He Sold His Startup for $130 Million, Here’s What He Learned, and Questions to Ask When Considering Whether a New Job is a ‘Fit’ for You, Plus Other Great Reads [link blog]

More stuff for you to enjoy….

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What I Learned Selling My Company [Harry Glaser/then: Periscope Data, now: Modelbit] – Harry sold Periscope Data for $130m and is back building again with Modelbit, an ML engineering platform. Here he provides actionable advice for founders who are building long-lasting companies but know M&A might be the eventual, and successful, outcome.

This is about the bread-and-butter, $50M-$500M acquisitions of mid/late-stage startups who probably took the offers because they had serious doubts about whether they could go the distance. 

The enterprise version of the great re-bundling & vendor consolidation trends [Pat Kinsel/Proof] – Entrepreneur Pat Kinsel noting that many B2B software/tools are at risk of being displaced in their customer relationships by ‘good enough’ versions provided by another existing vendor. Why? Not just the cost savings potential of bundling but also…

risk and InfoSec are still HUGE drivers for vendor consolidation. We are seeing this everywhere. Sophisticated customers want less risk and using fewer vendors is a way to achieve this. Not only for its direct sake, but because each vendor relies on their own set of vendors so it is a geometric problem for the enterprise buyer. And let’s face it, startups don’t always pick the best vendors. We’re seeing this articulated by customers as “4th party risk,” which they very much want to control.

Fit [Molly Graham/Google, Facebook, Quip] – Molly passes along advice for assessing when friction (or even failure) in a job role isn’t about your skill and functional expertise but about more nebulous ‘fit.’ Some of her framework is about how to understand in advance of taking a position, whether the ‘fit’ circumstances are right

Often when we’re searching for a job or being recruited for a job, we’re too focused on the company side — Do they want me? Can I pretzel myself into the space they’ve created for this role? 

But the most important questions are where the two sides come together, particularly as you get more senior. Here are three questions I often ask when I or one of my friends are considering a role: 

1) Are they hiring YOU? 

2) Is what they want what you are great at?

3) Does what they need match up with what you want to do?

When it might actually be a good idea to ask to be ‘layered’ under a new manager [Camilo Fonseca/Business Insider] – From an interview that Lenny Rachitsky did with Noam Lovinsky [YouTube, Thumbtack, Grammarly], Insider excerpted a piece of advice that goes against a conventional wisdom of career advancement.

How to Build a Better Motivational Speaker [Tad Friend/New Yorker] – Where do we start? Read this if you’re curious about the economics of the high end self-improvement industry. Read this if you’re trying to understand what the customers of these personalities are hoping to achieve. Read this if you want to know how Jesse Itzler went from white college rapper to Marquis Jet cofounder to this guy:

His home is an incubator for optimization. Itzler recently told an audience, “I said to my brother about my son, ‘He’s a good swimmer, but he doesn’t really have that eye of the tiger,’ and my brother said, ‘That’s O.K., as long as he’s happy.’ ” There were murmurs of approval. “And I’m, like, ‘No! He’d be happy playing Fortnite and eating Häagen-Dazs every night. We want him to live up to his potential.’ ”

Oh and by the way, he’s married to Sarah Blakely of Spanx fame.