roykeely

Building B2B software for doers and domain experts. Fighting entropy while drinking too much coffee.

[roykeely @roykeely]

A $100M funding round sounds exciting!

But for CPA firms buying software, it should also raise a question: what future did this vendor just promise its investors?

Capital can help vendors move faster, build more, and support customers better. But it also creates pressure—and that pressure eventually shows up somewhere.

I wrote about why capital is a feature CPA firms can’t afford to ignore.

#accounting #investing #vc #taxtwitter

[roykeely @roykeely]

https://t.co/5C5arjJ2Sd

[roykeely @roykeely]

https://t.co/5C5arjJ2Sd

[roykeely @roykeely]

few quick hits
-The medium is the message.
-This is also what led humans to creating golden calves and the tower of babel.
-Words/letters are images technically
-Staged learning is likely better for the soul, so 'hit harder' ....sure through one lens, however Lindy the visual has a short half life except in very rase cases
-Books/written word will outlive any image/video in the sense that people will come back to it

[roykeely @roykeely]

@jasononfirms Surprised that page isn't trying to sell you a loan, payroll, get paid quicker, 401k, bookkeeping, email marketing or 7 other things

[Aaron Levie @levie]

This is counterintuitive for some, which is why there’s a paradox named after it. But if you lower the cost of something that was previously supply constrained, demand for that thing goes up. Software engineering is just one of the easiest examples to contemplate.

The process goes like this: every small business, every IT team, every large enterprise sees that engineering can now drive vastly more output. They then start to consider all the new things they can build or automate. They even test building prototypes themselves.

They only get so far with that approach because they realize there are still 50 other tasks that go into building software and maintaining it. So they start to hire more engineers to do that work. All of this for work they never would have considered automating or having software for if AI didn’t exist.

So yes, automating tasks, in plenty of fields, will lead to demand for experts, not less.

[roykeely @roykeely]

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.

[roykeely @roykeely]

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.

[roykeely @roykeely]

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.

[david friedberg @friedberg]

why not just raise income tax rates?

because your real intent is not to just “provide healthcare”.

you’re masking that you are proposing the creation of, for the first time in the 250 years of this American republic, an organized government seizure of private property from citizens.

you’re calling it a “wealth tax” or a “billionaires tax” or “millionaires tax” or whatever nom du jour polls well. but at the end of the day, it’s the seizure of private property from citizens by the government. citizens that earned money, paid their fair taxes on those earnings (53% if they live in California) and are now being told they need to hand over after-tax assets because the government has failed to provide promised services with the revenue it’s collected, and are now re-casting their own failure to be a socio-economic inequity that must be justly resolved... a slippery slope that has never gone anywhere good (see economic effects in USSR, Cuba, Venezuela, France and Norway wealth tax etc.)

the American founders fled tyranny in Europe and this amazing nation was populated by immigrants (myself and your parents) from around the world not just looking for a “better life” but for a place where they could have freedom from tyrannical governments that can take what they want from private citizens. a great nation borne of property rights, the rule of law, and endowed freedoms to believe, speak, or act. these principles led to the greatest run of innovations, successes, and widespread increase in prosperity, for all citizens, ever seen.

the citizens, the individuals, not the institutions, delivered this progress. those who invented, who toiled, who bled, who sacrificed, who took risk and persevered, who led, and who changed the world, are not charlatans, kleptocrats, or oligarchs. they’re what made us all better off. prosperity is a measure of america’s success, not its failure.

it is your principle that is so offensive, as evidenced by the broad disdain for your flippant flirtation with the darkest of human fantasy - socialism. you and other neo-socialists have led so many of us to reflect on America’s history and what it is becoming. that now leads so many to consider, so unnecessarily, leaving their homes for a place where everyone stands up to shout down the principle you suggest. because if your ideas are now considered moderate, it’s clear this titanic is sinking.

that a “simple tax” of taking assets that have been earned, through toil and tribulation, rightly taxed, and preserved, should now be unjustly seized, is your solution to a problem of obvious government mismanagement and outright fraud, tells us that your true motivation lies not in giving people healthcare but in cutting down success and deleting the system of prosperity and opportunity for all.

i don’t care, and neither should anyone else, what the sum total market value of a private citizens private assets might be. it is none of my business and should be none of yours. because, again, once you open that pandora’s box, we might as well study Lord of the Flies … there is literally nothing stopping 51% of citizens demanding that their government go out and seize 100% of the private property of the 49%.

want to give healthcare to people in need? do your job and fix healthcare. make it affordable. want to be lazy about it? then do your job lazily and raise income taxes.

want to take private property from private citizens who have paid their fair share of taxes and legally earned their property, then honestly declare that it is envy, not inequity, that you strive to resolve…

[roykeely @roykeely]

War & Peace BBC series a must watch. Slow TV and epic story.

[roykeely @roykeely]

Essay: https://t.co/pIJOTNbCUT

[roykeely @roykeely]

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!

[roykeely @roykeely]

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.
🔗 https://t.co/ty7WV6BIgd

[roykeely @roykeely]

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 ⬇️
https://t.co/s6zCFiJYUB

[roykeely @roykeely]

SPAM commercials during college football definitely a marketing zag

[roykeely @roykeely]

@ankurnagpal yes Please!

[roykeely @roykeely]

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!
---
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.

[roykeely @roykeely]

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.

[roykeely @roykeely]

Founder = Janitor

[roykeely @roykeely]

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