🗃 Rig the game

How tech founders can consistently publish content without hating themselves for it

Tommy Clark
September 28, 2026

Hey!

Welcome to Social Files—your no-BS guide to generating demand for your B2B product using social & content.

Spent my weekend in hibernation after a long few weeks of Content Writer recruiting. We hired someone! And we are hiring some more writers (see open roles here).

I’ve been writing online consistently for the past seven years. I’ve hardly ever ‘skipped’ a day. And, being real, it’s not all that hard for me.

Today’s piece gets into what I believe to be the secret to my consistency. It all comes down to two simple questions.

Shall we?

🔎 DEEP DIVE

Rig the game.

How tech founders can consistently publish content without hating themselves for it

Every so often, I get this urge to try and ‘crack’ short-form video content. I have a handful of close friends who have built big audiences on Instagram. They make a good amount of money from it, too. And brand deal margins are a hell of a lot better than an agency’s.

There’s merit to it.

I would do well to have 100k followers on Instagram, whether it be to market Compound or my upcoming sci-fi debut. I’ve made some progress on the latter (15.9K isn’t horrible).

But whenever I commit to ‘going hard’ on short-form video, I run into a few problems:

(1) To ideate, script, and film a good short-form video takes…I don’t know…five hours? I’m not even counting editing; thank goodness I have an editor for that.

(2) The process in #1 does not energize me. I’d go so far as to say I hate it. There is a deep resentment in me toward short-form video at all. It is a plague, and we are worse off for it.

Writing, however, is energizing. Every morning, I subject myself to writing 1000 words of fiction before entering the crucible that is running a content agency; and you couldn’t pay me enough to stop.

(3) Instagram distribution is not the bottleneck in my business. I get most of Compound’s leads from LinkedIn, YouTube, this newsletter, and referrals.

Really, marketing isn’t the bottleneck at all. For Compound, recruiting is (we’re hiring).

I just mentioned it takes five hours or so for me to make a good IG Reel.

In that time I could:

Take ~10 interviews with potential Content Writer candidates.
Reach out to hundreds of potential candidates.
Scavenge my networks for leads.

All of which would have more impact on Compound in Q4 ‘26 than a green-screen Instagram reel with 100K views.

But look, there’s a point in me telling you this that I think will help you ‘crack’ your own approach to executive content.

When you're evaluating a content marketing initiative, ask yourself two questions:

Could I see myself doing this five years from now?
Is this the actual bottleneck?

And look, sometimes there will be a task that you hate that is the bottleneck in your business. We all know Elon’s quote about eating glass by now.

If your customers are indeed on LinkedIn (as they are for most companies in B2B tech), and you refuse to try to learn the game, you are doing yourself a disservice.

If short-form video ever does become the true bottleneck for Compound, I will set myself to solving it because, well, that’s what the founder does.

But even within the channel, there are options for how to approach it.

If you’re tired of generic founderslop, you could opt to publish high-signal research using your customer data. If you cringe at people in your category taking themselves too seriously, you could opt for meme marketing. If you're articulate on camera, maybe you do run up video.

You’ve got to do whatever you can to rig the game in your favor.

Sometimes this means delegating entirely. This won’t sit well with the content purists out there, but I have a client on the Compound roster who, for the past year, has just sent us occasional voice notes that turn into LinkedIn posts he hardly edits.

He’s booked dozens of demos with mid-market and enterprise companies.

There are countless ways to win, infinite winning combinations, and it is a fool’s errand to play in a way misaligned with your natural strengths.

(Reminder to self)

TOMMY’S BOOKSHELF 📚

Current read: The Power of Myth by Joseph Campbell and Bill Moyers. A little non-fiction action. Funny story about how I found this one: I saw it included in a stack of books Pierce Brown (the author of Red Rising) posted on his Instagram story.

I’ve had The Hero With a Thousand Faces on my shelf for some time, and after finishing The Power of Myth, I will for sure be picking it up. Great read.

On the fiction side: continuing my trek through The Ships of Merior. It’s great, but I am feeling the pull towards something a bit more fast-paced.

Evergreen reminder: if you haven’t yet, do yourself a favor and read Red Rising. This is the gateway drug to fiction reading as an adult.

If you want more book content, I’ve built a little audience on Instagram where I post about fiction and writing.

BEFORE YOU GO…

As always, thanks for allowing me into your email inbox every week.