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Probably a good time for a introduction …
25+ years building, buying and selling software companies.
Multiple exits. A couple flops.
12+ acquisitions, including one 4x our size.
My first exit took 14 years.
Author of The Adaptive Innovator.
Now:
1.) CEO of Conquer. Sales voice and communications technology for enterprise sales teams.
2.) Managing Partner at Evergreen Mountain Equity Partners. We buy B2B SaaS.
3.) Executive Chairman of Outsorcy. Global teams for US software companies.
I write for founders past $5M:
-> scaling without being the bottleneck
-> what buyers check before they pay
-> M&A from the buyer's seat
-> rebuilding around AI instead of bolting it on
I try and share all the founder lessons I can remember. Follow along.
Deal volume isn’t the problem. The portfolio assets are broken.
A lot of software got bought on the assumption that seat revenue compounds.
Then AI broke that assumption.
If you run a $5M+ company and want an exit in the next few years, you’re going to have to rebuild the model. There will be no plan B.
Sad reality …
AI either makes you smarter and faster or dumber and slow.
There is really no in between.
Sierra prices on outcomes. Legacy SaaS prices on seats. That's a major gap.
If you run a $5M+ SaaS business, stop asking "what's our AI feature?” Start asking what job you finish for the customer … and what’s the value of the job being done.
My first exit took 14 years.
The risky part wasn't the bet. It was actually staying in when every safe option looked was better.
You don't fail from playing it safe. You fail by quitting too early.
Reminder... no one ever got rich by playing it safe.
Elon Musk had to borrow money from friends to keep Tesla alive in 2008.
Walt Disney borrowed against his own life insurance policy to help fund Disneyland.
Daymond John mortgaged his mom's house to fund FUBU.
Sara Blakely put her entire savings into Spanx.
Definitely not a scandal. But it’s late. And it’s the same problem at countless companies.
Everyone uses AI. But productivity still hasn't budged.
They sped up the old workflow instead of rebuilding it.
Every legacy company is stuck right there.
I've been the buyer in 12+ acquisitions and I’m 100% certain of one thing …
Deals close on price and terms.
They work or DIE on alignment.
I've watched an entire founding team walk out in one day because we never agreed on what we were building together.
It extends beyond just the teams getting acquired. Same for investors. If all are not in sync on what the business looks like 3 years down the line post deal, don’t do it.
Any upside is quickly lost when no one agrees on the future state direction and vision.
Shockingly easy to convince yourself you’ll fix it later. Trust me … you won’t without a lot of pain.
Greg is right. And it's why legacy SaaS is in deep sh*t.
Their whole P&L is seats. They can't give the tool away without blowing up the model.
AI-native companies can. Start free. Charge for the work.
Incumbents won't cannibalize themselves. At least for now.
teapawt.org/gregisenberg/status/21…
We’re seeing this firsthand at Outsorcy, where recruiting is our core business.
We’ve started using AI to turn recorded interviews, job requirements, and scorecards into candidate summaries in seconds. We’re also incorporating AI capability assessments into our hiring process.
What’s interesting to me is how quickly this changes the economics of hiring.
But I think the bigger opportunity goes beyond eliminating a $125K role. It’s rethinking what recruiters spend their time doing.
Less administration. More time understanding clients, evaluating talent, and making better matches.
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A couple years ago Ira Grossman and I wrote The Adaptive Innovator. This is exactly what we explored.
The defining factor of world class founders isn’t so much confidence … it’s about learning to challenge your own assumptions, particularly when fear and uncertainty are your daily worldview.
The most adaptive founders aren’t necessarily the most fearless. They get just as scared as anyone else. But, they’ve learned to separate perceive risk from outsized opportunity. Risk doesn’t overwhelm opportunity. It’s just something to manage.
The good news … anyone can develop that skill. And as a founder, it may be the most important.
Amazon founder Jeff Bezos has a surprising theory about the "confidence" behind great founders: it might not be confidence at all.
When the idea of confidence comes up, Bezos offers a different explanation:
"You say it's confidence, but maybe it's just trying to compensate for that... accepting that that's a human bias and trying to compensate against it."
So what is the bias?
"I think it's generally human nature to overestimate risk and underestimate opportunity."
Your instincts don't just make the risks look bigger than they are. They also make the opportunities look smaller than they are. Both errors push you in the same direction: toward doing less.
Bezos's correction:
"The risks are probably not as big as you perceive and the opportunities may be bigger than you perceive."
This is why he says entrepreneurs "would be well advised to try and bias against that piece of human nature."
Seen this way, the founder who looks fearless may not have a different personality from you.
They may simply have accepted that their instincts are tilted and learned to adjust for it on purpose. That's not a trait you're born with. It's a correction you can choose to make.
And if you don't make it, @JeffBezos warns there's a cost:
"Thinking small is a self-fulfilling prophecy."
Let the bias set your ambitions, and you'll get small results that seem to prove small was all that was possible.
The wall between “serious software development” and vibe-coded v1’s is going to fall fast.
Why spend six months building an enterprise grade product before you know if anyone actually wants it?
Vibe coding a V1 lets you get something into the market, test demand, learn from real customers and measure outcomes in weeks.
If it gets traction, awesome, invest in the architecture, security, and scalability it needs. If it doesn’t, move on.
