Ex-Spotify Engineer Starts a Landscaping Business With $400

Welcome to the Ambiguous Truth. I'm your host, Anthony Mistretta. If you like the show, there's a couple of ways that you can do very, very, very simple things that help me out tremendously. Firstly, tap or click follow or subscribe. Super easy, it is literally one button, but it lets me know that people are engaged and listening. Secondly, rate it five stars, that helps get it in front of more people. Thirdly, share it with a friend. If there's an episode that you like, or you know, just show in general, please share it, add it to your story, message a friend with a link to the episode. Would genuinely appreciate some shares. Lastly, comment or message me. I want to make sure that this show is continually adding value to your life, continually helping you navigate some challenges. But in order for me to do that, I need to get some feedback from you and understand if I'm headed in the right direction or I need to change course. That's all. Thank you so very much for listening. I genuinely appreciate it. On to the show.

Welcome, John. Thank you for being here. Before we get into what you're doing now, I would love to just start with your story. Tell us a little bit about your background. I know you came from a very Christian household — I'm sure we can relate on that — but give us a little bit of context so we can set the stage for the direction you're moving in now.

How far back are we going?

As far as you want.

Okay, let's see. I grew up on Long Island, New York. That is a great place to grow up, don't let anybody tell you otherwise — hard to get off though, once you're there and you decide to stay, you're there for life. That was not me, I've never been that way.

Why is that?

God, I don't know. I never really thought about it. Maybe it's because I've been trying to escape family issues. I'm pretty driven, I've never really done what people have expected me to do, I've always done what I wanted to.

Okay, so Long Island, grew up there, very Christian background.

I'm not religious anymore, in fact I don't know if I ever was actually religious. Family didn't really do anything, because my dad was a workaholic, my mom was a stay-at-home mom. Me and my brother both went to a great public school, one of the best in the country — you can actually look it up, Ward Melville, one of the best statistically in the country. I don't know, I just did everything I could to stay out of the house growing up. There was a lot going on and I did almost anything I could — I played sports, I acted, I sang, I was editor-in-chief of the yearbook, I was always out of the house. Didn't really get in any trouble — one time I got into a little bit of trouble, I don't really want to go down that path. But growing up was really nice, besides the family part. Eventually I decided to go to design school because I was editor-in-chief of the yearbook, I got into art, I really liked being able to express myself, both through acting and singing and all the different venues. It was great. And then I went to Pratt Institute in Brooklyn, which is a very good design school, and I studied communications design, or graphic design, where I worked my ass off. Everybody I talked to was like — design school sounds so different. It legitimately is different, because a lot of schooling in college, it's like you take a course, you learn something, and then you just kind of stash it away in your mind and go about the rest of your life. Design school, they literally pin the students against each other to try and out-compete one another, and to create the best designs. I personally did fifteen-hour days, every day, even on the weekends. I didn't really go to parties, I didn't really do much of anything besides working on my designs. Did that really get me anywhere? Nah — design is a very competitive field. A lot of people go into it thinking they're gonna be phenomenal at it, that they're gonna work at these amazing firms like Gray or Ogilvy or whatever, and I was not one of them, I was not good enough. So I ended up moving back home after college for a couple years, and I got some small design jobs on Long Island that weren't the best. But it inevitably led me to understand that design was just not for me — not because I didn't love it, I still do it today to create my own brands and stuff — but in terms of making a living off of it, it was not it. So I did a bootcamp — a software engineering bootcamp, where I actually lived with my girlfriend at the time, she lived in Queens. I went to this General Assembly bootcamp, three months of nonstop, 24 hours a day learning, and immediately after I graduated I doubled my salary, which was crazy — absolutely crazy. I didn't think I was gonna be making that kind of money anytime soon, but I went from like fifty to like ninety, a hundred, and then it just kept going. It was phenomenal. I moved on to JP Morgan after a while, then I moved on to Spotify, and that was my last full-time corporate job before life got in the way. I was there for five years, where I worked on products that helped with their IPO, different licensing, a lot of money stuff, a lot of custom accounting software.

And you were doing software and product separately?

Different times — I got into the company as a software engineer and then transitioned over to product management, because I honestly just got exhausted from having to learn new software things all the time. I hear from people about AI now and having to constantly keep up with that, it's just a total drain, and that's an extension of software engineering. So I went into product to try and escape that — I don't know if I actually escaped the burnout, I got burned out for sure — and then I did product for three years, again working on the custom accounting software stuff, a lot of data, a lot of really complicated processes, a lot of rerunning eighteen-month-old data for updated data that had come in. Just a lot of stuff. And what eventually happened — I think it was the 2022, 2023 tech layoffs — Spotify laid off about twenty percent of their company, and I was included in that, along with most of the three teams I was working with. And that happened right before I had my child being born. So what happened after that was I got a nice severance package, I had a bunch of stock options, so I told my wife, I'll take care of the baby until she gets into daycare, and then I'll figure out what I'm doing next. So that's exactly what I did. I realized that taking care of a baby without boobs is incredibly difficult, especially when your wife is working full time and she's in meetings. Learning curve for myself, because I've never had a baby before, but I always grew up thinking men and women can do all the same things, and having a child made me quickly realize that is not actually true — when she wants a bottle, she's not gonna take a bottle, and there's nothing you can do about it except try to console her for a couple hours while your wife's in a meeting. So we got through that, and after our daughter got into daycare, I started to learn stock market stuff — actually before she was in daycare too, because all I could do was sit and watch YouTube. So I sat and watched YouTube, held my daughter, started learning stock market. Great time to do it, because the AI boom was going, so that worked out really well for me. But it was very draining mentally, because you're watching things go up and down.

Were you day trading?

I was trying to, yeah, at the beginning. I was following these YouTube gurus — some of it worked, sometimes it didn't, it all depends on the temperature of the market. I'd make a bunch of money and then lose it, typical story. The best stuff I found was basically breakout trading — I don't even really want to get into it, but breakout trading is when you have some kind of price level that a stock keeps bouncing off of. Let's say you have a hundred-dollar stock price, but over time it keeps hitting it and bouncing against it — that's a resistance level, which basically means somebody, some institution or whale, is continuously using that as a point to liquidate.

So you just know kind of when to sell?

No — the bouncing is a resistance level, which means somebody with a hundred thousand shares or whatever would sell at that point, which pushes it back down, and it comes back up, they sell again. Eventually though, if everything's going right, it'll break through that, and when it breaks through that hundred-dollar target, it goes — it's like the Kool-Aid Man busting through a wall.

The ceiling has been shattered.

Exactly. Yeah. And then from there it really goes, and eventually you hit some other point where people are selling. But that was kind of the most successful strategy I found. So I was doing that, and eventually took a course to learn how to automate it, and I automated it, and that left me with a lot of free time again. My daughter got into daycare, I had free time, I'd automated something, I had free time, and that's when I was like, I gotta do something else. I was trying to apply for jobs, I couldn't get an interview, even though I had a great resume. Nobody would give me an interview for whatever reason, and I kind of gave up on it, and I said to my wife, I can either keep applying for things with no idea if I'll ever get a job, or I can just say, screw it, I'm gonna go out there and start my own thing. And that's what I did. And now I'm doing lawn care. Now I'm cutting grasses and pulling out dead leaves and taking down branches and trimming shrubs — and I really like it. It's nice being your own boss, it's nice making your own money, it's nice being outside, your job is basically to work out.

You're lifting bags of rocks.

Or bags of mulch instead of weights at the gym. And it feels really good.

You mentioned at the very beginning that you don't always follow rules well — you said something to that effect.

I said that I do what I want. It's not that I don't follow rules, it's that I do what I want to do.

Has that always been a part of you?

Pretty much, yeah, I'd say so.

Did that cause any tension with corporate roles?

I don't think so — I'm sure it caused tension with specific people, but it allowed me to advance my career pretty quickly. I think eventually it probably caught up to me.

Okay. So how long have you been running your own thing?

Just a couple months.

And how's it going, these past couple months?

