The Comeback Chronicles Podcast

From Data Scientist to AI Entrepreneur: Nathaniel Mahowald's Remarkable Journey

• Terry L. Fossum

Share episode

Send us a text

Nathaniel Mahowald, founder of Pickaxe, shares his remarkable journey from living in a van for over two years while pursuing entrepreneurship to building an AI company serving over a million monthly users.

• Transforming from data scientist intern to CEO in just six years
• Living in a van to save money while college friends took jobs at Google
• Starting multiple failed companies before finding success
• Getting laid off during COVID and working without pay for five months at a startup
• Finding his first customer in Alaska through a Reddit post
• Riding a beat-up motorcycle across Florida to meet a potential mentor
• Building Pickaxe to help coaches and consultants leverage AI in their businesses
• Growing to over 1,200 paying customers with exponential growth since 2023
• Making AI accessible and less intimidating for everyday entrepreneurs
• Understanding what you truly want from life to guide difficult decisions

Head over to terrylfossum.com to pick up your free gifts and learn how to break through your comfort zone to reach the pinnacle of success in every area of your life.


Support the show

Speaker 1:

If you've been stuck in fear, self-doubt, your past failures and you're ready to break through your comfort zones to finally reach the pinnacle of success in every area of your life, then this podcast is for you. Here's your host, Terry L Fossum.

Speaker 2:

Hey everybody, Terry L Fossum here once again and welcome back to the Comeback Chronicles podcast. We have a very special podcast today, and what makes this so special is I didn't even know who this guy was about, I don't know, 20 minutes ago and I got on a Zoom with him talking about a service that he provides people. You're going to want to hear about that, and I became so impressed, not just with the service, but with this guy's story, his comeback story. I'm like we need to drop everything. We need to put you on tape, we need to get your story out there to the world. So this is really going to be a blast. It's very off the cuff. Nothing is prepared. We're going to get on and have fun and just talk like two people. So let me tell you who this guy is. Okay, Nathaniel, I'm going to mispronounce it.

Speaker 3:

Sorry, Mohald Pronounce it for me Mohald, yeah, mohald, mohald.

Speaker 2:

Mohald. There we go, and I'm just leaving that on. We're rolling tape, it's all right, man. So right now it's 2025. Just six years ago, in 2019, this guy was a data scientist intern just an intern and then in 2019, he became a data scientist for Vodaai. In 2020, a data scientist for C6 Bank In September 2020, the lead data scientist for Civo, and then he went to be an associate at ARK Investment Management in 2021. And now he is the founder and CEO for a service called Pickaxe, and I'm going to let him explain what Pickaxe is first, and then we're going to go back into his amazing background, his Comeback Chronicle background. Welcome to the show, nathaniel. So glad you decided to jump on and join me here, man, thank you so much for having me.

Speaker 3:

It's so great to get the chance to talk a little bit about myself and talk about Pickaxe. You know, pickaxe is a service for the millions of americans who make money by selling access to their knowledge, whether they're consultants, coaches, they're creating courses. You know, it really is the broad field, and there are millions of americans that work for themselves selling access to their specialties that they have owned over years and years of work. And all we're doing with pickaxe is is saying, hey, if you you see that ChatGPT, you know, is a valuable resource for your customers that also gives good advice. Don't have your customers choose between that or hiring you and working with you.

Speaker 3:

You should be able to have all the firepower of that AI within your own business, and that's all we do at Pickaxe is we help folks to build those tools within their own business. And that's all we do at Pickaxe is we help folks to build those tools within their own funnels and within their own businesses so that they can have their expertise combined with the amazing power of AI in a branded environment where they can monetize and control access to it. And we're just so excited to help anybody in that space, you know, build tools to help their businesses. Well, that's how we got to know each other, because I'm as space. You know, build tools to help their businesses.

Speaker 2:

Well, that's how we got to know each other, because I'm as probably the listeners know I'm building out a huge TEDx training platform. Now, I'm not associated with TEDx, but this is called the viral stage and because it is a viral stage, it's the world's largest stage and I'm helping people get on that stage and blow the doors off of it. It's the world's largest stage and I'm helping people get on that stage and blow the doors off of it. But here was my problem. I'm building these amazing AIs I mean better than literally anything else in existence but right now not everybody is on chat GPT, so there's this roadblock there and we don't like roadblocks.

