New @ThePeelPod with Dan Teran at Gutter Capital
Fresh off of selling Managed By Q to WeWork, Dan and friend @chess_is_ok started Gutter Capital during the depths of COVID.
It has evolved into one of the scrappiest early stage funds in NYC, culminating in Elbow Grease, a hands-on accelerator based in the heart of the city.
They just raised another $75 million to run their second cohort and put 15 teams in one building on Canal Street and help hire their first employees. (They’ve hired over 100 people for companies in their first two funds!)
We talk about why the best founders want help, how portfolio concentration makes investors more hands-on, selling Managed by Q to WeWork, going big-wave surfing with Adam Neumann and Laird Hamilton to close the deal, how raising a fund was harder than selling a company, and why he thinks startups should form a board and use OKR’s from day one.
Thanks to @numeral, @FlexSuperApp, @Amplitude_HQ, and @merge_api for supporting this episode!
Timestamps: 0:00 Elbow Grease: NYC’s scrappiest accelerator 7:39 Building a small, hands-on, in-person experience 13:39 Recruiting 100 people into portfolio companies 16:25 Portfolio concentration makes investors more helpful 24:58 Why raising Fund 1 was so hard 28:08 Advice for new fund managers 30:30 “Hiring today is as competitive as ever” 32:23 Selling Managed By Q to WeWork 35:23 “Never raise too much money” 39:43 Almost buying his company back from WeWork in Feb 2020 43:50 Starting Gutter Capital in the depths of COVID 49:34 Funding angel investing with gambling proceeds 52:39 Behind the name “Gutter Capital” 54:49 “Raising a fund is like getting punched in the face” 59:03 Writing long LP letters 1:06:45 Investing in real world problems 1:09:48 What a Gutter founder looks like 1:12:46 How Gutter makes new investments 1:18:41 Importance of customer calls at pre-seed 1:21:59 Evolution of NYC tech over last 15 years 1:26:15 Why you should form a board at Seed 1:28:29 How to run a Seed stage board meeting 1:34:04 Sharing carry with portfolio founders 1:35:56 The best founders need lots of help 1:39:30 Big wave surfing with Adam Neumann and Laird Hamilton



