“Am I doing a good job?”

“Am I doing everything I should be doing?”

I ask my cofounders these questions from time to time.They say yes and give me a hug, and my ego is placated. But later on I still wonder am I really doing a good job? Am I leveraging every moment of time the way I should?

There are a lot of articles telling us what we should do to be good, often formulated to demonstrate how to be more like whoever the hero CEO is.Wake up early. Time block your calendar. Raise now. Get that big valuation so it will be easier to recruit. Everywhere I turn on Medium someone has advice for what I should do, and I tell myself to listen because I want to be open to feedback and I want to learn. But sometimes when I am able to quiet that story down, I catch myself listening because it is just so much easier to have someone else figure out what I should do.

“I’m tired. Could you bargain with fate for me please? Thanks.”

As we head into a more difficult funding climate, I expect there will be a lot of founders saying, â€œbut I did everything I should have done… why can’t I raise a round? It’s unfair.” Where did that should came from? How can you justify your sense of justice getting riled up with “it’s unfair” when you didn’t even do the dirty work of picking the should yourself?

Shortcuts I Took

Sometimes I needed an answer right now, and seemed like a good idea to short-circuit the hard work of sitting still and figuring out what actually works with the most recent piece of startup productivity porn. It was a quick way to alleviate my angst, it was a self-centered solution that was more about resolving my own cognitive dissonance than getting it right.

In a hurry I’d implement someone else’s should unexamined, but all borrowing shoulds second-hand got me was second rate results. The worst part was that among the ideas thrown at me, I didn’t consider most of the really crazy ones… I stuck with the plausible shit, without considering the source. Re-arranging my calendar when I could have hired 20 sales reps.Might as well be re-arranging the fucking deck chairs on the Titanic.

So about half-way into the year I said fuck it. FUCK. IT. I’m gonna do crazy shit. I’m sick of being plausible and how the hell did I get this way anyway.Real self over in the corner flagged down ideal self and said, â€œhey remember me, I’m the college dropout who took a ton of personal and professional risk to have the life we always wanted? Frankly, you’re letting me down lately.”

Waking Up

It’s harder to explain this part, and I suppose this is normally where you’d find a step-by-step walkthrough of what I did to change my approach. It would actually be a list of shoulds for you, but thinly veiled as my own story.

I sat still. I let my inner voice be louder and more trusted than the outside voices. I hung out with myself, wrote and read and drank wine and lit candles and looked at the view and stayed still thinking and stayed in as friends joked I was “getting old” and I didn’t care anymore because fuck you I’m 30. I didn’t assume the answers were anywhere else. I read my old diaries and imagined I was 15. I read books I loved in school and imagined I was 9. I remembered my life so far, and I wrote down things I’ve already learned from it and I didn’t publish them for anyone else to read. I made things just for me, like paintings and really good food.

None of these activities would necessarily have meaning for another person but I knew they were what I needed. I remembered myself, I apologized to myself, I forgave myself, and gave her permission to let go of should.

I bowed.

Bowing In

Writing this down this morning, I remembered at Founder Bootcamp they would bring us all back together with the pretty sound of the Buddhist singing bowl. Jerry invited us to bow in, and I remember the first time we did I looked around the circle like, â€œOh geez, what crazy hippy shit did I sign us up for?” But I did it anyway and got past the awkwardness, and as we did it over and over again for days it started to take on more meaning, and naturally I got curious about this ritual. There is a great essay from Sojun Mel Weitsman at the Berkeley Zen Center that does a good job explaining it. I pulled the relevant quote but if you have time I highly recommend reading the whole thing:

How do you bow to yourself? You can’t see your own eyes, you can’t see your own nose, we don’t see our own face. It’s pretty hard to bow in this direction [toward ourselves], we’re always bowing in that direction [away from ourselves]. If you bow in that direction, you meet yourself. So who is this self? That question begs the other. If I bow to myself, then who is this “myself” that I’m bowing to? Therein is the fundamental koan, who is myself, and how do I bow to myself?

You don’t have to be a Buddhist to appreciate this idea of bowing as a ritual, both to yourself for introspection and also as an offering to others. It’s just a simple acknowledgement. Actually, I’m learning you can bow to anything.

