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 respected who uses logic well, and that idea enters the Land of Never Was.

The Land of Never Was is the place where discarded ideas go to hang out. It’s the bottom of the backlog, the coldest corner of the icebox, the bottom right hand corner of the kanban board. It’s a mostly dull gray place; dusty, creased, redolent with the smell of crumpled and slowly disintegrating notebook pages and post-it notes that long ago lost their stick.

Around this time of year I like to take a vacation there, and walk along the shore of the Sea of Could Have Been with my little metal detector skimming the dunes for something shiny that I might have missed. Whenever I do this I keep my expectations low, so I’m not necessarily expecting to unearth any treasures, but it gives me an excuse to stare out at the horizon.

I’ve been working on my startup for nearly 5 years, and on startups overall for 10 years, so the sea has had a lot of time to break down and turn over the remnants. You’d think after all that time, walking the same stretch of beach, I’d find fewer and fewer items of interest, but it isn’t so. I keep finding new ways to circle back on old ideas, as my little detector beeps and I dig up some shiny scrap that I didn’t notice last time I wandered here.

“No, obviously we won’t do that.”

Self-help books are abuzz with find the life-changing magic of tidying up, saying ‘no’ more often, giving fewer fucks, and startup culture rewards being stubborn in a “Jobsian” ideal of the creative genius persona. For those of us who already drank all this Kool Aid and are tough stubborn self-directed intensely independent motherfuckers, I have a suggestion: take a walk on the shore of your own imagination, along your Sea of Could Have Been.

Find something you said “No” to that should have been a yes, and make it right.


It took us awhile to find this particular treasure, but we’re so happy that Mattermark now offers the ability to look up contact email addresses!

Also posted on Medium

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 shopping. This pick seems super obvious now, but at the time they had only raised their Series A when I picked them.
  • Uber — I picked them because they were an early Twilio customer and I was already spending way too much on the service. This one was probably already obvious, but they had only raised $300M of funding at this point (versus > $15 BILLION now) so my fantasy portfolio definitely benefits!
  • Hired — I picked them because I love the founders, and my company has been a customer from the beginning and the service just gets better and better. They announced their $15M Series A just 6 weeks after this pick.
  • Digital Ocean — I originally picked them in June 2013 because I knew their bootstrap story and how loved they are in the developer community. They would announce their Series A shortly after my February 2014 post as well.
  • Product Hunt — I picked them because they reminded me of Referly and Launchgram, and Ryan Hoover has the X factor. They didn’t have any funding when I made this pick, and would announce their Seed round later that year.
  • Magisto — I picked them because I had recently paid for their mobile app, which I very rarely do. The company hasn’t announced more funding since then but remain among the top 10 grossing apps in the photo and video category in iTunes.

Funding Summary

Collectively, the companies in this list have raised $15.2 Billion in funding since this call… but obviously this is totally skewed by Uber. Excluding Uber, the other companies went from $65 million of collective funding to $609 million, and only 1 of them did not raise a follow-on round.

This is of course a fantasy fund, and if I were really trying to get results things like winning the deal would have to be factored in. But it’s still fun to see how these things play out… and important to remember these were not nearly so obvious (at least to me, maybe VCs disagree) at the time.

It was fun making this list, and exciting to follow along as these companies have grown and evolved over the past 2+ years. I can’t wait to see what they each do next! I love angel investing, and happily these days I’m putting my money where my mouth is.

Looking forward to putting out another list soon!

 

 

 

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 hold of.”

These aren’t coming from business contacts, and they’re not coming to me by email. They’re coming from friends who I have to admit I don’t know when I last saw, and they are texts, Facebook messages, Twitter DMs. I saw friends 2 weekends ago who I met separately, knew as they met, courted, and got married and I was at the wedding… but that was 6 months ago! We are all shocked when we added up the time.

These are not casual acquaintances, theses are real friendships and the message is coming through loud and clear: invest here or you risk growing apart, losing touch.

Growing up I was one of those kids who wasn’t really part of any one clique, but had a friend or two in every single one. I was a serial monogamist when it came to best friends, usually those relationships would last a few years at a time and then we’d grow apart and move on. Now as a married career-focused woman, living in a major city, not planning to have kids I am realizing that my friendships are really important to my happiness in life. They are my chosen family, and the aloofness of how I’m acting doesn’t line up at all with how I actually feel.

Weird.

Over the years I’ve tried to solve this by building better habits, trying to bring my professional best practices to bear on my personal life. Off and on again I’ve had lists, Excel spreadsheets, even entered people into RelateIQ just so I could skim the list from time to time and make sure we were staying in touch. I always have this fantasy of sending Christmas cards, I even buy them!, and then it never happens because I don’t have the addresses. I’d say we host a party at our house every other month at most… it used to be every couple weeks. Frankly, Kevin and I aren’t even great about proactively scheduling dates — we usually just wing it and I’m pretty happy with that, until suddenly I’m like, “why haven’t we gone on a REAL DATE in 6 months?” and then I’m not happy with it til we do (I know you husbands out there are LOLing).

I need a CRM for my personal life, but not called a CRM obviously and much more tailored to stuff like birthdays, kids names, anniversaries, food preferences, and other stuff that matters but is just hard to remember. On top of that, I want to know when I last spoke with or hung out with a friend and I want to be reminded to do things like send flowers, write a quick congratulations email, invite them to a wine night or book night or boardgame night or whatever at my house.

I know this sounds super mercenary, but I bet it would work.

I think NextDoor could have been this, but won’t be because it’s too gossipy and impersonal. It isn’t Facebook. It isn’t anything I use today, because brand-wise I want it to be private. My Mom had this pretty blue book where she’d record all of this stuff about her friends and family. I remember they each got a page, and it was usually on the desk in our kitchen next to the phone. I want something like that, but for the modern age… preferably on my phone.

Who will build it?