Well, I had a goal to pay for one week a month of my daughter's daycare, which is $500, 'cause I'm just starting out, I'm trying not to expect much. But now I'm paying for all of her daycare, which is $2,000 a month, and I've only been doing this for a couple months. So I went from a goal of just get started, to now I'm fully paying for the stuff that I need to pay for in our relationship. So it's going really well.

Yeah, that's huge.

Yeah, it's huge. And I think it has to do with just me being a likable person, honestly, and mustering the courage to talk to people.

Yeah, I think that takes you pretty far.

Yeah, especially the both of those things probably equally so. Before I go on, I wanna say something about the application, submitting applications, not finding anything. I've been freelance software developing for the last couple years, three years or so, and I really thought I wanted to get a full-time job, maybe a year ago or so, so much so that I closed my Georgia LLC, kind of closed the book, and I was like, I'm gonna go fully into full-time work. And the universe had different plans — every interview, every application, I sent I don't know how many a day, twenty, thirty. I'd wake up every morning to a fresh inbox of no's, just like twenty to start the day. It was grueling, and it just kinda pushed me to think, all right, if no one's gonna hand me something, I'm gonna have to create something of my own.

Something that's come up lately is this idea that not everyone can be an entrepreneur — I don't think everyone necessarily has the mindset or desire to do that. A lot of people may not think they have the desire, and then cards are dealt that show maybe this is for you, whether or not you recognize it. But I do believe there are some people who really appreciate a more traditional, stable job, steady income, and then they get to hike in the evenings or camp on the weekends. Do you think you've always been someone who had the entrepreneurial drive, the mindset — yeah, you're nodding your head.

Yes. Always been there.

Why did you not exercise that earlier?

Well, I did — I just didn't mention it earlier, which probably was a mistake. When I moved back in with my parents after college, I started a tech company. It revolved around beer, I got some good traction on Long Island, I was twenty-one at the time.

So you knew beer well, coming off of college.

Yeah, I was drinking, that's for sure. But what happened was I was just too young, inexperienced, and scared. Me transitioning through all those roles was with the goal and intention of owning my own tech company eventually, 'cause I learned the design aspect, I learned products, I learned engineering — I was like, I have all the skills to create something cool. My best idea though was when I was twenty-one, when I did the beer thing, and ever since then I just — maybe it was because I got stuck in these corporate jobs and they were kind of mind-numbing, I don't know exactly what it was, but I kind of lost a lot of that entrepreneurial creativity from a software perspective.

I totally get that. I feel like the entrepreneurial drive has always been there, but I kind of lost — it didn't seem like there was a light at the end of the tunnel with regard to entrepreneurship in the tech realm, and I feel like working in the tech space can really beat you down and burn you out quickly, especially now with what's happening with AI and layoffs.

I actually am quite grateful that I am, coming from the software world, one of the first jobs to really be massively affected by artificial intelligence, because I think if I weren't, I probably would have come to this realization that I need to spin away from a desk job and forge my own path, but it would have come much further into the future — I probably wouldn't be doing this right now. So I am grateful for that, and I feel like that's kind of a common thread of people who've, whether it's been layoffs or quit or they've escaped the kind of abusive relationship of tech.

So you've said you've been an entrepreneur your whole life — this is kind of a manifestation that surprised you. When you were looking for your own thing, what different avenues aside from lawn care were you interested in pursuing?

So I went down the ETA route — which, if you don't know what that means, it stands for entrepreneurship through acquisition, which essentially means you buy a boomer's business. They're retiring, their kids don't want to take over the family business, whatever — so there's a lot of opportunities for people to buy an established money-making machine. The problem I faced was I had a baby, and I couldn't take that risk of buying a multimillion-dollar business, putting down a couple hundred thousand dollars and taking out an SBA loan for the remainder, on the hopes that the transition to new ownership would go well and all the people they built relationships with would stay. Now, I'm a little bit lucky — my wife has a full-time job, she takes care of a lot of the stuff right now, and she has healthcare tied down for us, which allowed me to explore a little bit. But when we were first starting to look, we looked into service businesses, not necessarily a physical-location business of selling something — there's a lot of risk with that. Anytime you invest or want to buy something, there's just a ton of risk. And like I said, I just had a baby — we ultimately determined that we couldn't afford it, or we could afford to do it, but it was too big of a risk if something went wrong. And that left me with two options: either take care of our daughter at home, or go out and bust my ass and try to build something myself. And that's what I did.

For people who are in a space where they're looking to figure out what to do, what to create, what sort of entrepreneurial endeavor they want to take on — do you have any advice for those people to help narrow the focus? Because it can be overwhelming with how much you can do. How do you determine where to point and shoot?

So for me, I kind of looked at it like, well, what are my existing skills? And what are some businesses that use those skills? My existing skills are design and branding, websites, software engineering, management. And you look at a lot of service companies, especially really small ones — the dad's been running it for thirty years, before there was ever any kind of internet — they don't have the ability to brand themselves well, they don't want to spend the money to pay somebody to do it. There's a lot of things in the service world, at least, that fall under that category. So I tried to find something where I could leverage my skills and use that as an advantage — because, I mean, mowing lawns and trimming hedges, anybody could do it, and because anybody can do it, anybody does do it.

But they don't have the skills that can set them apart from the next person.

Yep, and that's kind of where I went. I was like, I could put something together — my brand, I put it together in a week. My marketing is "dog-approved yards" — because I named my business after my—

Yeah, share a little bit about the business — you're wearing the t-shirt.

I'm wearing the t-shirt, and there's a little logo. Business name is Cashew's Lawn Care, it's named after my dog. The shtick is that he's like the owner, and he does all the inspections afterward to make sure it's approved, and I'm just kind of the errand boy that does what he demands. And it's worked — I've had people come up to me and tell me they like my marketing, they like my stuff. I chose bright colors, because everybody in lawn care has green and brown and black, a leaf on top with the words, maybe a line separating them — it's all just boring as shit. So I came in and was like, okay, bright yellow and pink, like a stamp, and make it fun. And it's been working for me.

Yeah. I think one of the ways my mind has shifted as I've gotten older is I used to think that smart people got certain jobs — if you were smart, you'd be an engineer, an actuary, a doctor, a CEO, whatever. And I think now I've realized there are so many opportunities out there, and smart people just know how to leverage those opportunities — whether it's lawn care, podcasting, user-generated content, personal training, health coaching, whatever — there are people who are able to create insane businesses in all of those areas. And obviously it's more than just smarts, there's a lot of pieces that have to come together, but you can really create anything. And I think part of the thesis of this whole podcast is that as companies chip away at employee benefits and wages, and wealth becomes increasingly concentrated in upper management and senior executives, and the average person is struggling — my hope, and what I'm starting to see inclinations of in the market, is that there'll be more opportunities for anyone to open up a business. Do you feel similarly? Do you think there's anything happening in the world today — for people listening who are interested in starting something — do you think there are opportunities today that didn't exist a decade ago?

I think the opportunity is gonna move more toward service-industry things where you have relationships with people. And I'm probably completely wrong, and maybe I'm just looking at it from my personal experience, but corporations — some of them are hiring more people even with AI, and others are laying a lot of people off. But if corporations become too automated, and one person's now doing four people's jobs, then where else can you go? There's only so many, let's say, Metas of the world — there's Meta, Instagram's owned by Meta, Snap is whatever — jokingly, Evan Spiegel, I think, is the CEO/founder of Snap — his LinkedIn title, for a long time, was like "Chief Research Officer of Instagram," because Instagram copied all of Snapchat's stuff, their stories, their disappearing messages, everything. So even that, you could argue, isn't really owned by Meta but is leveraged by Meta, and Meta just continues to scrape features off of it. And then you get Amazon, they dominate the e-com world, TikTok is another one — but we're past the point where these major industries can be improved upon, because the Magnificent Seven are just dominating. There have been people who tried to compete with Amazon — I forget what they were called, I knew people who worked at those companies, but they're gone.

So are you saying that if you want to succeed as an entrepreneur, you should not elect to tackle the beast of one of the massive conglomerates, but instead focus on a more niche area?