I wasn’t planning to put this essay into this post, it just kind of came to mind as I was writing and now I’ve re-read it and there is another part that is also very relevant to “the tyranny of should”:

If you think about all the things that you promised yourself you would do and didn’t do, and look back on that, you’d be amazed at all the intentions you had that you didn’t honor. Sometimes this holds us back. So that’s why we have such a thing as the Bodhisattva Ceremony. We avow all of our ancient karma and unrealized intentions, and renew and honor our intention to continue. This is one of the most important factors of practice, that you have an intention, and honor it. Everything else flows from there. Enlightenment, peace, it’s all there in our intention. We also fall off, but when we fall off, we come back. As a matter-of-fact, we’re always getting sidetracked. That’s the nature of our life: to have this intention, get sidetracked, and come back. One of the obstacles is, “Now that I’ve fallen off, I can’t come back.” Or, “I’ve been bad.” So the nature of practice is to make the effort, that no matter what happens, to keep renewing or returning to our intention.

With these thoughts, I’m bowing in to 2016 and renewing my intention.

---

“Wait, I just read this entire post and you still haven’t come to the point… Intention to what? What are you going to do?” you ask. â€œWhat should I do?”

I don’t have an answer for you, I can only smile.

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?

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.

 

 

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 are making don’t make sense to me. I propose we go inside and my assistant will get you a bottle of VOSS, and we can talk this through rationally,” sighed Laurie, as she internally categorized and ranked the damage she was doing to her home life and personal sanity by having a conversation like this in such an ugly setting, so late at night.

Grinding out the half-finished Davidoff under the heel of her flats, Monica ducked her head deferentially and headed inside. As she entered the office again she stopped suddenly, so suddenly that Laurie collided into her back. “Monica!” she gasped.

“I know what we need to do to make this work,” the associate turned to her boss, eyes determined and a bit glassy with ambition. “I’ll take over as interim CEO and make sure we don’t lose the team. They trust me, and Richard trusts me… we can get through this.”

The two women stood for a moment in the silence of the empty office, looking at each other without really seeing. Another minute, Laurie mused, and she would have broken the agreement she made with Peter for the first time in 10 years. Well it was too late now she thought, looking her young rival up and down with a mix of disdain and admiration.

“Okay. We’ll try it for a period of 90 days, during which I will actively recruit a permanent replacement for Richard Hendricks. His leadership is veritably non-existant and I simply can not tolerate his presence, so please keep him out of my sight during the transition.”

Monica held her tongue, it would be easier to just let things lie for now until she could sneak back into Erlich’s house and do some damage control.

“Thanks Mom.”

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 stripping away things that aren’t working for me anymore. I’ve chosen three things I will do a lot less of in 2015.

 

Public Speaking — unless it is in panel or Q&A format. It stresses me out, I don’t think I’m really good at it, and I feel guilty about the amount of time it takes to prepare and write a talk (which usually means I just don’t do it, which brings the stress).

Drinking Alcohol — it’s pretty amazing that I’ve gained 40 pounds since I started running my own company 3 years ago. It’s time to turn this around, and the first thing that has to go is alcohol. Drinking socially, or to cope with stress (e.g. “I need a glass of wine to wind down”) has to be replaced with walks, yoga, reading etc. if I want to get back my normal weight.

Traveling for Business — messing up my sleep schedule for business travel is the biggest productivity and health killer in my life, and often I find that the trips I book aren’t nearly valuable enough to justify it. In 2015 I will spend a lot of time in New York and Boulder, but when I do travel I will go for 1+ week at a time whenever possible, stay in an apartment with a real bed so I can feel like I actually live there, and make sure to set aside some time to actual walk around and enjoy the place I’m visiting.

 

Obviously my work won’t make it possible for me to completely stop public speaking or business travel, but any activity along those lines will be highly intentional and I will prioritize long term health and happiness over the short-term sparkle of opportunity. I am also hiring people on my team who can share these burdens with me, who will enjoy them and use them to build their own careers.

My online persona makes it sound like I don’t have much of a personal life, and that’s not exactly true — I just am pickier about the personal things I share as my inner life has become more developed. I look forward to sharing the New Year with my husband Kevin, my family and closest friends. In 2015 I’m sure I will travel somewhere warm and exotic, cook tons of amazing food, read a bunch of historical fiction and science fiction novels, finally furnish my roof deck and garden, celebrate as two of my favorite couples tie the knot, find a good reason to pop the bottle of Dom Perignon I’ve been saving, purge even more of my clothes and other clutter, and invent new things I haven’t even thought of yet.

Becoming a better CEO, learning how to work with my new board of directors, adding 50 people to the Mattermark team, continuing on my quest for a sustainable business model for high quality data journalism (I always wanted to be a writer, it just never seemed to pay very well)… these are adventures I’m already in the middle of and they’ll consume most of my creative output in 2015.

