Customers rarely buy the benefit you lead with. They buy their way out of the moment they dread. For real estate agents, it's telling a seller their couch has to go.

Rough seeing someone make a carbon copy of your product a few months after meeting them. This is so much easier in the age of AI. Marketing and distribution have never been more important.

And here I thought crypto wouldn't come up while working with real estate agents.

My pitch to real estate agents was "hours of listing prep, done in minutes." Got a lot polite smiles. Then I asked how they tell a seller their couch is ugly, and suddenly everyone had a story. 15 years in marketing and I still had to relearn that "save time" isn't the pitch. Fewer carefully worded texts is. So we built @ListinoAI to say it for them. Politely.

AI is getting adopted outside of tech faster than people assume, but I'm not sure it's saving them time. Most real estate agents I've talked to use it for listing descriptions but still edit heavily. A better prompt would probably fix it, but few have the setup knowledge, so in the end I wonder if it nets out.

I spent a week with normies. My AI takes from the Texas REALTORS® conference: 1. AI has an all-or-nothing problem. People are stuck between “AI can do everything” and “AI makes mistakes so I can't use it.” The winners will figure out UX that guides what to delegate and what to review. 2. IRL is essential. When everyone can generate infinite content and outreach, actual relationships are hard to fake and more valuable. 3. AI as assistant > AI as replacement. Lots of convos about safety/errors/liability so positioning as offloading research, first drafts and grunt work avoids the fearmongering. 4. Old school marketing makes a comeback. Events, direct mail, local partnerships, maybe even door hangers. The noisier digital gets, the better offline channels look.

I love crypto. I just don’t want it to be my job anymore. For six years I've been denying that I founded a company. Now that there's a second one, I'm out of excuses. I started ProtestingPropertyTaxes .com back in 2020, using machine learning to support property tax experts before AI was a buzzword. Even though it's helped homeowners save millions of dollars, I filed it under "side project" and kept taking swings at other people's ambitious startups. When Berachain and the crypto market went sideways last year, I explored new roles but kept having the same feeling. In the middle of an AI gold rush, why am I downplaying my company and looking to build other people's ideas? The opportunity wasn't small as much as I had been keeping it small. At the same time, my cofounders were demo'ing what would become @ListinoAI, an AI listing assistant for real estate agents, and it felt more real than anything I was being pitched. So, bittersweetly, crypto is going back to what it's been for me since 2017. More in the hobby/social category than my daily work. I still hope to come party at a few conferences and will continue to do some advising, but it's time to stop hitching my wagon to other people's dreams when I have a couple of my own.

My career path in a nutshell: 1: Selling commemorative coins by mail 2: Employee #4 at a $1B healthcare startup 3: Baby VC for a billionaire 4: Performance at series B healthcare app 5: Growth at VC's in-house lab 6: Consulting for everyone I met at brunch 7: Italian adventure managing a blue chip art gallery 8: 1st non-dev at a personal finance app 9: Using influencers to sell gummy vitamins 10: Growth at a web3 car company 11: "Not marketing" a bear-themed L1 12: AI real estate tech founder (quietly started back around #8)

Does anyone still work in crypto or did liking everyone's layoff posts permanently train my algo?

Me: look how awful this apartment is My husband: looks like freedom

Claude talks too much. What's a good overarching prompt I should load in so I don't get 3 pages of explanation unless it's absolutely necessary?

We've entered the ai slop era of UX. Swear every time I log into an app, the interface has changed. Dear devs, just because you can redesign your app in 15 minutes with Claude doesn't mean you should.

I’m not on the team anymore, so no reason to say this other than I mean it. A lot of teams know how to show up when things are easy. Much fewer keep pushing when things get hard. Don’t mistake unserious branding for unserious people.

Found myself on the floor of @NYSE at a DJ set with old kiteboarding friends last night. crypto is still fun. Thank you @KiteVC @amandaterry @icme_xyz!

Worst part of crypto job hunting is that every interview has a 50/50 chance of being a scam.

Every guy wants a work wife. Nobody wants 5 paragraphs explaining why you should have come to the meeting and how it makes them feel that you didn't.

Tried Uptop’s new comp tool and it called me a “legitimate trad-to-crypto marketing operator with rare breadth and depth.” Turns out compliments from ai bots do feel good.