Speaker 2:

So that's where his service was recommended to me and I looked into it. I had some questions about it and right away, nathaniel's like let's talk, and got on this thing. I'm like, okay, yep, so within God willing, the next couple, three weeks, I'm going to be transferring all of this stuff over to this service. So you're going to see his service on my service, which is cool. Okay, you've got an incredible background. I mean six years. But and now, of course, here you are, a young CEO building a company and building it very quickly. It's very exciting and I think it's going to build more quickly, but that's not always the way it was. You told me something that blew my mind. What was that, nathaniel?

Speaker 3:

Well, when I was in college and graduating college, I lived in a van for actually a little over two years and you know, it was just. It was something that it seemed like I needed to do in order to save the money that I wanted to start a business. I knew when I went into school I wanted to be a physicist, but I quickly got rid of that notion and I said I want to be an entrepreneur. This is the only thing that's exciting to me. But I knew it wasn't going to be super easy and while my kind of the other folks, kind of my friends in college, went and worked for Google, I moved into the van.

Speaker 2:

Wow, wow. So they're getting paid a lot of money to work at Google short term, but you had this long term vision. That was a whole different ballgame. Tell me more about that.

Speaker 3:

Well, you know, I think To say I had a long term vision is maybe giving me a little bit too much credit. I think I just was unemployable with my proclivity to just want to do things my own way. I tried to start a bunch of different companies. I tried to start a company that would put these boxes in your house that would mine Bitcoin with solar power. A company that would put these boxes in your house that would mine Bitcoin with solar power. I tried to start a company that would help you give micro donations to local political candidates. I was just super excited about the idea of exploring starting things.

Speaker 2:

And let me jump in right there, because this is so critical and we talked about this real quick and we were just chatting back and forth. One of the things I teach the road to success is paved with failure. It's failure, man. If you're failing, it's not bad. It's a very good thing, because every single person who succeeded at anything of significance at all has failed and failed, and failed, and failed. You're telling me you're one of those people, and you're telling me you're one of those people.

Speaker 3:

I mean, I got this amazing job at C6 Bank. You know, it was so exciting. You know, okay, I'm going to be in New York and I was laid off after three months four months because of COVID. I started work in January of 2020.

Speaker 3:

So, very quickly, shortly thereafter, I was laid off and you're out of college and you're unemployed're unemployed and also the world is ending, apparently, um, so that was a.

Speaker 3:

That was quite an experience, um and and you know, just traveling around and and finding myself and what I really needed to do, I finally started working at at this uh company, sivo, um, and part of that story that I haven't really told publicly is that they did not pay me for four or five months on starting working there. They said, hey, we're going to pay you, but they were an early stage startup themselves and you know, you have to have some empathy for early stage startups. You have to have that kind of drive to just be like I'm just going to make this work, no matter what. I started working at a bar in the nights, you know, bartending to kind of make ends meet, living in the van, working for the startup that was not at the time paying me, and just getting the chance to meet the CEO and to talk to the people working there and see the team that she had built, which is a phenomenal team. And they did end up paying me after four or five months, wow.

Speaker 3:

That's rough, though that's rough to hold on man, yeah, yeah, I would say there's a lot of folks out there that want to start companies and want to be entrepreneurial, and I think a great way to do that is just to work at com, at early stage companies. But it is the wild west out there a bit yeah, yeah, absolutely.

Speaker 2:

But. But, like you said, that's where you're going to learn the wild west. Because you're going to go through those things, you might as well go through them with somebody else's dime and somebody else's heartbreak, quite frankly, and learn all the hard lessons you can wherever you can. Does that make sense?

Speaker 3:

That makes complete sense.

Speaker 2:

Yeah, it sounds like exactly what you were doing.

Speaker 3:

When I was going to start Pickaxe, I had a very close friend from college who actually he was working at Google and we agreed that we were going to quit our jobs and and and work on pickaxe. Um, and I quit and he did not quit. Oh man.

