastest lap or slowest lap or, I don't know, it's like

random eccentric ideas.

What if there's like a, like a milk mile or something like that?

And so you, so maybe it's a stretch, but a company like that, their thought is, hey, we're

easier on the gut and easier to digest, well, try it while running, right?

Like people drinking milk in, in ultra's, why not, why not this milk?

So like, again, if there's like a way to manifest or demonstrate why your product works in

something like this, whether it's in the doing of the thing, the recovering from the thing,

or just like being out there, that makes a lot of sense.

And then obviously the tie into the local, the local community.

So in Boulder, it's outside of Runner's Ruse.

It's also outside of a Mexican place, a Mexican chain called illegal peets, I don't

know if it's like proper Mexican or just Americanized Mexican, but whatever it is.

And it's next to a brewery called Southern Sun and Whole Foods is there.

So like, what are the opportunities for brands like that that are physically in the space

to participate?

There should be an arch that is branded by a footwear sponsor, I don't know, something

like that.

Or you know, you can, as the shoe, as the shoe reads at the running retailer, like they

could be doing shoe demos every day.

And what better way to try out a pair of shoes than go run a single lap in them, or

try out a new pair of sunglasses, or try out shocks, I'm doing a like a live podcast,

like many recording over there tomorrow.

And with that, I'm giving away some products from my brand partners.

And so I'm bringing shocks, headphones, and people are out there at night, and it's

in traffic.

So the like the validation or the use case there is, you can hear your surroundings.

Of course, it makes sense to have shocks versus air pods for a use case like that.

So again, it's like matching the activity with the brands and services that help make

that either more enjoyable, more fun or safer.

I love that.

It's also, it's so accessible.

It almost feels like we're going back to the times of COVID where people were doing

challenges, you know, the four by four by four eight.

The backyard ultra is that you can do from your home, you know, just this accessibility

that I think with the explosion of popularity and racing can feel a lot more closed off

where it's like, I've got to get into these races.

I can't or it's going to take me 10 years to get into them.

So I love that there is an accessibility element to it.

And it's so interesting.

You brought up the idea of how do you keep people engaged?

So I did this event called last year standing, which is essentially a last or like a backyard

ultra, but for uphill ski touring.

And so you do a thousand foot lap every hour on the hour at a local ski resort.

And they would do like, okay, here's a hundred dollar lap here, whoever wins this gets

a prize.

So they would throw in things to make it interesting.

So I do love that idea of engagement in like a milk lap or, you know, fastest lap gets

a pair of shocks.

I think there's so much opportunity.

Yeah, otherwise it's just like, so listening to the Boulder Boys podcast and Adam was like,

I tuned into the live stream.

I was like, there's five hundred and eight more hours left.

Like, how do you, how do you fill that time?

And so like you, you have to fill the time.

It's like, oh, it's Tuesday.

It's Wednesday.

It's Thursday.

And so here in Boulder, they've done like different theme days or costumes or different

run clubs or like I'm coming and doing little mini interviews kind of a thing.

So yeah, got to keep it, got to keep it interesting and spicy.

Do you think that this has staying power?

Or do you think I think I think the beauty of something like this is it's so novel.

And like if you open YouTube right now, I'm almost certain you'll see something that's

burrito league.

And there's like a virality from the novelty of it.

And I think that wears off eventually.

I think the three week window each year is like, it's long enough for people to start

realizing what's happening and then it's over.

It's not too long.

It's not too short for people not to notice or understand it.

Yeah, I don't know if it like the longer it goes on years wise, the more corporate, I imagine

it would become and the more the less grassroots it becomes and you have brands like putting

together business plans of how to get involved instead of the scrappy brands that can move

on a dime.

And like there's, I love the brands that can just make a decision and decide to support

something.

And I like supporting those brands.

And when there when you have, you know, 49 weeks lead time, you don't get as many great

creative ideas.

I think like the urgency forces creativity and it forces or it bubbles up the like the

interesting stuff from interesting people who aren't just like looking to make a buck

and capitalize on momentum.

So I don't know.

I like it.

I think it will stay.

I just think it'll get a little watered down over time because of the capitalistic nature

of where we are in the world in 2020.

