serial founder (ai newco in stealth) // gtm advisor // writing soft thinking on ai-native growth for the real economy
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Joined August 2010
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calanthia retweeted
Wow: Stripe and Advent have bid more than $53 billion to take PayPal private. 🤯
This is the biggest story in payments I can remember, and I write about payments for a living.
The details, per Reuters:
- $60.50 a share
- a 28% premium, backed by roughly $50bn in committed bank financing.
- Stripe and Advent would own PayPal 50/50 and keep the company whole.
- The first approach was April. PayPal hasn't responded yet.
The timing is poetic.
Last year was the first year Stripe's payment volume passed PayPal's. $1.9 trillion vs $1.79 trillion. The challenger passed the pioneer on volume, then went straight for the whole company.
Same volume, wildly different price tags. Stripe's tender offer in February valued it at $159bn.
PayPal peaked at $360bn in 2021 and just got bid at $53bn.
The gap is the growth rate: Stripe grew 34% last year, PayPal grew 7%. Growth is everything.
Advent's name in this deal tells you as much as Stripe's does. PayPal generated ~$6.4bn in adjusted free cash flow last year, so $53bn is roughly eight times cash flow.
That is private equity maths. Advent takes on the turnaround of a 23,800-person company.
And Stripe? Stripe spent 15 years building the merchant side of the internet. PayPal hands it the consumer side: 439 million active accounts, Venmo, and the yellow checkout button consumers know on sight.
If this closes, one company touches $3.7 trillion in annual payment volume. Around 3% of global GDP and would be by far the largest US merchant acquirer by volume.
My questions
- Can anyone fix the back end mess of PayPal?
- It's employee heavy, I image a lot of layoffs would be required?
- Is this actually a distraction for a very healthy growing Stripe?
- Would you keep bits and jettison others?
I get the attraction to the raw volume and assets. But underneath is a mess of company M&A and systems that never got fully integrated. Doing that is hard and not for the feint of heart!
There is no certainty it happens.
But someone just put $50bn of committed financing behind the idea that PayPal is worth more off the stock market than on it.
Discl: Stripe sponsors my podcast, opinions 100% my own – at Peschiera del Garda, Veneto
ditto. “tool slop” is a bigger problem than most would recognize (or say out loud)
big opportunity in ai-native services: software margin, service revenue, bridge the delivery gap
calanthia retweeted
"services don't scale"
> chases the $10k software budget inside companies
> watches openai kill the feature they built in 3 months
> cpo title before a paying user & 18 months burning runway
meanwhile services with ai inside:
> goes after the $120k services budget most people ignore
> every new model makes you faster, not obsolete
> operators going $0 to $40k/mo in 8 weeks running the same playbook
the full playbook to build "services-as-software" businesses:I
calanthia retweeted
Second exit in five years, and he engineered a deal structure almost nobody uses.
Ankur built Teachable in 2013, scaled it to $60M ARR, and sold it to Hotmart in 2021 for around $250M. He started Carry 18 months later with a specific thesis: the self-employed don't get the same wealth-building tools that full-time employees at big tech take for granted.
Three and a half years in, Carry has $225M in assets on platform, thousands of paying members, and a compliance moat around the hardest part of Solo 401k administration. Most founders run a single sale process and take the best bidder. Ankur closed two buyers in parallel transactions.
Lettuce got the retirement and investing platform. The Solo 401k infrastructure, the IRA custody, the $225M in AUM, plus co-founder Nick Rasch and the operations, product, engineering, and compliance teams. It slots directly into Lettuce's existing accounting, payroll, and healthcare stack for solopreneurs. Retirement was the one missing pillar of that whole solo-business finance experience.
AngelList got the other half. Carry's audience is accredited investors and high-earning founders, which is the exact overlap set AngelList already monetizes on the venture side. Extending from SPV and fund operations into the wealth management layer for the same people is the natural next step for their stack.
No single acquirer values both halves equally. Lettuce does not monetize an accredited investor brand. AngelList does not need a 1099 retirement compliance team. Running one sale process means someone underpays for the half they do not want. Running two means each half clears at its best-fit valuation.
