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Dear SaaStr: I Sold My Company And Made Real Money, But I Still Feel Like A Loser. What Should I Do?

SaaStr

David Sacks made tens of millions at PayPal but had to do more. And sometimes it almost never ends. Dave Duffield made $10 billion when Oracle took over Peoplesoft … but he still had to go and co-found Workday. So he founded Yammer and sold it for $1B+ cash. And he made millions as an angel investor. But he still wanted to go bigger.

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10 Must-Read Books for Startup Founders

Baremetrics

In The Hard Thing About Hard Things , Horowitz distills years of experience building companies into actionable lessons of leadership. The Hard Things About Hard Things by Ben Horowitz Ben Horowitz is a cofounder of Andreessen Horowitz and one of Silicon Valley’s most respected entrepreneurs and investors. Listen to it here!

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The SaaS Org Chart Live with David Sacks (Podcast #491 and Video)

SaaStr

David’s first foray into SaaS was in 1999 when he joined a startup that would become PayPal, starting as the product leader and later as the COO. Subscribe Please do not fill in this field. David Sacks: SaaS Background and Investments. Microsoft acquired Yammer for $1.2 billion in 2012.

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Maybe 80% of Public SaaS Companies Are in the SF Bay Area

SaaStr

You could remove Adobe and Paypal, and then it would be 70/30. You could add in Microsoft, Amazon and Google and it would plummet to 50/50. You could add in SAP and Oracle and it would go back up closer to 80/20. And more of the next-generation, from Canva on, is from outside the Bay Area. So what conclusions can we draw?

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The Double-Stretch Hire Rarely Works Out

SaaStr

Start with the Paypal-style of a “barrel” role. But after that, it’s tough. OK besides a blanket Don’t Ever Do Double Stretches Except in Year One, what’s another idea, SaaStr?

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Top 5 Things We Learned from BUILD in 2021

OpenView Labs

We know the route to leadership is less of a straightforward path and more of a rollercoaster. This theme of unconventional paths to leadership continued when Casey Renner spoke with Yvonne Wassenaar, CEO of Puppet for our BUILDing to Boss mini series. The path to CEO isn’t linear. That’s the key to scaling your user base.

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Applications for Reforge’s Spring 2022 Cohort are Now Open

Casey Accidental

Product: Product Leadership , Product Strategy , User Insights for Product Decisions , Product Management Foundations , Mastering Product Management , Data for Product Managers (new). Product Leadership. Harsh Sinha , CTO at Wise, formerly PayPal, Ebay. If you have any questions, please send them to hello@reforge.com.