I love capitalism and the creativity will either go in one direction or like it'll either

explode with creativity in the 49 week lead time will be a wonderful thing or it'll start

to feel like way too corporate and branded.

Yeah.

I also wonder to, I mean, I think we saw, gosh, I'm trying to, maybe that was five, four

or five years ago where, I mean, backyard ultras were the rage, like everyone was kind

of focusing on that.

Like, gosh, this is going to be the next thing and they, they're still around, but I do

think that they have decreased in, we'll say, volume.

And so I always wonder with these kind of very long events if people just get to the point

where it's like, well, this isn't really sustainable for say a normal training schedule

or it becomes so embedded in the culture of the race year.

It's like, well, in January, we do our base miles doing breed a week.

Well, that's the, yeah, that's the thing like some people are out there putting up twice

their weekly mileage.

And like for, for one or two weeks, you can, you can do that maybe if you're not injury

prone, but you can't do that for three weeks.

And they're, they're people who I was talking to guy this morning, Sean and he was telling

me he normally runs between 40 and 70 miles a week and he ran 105 in the first week.

And he never, I don't think he'd ever run that many miles.

And there, there's another person that's running 100 miles a week.

And these are just like, and they're running 10 minute miles.

And so the majority of people that are running 100 mile weeks are probably averaging 715

to 730.

And so that's 25% slower.

That's way more time on feet.

Is that a good thing?

I mean, if you ask, if you ask my coach, David, like he'll tell you that slow running

makes for slow runners.

And you got to like figure out how to, how to maintain some turnover.

And so you don't just like come out of January, just like broken.

I think that's the concern.

I know there's kind of this joke of like,

coaches talking about burrito league and then the athletes being like,

this is so great.

The coaches are like, okay, but maybe we shouldn't do this.

Yeah, I don't know.

I think it'll be interesting to see how it shakes out.

I think it, it'll be, this is a time of the year where a lot of people are working on

speed work.

They're trying to do, you know, in terms of specificity.

This is when we're least specific.

We're working on perhaps VO2 max intervals.

And then we're building into something.

So it's definitely a different twist on base building.

We'll say, um, yeah, I'm curious to look out.

Thanks for entertaining my, yeah, my questions and thoughts on that.

But I want to get into.

So said last time you've been on the podcast was December 24, 24.

You've had a lot of life changes happen since then.

Can you tell us what that is looked like and also what I guess gave you the confidence

and the encouragement to step away from probably a guarantee into a pretty big unknown.

Yeah, so I spent the last 10 and a half years at inside tracker.

And I watched that company grow from, I was eighth employee and we peaked at 130.

We went from not very much in sales to tens of millions.

And so things changed over time.

It was like a masterclass in learning how to build a brand.

And how things go from like a, a very early stage start up to a not mature company,

but a serious company with, with big goals and big revenues and big line item costs with 130 employees.

At the same time, I was building my own podcast ever since 2019, 2019, yeah.

400 episodes in now.

And I got to be a lot of interesting people.

I started to get more interested in the entrepreneur.

I mean, I've always been interested in entrepreneurship.

But I started having conversations with people who had taken a leap and bet on themselves

and, you know, done their own thing.

And so, you know, working in effectively tech was an app working in tech

is never a guarantee, but it often pays well.

And so I went from pretty good pay for a long period of time to decide, like,

starting to think that I wanted to make a change and bet on myself and work for myself.

It took me like two or three years from when I first started thinking about that to actually taking the leap.

And so, at a conversation with my friend, Tony, who listeners may know as Tony with a Sony,

in July of 2023, where Tony talked through leaving his software development career,

becoming a photographer and, like, you know, conventional concept of software engineers,

software developers make lots of money and photographers don't.

And he was like, at some point, the cost of not leaving will be higher than the cost of leaving.

And I was like, I don't understand what that means, Tony of July of 2023.

He's like, you'll figure it out eventually.

And when it's time, you'll know.

And that apex occurred at some point in early 2025.

And the prior three years, I had done six figures in revenue for my podcast

as like a side business.

And I was spending 20% of my time on it.

And my weeks were very full.

