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Develop a Marathon Mindset with Jesse Randall

For the better part of twelve years, Jesse Randall has worked in the Phoenix Startup Community. He’s worked with accelerators and venture capital funds, helped over 200 Startups to raise capital, and even started companies of his own, but what not many people know is that Jesse also competes in endurance sports like triathlons and Ironman races. He’s learned a lot from both sides of his life, and to kick off Season 2 of Ignition Point, he’s sharing some of the parallels he’s found between the two so we can discover and discuss what it takes to develop a Marathon Mindset and sustain tenacity.

Between now and April, Ignition Point will be featuring 20 Amazing Guests, covering topics that relate to one central theme each month. So, throughout October, we’re all in on Tenacity.

If you enjoyed this episode, please follow the show wherever you get your podcasts to get notified when new episodes of Ignition Point drop every Monday!

To catch up on all the Guest Features from Season 1, you can click here to check out the Season 1 Recap.

For more information about Jesse’s latest startup, you can click here to check out Sweater Ventures – a Venture Capital Fund that anyone can invest in.


Welcome to Ignition Point – the show that’s here to get you fired up and ready to win the week. If you’re looking to amplify your mindset with a fresh perspective – you’re in the right place.

Hey! What’s going on? I’m Steven Miller, and this is Ignition Point – the show that gets you fired up and ready to win the week.

Man, it is good to be back! Just in case you missed last week’s Season preview, we’ve upped the ante for Season 2. Between now and April, Ignition Point will be featuring 20 Amazing Guests. That’s double the quantity, but we’re also doubling the quality. How? Well, instead of covering one topic a week, we’re going to be covering topics that relate to one central theme each month.

So, for the month of October, we’re all in on what it takes to embody tenacity. And it all starts right now.

To kick off the season, I’m joined by Jesse Randall.

Jesse is very optimistic about the future and believes that we have the potential to re-shape the world around us. When we sat down to record this episode, he mentioned something that really stuck with me. Now, I’m going to paraphrase here, but wherever you are, take a look around.

Unless you’re listening to this podcast in a forest or hiking through the desert, so much of the space you’re in is manmade. Your smartphone, the clothes you wear, and even the laws we abide by. The same can be said of a ton of the problems we see around the world, but if people like you and me created them, then people like you and me can be the ones to solve them.

To create the future we want requires tenacity, but what makes someone tenacious?

In my opinion, Jesse is uniquely suited to answer that.

Jesse’s been in the startup space for the better part of twelve years. Since he got his MBA from the Thunderbird School of Global Management, he’s worked with accelerators and venture capital funds, helped over 200 Startups to raise capital, and even started companies of his own.

Outside of work, Jesse’s big on family and exploring the outdoors. He’s even hiked the Grand Canyon from rim, to rim, to rim. But what not many people know, is that Jesse also competes in endurance sports like triathlons and Ironman races.

He’s learned a lot from both sides of his life, but he’ll be the first to admit that if you want to find success in Endurance Sports or the Startup scene, tenacity is a trait that is absolutely required.

So, let’s get after it! Here to share what he’s learned from Endurance Sports and what it takes to develop true tenacity, this is Jesse Randall.


So, from the startup side of things I’ve been deep in this for quite a while. And I don’t know everything, but I’ve been around the block a couple of times – and I’ve still got a ton to learn, but I’ve found that the more that you develop your ability to push and persevere through something, the more likely you are to find success. Some people are automatically endowed with that, and they just persist because it’s who they are, and others don’t.

It’s easier to see the exit than it is to persist through a situation.

I had been incredibly sedentary for probably six or seven years because I got into grad school, and I didn’t gain a lot of weight or anything like that, but I was in the worst shape of my life. And I still remember I was at a job and they were up on the third floor and I told myself, “I’m going to take the stairs because I’m healthy!” And I would go up two flights of stairs and I’d be so out of breath that I would walk around the interior hallway in the building once before I’d go into the office so I could catch my breath, and I just thought, “there’s something wrong.”

And somebody challenged me to do a triathlon with them and I thought, “you’re insane. I don’t run in straight lines with no purpose, and I certainly don’t swim in a pool and I’ve never done anything but ride around the block on a bike with my kids.”

