There’s now a whole group of companies I’ve invested in, and/or been an advisor or board member or other close relationship with … that are hitting or have recently crossed 4 Years Old. Including the 2022 cohort that built through SaaSmageddon and is now in the middle of rebooting their entire company for the AI era.
Interestingly, only a few have more ARR than I did 4 years in. But almost all of them are growing much faster. So within 12-18 months, they will quickly eclipse where I was at their stage. The difference? Often, they had little to no revenues in the first year or two. They took longer to get to product-market fit. I had my own challenges, but we had good customers and real revenues 6-9 months into our first year. Our challenges were otherwise, with hindsight.
And I think there are two reasons these B2B companies are growing faster at Year 4 than I ever did.
One is simply that the B2B markets are so much bigger today. AI makes it true even more so.. So even if it takes you 2 years to get to true product-market fit, if you really achieve it … you should be able to grow faster. The markets are 10x larger than 5 years ago and 100x+ larger than 10 years ago. And in 2026, AI has expanded the addressable problems even further. Even with more competition, unless it approaches perfect competition, you should be able to grow faster.
But Key factor #2 why they are growing faster at Year 4 than I did is that these founders are just Indefatigable. They may be tired, they may struggle to hit their lofty goals for the month and the quarter. But they simply cannot be stopped. At Year 4, they are Just Getting Good. Versus really, most of us start to approach potential burnout in Year 4.
And Right Now, I’m Seeing a Lot of Founders Struggling to Reboot for the AI Era
This is the new variable in 2026, and it’s a brutal one.
A whole cohort of founders who built really good B2B businesses from 2020-2023 are now trying to rebuild the entire company on top of AI. New product. New pricing (often outcome-based, not seats). New go-to-market motion. New competitor set, with AI-native startups showing up in deals at 1/3 the price and 3x the speed. New ICP in some cases. And they’re trying to do all of this while still hitting the plan for the existing business.
Will they pull it off?
Honestly … only if they’re indefatigable.
Because here’s what an AI reboot actually looks like from the founder seat:
- You’re rewriting the product roadmap for the third time in 18 months
- Half your engineering team needs to be retrained, and a chunk of them quietly don’t want to be
- Your VP of Sales is selling a product that’s mid-pivot
- Your existing customers are asking for AI features you haven’t shipped yet, and your competitors’ decks all claim they have them
- The board wants to see the AI strategy at every meeting, but also wants the plan hit
- And you, personally, need to become an expert in agents, evals, model selection, and AI GTM while still running the company
That is a Year 5 problem stacked on top of a Year 4 burnout curve. It is brutal.
I see burnout much more commonly in “fairly successful” entrepreneurs … the ones growing, just not that quickly. Much more often than burnout among the failed ones. And usually starting around Year 3. Building in Year 4. And then it hits hard in Year 5.
First, it’s hard(er) to fail slowly. It definitely happens all the time, but true failure more often happens quickly. You never get out of WeWork (or in 2026, never get out of the spare bedroom). The angel money is gone, and you have no customers. Etc. etc. This usually happens in the first year, or the second.
Great founders that fail fairly quickly seem to bounce back. With a lot of scar tissue sometimes, yes. But with less true burnout. They tend to be ready to do the next one. Like. Now. And in 2026, often the next one is just an AI-native rebuild of the idea that didn’t work the first time.
The Slow Success is different. There, I find it’s around Year 4 that true burnout sets in. And boils over in Year 5:
- Year 1: excitement. Near death every day, but excitement. No true fatigue.
- Year 2: (if you make it): paranoia, terror. You don’t have enough revenue / customers / users to really succeed. But you did get to Year 2.
- Year 3: the slugfest starts. You won’t fail. You got to Year 3. But man … it’s gonna take a loooong time to get to $10m ARR. Or $5m. Or wherever. It took you 3 years to figure this out. Burnout just begins now.
- Year 4: slugfest, part II. Burnout sets in. And now you’re also rebuilding the product for the AI era while an AI-native competitor is showing up in your deals at half the price.
- Year 5: slugfest, part III. Now you’re really burnt 3 years into the slugfest. And the AI reboot you started in Year 4 isn’t done yet.
So what you see, which is often a shame, is founders leaving successful companies in Year 5. Often. All the time. And in 2026 specifically, often selling to a strategic for less than they should, because they just can’t run another marathon. Or worse, they stay, but they quietly stop pushing on the AI reboot. They ship the AI features the board demanded, slap a “Powered by AI” on the homepage, and hope the existing motion carries them another 18 months. It won’t.
So Who Pulls Off the Reboot?
The indefatigable ones. Full stop.
Not the smartest. Not the most technical. Not the ones with the cleanest cap table. The ones who, in Year 4, still wake up at 6am genuinely excited to figure out how agents are going to change their category. The ones who treat the AI reboot as Year 1 energy applied to a Year 4 company.
That’s a very small group. And it’s who I want to invest in, and back, right now.
What You Can Actually Do About It
Make sure this doesn’t happen to you. You can’t 100% control your absolute growth rate, not always. You can inflect the curve. But you can’t will your startup into the Next Twilio. Or the Next Cursor. As much as we’d like to think we can. But there is one thing you can do to avoid hitting a wall.
The key is just one thing, really. Recruiting a strong enough team to carry a lot of the load.
In 2026, that means two things now, not one. First, you still need real human VPs in the key seats: sales, engineering, customer success, product that truly are AI-native.
The AI reboot does not let you off the hook on this one. If anything it makes it more important, because rebuilding the company while running it requires more leverage at the top, not less.
Second, you must build the winning AI Agent(s) in your space. This is the new part, and it’s the one many founders are getting wrong.
The winning move in the AI reboot is not “we added AI features.” It’s not a chatbot on your website. It’s not GPT in your search bar. It’s not even using AI agents internally to make your team more efficient (though you should do that too — at SaaStr we run with 3 humans and 20+ AI agents, and it’s how we have any energy left at all).
The winning move is being the clear #1 AI Agent in your category. The one that comes up first when a buyer in your target market asks “which tool has the best AI for [your space].” The one that takes over a meaningful customer workflow end-to-end, with results good enough that a customer would rather use your agent than hire a person to do the same task. That is the bar.
You have advantages an AI-native startup does not. You have the data. You have the workflows. You have the domain expertise. You have the customer relationships. You have four years of compounded learning about how customers in your category actually operate. Your moat is enormous … but only if you actually use it to build the best AI agent in your space before someone else does.
If you don’t, an AI-native competitor will show up in your deals at 1/3 the price doing 80% of what you do, and they will eat the mid-market and SMB first, then come for the enterprise. That is the existential threat. And no amount of “AI-powered” marketing copy is going to save you from it.
The founders pulling off the reboot right now are the ones treating this as their #1 priority. Often they’re isolating their best engineers in a different building, away from the well-meaning internal antibodies who will slow-walk it to death. They’re cannibalizing their own product on purpose, because they know if they don’t, someone else will. They’re running two full-time jobs at scale: protecting the installed base, and shipping the winning agent in their space. Neither one pauses while they focus on the other.
That takes indefatigable energy. There is no other way through.
And I think I’ve learned from an investment perspective, in B2B, you have to invest in indefatigable founders. Especially now. Because the founders who survive to Year 7 and Year 10 in this market are the ones who built the team early enough that Year 4 doesn’t break them … and who have the energy left to ship the winning AI Agent in their category before an AI-native startup does it for them. Which, in 2026, is the only reboot that actually matters.