So I was like full-time job and doing a few hours of this podcast on the side.

The expenses were high with the two because I was paying a handful of people to, like, do the thing

instead of spending all of my time on it, which I could not afford.

I couldn't afford the time.

So I had three years of data to say, well, if I spend a little bit of time on this,

I can make a bunch of money.

What if I spent more time on it and put more effort into it?

Can it become full-time?

And so I had this thought that like, if I spent more time on brand partnerships,

I could make enough money to pay my bills.

And maybe I'd make less, but I'd have a better quality of life and I'd have control over my schedule.

And to me, wealth is freedom and the ability to decide what you want to do when.

To me, that's what making money is all about, like getting to a place where I can block my calendar

for six hours in a day or a half day.

Like I'm doing next week and going to visit my grandma in Florida or go to BAMF with my girlfriend for a birthday.

And not worry about the fact that I'm not online.

And I personally have a lot of work to do to feel okay with doing that, but I can do it.

Which is a whole other story.

So I quit my job in June in May.

I told my friend Vivek, who I was planning to stay with at Western States.

He is a house in Truckee and I was planning to stay there for a week.

And I said, Vivek, do not let me in your house unless I've quit my job.

And I had a plane ticket and I said to him, I was like, I must step on this plane having quit my job.

And I texted my group of friends from San Francisco, David, Tony and Vivek.

And I was like, guys, do not let me in the house unless I've quit my job.

So I had this forcing function of something that I had been thinking about doing for a long time.

Long story short, I did it and I showed up in Tahoe.

Working for myself and the timing of that was incredible because I had just made this LinkedIn post and everyone was like, hey, what are you doing?

You just you left this tech tech job that appears to be so good and you're going all in a podcasting.

And yeah, I did.

And it quickly evolved into working with a couple of other podcasts that.

Wanted some help with partnerships and some of them had been like, I'd given them some guidance along the over the years or I'd help them make connections with brands and gotten them some deals and whatnot.

And they're like, would you help us with this? And so, so I started making deals for them and like very quickly I was like forking over tens of thousands of dollars.

To these podcast hosts that are our full time hosts and running coaches.

And that's how they pay their bills. And so for me, I love what running media has become. I love the fact that you guys have a whole operation and hundreds of athletes and races and fin has his whole operation and like a couple of races now and all this media and all these different properties are able to make.

Make a living in it. And so I've seen what happens on both sides of the table. I've been on the creator side. I've been on the brand side. I've like in a week watch to half a million dollars, you know, go back and forth between each other. That's not an exaggeration that happened in 2024.

I like made these connections and ultimately it led to to that much. I was like, I wonder if I can actually make a career of this.

And I was effectively naming like an agency model for an agent model where you are brokering partnerships between two entities.

And so I started with this idea of like a collective and very quickly I had 10 shows and then I had 20 shows and then I had 25 and now I'm at like 30.

And I've repositioned the thinking to be not this is not a podcast collective, which is like a fun networking type vibe to this is an agency that helps brands connect with their desired audience and high trust manner with podcasts being a vehicle to help do that.

Ultimately, I care most about the sustainability of this medium because you guys have thousands of listeners that tune in and enjoy what you're here what they're hearing from from you on a weekly basis and you have one of the largest shows in running in trail running.

So hello listeners. Thanks. Glad you're here. You make the world's all around.

Yeah, good job Joe on that Joe is the one who I got to come in when it was already very well established.

Totally. He's he's done tremendous work and he does even it's so funny. I feel like he does even realize.

I don't think he I don't think he realizes because it's just like he he just loves it and he's so he's so good at it. Right. And like I said, I have texted three times while running.

And I can remember where I am like dude like you're I'm so amped up right now your podcast is incredible.

So ultimately I love listening to podcasts and I am I have invested interest for the long term durability at success of this medium.

So how do I how do I create an insurance policy to make sure that it continues.

Okay, I can help fund it. I'm not writing checks, but I can I can connect podcasts with brands to help write the checks and and match hosts with organic and authentic relationships.

So for example, everyday ultra uses training peaks. I was in touch with training peaks and training peaks wanted to work with a bunch of podcasts.