For the first time in 3 years I won’t be focused on fundraising! It’s to fully explain how wonderful that is, as my cofounder Andy puts, “for the first time in many years I’m working for a company where I’m confident it can’t go out of business this year”. A-fucking-men to that.

So cheers to 2014, a wonderful year, and onward!

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 to the talented Nick Frost, and he is hard at work building our community through blogging, email and social channels.

My Top 10 All Time Blog Posts

1. Is My Startup Burn Rate Normal?
2. Zombie Startups
3. Why I Won’t Be Using Betapunch for User Testing
4. Solve the Problems Your Parents Have
5. The $3B Exit Tumblr Could Have Had
6. Mattermark Has Raised $2M in Our Second Seed Round
7. I Don’t Do That Job Anymore
8. Don’t Waste a Single Moment
9. Zombie VCs
10. The Y Combinator Index

I don’t write with traffic in mind, but I do care about the reach of posts because it helps me understand what matters to my readership and what doesn’t. If I hit a nerve, I can quickly get above 10,000 visitors but for many posts a few thousands visitors is about right. There are things I want to quickly record or comment on. What I have been happy with these past two years is that the pieces I spent the most time on, and were the longest, actually did the best. I hope this means that I am learning to forge a stronger connection between my readers and my personal interests.

I write because it makes me feel more human to share my experiences and get feedback. Not all that feedback is friendly, and I’m not always right, but I always gain new perspective and learn from the community. This is my little corner of the Internet, and the people worldwide who have read, shared, commented, submitted to Hacker News, discussed and digested my writing has now crossed 1 Million people. I’m proud of that, and I look forward to writing for myself and millions more for many years to come.

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 to share, 140 characters weren’t enough to express what I wanted to say and I was too lazy to blog.

Soon, Marc Andreessen and I crossed paths (he had just gotten active on Twitter)… and he started tweetstorming too!

Are @pmarca tweets real? I can not be the only one wondering if it is a bot, or at least a ghostwriter

— Danielle Morrill (@DanielleMorrill) January 1, 2014

@DanielleMorrill @cdixon Apparently my challenge is to pass the Turing Test myself :-).

— Marc Andreessen (@pmarca) January 1, 2014

I got some positive feedback, and kept going:

@hnshah @DanielleMorrill that was quite good – wish more people would do this, just via tweets.

— Semil (@semil) January 2, 2014

There were questions of ettiquette for kicking off a new tweetstorm:

Do I have to announce this is a tweetstorm or are you all used to it by now?

— Danielle Morrill (@DanielleMorrill) February 4, 2014

And some tweetstorms inspired response storms, which was really cool:

(This tweetstorm format inspired by @DanielleMorrill.)

— ZacharyCohn (@ZacharyCohn) February 10, 2014

Inspired by @DanielleMorrill #ifiwasaVC tweetstorm, i jotted down some thoughts on the role reversal: #ifiwereafounder

— Chip Hazard (@chazard) March 30, 2014

Other cool things happened, including talking to the Twitter team about their timelines feature (something you can only use through the API right now)…

And other things… mostly just new friendships started and great conversations…

It even resulted in an offer to turn one tweetstorm into a book (TBD)!

I am pretty sure I did *not* invent tweetstorming (it actually has a different meaning, primarily used by activists in the past to harass brands online) but the tweetstorm — much like the hashtag, which was created by my friend Chris — is why Twitter is awesome.

On Twitter, users figure out the features and the interface for their conversations.

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 innovation, and making decisions for the sake of ease is always a big red flag to me.

Don’t get me wrong, there will be a time for having an extremely clear vision that we can lock in on, market against, hire against, build against. In fact, I think we might be very close to that moment of clarity. But before we go there, I’d like to share the journey of the past year after announcing the shutdown of our previous startup about a year ago on March 10, 2013.

---

Prologue

In March of 2013 my previous startup Referly was down to just 3 of us, after reaching a peak company size of 10 people. With $350K left of the $1 Million raised during Y Combinator, we had enough money to get another project off the ground. Kevin, Andy and I cut our salaries to nothing and headed to my parent’s house in Washington State for a couple weeks. We committed to nursing our pride, reading books, drinking wine, cooking, reconnecting as friends and thinking about to do next outside the fishbowl of Silicon Valley.

