Dear SaaStr: Is Burnout Especially Intense in Failed Entrepreneurs?
Dear SaaStr: Is Burnout Especially Intense in Failed Entrepreneurs? I see burn-out much more commonly in “fairly successful” entrepreneurs — not failed ones. And usually starting around Year 3. Building in Year 4. And then it hits >hard< in Year 5. First, it’s...
The Worst Part of Investing
So we’re at the time of the year where I experience the Worst Part of Investing, multiple times. What’s that, you might ask? Losing money? No. While not fun, it’s embedded into the business model of investing. It happens. A rough quarter or two at a key investment?...
When Times Are Tougher, Some Still Way Outperform
When times get a little tougher, There will be plenty of folks to tell you why it’s harder. Plenty. Just a few though will tell you and show you how to do actually do >better< Follow those leaders into the light — Jason ✨Be Kind✨ Lemkin (@jasonlk) October...
Customers Have Windows to Deploy New Apps. They May Buy Early — But Only Up to A Point.
We all want to push, push, push. To make the month and the quarter. And you have to. But there’s a lot of stuff you also need to hold back on to go long. Like not pushing too hard. Many enterprise customers have narrow windows during the year when they evaluate new...
Want to Be Paid More in Sales and Customer Success? Fine, But You Gotta Close More
Even with late stage VC capital much harder to get now, and the IPO markets still frozen, I see many folks on my LinkedIn feed saying Sales and Customer Success are underpaid. And that they, in particular, are underpaid. That they add so much value, they should be...
Your Customer Success Team Probably Really Are Just Gap Fillers
A lot of CS teams are just gap fillers A gap opens up when: – Sales abandons the customer the moment deal is closed– Support too reactive & slow to solve real issues– Deployment harder than should be An important gap to fill, and a full-time job...
The Confusing and Confounding Advice on Capital Efficiency
SCOOP: TikTok parent ByteDance's operating losses more than tripled last year to over $7 billion as it pushed for growth. Check out the company's full-year 2021 and Q1 2022 finances https://t.co/XneCChBjYm tip @Techmeme — Sal Rodriguez ???? (@sal19)...
Great Support Really Can Make Up For a Lot of Things
So I saw this tweet, and even a decade after our acquisition by Adobe, it sort of hurt: Currently evaluating #DocuSign vs #AdobeSign for clients. Started with DocuSign, finding a few things not that intuitive, but just had an amazing support chat experience....
Dear SaaStr: Why Do Most SaaS Startups Fail?
Dear SaaStr: Why Do Most SaaS Startups Fail? I’d like to suggest that web start-ups founded by quality teams often fail due to time. I know those hot start-ups seem to be lapping you,Growing faster,Raising bigger rounds You should worry But here’s the thing...
Seasoned VPs Cost 10x a Stretch VP Now. Is It Worth It?
Quote of the month https://t.co/b88fxMLM6A — Dave Kellogg (@Kellblog) October 2, 2022 So That VP That Has Done it Before always costs more than the stretch VP. They ask for more salary, and a bigger team. As they should. But in the past few years, the gap has...
Dear SaaStr: How Do I Do My Retention Negotiation in an Acquisition?
Dear SaaStr: How Do I Do My Retention Negotiation in an Acquisition? A few thoughts on retention compensation when you are acquired First, understand that the acquirer almost certainly already has a strong sense of what they want to do (right or wrong). Even if they...
The Challenge with SMB SaaS: High Growth Can Only Mask High Churn For Just So Long
So far, the only startups I’ve lost money investing in had one thing in common: they had high churn in the early days Some fought through it But a lot never do — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) November 22, 2022 So in theory, SMB SaaS is...
Dear SaaStr: What Are SaaS Companies Generally Worth When They Are Acquired?
Figma cost $20B because (x) It was 2x the last round price (y) it wasn't for sale Lots of deals end up getting priced like that in the end — Jason ✨Happy✨ Lemkin (@jasonlk) September 25, 2022 Dear SaaStr: What Are SaaS Companies Generally Worth When They Are...
Don’t Settle for Less Than 100% NRR from SMBs (Updated)
"How HubSpot fought its way out of low NRR in the early days" with @bhalligan + @dharmesh pic.twitter.com/frlKW6V6oW — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) June 3, 2025 As part of our 5 Interesting Learning series we’ve had a chance to do...
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