“This Storm Is You” and Other Thoughts After a Year in M&A Limbo

I spent the last 9 months working on selling my previous startup, Mattermark, and now it’s finally done. This blog is more than 10 years old, and I’ve been blogging for nearly 20 years now… so the break from writing and sharing my life has been strange, but good. Now I’m ready to get back to it, and I find myself transformed by life (this is always happening, but it’s often so gradual you don’t notice it) and having a hard time recognizing my old voice, my old “face” in…

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Checking On Predictions & Fantasy VC Portfolios

On June 8th, 2017 I made a list of 20 companies that looked ripe for Series A… it has been nearly 4 months and I just checked to see how my predictions are going. 1 out of the 20 has announced their Series A so far: ClearMetal announced a $9M Series A from Innovation Endeavors and Prelude Ventures. I love to publish picks and then see what happens, and back in February 2014 I shared my fantasy VC portfolio of 7 companies, and then updated it in February 2015 showing a nearly 9.1x* increase in…

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What Does It Feel Like to Be Married Cofounders?

when my light’s burn out you’re the only one, you’re the only one you’re the only one left I will answer to when my lights burn out you’re the only one, you’re the only one you’re the only one here who can switch out the dud honey you’re a patient man living in the moment everything I am is not everything you wanted but here we are side-by-side in bed every single morning I am old you can’t keep my pace and you can’t see the flash beneath my veins…

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20 Bay Area Startups Ripe for a Series A Investment

It’s been a couple years since we shifted our product development focus at Mattermark to supporting sales and marketing deal sourcing, but that doesn’t mean I’ve lost my love for speculating on which startups are most likely to raise funding next. Living in San Francisco these past 8 years, I’ve noticed there are often companies that appear seemingly out of the blue and then raise a boatload of money. This was part of what inspired me to start Mattermark in the first place. Can we detect these companies earlier if…

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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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