So I found three shows that use training peaks and this is an organic relationship and it's not there's no stretch made.

It's just leveraging something that already exists in the everyday ultra ecosystem and formalizing a way to talk about it and then getting paid for doing so.

And the the the audience benefits because they get a discount or they learn something or you know they they're able to look at their training in a more effective or efficient manner, even if they're not coached by you guys.

So I started doing this and it started working and I so I created 100 K and deals in 2025.

I said, I want to make a million dollars of deals in 2026.

This week alone I booked 65 K and it's looking to be a 75 K week.

Everyday ultra will be introducing a new sponsor due to one of those deals that was booked this week.

And it's something that's it's effective that will be a useful training tool for for the the I don't want to ruin the surprise, but it's an exciting one and

I love that we can we can do this and we're doing it in both running with running brands are talking about before and the non running brand so I think about like a rocket money.

Rocket money is a financial services app that helps people cancel or reduce the cost of subscriptions doesn't help you run better doesn't help you do anything as it relates to run better except maybe have more money to buy running stuff.

But rocket money, for example, understands that the audience is of a show like this or any show in running is a perfect overlap with their their ideal customer.

So millennial excuse female high house income on average and interested in like quality and control.

So if you have something that's a tech platform that helps you reduce spend on in your life, of course it makes sense to to promote it like I've literally saved hundreds of dollars of my own money and why would I not want to partner with that again it doesn't help me run better.

It's not taking a category of a watch issue apparel nutrition and so it's totally additive.

There are other examples again I don't want to ruin the surprise there's another one to sign this week that I think is coming to every day ultra.

And it's like it's and it's not a running brand and it's a cool thing to introduce this audience to because it's something that will help them be healthier and it's it's an alternative that they might not have heard about before but maybe they've heard about this thing that they should have considered anyway.

So it's been it's been really cool to watch this evolve from that like podcast collective model to this is an agency model and like brands are literally telling us their tent pole events and their budget and we're helping place shows and and media properties to help them execute their business plans.

So if you think about like an apparel brand that's doing race sponsorships they need to tell the audience tell the running community about the races that they're at and the activations that they're doing and you could have a marketing coordinator do this that's getting paid you know 50k a year internally or you could spend the money on media properties and let me do it.

Or let us do it shout out to Emily Holland who's helping like actually execute this she's very detailed oriented I'm not I just I'm the idea guy and sales guy and talking head.

But so the idea is that like brands are outsourcing the like how do I execute this thing to a property that can think faster can can create deliverables and can execute.

And so instead again instead of having an internal full time employee doing this we're creating efficiency and the model is the brand pays us we pay the host so we have the meetings we can set up a meeting with 10 10 shows all at once so that a brand is not having 10 separate meetings saying the same thing.

And so that a brand is not setting up 10 vendor relationships with 10 different people chasing payment because the payment piece is a pain in the ass and so the ability to just pay one property and have that property distors it and be motivated to chase down the payment versus again 10 different conversations it's a model that works for everyone where the brand wins the host wins and hopefully the audience wins as well because

their favorite podcast is able to keep the lights on and they hear about new and cool stuff and you know get a discount for doing so or can go do a thing with a brand somewhere if there's an activation involved.

Hey everybody real quick I want to address a question I get asked all the time is should I be taking I be profan in the middle of a race and when you're in the middle of a race and you're feeling sore your legs are hurting it can be really tempting to pop that at the light candy but you don't want to be doing that for many of the reasons number one is I be profan can actually to more long term issues then short term issues because in short term it can help to numb the inflammation away but in a long term standpoint you can actually lead to even more persistent injuries because you need some level of inflammation to have.

You can help your body to heal and so I be profan basically gets rid of all the inflammation including the healing ones that allows for long term issues number two it also can really mess with your stomach and when you're in an ultramarathon stomach issues are not good stomach issues are actually the number one cause of DNFs in an ultra and we don't want that at all so what's the solution my suggestion is to use a topical pain relief spray which I've been using for three years in my ultra running career specifically by play on pain relief play on is an all natural ingredient topical pain relief spray that you're using.

