January 13, 2026 · 5 min read

business strategy

Ignoring the Infinite Canvas

Thank you Jeff T. and Justin D. for providing early feedback

It’s not the bad ideas that do you in — it’s the good ideas. If a thing is bad idea, it’s hard to overdo it. But where there is a good idea with a core of essential and important truth, you can’t ignore it. And, then, it’s so easy to overdo it. So the good ideas are a wonderful way to suffer terribly if you overdo them

Charlie Munger on Ben Graham and good ideas

EntryThingy looks simple on its face. We help artists find shows; we help galleries manage juries. But under the surface, the infinite canvas of possibilities feels paralyzing. We could build e-commerce capabilities, run gallery websites, or generate marketing collateral for sculptors.

Our resources are finite. We have chosen to be bootstrapped, so capacity constraints dictate our decisions. Choice burdens us.

§The Algorithm

How do you choose between Red and Blue when both would work? How do you stare at the abyss of potential and not fall in?

I use a loop. It is not original...Bezos has preached versions of it...but this framework keeps me sane:

  1. Experiment until you find what works.
  2. Double down on the idea.
  3. Kill the rest.
  4. Repeat steps 2–3 until it stops working.
  5. Return to step 1 when necessary.

Doubling down on what works is obviious. Less obvious is to keep doubling down long after you get bored.

§The Ceiling is Higher Than You Think

Most businesses are mediocre at a thousand things. The great ones take two or three factors and ride them to the extreme.

Costco identified two variables: limited SKUs and break-even pricing. They have been doubling down on those two variables for fifty years. Mediocre store aesthetics. Middling convenience. But they are rich because they ignored the rest of the canvas to paint one specific corner and perfect it.

At EntryThingy, one corner is notifications.

An artist signs up, applies to one show, and vanishes. We experimented to change this. Email beat every fancy new feature we tried.

So, instead of building a Shopify competitor (an "Infinite Canvas" if I ever heard of one), we are building a better notification engine. We are sending more emails. We are sending smarter emails. We are reminding artists about the contest they looked at three days ago but didn't finish.

We have only begun to explore email. We will keep swinging at this specific ball until we hit a ceiling. My bet is the ceiling is miles above us. The key here is we should keep doubling down as many times as we can. Success stems from an underlying truth about your users. Find that truth. Don't slow down just because you feel you’ve done enough. That is a fallacy.

In the oft-played game Battleship, if you get a "hit", you know to double down. Keep shooting around the hit marker until you sink the ship. The difference is, in Battleship, the sizes of the ships are pre-determined and rather small. The aircraft carrier stretches a mere five spaces.

In entreprenuership, size of a ship goes further than we could ever fathom. You can just keep shooting and shooting and shooting and it would take multiple lifetimes to sink your Battleship.

§Capacity Limitations

The hardest choice in business is balancing the urge to double down with the need to experiment. Google manages this with "twenty-percent time", a system that protects the capacity to find the next hit without distracting from the current one.

American Express illustrates the danger of getting this balance wrong. In the 1850s, Amex was a financial juggernaut. But they refused to follow the Gold Rush. While the "Wild West" exploded with potential, the Amex board doubled down on their "industrial east" corridor. They were too cautious to experiment with a new geography. Their founder headed west to start Wells Fargo.

By refusing to paint a new corner of the canvas, Amex handed a future empire to their competition. That caution was a trillion-dollar mistake.

Doubling down is the goal, but never spend one-hundred percent of your resources. Leave room to explore the edges. If you don't experiment, you might perfect one corner of the canvas while the rest of the world moves to a different sheet

§Intelligent Borrowing

Once you know what to double down on (for us, notifications), you still have to decide how to do it.

Borrow from those smarter than you.

We don't need to re-invent email. A/B testing on the best time to send the email is repeating work others have done. Somebody else, with a billion dollars and a thousand experiments already run, has already done this. If a competitor has an effective notification flow, study it. Ask: Does this fit my strategy? If yes, borrow it.

This buys me time to focus on the one thing I can't borrow: the specific value we create for our users. The canvas might be infinite, but we need to paint one corner to perfection.

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Myles Marino

Partner at Third South Capital, where we cultivate, build, and buy software.

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