So, it was a huge step out of my comfort zone to do that, but man, I fell in love with it. The first one was kind of a medium disaster and I looked around at all the old guys and all the teenagers that beat me and I thought I could do better than this, and I doubled down, did it again, and totally improved my time and felt great coming out the other side and someone invited me to do an Ironman, and it was all downhill from there.

Now, by no means am I a professional, I’m just an amateur endurance athlete. I’ve done five Ironmans and you learn a lot of lessons in what it takes to get there. It’s typically kind of a process of pushing yourself to where your theoretical limitations are and then giving yourself time to recover and then going back and doing it again. And as you go through this kind of a cycle, it allows your body to adapt and to strengthen itself and over time you become stronger and stronger and you can go farther and farther.

Anyways, I’ve totally gotten addicted to this other part of life and there are an awful lot of parallels between the world that I live in professionally in startups and the world that I choose to be in to push my body and my mind on the endurance sports side of things.

One of the parallels that I’ve found most impactful is this principle that frankly, I made up; at least I can’t find any information about it anywhere else. I call it “grit integrity.”

So, integrity is doing what’s right even when no one is looking. We all know that feeling, right? I mean there’s plenty of things in our life where if someone wasn’t watching us or holding us accountable, we wouldn’t do it. And then the notion of grit is just enduring through something, pushing through something, persevering, even when the odds are against you. Like all of that stuff like just crumpled up around this word called grit.

So, when you do it together, “grit integrity” to me, is defined as doing all the crap that you don’t want to do and that’s really, really hard, even when no one is watching you. Because it’s so easy to kind of want to be in the limelight and to know that, “oh, well people see what I’m doing,” and you kind of have this notion of social accountability that I think we rely too heavily on.

Probably 80% of my training, I’m alone. No one else sees me get my butt out of bed at four o’clock in the morning to go and meet some guys for a ride. No one sees me when I have to cut out and go for a run in the middle of the day. No one sees me when I’m doing endless laps at the pool. I’m all by myself and no one else is there to hold me accountable except for me.

Most of the time, I don’t want to do that stuff. Some people love swimming; I despise swimming. I can’t tell you how much I hate getting in a pool and having to do laps. It’s just so incredibly boring for me.

Having the ability to look at something and say, “I don’t want to go do that today,” and not having anyone else there to pressure you, no coach to harp on you, no one else to hold you accountable, but just you saying, “I need to go and do the right thing.”

There’s not always that social accountability to give you the motivation you need to push through something even when you don’t want to do it. Because I can tell you 80% of the stuff you have to do when you are in a startup environment and it’s just you or you and a couple of co-founders or even you and twenty employees, you don’t want to do most of that stuff. The fun stuff is maybe the 20% and we gravitate towards the fun stuff. But I can guarantee you that if you don’t focus on the 80% of the stuff you don’t want to do, that you will fail and it will come back and will haunt you and it could totally upend your startup, it could put you in a bad position, it could do all kinds of things.

So, when you take this principle of “grit integrity,” and you identify those things, and you’re very intentional about it, and you know, “these are the things I don’t like to do;” acknowledge that you don’t like to do them, and then hunker down and do them anyway. Because if you’re really disciplined, you’ll be able to look at that and say, “I’m going to do that anyway, even though I frickin’ hate it.”

But to back up just a little bit, I want to make one comment on how it applies – I think – probably the most when you look at what it takes to go and say, run an Iron Man, and complete that race.

When you first contemplate doing it, you look at it and you just think, “my gosh! That’s a 2.4-mile swim, 112-mile bike and a 26-mile run. Let’s just cap it off with a marathon. Why not? Right?”

You look at that and it’s just like, “that seems impossible,” but you look over there and you see people doing it, but you say, “it’s impossible for me,” and you have this mental block that, “this isn’t possible,” that, “I can’t break through this barrier.” And usually what most people do is they’ll start picking up events that are smaller, right? They’ll do a sprint triathlon, or an Olympic, or do a half Ironman, or they’ll go do a marathon on its own, or they’ll do a century ride on its own. And you start breaking through these mental barriers of what you can do. And it’s really not about your body anymore, it’s more about your mentality.

