Founder of ModernPM. Run Firm Studio, helping other founders and businesses launch and scale. Fight entropy. Enjoy the mundane.
Atlanta, via Houston
Joined March 2008
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@cursor_ai how does one submit an issue? We are getting some weird happenings across our team account. Ie showing we have plenty of room in tokens but some devs are hitting usage walls while its showing them only 40% used for example
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My first advice to a want-to-be founder: have no debt.
Do you have to be rich to start a company?
No. But your personal burn needs to be low.
No mortgage. If you rent, have 20–30 months of expenses saved. No country club. No car note unless the money's sitting somewhere else. Simple vacations. Private school for the kids? Sure—if you have it stocked up.
This goes against some other people's advice. They like their founders desperate—so if it doesn't work, they're destitute.
That's not motivation. That's a trap. Especially if you have a family.
I've found that carrying no debt is a major unlock when it comes to doing what's best for my team and the companies I work with. It helps if you don't have to chase a quick win or get fresh funding in order to keep a paycheck.
The whole reason to become a founder is to work for yourself. But if you're carrying debt and a high personal burn, you'll inevitably feel like you work for everyone but yourself.
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You get APIs!
You get APIs!
We built our APIs for firms, not marketplaces.
This API exists to serve your firm’s needs, not to fuel an app marketplace or monetize access.
If you’re connecting systems, automating operations, or building internal tools, the ModernPM API is designed for exactly that.
Hit us up if you want to learn more.
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Indifference is the Enemy
You and I have believed a lie.
That this would be easy.
This = life.
Single life.
Marriage.
Divorce.
Kids.
Work.
Caring for aging parents.
Finding purpose.
All of it.
Somewhere along the way, we picked up the idea that if something is right, it should be easy. We ran with that lie and turned it into a barometer—one we now use to judge our pursuits.
Where did we learn that?
It’s not in nature.
Spend fifteen minutes in the woods and you’ll see it clearly: everything is trying to live. Everything is struggling. Everything is trying to eat everything else.
For LinkedIn’s sake, I won’t get into where I believe this lie actually came from.
But I will say this: the least happy people I know are under the constant yoke of chasing an easy life.
Here’s the picture that keeps coming back to me, especially coming out of the holidays: building a fire.
The holidays are perfect for sitting next to a fire and thinking about life. Many homes now come with gas fireplaces—fake logs, instant flame, zero effort. I had one for years.
I almost never used it.
Why? Because it wasn’t satisfying. It was easy—literally a flip of a switch—and yet I never used it.
Now I have a wood-burning fireplace.
I have to saw logs. Split wood. Haul it inside. And fight for the return of my man card every time I try to light the thing.
It’s work. It takes preparation. There’s nothing easy about it.
And yet—I burn a fire every chance I get.
If wanting easy, and getting easy, doesn’t satisfy, that should tell us something.
Easy is the wrong barometer.
When easy is the goal, difficulty feels like failure. So when things get hard—as they always do—we quit. Or worse, we become indifferent.
Indifference becomes the compromise.
Neutrality—watching from the sidelines—becomes the easiest posture to take.
It’s easier to let someone else do.
That’s why we scroll.
Why we flip from video to video of other people living, building, risking.
We eat chips and watch people exercise. (Sports.)
Watching other people do has become the new version of easy living.
And it’s killing your soul.
Indifference becomes your default because you were taught that ease was the measure of a good life.
So you end up delegated—to the couch, to the feed, to a life of scrolling.
Don’t let indifference win this year.
Cheers to the doers.
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Living in the Age of AI: AI is the Atomic Bomb of Business
In 1948 C.S. Lewis (I named my dog after him - Clive) wrote an essay “Living in an Atomic Age.”
(Link in comments – read it. It’ll sober you)
He opens with this:
“In one way we think a great deal too much of the atomic bomb. ‘How are we to live in an atomic age?’ I am tempted to reply: Why, as you would have lived in the sixteenth century when the plague hit London every year, or in the Viking age when raiders might cut your throat any night; or indeed, as you are already living in an age of cancer, syphilis, paralysis, air raids, railway accidents, and motor accidents.”