Probably — it's a good way of looking at it. It's just hard to compete against the big guys, obviously, and some people do it well, if they get enough backing, if they know the right people — so much of starting a business that can compete with a big company involves just knowing people who can fund you.

Yeah. I also wonder, let's talk about competition for a bit — when you look at other landscaping businesses, do you feel anxious, like, are they gonna take some of my market share? What's going on in your head and your heart?

No, I don't fear that at all — I haven't lost a single customer. And again, so many businesses start off and do well because the person who founded them is doing something right. When you start losing customers — not that I've lost one yet — I'm gonna assume it's when the quality of your service goes down, and the customer's like, well, I'm paying this amount of money and it's not going as well as it used to, so I might want to find somebody new. As long as you can keep up that quality, the customer service, the user experience, then I don't see why you should even have to worry — if anything, the people who are entrenched, who aren't evolving, who don't have that differentiating factor, should worry. Now, my differentiating factor is a brand and my personality — it's not some crazy tech thing, but arguably that's safer, that's more of a moat, I think, nowadays than strong tech is.

A personality?

Yeah, probably — I think differentiation on more human things. There's — you know Rick Rubin, the producer? He's produced every artist who's ever been anyone, he's had a hand in their trajectory. Interesting character — and there's a meme circulating, it was something about vibe coders, and it's Rick Rubin in it, and the interviewer asks him something like, "What do you bring to the table, do you have any skills?" And he's like, "I possess absolutely no technical skills whatsoever, it all comes down to my opinions and my taste." I'm paraphrasing, but he said, "I'm not the best musician, I don't have the technical skills to mix and master better than anyone else, but I have exceptional taste." And I think what's clear with AI is it has piss-poor taste, from a design perspective, from a strategic perspective. And I think it's because — this is getting a little off topic — but I think as a society, in this material world we're obsessed with, we focus so much on the material side of things, the measurability, the quantifiable, the compute side — these AI LLMs are incredibly good at compute, but they lack every other part of the human experience — the emotional experience, the connection to a communal consciousness. They lack the part of us that's involved in decision-making that is not purely computation, logic, and reason. So I say all that because when I'm looking at businesses I like to work with, businesses I want to partner with, products I like to use — obviously the quality of the product matters, but the quality, even for a tech product, doesn't necessarily mean it's the absolute fastest, most performant. Yes, I like my apps to load relatively quickly, but I think there's also a subjective-taste component, where there has to be an intention set by probably a human to steer the technology or the product in a direction that aligns with what other humans want. And I think as we've become so oversaturated with new tech, and a lot of it is just vibe-coded and takes no time to build, the bar has actually not been lowered for quality applications — even though everyone can prompt an AI to build a full-stack application in a couple sentences and push it to some Vercel domain — I think it's raising the bar for the need for high-tasteful applications. And I think that's the same with service businesses and other things.

What's your take on that? You're shaking your head.

I can see where you're coming from — the internet started with the best intentions and then got flooded with crap. The same thing's gonna happen with AI — people talk about AI slop all the time now, individuals building their own applications. What I find interesting, what I've always found slightly interesting about people, is that they get hyper-focused on their specific needs, because obviously they would, they're the ones facing whatever their specific problem is. Now, with the ability to vibe-code, everybody's gonna be able to fix their very specific problems — which maybe is exactly proving your point, everybody's focusing on their very specific problems. So then what is the cultural thing that everybody can wrap around, everybody can get involved in? Maybe that's just a much higher-quality application that everybody could join in on, I don't know.

I guess the reason why I was shaking my head is because my first thought was that people get very specific about their specific problems and don't think about a scalable solution.

Interesting — I almost feel the opposite. When I was working at the startup studio, and the people I've connected with who are interested in starting largely tech businesses, and even ones I've consulted with, usually have too much emphasis on scalability and not enough emphasis on day one. Real quick, I do also agree that the era of SaaS is dead. Or I don't want to say the era of SaaS is dead, because I think there's still a space for SaaS — I think highly regulated things, for example accounting software, I would not want to create my own accounting software. Now, my own bookkeeping software — in fact I did, I built it in two days over a weekend, a little bit Saturday, a little bit Sunday, months ago — a way for me to track all of my non-business expenses, any recurring expenses like rent, this studio space I pay, and calculates that ten percent of my rent can be written off as a business expense — I can upload PDFs of my donations, all that stuff. I built this thing, it's super specific to me, and I don't care about anyone else using it — if no one else uses it, I don't give a shit, it's my own product. And I think there's all these tiny little micro-SaaS businesses that anyone under the sun can vibe-code, and who gives a shit about scalability? Those who are a little bearish on AI, with regard to software development, say, well, it doesn't scale well — and I'd disagree, I think with the right architecture it can, but it also may not have to scale. I don't need to scale this one piece of software to thousands, millions of users — I need to scale it to myself and make sure every month I can put in those lines.

Well, that's exactly what I just said.

Yeah, exactly, so I fully agree that these little micro-SaaS businesses, everyone can just kind of vibe-code their own thing, and I think SaaS is gonna largely evolve because of that. I think it's the people who have the mentality of, "I want to build a unicorn" — which is a funny statement, considering there's — what's beyond a decacorn, is that what they call it, a trillion-dollar company — it used to be everyone wanted to build a unicorn, a billion-dollar company, and now a billion-dollar company seems so meaningless, not to me or maybe you, but in the grand scheme of things, when you think of company valuations now, a billion dollars is a drop in the bucket seemingly. I think for the people who really want to build a billion-dollar business — maybe one percent of the population or less — those are the types of people who are so eager to acquire market share that they focus too much on scale. They're like, I want to make sure we can reach a thousand customers, and I'm like, dude, you don't even have one customer, why do you care about a thousand? Focus on that one. But exactly to your point, for those who are just interested in making their lives easier, those people don't give a shit about scale. For me, I don't want my little budgeting app to go to anyone else — if someone wanted to use it, sure, I'd send it to them, but it's just for me, and I could not care less about scalability. But that's because the business I want to grow is this — I don't want to grow a tech business right now, that ship has sailed, I've realized it's not for me, I don't care to push the tech industry any further, I feel like tech is good enough, there are other people who can progress it who are way more interested than I am, I'll just ride that wave. But I'm happy with tech — it's the same reason I'm looking at an older car, older bikes — I think tech got to a point where it's sufficient, and now as tech quote-unquote improves, it's made my life worse. I don't really want my car to brake for me, I don't want my car to change gears for me, that's ridiculous, why do we have automatic transmissions, that's crazy. So I think there are certain people out there who are more oriented toward growth, who want to build a billion-dollar company — those tend to over-index for scale — and then there's the people who are just — honestly, I love the category of people who are just leveraging all the tech that exists, AI, and building stuff for themselves, and that's kind of what I want the future of technology to be, just custom, building whatever it is you want. Scalability — when people build everything they want to build, they have to worry about the upkeep of it, they have to worry about integrations into things, all this other crap that comes with software, and that's where the scalability aspect comes into play. And what we could see in the next couple years is an overreaction of people's desire to build their own thing, and then as they learn the actual complications of integrating into existing systems — like the government, to pay their taxes — they're gonna be like, this sucks, I don't wanna do this, I'm just gonna pay TurboTax. There could be a big backlash — no, I'm just kind of talking out of my butt right now, but TurboTax is a more regulated space, and I think the average person is probably like, screw that, I don't wanna pay whatever amount of money, I'm just gonna do this myself, and then they're gonna realize how complicated it is.

You said SaaS is dead — I don't think that, I think SaaS is gonna evolve, I think people are gonna experiment on their own for a little bit because they have this newfound power, and then they're gonna realize how much it sucks, and they're gonna go back to the old SaaS model, because the SaaS model will evolve to integrate with AI and all the other things. But you and I both know, as an engineer and a former engineer, that dealing with tech, dealing with integrations, dealing with all the compliance — especially you did HIPAA, I worked on custom accounting software — that shit sucks, and the average person is not gonna want to deal with that. Ninety percent of people are not gonna want to deal with that.