The pattern underneath both exits is the same. Find an operator-buyer who can actually compound the asset. Sell when the product-market fit is obvious but distribution still has room to run. Teachable went to Hotmart, the Brazilian course platform that could globalize it. Carry went to the two companies that can each extend one half further than a standalone Carry could.
Most founders spend a career hoping for one exit. Ankur just closed his second, with a structure almost nobody in venture-backed SaaS thinks to try.
calanthia retweeted
Sequoia's thesis that the next $1T company will sell work, not software, is the most important reframe in AI right now.
The argument: if you sell a copilot, you're competing with every new model release. But if you sell the outcome — books closed, contracts reviewed, claims handled — every AI improvement makes your margins better, not your product obsolete.
The key insight most people miss: for every $1 spent on software, ~$6 is spent on services.
The entire SaaS playbook was about capturing the software dollar. The AI playbook is about capturing the services dollar — at software margins.
Not "AI for accountants." The AI accounting firm.
Not "AI for lawyers." The AI law firm.
The companies that figure this out won't look like SaaS companies. They'll look like services firms rebuilt on software infrastructure.
That's a fundamentally different company to build, fund, and scale. And most founders are still building copilots.
no shame in pivoting, or “ai redounding”
use your core assets and ride the macro wave. follow the 💰💰💰
Handshake has crossed $1B in gross revenue run-rate, up from ~$550M at the start of the year per The Information.
An incredible AI "refounding" from @GarrettLord and team to move into the AI data market under 1.5 years ago
i’m calling this the renaissance of smart generalists
ai-native, great at thinking, human-in-the-loop commander of agent workforces
The more enterprises I talk to about AI agent transformation, the more it’s clear that there is going to be a new type of role in most enterprises going forward. The job is to be the agent deployer and manager in teams. Here’s the rough JD:
This person will need to figure out what are the highest leverage set of workflows on a team are (either existing or new ones) where agents can actually drive significantly more value for the team and company.
In general, it’s going to be in areas where if you threw compute (in the form of agents) at a task you could either execute it 100X faster or do it 100X more times than before. Examples would be processing orders of magnitude more leads to hand them off to reps with extra customer signal, automating a contracting review and intake process, streamlining a client onboarding process to reduce as many straps as possible, setting up knowledge bases than the whole company taps into, and so on.
This person’s job is to figure out what the future state workflow needs to look like to drive this new form of automation, and how to connect up the various existing or new systems in such a way that this can be fulfilled. The gnarly part of the work is mapping structured and unstructured data flows, figuring out the ideal workflow, getting the agent the context it needs to do the work properly, figuring out where the human interfaces with the agent and at what steps, manages evals and reviews after any major model or data change, and runs and manages the agents on an ongoing basis tracking KPIs, and so on.
The person must be good at mapping the process and understanding where the value could be unlocked and be relatively technical, and has full autonomy to connect up business systems and drive automation. This means they’re comfortable with skills, MCP, CLIs, and so on, and the company believes it’s safe for them to do so. But also great operationally and at business.
It may be an existing person repositioned, or a totally net new person in the company. There will likely need to be one or more of these people on every team, so it’s not a centralized role per se. It may rile up into IT or an AI team, or live in the function and just have checkpoints with a central function.
This would also be a fantastic job for next gen hires who are leaning into AI, and are technical, to be able to go into. And for anyone concerned about engineers in the future, this will be an obvious area for these skills as well.
greg's $10m exit math checks out. i'm running this playbook now at 50% lower costs than he models.
ai-native agency runs on software margins from day 1. productization to saas later is an option, not the point. the outcome is the product.
wrote about it→calanthia.substack.com/p/sto…
THE CLEAREST PATH TO A $10M+ SOFTWARE EXIT in 2 YEARS (with AI and agents)
building an agency right now is one of the most interesting business moves
the productized agency had its moment in 2022. it collapsed because scaling humans is a nightmare. inconsistent output, people quitting, margins getting crushed. most of the founders (and creators) who tried it got burned and moved on
but the thesis was right. the labor problem is just solved now with AI, claude code, openclaw etc.