Next paragraph, first line:
“In other words, do not let us begin by exaggerating the novelty of our situation. Believe me, dear sir or madam, you and all whom you love were already sentenced to death before the atomic bomb was invented—and quite a high percentage of us were going to die in unpleasant ways.”
Now pivot to AI trite as it seems.
Your business and your job were already going to die. All businesses die. That’s capitalism, and it’s beautiful. Life implies death—deal with it.
Everyone’s talking AI right now. The more certain someone sounds, the more narcissistic I find them.
Your business has always carried threat + opportunity. Nothing new here.
Lewis’s answer to the bomb?
“If we are all going to be destroyed by an atomic bomb, let that bomb when it comes find us doing sensible and human things—praying, working, teaching, reading, listening to music, bathing the children, playing tennis, chatting over a pint and darts—not huddled together like frightened sheep thinking about bombs.”
The market eats the status quo.
If AI can kill your business, it was already fragile. They were coming for you before AI showed up—they’re still coming.
Printing press, telegraph, steam engine, microchip… every ‘new thing’ shook the world. You’ve never been safe. Now it’s just obvious.
Count it a privilege that you get to live through this.
So to every business leader I know, channeling CS Lewis:
So when AI finally comes, let it find you doing real work: serving customers, building things that matter, making hard calls, helping your team navigate tough situations.
Not doom-scrolling or pontificating about things you can’t control.
Step onto the field. Play the game. Live with the outcome.
Cheers to the Doers!
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Some companies reveal what they ship.
Others sell a roadmap.
One builds trust with momentum.
The other buys time with promises.
Just wrote about this split — and why roadmap hype is getting risky.
🔗 bit.ly/roadmap-hype-machine
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Optimization makes you fast. Optionality keeps you alive.
We chase efficiency, but when everything runs through one system, one vendor, or one perfect plan… fragility creeps in.
Leave some slack. Build resilience.
If it breaks, you should still survive.
Full post here ⬇️
linkedin.com/pulse/optionali…
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I’ll admit it: I’ve got FOMO over all the private equity roll-ups.
Every week, someone’s buying up another niche — vets, dentists, laundromats — time to do my own!
But since I can’t outbid the big boys, I’ve started researching *new verticals.*
Here’s my hit list of future roll-ups — hit me up if you want to be an LP!
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1. Pawn Shops
We start local.
Acquire every pawn shop within a 30-mile radius until it’s impossible not to do business with me.
We’ll use AI-powered sentiment tracking to monitor life events — DUIs, divorces, bad bets — and offer “custom liquidity moments” in people’s darkest hours.
Call it *compassionate capitalism.* Or don’t. The algorithm doesn’t care. IRR 27% with lots of perks - jewelry, guns, and used janky trucks.
2. Horse Barns
You laugh, but where I live, horse barns are everywhere.
Every wealthy parent’s kid “does lessons” there.
If we own every barn in a 50-mile radius, we own the weeknight + weekend schedules of the local elite.
We’ll double prices, apply machine learning to identify the most profitable horses, and launch Stickr — a next-gen glue startup turning equine inefficiency into shareholder value for the bottom 1/3 of horses that don't make the cut.
3. Goat Yoga Studios
The logical merger: horse barns + goat yoga = multi-species wellness.
We’ll sell “cross-species mindfulness retreats” at premium pricing and tout *inter-animal synergy* in our investor deck.
4. Farmers Markets
The ultimate local monopoly.
Buy every farmers market within 100 miles, basically vertically integrate kale.
AI will forecast which vegetables, candles, tamales, and necklaces trend with which demographic and weather trends.
We will also put the farmers market on the block chain where people will need to convert their USD to *FarmCoin*.
5. Haunted Houses
Seasonal fear is under-monetized.
We’ll roll up haunted houses nationwide and reopen them as year-round political fundraising opportunities.
***Hit me up if you are interested in becoming an LP!
Targeting -100% to 42% return in year 1, to the moon after that.
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Uruguay: The Country That Makes No Sense — and Why I Doubled Down
I turned to my close friend and business partner, Fino, and said, “This country doesn’t make sense.”
Uruguay sits quietly between two giants—Argentina and Brazil—yet feels like neither. It’s calm when it should be chaotic. Orderly when logic says it shouldn’t be. To an outsider like me, it’s* defiant in its simplicity.*
The more I have spent time there and with people I have realized: that’s the point.
