Tag: mattermark

Feb 17 2016

Stuff That Caught My Attention This Morning

After all these years, I’m still a heavy RSS user. Every morning I click on my Daily folder in Chrome, open it up, and spend whatever time I feel like on it. The vast majority of what I read is in Feedly and includes my VC Collection as well as a bunch of other stuff. It’s almost entirely tech related, as I stay away from mainstream media during the week (e.g. no CNN, no CNBC, no NYT, no WSJ, no USA Today, no … well – you get the idea) since I view all this stuff as an intellectual distraction (and much of it is just entertainment anyway, and I’d rather read a book.)

This morning I came across a number of interesting things that created some intellectual dissonance in my brain since they came from different perspectives. I’d categorize it as the collision between optimist and pessimist, startup and already started up, and offense vs. defense. However, they all shared one thing in common – the message and thoughts were clear.

Let’s start with Tim Cook’s remarkable Message to Our Customers around the San Bernardino case and the need for encryption. My first reaction was wow, my second reaction was to read it again slowly, and my third reaction was to clap quietly in the darkness of my office. I then went on an exploration of the web to understand the All Writs Act of 1789 which is what the FBI is using to justify an expansion of its authority. I love the last two paragraphs as they reflect how I feel.

“We are challenging the FBI’s demands with the deepest respect for American democracy and a love of our country. We believe it would be in the best interest of everyone to step back and consider the implications.

While we believe the FBI’s intentions are good, it would be wrong for the government to force us to build a backdoor into our products. And ultimately, we fear that this demand would undermine the very freedoms and liberty our government is meant to protect.”

Thank you Tim Cook and Apple for starting my day out with something deeply relevant to our near term, and long term, future in a digital age.

Shortly after I came across Danielle Morrill’s post Surviving Whatever Comes Next and Heidi Roizen’s post Dear Startups: Here’s How to Stay AliveI’m an investor in Danielle’s company Mattermark and was partners with Heidi at Mobius Venture Capital. I have deep respect for each of them, think they are excellent writers, and thought there were plenty of actionable items in each of their posts, unlike many of the things people I’ve seen in the last few weeks about how the technology / startup world is ending.

Unlike the sentiment I’ve been hearing in the background about deal pace slowing down (not directly – no one is saying it – but lots of folks are signaling it through body language and clearly hedging about what they are actually thinking because they aren’t sure yet), our deal pace at Foundry Group is unchanged. Since we started in 2007, we’ve done around ten new investments per year. I expect in 2016 we’ll do about ten new investments, in 2017 we’ll do about ten new investments, in 2018 we’ll do about ten new investments – you get the picture. We have a deeply held belief that to maximize the value and opportunity in a VC fund, investment pace should be consistent over a very long period of time. We did about ten investments in 2007, 2008, and 2009 – which, if I remember correctly, is a period of time referred to as the Global Financial Crisis. Hmmm …

So it was fun to see my partner Seth’s post titled Welcome to Foundry on the same morning as Danielle and Heidi’s posts. That started the intellectual dissonance in my brain. If you want to see what Seth sends every company he joins the board of after we make an investment in, it’s a good read. It also clearly expresses how we approach working with companies the day after we become an investor.

I then read Ian Hathaway‘s great article for the Brookings Institute titled Accelerating growth: Startup accelerator programs in the United StatesThere are a few people doing real research of the impact of Accelerators and Ian’s work is outstanding. If you are interested in accelerators, how they work, how they impact company creation, and what trajectory they are on, read this article slowly. It’s got a bonus video interview with me embedded in it.

I’ll end with Joanne Wilson’s post #DianeProject. Joanne shared a bunch of info about the #DianeProject with me when we were together in LA two weeks ago. While I don’t know Kathyrn Finney, I now know of her and her platform Digital Undivided. I strongly recommend that you pay $0.99 (like I just did) to get a copy of the report The Real Unicorns of Tech: Black Women Founders, #ProjectDianeThe data is shocking, and there is an incredible paragraph buried deep within it.

“A small pool of angel and venture investors fund a majority of Black women Founders. For those in the $100,000-$1 million funding range, a majority of their funders were local accelerator programs and small venture firms (under $10 million in management). One angel investor, Joanne Wilson and Gotham Gal Ventures, has invested in three of the 11 companies that raised over $1 million. On the traditional venture rm side, Kapor Capital and Comcast’s Catalyst Fund have invested in at least two of the Black woman-led startups in the $1 million club. Wilson, Kapor, and Comcast often invest together, aka “co-invest”, in companies, thus increasing the amount of funding a company receives.”

So – was that more interesting than CNN or CNBC?