I was still a little pissed off at Paul Graham, who months earlier had said:

“You’re just too plausible. It’s as if someone was writing a sitcom about startups and you needed a believable idea.”

Every time I reflected on this conversation I would get pissed off all over again, but in a state of defeat it seemed reasonable to ask myself the previously forbidden question, “what if PG was right?”

If PG is right, I reasoned, then I need to stop doing such plausible things.

Moving to Seattle — We could have stopped here.

Before Mattermark, There Was Cursive

“Mattermark Wasn’t a Pivot”, but before there was Mattermark we almost did pivot the existing technology of Referly into a different idea, which we code named Cursive. It was clear the posts I’d been doing about startups were the biggest drivers of traffic for Referly, and we had a beautiful custom CMS. Medium and Svbtle were still much earlier in their growth curves, and appeared to validate the model so I thought maybe I would start blogging prolifically on my own platform and then invite others to join me, like a community-written TechCrunch.

I shared this with PG during office hours and he said something like:

“If you’re shutting down Referly why not start over with something completely different? If you want to kill TechCrunch then do that.”

Having some direction was exciting, but I also felt the foreboding sense that running a media company had the potential to be a soul sucking grind, with little software innovation and even less margin as a business. I’d have to really love the day-to-day to make it my startup. To test the waters I went on a mission to publish at least one post every day, for 30 days. 3 that stick out in my memory:

1. On April 3rd I ranked the growth of Andreessen Horowitz’s portfolio companies and Marc Andreessen emailed me along with several General Partners, saying: Thanks Danielle! We should do this ourselves :-).
2. On April 5th I published “Zombie VCs” using Crunchbase data to generate a list of firms who appeared to be inactive. This post electricified the VC industry and business media for a full week, intriguing and infuriating investors while revealing the lack of publicly available data. Awash in corrections and new relationships after hundreds of calls and emails, we’d found something important.
3. A scoop on Tumblr’s revenue shortly before the Yahoo acquisition earned a link from Kara Swisher, outreach from someone at the WSJ about a potential job, and a meeting with Michael Arrington. I’ll never forget, Michael sat down looking very grumpy and read the entire 1,200 word piece in silence before looking up to proclaim, “you can write”. I just laughed out loud, my blogger hero just said I could write! Holy shit.

At first I imagined building a “TechCrunch-killer” media business. I imagined a future where I would write about under-appreciated startups, analyze deals, and report on the dynamics of Silicon Valley and other startup ecosystems worldwide. I estimated TechCrunch made ~$20M in revenue a year, and that the bulk of this came from events. Much like the early days of Twilio, I rationalized the small market by telling myself the writing would initially appeal to hobbyists but that we could build a broader appeal from there, and learn as we went. We’d find a bigger market somewhere.

Building a tech startup oriented media company was a much narrower vision than Referly (my previous startup), where I felt we never settled on a single crisp sentence to describe ourselves. After more than a month adrift the clarity of focus in our new direction was appealing and 90 posts later my personal blog was squarely in Alexa’s top 10,000 websites, comments and emails of appreciation had started coming in, and we were even getting tips and sources for more original reporting.

We could have stopped there.

Fun lifestyle business, but what about building a software scale company?

---

The Research Lab

Byproducts of work are a gold mine. In the process of writing articles I created hundreds of spreadsheets to research markets, compare companies, and come up with unique angles. I published raw spreadsheets in many of my posts, and received a lot of requests to download them. As programmers, we were inspired by things we had heard about BuzzFeed’s assignment desk technology. We don’t know exactly how it worked, but the idea that they had built tools and processes to detect the most buzzworthy topics at any given time across the web was fascinating. We imagined we might do the same thing, but with a focus narrowed in on tech companies.

To do this, we knew we need to detect buzz about companies and spreadsheets weren’t going be enough. We compiled all our spreadsheets into a database, wired it up to a super-simple javascript table plugin and showed it to our investors. Not everyone got why this was so powerful, but for the handful of people who did the excitement was palpable, “can we use this right now?” they asked. We didn’t even have a login system, it was just an HTACCESS username and password on the project we called Cursive.

They told us about the money they spent commissioning custom research from GLG consultations, 451 Research Group and other expensive resources. They showed us their own spreadsheets and internal apps. They asked us if we’d consider coming on board full time to build an internal research team and make investments based on our data and methodology.

We could have stopped there.

If this data is so valuable, and you really have a unique angle, why aren’t you investing with it?