I’ve built software companies the traditional way for years. That old development playbook makes no sense anymore.
"No one serious is going to use MailCheap"
"You can't vibe code a profitable SaaS"
"MailCheap is dead next week"
Do what you can't.
MailCheap.AI
I think the bigger question is what actually becomes defensible.
We’ve spent years building SaaS businesses around proprietary software. AI makes us rethink that entire assumption.
I’m increasingly convinced the advantage will come from deeply understanding a customer’s domain, workflow, owning the relationship (proprietary distribution), and continuously improving the outcome (owning the results).
That ability to deliver results consistently is a real moat.
We have to get comfortable knowing the next generation of great AI companies looks a lot more like tech-enabled services than traditional SaaS.
Never say domain expertise is meaningless. There are niches everyone if you look … even hair braiding.
A Harvard engineer just raised $7M to build a robot that braids hair up to 5x faster than human stylists.
Her name is Yinka Ogunbiyi, a Nigerian American engineer, and her invention HaloBraid is being called the world's first air powered braiding robot.
She built it to take the physical strain off hairstylists who stand for hours on every client, and to help salons get more done in less time.
More than 7,000 salons are already on the waitlist.
5,000 years of braiding history just met its first robot.
Legacy SaaS has talent. It has capital.
It doesn't have speed.
You can't build a new business model inside an org built for the old one. I’ve tried it. Over and over. It doesn’t work.
Seat pricing. Roadmaps owned by your biggest customers. Code nobody understands and doesn’t want to touch. Decisions that take a quarter. It’s the swamp of an established company.
AI-native startups ship in weeks.
Stop trying to turn the mothership. Build new ships.
Teams of 2 to 5. Their own code. Their own P&L. One customer problem each. Ship it, sell it, watch the numbers.
No signal? Kill it.
Real signal? Push hard.
The parent brings capital and distribution and customer base to sell into. It DOES NOT bring its operating model.
The biggest liability in legacy SaaS isn't technical debt anymore. It's organizational debt.
You can rewrite code in a quarter. Fixing an org takes years.
This is a real operating shift. The bottleneck is founder judgment + the ability to design workflows that actually stay aligned.
Curious how many founders are already running meaningfully flatter orgs because of this.
Marc Andreessen explains why AI might be the end of James Burnham's "managerial society"
In his book The Managerial Revolution, Burnham divided capitalism into two phases.
The first phase was what he called "bourgeois capitalism"
"Think of this as name on the door -- it's Ford Motor Company because Henry Ford runs the company. It's a dictatorial model and Henry Ford just tells everyone what to do. He said the problem with bourgeois capitalism is it doesn't scale because Henry Ford can only tell so many people to do so many things."
The second phase was what Burnham called "managerial capitalism", which was Marc describes as, "the creation of a professional class of managers that are trained -- not to be car experts or experts in any particular field but to be experts in management. And then that led to business schools and management consultant firms and all these things."
Marc continues:
"You look at every big company today and most executives at most of the Fortune 500 companies are not domain experts in whatever the company does. And they're certainly not the founders of those companies. They're professional managers. And in fact, over the course of their careers, they'll probably manage many different kinds of businesses. They might work in healthcare for a while and then work in financial services and then go work in something else."
"What Burnham said was that transition was absolutely required because the problem with bourgeois capitalism is it doesn't scale... So if you're going to run capitalist enterprises that are going to have millions to billions of customers, they're going to be operating at a level of scale and complexity that will require this professional management class."
Burnham acknowledged that this professional management class has its downsides -- they're not as inventive and not going to come up with the next breakthrough. But whether you think that's good or bad, that's what's going to be required.
And basically that's what happened. Marc continues:
"Managerialism basically took over everything. What I'm describing is basically how all big companies run and how all governments run and how our large-scale non-profits run."
Marc believes venture capital is a protest movement to that -- backing founders under the Henry Ford model, and trying to find the next Elon Musk or Steve Jobs who can out-innovate the incumbents.
"I've always viewed my entire life as: we're raging against the dying of the light. We're constantly trying to fight off managerialism from swamping everything and everything getting boring, gray, dumb, and old."
But AI may now offer a third model. Marc explains:
"Maybe the new Henry Ford, Elon Musk, or Steve Jobs + AI is the best of both because it's the spark of genius of the name on the door model but gives that person AI superpowers to do all the managerial stuff... What's the thing these bots are really good at? They're really good at doing paperwork, writing reports, and doing all the managerial work."
"The challenge is going to be for the innovators to figure out how to leverage AI to actually do this."
"The other challenge is going to be for the incumbents that are managerial to figure out: what does that mean? Because now they're going to be facing a different kind of insurgent competitor that has a different set of capabilities than they're used to."
"I think this is going to force a lot of big companies to figure out innovation - figure out innovation or die trying."
Ben Horowitz elaborates on this point further in his article Databricks & the Future Firm below.
Video: @latentspacepod (Apr 2026)
STOP list for SaaS founders in the agent era:
STOP selling seats.
STOP shipping dashboards nobody opens.
STOP pricing the workflow.
STOP calling usage a business model.
START owning a single outcome you can put a dollar on.
Love Xai, grok bot etc but @elonmusk trying to figure out what you’re buying and how to do it is nearly impossible.












