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Dear Founder, There are bad days and then there are horrible days. This counts as a horrible day. A difficult experience with one of the great entrepreneurs in our portfolio...

Dear Founder, While it can be disheartening (and frustrating) to feel like you’re not making progress with fundraising, you should know that many WIN companies have been in a similar...

Dear Founder, Really? Why do you want to do this? I hope it’s not because it’s the cool thing to do... it’s easy to become an entrepreneur, but it’s way...

Do I even need a co-founder? Perfectly paired co-founders are as legendary as Hollywood power couples and beloved band mates. The conventional playbook says that you receive more by working...

Dear Founder, Congratulations! You are officially a real company. Well, you already were a real company, but now you’ve raised outside money—and you’ll likely have to have to put together a...

Dear Founder, If you’re reading this letter, you must be wondering whether philanthropy has a place in a startup. I have a very strong opinion about this: YES. We’ve all...