here's the actual playbook i'd run today:
pick one painful deliverable for one specific buyer. like SEO content for e-commerce brands doing $1M+ but not "marketing."
or like ad creatives for DTC brands spending $50k/month on meta. one thing. one customer. that's it
then you build the AI workflow behind it.
you're selling an outcome on a monthly retainer. $3-5k/month. 80%+ margins because your cost is compute and a few hours of QA
"BuT tHaT'S nOt a BiG bUsInnesS"
okay but you're still swinging for the fences
because the agency IS the research and development for your agent SaaS
every client is paying you to figure out what to automate. you're learning what breaks, what scales, what customers actually want.
by month 4 you know exactly what to productize. you build the software on top of the workflow you've already proven works and already have customers paying for
agency funds the agent SaaS. SaaS scales without the agency overhead. the clients become your first software customers
now let's talk about what this actually looks like financially
year 1: 10 clients at $4k/month. $480k revenue. 2 people. maybe $80k in costs including compute, tools, one part time VA. you're taking home $400k between two people while building the software in the background
year 2: you launch the software. your 10 agency clients are the first to convert. they already trust you. they've seen the output. you charge $800/month for the software version. now you have recurring software revenue AND the agency still running
year 3: agency is winding down or running on autopilot. software has 200 customers at $800/month. that's $1.9M ARR. 2-3 person team. 85% margins. you are now a very attractive acquisition target
the exit math is interesting. SaaS at $1.9M ARR with strong retention trades at 5-8x revenue. that's a $10-15M exit for something two people built in 3 years starting with zero VC
CAVEAT:
Startups are hard. A lot needs to go right.
But from a framework perspective, I think this probably the lowest risk, highest reward option for lots of of folks
and most of the businesses cost $0 to start
basically
this is the most capital efficient path to a software exit that exists right now
happy building
$85m into a firm. not a tool.
how it evolved: software used to sell to accountants. modus IS the accountant.
the ai-native service economy isn't a thesis anymore. lightspeed is writing checks against it.
Excited to announce our $85M fundraise from @lightspeedvp and investment in our first CPA firm. We're in the game now!
Full press release here: businesswire.com/news/home/2…
calanthia retweeted
wrote about this last friday. @JulienBek's piece is gold
tldr: stop building tools. start doing the work. for every $1 spent on software, $6 is spent on services
that's the real TAM: ai-native service economy is 6x bigger than saas
calanthia.substack.com/p/sto…
calanthia retweeted
What happens to the App Store when vibe coding makes building apps 100× faster and cheaper?
A few things I think start to happen:
1. Apps increasingly launch for very specific moments instead of trying to keep users forever. You download it, get value, and move on.
2. Apps that solve a problem in under 30 seconds convert 2–3× better than apps that require onboarding.
3. A new pricing norm emerges: ~$1–$10 for one moment of value, paid instantly, with no expectation of future use. Disposable apps.
4. More examples of revenue concentrating at the account level, not the app level. You'll see seven/eight/even 9 igures across dozens of micro-apps.
5. Some of the most valuable apps never appear in App Store rankings because they spread peer-to-peer and are super niche.
6. Founders start shipping 10-20 micro-apps per year, expecting 1–2 to stick, instead of betting everything on one product.
7. The average successful app team trends toward 1–2 people, even at $1–5M ARR, because product surfaces stay small.
8. Distribution shifts toward people with trust. Creators, communities, and group chats quietly become the real app curators.
9. More extremely niche apps that didn't make sense to build are now being launched
10. Apps get named like content, not companies. Short, emotional, contextual names win.
11. App naming converges toward 5–8 character names because they perform better in links, sharing, and memory.
12. Apps win on tone and identity more than features. Two apps can do the same thing, but one feels like it’s “for you.”
13. The fastest growing category becomes “utility + identity” apps, tools that also signal taste or values.
14. Personalization becomes default. The same underlying app shows up in different versions depending on who you are and why you’re using it.