So, the person I was talking about it with, we were specifically talking about fundraising and what it takes to go to wealthy individuals to raise money. Now, if you’ve never done that before, it is incredibly intimidating going to someone that’s managing a five hundred-million-dollar fund, or a family office that’s worth billions, or even an individual that’s worth fifteen or twenty million and is writing checks as an angel. It can be incredibly intimidating because that’s not you. I mean, you might come from that world, but the vast majority of us certainly don’t.

And so, when you go to have a conversation with someone like that, your mind is totally in the wrong spot, because you’re almost shutting yourself off and causing failure before you even get there because you feel like it’s not you and that’s not your world. And that mental block can cause you to stumble and fail, but the funny thing is once you work your way into that world, and you become comfortable, and you figure out that everybody there is human – just like you – all of a sudden you can dance on the same dance floor with everybody else and you’re fine.

And I find that to be the same inside endurance sports. When I first started doing it, it was kind of like I was afraid, right? So, because I was afraid, I would train because I didn’t know what it was going to be. But once you’ve done a couple of these, all of a sudden, you’re not afraid anymore and your motivation factor changes because you’re comfortable with it. Because you look at it and say, “well I could do that, it’s just a matter of how long it’s going to take me and how much it’s going to hurt during and after the event.”

So, when you have three sports you have to do, you have to manage a lot, but there’s still a core strategy of giving your body time to recover in between those things that you’re doing. So, if I’ve got to go ride 112 miles in an Ironman, when I go out and ride my bike, I’m not going to go ride 112 miles every single time I ride my bike when I’m training.

That’s a terrible strategy.

I mean, theoretically if you had the time, you could do that, but that’s not going to be the way to get your body to achieve its peak performance.

The better strategy is you might have three workouts, and one of them you might try to push for like eighty to a hundred, and that’s your big workout. Your other ones might only be thirty miles or forty miles, and it might sound weird that, a forty-mile bike ride is a recovery ride, but when you’re comparing it to 110, or 120, or 200 miles, whatever; it is recovery. It’s operating within the limitations that your body has already achieved and you’re not pushing your body to achieve something new or harder, which is how it tears its muscles apart and everything else.

So, you go out and you do these cycles where you’re pushing your body really, really hard and you’re tearing down muscle, and you’re pushing past your limits. You might still be working, but you’re taking it down a few notches and allowing your body to recover, and then you go after it again. And if you don’t do that, your body ultimately gets to a point where it’s just feels like you’re lagging, and sluggish, and like you’re not improving, and it’s because you’re not, because you’re not allowing your body the time to recover.

If all you do is just push yourself to the max and you work fifteen hours a day, seven days a week, forever – A, you can’t do it forever – but B, you’re going to get to this point where you’re just mentally, totally burned out.

Now, the way that you can turn around and cause recovery for yourself is something that’s completely individual, right? And you have to do things that work for you. Like for me personally, it’s doing this endurance sports stuff, which is insane, right? But it’s my outlet. And so, I’ll work my butt off doing my businesses all day long, but every morning I start my day off at 4:00 or 5:00 AM by going out, and going for a run, or going riding, or going swimming, or whatever, and that’s my outlet from all of my regular work that I do.

You should have something in your life that gives you that outlet and gives you that time to mentally recover, hopefully even on a daily basis. I mean, that’s what I tried to do, and I think that the people that are most successful make that a priority in their life.

Pro tip: you always have time for the things you put first.

Which sounds stupidly obvious, but yet I think that we miss that a lot. We make excuses all the time.

“Oh, I don’t have time to go and exercise, because I’m working too much.”

You know what that is? That’s a choice. That’s your choice to work instead of going and doing something that’s recovery. In my opinion, recovery is probably one of the most important things you can do, and so if you want it, you will make time for it.

There’s so many hours in a day; you pick that thirty minutes, and you layer it in there, and you make it happen.


When I lived in New Orleans, I was taught a train of thought about how to celebrate Mardi Gras the right way. People say, “it’s a Marathon, not a Sprint.” Granted, they were talking about the way that you should party during Mardi Gras, so you don’t collapse halfway through, but I think the saying applies here too. Your work life is a lot like a marathon – it’s one insane, never ending race – and you need a healthy approach if you want to stay fired up about what you do.