Speaker 2:

Oh man. There's your bud.

Speaker 3:

This was in uh. This was in uh in uh in 2022 and uh, and there was a period of time when I when I really was completely alone, you know, trying to figure out what to do, so so that was probably one of the hardest times is when you are kind of you expect to have a partner and uh, and you know, you're just like and you know you're not making any money at that point right, you're losing money.

Speaker 3:

Um, I'll never forget getting the first customer for Pickaxe. It's this guy in Alaska. I mean, just you put this thing out there on Reddit and you see who will bite. And that was just the most amazing feeling I think I've ever had.

Speaker 2:

Yeah, yeah, like wait a minute. I believe in this idea. But son of a gun, somebody else does too. Huh.

Speaker 3:

Oh my God, that's incredible and that was I didn't feel alone from that day forward, because, you know, without a co-founder at that time I did feel alone, but that first customer really, really helped.

Speaker 2:

Yeah, yeah, absolutely. So before that, you said you felt all alone. And there's a lot of my listeners out there that, whether they're an entrepreneur and doing those efforts or whatever it is, they feel all alone. If you would, let's help them out. You know what was that feeling like for you, and let's get, let's dig into it. You know we don't mind emotion here, that's okay and it's a safe place to talk. And then what kept you going, man?

Speaker 3:

Well, I think that being alone and trying to found a company is pretty much it's the hardest thing I can think of trying to do, you know, because starting a company is already a really difficult thing to do. I know because starting a company is already a really difficult thing to do. I mean, you're out there, it's you against the world, and so you know, it was just a horrible feeling, I mean. But I think you, you really only learn about yourself from putting yourself through those, those, those times. I mean you, you go from a point of getting up in the morning and being like I don't know, today it's going to be me, tomorrow it's me, yeah, the next day it's myself, and I yeah, yeah, yeah, I understand completely.

Speaker 3:

So, so there's. There's not going to be anybody that's going to say, hey, you're slacking off. There's not going to be anybody that's going to say, hey, you're slacking off. There's not going to be anybody that's going to say, you know, hey, you should look at it this other way. You have to get in touch with yourself. You have to think. I need to feel comfortable with what I can accomplish today to understand other people's perspectives without them having to breathe down my neck because nobody's going to tell me that I'm making a bad decision until it's too late.

Speaker 2:

Yeah, yeah, and then the customer tells you, or the ex-customer does Exactly so, finding people to support me.

Speaker 3:

And there's a story during that time I met this guy online who had started a business, a really great guy named Eliam Medina. He started a company called Willing that he sold and now he's out there teaching kids about entrepreneurship, actually in Miami. But at the time I met him and I didn't even have a car. I had a two TCC really old beat-up motorcycle and I was living in Tampa and I drove that motorcycle across the state to Miami just to meet him and to talk to him and just to get advice from him because he had had success. And so I would say, if you are alone and you're starting a business, just go the extra mile to get connected with people who can advise you and inspire you and go and physically talk to them and have dinner with them, because they'll like that. Especially if you ride in on a beat-up motorcycle that's breaking down halfway across the state, they'll be like this kid is going places.

Speaker 2:

Right on. Yeah, absolutely. And it is amazing how people want to help you. You know, all too often we think, yeah, nobody's going to help me out, nobody's going to give me advice. Yeah, no, there's a lot of people out there who like to. I mean, everybody likes to have their opinion listened to. So what you're saying is reach out to them. Huh.

Speaker 3:

Of course, yeah. I mean, I think people don't often think about how they feel when they get asked for help, because if you get asked for help, if I get asked for help, I'm like, yeah, I want to help, I want to be a person that helps, I want to be out there. I see myself in other people and we kind of forget that when we're asking for help, there are people. Even if they're famous and doing quite well, they're going to have the same reaction.

Speaker 2:

Yeah, okay. So now things are moving forward. You've gotten through a lot. What's driving you to push this further? I know you're unemployable and, by the way, for somebody who's not an entrepreneur, that's one of the phrases we use. I am unemployable myself personally. We just can't be employed, we can't do the job thing. It's not who we are. So, first of all, what do you think are some of the traits of the unemployable from that standpoint, and how do you continue to have the motivation to move forward with everything you're doing?

