A Walk in The Land of Never Was: Lessons That Led to Green-Lighting Our Most Popular Feature

There are so many reasons not to do a thing. Fear, laziness, lack of skill or resources, and stubbornness all come to mind. But this year, I found a reason more dangerous than all of them, worse because its lackluster sound gives it the camouflage of dullness among a deluge of new shiny things. The danger is in finding a great idea, but thinking it doesn’t matter and tossing it aside. “No, obviously we won’t do that,” is the catch phrase. Spoken with enough confidence, especially by someone powerful and…

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Checking In On My Fantasy VC Portfolio From February 2014

I’ve been doing some updates to the good ol’ blog, and noticed a fun post from 2.5 years ago highlighting my picks at the time. RelateIQ — I ended up investing in their Series C as a result of this post (their founder Steve Loughlin invested in Mattermark, and after 2 years at Salesforce he is now a partner at Accel Partners), and they were acquired by Salesforce 5 months later for $390 million. Instacart — They were my Y Combinator batch-mates, and I still use them for all my grocery…

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Request For Startup: Personal CRM for Grown-up Friendships

My life is really full, as a startup founder and CEO there are endless things to do. There are always more meetings I could take (maybe should take?) and by the time Friday evening rolls around I’m usually pretty happy to head home and curl up for the next two days on the couch with a book, a drink, and some good music. This is probably not new… but lately, the signals have been getting through. “It’s hard to support someone I never see.” “You’re really hard to get a…

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How to Network to Startup Investors

Tonight I hosted an impromptu AMA on Twitter, and I was surprised by how many people asked about how to network to startup investors. The question itself isn’t surprising, but when I responded with “get introductions via their current portfolio founders, or do some good old fashioned networking to get there” the reply was “on what platform?” Oh boy. Platforms have adverse selection. They say, “I am too lazy to actually network!” AngelList and LinkedIn have this problem, and when investors are looking for the top 1% you better believe…

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Monica for CEO

A fictional scene from the hours leading up to the emergency board meeting held by Raviga Capital that we weren’t allowed to see, during the HBO Silicon Valley finale. Season 3; Episode 1: “Monica for CEO” — with a new look and new found confidence, there are going to be leadership changes at Pied Piper. “But how can you do this to Richard? Especially after all he’s just been through!” Monica exploded, leaning back against the jagged brick and taking a long drag from her cigarette. “Monica, the choices you…

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What I’d Like to Stop Doing in 2015

I really do love New Years. Reflecting on life and setting goals to make it better definitely feels like a process worth celebrating, and since my professional life began 10 years ago I’ve really enjoyed spending some of my time off in December preparing for the year ahead. I’d layered in a lot of goals over the years like getting up early, prioritizing self-care (nails, hair, skin etc.), and writing a TON more. This year, I will continue on the journey for self control and my focus will be on…

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Burn Rates Post & Second Seed Announcement Enter My Top 10 All Time Blog Posts List

This year has been an interesting one for blogging, I’m writing a lot more drafts and publishing far fewer posts. I’ve adopted Medium as my main platform for what I’d consider to be my “professional” writing because the editing tools are superior to WordPress, and the writer’s experience being good leads me to draft more and feel excited to quickly jot down something and trust that the platform will help with distribution. I’ve been blogging lightly for my company but have handed off a lot of our professional brand voice…

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Tweetstorms, Hashtags, and Why User-Invented “Features” Keep Me Long on Twitter

Full Disclosure: I bought Twitter stock in the company’s IPO and I will not be selling it anytime soon. Each year around the holidays I head North to Washington State to hibernate for a few weeks with my parents at their house, reflect on what I’ve been doing with my life, read, gamble at the reservation casino, drink and snuggle by the fire. This past winter I decided, after a few glasses of wine, to drive my Twitter followers a little crazy. I had a lot of ideas I wanted…

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Introducing Mattermark, the Deal Intelligence Company

The year we suspended disbelief long enough to find a frighteningly ambitious startup idea. From “TechCrunch Killer” to “Bloomberg for Startups” and beyond… Part of my job as an early stage CEO is to protect my company from being put into a box too early. Leaving us unsorted makes investors, customers and even employees a bit uncomfortable. It’s human nature to categorize things, to crave the efficiency of communicating, “Mattermark is XYZ for ABC.” It feels safe and socially correct, intellectually digestible, rational. But those motivations aren’t what drive category defining…

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