---

The Venture Capital Firm

Once it was clear we would add significant value and differentiation to someone else’s VC firm, the logical next step was to consider starting one ourselves. Could we raise 10, 20 or even 50 Million to test out various data-driven approaches to investing in startups? We spoke with several established investment professionals who could have come on board to help us run the thing, and it seemed promising. But we knew if we decided to run a fund we would not be able to be objective, share all our data and views as openly, or remain a trusted source charging people for our research.

I knew if I became a VC I wouldn’t be satisfied with small checks and a small role in the lives of my investments. I’d want to lead deals and dedicate the next 10+ years of my life to becoming part of the top 10%, both in results and in value add. Wait! My subconscious screamed.

We could have stopped there.

Are we going to be satisfied building software for a dozen people?

---

Bloomberg for Startup Investors

Through April and May of 2013, and could feel some sort of groundswell thinking around “Quantitative VC” which saw various firms positioning themselves based on their sourcing and research tools. Google Ventures, Greylock, Correlation Ventures, Andreessen Horowitz and Sequoia were widely known to have some kind of data-driven aspect to their operations, although no one shared any details.

Leena Rao’s trend-piece in TechCrunch on June 1st was the moment things began to come clear. It was like someone started the play clock, and I wasn’t even through reading the piece before I started drafting an email to pitch Mattermark to her. I remember it was a Friday, and so we went out for our launch on a Monday — moving into our new shared apartment, sick as a dog, after coding furiously for 48 hours to productize the damn thing.

We made people sign up on a wait list, because we hadn’t really optimized anything. It was ugly. It was slow. But it was the start of relieving pain for a set of customers who had been neglected for far too long. In the next three weeks I’d spent more time in Menlo Park than I ever had in my life, cruising up and down Sand Hill Road meeting with partnership after partnership. Except this time there was no pitch, there was no angle other than: let me show you this thing we made, let me teach you how to use it. I scribbled more than 100 pages of furiously scrawled notes.

I didn’t truly know what customer development meant before these four intense weeks. I thought I had done it with Referly, but I realized had been lazy and unfocused by comparison.

A few short weeks after launch, Union Square Ventures became our first paying customer and Albert Wenger penned a post endorsing our product to the community of investors and we were off to the racing signing up VCs.

We could have stopped there.

---

The Deal Intelligence Company

Our customers are venture capitalists, so they think like VCs and often ask:

But isn’t venture capital a small market?

Yes, and we love it! Small is a relative term. The NVCA says there were 462 “active” VC firms in the US in 2010, and when you include all firms who have raised money since 2002 that number climbs to 791. Using the AngelList API, we found 6,961 users with the word “Partner” in their bio.Based on Mattermark’s pricing of $499/month per user, or $50,000/year per firm, the annual revenue opportunity for this initial market is somewhere in the $20M — $40M range.

As a founder who is getting these initial customers to use her product and say “wow” on a regular basis, this is glorious! It’s not the swing-for-the-fences multi-billlion dollar sized market that venture capitalists are looking for, but when you’re not fundraising that doesn’t really matter.

---

Let me repeat that: when you’re not fundraising, it doesn’t really matter whether your immediate customer base is swing-for-the-fences large.

What a liberating realization!

This knowledge, combined with our wonderful seed investors and very healthy annual revenue growth (averaging 40% MoM since we started charging in July 2013) bought us time to explore adjacent market spaces to our initial set of customers. The wonderful thing about speaking frequently to happy customers is that they tell us all sorts of useful things about the world they live in, and as those relationships deepen we have opportunities to continue solving more and more of their problems.

Once we began to demonstrate that we could build quickly and be responsive to feedback and feature requests, our customers started introducing us to their friends from adjacent social circles and professional ecosystems. It turned out these folks had similar problems Mattermark could solve, and this is how we discovered that Mattermark was useful for much more than venture capital deal sourcing.

VCs hang out with angel investors, investment banks, limited partners, growth and private equity professionals, wealth managers, venture bankers and of course meet with hundreds of startup founders each week. As we began talking to all these constituents we learned more about their problems and it became clear Mattermark could be useful to each of these people in different ways, often with only very small improvements that also benefited all our existing customers.

It’s funny looking back, because at first most of these requests were actually kind of annoying, and felt like one-off opportunities that were getting in the way of our existing product roadmap. It was tempting to brush them away as distractions and stay the course with our core product and core customer base, but on our mission to be “revenue first” this time (and also running on very little cash before our bridge round) we were easily persuaded by money. For example, even before we started charging for our SaaS product a customer offered to sign a $50,000 contract to build new functionality that was way down our list, but would ultimately be hugely beneficial to our customers as well as strategic to opening up future markets, so we built it.

