Heretics for Hire

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

Starbucks didn’t use to sell coffee.

At least, not in the way we’re used to.

When it was founded in 1971, it sold roasted beans and coffee-making gear. It was a retailer, not a cafe. You could get the coffee itself, and you could get whatever you needed to brew a cup of joe, but that was it. The “Cafe” in the sense of a place to buy a drink was mostly the domain of diners and dogwagons and small independent joints. When Howard Schultz arrived in 1982 as their Director of Marketing, he came at the problem of coffee from an almost heretical point of view; at least, according to how Starbucks did business.

On his return from a trade show in Milan, he came home obsessed with Italian espresso bars. He’d fallen in love with the ritual, the community, and the theatre of a barista pulling shots while aficionados sipped coffee in comfort - and he was convinced that Starbucks could replicate that model and that vibe and become America’s first chain of Italian-style coffee houses.

The founders - Jerry Baldwin, Zev Siegl and Gordon Bowker - wouldn’t have a bar of it. They didn’t want to be in the “restaurant” business, and they didn’t want to serve drinks. Frustrated and hemmed in, Schultz abandoned ship in 1985 and founded Il Giornale, his own chain of Italian-style coffee bars.

2 years later, Schultz bought Starbucks himself. It cost $3.8m, and nearly 40 years later, Starbucks is synonymous with coffee (even if the quality is entirely up for debate // absolutely s**t), with a market cap of $120.4 billion.

The Heretic won.

The way only Heretics can - by sustaining an unpopular belief long enough to establish an advantage while the market catches up.

We could use a few more of ‘em lately.

The tech world is stuck in the same growth playbooks, frameworks, marketing channels, accepted wisdoms, operating advice, and faux-disruptive hacks, and it’s become pattern-matched all to hell. Even businesses who insist they’re on the cutting edge follow each other in an ouroboros of tired and tested ideas, cycling from acquisitions to layoffs to product announcements to press releases to doom-laden forecasts about the inevitability of AGI and the forthcoming jobs apocalypse. Read any tech press, and it’s hard not to feel like we’re stuck in a Groundhog Day remake, even as we’re processing arguably the most significant paradigm shift in the history of the world.

AI has become...well, almost boring.

We’ve reached consensus.

You can’t honestly argue that OpenAI, Google, Meta, and Anthropic are functionally different beasts; they’re almost interchangeable in their thinking and their applications. Some fall behind, others pull ahead, but when everyone has access to the same talent, the same tactics, and the same thinking, processed and whitewashed through the same decks and town halls and pivots and meaningless North Stars, every company becomes almost interchangeable. Most of the founders and CEOs are attempting to appease, placate, or arouse investors, and they’re pulling out the same box of toys to do it.

We talk about moats as if they’ve become elusive and rare, or have been made obsolete; but to my way of thinking, the moat is as clear as it ever was. It’s conviction and heresy in the face of orthodoxy, and it’s within reach for anyone who has the courage to express it or elevate it.

It’s there for the taking, for anyone who can ask: what does everyone else assume must be done, and what are they wrong about? What assumptions no longer serve the customer? What do we actually believe that nobody else believes? And what are we prepared to lose in order to act on it?

The Heretic has 4 principles. They start with a specific insight - about the customer, the product, the market, the work itself. They are prepared to absorb an actual cost, no matter how high; giving up on customers, revenue, features, approval, even acceptance. They can produce observable evidence, in signals that can be read and tested, independently and clearly; a Heretic without evidence is a crank; but a Heretic with a working model can build a movement. Finally - they stay revisable, willing to fight tooth and nail for their underlying heresy, but ready to learn from reality enough to remain unkillable.

If you want a personal advantage, it’s this: become a Heretic for Hire. Instead of selling yourself on a particular set of skills, sell yourself on a set of beliefs, no matter how unacceptable, unconventional, or unwise the rest of the Faithful in your industry believe them to be. Sell yourself on your willingness to shout about the Zig when everyone else Zags. Sell yourself on your ability to absorb discomfort and make the world uncomfortable in return.

The question worth asking is this: do you have a single belief - more than a marketing slogan, more than a bullshit positioning statement - that you’re prepared to stand by, come hell or high water, that you’d be willing to keep on holding when the rest of the room rejects it?

And - to go a little deeper - if you have no such belief, what the hell are you doing with your life?