No, I agree. And what I mean by SaaS is dead is that the legacy model of building a business where the technology itself is the moat is not going to survive AI.

If you think about it — is that because people can replicate it too quickly?

I think it's because their own teams can replicate it too quickly. Think about Salesforce — I don't have the stats, I'm not gonna pull them up right now, but Salesforce, for businesses like say Coca-Cola — Coca-Cola does have engineers on their team, but I'd bet the majority of their workforce is not engineering. Coca-Cola is a little weird because the Coca-Cola bottling company licenses and sells out, so under Coca-Cola corporate, I don't actually know how many employees they have — probably far fewer than you'd imagine, because a lot are wearing Coca-Cola on their shirt because they're licensing the brand, not employed directly by Coca-Cola. But let's imagine, under the whole bucket of Coca-Cola, there's some subset of engineers, and they probably use a CRM like Salesforce to handle complicated business use cases. They're spending millions of dollars on a CRM like Salesforce, and some of these accounts are gigantic — one software engineer, a hundred twenty-five to two hundred fifty thousand dollars a year, call it a quarter million a year — that's one engineer. That one engineer, I'm quite confident, within a year, maybe within a couple months, could stand up an entirely custom CRM built specifically to the nuances of that business — even if they're a quarter million dollars, what's a quarter of that, $75,000, you spent for that entirely custom-built — it's not white-gloved, it's exactly what you want. $75,000, not seven million or even one million dollars. So I think there's the old model of SaaS where you rely purely on your technology, you have a Salesforce engineer who can figure out how to make the Salesforce engine work for your use case and tweak it — now you just have engineers who can do that and build things from the ground up within their own organizations. Monday.com has drastically reduced their price because anyone under the sun can build their own CRM in a day.

Have they?

Yeah, a lot of the CRMs have started to decrease their pricing — I've stopped paying for ClickUp for project management tools, it's just not worth it.

Interesting, I didn't know Monday.com reduced their prices.

But I also think, going back to the maintenance aspect of it — I just don't know that a company would want to get something standing, and then that particular employee, the new software engineer working with Claude, would have the expertise to build something from scratch. They might be able to talk to fellow employees at Coca-Cola to get an idea, but they don't know the twelve-plus years of edge cases that have been discovered — there's tons of edge cases all the time, everywhere, every time you think you got rid of them, there's twenty more. So I don't know, it's the kind of thing you're just gonna have to wait and see.

Yeah, a hundred percent, it's all conjecture. And at the end of the day, I do think, like yourself, you're developing this bookkeeping app — that thing's gonna break over time, as new software updates occur on the coding language, and then you're gonna be like, well now I have to maintain this, and now it's just an extra thing I have to do that I don't have time for, and then you're gonna go, okay, well now I need to find something where it's just gonna work, and all that stuff will happen over time, it always does. But I feel like we went down a big tangent.

Yeah, it's a very big tangent.

Let's go back to Cashew's Lawn Care.

I want to hear a little bit more about — what are some of the biggest challenges you've faced, and what are some of the biggest rewards you've experienced?

Well, as of right now, the biggest challenge I faced was just figuring out what it was I was gonna do.

Right, yeah, 'cause you can do anything, and there's — you can get paralyzed by choice.

Yeah, especially when you have all these skills that you didn't have when you were just out of college, and you're like, well, there's this opportunity, or that opportunity, whatever it is — and you do get paralyzed by choice, 'cause you start to think less about the actual thing you're doing and more about, well, how much money can I make off of that — which is very important, money is important, the whole world runs on it. But it's important just to pick something and go with it — doesn't have to be something you're gonna do for the rest of your life. I am sure as hell not gonna be mowing lawns the rest of my life — that's not the goal. The goal is to hire people to do that, and build a brand that can scale to multiple locations, multiple states — that's the big-picture thinking for me. But in the short term, you gotta be okay with doing things that are labor-intensive, and like anybody who starts a business, you literally gotta wear all the hats, and you gotta be okay with that, and eventually you won't have to. Am I even close to not having to wear any hats? No — but if things keep going the way they are, maybe next year I can start hiring people to do the things I'm doing, the skills I have that I enjoy — design, being creative. At the end of the day, a business is all about creativity, whether you like it or not — how do I market, how do I talk to people, how do I convince people to buy something from me — every CEO is a salesperson, that's the creative part, that's fun. Everything else, eventually you can automate, or hire out. So in the short term, it's hard to get over this idea of, am I going down this path, is it gonna be demeaning, whatever — I think you're looking at it the wrong way. The way you should look at it is you're starting a company, and it doesn't matter what it is, it's creative, it's gonna be fun, every day is a learning experience. The thing you're doing to actually make the money maybe isn't teaching you anything, because it's cutting grass, but everything else around that, that enables you to cut the grass, is the learning part — that's the interesting, cool stuff, and eventually you get past the boring mundane stuff.

Did you have any insecurities that were humbled out of you? I'll provide a little context — one of the things I've been challenged with recently is I'm in this transition into a new career, away from software development, and I'm genuinely struggling when people ask what I do, to say I'm a podcaster. I don't really care to go into all the details right now, but I think there are a lot of podcasters who seem to be in it for the wrong reasons — they've brought on worse and worse guests, maybe more popular but not better guests, shifting away from their mission, seemingly clout-chasing — and I also feel like I'm not making any money from this, so it's hard for me to answer when people ask what I do for a living, because I'm not really doing this for a living, I'm not bleeding much money but I'm spending a little on subscriptions and a lot of time. So it's been hard for me to answer that, or maybe I can answer it but I don't feel it. Did you struggle with that at all — did you have moments where you were taking on this new career and people asked what you did, and you felt some discomfort around sharing?

Yes. When I was walking around my neighborhood, trying to stay hyper-localized, with door hangers, and I didn't know the right pricing, I still don't really know the right pricing — my goal was to knock on doors, talk to people, hang up the flyer, and be like, here, there's a price on the back, I went on Google Maps and got the square footage of your property so I already know how long it'll take, blah blah blah. But that was scary, because you're like, I've never done this before — like anything in business, you've never done it before. You have a whole season of podcasting, but you're in a whole new world of scaling it. So yeah, I was definitely intimidated, I didn't have any customers, people would ask what I did, and — but that quickly changed. I went out and was knocking on people's doors — actually, I did that for two days, and I was like, well I just gotta do it. Third day, I did it — first couple doors were a little awkward, I didn't really know how to say things, and then three, four doors in, I was like, I actually like this, I actually enjoy talking to people. It was this very short period of discomfort when I was actually doing it, and all the bad thoughts, all the terrible stuff, was actually before — I just did it, and I was hemming and hawing and making it worse than it had to be. And then I just started knocking on doors, and actually got to talk to people — some talked to me for like twenty minutes, there are a lot of older folks who are like, nobody comes to the door anymore, tell me about yourself, and I was like, this is great, I get some socialization, I get to know everybody in the neighborhood. The way I was pitching myself was, hey, I'm just starting a company, I'm just letting you know I exist, let me know if you need anything. And the crazy thing is that people — because we're having a terrible year to start a lawn care company, for anybody who listens, we're in a drought in Colorado, nothing's growing, everything's super dry and crispy, people didn't actually get their lawns mowed until like a month ago. So I was starting a company in a drought, I wasn't getting almost any positive feedback, I'd hang stuff on doors, nobody's calling, I'd have great conversations but nobody was calling, and at first I thought it was me, my stuff's too expensive, whatever — but the reality was just that nobody needed the work done yet. It kind of screwed with my confidence a little bit, messed with what I thought I built — even though it wasn't much effort, you know, put together a Squarespace, a website quickly, a brand together over a week, it wasn't a huge time commitment, but it was still like, am I just not cut out for this? But then it rained a couple times and people started calling me, and I was like, okay, this is just the weather, sometimes circumstances are completely out of your control, and you just gotta keep pushing forward. So to answer your question, I was definitely nervous about it not really working just yet, and I had a little bit of imposter syndrome, but that went away pretty quickly.