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Dec 21 2015

Why I Don’t Have To Follow VC Blogs Anymore

Two words: Mattermark Daily

When I started blogging in 2004 I think I was the third VC blogger after David Hornik* and Fred Wilson (if you were, or know, of another pre-2004 VC blogger, please tell me so I can update my historical recollection.)

I remember lots of people asking me why I was doing it. I heard plenty of trash talk from other VCs, especially second hand, such as “He doesn’t have enough to do”, “He’s not spending his time doing his job”, or “What a waste of time.” I didn’t care, as I was doing it – like Fred often said – to help me think out loud in public, learn about different things, and get a conversation going around topics I was interested in. In retrospect, it was also helping me “practice writing” and without all the practice, it’s unlikely I would have ever gotten in the rhythm of writing a book a year.

Today, hundreds of VCs blog. Some are focused on using content marketing strategies to build their brand and reach. Some seem to have a full time person on the team generating content for them. Some do it under their name; other’s do it on their firm’s web site. Even more have tried and never got past a dozen posts.

Regardless of one’s success, it’s become extremely hard to track all the new content coming out and sort the good from the bad. My somewhat up-to-date VC People Feedly collection has 139 feeds in it. But I stopped being rigorous about adding new people about a year ago and rarely added feeds that were directly on firm websites, so I expect there are probably closer to 500 active VC bloggers now. And, this doesn’t include the guest articles that regularly show up on various sites like TechCrunch, VentureBeat, and Business Insider.

Rather than struggle to keep up, I’m just defaulted to relying on Mattermark Daily to tell me what to read each day. And, I always remember what I tell entrepreneurs: “It’s just data – and it’s often wrong.” Read a lot, but always apply your own critical thinking.

*Update: Naval Ravikant told me that he, Kevin Laws, and Andrew Anker were also part of VentureBlog (dating back to 3/2003). It now appears to be Hornik’s blog.

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Jun 2 2015

The Pre-money vs. Post-money Confusion With Convertible Notes

The other day, Mark Suster wrote a critically important post titled One Simple Paragraph Every Entrepreneur Should Add to Their Convertible NotesGo read it – I’ll wait. Or, if you just want the paragraph, it’s:

“If this note converts at a price higher than the cap that you have been given you agree that in the conversion of the note into equity you agree to allow your stock to be converted such that you will receive no more than a 1x non-participating liquidation preference plus any agreed interest.”

I also have seen the problem Mark is describing. As an angel investor, I have never asked for a liquidation preference on conversion that is greater than the dollars I’ve invested. But, I’ve seen some angels ask for it (or even demand it), especially when there is ambiguity around this and the round happens much higher than the cap. The entity getting screwed on this term are the founders, who now have a greater liquidation preference hanging over their heads than the dollars invested by the angels. Mark has a superb example of how this works on his blog.

We’ve been regularly running into another problem with doing a financing after companies have raised convertible notes. Most notes are ambiguous as to whether they convert on a pre-money or a post-money basis. This can be especially confusing, and ambiguous, when there are multiple price caps. There are also some law firms whose standard documents are purposefully ambiguous to give the entrepreneur theoretical negotiating flexibility in the first priced round.

If the entrepreneur knows this and is using it proactively so they get a higher post-money valuation, that’s fair game. But if they don’t know this, and they are negotiating terms with a VC who is expecting the notes to convert in the pre-money, it can create a mess after the terms are agreed to somewhere between the term sheet stage and the final definitives. This mess is especially yucky if the lawyers don’t focus on the final cap table and the capitalization opinion until the last few days of the process. And, it gets even messier when some of the angels start suggesting that the ambiguity should work a certain way and the entrepreneur feels boxed in by the demands of his convertible note angels on one side and priced round VC on the other.

The simple solution is to define this clearly up front. For example, in the Mattermark investment from last year, I said “We are game to do $5m of $6.5m at $18.5m pre ($25m post).” When I made the offer, I did not know how the notes worked, what the cap was, or what the expectation of the angels were. But when Danielle Morrill and I agree on the terms, it was unambiguous that I expected the notes to convert in the pre-money.

In contrast, in the Glowforge deal, which Dan Shapiro talks about in his fun post Glowforge Completed its Series A with an Investor we Never Met, I was less crisp. I knew that Dan’s notes were uncapped with a discount and I knew his lawyer well, so I didn’t define the post-money in this case. Since the notes were uncapped, I expected them to convert into the pre-money. But I didn’t specify it. The notes were ambiguous and we focused on this at the end of the process after docs had gone out to the angel investors. Rather than fight about this, I accepted this as a miss on my part and let the post-money float up a little as a result. The total amount of the notes was relatively small so it didn’t have a huge impact on the economics of the investment but we could have avoided the ambiguity by dealing it with more clearly up front.