You can spray right on your muscles and it allows to get rid of the necessary inflammation that needs to get rid of in a matter of seconds at the source so think your muscles point bones joints anything that you have that is causing pain out there it can do relief in a matter of seconds and doesn't have any long term effects plus it won't mess up your stomach.

So if you want to get plan pain relief a try whether it's on your long runs in your training or my favorite in the middle of a race you go to plan relief dot com and use code every day ultra check out for 20% off your order that's play on relief dot com with code every day ultra check out for 20% off your order also if you're looking for really great trail running apparel that's going to keep you nice and cool in the warm months coming up and that's just going to be overall comfortable I suggest using John G apparel not only is there stuff comfortable but they have a five year guarantee so if anything rips tears or shreds you can go ahead and say.

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So I want to get back a little bit I mean I love here at the business side of my brain is I love hearing about this but I want to think about that moment where you tell your friends I'm going to quit if I don't quit my job don't let me house do you feel like your running journey or thing less is that you have learned from running allowed you.

To say both no and yes in that moment to look into the unknown and be like yeah i'm all in.

Yeah so very specifically I had a conversation with um Ian the CEO of scratch and he was telling me I had this conversation was like April or March or April and I was like stuck.

In this period of stasis and I couldn't figure out how to how to make change and he was like.

When you when you stand on a starting line you don't know what's going to happen right.

How many times you do that and it's you it usually ends up being okay and if it's not okay you can troubleshoot it is like this is quite similar is like I don't I don't know your financial situation but.

If you don't make any money for six months you're probably not going to be homeless right i was like yeah that's true um it's like okay then why can't you take a risk it's like damian.

And and he was like slightly more bold than it even the way i'm describing it and um he was right like I owed it to myself to take leave he walked me through this.

Um thought exercise of the four zones of um i'm going to butcher the like explanation of it but they're four zones of competence so it's goes up to excellence and genius and in a certain in the third quadrant you're doing something that you're good at you're paid well to do it and it's not fulfilling and I was he's like that's the danger zone because you can live in there forever and it's it's a track.

And he's like you'll you'll burn yourself out in that space but you'll you'll stay there because you're paid well and you think it makes you happy.

I was like fuck I was like damn this is this is where I am like okay we swear yeah yeah I was like I was like fuck this is this is where I am like like I I don't take for for granted the fact that I was being paid well to do something I was good at and I wasn't I wasn't thriving.

Um and and so he's like you want to find a way to get yourself into that fourth place where you may or may not be getting being uh get paid well but you're doing something that's stimulating and challenges you and puts you in this flow state and zone of um both competence but also excellence where you're you're being challenged and if you get paid well it's an upside like it's a positive.

Um and so I mean the irony is I made as much if not more last year than I did the year before um and this year should be even higher and and that wasn't the goal the goal was I have been happy to take a little bit of a haircut for more control.

Um and the the equivalent or more is just like massive upside um but it is to say that like I wrote this whole sub stack on it and I wrote the line like I I took the leap knowing what my parachute looked like um I wasn't building the plane as I was jumping out of it.

Um or I wasn't building the parachute or finding the parachute as I was jumping out of it like I knew what the parachute looked like because I've been building the parachute for years and it was an extremely potentially over calculated move that just like kept getting better as as I continued on that leap.

Um I really didn't think that the collective concept would um snowball to what it has or the potential that it has it's just like it reduces the pressure for my own podcast to continue to do such high volume of partnerships from revenue perspective in order to like live and pay my bills.

Um so like I can reduce that by 30 to 45% which um is a lot of a lot of effort in reduction and refocus that effort on the collective and I'm doing some consulting for a brand called eternal I'm like really enjoying that work um and then doing some advisory work for for other brands um that's not as hands on more of like an hour to a month kind of a thing.

And it's just like I get to live in this um go to market specialist space and some of it is angel investments that made some of it is advisory agreements I have some of it is like monthly consulting agreement and some of it is like this agency model where I'm giving go to market advice to brands and the payment mechanism is a commission on sponsorship.

Do you feel that so I love this and I love the business aspect so you took this big risk it is but not that big of a risk like how I think if you look at it it's not that big of a risk it was extremely calculated.

