2021 spoiled us. For a while, you could have it all. You could work from home 15-20 hours a week and hit plan. You could have 2-3 side hustles and still be on track. The markets were booming, customers were buying at an unprecedented rate, and the products …. were basically the same.
The B2B products of 2021 were basically the same as they’d been for years. Just with 2x or more the demand. So life was good and … easy.
Today, good times are back again. Better and bigger than ever. But now is in many ways the exact opposite of 2021. The pace of change is the most furious we’ve ever since in software in the age of AI. Utterly furious.
So there’s a tough truth most have now accepted — partially. Partially: That you can’t have it all anymore. You can go for it, or you can have balance. Not both.
And it’s only going to get more stark, as more and more companies look to replace humans with AIs. At SaaStr, every resource we’ve lost or moved on from since late 2024 has been replaced with AI.
The Two Types of B2B Execs (And Only Two)
We’ve broken into two distinct categories of startup executives and opportunities:
The Cracked: These are the leaders who’ve accepted that building something truly extraordinary in 2025 requires an obsessive, all-consuming focus. They’re working 70-80 hour weeks, they’re thinking about their product at 2 AM, they’re available for the critical customer call on Sunday morning. They’re not balanced. They’re not well-rounded. But they’re building the companies that will define the next decade.
The Slow Roll: These are the executives who prioritize work-life balance, who want their 35-40 hour weeks, who need their weekends protected, who want to work remotely most days. And you know what? Good for them. Seriously. Life is short, family matters, mental health is real. But they’re not building the next Stripe, OpenAI, Harvey, Replit/Lovable, or Notion.
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The Uncomfortable Math of Modern AI Startup Success
Here’s where it gets uncomfortable. I know many folks want something in the middle. We all do, myself included. The dream scenario:
- A solid 35-40 hours a week
- 1-2 days in the office max
- Weekends completely off
- Still land that $10B+ outcome
I’ve been looking for these opportunities for my portfolio companies, for executives I advise, for myself. And the brutal truth? I just don’t see any of those opportunities anymore in high-growth companies.
In 2021? Absolutely. The market was frothy, money was cheap, competition was lighter, and you could coast a bit and still win big. Remote work was new and exciting, not a productivity drag. AI wasn’t eating everyone’s lunch yet.
Today? Zilch.
In fact, every start-up I work with focused on balance is losing. Maybe losing slowly, a few points of market share here and there. But they are losing.
Why 2025-2026 Is Different (And Harder)
The world fundamentally changed between 2021 and now. Here’s what’s driving this new reality:
AI Has Accelerated Everything: Your competitors aren’t just working faster—they’re using AI to work 10x faster. The startup that’s willing to integrate AI into every process, every decision, every customer interaction is going to lap the one that treats it as a side project.
Growth Insanity: The best of the best in AI B2B are growing at rates we’ve never seen before. That just ratchets up the expecations everywhere. From making raising VC harder, to expectations for top execs and employees.
Customer Expectations: B2B buyers expect AI-powered solutions, instant responses, and continuous innovation. If that’s not you, everyone will see you as too slow. As dated. You probably are.
The Balance Trap
Here’s what I see happening with “balanced” startup teams:
- Slower Decision Making: When your leadership team isn’t available nights and weekends, critical decisions wait until Monday
- Missed Opportunities: That enterprise customer who wants to talk at 7 PM Pacific? The European prospect who needs a demo at 6 AM your time? The Slow Roll team misses these
- Innovation Lag: While you’re protecting work-life balance, your competitors are iterating, testing, and shipping
- Talent Disadvantage: The best engineers, salespeople, and operators want to work with obsessed leaders who are going after massive opportunities
If You Want Balance, Here’s Your Path
I’m not saying balance is wrong. I’m saying be honest about what it means for your outcome.