Speaker 3:

It's a good question. You know the traits the unemployable um, I think when I was working at um. Just, you know you. You notice you're unemployable. You look at all the jobs that you work at and you want to go above and beyond your. Your pushing to do things that are beyond even what's expected of you, but always a little bit different from what you know. Whoever's supervising you exactly wants you to do right and if you're finding that that's happening repeatedly.

Speaker 3:

Um, and you will have your own ideas. Okay, hey, it would be best, better, if we did something like this, or you know. Then I think you know you have to go out and test those ideas for yourself and and the market will decide whether or not they're good or bad. You know so.

Speaker 2:

So there is there's that risk.

Speaker 3:

You know, and you know the trajectory of Pickaxe has been one of, I mean, the whole first year. We were just exploring, we didn't know, we, we did every single thing you can think of. We worked with um, we worked with, uh, non-profit organizations conducting large surveys. We worked with some hollywood organizations doing writing and helping uh with them, uh, in in those circles which I can't even fully talk about, all the details of that. But we explored all these different opportunities and you know, I think the thing it's that that same story of that first customer in Alaska, you know, we just saw the core business of Pickaxe slowly growing in the background while we were kind of blinded by searching for these larger enterprise opportunities.

Speaker 3:

We thought nobody's going to care about a business that serves these kind of like solopreneur, coach, consultant folks. We talked to investors and they're like I don't understand those people. Right, who are those people? I, you know, like what are they actually doing? You know, so, you know, we, we, we, for the first year we were really looking, we were like we got to find different customers, you know, and still, you know, people signed up, people told us how much they love the product. We fell in love with with these, these folks, and we fell in love with helping them.

Speaker 3:

And and and 2024 was just a story of of of really figuring out the product and getting it really fit, and since the summer, we've had some basically exponential growth. I would say Things are really taking off. We are seeing just great metrics. We have more than 1,200 paying customers now. More than a million people use the product every month as end users, thousands of monthly active builders building things, testing things out, and we want to be that playground where people can come in for free you don't have to pay to try out the product and just see what it feels like to have a business powered by AI.

Speaker 2:

Well, and just a few months ago I couldn't spell AI. Just a few months ago I couldn't spell AI and I knew at that point that either I learn AI or I retire. You know, that's just the way it is and I'm sorry for everybody listening on. I don't mean to hurt anybody's feelings, but that is the way it is. Ai is like it or not, love it or not, it's going to take over everything. Okay, it is the future.

Speaker 2:

And what I actually got together with somebody who I wholeheartedly endorse now she sat with me for one hour exploded my brain. There's actually still brain matter on my ceiling here. It's really embarrassing and what I realized, what it could do. I've fully immersed myself for I mean last months, just sitting here. I've got several screens in front of me and I'm just learning, training, training, training, learning, training, training, getting frustrated, frustrated, frustrated. You know what I mean by that and training, training and now working with it, from what I'm understanding at a cognitive level, more than 99% of the population.

Speaker 2:

But we have to keep things simple, and that too, again, is where your product comes in, and I think it was Einstein that said genius is making the complex simple, something to that effect a little misquote, but general idea, and I know that's what your product does. Let's talk, let's switch for just a couple of minutes. We've got left here because there are I mean AI as of this recording. This is May of 2025, it's this recording and people are just starting to understand or be aware that AI may be the future and are pretty scared of it and things like that. Give me your take on the future of AI.

Speaker 3:

You know, if you're out there and you're worried, you haven't talked to ChatGPT yet. You know you're kind of worried about this. It's really nothing so scary, you know. You just have to think about it like if you had a free high school or even maybe a freshman, sophomore and college assistant that was just always hanging around in your computer. Be a freshman, sophomore and college assistant that was just always hanging around in your computer and they're going to do freshman or sophomore in college work for you. You can ask them questions. They'll give an answer that somebody like that would give and they'll give a well-constructed answer.