Uruguayans don’t walk around thinking they’re special. Many even call themselves boring. Their unofficial anthem says it all: Nadie es más que nadie—“No one is more than anyone else.” No flash, no chest-beating. Just steady pride.
Then Juan, one of our team leaders, introduced me to a phrase that explains it well: garra charrúa.
I have a hard time pronouncing it, can't get the rolled R's right! The literal translation—“Charrúa’s claw”—honors the indigenous who refused to give up...but the translation, or attempt to understand by googling, doesn't do it justice.
You start to understand it after long meetings, shared meals, a few too many drinks—and the way people show up again the next morning, ready to go. It’s grit. Resilience. Fierce loyalty disguised as calm.
People ask if I outsource my development.
My answer - No, my team is in Uruguay.
I’ve played the outsourcing game before—and paid the price. In the world of outsourcing there’s always someone ready to cash out at your expense. I’ve lost a few condos’ worth of money learning that lesson.
So now, I don’t outsource. I build teams.
Mine just happens to be in Uruguay (with Argentina and Brazil as a bonus).
These folks have my back. Through hard times, good times, missed flights, and late-night scrambles—we’ve built something solid. I’m all in. Doubling down, even.
I’ve even got my closest friends using my team now to build their software - thats trust.
I’m proud to have these people in my corner.
Gracias, Eagerworks.
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It's wild how many people wait for life to happen to them versus happening to life. No matter your world view, taking an action oriented view of life will serve you + people you love well.
I am convinced the education system is partly to blame for this mindset in the west.
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Balance Sheet Warefare
Capital is creeping into every nook and cranny of the economy. Private equity mostly, but venture too. It’s wild where you find it lurking.
We’ve all heard about the HVAC shops, plumbers, and fence companies getting bought up. But I play in the software world, and the shadows are lengthening into niches I never dreamed of.
I recently heard about a niche, ultra-specific software company—funded, burning cash, running the land-and-expand playbook. I never thought I’d see venture money flow into such an odd corner of the market (leaving the name and space out intentionally), but here we are. A close friend of mine is up against this company willing to lose money hand over fist just to win logos. Most of us, especially bootstrapped founders, have enjoyed the low visibility of niche software. That cloak is gone. Bigger balance sheets, higher burn rates, and the ability to stomach losses are now standard weapons.
The best product or team doesn’t always win in the short run. That’s always been true. But these balance sheet wars can last a while—so what’s a bootstrapped founder to do? This is a new game, and a hard one to fight.
If someone is willing to sell at half price, knowing full well they’re taking a loss, you’re fighting a game with different rules. Call it the “milk in the back of the supermarket” strategy. It’s real.
Uber and Lyft showed us what balance sheet wars look like. Customers got cheap rides until the smoke cleared. Uber won, Lyft limped along, and every other rideshare vanished.
Did Uber have a great product? Yes. But what sealed the win was balance-sheet firepower. Cash to burn. Fares a bit higher now ;)
What do you do?
This isn’t whining—it’s just the new "battlefield".
What’s the Move?
So how do you compete? Do you join the fray, raise money, and fight dollar for dollar? Do you sell off 60% of your company to a banker just to keep swinging? Or do you double down on profitability and try to wait it out?
It’s not easy. You’ve built a team, product, and relationships. Rolexes and vacations aren’t enough to scratch the itch anymore. You’ve probably hedged your bets, tucked some money away. But the chips that matter? They’re still on the table.
That’s where the question gets spiritual. Is taking chips off the table right for your soul? Only you can answer that.
What I do know: balance sheet warfare requires next-level grit and commitment. It’s going to be hard—don’t fool yourself. I’ve been to the brink before, thinking I couldn’t handle more, and then more came. Somehow, I didn’t snap...yet.
Fighting Differently + Flipping the Script
Beachheads are eroding faster thanks to AI. Your years of a head start? That moat isn’t what it used to be. Feature gaps can now get closed in a few sprints. Many of these backed competitors aren’t just copying your features—they’re stitching them into a bigger suite, a walled garden (a supposed garden, mind you). What’s your narrative against that?
