Dear SaaStr: As a Co-Founder, How Do I Tell the Team I’m Leaving?
Dear SaaStr: As a startup founder, what’s the best way to announce your departure to the team and leave on good terms? The startup is series A/B, with 30+ employees. I have no magic insights, but I have transitioned post-acquisition out of 2 companies that...
The Navan IPO Reminds Us: AI is On Fire. Everything Else in B2B? Still Really, Really Hard.
So Navan finally went public in Q4’25. After years of confidential filings, pushed timelines, and a rebrand from TripActions, they rang the bell on October 30th, 2025. And then the stock dropped 20% on Day One. Today? It’s trading around $17. That’s 32%...
Dear SaaStr: What’s The Best Way to Get Traction After We Have Our First Few Paying Customers?
Dear SaaStr: What’s The Best Way to Get Traction After We Have A Few Paying Customers? Answer: try everything that just might work, even a little bit. Then: double down on anything that works even a little. That may sound obvious, but what I mean is, most start-ups...
Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity
Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity; what should I do? Generally, this is the last, best chance to fix things. Founder equity splits are a tough thing. What seems fair on Day 0 may seem less fair on Day 720. The one that...
Dear SaaStr: When Bootstrapping a SaaS Product, What Should You Be Aware Of?
Dear SaaStr: When Bootstrapping a SaaS Product, What Should You Be Aware Of? Just a few observations from bootstrapped B2B companies I’ve had some involvement with: It probably will take 1–4 years longer to get to $10m ARR or so. I don’t fully have the data to support...
Dear SaaStr: A Big Tech Co Launched a Competitive Product. How Can I Tell How Serious They Are About It?
Dear SaaStr: A Big Tech Co Launched a Competitive Product. How Can I Tell How Serious They Are About It? In SaaS at least, I’ll give you one metric that is fairly reliable: How many dedicated sales and GTM professional do they have, just 100% selling the competitive...
Dear SaaStr: Is Launching Your SaaS Product Too Early Really A Big Issue?
Dear SaaStr: Is Launching Your SaaS Product Too Early Really A Big Issue? This is a tough one. Wait too long, you run out of time and money in many cases. Launch too quickly, you burn your earliest and often most passionate users and fans. I made this mistake with...
Dear SaaStr: How Can I Give Better SaaS Product Demos?
Dear SaaStr: How Can I Give Better SaaS Product Demos? One simple answer: train your reps more. A lot more. With most SaaS companies, for a while, demos get worse: At first, founders do all the demos. The demos themselves are a bit rambling, too long — but...
Dear SaaStr: How Do I Compete with a Company that has Unlimited Capital — and I Don’t?
Dear SaaStr: How Do I Compete with a Company that has Unlimited Capital — and I Don’t? First, does your highly-funded competitor have a dominant brand yet? If not, it may not matter. There is no “winner” yet. The #1 brand trumps capital. But if they have...
Dear SaaStr: What Are The Top 5 Things I Should Know Before Starting a SaaS Startup?
Dear SaaStr: What Are The Top 5 Things I Should Know Before Starting a SaaS Startup? My Top 5: It will take you at least 24 months to really get anywhere. Everyone mentally budgets 10–12 months. It’s never enough. At least, not to get enough paying customers from Code...
Notion at $11 Billion: The Art of Growing Into Your Valuation — And After 14 Years, Into One Of The Next Great B2B IPOs
The numbers tell one of the most important stories in B2B right now. Notion just kicked off an employee share sale at an $11 billion valuation. That’s just 10% above their October 2021 price—after four years. But here’s what changed: revenue grew ~20x....
Dear SaaStr: What Do You Do When Your Startup is Not Growing Anymore?
Dear SaaStr: What Do You Do When Your Startup is Not Growing Anymore? First, be honest about why. You can blame it on macro issues if you want, or on the competition over promising, or whatever — but if growth has radically decelerated, it’s likely because you...
Even A Slightly Too High Burn Rate Can Get Out of Control
There’s a pattern I see again and again, probably with 30% of venture-backed start-ups, maybe 40%. Their burn rate sneaks up on them, and becomes a bit out of control — without feeling like it. This usually doesn’t happen in the very early days,...
Dear SaaStr: What’s the #1 Way I Can Accelerate My Career Growth?
Dear SaaStr: What’s the #1 Way I Can Accelerate My Career Growth? My uber-learnings: Find the best boss you can; and Take on every initiative, project, task, and endeavor you possibly can from her. And work for them for a while. Long enough to get promoted once,...
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