Jesse’s story shares a lot of great takeaways on how you can make it through your marathon, but I want to focus on the three key skills that contribute to developing a Marathon Mindset.

For one, stamina is a pretty big deal. Sometimes you’re going to need to pull yourself up by your bootstraps and put the “grit” in “integrity.” If you’re over 30, you’ll probably think of the old saying, “when the going gets tough, the tough get going,” but if you’re under 30, you’ll probably think of the saying from the movie Zombieland, “nut up or shut up.” Either way, whatever you’re working toward, you need to do whatever it takes to stay focused and push forward.

Then you’ve got his point on mental blocks. We all deal with them, but you need to do away with them. The second you start making assumptions about people or circumstances, you end up creating a false narrative about your situation. Keep reality in focus.

I never thought I’d find myself referencing a children’s book, but if your barrier has to do with people, take a philosophy lesson from the prolific Japanese children’s author Taro Gomi, Everyone Poops.

You have to recognize that no one is above or below you. You can do anything you put your mind to, and you can interact with anyone you want to. If you haven’t already, erase the word “can’t” from your vocabulary.

The last big lesson is that you can’t just press and press and press some more. You need to find your personal outlet and make time for recovery or you’ll literally run yourself into the ground. That outlet can be physical activity, or it could be a creative activity like writing, painting, or podcasting. It just has to be a way for you to disconnect from your grind. Without recovery, I’d say it’s close to impossible to do anything at a high level. So, schedule the time to recover. Otherwise, I’d bet you probably won’t.

Tenacity is the result of these three traits being in alignment, but if you lack just one of these three skills, you’ll never be able to harness the power of true tenacity. Check this out.

Let’s say you can surpass the mental barriers and you take time to recover, but you lack stamina. Without stamina you’ll be forced into recovery more frequently, which will increase the chances of you dealing with burnout. Burnout is tenacity’s kryptonite.

Now, let’s say you’ve got the stamina part down and you take time to recover, but you get caught up by mental barriers. Without mental toughness, you second guess your direction, create false narratives, or misdirect your energy. Tenacity demands the clarity and self-belief that only come from mental toughness.

Lastly, let’s say you have all the drive, mental clarity and stamina in the world, but you never recover. Without taking time for intentional recovery, you’ll keep hitting a wall. You’ll only ever get so far before you shut down. There’s no incremental improvement in this scenario, and your stamina will suffer for it.

In the real-world, this Marathon Mindset and sustainable tenacity are very similar. They both require stamina, mental toughness, and intentional recovery. When you have all three, you can do damn near anything you put your mind to.

This is your opportunity to ask yourself, “Do I have these three skills locked down?”

If you don’t, start by making a plan for how you can improve or develop the skills you’re lacking and build toward balancing all three so you can live with and sustain real tenacity.

But if you’ve got it locked down, really drop the hammer this week. Go out and be relentless about what you need to accomplish and crush it.

I’d like to give a big thank you to Jesse Randall for contributing to this week’s show.

For the longest time, only the wealthy 1% have been able to put money into Venture Capital funds, but Jesse’s latest startup – Sweater Ventures – is here to change that. Right now, Sweater is setting up a Venture Capital Fund so that anyone can invest and become a Venture Capitalist.
You can sign up for the Sweater wait list right now by going to

For the easiest way to connect with Jesse, check out this episode’s Show Notes at There you’ll find links to his social accounts, his contact info and more bonus content.

If you enjoyed this episode, please share the show with someone you think it would help and follow the show wherever you get your podcasts.

New episodes of Ignition Point are available every Monday, but if you’d like to catch up on all the Guest Features from Season 1, you can head over to to check out the Season 1 Recap.

If you’d like to give us feedback on how we can improve, you can always reach me directly by emailing

That’s going to do it for this episode, so stay motivated and keep moving forward.

If you put in the hard work right now – one day – you could be the one motivating the world with your story.

I’ll look forward to speaking with you next time on another Ignition Point.

Now get on out there and win the week!