No name tags, no networking hours

In today’s issue: Founder-market fit, lost wallets, and how to raise from angels

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With Marty & Will, founders of Agree.com

Notes from a messy desk

People sometimes ask how I support the startups Trust Fund invests in when I’m not based in the same city (or even country) as they are.

Here’s the thing: none of them are in Los Angeles.

The reality is, with distributed teams and the ability to work from anywhere (not to mention travel), I can bring founders together in my own time zone – or any other, really.

A couple of weeks ago in Mallorca, I hosted seven founders for an unstructured, week-long residency. No panels. No name tags. No “networking hours.” Just co-working, cooking together, swimming, trading ideas, and actually getting things done.

Most investor events are so programmed that if you try to work, it feels like you’re skipping class. This was the opposite: founders could keep up with their companies while building real relationships with each other (and me!).

Already planning the next one. Where shall co-work next?

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🫖 Tea with GPT — This Week’s Uses

Next to Chat GPT, Howie is now the AI tool I use more than anything else. Howie is the ultimate secretary – all I have to do is loop his email address into an email thread and he’ll go back and forth like a human to schedule something with a real person. He can also do things like inform meeting attendees you’re running late (guilty) and reschedule events.

He recently handled scheduling with a new business contact and when I said “isn’t Howie great? He’s an AI” he was so shocked he signed up as a paying user immediately. No impersonal calendar links, just give Howie your scheduling parameters and it’s handled. If you want to skip the waitlist and get 50% off your first month of Howie, fill out this form.

Duckbill is a human-assisted AI that’s been picking up my admin slack both with personal stuff, work stuff, and new landlord stuff. In the past month, Duckbill has scheduled a dentist appointment, plumber, and get this: a few weeks ago I took a ferry from Menorca to Mallorca, left my passport and wallet locked in the hotel room safe, and DuckBill coordinated a UPS pickup, payment, and coordination with the hotel to have it delivered to me before leaving Spain (at a rural Airbnb with no address, no less). Use my link to get 50% off your first 2 months.

I’ve been tinkering in Lovable, which pretty much lets anyone build anything without any technical knowledge. Spun up a job board that pulls in jobs from Trust Fund’s portfolio company career pages. Pretty cool.

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AI Tip of the Week

You know how we're always drowning in our own digital mess? Like, I'll spend 20 minutes hunting for one email and then forget why I needed it.

Well, Claude Desktop just solved that whole situation. You connect it to everything (iMessage, Gmail, calendar, Google Drive) and then you can actually have conversations about your own life. Not just searching, but like, real back-and-forth.

I'll ask it "What did my lawyer say about that contract?" or "Do I have anything important tomorrow?" and it pulls everything together. But here's the really smart part: it also remembers our past conversations. So I say "Remember when we talked about that marketing strategy last week? Pull up those emails we discussed" and it actually knows what I'm referring to.

It's basically like having an assistant who pays attention to everything and never forgets context. You can ask "Based on my week and what we've been working on, what should I focus on?" and it connects all the dots.

Having something that manages my mess and builds on our previous conversations? That's the kind of efficiency that actually moves the needle.

Get more news and AI tips like this over at my friend Audrey’s newsletter, The Distillery.

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Links to make you smarter and more interesting

Heard of product-market fit? Welcome to founder-market fit. Trust Fund startup Nectar Social founders (and sisters) Misbah and Farah Uraizee joined Inc. Magazine Editor in Chief Jason Feifer on his podcast and shared the importance of founder–market fit: solving the problem only you are built to solve. That clarity won them early customers, a fully subscribed seed round without a single pitch deck, and the confidence to drop a game-changing product into the market. With customers like Olipop, Tower28, and Jones Road Beauty, they know what they’re talking about. Oh, and Vogue Business just named them one of 9 fashion tech startups to watch in 2025.

And if you’re looking to bring in funding, check out this field guide from the founder of Akita, sharing her learnings on how angels think and what actually gets them to commit. It’s the kind of insight you want before you start filling your calendar with pitch coffees.

A TikTok goof just gave Sweet Loren’s a whole new name. The lesson? You can’t control how your brand travels online, but you can ride the wave if it works in your favor. Meanwhile, sellers are losing out big time after Amazon’s sudden breakup with Google Shopping ads.

Upwork’s “mindful AI” is the latest proof that productivity tools are now selling themselves on emotional regulation as much as efficiency. And while AI tools keep stacking, GPT-5’s chaotic rollout (and users mourning the old models) is your reminder to never bet your business on a single API behaving as expected.

The “youth market” you’ve been courting? Gen Z is almost 30. They’ve aged into mortgages, pets, and joint pain, so maybe stop talking to them like they’re cramming for finals.

On the content side, brands are rethinking influencer spend — stuck between search and social — while others are betting big on creator-generated content as the new paid media.

Even beauty brands are ditching Instagram for Substack, owning their customer conversation instead of renting it from an algorithm.

In design land, UX trends for 2025 show we’re deep in the “everything looks the same” era — and yet two brands are still in a 40-year logo war. File under: the long tail of brand equity.

Three “save-this” reads for your go-to-market brain:

1. How to nail your ideal customer profile so you’re not wasting time on the wrong leads,

2. Why “outcomes over output” should be your filter for every product decision

3. A surprisingly human guide to deep research for GTM.

And because the internet can’t help itself: Reddit just blocked the Wayback Machine. Which means all your cringey 2014 shower-thought posts are safe… for now.

Last but not least — a founder comeback worth studying. Ty Haney’s second act with Outdoor Voices isn’t just about relaunching a brand; it’s about controlling the narrative before someone else does. Founders, take notes: this is how you turn a past headline into your next launchpad.

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