Jake Gallagher

@doomerzoomer Solid upside

@eladgil Even more disturbing is that many professors are actively encouraging struggling students to apply for learning disabilities privileges so they get extra time for exams.

What can possible explain this? We will never know

@kwharrison13 Was the VC already invested in Competitor A? If so, the responsibility also falls on the founder to vet that during their own due diligence process. There will always be cheaters in the prisoner's dilemma of life, especially in the VC/startup space.

VCs are so unbelievably stupid. They think founders are pouring life force into building a company from nothing all for the benefit of the VCs personal process and network? Here's the story of a VC using customer references from a founder to then intro to a competitor: - VC expresses interest in a founder's company - Founder meets the VC to share the story - VC asks for introductions to the founder's customers to do "diligence" - Founder obliges - VC spends the whole call asking what the customer thinks of Competitor A; barely spends any time on the company's product - VC continues to email those customers, even sending them customized demos from Competitor A (clearly custom made by Competitor A for that specific customer) - VC is barely responsive to the founder, now clearly just farming the customer references for leads to send to Competitor A As VCs make themselves the main characters, they forget this, but we are a service industry. Without founders, we're out of the job. They are gracing you with their willingness to have a conversation about this entity they're breathing life into. They are NOT your personal GLG sourcing engine. Do your homework on your own time and dime, or get f*cked.

The team onboarding seems like an easy no-brainer for the CS team. More vendors should offer a data migration upsell. Even if they don’t want to allocate dev resources to the project, they could partner with a trusted dev agency to handle data migrations. I mainly see contract buyouts at large deal sizes. It gets trickier for smaller deals, especially if the vendor is competing on price.

There are so many products I would buy if the vendor just said "I'll do all the work for you" Instead, they all just want to tell me why they are 10x better But not really help me: - buy out my contract - migrate my data - onboard my team

@RichLightShed @sarthakgh At under 50%, they are clearly not a monopoly. Here’s a list of problems that the government should allocate resources towards before blocking this merger: drug/child/sex trafficking, personal financial literacy in k-12, potholes, balancing a congressional budget etc

Disney (bought Fox) represents more TV time spent (10%) than Netflix does today (8%) and is still larger even with HBO added (8% + 1.3%) ps Lina Khan was the worst thing to ever happen to the United States

@ColinGardiner I think teams need to consider whether higher growth outweighs higher churn. Higher churn can accelerate the feedback loop to determine if they’re targeting the wrong ICP or need a better product.

Yes but churn tends to be higher.

Flight attendant comes over intercom: “your flight is oversold, I need two volunteers to take a flight this afternoon for a $300 voucher.” I spring into action. I was born for these moments. This is why I studied game theory. Literal tingles. I pull out my megaphone and address our boarding gate: “guys, they absolutely must off board at least two passengers or this bird isn’t taking off. Every 3 minutes they will increase their bid by $200. If we all hold out for 45 more minutes, 2 of us can make nearly 5 grand each. Textbook prisoners dilemma, this is (3,3) in its most visceral representation. I’m not even going to give up my ticket but I know value when I see value. Let’s make Nash proud ladies and gentlemen. Do not acquiesce. Do not defect.” Anyhow 2 people immediately accepted $500 and I called them retards on my megaphone and was placed in a detention room by airport police. This is why we study game theory.

@dunkhippo33 You should just tell them to add AI to their name. That seems to add $500M in value overnight

While we have portfolio companies that have gotten to unicorn status in 5-10 years. It's much more realistic (and common) - even on a fast trajectory - to take 10-20 years to get there.

@alex Sounds like there are about to be Limitless Meta Ray Bans

a16z led the Seed, marc is on meta board, seems like a politely soft landing?

@Hadley So you are saying that it is now a good time to be looking at the 95%?

Other than the post-correction days of 2022, this is the hardest environment I have ever seen for raising post-seed rounds. The top 5 percent get the headlines, but for everyone else it is a really tough environment.

@rohitdotmittal It's hard to get the data for the private companies, but I think doing an analysis on Price/Gross Profit vs Price/Sales would improve the comparisons. Most of these AI companies have significantly lower gross margins than that of their standard SaaS competitors

