☕️ Jack Raines-Maxxing

+ Tech Breakfast Clubs in NYC and SF

Author

Morgan Barrett
April 02, 2026

👋 Hi, Breakfast Club Members!

Today, I have a major treat for you - scroll down and get a glimpse into the mind of Jack Raines.

If you asked 100 people who know Jack to describe him, you’d get 100 different descriptions.

Jack Raines - the college football player?
Jack Raines - the only guy besides Chamath to make money on SPACs?
Jack Raines - The blogger?
Jack Raines - the Guinness influencer?
Jack Raines - the guy who matched with his boss on hinge?
Jack Raines - The guy who trolled LinkedIn so hard he got a book deal?
Jack Raines - The guy who got a job at Goldman Sachs by winning a business school beer mile race?
Jack Raines - the early stage investor at Slow?
….

It’s time someone did a little digging to make sure we’re all talking about the same person.

Resources:
-Clerky offers a $100 discount for TBC Members on their formation packet. Reply to the newsletter and I’ll send you an invite
-Fixing the YC SAFE: Reply to the newsletter and I’ll send you a redline for the YC Postmoney SAFE that can save founders millions in dilution

Tech Breakfast Club Events

SF Tech Breakfast Club (Tuesday, April 14th)
Co-hosted with Jack Rains (Slow VC)

NYC Tech Breakfast Club (Thursday, April 23rd)
Co-hosted with Kendra Schultz (Benchstrength)

SF Teach Breakfast Club for AI Leaders (Thursday, May 28th)
Co-hosted with Baseten

Tech Breakfast Club 🤝 Rho

Time to upgrade your business banking?

Jack Raines-Maxxing

Okay, 18 months in. It seems like you’re having a great time 
I’m having a blast. Nobody’s having more fun being alive than me—I stand by that.

So is that in spite of being a VC, or is that because you're a VC?
Sort of both, sort of neither. VC is just one ingredient in a bigger pie of… life satisfaction? Personal enjoyment? I like what I do for work and the team I work with.

That said, I do think that “VC” as a category can be a tough career path for young people. A lot of “investing” at some of the megafunds, for example, if you’re a junior investor, is more cold-calling and BDR work than it is “investing.” The measurable is inbound quotas, not quality of deals or establishment of relationships.

So I guess the main reason I like VC is that I like the firm I work for. Slow Ventures is awesome. Great team, great track record, just a really sharp crew of fun personalities. People ask me if they should go into VC (and, if we’re being honest, the reason most people go into VC when they’re young is because they like the idea of prestige + prolonged optionality. VC is a high-clout job), and my advice is that fund diligence is everything. If the people you work with are A+, and if they know how to make money, it’s probably a good opportunity. Otherwise? You’ll end up either working with assholes or joining a fund that might not be around long.

Why does Slow work? Why can they keep raising funds?
Culture, track record, and not losing “who we are.” Everyone at Slow is very much themselves, in a good way. There’s no LARPing, and what you see is what you get with us. I do think that, plus the fact that we’ve made some good bets over the years, has helped build and maintain LP relationships. Also, we’re a seed fund. We’ve always been a seed fund.

A lot of megafunds have moved downstream, or early-stage funds have tried moving more upstream. Or pivoted strategies from “crypto” to “AI infrastructure” or whatever. We have made some new bets over time, like with our Creator Fund, but we are still, at our core, generalist seed investors. Not chasing “the hot thing” is underrated.

What’s got you excited?
So, I’ve been geeking out on two things lately: what we call “second-order effects of AI” and weird prosumer plays. The really fun ones have some overlap.

One example is a company called Petty Lawsuit that makes it easier for people to take legal action—basically streamlining demand letter generation and small claims-type processes. Example: the demand letter I “sent” Sam Lessin. It sounds funny, but it addresses a real gap: most people can’t easily access the legal system.

There’s a long-tail of millions of people each year who have legitimate disputes that could get paid out, whether from party-to-party settlements or in court, but the headache of taking the steps needed to pursue those payouts creates a lot of friction. Maybe a customer invoice is 60 days late, or your landlord is falsely holding your security deposit, or you were wrongfully fired. Using AI to automate the entire “demand letter generation process,” and corresponding follow ups, has created a pretty interesting business.

Another is Memelord in the meme infrastructure space. The idea is that memes are actually the most condensed form of information transmitted person to person, and “winning the narrative” has never mattered more. Public market valuations, private market fundraises, and even elections are increasingly influenced by “vibes.” Yes, sure, fundamentals matter, but narrative amplifies fundamentals in both directions, so being able to “win” the memetic war is a competitive advantage.

Memelord is the best platform for the rapid creation and deployment of trending memes; they even have an API that your AI bots can use now. (see below for footage from my AI bot, Clank).

Is there a unifying thesis?
Yeah; what does AI “break,” and what new markets are either 1) made possible as a result or 2) does AI serve as an accelerant without “AI” being the product itself. Like, do we seriously need another data-labeling startup (RIP Mercor post-data leak) or a $700m seed round for a “world model”?

AI “breaks” the legal system by removing friction to litigation: we’re moving toward a more litigious society. What are the opportunities there? Social media sentiment no longer just “reflects” reality; it creates it (George Soros’ reflexivity remains undefeated). AI only accelerates the proliferation of narratives by reducing the cost of content creation; 

The most interesting opportunities are in what AI enables or disrupts indirectly. 