Yeah so this is what I guess where I'm going instead is that I would say it looks a bit like someone who has extremely good results the point to they're probably going to play they've gotten a golden ticket multiple times and they're like well should I take the step to be a full time professional athlete so we do have a background they've years of training it's not a flu you know they have this background.

But it is that moment of like am I really going to do this do you have you found that your running has changed at all because of the step that you've made in the business side of your life.

That's a really interesting question I'm curious if you're digging for a yes it has.

You could also say my capacity has been completely consumed by this side of my life.

So no not really or it's yeah can't believe the running last summer was the best it ever was best it's ever been I went to Tahoe kind of with like a little injury.

I think because I was just like extremely stressed and then I had this like massive relief release relief and release and.

And then I trained for a 40 mile race in two months and went from like running 20 miles a week to.

60 miles a week and finished a nine hour race with 7000 feet of gain and felt fucking fantastic except for it like a three hour stretch.

That's pretty it which is the third of it so yeah.

But like I had some of the best long runs of my life I had some of the best workouts of my life going from zero to 60.

In July of last year.

July and August and then I ran the Grand Traverse for those who are familiar it's from Crestitude to Aspen it's 40 miles mostly above 9000 all above 9000 feet mostly above 11000 feet.

And I felt like really really good I was like it was like the best most confident I'd ever been standing on a start line and I still got my butt kicked but it was.

It was awesome February of last year I ran black Canyon and interestingly like I didn't bring headphones and I ran most of it solo.

And it took me five and a half hours I think because I crashed so hard at my 19 after the like 19 mile downhill start.

And I had the day that I needed on on that day I was like really in it like trying to figure out what to do professionally.

And I just lived in my head the whole the whole time I must have said like 100 words and half of those were to my phone to make a video.

And the other half were to some guy I was running with at mile 24 25 that was like we were making jokes and that was pretty much it.

And so I had these like real to really categorically different race experiences that mimicked how things were going at the time.

And then yeah just like it was an interesting year of running and but like I said the duration or a amount of running didn't really change like I'm busier than I've ever been.

While enjoying it more than I ever have.

So it's not like I have like you know two extra hours of my day to go run another 10 miles nor do like I can't run more than 80 miles a week because I have any miles a week.

So I don't think I would try maybe I do more bike miles or sauna or strength training which I definitely should be doing.

But like the volume of running has not changed it's just like I've been doing it for different reasons.

Do you care to elaborate on those reasons?

You don't have to.

Well I'm just thinking about it like explain that so I don't know running can be an escape or it can be like a celebration and for a while it was like the only part of my day I could control and

and it was taking away more than it was giving I went through like a few rounds of burnout in the last couple of years.

And David helped me work through much of it and some of it was just like I just like need to pull the plug and just like run 20 minutes a day.

I think it's important to acknowledge that that like that's okay and you don't need to be in training year round you shouldn't be in training year round.

But but now

running is like very much a part of the overall story like somebody asked me the other day like what is your

like what

what do you care about I was like I want to help motivate people to

to do more than they ever thought possible believe in themselves more than they ever could.

And just be better and better doesn't mean faster better means like a greater sense of belonging or self belief or

whatever like however you want to define that in a subjective manner versus like metric based.

And I feel a lot more open to sharing that story now for some reason.

And just like going a little more all in on like the content side of running like I'm not competitive but like not competitive in a racing standpoint particularly here in Boulder.

I'm like quite quite average as three hour marathoner which is funny.

And so it's just like what yeah tough sell.

It's it's a that's a very concentrated.

I've run 259 and I get I can like get dropped on group runs like constantly here.

So anyway I joke with Matt Daniels and every years ago that Boulder average is having a shoe sponsor.

There's ironic because I've like had a shoe sponsor for the last three years so I am I am officially average.

He was like I'm not even the fastest miler on my street. They're like three sub four milers.

That's hilarious.

Anyway, yeah, it's just like it's been an interesting and fun journey and it's really fun to just like double down on the storytelling aspect of it.

And then I really like building a public of the business side of things.

And so long run labs has been like a fun mouthpiece to have from megaphone to have to both talk through and learn from other people.

And then just like get to demonstrate the building in public of this agency model of like what it looks like to pay your bills through podcasting.