vertical AI startups are trading at insane multiples right now i dug into the numbers - ARR, valuations, and the math on whether these deals make sense here's what i found high level multiples: (caveat is that revenues are growing rapidly, so the multiples may already be lower) - Cursor: $1B ARR → $29B valuation (29x) - Sierra: $100M ARR → $10B valuation (100x) - Harvey: $100M ARR → $8B valuation (80x) - raised $160M today - Glean: $100M ARR → $7.2B valuation (72x) - Abridge: $100M ARR → $5.3B valuation (53x) For comparison, public vertical SaaS: Veeva: $2.45B rev → $35B (14x) Toast: $1.5B rev → $12.5B (8x) Procore: $780M rev → $11.2B (14x) ServiceTitan: $772M rev → $7.5B IPO (10x) 55x (for fast growth AI in private) vs 12x (lower growth public markets) the gap is 4-5x at 50x entry on $100M ARR with 100% annual growth: year 1: $200M year 3: $800M year 5: $3.2B exit at 10x (public comp) = $32B entry cost = $5B MOIC = 6.4x IRR = ~45% if the growth doesn't stay at 100% realistic scenario: year 1: 100% growth year 3: 50% growth year 5: 30% growth adjusted year 5 ARR: ~$1B (not $3.2B) new exit at 10x = $10B MOIC = 2x IRR = ~15% still works. but not venture-style returns. the magic number for 25%+ IRR with 5yr hold: need 3x MOIC minimum which means: 50x entry → need 15x+ exit with 80% CAGR 30x entry → need 10x exit with 60% CAGR multiple compression could be the killer by vertical: Healthcare AI (Abridge, Ambience): 40-55x quite rational - clear ROI, replacing $15B/yr in scribe costs Legal AI (Harvey, EvenUp): 50-80x fast adoption but crowded Coding (Cursor): 30x fastest growth - most reasonably priced in a way - but competition from the big AI labs is a risk valuations are pricing "winner take most" dynamics but theres 5+ well-funded players per vertical all assuming they'll be the winner AI vertical SaaS is real - the revenue growth is unprecedented but paying 50-100x ARR requires: sustained 60%+ growth for 5+ years no multiple compression being the category winner

@skylarromines So true

Some of my favorite people are surface level assholes but have deeply kind souls when you get to know them. Some of my least favorite people are sugary sweet nice but totally inauthentic when you get to know them.

@christophersaum Agreed. It's also presents a serious fiduciary risk if you are managing other people's money. You should invest because you believe their vision and hold conviction in their ability to execute. Vibing outside of that is just a cherry on top 🍰

There are cheaper ways to make friends than writing six-figure checks! :) In all seriousness, this dynamic is real. One caution: “I only invest in people I want to be friends with” is a limiting filter that biases you away from exceptional, different, or spiky founders. Some of the best founders I’ve backed are people I deeply respect, even if we’d never have been super close friends.

@mattturck Is it the claims line? If so, its probably going to be more than 17 minutes

Them: "AI is a bubble and customer service is a solved problem with too many startups" Geico: "there are currently 338 callers ahead of you and the estimated wait time is 17 minutes" (literally - otp right now)

@collision Congrats on the first "season"! Would love to see an episode about the future of AI with @elonmusk and @sama

That's a wrap on our first year of Cheeky Pint! We'll be back early next year with more guests in the pub. Please give me your suggestions! Guests, format, feedback, or anything else.

@thisisgrantlee You can't build a skyscraper on poor foundation. Just look at 432 Park Ave

The first 10 hires determine the next 100. The first 100 hires determine the next 10,000. Companies grow a lot like how cells replicate. Initial DNA spreads across the whole system. Brian Chesky took 6 months to hire his first engineer: "Every potential hire is guilty until proven innocent.” Chesky personally interviewed the first 300 employees of his company. He doesn't just assume everyone is a good fit. Most people aren't. Candidates must prove that they are. To find true missionaries, he asks, “If you had a year left to live, would you still take this job?" He is not looking for mercenaries who do it just for the paycheck. Paul Graham once wrote that “Airbnb is probably the worst idea that ever worked.” Early on, he noted that if the Airbnb guys could make and sell $4 cereal boxes for $40 to keep the company afloat, they could get people to rent rooms to strangers. That founder-level madness/energy/resilience/resourcefulness is to be replicated in the first 10 hires. They become the source code. Alfred Lin from Zappos said it differently: Culture = Core values + Actions × Every team member × Every day It's paradoxical, but taking forever on your first 10 hires is the fastest way to get company growth on a fast track. Creating the growth engine is meant to be a time-consuming process. Doing it well is all that matters. The founder essentially wants to replicate themselves. With the company set to motion in the right direction, initial hires will take care of company decisions the way the founder would. Airbnb sells travel and in 2020 the world made travel impossible. It was an existential crisis. Yet in 2021, Airbnb's market cap surpassed $100B. What kept them sailing was the DNA instilled by the “$40 cereal box” level creativity and scrappiness.

@edels0n Considering most of his "tax the rich" platform was shutdown pretty quickly, this is not entirely surprising.

As we predicted: Luxury home sales in Manhattan up 25% since Mamdani win. Realtor: “The idea that people would flee New York was overblown.” fortune.com/2025/12/04/mam…

@NikMilanovic Who says they aren’t innovators

what... just now? in 2025?

@pitdesi Haters love to root against the Pauls, but I think their reach will source some solid port co’s

Logan Paul, Jake Paul, Geoffrey Woo are starting an 8 week accelerator $25K SAFE followed by $100K priced round for a total 7% equity

@litcapital “There is no way AI can replace me”

How every investment banking analyst who worked on the Netflix / Warner Bros deal feels this morning (they mainly spread comps and sent calendar invites)