Hey Reader,

The founder is always the protagonist. It's the most epic, terrifying, and brutal part of starting a startup. Until you confuse protagonist with savior.

"We need to build everything in-house. It's the only way to ensure quality."

This founder's Series A startup had burned through $8M building their own infrastructure. They shut down last month.

That's not you, you don't have $8m and not building your own infra, but the underlying mistake. That's you.

It wasn't stupidity that killed them.
It wasn't lack of talent.
It wasn't even running out of money.

It was an anti-pattern - the strategic decision that felt completely logical, even wise, 100% justified in the moment.... but wasn't.

That’s what makes anti-patterns so dangerous.

They don’t feel like mistakes.
They feel like strategy.
They masquerade as wisdom.

This week's newsletter is different.

After reading a LinkedIn post on startup anti-patterns by Itamar Novick, Founder & GP of Recursive Ventures (an early-stage fund backing pre-seed and seed AI startups), I invited him to write this week’s newsletter.

With 100+ investments and hundreds of startup successes and failures, Itamar has documented 74 ways good decisions quietly kill great companies.

Anti-patterns are strategic missteps that feel smart. Until they aren’t.

HYPER RELATED:

Related: This is week two of silent killers. Death by a thousand cuts. Last week, entropy, the slow decay of systems, focus, and execution. This weeks anti-patterns is the brutal follow up.

I'm not in a downer phase. This is our protagonist era. :)

Startup anti-patterns in Itamar's words...

When founders ask me what makes startups succeed, I don’t have a great answer beyond “strong team, hustle, luck & timing.”

But failure? Failure follows a playbook. Statistically, most startups fail, and as a result there is actually much more data about startup failure.

For better or worse, it is only the startups that repeatedly don’t fail that have the chance to take advantage of luck and timing.

Anti-patterns are the silent killers. They’re not stupid mistakes. They’re not rookie errors. They’re strategic decisions that feel completely justified in the moment.

That’s what makes them lethal. They disguise themselves as the right move, never feeling like an anti-pattern when you’re in it.

• You’re not customizing, you’re “landing a whale”
• You’re not overbuilding, you’re being “thorough”
• You’re not losing focus, you’re “following the market”
• You’re not delaying launch, you’re “getting it right”

Then one day you wake up and realize what happened:

• That “strategic” enterprise deal? It owns your roadmap.
• Your “thorough” approach? You missed the market.
• Your “market responsive” strategy? You’re chasing competitors.
• Your “perfect” launch? It’s six months too late.

Small failures are part of the process. You stumble, adjust, learn, iterate, and just keep moving. Anti-patterns? They don’t teach you. They compound. It’s too late to recover.

Why are they so lethal? Because they compound.

• One custom integration becomes two.
  (Customize vs Configure)
• Two enterprise pilots become your whole roadmap.
  (The big customer won’t stop demanding features. You’re now their outsourced dev team.)
• Your “temporary” tech debt defines your product.
  (The quick fix so we can push to prod, is now part of core)
• Your “feature chasing” mindset becomes your culture.
  (Lack of absolute clarity and mixed objectives is the new new)

I’ve watched hundreds of startups rise and fall. Success stories are unrepeatable.

But failure often follows patterns. You think you’re making the right choice. Until you’re not.

They often fall into two distinct buckets. Strategic & Execution.

STRATEGIC KILLERS:

1. If You Build It, They Will Come ​
   You: “The product sells itself”
   Reality: No, it doesn’t. Ever.
2. Ivory Tower Syndrome
   You: “We know what users need”
   Reality: Your assumptions are close but rarely exact.
3. Competition Obsession
   You: “We need feature parity”
   Reality: You’re always one step behind, playing catch-up.
4. The Perfect Product Trap
   You: “We’ll launch when it’s ready”
   Reality: It’s never ready, and the market moved on.

EXECUTION TRAPS:

1. The Enterprise Trap
   You: “This whale will change everything”
   Reality: You’re now a consulting company pretending to be a startup.
2. The Infrastructure Trap
   You: “We need to control the full stack”
   Reality: Great tech, no users.
3. The Feature Factory
   You: “Just one more sprint”
   Reality: Your MVP is never minimal.
4. The Focus Fallacy
   You: “We can do it all”
   Reality: You’re doing nothing well.

I’ve documented 74 different anti-patterns that kill startups. Each one felt logical at the time. Each one had good reasons behind it. Each one slowly killed otherwise promising companies.

The startup graveyard is full of founders who made “smart” decisions.

Anti-patterns are not a death sentence. They’re a test. Spotting them before they become terminal?

Before any “strategic” decision, you align it to a framework of how you make big decisions:

• Speed vs Drag: Will this make us faster or just look busy?
• Real vs Imagined: Are we solving actual customer pain or our own fears?
• Impact vs Effort: Will anyone care about this in 12 months?
• Fight vs Flight: Are we building toward opportunity or running from fear?

Each question you skip is an anti-pattern waiting to happen.

Anti-patterns don’t kill you overnight. They kill you slowly. One logical decision at a time.

So many founders after their shutdown will tell you that “Looking back, every decision made sense.”

Your startup isn’t special. Neither was that Series A company that just died. They made logical decisions. They had good reasons. They were smart people.

But anti-patterns don’t care about your IQ. They don’t care about your funding. They don’t care about your vision.

They just slowly, silently kill otherwise promising startups.

As a founder, your job isn’t to know all the traps. It’s to try and recognize the signals. To see them coming. Not every anti-pattern is a mistake. Some are calculated bets, and that, is trying to know when to pull back and when to hold the line.

Thanks for reading, please follow me on LinkedIn for more.

Itamar

____________________

Thank you Itamar.

As always, if I can be of service, feel free to grab time.

LFG.

-- James

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