It Won't Work If You're Not Obsessed

PS: I’ll be running some more events this fall and beyond. A mix of mastermind retreats and small-group dinners in SF, NYC, and more cities.

Drop a quick note here if I should reach out when we launch some (takes 30 seconds, literally).

🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Matt Higgins shared advice to first-time founders who are fundraising (Link)

• Jon Lai shares a fundraising masterclass from Travis Kalanick (Link)

Growth

• Finn Mallery shares the 1% of sales advice that actually matters (Link)

• Shridar A on what the first version of your product is supposed to do (Link)

• Peter Kazanjy on how to loop your pipeline every week by stage (Link)

ICYMI

• Describe the app you want and Emergent handles the building and deployment. (Link)*

• Andrew Duca shares a common trait the most successful founders have (Link)

• Mariya Valeva on how most founders hire for the person they used to be (Link)

• Matt Epstein on how people need to stop building self serve products (Link)

• Vadim Strizheus on the 3 things founders need to think about everyday (Link)

 Opportunity: Duolingo For Trades

Saw this from Logan Gott and haven't stopped thinking about it.

The trades (as in the careers you’d go to a trade school for) are one of the last corners of the economy nobody's building real consumer software for, and the labor shortage there isn't slowing down.

I invested in an awesome company called Flashpass that’s building the software to power the schools themselves, and imagine there’s an opportunity for someone to build a consumer-first version for folks who aren’t able to make it into the trade schools themselves (due to location, cost, etc).

Gamified, bite-sized skill building for welders, electricians, HVAC techs, and more.

I could see it.

🧠 Framework: Design Thinking Process

It’s tempting to jump straight to building (these days more than ever) but you can still move very fast and invest just a little time in your thinking upfront.

Here’s a five-step framework (from CapCut, surprisingly) to consider:

1. Empathize → Talk to actual users. Watch how they behave, not just what they say they want.

2. Define → Turn what you learned into one precise problem statement. A vague problem gets you a vague product.

3. Ideate → Brainstorm solutions without filtering yourself. Judgment comes later, not here.

4. Prototype → Build the cheapest, fastest version of the idea that lets you test it.

5. Test → Put it in front of real users again and let their reaction, not your opinion, decide what happens next.

What I see is that a majority of products didn't fail at Prototype or Test, they actually failed way sooner. Back at Define, most of the time, because nobody forced themselves to nail down the actual problem before building the solution.

📈 Trend: Companies Spending More On AI Are Hiring More

Here’s a counter-intuitive datapoint:

The companies spending the most on AI aren't the ones cutting the most headcount. It’s actually the opposite. They're hiring the most. They’re the ones with the balance sheets to actually operationalize LLMs.

The pattern holds across the board.

Meanwhile the layoff headlines (Atlassian, Block) are mostly companies playing catch up, cutting cost centers to fund experiments rather than reinvesting productivity gains into growth.

Worth remembering next time someone tells you AI just means fewer jobs.

💬 Quote: It Won’t Work If You’re Not Obsessed

Obsession isn't something you develop after you pick a problem to work on, or a direction for your startup.

It isn’t really something you “develop” at all.

If you have to work yourself to care, you’ll never be as obsessed as someone who inherently gravitates towards that same thing.

I've watched founders grind for years on businesses they were never actually obsessed with but rather were just… committed… to.

The problem is that commitment without obsession looks identical from the outside for about 18 months. Then it doesn't.

The replies to Darren’s tweet that are calling this out by saying things like "I got too obsessed and it still didn't work" are missing the point.

Burnout is just obsession without a filter for what actually moves the business.

Obsessed founders waste less time because they can't stand doing anything that doesn't matter.

So if you're asking whether you're obsessed enough with your startup, you're not.