Speaker 3:

But you know, it's like, why not talk to that free assistant just because it's? You know it's not a person, it's in the computer. It's really. It's not scary, it's not. I mean, people are worried that it's going to take their jobs, but it's like, it's almost funny. It's like the high schoolers and the freshmen and sophomores in college, those people are eventually going to take the jobs that are right, like they will eventually be doctors and lawyers, but but you know that doesn't mean we should be afraid of them, that that just means we should.

Speaker 3:

We should figure out how to work with them and and grow with them, and, and, and. If, if I had an army of people like that, I would be all powerful, you know, I would be able to do so much more. So you know, for anybody that's out there, you know what do we think the future of AI looks like? It just looks like getting more acquainted with this technology and using these things for more and more applications. I mean with Pickaxe. Every single day, I am stunned by the things that people figure out how to do that I didn't even know was possible for them to do.

Speaker 3:

And the core kernel of what we care about and we love so much at Pickaxe is, if you're talking to Chachapiti, well, that's some billionaires that are making that bot and that's great.

Speaker 3:

But we want to create a situation where a bunch of hopefully future millionaires, but just everyday people for the most part, can, can themselves be in that position of where the open AI people are. Now, you know, craft something that feels useful to you and put it out there in the world. You know, see what the responses are and and get a sense for that, brand it and really make it part of your business Even make money from it directly through Pickaxe. And so we think that the future of AI is based in people doing their jobs, and increasingly, their job is to learn how to manage an AI that did what their job was before, and that is a great thing. I mean, that's basically what hiring and growing a company is it's bringing on people to help you do the job that you were doing alone before, and now you can do that without having to pay whatever people are asking for for salaries today.

Speaker 2:

Yeah, yeah, well, and it's so much. I mean I don't, I don't Google anything anymore. I don't. You know, I don't do a search engine for anything. I go to my AI and I ask it the question and it uses its web tool and it gives me much better answers than any web search by myself could ever do, and that's just one thing. So now, when I have a question about absolutely anything, I go to AI.

Speaker 2:

Now, oftentimes it is wrong, as Nathaniel and I can attest to Absolutely yeah, but a lot of times it's really really right. And now I've developed it to where it's actually now, way more than just a high school or a college level. It's at an extremely high level, strategic level, helping me develop stuff that I can't even imagine, and it's developing it for me in my voice. So, yeah, it's crazy. So I think, yeah, I agree, it's going to be again, it's going to be everywhere, it's going to be doing everything and you're helping bring it to the masses, which is very cool. Now again, this being the Comeback Chronicle podcast, let's end with some advice that you'd give to some people who are going through the challenges, the setbacks, the disappointments, the failures, the self-doubts, the fears, the excuse, everything else. What advice would you give to those people, nathaniel?

Speaker 3:

thing, at least from my perspective, is to understand what you actually want to get out of your life, and your career in particular. You will be constantly faced with decisions that test that at its core, and there'll be people who offer you a lot of money.

Speaker 3:

There'll be people who offer you other things. And if you are aware of what you really want which is something that it's really difficult to get to I mean, it takes a lot of time to figure that out but if you can say to yourself every day this is what I want, and I know that for sure those decisions will become much easier. And you know, I wish that I had figured it out earlier. And I just think you know, meditating on that and making that decision in your own mind and in your heart is the most helpful thing you can do.

Speaker 2:

I love it. I love it. So, everybody listening. Your job now is to figure out what that is for you. What is that? What do you want to do? What do you want to be on your deathbed? What do you want to look back at and be proud of? What do you want people to be saying about you after that? And then get out there and fail and fail and fail and live in your van if you have to Screw some things up, but do something and then you can have your own Comeback Chronicle.

Speaker 1:

So that's it for today's episode of the Comeback Chronicles. Head on over to Apple Podcasts or wherever you listen, and subscribe to the show. If you're ready to get over your fears, self-doubts and past failures and break through your comfort zone to reach the pinnacle of success in every area of your life, head over to terrielfawesomecom to pick up your free gifts and so much more. We'll see you next week on the Comeback Chronicles podcast.