And all the other stuff that goes into like media business and property in 2026.

Yeah, no, I mean, my actually one of the questions when I was thinking through our conversation that I was going to ask you is what gets you out of bed to run every day because

Yeah, exactly.

No, it's go for it.

So I asked that question.

I asked a similar version of that question to somebody running the breeder league this morning is just like community.

I love the having the fitness to say yes to anything shout out to Kevin Goldberg, who he's the best.

I love Kevin.

He is the best.

And he's one of the friends that like I train so that I can respond positively to Kevin's texts.

Which are often like, do you want to do this stupid thing tomorrow?

And like I love I love being able to say yes to those things.

And I joke that like the last couple of years my winter and spring training goal is to be adventure ready.

So that I can say yes to any adventure with a couple of days notice.

So like I don't do a workout that week and I stop Saturday feeling, you know, good to go and half of those invites come from Kevin.

Which is much appreciated.

And yeah, there's a competitive aspect of it.

Like I like the numbers.

I like improving.

But yeah, I just really like being immersed in the community.

I like, you know, when I go to Tahoe every year for Western states in Broken Arrow.

I like doing adventures out there, whether it's running Broken Arrow or you know, going from Olympic Village to Donor Lake.

Like that is a must run for everyone.

I haven't gone from Donor to Olympic Village.

Olympic Village.

I've only done it that way.

I never know.

Yeah, that way it sounds more fun.

It's downhill.

Yeah.

So like I want to do stuff like that and be able to say yes to those types of adventures.

And I just really love the like three to six hour runs.

And I want to do as many of those as I can.

And so for me, running is like the facilitation of being engaged involved in the community doing fun stuff.

Like Boulder Breedleague or working with Boulder Thon and doing group runs and panels and stuff like that.

Or having the fitness to go run, you know, for five hours up in the mountains.

I love that.

Yeah, I think there's always when you've been in the sport for a number of years.

The inflection point of what gets me to go out and do this.

And so I was curious what was motivating you to get out there and put in the miles, put in the time.

Yeah, early on it was breaking three hours in the marathon.

And I did that.

And I was like, huh, that made me a better person, not because of the time, but because of the process that like setting a goal working towards the goal and achieving the goal highlighted.

And I thought it would make me like not a lot of false assumptions as it relates to like that specific time goal.

And it took four years to do it.

And it's mostly just a demonstration of like setting a challenging, but, but realistic.

Like a couple of years ago, I was starting with motivation and David was like pick something scary.

So I signed up for black canyon because it's a 50 K that's runnable.

And in theory, I could run the whole thing.

And he's like the scarier, the better, the less confidence you have.

And I did it and it was, it was great.

And I was February of last year.

And then I had also signed up for Grand Traverse.

And I like really couldn't fathom running 40 miles, which is like funny for your audience because many people listening are like, you know, running hundreds and 200s and 300s.

300s, yeah.

Yeah, sure.

It keeps going.

It keeps going.

I really need speak of nonendemics.

I need fidelity to sponsor the 401k, which is 248 miles.

We really need that to happen.

I have a friend who works at an agency that works that spends tens of millions of dollars for fidelity.

And I'm like, dying for him to help make this happen.

I'm chatting with him tomorrow, actually, or Friday.

But I digress.

I couldn't fathom going 40 miles.

And then I finished the 40 mileer.

And Zoe Rome and her partner TJ were standing at the finish line.

And they were both accomplished 100 miles and run Leadville and states and all these things.

And Zoe was like, you could have run 50 today.

It's like, yeah, but not if I had, if I had to race the last 3.5 miles of a 3500 foot drop, I might have been able to do, you know, 10 miles instead of falling off.

But it's crazy how the perspective shifts because I was like, yeah, I think I actually could have.

And so that's the piece that I love the most that like it's this constant refreshing of what's normal or what's possible.

Like if 2013 me could see what what I did last year, he wouldn't recognize me, both professionally or running wise.

And so to me, that's like, that's what gets me up and out of bed for work or for running.

Because I want to, I want to look ahead to 2036 and be like, wow, the 2026 version of me would not believe where I am today.

