Your life on a chalkboard

Our investor Jeff Bussgang asked several years ago if we’d be willing to do a case study on Mattermark for his entrepreneurship class at Harvard Business School. At the time, Mattermark was flying high and growing 100%+ year over year. The case was a snapshot in the time, asking students crucial questions about what direction the company should take: should it dig deeper into the VC customer base, or expand into the sales and marketing use case?

For the first time in the four years it has been taught, all three of us flew out together to Boston this week and fielded questions from students. It was the first time I had seen the case taught, and it was fascinating to watch students dive into something I had worked so thoroughly on. Watching five years of your life batted around a classroom and recorded on a chalkboard by a professor is a humbling experience.

At first, watching the case study method was jarring. How can you possibly compress so much complexity into a moment and a single binary decision! But talking to students after, they seem to have a firm grasp on the expanse of what they were evaluating, many of the ways you could look at it, and even the notion that you never get all the data at one moment to make a decision.

I left feeling like despite the bad rap that business schools get, the students I saw seem would have above average odds of success as startup founders. It was also great to spend time with our cofounder Andy, and be reminded how much creativity there is with all three of us in the room. Hopefully life is long enough that we all get to work together again.

From the Operators

We did not find a good operator post this week. Despite us following 1,000+ RSS feeds, the sad fact is founders don’t write often. If you know great founders that are writing, please send links our way.

From the Investors

It’s popular to say making work a big part of your life is neglectful and shortsighted. While lots of other things in life deserve attention, I believe it is in fact incredibly important to have a rewarding career. I thought Hunter Walk of Homebrew did a good job of capturing that in Would You Put Your Job On Your Tombstone?

A founder recently came to Joanne Wilson of Gotham Gal Ventures seeking advice on what to tell her board about her pregnancy. Instead of unveiling some complicated plan for her maternity leave, Wilson counseled, “just simply tell them you’re pregnant, this is your due date, how excited you are, and that’s it”. Guess what–that works fine! Wilson’s full post is worth a read: Diversity Should be #1 for Good Reason.

From the Analysts

Before Softbank was swashbuckling into deals with Door Dash, Uber, and Opendoor, there was Tiger Global. We hardly hear anything about Tiger these days, but just below the radar they continue to aggressively back some of the most promising startups. Savannah Dowling of Crunchbase pulls back the Wizard of Oz curtain in Prolific Tiger Global Management Maintains Strong Investment Posture.