We are excited to announce our investment in DEN, a platform that makes it easy and affordable to build a beautiful home from the ground up. A few months ago, we shared our views on the housing market. The United States is in the midst of a housing crisis. It…

I sent this e-mail to our founders on May 16, 2022 in light of public market volatility and the corresponding VC twitter prognosticating. By popular request, I’m sharing more broadly in hopes it may prove helpful to others navigating these same waters. Gutter Capital Founders, ​​There is a lot of…

Uber has written millions of lines of code, but none of it changes the reality that drivers need to feed their family and pay their rent — In 1938 Franklin Delano Roosevelt warned America, “do not let any calamity-howling executive with an income of $1,000 a day,… tell you… that a wage of $11 a week is going to have a disastrous effect on all American industry.” The following day he signed the Fair Labor Standards Act…

So you’ve raised your first round of financing, hired some key team members and are off to the races. Your new investors are aligned on your vision and the goals that you will need to achieve in the next 12–18 months. …

On September 11, 2001 I was in the seventh grade. I was home sick from school that day. …

I am sitting in Esme, on the northern end of Greenpoint, just before the Newtown Creek. It is empty. There usually isn’t a sign-in sheet with a thermometer at the door, but today there is. I am clocked in at a cool 97.8 degrees. I played a very small role…

Dear Team, I hope this message finds you well. I am sure you are all still processing the news of last week, and I am sure that like me, you will be for some time. There isn’t much I can say about the deal itself, which I know will be…

Note: I wasn’t planning on writing a blog post today. I was planning on getting some stuff done and getting on a flight. …

Hang around our offices long enough and you’ll hear someone say “cleaning is a spiritual act.” You’ll try to figure out if they’re kidding, but you will likely give up. If you press them hard enough they might admit that they were mopping floors until 4am and they are running…