15. Launches start to look like content drops. Timing, story, and where an app shows up matter more than the tech itself.
16. Successful apps group into small bundles that match a lifestyle, job, or niche instead of standing alone.
17. Apple leans harder into bundles and curated experiences, acting more like a trusted editor than a giant directory.
18. Apple quietly favors apps that fit healthy usage patterns because it aligns with device trust.
19. Mobile vibe coding pushes creation onto the phone itself. People build apps while waiting, walking, or thinking, not sitting at a desk. Realistically not everyone will want to create apps, but 100x+ more do.
20. App fatigue increases, but software usefulness improves. People delete more apps and feel better about the ones they keep.
21. Over time, people stop saying “I use this app” and start saying “I made a small app for that.”
calanthia retweeted
Apple JUST quietly announced something that’s a lot BIGGER than it looks: "the Mini Apps Partner Program"
Apple is admitting that the future of software is embedded, lightweight, vertical mini-apps distributed inside bigger app
For founders who want to make $$ building apps:
1. Apple just legitimized the “superapp” model for the West.
China has WeChat mini-programs. India has PhonePe Switch. The West has… nothing. Apple just opened the door. You can now run HTML/JS mini-apps inside a native host and earn 85% on qualifying purchases. That’s Apple-sanctioned platform piggybacking.
2. Distribution arbitrage becomes real again.
You don’t need to convince users to download your app. Just partner with a host app and drop in a mini-app. This is a cheat code for early traction. Think: travel apps hosting niche tools, fitness apps hosting mini workouts, marketplaces hosting micro-utilities.
3. Apple is creating a new economy layer: “embedded SaaS.”
Imagine: CRM mini-apps inside vertical tools. Math solver mini-apps inside education apps. Calendar mini-apps inside productivity apps. The TAM for tools that don’t need standalone installs just went vertical.
4. Developers get an 85% revenue share.
This is Apple basically saying: “We want this ecosystem to grow, and we’re willing to cut our take rate.” When Apple lowers its cut, I pay attention because they see a platform shift coming.
5. AI makes this 10× more important.
LLM-powered micro-apps (calculators, planners, agents, coaches, niche utilities) are tiny by design. They’re perfect mini-apps. Apple just created infrastructure for AI-native micro utilities to live inside bigger apps with built-in commerce.
6. Host apps become new “distribution landlords.”
If you own an app with traffic, you become a platform. You can host mini-apps, take a cut, and build a developer ecosystem around you.
It’s a new monetization model for existing apps with audiences.
7. This unlocks a wave of second-order opportunities.
- Agencies helping apps become mini-app hosts
- Mini-app dev shops
- “Shopify for mini-apps” toolkits
- Mini-app marketplaces
- Analytics for mini-app performance
- Discovery engines for mini-apps
- I'll be dropping mini app ideas on @ideabrowser and @startupideaspod
TLDR;
Apple just turned every high-traffic app into a potential superapp and every indie developer into a potential platform partner.
The App Store is becoming modular, composable, and layered. The next decade of consumer apps will look less like standalone products and more like ecosystems stitched together with mini-apps.
This is quietly one of the biggest distribution unlocks in years.
calanthia retweeted
Everyone is asking how AI startups survive when the foundation models move this fast.
Don’t sell picks and shovels, own the mine.
Become the incumbent by using AI to vertically integrate the entire stack and capture all the value end-to-end.
Examples:
– An AI brokerage that builds and uses its software to sell policies, then starts its own brokerage
– An AI recruiter that builds sourcing tools, then becomes the staffing agency
– An AI construction platform that optimizes bids, then spins up its own GC arm
– An AI pharmacy platform that automates prior auths, then vertically integrates dispensing
I'm seeing more and more of these verticalized vertical software companies coming out to raise venture in a traditionally PE-backed space.
calanthia retweeted
Google Docs has launched "Listen to this tab," where you can have any doc read aloud to you (with your choice of voice).
I find most of the G Suite AI integrations a little...annoying - but this is pretty cool! 👇
Spoilers for our Top 100 Gen AI list coming out next week 👀
