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

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?

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 they don’t have fleshed out profiles on these platform a lot of time. And so what if they are there, they’re already picked over. Is this true? No. But it is how investors think.

If you are a founder who wants to get in touch with investors I would take two approaches, and do them simulatenously.

1. Just cold email / call them. I mean, why not? You’re going to have to sell something to someone, someday. Why not start here? And if you are seriously thinking the lack of contact information is the barrier you are one lazy motherfucker and should not be funded.

2. Network your way there. Draw a map on a piece of paper of each person you want to get to, and identify with your email, alumni network, friends and family, facebook, twitter, linkedin, etc. how to get to them. It might not be just 1 degree of separation. I have people several degrees away from me that I have been working on for 5 years. This is the game, and if you are a founder (and particularly CEOs) get ready to play. At each meeting, your goal is to sell why you should meet with the next person in the chain. Along the way, you need to be charming, interesting, add value for the person you are currently talking to, and maintain that relationship so that when you finally do get to the person who was your target your reputation is impeccable.

TRUTH: Fundraising is hard because 99% of people are not willing to do #2. This is how we got connected to Brad Feld, who lead our Series A. A warm introduction via Rand Fishkin of Moz. I had tried the cold angle on Brad and kept following up for 6 months until we finally got the warm connection. Remember, do #1 and #2 simultaneously.

DARE: Drink a whisky right now and email that investor you admire most and have up on some pedestal with the best one liner of your life. That’s what I did when we had just $150K left in the bank, and he came through.