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Dear Founder, Selecting a co-founder is one of the most pivotal decisions you’ve made to date. You went in hoping for a decades-long partnership. You’ve admired what the legendary co-founders—Bill...

Dear Founder, Well, it appears that you must be having some success in your company. Your team has evolved from a group that was very cohesive and aligned every day, to...

Dear Founder, You’ve decided to sell your company. Hopefully it’s because some buyer is aggressively seeking you out. Your suitor thinks you’re great and is offering a huge premium to...

Dear Founder, I am very sad that you find yourself in this situation. Most people truly do not like to inflict pain and discomfort on someone else, which is what happens...

Dear Founder, Congratulations! Today is a big day! You and your board have decided to take a buyer’s offer for your company. Hopefully, you were able to make your employees, your...

Dear Founder, I’m sure you’re somewhere between being pissed off that you are being deserted, and worried about what you’re going to do to make up for this person’s contributions....

Dear Founder, Congratulations! If you’re expecting to go public, it means that you’ve built a successful, predictable business—it’s nearly impossible to achieve this. By this time, you probably have tons...

Dear Founder, Well, if you’ve opened this letter, things are not going well. I’m sorry that things are off-kilter; it’s never easy. We back brilliant founders all the time, and...

Dear Founder, If you’re reading this, you’re probably struggling with your business strategy or execution. At the risk of stating the obvious, two points to consider: If things are really...

Still not sure whether you might be a tweener? These are things we sometimes hear in updates that set off our radar: “We’re working on our churn problem.” “We’re now...