Dear SaaStr: Is it Bad to Leave a Struggling Startup?
Dear SaaStr: Is it Bad to Leave a Stuggling Startup? It can be a tough situation. And one more and more folks are in today. It’s toughest when you are in a critical role. Especially one with no redundancy, and no one else to take your place. If you’re a...
Wiz Had 4 Co-Founders. Databricks and Anthropic Have 7. Stop Overthinking It.
Google just closed its $32 billion acquisition of Wiz. It’s the largest cybersecurity acquisition ever, the largest Google acquisition ever, and one of the largest B2B acquisitions period. And Wiz has four co-founders. Not one. Not two. Four. Assaf Rappaport,...
Dear SaaStr: Is it Wisest to Approach One Investor at a Time?
Dear SaaStr: Is it Wisest to Approach One Investor at a Time? No. First, it takes too long. If a VC doesn’t know you, and you aren’t a “super hot” start-up, even if you do get a term sheet — it may take months. Yes, term sheets get done in one day. I haven’t done...
Dear SaaStr: My Investor Wants Weekly Meetings. Is This Too Much Time?
Dear SaaStr: I am a startup founder that writes extensive monthly report to investors. We are also doing weekly meetings, are they asking for too much of my time? Yes. Some rough rules: For every 1% of a company an investor owns, an investor should get one meeting a...
Dear SaaStr: How Do You Know When It’s Time to Leave Your Current Company and Move On?
Dear SaaStr: How Do You Know When It’s Time to Leave Your Current Company and Move On? There are a lot of valid reasons to leave your job for a potentially better one. But — if your job isn’t bad, and your boss is pretty good, it’s worth...
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...
Dear SaaStr: As a CEO, How Do You Know That Your New Employee is an A,B, or C Player?
Dear Saastr: As a CEO, How Do You Know That Your New Employee is an A,B, or C Player? You might not at first. So get help. But you’ll get better at this. As a first-time manager, you really won’t have the experience to know really who is an A, B or C player for any...
The 9 Qualities of a Great Sales Rep
Dear SaaStr: What qualities do the great salespeople have? When I'm ready to buy, A great sales rep makes it easier. And better. And gets all my questions answered. A mediocre rep just makes it harder. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) April 2, 2022 A...
Dear SaaStr: At What ACV Can We Afford a Sales Team?
Dear SaaStr: At What ACV Can We Afford a Sales Team? The short answer hasn’t changed much: it’s still tough to afford a human sales team below $299 a month / $3k a year ACV. At least in the U.S. and Western Europe. The math just doesn’t bend enough....
Dear SaaStr: What Are The Biggest Lessons You’ve Learned from Failure as an Entrepreneur?
Dear SaaStr: What Are The Biggest Lessons You’ve Learned from Failure as an Entrepreneur? Don’t Fail. I’ve almost failed several times. Really almost every time. But never actually failed. Why not? Never quit. You can’t fail if you don’t quit. Find...
PE Is No Longer Coming to the Rescue. And That Probably Means No One Will.
M&A hit record highs last year. But like so many things in the AI Age, the benefits were not evenly distributed. For Plain Vanilla SaaS? PE has checked out. There’s a tough topic that it’s time to be honest about in 2026: PE is no longer coming to the...
Dear SaaStr: Can A SaaS Startup Really Scale With 2 Co-CEOs?
Dear SaaStr: Can A SaaS Startup Really Scale With 2 Co-CEOs? Many will tell you it’s a bad idea, and it probably is — in most cases. I sort of tried this myself, and it didn’t quite work. We had all the classic problems of unclear authority, especially...
Dear SaaStr: How Many Of Our Prospects and Customers Should I Meet Face-to-Face?
Dear SaaStr: Should an early- stage B2B startup meet every customer face-to-face to receive feedback? If you could — all of them. The more customers you meet in person, the more that buy from you, and the more “more stuff” they buy from you after,. The full data here...
The Trade Desk Was Priced for Perfection. Then Growth Slowed. Now It’s the Worst Performing Stock in the S&P 500.
The Trade Desk was the darling of adtech. A profitable, founder-led adtech software company that grew at epic rates year after year, built the leading independent demand-side platform, and positioned itself as the Switzerland of programmatic advertising. And then it...
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