And he'd be so proud of me.

And today it's just table stakes.

And, and that's, that's what gets me, that's what gets me going.

And, and then helping other people get that same thing. And that's why I'm so public with the whole journey.

Because I, like, I've seen what it does for me when Dylan Bowman says trail running will save the world.

Like, that's what he means.

Like the, or that's my interpretation of what he means.

Like the context or the empowerment that you can get from trail running is so obscenely impactful that when I hear, like,

and it's why I'm so motivated to like, bring minorities and people of color and people like all these different groups of people to help them feel like they belong because

I've seen what it does for me.

I've seen what it does for my community.

I want everyone to feel welcome in the, in the pursuit of like creating the best version of themselves.

And like that fires me up.

Of that. Yeah, I mean, I would say.

If you want to meet the best version of Alyssa, it's probably on a trail run.

Exactly. We're at Terry.

Terry's.

Actually, no, that's not the best version.

I don't know if that's the best version of anyone because we're all just losing our minds, but it is fun.

It is fun. Definitely not the best version. You're right.

Yeah.

The last question I wanted to kind of ask.

I did a little snooping on ultra sign up and I saw your sign up for a potential adventure.

Are you sharing that?

Yeah, yeah. What's the, what's the, what's the stoke on that?

So I grew up in the Boston area.

I got into running in Boston.

And if you ask me where I'd run trails, I'd say Marin.

And I needed a bit more time for a Saturday invite for a long run because it required a cross-country flight.

And so I got into trail running from racing North Face 50 at North Face 50.

It was a great event.

Truly, truly the best.

I did the marathon relay with November project and like that was my entry point into understanding what trail running was.

I was doing a leg of the, I was doing a 10 K leg when Hayden and Zach Miller were finishing their 50 mile showdown.

And I, I thought a bull was running behind me and it was, it was Zach grunting.

And again, I was running a 10 K and they were at mile 49.

And Zach blew my fucking doors off.

It was wild. I mean, I was probably running like a seven minute pace and a 730, I don't know whatever was.

And it looked like I was standing still.

And I was just, this was 2016.

I was like, I don't get it. He's, he's like, I wasn't running 50 miles a week at that point.

That was like, like, three weeks of running for me.

And I was like, this is crazy.

And then I watched the video of this showdown that they had, which is absolutely iconic.

And I had recently gotten introduced to Mike Wardian and Mike introduced me to Devon Yanco.

And this was like my falling down the rabbit hole.

And so anyway, those trails are incredible. Every time I go back to San Francisco, I find my way out there if I can.

And so I was talking to Dylan the last time I was in Marin.

And we were at October fast. And he was like, dude, you got to come out to, to Big Alta.

It's like the best trails in the world.

And it's like right outside my front, the front finishes in my front door from the Golden Gate Bridge and all this.

And I was like, all right, I'm in. And then I waited like a month and signed up.

And yeah, I'm just stoked to run on those trails. I've never done an ultra at sea level.

My my fastest 50k was, you know, starting and finishing and crest a but so at 9000 feet.

I guess that would be black canyon. So that finishes at what 2500 feet or 2000 feet. But anyway, never done one at sea level.

And I'm excited to like climb all these climbs like with oxygen.

I'm always shocked. I've done the Lake Sonoma 55k. I know exchanges and says, and I finished that race and went, that's the most runnable 8000 feet.

I've ever done in that. I don't know how I can say that. But you're like, yeah.

How am I still running all of this? But this is 8000 feet in a 55k, which is all right. That's a lot.

That's a lot.

I was like, oh, rude. That's so much running. And big Alta has 7000 feet in a 50k.

Yeah. But you see the times, you know, like these are comparable to, right?

You know, a four or 5,000 foot course. So that should be a lot of fun.

Yep. Nice. Well, anything else you want to leave our listers with?

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And it helps us, you know, keep the keep the fire stoked and rating and reviewing is is even better.

But if if you like a conversation, share it either share it on social or share it in a review or share it privately with with the host.

That stuff is like like paydays for us. It's it's wonderful.

I love that. One of the things I really enjoy doing is telling people when they're doing a good job because I don't think we get to do that that often or we do do that that often.