Picking up where you left off

This week our friend Andy Sparks is visiting us here in Colorado. Danielle and I cofounded Mattermark with Andy back in 2013. Since Andy moved on in late 2016, we don’t get to see nearly enough of him, especially now that we’re in different cities. It’s been amazing to reconnect this week. There are certain friends you meet in life where you can be apart for a long time, but within minutes snap back to deep conversation.

One of our favorite traditions while working on Mattermark was getting together for dinners at least once each week. Founder Dinners were sometimes an outlet for tough problems to solve at the company, but more often a forum for philosophical questions, talking about the sci-fi we were each reading, and DJ’ing each others’ favorite YouTube videos. Every night this week seems to be like a Founder Dinner, and it’s such a treat.

Andy is busy running his company Holloway, but we will never forget what a joy it was to work with him every day for 4 years. If I could wish anything for all our readers in 2019, it’s that you’ll meet at least one friend this year, who even after being apart for years, you could pick up right where you left off deep in conversation.

From the Operators

Avni Patel Thompson of Poppy is Learning how to say goodbye: grieving the end of a startup. So many of these emotions ring true to where we were with selling Mattermark a year ago, and Thompson is right that too few people talk about this part of startups.

Chris Herd of Nexves offers a surprisingly elegant distillation in Want to Be a Billionaire? Solve “I want X but Y”. It reminds us a lot of Paul Graham’s classic How to Get Startup Ideas.

From the Investors

Fred Wilson of Union Square Ventures has been a blogging tear this week. Investors should give careful thought to his post Missing The Forest Through The Trees. And he also has thoughtful comments on how startup outsiders view seemingly foolhardy startups in The Profit Motive.

Semil Shah of Haystack is in a thoughtful mood as New Years rolls around, and has two great posts this week as well. “Your Portfolio Is Your Path” is a rare look at some regrets from an earlier fund. And Risk And Reward is a caution to founders that aren’t willing to quit their job and leap into their startup before it is funded.

Tim Ferriss of has a very simple plan for Conducting a ‘Past Year Review’. If you want something more involved, Steve Schlafman has a detailed review system..

Martin Casado of Andreessen Horowitz gives a shout out to the great book Crossing the Chasm in his post: The Unending Chasm, and How to Survive It. I know the feeling of “if we just get this feature done, everything is going to turn around” or “we’ve got product market fit, it’s just scaling from here.” Sometimes it isn’t so easy.

Steve Schlafman of Primary Venture Partners boils down a key takeaway from Keith Rabois’s startup school lecture. This decision matrix reminds me of Ken Blanchard’s extremely useful situational leadership–an oldie known by too few startup founders.

If you know friends who’s resolution is to build a startup in 2019, Charlie O’Donnell of Brooklyn Bridge Ventures gives sound advice that first time founders should take to heart. Our favorite: get out of your house and talk to your customers!

Andrew Chen of Andreessen Horowitz has to be one of the more prolific writers and thinkers in startups, and he’s published his 2018 essay collection on growth metrics, marketplaces, viral growth in the enterprise, and more (PDF included).

Hunter Walk of Homebrew adds more thoughts on portfolio construction this week in 3.5 Notes From Our Most Substantial Venture Exit So Far.

Tomasz Tunguz of Redpoint Ventures checks in on Just Where Are SaaS Companies Priced After the 2018 Correction? We know this eventually trickles into startup valuations, and it will be interesting to see where this goes in 2019.