Recognize that this is simply a negotiation. In Mattermark’s case where there were a lot of notes stacked up, I cared a lot about the post-money. In Glowforge’s case where the note amount was modest, I didn’t care very much. And, while I care a lot about my entry point as an early stage investor, I’ve learned not to optimize for a small amount in the context of a pricing negotiation.

I think we are just starting to see the complexity, side effects, and unintended consequences created by the massive proliferation of convertible notes over the past few years. I’m pretty mellow about them as I’ve accepted that they are part of the funding landscape, in contrast to a number of angels and VCs who feel strongly one way or the other. As derivative note vehicles have appeared, such as SAFE, that try to create synthetic equity out of a note structure, we’ll see another wave of unintended consequences in the next few years. As someone who failed fast at creating a standardized set of seed documents in 2010, I’ve accepted that dealing with the complexity and side affects of all of the different documents is just part of the process.

Fundamentally, it’s up to the entrepreneur to be informed about what is going on. I hope Mark’s blog post, and this one, are additive to the overall base of entrepreneurial knowledge. And, if Jason and I ever write a third edition of Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist our chapter on convertible notes might now be two chapters.

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Apr 29 2015

Transparent Funding Announcements

We are in a cycle again where how much you raise is the story. It’s what the press likes to write about (e.g. Company X raised Y from A, B, and C). Now that everyone is overly focused on unicorns, the headline number on the valuation (e.g. Company X raised Y at a valuation of Z from A, B, and C) has crept into the story on big rounds.

While this makes for press release fodder and ego gratification, it’s of very little use to entrepreneurs. There’s no real story there. No understanding of the human dynamics behind the financing. No understand of what actually went down. No underlying metrics that drive the financing. No real perspective on how people thought about things and the choices they made. Just happy talk focusing on the dollar raised. Zero educational value around anything.

Recently, the gang at SalesLoft told the detailed story of their $10m financing. Kyle and his team went through Techstars Boulder in 2012 before moving back to Atlanta and being leaders in energizing the Atlanta startup community. Kyle followed the tradition of extreme openness about the financing process that I think Rand Fishkin started with his post three years ago titled Moz’s $18 Million Venture Financing: Our Story, Metrics and Future.

If you’ve never read Rand’s post on our financing, it goes through an extraordinary amount of detail about Moz’s business, the financing process, the terms, and the timeline. Rand did NOT run this by me before posting it – I saw it at the same time as the rest of the world. He did ask if it was ok with me that he’d be this transparent. I reminded him that I signed up for TAGFEE when I invested, it was his company, and he could write whatever he wanted.

After he posted it, he sent around the link to a few prominent people in the tech media. None of them covered the financing in any way. A few days later, I sent out a few emails asking folks I knew at these sites why they hadn’t written anything, since they so quickly write Company X raised Y from A, B, and C. I didn’t get responses from everyone I wrote, but the ones I got back said something like “Rand wrote too much – there was no story here once he put that post up.”

I found that fascinating. When I pondered it, I realized how divergent the media was becoming from what entrepreneurs were thirsty for in terms of substance.

Late last year, Danielle Morrill followed in Rand’s footsteps with an epic post about our $6.5m financing of Mattermark. In it, she talked a lot about the process, just like Rand did, along with disclosing all kinds of information about the business, the valuation, and what she experienced. I also wrote a post about the financing using Mattermark as An Example of How We Decide to Invest.

Interestingly, the media wrote more this time. I don’t know if it’s because Danielle is in the bay area (while Rand is in Seattle), or the story has broadened. But when I go back and read the media stories, they are still overly focused on the amount of the financing, rather than the story behind it.

Another company that did an awesome transparent funding announcement was Buffer (and app and company I love, but am only a tiny investor in via an AngelList syndicate) when they announced We’re Raising $3.5m in Funding: Here is the Valuation, Term Sheet and Why We’re Doing It. Data, data everywhere. And lots and lots of story.

Now, I’m not suggesting that every entrepreneur should write transparent funding announcements. That’s up to the entrepreneur. But I think it’s super valuable to read the ones that are out there. The amount of useful information to entrepreneurs who are building their companies, both for process, dynamics, and comparables, is enormous. And, while these funding stories are positive, the path to them is often a complete mess, such as Rand’s Misadventures in VC Funding: The $24 Million Moz Almost Raised or Danielle virtually stomping her feet in frustration when she wrote Mattermark Has Raised $2M in Our Second Seed Round.