Why not invest directly in AI labs or core model companies?
It’s mostly a math problem.

Those companies require enormous amounts of capital. Even if they succeed, early investors get diluted heavily because the companies have to keep raising at massive scale. 

If you compare it to something like Facebook or even Uber, which was, at one point, considered a cash incinerator, early investors there had much cleaner ownership and outcomes. OpenAI seed investors will “make” money at IPO, but the return profile on what would be a trillion-dollar exit will be “good not great” by seed standards simply due to dilution. How many hundreds of billions can you raise?

These are great for megafunds and sovereign wealth allocators, not seed funds.

Humor is probably the safest area of humanity regarding AI but you’ve found a way to invest humor infrastructure with Meme Lord- 
AI is a force accelerator of an underlying thing – if your thing is good. If you’re funny, AI lets you be funny at scale. If you’re not funny, AI gives you slop and I hate you. The ironic thing about AI is that because it tries not to be offensive, its default humor is inherently limited (like, my AI bot, because it runs on Claude, sometimes blocks my meme creation prompts due to Anthropic’s settings). So I would say that “edgy” or “satirical” humor will be invincible. You can’t vibe code a Jerry Seinfeld when ChatGPT triple apologizes for any mention of the word “retard.”

What’s changing about your day to day life directly because of AI?
My attention span has shrunk to the level of a goldfish due to my twitter addiction and continual playing with Claude code. That’s kind of a joke. But I do think there’s a real “personal Jevon’s Paradox” that myself and a lot of people in the tech world are feeling. Like, “HOLY SHIT EVERYTHING IS MOVING SO FAST I NEED TO KEEP UP. MORE CLAUDE CODE. MORE READING UP ON NEW AI BREAKTHROUGHS. WHAT HAPPENED WITH THE RECENT CYBER HACKS?” It’s a bit stressful.

I’ve also tried to automate some of the more tedious parts of my job, like filing expenses. God, I hate filing expenses.

Slight pivot away from AI, but outside of Slow, I also just finished writing a book, Young Money, which was a grind. It’s like a less pretentious Defining Decade on navigating the opportunity cost of your 20s. I basically worked every weekend for six months. Man, writing a book sucks more than expected. Now I finally have my weekends back. 

The book comes out August 4, and I’m planning launch events in SF and New York and hopefully sell a million copies. I’d love to rent out a bar and have an open bar, but you have to buy a book to get in. So we’ll see. 

You’re on a hot streak last couple months on X -
I’ve been ripping bangers for five years now. I’m streaky, but the key is just taking shots. X humor is mostly about layering on top of existing trends. If something is already catching the zeitgeist, you add a twist. I think I'm in a flow state of seeing what things are popping off, and being able to feed off of that. My pinned tweet about the Chili’s in the Chicago airport is a good example.

What are you bullish on culturally?
I’m very pro retard-maxxing.

I think retard maxxing is actually two things: proof of humanity, where doing irrational shit to its fullest extent is empowering. It’s also the most “high agency” thing you can do; just fully committing to a bit past the point of no return.

What else are you maxxing right now? 
I think looksmaxxing is hilarious. I kind of like the idea that your political beliefs should be based on who’s the hotter candidate. As a vector, as a funhouse mirror of humanity, I appreciate it. I’m trying to do intermittent AI fasting, where I don’t use AI at all on weekends. 

I’m also New York maxxing. It’s good to be back – the best city in the world. I think the ideal setup is living in New York and having frequent San Francisco exposure. It’s kind of like if you sit out in the sun all day, you’re going to get skin cancer. But if you go out in the sun a bit, it’s very good for your health. Bi-coastal maxxing.

What else are you paying attention to?
I’m addicted to Twitter, so I’m monitoring the situation – and by that I mean everything. I’m oil crisis hazard avoidance-maxxing. I’m prep-maxxing. I’m not, however, peptide-maxxing. I’m free will-maxxing, actually. 

What about public markets?
Public markets and early-stage are the two most interesting forms of investing because you get paid for being right, not for consensus. In public markets specifically, I’m curious to see which victims of the SaaSpocalypse end up crushing it. Like, I’m not making any predictions, but it’s hilarious that Wix might quietly be an AI winner simply because it bought Base44 (Lovable comp) for like $80m.

ServiceNow is interesting if AI benefits incumbents. I think Bill McDermott is a goated CEO. Dude is crazy. 

Also, I appreciate the pullback in private credit. The whole space just feels snobbish.

Any fun conspiracy theories you like?
Population fraud: the world only has 2 billion people. That makes a lot of sense that countries exaggerate their population. Like, do you really think Nigeria and Indonesia have more than 500 million combined citizens? I don’t.

Oh, another one: the Dark Ages didn’t happen and the current year is actually 1872. We made up 150 years. Retardmaxxing.I don’t fully believe these theories—but I endorse them

About Morgan Barrett:
Morgan is the creator of Tech Breakfast Club. He hosts breakfast meetups in NYC, LA, SF (and occasionally Austin, Miami, Boston) that bring together the best founders and investors.

Morgan is also a Startup Lawyer at Optimal, an elite lean boutique startup law firm repping clients funded by a16z, Sequoia, Kleiner, Accel, and countless other VCs. He works with clients from formation to exit, in collaboration with Optimal’s partners.