Do you think you'll be able to lean on that experience for future challenges, future feelings of insecurity or lack of confidence?

Yes, but it's all circumstantial and different every time. My life hasn't been the easiest life in the world, a lot of things have happened, but I've always pushed through it no matter what.

What would you say has been the biggest challenge, the most adversity you've faced in your life?

After I graduated from software engineering bootcamp, I got a job at Shutterstock. I was a brand new engineer, wasn't very experienced, I screwed up a couple times, and they eventually put me on a PIP, a performance improvement plan, and I was gonna get let go. During that time, my dad — he was diagnosed with a brain tumor a year before, but he didn't let us know until a year later, and that just happened to line up with when I was put on the PIP. What happened was I kept my job temporarily, I went home and spent time with my dad, he was only alive for a month after that. Every day he would decline more, eventually he couldn't remember who we were, I had to change his diaper, lift him on and off the toilet — it was really tough. During that time I knew I was gonna lose my job, so I went and interviewed while this was going on, and I interviewed at JP Morgan and they hired me. But it was insane — the hardest part was, one time I walked in and my dad couldn't remember who I was, and about an hour later I had a phone interview I had to take. So I had to go in, he couldn't remember who I was, I started bawling, pulled myself together, and then was on a thirty-minute phone call. That was really tough. But then he just kept declining, and — the funny part of all that was when me and my brother were changing his diaper, and later on, when me and my brother were recovering after he passed away, we went to go see a movie, and had a moment of dark, bonding humor about it together.

You gotta find some humor in that experience. I appreciate you sharing.

Well, it's not often I get to talk about that on a podcast — probably won't be the last time it comes up on this podcast. I think I just bring that out of people.

Yeah, people do the same thing with me — I can't tell you how many older guys, guys in general, just start talking to me about their life problems, and I'm just like, yeah, sure, this is my experience, let me know if I can help in any way. It's so weird.

Yeah, I feel like it's kind of a superpower though.

Yeah, I think providing a space where people feel comfortable to share something is really powerful and beautiful, when you get to connect with someone. One of the many reasons I like this job. Do you watch Diary of a CEO at all? It's one of my favorites.

Yeah.

Okay. It's actually — if you go onto the Ambiguous Truth Spotify, there's two recommendations I have — one's for The Creative Act, a book by Rick Rubin, and the other's for Diary of a CEO. Stephen Bartlett's kind of my — it's funny, I've never really had someone in my entire life who I've looked up to as, like, the North Star.

Ever? Growing up playing hockey, I had players I admired — I loved Evgeni Malkin, I felt like he was a good balance of finesse and brutality, skilled but not afraid to fight, unlike his teammate Sidney Crosby, amazing player but a little softer. I had certain teachers I looked up to, certain business-mogul, entrepreneurial-type people I looked up to, but I think Steven Bartlett is someone — I like everything he does, he's such a role model for me, the way he leads his interviews, how empathetic he is, and he's built such an amazing business out of it. Definitely been a huge inspiration for me.

Yeah, he's great, he's wonderful. Let's take it back a little bit before, because I touched on your childhood a little bit, and I wanna know if there are experiences you had as a child — for better or worse, good or bad — that now, looking back, were really defining moments of where you find yourself today.

Like I said, family problems, so doing everything I could outside the house was definitely defining — I was looking for ways to improve and regulate myself.

Something that's kind of come up for me lately is, as I've transitioned — a big part of it is like you said, that you like to figure out your own path. I think in hindsight I look back at a lot of little quirks and personality traits of me as a kid that are shining through really vibrantly today. Like, I don't do well with rules — I do well with rules when I understand why they're there, I don't do well with rules that are obviously arbitrary and bullshit. So I'm wondering, are there any character traits or personality quirks that for most of your life you thought were a downfall or detriment, and now, older, wiser, with a kid, a career, a business, you're looking at them in a different light and grateful for them?

I kind of feel like I've always been almost genetic, the way I am. My mom always likes to talk about how when we were younger she put everybody through a Myers-Briggs test, and we were all — the doctor who gave it to us said, I've never seen more independent people within a family, because we all settled as very independent. I'm an ENTJ, I think that's the commander, or whatever.

I don't know, then — I'm pretty sure that's exactly what I was in college, and I'm nearly the opposite of that now — I think I'm INFP, or ENFP, sorry.

Did you do sixteen personalities, is that how you took that?

I think so, I actually have it on my computer, I can look it up. So I've always been somebody who — I can't think of like a defining moment that put me down this trajectory of, I'm gonna do what I want. You know what, maybe there is — my dad wasn't really around growing up, so I've always had to figure everything out myself. As an example, I helped my mom constantly around the house, because my parents got divorced when I was fourteen, and after that I basically assumed the male role of the household. My brother went off to college, and then it was just me and my mom in a five-bedroom house with eighty-foot-tall oak trees that dropped their leaves every fall, a lot of heavy antiques, just a lot of things. And I didn't talk to my dad after my parents got divorced for like seven to eight years. So I essentially had to learn everything myself, had to learn how to be a man myself — there were a couple people I looked at as role models, Conan O'Brien and Seth MacFarlane, mostly because I needed the humor to get through — they're always positive, always joking, that positivity always made me feel good. So I wouldn't say it was a specific defining moment, more so the reality of what it was like growing up, where I had to always step up and always find the light in things.

Follow-up question, but before we get to that — sixteen personalities is exactly right, and yeah, ENFP, but it evolved a little over time.

Very cool. Yeah, I think it's the perception one, the feeling versus thinking versus feeling, or thinking versus perceiving. I think I just leaned a little more into trying to — it's thinking versus feeling. I think over the last couple years since college I've leaned a lot more into the emotional side of things and using that to inform decisions rather than just the logical, rational side, and that's really been the — it might have been both the T-J switch to an F-P. But I've always been extroverted. It seems like one thing that's come up in various ways is how individualist society is — the US, you're talking about, and Western in general — and you're obviously very independent, your whole family is. Do you feel like that's been a strength throughout your life? Have you had negative experiences with that, where you've struggled? I guess where I'm coming from is, it's easy for me to sometimes curl into a little ball and want to handle everything myself rather than leaning on other people and the community around me. Has that been your experience with being hyper-independent, where you've kind of shut down a little? How have you exercised that and figured out a balance of maintaining that independence while leveraging the help of those around you?

It's been a challenge, 'cause my wife is also very independent — she's moved from job to job, climbed the corporate ladder, all that stuff, so she's also super independent. And it never really caused a problem for me until I had a child, because as soon as you have a child, one parent, or some adult you trust, always has to be with that kid. Me and my wife moved from New York, where my family lives, to Colorado, because we wanted a change of lifestyle, more outdoors — Denver is a place where you can start, you can't really start in New York City or LA, you get the cool culture, the cool nightlife, but when you're ready to get married and start a family, that stuff doesn't matter anymore, and you want to afford a place to live, afford a house to raise a family. So we moved to Colorado to do that, and we got exactly what we wanted — the outdoors, the house, our independence — and then we had a kid, and what we realized, which anybody should realize 'cause it's a saying as old as time, is it takes a community to raise a kid. And we didn't have any family in Colorado, so that's why I had to raise our daughter for the first year and a half — luckily, like I said, I got a nice severance when I got let go, I had stock options, so I was capable of doing that. Most people are not. Daycare costs us two thousand dollars a month, but that being said, I can't tell you how many stories I hear of millennials whose boomer parents don't wanna help raise their kids.

Really?

Yeah, I hear a lot of people with kids — their parents are like, we've spent our whole life working, we've accumulated a ton of money, we wanna go on vacations all the time, we don't really wanna spend time with your kid. And I'm not saying my parents or my wife's parents are like that, I'm just saying that's what I hear and see — there's a world right now where this hyper-independence, when you have a kid, becomes incredibly difficult. I'm not trying to deter anybody from having a kid, they're wonderful, I love my daughter, but that's when I realized my hyper-independence was actually a detriment, because now I've established a life over here, and my mom and my wife's parents are in Vancouver or New York, and in order for us to do anything, just to work, we have to spend two thousand dollars on daycare — now some person who develops a relationship with our kid is seeing a lot of the firsts, or if we want to go on a date, we have to spend a ton of money on a babysitter, it doubles the cost of the date. We found some ways around it — we've made friends with other parents who've watched our daughter so we could go to dinner — but two and a half years of doing that, it takes a toll.