In my book, this is a lot more useful to read than Company X raised Y at a valuation of Z from A, B, and C. Thanks to the entrepreneurs who are brave enough to put this out there.

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Apr 5 2015

The Full Day Quarterly Board Meeting

Mattermark team hanging out in KeystoneI’ve been to a gazillion board meetings. I’ve written a lot about them including a book called Startup Boards: Getting The Most Out of Your Board of Directors and piles of board meetings posts on this blog. I still do a lot of them, but I’ve definitely been on a quest the past few years to (a) figure out what works best and (b) try to organize my world around more effective board meetings based on what I’ve learned.

On Friday, I had a Mattermark board meeting. It was our second one since we invested in Q414. Danielle Morrill wrote a post in February about our first board meeting. It was a long board meeting as I’d reserved from 11am until the end of the day for it, followed by dinner together, but it was very different than the one we just had as we search for our rhythm as a board.

At the first board meeting, Danielle, Kevin, and Andy came to Boulder and spent a few days here together. In addition to the board meeting, they spent a bunch of time with founders in other Boulder-based portfolio companies of ours.

This time the Mattermark leadership team, including Sarah, BT, and Beau came to Colorado. They arrived Thursday night and drove up to my house in Keystone (about 90 minutes away). I got up early Friday morning and drove up there, getting there around 10:00am. The Mattermark gang was up, had just finished breakfast, and were doing what lots of startups do when they are hanging out waiting for an investor to show up (queue photo of people sitting around on their laptops.)

We got a little more coffee and then went downstairs into our big, comfy TV room. Last time, we worked directly in a Google Doc. This time, Danielle made a deck summarizing everything we’d been doing back and forth in via the Google Doc over the past week leading up to the board meeting. The deck looked good on our 75″ TV and we fired up Skype on a laptop at the front of the room for Lisa (who couldn’t come) and Megan (our outside counsel.)

We proceeded to spend until almost 8pm going very deep on various aspects of the business, product, product strategy, organizational dynamics, and goals for Q215. During this time, we took 90 minutes off for lunch and had a bunch of Mexican food at Fiesta Jalisco. At about 7pm we shifted into an executive session of just founders and board and then Danielle and I spent 30 minutes just doing a 1:1.

We then jumped into cars and went out to a late dinner. My favorite Sushi place Kemosabe Sushi had an hour wait so we went to Silverheels Bar and Grill next door. We were done talking business so we talked science fiction, crazy obsessive habits, fun ways everyone had met each other, and the stuff you talk about after a long day together.

They then drove back to my Keystone house to spend the rest of the weekend together. I drove home because I really wanted a weekend with Amy just hanging around and chilling out (she’s taking a nap as I write this.)

Overall, I’ve tried to shift my board meeting rhythm to once a quarter. My favorite board meetings are the ones that including the entire management team. I like to have a meal with the entire management team as part of the board meeting. I like to have social time and give the team time and space to get to know me better, and themselves better, outside the normal pressure of the day to day grind that is startup life.

I’m a very deep believer in continuous engagement with companies I’m an investor in. As a result, I do not like a monthly board meeting rhythm. I think it’s too much overhead on a leadership team and lets investor / board members off the hook for continuous engagement. More specifically, I know many investors who only really engage with companies either around the board meeting, when a transaction is going on, or when there is a crisis. While this might be useful for some people, it’s not my style nor how I like to engage.

I’ve only had a few of these “full-day retreat at my house in Keystone followed by management taking over the house” type board meetings and I really like them. I expect I’ll do more in the future and encourage any of the companies I’m on the board of to take me up on them.

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Feb 16 2015

The First Board Meeting

Do you remember your first board meeting? I do. Well, I sort of do, kind of, maybe.

Danielle Morrill of Mattermark memorialized her first board meeting on the web in her post Post Series A Life: Reflecting on Our First Board Meeting and What It’s Like Working with Brad. It’s a detailed view of her expectations leading up to the first board meeting we had along with the blow by blow from her perspective of the board meeting.

I have two simple pieces of feedback to Danielle, Kevin, and Andy about the board meeting. First, bring the rest of the leadership team the next time so we have a room full of the team for most of the meeting. Second, you did great – I love the style of board meeting we had.

We didn’t have board meetings at Feld Technologies – we didn’t really have a board. There were three owners – me, Dave Jilk, and my dad. Dave and I had a monthly offsite where we went away for a day and an overnight somewhere within driving distance of Boston. We did this eight to ten times a year and these were some of the most powerful and useful working days, and personal days, we had together. Once a year my dad would join us for a long weekend somewhere where we hung out, talked about the business, and drove around New England.