If you want genuine work-life balance in startups, you need to:
Join something barely growing or slow growing that’s explicitly focused on providing that balance. There are companies out there—profitable SaaS businesses growing 15-20% annually, lifestyle businesses, companies in maintenance mode. They can offer balance because they’re not fighting for market leadership.
Accept smaller outcomes. Maybe you build a $50M ARR business instead of a $500M one. Maybe you have a $100M exit instead of a $1B one. That’s still an incredible achievement and a life-changing outcome for many people.
Target different markets. Some industries and customer segments move slower. Government contracts, certain enterprise segments, regulated industries—these can still support more balanced approaches.
The Cracked Path Isn’t for Everyone (And That’s OK)
Being “Cracked” isn’t just about working more hours. It’s about:
- Obsessive customer focus that has you thinking about user problems in the shower
- Relentless iteration where you’re constantly testing, learning, and improving
- Extreme ownership where every metric, every outcome, every failure is personally felt
- Visionary leadership where you’re seeing opportunities others miss because you’re deeply immersed
This path breaks people. It destroys relationships. It’s not sustainable forever. And it’s not morally superior to choosing balance.
But if you want to build something truly extraordinary in today’s environment, this is what it takes.
The Extreme Example: Cognition’s Brutal Honesty
Want to see exactly what “Cracked” looks like in 2025? Look at Cognition, the AI coding startup behind Devin.
Three weeks after acquiring rival Windsurf, Cognition laid off 30 employees and offered buyouts to the remaining 200 staff members. The terms for those who stay? Six days at the office and more than 80-hour weeks.
Here’s the kicker—Cognition CEO Scott Wu didn’t sugarcoat it: “We don’t believe in work-life balance—building the future of software engineering is a mission we all care so deeply about that we couldn’t possibly separate the two.”
This isn’t some toxic startup culture run amok. This is what The Information calls “table stakes among workers at top AI firms.” When you’re competing to build the future of software engineering against OpenAI, Google, and others, this is what it takes.
Is it extreme? Absolutely. Is it sustainable for everyone? Of course not. But is it what winning looks like in today’s AI arms race? Yes. Cognition is in a brutal arms race with Claude Code, Cursor, and more. You have to outpace the best-of-the-best now. That’s … hard.
The Hard Truth About Competition in AI Age
The world is just too competitive today, too fast, and too hard for half-measures.
Your competitors who choose the Cracked path aren’t just working more hours—they’re:
- Making faster decisions
- Taking bigger risks
- Attracting better talent
- Raising money more easily
- Winning more customers
- Building stronger products
Meanwhile, AI is making the fast faster, the smart smarter, and the obsessed more obsessed.
Choose Your Path (But Choose Consciously)
Here’s my advice: Choose your path consciously, not by default.
If you choose balance:
- Join companies explicitly built for it
- Target markets that support it
- Accept the outcome implications
- Don’t resent the Cracked teams for their success
If you choose to go Cracked:
- Accept the personal costs
- Build systems to prevent burnout
- Remember it’s not permanent
- Don’t judge others for choosing differently
Just don’t pretend. Not anymore. That will lead to frustration all around. And probably, you getting let go. You cannot have it all in the AI age. Because the competition won’t let you.
If you want to go for the big outcome, the gold, the glory … expect to work 60+ hours a week in the office. And managing a smaller team, if any team at all. And being a 100% expert in AI orchestration. There will be some exceptions. But … few.
Two Paths, But They Don’t Much Crossover Anymore
We’re in a new era where the middle ground has disappeared. The companies winning big are led by obsessed teams who’ve sacrificed balance for breakthrough outcomes. The companies offering balance are optimizing for different goals.
Both paths are valid. Both have their place. But pretending you can have both in today’s market isn’t helping anyone.
The sooner we’re honest about this trade-off, the sooner we can make conscious decisions about which path aligns with our goals, our values, and our life stage.
Join that world, or maybe, join someone being left behind.
Yes, it’s tough. But at least it’s honest.
