You Have To Be Delusional

And how about a founder retreat?

Jul 15, 2025

Hey y’all — who’s up for a founder mastermind in Cape Town, or Medellín?

Tyler Denk, the co-founder of beehiiv, and I are considering hosting one together for a week around NYE as a way to kickoff the year completely refreshed.

It’ll have top tier founders, an epic villa, private chefs, in-house massages, and a good mix of serendipitous downtime and planned activities to grow as founders.

He’s run a few of these and I’ve run over 40 (but this would be the first in a few years).

LMK here if you could be down.

And here’s today at a glance:

Opportunity → AI Music
Framework → AARRR Metrics 🏴‍☠️
Tool → Portless
Trend → AI Consulting
Quote → You Have To Be Delusional

PS — Become a member to get access to my founder membership including an engaged community, fundraising support, fireside chats and more.

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

Hubert Thiebot on what makes a great fundraising memo (Link)
Francis Santora on the common reasons he passed on over 4,000 deals (Link)

Growth

Eliana on the hard truth that no one tells you about launching (Link)
Hesham Zreik on the obvious thing startups are overlooking (Link)
Michael Sikand on key differences building a media now vs. 5 years ago (Link)

ICYMI

Elite remote assistants from $13/hr, trusted by fast-moving founders, investors, and operators (Link)*
Greg Isenberg’s most important lesson learned building startups (Link)
Eldar Sadikov’s advice on how to pick a co-founder (Link)
Zain Jaffer on learnings from failed startups (Link)
Ben Lang shares YC’s how to spend your 20s in the AI era (Link)

💡 Opportunity: AI Music

For the past few weeks, I’ve been obsessed with this band.

Here’s a track of theirs I’ve probably listened to 50+ times since mid June:

The Wind Still Knows Our Name

The Velvet Sundown · Floating on Echoes · Song · 2025

open.spotify.com/track/6z9miYNhMhFgqsWMImaVOn?si=3b93afb4def945a9

Their tunes are somehow both very consistent in vibe and also unique in mood. And they have little flourishes with the vocals, drums, or guitar that are unmistakably a sign of mastery.

The twist: their instrumentation, lyrics, vocals, and images are all 100% entirely AI generated.

After the mainstream press caught wind, they’ve accumulated well over 1 million listeners on Spotify and have attracted their share of purist / envious haters as they’ve put out 3 albums in a month.

No one knows who’s behind it (is it one guy in his basement? A record label? Or Spotify itself?), and we can argue whether that even matters.

What definitely matters is that the amount of people who can make commercially successful music now includes millions more people.

AI is just the new guitar. And it’s a lot easier to learn.

There are tons of ways to build businesses in this niche:

Manage 10 “bands” yourself
Start a label that works exclusively with AI "bands” and advocates on their behalf to labels, partners, etc.
Create an AI-only music discovery platform (the Spotify of the future?)
Create a tool that lets users have Radiohead cover The Weeknd and distribute that to platforms (with the artists getting paid)

There are a ton more ideas here.

IMO it’s very early days for an area that will become big. A lot will need to be rebuilt to be AI-first.

If you ever wanted to get into the music business, now is the time.

🧠 Framework: AARRR Metrics 🏴‍☠️

I will spare you the pirate puns, but the AARRR framework is a good and simple way to evaluate whether your startup is something people want or not.

Founders often overcomplicate this, but honest answers to these five questions (without caveats) will paint a clear picture.

If you’re finding you have to do a lot of explaining to answer these, something is wrong. PMF occurs when the answers to all of these are so obvious they probably take no more than a sentence to answer in full.

🛠 Tool: Portless

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Restock best-sellers in 3-5 days
Sell days after manufacturing
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Turn 6-week delays into 6-day deliveries straight from China.

Take control of your summer season — start with Portless today!*

📈 Trend: AI Consulting

In 2023, after it was clear that ChatGPT had changed everything, I remember seeing someone say that McKinsey was going to make more money on AI than OpenAI.

In the longrun, I’m not sure. OpenAI has a chance to be a trillion dollar company.

But in the near term, it’s possibly true.

AI consulting is exploding, as you’d expect.

What you (might?) not expect is that it’s not just the big guys raking it in.

They are, sure, but there’s also a ton of new micro-consultancies that have spun up in various verticals, typically around workflow automation with tools like Plumb, Lindy, n8n, etc.

This is probably the best area to be in if your primary goal is to make $1 million by the end of the year, starting today.

💬 Quote: You Have To Be Delusional

I just moved to a new city and, for the first time in over 10 years, I’m likely about to have a primary residence somewhere other than SF, NYC, or LA.

In those places (especially SF), you’re encouraged to think delusionally.

I mean that in a good way.

You have to be delusional to be a founder.

And, in SF, that’s basically understood. I would even say it’s expected, and it’s somewhat socially weird if you don’t.

But what I noticed this year as I toured around much of the rest of the country looking for this new home base, is that elsewhere the opposite really is true.

Early stage investors are looking for 2-4x returns. Maybe 10x at best. They want to build and flip.

In SF, it needs to be a 1,000x+ potential moonshot to get VCs interested.

The aspect of Silicon Valley culture is precious and, as I talked about when covering Silicon Valley’s history, should be exported (no matter what you think of SF as a whole).

Like Greg says below, if you want to change the world, or maybe even if you just want to convince your friends and family that leaving your job to start something new is a good idea, you have to accept being seen as delusional.

It’s par for the course.