Yeah, it takes a huge toll on you, or any millennial who has to do it, any parent who has to do it — unless you're a parent that doesn't give two craps. It's crazy to hear that there are grandparents who don't want to be there for their grandkids — my first reaction was, holy shit, I can't believe that — but I have some unpopular opinions on the nuclear family and a lot of challenges with it, and things I don't love about it, and obviously the whole podcast isn't built on the belief that corporate is best, and something that really irks me is when someone has a goal of retiring at sixty-five and they're just gonna grind and hustle until they get there, because how can you know what your life is gonna be at sixty-five, how can you know if you're even gonna make it to sixty-five — and if you make it to sixty-five and you now have grandkids, and you allocated your mid-sixties, early seventies to travel, you have to make the decision between traveling the world with your partner or spending that time with your grandkid during the earliest, most formative years — that's a horrible decision, I don't want to have to make that decision. And tying back to the purpose of this podcast and this episode, that's something I deeply feel — I don't ever want to create a goal so far in the future, sixty-five for example, that I orient my entire life around in hopes of achieving it, because even if you get to the finish line, right, even if you retire at sixty-five and have money, who knows what else is gonna change — grandkids, health or lack thereof. It's crazy to me that we've been encouraged, at least for me, my entire life, my early career, to aim at that, and you're already seeing that breakdown, you're already seeing grandparents who are unwilling to spend time with their grandkids, and it takes a village for a reason. That is absolutely wild to me.

Well, to go back to what you just said, my dad is an example — he worked his entire life with the intention of retiring, and he got the brain tumor at fifty-nine, so that's actually someone that shaped me — he didn't even get a chance to enjoy retirement, or anything, 'cause — yeah, he's dead. It's crazy. My roommate and I were camping south of Steamboat, on the Colorado River — there was a gentleman there, seventy years old, camping next to us, and we got to chatting, and he was just talking about how he paid his dues, worked, did his thing, and now he's retired at sixty-five and living the best life, and he's like, so just do that. And I couldn't — I'm not particularly good at hiding my feelings, I wear my feelings on my sleeve, if someone says something that rubs me the wrong way, I'm not gonna pretend it's all hunky-dory. But the whole time he was saying that, I was thinking, I'm truly grateful he's had such a positive experience following that path, but it hit me — that's the first time I've ever heard someone say they're glad about it. I haven't really heard many people of that generation express gratitude that they took that path, and that shaped me — that's been a big reason I've decided not to take that path, and I'm really trying to figure out the balance of still striving for a goal, and I don't even know if retirement's the right word, but financial stability for the foreseeable future, while also wanting to figure out how to enjoy life now. And I think that's a big reason I love Colorado — I find a lot more people out here who are really trying to savor the moment, be grateful for what we have, and it's a lot easier when you have weather like this, it's beautiful outside, blue skies, really hot but nice warm weather, you're working outside all day, it's not too hard, nice tan to prove it.

And some freckles.

Yeah, I've been avoiding the sun at all costs, it's so hot, the sun is piercing, I always wear full pants and sleeves when I'm outside, I can't do it, it's too hot. But anyway, I think that's shaped me a lot — seeing people who have not been able to experience the goal and luxury of retirement, and you get so many people who have experienced retirement and they just quit — they quit moving their bodies, they quit moving their minds, and they start to go downhill so rapidly, and they thought they were gonna live, healthy at sixty-five, gonna live until ninety-five, and then seventy rolls around, they haven't done shit for the last five years, their body's disintegrating, their mind is disintegrating — I don't think we're meant to do that. There's a lot of things we're encouraged to do that I'm starting to see examples of not working all that well in the long run, and that's one of them. Just the whole notion of retiring and never working again, and just sitting in front of a TV on the couch for hours on end, or even sitting on a beach for hours on end — I don't think it's really doing you any good, you're gonna probably lose a sense of purpose and meaning in life too — now maybe if you have kids or grandkids you can regain some of that. I think from your perspective, you're viewing everything from the point of view of not having kids, and as soon as you have kids, if you have kids, it totally changes — not like an immediate light switch, but you start realizing all these things.

What are some of those things?

So Cashew's Lawn Care, mowing lawns, not the most exciting or incredible thing to be doing ever — some people view it as demeaning, but at this point I don't care. Like I said earlier, I'm very driven, I oriented a lot of my career choices around eventually owning some tech company I developed and becoming a millionaire, multimillionaire, whatever — and then I had a kid, and I was just like, I don't care anymore, I just wanna make some money and spend time with my daughter. That's one thing. Another thing is you get a lot of satisfaction out of watching your kid grow — everybody says this, it's no surprise, but you don't actually know until you have one. It's basically all the things you've heard your entire life about having a kid, that you don't believe until you have a kid.

Well, I think that's kind of my point too — I would hope that everyone, regardless of relationship status, family, kids or not, still recognizes that work is a medium through which you can create value in the world and capture some of that value through money, and afford to create the life you want, for yourself, your offspring, your spouse. I think where I get caught up is when people become too milestone-oriented, and rather than looking at their lives today and saying, what do I want now, how much time do I want to spend with my kids, my partner, my friends, my community, they say, well, I'll spend time with them in the future, when I'm sixty-five, when I'm retired, I'll travel when I'm retired — you may not get that chance. But I can't blame people for thinking that way, 'cause money is what enables all of it — why must we feel like we need to sacrifice today for some unforeseeable future tomorrow? Let's look at the stock market as an example — compounding interest — this is something I got advice on from corporate people, put as much money as you can into your 401k, I maxed it out for many years, and now I'm thirty-seven — thirty-seven in a couple weeks, July eleventh, seven-eleven's my birthday, free Slurpees, great little birthday gift. I got a bunch of money now, which is partly what enabled me to take this risk on making a lawn care company — but I never would have been able to do that unless I took the advice of stashing away money during a lot of my prime earning years. That being said, I think part of what happened with the boomer generation is they were living under the teachings of their parents, the Silent Generation — Great Depression era. Have you read about the Great Depression, what caused it — it was essentially a lot of corruption, no rules or regulations, the Securities and Exchange Commission didn't exist yet, so it was basically the Wild West. So the Silent Generation taught the boomers, don't do stuff in the stock market, don't really invest, keep your money, preserve what you have — which is why millennials inherit from their boomer parents basically an attic full of crap. Now we're millennials, we're in the information age, you can learn anything on the internet, and I know a lot of millennials, people our age, are not doing it, but investing early — and this is why our parents didn't invest early, they didn't get into the stock market early, so many of them are now living very meager lives, tons of people in poverty, they had a lot of fear with investing — they're now in their sixties, not working, living very meager lives. Us, on the other hand, we've had a lot more information — what our parents told us to do never actually worked for us, go to college, get a ton of debt, so on and so forth. So at least some of what I did was forge my own path, and do a lot of things that seemed risky — starting my own tech company, going to a bootcamp, doing stock market stuff — all this stuff has enabled me, now in my late thirties, to really create my own life as opposed to being a slave to a corporate job. But that came with a sense of trust in the people who'd been doing it beforehand, a sense of adventure, a sense of risk-taking — which, us as guys, we have a more risk-taking appetite than women, thank you testosterone I guess.