With our first taste of revenue it was only a matter of time (about 3 weeks) before we would begin charging for monthly subscriptions to the suite of Mattermark data and tools.

---

What’s Next for Mattermark Deal Intelligence

We’ve got a TON to learn, build, and do to reach our more broadly defined market of deal professionals — people who make a living by sheparding transactions for their organizations (investments, mergers, acquisition, partnerships, sales). Here’s one way to think about the ultimate size and scope of this opportunity:

Thought experiment: if we get 1% of LinkedIn’s 277M users to pay us $99/mo for deal intelligence tools we would make $3.29B/year. Whoa.

— Danielle Morrill (@DanielleMorrill) February 26, 2014

To do this, we are going to need build a lot of product (a great topic for another post, as this one has gotten huge) and will also grow our sales and business operations part of the company insanely over the next few years. 2014 is already off to a great start:

• 10X growth of our annual run rate from July 2013 to February 2014
• Moved out of the apartment and into a real office!
• Team size increasing from 9 to 15 people by the end of March. Adding 2 full-stack developers, 2 sales ops, and 2 account executives
• Current account executives are profitable and earning commission, closing more business than I did in my best month solo.
• Formalized our sales process and organization, dividing out roles for outbound prospecting, inbound lead qualification, closers, and account management as recommended in “Predictable Revenue”
• Added a full time account manager before $2M ARR, as recommended by SaaStr, to reduce revenue risk and scale customer success as we ramp
• Defined sales territories by vertical industry focus (venture capital, private equity, corporate development, business development) with anchor customers won to prove out willingness to buy prior to bringing on an account executive

I’ve never held a sales role or managed a sales team before, and learning how to run this part of the business over the past 9 months has been very rewarding. I have much more appreciation for the unique challenges and management of revenue goals than I ever could have before, and it seems to be working, too.

We’ve grown revenue 10X in the past 8 months.

With an awesome team on track to reach our next milestone of $2 Million in annual run rate it’s time to pass the torch and hire our VP of Sales.

Interested?

Email me at danielle@mattermark.com and let’s chat.

I build software to help venture capitalists source deals, here are the ones I wish I had done

Over the past few years I’ve made a handful of personal angel investments in founders who I think are incredible, and I am proud to be a small part of InternMatch (Andrew and Nathan), Bitnami (Erica and Daniel), LE TOTE(Rakesh and Brett) and Estimote (Jakub, Lukasz and Rafal).

I have two themes I am passionate about:

1. Software Developer Productivity (Bitnami & Estimote)
2. Actualizing Ourselves as “Grown Ups” (Internmatch and LE TOTE)

Both themes come from my own experiences, as a software developer / developer marketing for Twilio and as a 20-something making my way from kid to adult. I’ve been fortunate to know the founders of these companies, and how I came to invest in each one is its own story for another time. 3 of the 4 are still pre Series A, and I am looking forward to watching them grow.

There are many startups I wish I had invested in, whether they fit into these themes or not. Much respect to the folks who identified how awesome they are early and made a deal happen. Hindsight is 20/20 but many of these companies still have many funding rounds to go. As it stands, I’m a happy paying customer of several of them:

RelateIQ — Best CRM I’ve ever used, hands down. I am a paying customer and it is actually starting to replace email for me as well (see me rant about how much I love them as far back as June 2013). Our entire company uses.

Instacart — I’m healthier with fresh food, and use it several times a week. (Much love to my YC batchmates!) We use it both for personal and work.

Uber — Love the experience, my latte budget is now my Uber budget. (Met these dudes getting the service set up with Twilio, in 2009?)

Hired — These guys are just crushing it in recruiting, and we’re using them to find engineers at Mattermark. A friend found a sweet job through them.

DigitalOcean — when developers love it, it has to be good (first made this call in June 2013). Simple cloud hosting is awesome.

Product Hunt — well they don’t actually have any funding, yet. Ryan?

Magisto — mobile video editing is hard, this is awesome and magical so I pay for it.

---

It would be easy to just list all the fastest growing or biggest exits I’ve heard of, but that’s not really the point. Mark Suster wrote a post about the importance of falling in love with the founders as an investor — and in all these cases I’ve fallen in love with the experiences these products enable.

Thanks to these companies for being awesome and useful, and hopefully I’ll catch you next time!

Who would you put in your fantasy VC portfolio?