Price—let’s just assume you lose there for the sake of this conversation. Because it’s balance sheet warfare (said with a serious voice).
You must win on EXECUTION + UNDERSTANDING
Understanding the game—knowing your competition’s aim.
First—remember they are your competitor, not your enemy. They’re humans doing what humans do: looking out for their own self-interest. I’ve demonized the competition before, and I promise you it doesn’t make you a better leader or give you a better shot on goal. It makes you look like an idiot, shows your ego, and exposes your fragility. Trust me, I took this path. Dead end.
Next—Who Are You Playing Against?
If you’re competing against a public company, do a couple of things right away:
Buy 1–10 shares of their stock. You’ll now have access to voting rights and various calls you might not otherwise.
Analyze their last 8 earnings/quarterly calls to map their history and predict their future (all publicly available). Look at R&D spend, SG&A, profit vs. revenue growth, debt. The list goes on. Use these metrics to build your narrative
If you’re competing against a PE-backed player, dive into the latest deals that PE firm has done. Understand their “why.” Look for exits and disclosed numbers, especially those to public companies. Start to map their thesis, then forecast where they’re taking the game. You will need to fight with your tactics and on your terms but the market is the battle field.
The only way to get feed back on your theories is to act.
Execution
Maybe it’s reducing your tech debt, freeing 20–30% of your team’s time from maintaining old code, and reinvesting that capacity into white-glove onboarding or novel features.
Maybe it’s leveling up support or rethinking your internal stack so your culture doesn’t drown in manual work or clunky support software.
These moves won’t grab headlines. But they might keep you in the fight.
Plowing your current margin into lowering prices likely won’t move the dial when you’re up against mega-balance-sheet companies.
Go next level on your C-suite being with the customer—literally at their side learning, helping, and solving. The big companies hire minions to talk to the customer. That’s their chief Achilles’ heel, and it’s hubris. Which means it’s your attack vector.
Lastly - its iterating very quickly. We all know, bigger is slower (99% of the time) - be much much (much) faster.
No Easy Exit
Do you sell? I’ve been asked this three times in the last week by founders.
I don’t have a clean answer here. As I said above, I believe it’s equally spiritual as it is pragmatic. The only conviction I have is that the time is coming when founders will need to decide: double down or get out.
Paralysis won’t cut it. But let’s also not cheapen this into a “war.” Your competitors are humans—souls, families, real struggles. This isn’t zero-sum.
But it is a game. And you’d better know which one you’re playing—and play it with clarity, fast.
Selling isn't selling out. Selling is closing a chapter, and all chapters eventually come to a close.
Cheers to the doers!
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Are you a winner?
Or are you a loser?
We tend to think in binaries. I’m guilty of that.
Win = winner. Lose = loser. Simple, right?
But what makes you a real winner? Is it having more wins than losses? Total domination?
Are you a loser if you've lost 99 times and only won once?
Let’s test the logic.
Say I played a team of 5-year-olds in basketball. I'm going 100–0. Easy. I might even dominate the 8-year-olds. Still 100–0. Does that make me a winner?
Now put me up against anyone on a high school varsity squad. Suddenly, I’m 1–99.
Maybe I hang for a minute—before I blow my Achilles (again) trying to jump for a rebound with my 3-inch vertical and creaky back.
Does that now make me a loser?
If I’m a winner against 5-year-olds and a loser against 17-year-olds... what are we actually measuring?
This is where the binary breaks down.
In order to not be a loser, do you sit out? Not play the game because the risk of losing.
I have definitely done this. Hell, still do it.
I gotta reframe my brain.
Now I ask: What does losing really cost me? 99% of the time it’s nothing besides ego…but ego is a fragile god to play for.
Some side chatter amongst “winners” that you are this or that.
“Roy’s latest venture didn’t pan out.” Yep, they could say that.
But what game are you playing? Playing it for them or for you?
There’s an old saying in Vegas:
Play small, and even when you win… you still lose.
So yeah—play small. Protect your image. Keep your record clean.
But don’t confuse that for winning.
Because your pillow? That’s the final scoreboard. No crowd. No spin. Just you, alone with the truth.
Regret doesn’t care how “successful” your LinkedIn profile looks.
The safest way to lose is to never risk losing at all.
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