I hear you, and I'll reverse this framing you shared earlier, which is, I'm coming from the lens of not having kids, and you're coming from the lens of having kids — a wife and a daughter, your tolerance for risk right now is far lower. A couple things here — firstly, you cannot take a shot in the dark as much as I can, because if this fails, okay, I go back to software, I go back to PMing, something more tried and true, I'm only supporting myself. Different people have different risk tolerances intrinsically, and there are external factors that require your risk tolerance to be modulated — family's a great example. Also, having had corporate jobs and been able to put money into retirement and save up, I have a bit of a stockpile, and having had income through software development for the first six months of the year, I have a little money in my business account I can take distributions from when I need capital in my personal account, if there's no revenue generated from this for however much time. So I definitely understand where you're doing the risky stuff, testing the waters — early in a career it wasn't very risky, it was 401k, somebody else manages it for you — by being able to save your money, put it into a portfolio that's going to grow, accumulate interest that compounds over time, you're able to take on a little more risk now. But for people in a different situation, who have the tolerance for much greater risk today, like myself, not having a family or a child, it's a lot easier for me to take on risk today to get to my dreams. And I'm willing to sacrifice however much the known upside is from putting money away from a salary job into the stock market — eight, ten percent a year — I'm also not really banking that the stock market's gonna keep going up over the next however much time, I wouldn't be surprised if we see a massive bubble burst and plummet, I don't really care to put more money into the stock market right now, if anything I'm interested in finding other markets to move my money to, non-US equities, trying to figure that out right now. So my point here is I'm willing to risk, for lack of a better term, foregoing all the future stock-market appreciation of my assets for the potential reward of doing something I actually want out of life in a more subjective way — because I think there's richness in terms of finance, monetary wealth, but there's also richness in terms of social wealth. And I think because I have more time on my plate, I'm able to pour more into building social wealth, building up trust within the network — like, Anthony's a good guy, hopefully, who might have connections that can help you, who's gonna give you the time of day to sit down and chat. There's that wealth, there's all these different categories. And I think when I'm looking purely at the financial piece, yeah, I can look at the numbers and recognize that putting money into the S&P, which has historically done twelve percent annually on average over the last fifty years, would be a worthwhile investment — but I'm also willing to make the financial sacrifice today to pursue something I think is more enticing in the long run, and potentially has higher upside too. With running your own business, there's tremendous opportunity for upside, there's not as much upside if you have a more traditional career. And the other thing is, my buddy, a little older than me, been working ten years in the workplace, did the simple calculation of, is my bump in pay — software engineers, well — is it keeping up with inflation? He's making less money today than he did when he first started ten years ago.

What? Yeah, that's crazy.

Yeah, that's the reality of it. But I hear what you're saying — to go back to my original point, you were talking to boomers and saying, why sacrifice your whole youth for this maybe-someday thing, what's the point of planning for the future, kind of what you were getting at. And it all depends on how much money you're making, in my opinion — I think saying, why plan for the future, is a bit reductive, it's not that you shouldn't plan for the future. What I can't wrap my head around, and this might just be my own personality or brain, is it's very difficult for me to aim toward a sure, mediocre future, compared to an unsure, potentially exciting one. I don't even know what it looks like, but I know that in this direction there's something a little more spicy and enticing, and that's something I can orient myself around much more easily than a known mediocre future.

Sure, and it all depends on where you are in life to be able to do that — I personally am capable of doing this because of the early sacrifices I made. Instead of going on crazy vacations with friends, I socked that money away. Instead of affording an apartment in Manhattan, which I could have done working at any of my tech jobs, I lived an hour out on the L train with four other roommates, and spent seven hundred dollars a month — those were sacrifices I made, even though I could've afforded other stuff, but doing that is what enabled me to do what I'm doing now.

Totally — and here's a little framing I'll plant, which is I think it comes down to investment. You chose to invest in yourself at a young age, through a job with a stable salary, where every month you could understand the delta between what you need to survive and what you want to put away for some future risk you may take — which is what we're seeing today.

Yes — and I think that was also my mentality when I first graduated college, actually. When I first graduated I also did a startup, wasn't making any money, was working at a brewery to pay the bills, so there wasn't much saved. But then once I got my first real salaried corporate nine-to-five desk job, I was like, okay, great, I can save, because what if in the future I want to do something risky? So I put away money, and I also switched jobs, from PMing to software engineering, just shy of tripled my salary basically overnight, didn't adjust my spending habits at all, just put more into savings, which was a great choice. But then I realized, I don't know what I want to invest in, in terms of a business risk or entrepreneurial risk, but I did know I wanted to invest in myself. And that's when I stepped away from that job and took time off to travel — that was the decision of, I don't really know where I want to take my life professionally, but I knew I wanted to invest in myself in some way, which was a bit more exploration, travel, gaining wisdom and worldliness and global experience. So I think we're aligned in that — what it comes down to is, when you're in a chapter of life where you're content with what you're doing, you know you have — you may not know what the goal is in the future, no one knows what the future holds, but you know, all right, I'm really happy with where I am today, I want to save, I have this amazing opportunity of having a stable income, this delta between my income and expenses, and going to stockpile and save — wonderful space to be in. And then once you're in a place where you have that external driver, of being fired or with a severance, or an internal driver of, I just want to stop doing this and chase a moonshot — you have the luxury to pursue that, and okay, I'm ready to actually take the plunge and do this thing.

Yeah. What has been the biggest lesson you've learned from entrepreneurship that you didn't learn in a corporate environment?

This is gonna sound really weird, because I'm sure a lot of people aren't gonna say this — how easy it is to get started. I think a lot of people hem and haw about — I was saying earlier in the conversation, I was hemming and hawing about knocking on somebody's door and talking to them, but then I did it, and it was easy. I think people get really caught up in overanalyzing — I've watched tons of people online, like Cody Sanchez is a great example, I'm sure you've watched some of her stuff, she talks about boring businesses all the time, and breaks down the numbers, and loves when people just start with what they have in their house, go perform some task, and it just snowballs after that. That's essentially what I did. I think people get too invested in, is this thing gonna be perfect, am I gonna put myself out there and somebody's gonna judge me — which is definitely a fear, but at the end of the day it doesn't matter, you still have to do it, it doesn't matter if some random person you meet thinks it's stupid — now, if you get enough of that, you may change your mind about your marketing material, or how you're presenting yourself, but that's all just learning, that's not you as an individual. Just going out and trying to do something for yourself puts you way ahead of most people in this world — most people think they need a job, they don't want to invest in themselves, they're afraid of doing anything outside the norm. But just having the ability, or the desire, and then trying, puts you lightyears ahead of other people. And investing in yourself is one of the most important things you can do — I have not had one outcome where I've invested in myself and it turned out poorly, ever. How easy it is to start — it's literally just starting and doing it, it's the easiest thing but also the hardest thing, because you have to get over your own mental hang-ups, and then, it'll be tough at first because you won't be pulling in the money you want, but it'll snowball, and you'll eventually succeed. So much of it comes down to people who give up and people who persist — and there's definitely a point where you should give up, if you're trying for months and months and there's literally no movement in any positive direction — I'm not saying you have to make money in those months, but if there's just no movement at all, you're reaching out to people, nobody's responding, maybe it's not the right thing for you — but that doesn't mean entrepreneurship isn't right for you, it may just mean that particular thing wasn't right for you, which I'm sure you and I ourselves have been through, trying different things that don't work and moving on to the next.

Yeah, I feel that — I think experimentation is absolutely critical, and I've never seen anyone get anything right the first time with a business — you could argue Amazon kind of nailed it selling books online, but they knew that was gonna be just an avenue into everything else. Right, it's simple but not easy — starting is a simple concept, you know where to go, but it's hard from a motivational, energetic perspective, of getting off the couch and doing it, getting rejected.

Getting rejected — it's hard to get over being rejected. Well, that's what ninety-nine percent of life is, is rejection — the sooner you can get past being afraid of being rejected, the sooner you'll succeed.

Have you had any rejections with the current business that have really set you back, or do you feel like you've been able to take them in stride?

