Dear SaaStr: What Are Some of the Qualities of a “Bad” Startup CEO?
Dear SaaStr: What are some qualities of a bad startup CEO/founder in Silicon Valley? A few that I’ve seen across the handful of investments I’ve made … that didn’t work out: Not really committed to going long. This doesn’t so much make you a “bad” CEO as one that...
20VC x SaaStr Are Back: If Figma Isn’t Good Enough, What Hope Is There? Plus OpenAI Ads, Elon vs. Sam, and the $9B Replit Bet
With Harry Stebbings, Jason Lemkin, and Rory O’Driscoll If Figma—one of the best products in SaaS history—can’t sustain its IPO price, what does that mean for the rest of us? That’s the question that kicked off this week’s episode, and it led...
Should You Pay Reps More For Deals They Hunt Themselves? Sometimes. Here’s When.
Dear SaaStr: Should sales reps be compensated differently based on how much prospecting they do? For example, if all of their leads come inbound (without effort on their part) should they receive a lesser % per deal vs a rep that prospects for their own leads? It...
Dear SaaStr: Should We Pay Our Sales Reps on Renewals?
Dear SaaStr: Should We Pay Our Sales Reps on Renewals? Simple answer: most don’t. You can, especially in the early days. But very few SaaS companies pay sales reps on renewals as they scale. And you can definitely pay on upsells and account expansion. Longer...
Should You Hire a Sales Rep First, Or a Sales Manager?
Dear SaaStr: Should I Hire a Sales Rep First, Or a Sales Manager First? The ideal flow is: You (founder-CEO) close the first batch of customers, say the first 10 or 20. If you don’t, you’ll never really know how it’s done. Or be able to help anyone else, really. Then,...
20VC x SaaStr This Week: Anthropic at $350B, OpenAI’s Existential Risk, and Why a16z’s $15B Fund Actually Makes Mathematical Sense
A deep dive into the biggest AI rounds, the future of venture capital, and why California’s wealth tax could trigger a founder exodus We just wrapped another 20VC + SaaStr pod with Harry Stebbings and Rory O’Driscoll from Scale Venture Partners, and this...
Dear SaaStr: What Happens if a VC Loses All Their Money on an Investment?
Dear SaaStr: What Happens if a VC Loses All Their Money on an Investment? It’s OK — if it’s not too much. As long as the founders did everything they possibly could to make it work. Everything. And were honest. There are two types of losses for VCs...
Dear SaaStr: How Do You Deal With an Unreliable Co-Founder?
Dear SaaStr: How Do You Deal With an Unreliable Co-Founder? You first try to move them into an individual contributor role. If that doesn’t work, then move them out. This is one of the most frustrating outcomes, when a very talented co-founder becomes “unrealiable”....
The Change You Need Is the Change You Make. SaaStr AI Annual 2026 Will Help You Get There.
Here’s what I’ve learned after 13 years of building SaaStr, investing in 50+ leading B2B companies, and watching thousands of founders navigate moments of massive disruption: The founders who win aren’t the ones who figure it out alone. They’re...
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...
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