I think when I was trying to figure out pricing, and nothing was working, I got rejected once or twice, and it started making me question, is my pricing right, am I gonna make enough money doing this — but then you get your first customer, and you're like, okay, let's see what happens, and then you get the next one, and everyone's been referring me to everybody, which is great. I don't know, there's just — you don't know until it starts working, and then every micro-adjustment — I shifted my prices down five bucks from what I was thinking they should have been, which was fine, I'm okay with taking a little bit of a hit the first year in order to build up a customer base and reputation, and next year I'll change that — it's part of the price of starting something. Micro-adjustments are important, you can't be so hard-set on something, you gotta be really flexible. Coming from the tech world, we're talking agile methodology — if you don't know what it is, read up on it. There's a great book called The Lean Startup, all about proving the concept with as little investment and work as possible, and then once you prove the concept, you actually make it real — but proving the concept means a lot of small adjustments to make sure it works, so the more small and agile you can be, the better. With lawn care, I'm still using my Ego mower, my home mower — I upgraded my blower, because I had all-electric equipment and was running into an issue where I could only hit three yards before I had to go home and recharge everything. So I identified what was taking up the most battery, which was the blower, and I got a gas version of that — that was my first actual business expense besides a website and some door hangers, and my t-shirts. I started this business with like $400 — that's it.

So is it fair to say it matters less that you get it right, and matters more that you try to figure out what is right? Is that kind of what you're saying — like, you have to get it right eventually?

Yes, but you will get it right through trial and error, so eliminate the fear that you're gonna get it wrong the first time, because you definitely will — you'll get it wrong many times, and then eventually it'll just start working, 'cause you'll do all these micro-adjustments about how you talk to somebody, what you say, maybe a slight price adjustment, how friendly you are — or you talk to somebody and you automatically know it's not gonna go well with them, so you just move on quickly and get over it. It's all about these micro-adjustments, to get to a spot that's really working for you.

So do you have a long-term vision? Can you paint me a picture of what you want this business to become?

Sure — I want this to be a multi-location, multi-state thing, I'd love for it to be a franchise, there are only a couple franchises in the lawn care world, I don't see why I couldn't do it. I spent a lot of my career building systems, brands, and user experiences, so I'm in a pretty good place to develop all those things, which is essentially what a franchise is — a brand and systems, and then you sell somebody the right to use that brand and those systems in their own location. So eventually I'd like to get there, hopefully in a couple years, and then I'd like to continue learning everything I can, but also sit back and enjoy the fruits of the labor.

You sound like someone who's very much a long-term thinker, willing to make a short-term sacrifice for a long-term objective. Have you seen that pay dividends in a different way with respect to entrepreneurship compared to corporate life — do you feel like that mentality has helped or hurt you in the entrepreneurial world?

I think it helps — any time you have to start off small, and then make some sacrifices in order to build something. I also think part of it's just my mindset — I don't think everybody has that, there's a lot of people who just want to make what they want to make, a hundred, two hundred thousand, whatever, and then that's it, they don't want to think about it anymore, and they'll do what they need to do to get to that position. I don't think that way, I think in terms of scalability and making things bigger and making more money — not that I need all the money in the world, I don't need to be another Elon Musk, he's gonna be the only one that rich for a very long time I'm sure — but at the end of the day, if I can get to a net worth of five million bucks, I'll be set, and I won't need to do anything anymore, I can just enjoy life, which is my goal. Because at that point, you were talking about ten percent returns, the four percent rule — essentially you just take four percent out of your brokerage account every year and it still grows, because you're still making six percent — and four percent on five million dollars is like two hundred K or something. So if I can get to that point sometime in the relative future, I'm more than happy to just stop, sell whatever I need to sell, enjoy my life with my daughter, my wife, if we have another kid, go on vacations — basically do whatever we want. I don't need anything else than that. So that's the goal — franchise in order to get to a certain monetary amount we have in mind, and then just enjoy life, go fly fishing a lot.

Yeah. Why do you think we have this concept of growth for the sake of growth — it's come up in conversations recently, and it seems like the world is dominated by people who just see growth as intrinsically good. I'm not sure I understand why there's so much emphasis on growth. Now, there are certain forms of growth I think are intrinsically good — personal growth, I don't think you should ever stop growing as a human being — financial growth, that's interesting too, on a macro level we're a country oriented pretty much solely around GDP growth, that's the number that's the North Star, there's nothing else that matters in the US than economic growth, seemingly, and in individuals it seems like there's a particularly intrinsic understanding that growth is good. You do not seem to adhere to that — you understand there's a cap. Why do you think growth is not intrinsically good, why do you want a cap and not just continue growing in perpetuity?

Because I don't need it. It's not that I don't think growth is bad, growth is good.

Why is growth good?

Well, it shows you're moving in a positive direction as opposed to a negative one — before the US was the global reserve currency, there were, I don't know, twenty other ones, and all those countries have peaked and started going down, and everybody in that country is not doing as well as they would have been. It's the same in corporations, same anywhere — growth is good because it shows you're doing well as an economy, a country, a company, an individual.

Yeah, but growth isn't sustainable in perpetuity, it's never been, in the course of history there's always been growth and then a collapse, growth and then a collapse. So I understand you don't want to see an economic downturn, but it also seems the only possible outcome from growth is a downturn — whereas if sustainability were the North Star, as opposed to growth, that would in the long run be a far more optimal solution, because growth has and will always lead to shrinkage, usually a very abrupt one. I'm still confused why growth is seen as a positive — I get that growth means up, and up means plus, down means minus, but I'm still a little confused why that's inherently a good thing and what we should aim for.

The other thing I can think of is maybe it has to do with population growth — you look at Japan, they're headed — their population, the amount of young people, is collapsing, and not only is their population declining pretty abruptly, it's also consolidating into the major cities, Tokyo, Kyoto, Sapporo's getting more concentration — they're literally giving away homes and land to foreigners.

That's crazy.

Yeah, that's not great, at least for the Japanese economy — but if your population isn't growing anymore, or at least sustaining itself, your economy collapses, because the amount of working people can't support the amount of retired or older people that need support. So how do you sustain that? There's a fine line between growth and decline — keeping things sustained means everything has to be going a very specific route. Growth is like there's a million routes between here and here, sustainability there's only one, and decline there's a million things between here and here. So maybe growth is just easier to imagine than sustainability, because so many things have to go right with sustaining something as-is, and it isn't sustainable if you have a population that's growing but an economy that's shrinking — you're spreading fewer resources over more people. But I mean, that's happening right now with just people being super greedy, up top — did you see what the CEO of Anthropic said a couple days ago, that it's likely we're gonna experience the first time there's an increase in unemployment and an increase in GDP?

I believe that. That's crazy, that's terrifying. Well, Andrew Yang was saying they should tax AI workers and not human employees.

Ooh, interesting — or at least not up to some income bracket of workers, whatever the details are. But the point of taxes is to discourage you from doing something, so if you want to discourage people from losing their jobs, tax AI. I don't know, could be a good idea.

Yeah, it could be. Wild — all these things are enticing in conversations like this, and then in the real world everything has these wild unintended consequences no one can foresee. It's so complicated.

Yeah.

What do you think has been the best piece of advice you've experienced in your career, that you feel like you've been able to leverage through the transition from corporate to entrepreneurship?

In software engineering, or in your career in general, it's always about learning your next thing — it's the same thing in business, or being a company owner, you're always learning. I'm sure that's not as exciting an answer as you were hoping for, but I think it's that simple.

Totally. Last question I'll ask — do you have any advice for people who are interested in delving into the entrepreneurial world, starting something of their own, chasing a passion? What would you share for those people?

Surround yourself with people who are also doing that. When I first moved here to Colorado, about three and a half years ago now, pretty shortly after I joined some entrepreneurial groups in the neighborhood, and that really gets you in the mindset — it doesn't happen overnight, you just start becoming friends with these people, and they start talking to you more, and you get more excited about it, and eventually you're like, okay, I'm gonna try something. I don't even know what the saying is, but you are the sum of the five people closest around you — if you surround yourself with people who are just sitting on their butts, smoking weed, and playing video games, then that's what you're gonna do. If you want to start a business, get involved in those communities.

Wonderful. So if anyone needs some lawn care, where do they go, tell us where to find you.

Cashewslawncare.com. But you have to be in Denver.

Yeah.

More specifically, the west side of Denver, for now.

For now, cool. Well, thank you so much for your time, John.

Thank you for having me, I hope this was a good conversation.

It was. Cool.