My first real board meeting was at NetGenesis. I remember the place – an MIT classroom. I remember the attendees – Rajat Bhargava, Eric Richard, Matt Cutler, Matthew Gray, and Will Herman. The chalkboard was black, the chalk was white and dusty. Will and I had each invested $25,000 for a total of 20% of the company. It was 1994. The meeting was around a wooden MIT classroom table that looked like it was from 1894. I don’t remember much of the meeting, except we wrote lots of lots of things on the chalkboard. There were no PowerPoint slides.

I remember my first board meeting for a company I joined as an outside board member. This company was SBT Accounting Systems, based in San Rafael, California. I flew to San Francisco from Boston, stayed overnight in the city, and drove over the Golden Gate Bridge. I’d only been to San Rafael once before, presumably to interview for the board position under the auspices of spending the day at the company. I was nervous because I had no idea what to expect. I showed up a little early, was ushered into the very large board room, and fed breakfast of bagels, pastries, fruit, and coffee. For some reason, I remember eating so much that I was full before the meeting started. SBT always had outstanding, freshly ground coffee filtered through Melitta cone filters which meant that I often drank way too much coffee. Unlike my NetGenesis board meetings, and the few others that I had started attending like ThinkFish’s, this one was formal. Everyone took their place at the table, with blue board books in front of them, and “the show” began. After a number of years of faithful service, I left that board, but I learned a lot and remember the time on that board as helpful to forming my view of an ideal board meeting.

My book, Startup Boards: Getting the Most Out of Your Board of Directors, covers what I’ve learned over the ensuing hundreds of first board meetings, and thousands of board meetings, I’ve participated in. While the book was hard to write, and at some points I feared that it would be excruciatingly “boring” to read, the feedback has been positive, especially from entrepreneurs and CEOs like Danielle who are having their first “real board meeting.”

Just remember – keep it real, not fake. Be yourself. And own the meeting.

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Dec 26 2014

The Great Boxing Day Data Cleanse of 2014

I just spent around an hour shrinking my Facebook friends list from 1,500+ to 535. I ignored another 2,000 friend requests. I made my entire Facebook feed from the beginning of time private, which eliminated 33,000+ followers (dear Facebook followers – you really meant to follow me on Twitter, that’s where all the public fun is.) I turned off all my email notifications.

Hint – if you want to do stuff like this, use the iOS app instead of the web app – it’s so, so, so much faster. Last night I tried to do this on the Facebook web app in front of the TV. It was a total fail – every few unfriends caused the page to refresh and I had to start scrolling all over again. This morning I was pleasantly surprised with how much better / cleaner / faster it was with the iOS app.

I cleared out all my outstanding LinkedIn friend requests. I’m much more promiscuous there and will accept anyone who either I recognize, writes me a personal note, or seems interesting. I turned off all my email notifications and re-inserted LinkedIn in my Daily browser folder.

I spent some time fixing up all the friend requests in Goodreads. I don’t care who follows me, but I got rid of the folks I follow who I don’t know and focused that list a lot better to see if the feed would be useful going forward.

I just deleted everything off my iPhone that I never use and put the infrequently used stuff in various folders. That took things from eight screens to two. Charm King – how the fuck did you end up on my iPhone?

It will continue. Feedly – clean up feeds and add ones from companies in our portfolio that I haven’t been following. Consolidate all photos and music in one place and make sure they are accessible from all computers. And whatever else I run into.

There’s something very satisfying about the winter cleaning that I seem to do every year.

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Dec 23 2014

Mattermark – An Example of How We Decide to Invest

There is a moment during the exploration of a new relationship where a switch flips and the answer is “I want to do this.”

With Mattermark, I remember the moment clearly – I was at The Kitchen in Boulder with the founders (Danielle Morrill, Kevin Morrill, and Andy Sparks) and my partner Seth. I had just put a garlic french fry in my mouth (if you’ve never had them at The Kitchen, they are epic) and looked over at Seth. He looked at me and gave me that “yeah – we should do this” look. And that was it.

As an investor for the past 20 years, I’ve had this happen many times. When I first started investing as an angel investor in 1994, I was focused on a very simple set of criteria. First, did I care about / have affinity for the product? Next, were the entrepreneurs obsessed about their product? Last, did I want to be a long term partner with the entrepreneurs?

With a slight diversion in the late 1990’s when everyone (including me) lost their mind for a few years, I’ve held to this algorithm for all my investing. If you look at the boards I’m on, including companies like Fitbit, FullContact, Oblong, Orbotix, littleBits, Yesware, and Return Path, this pattern should be pretty clear. And if you ponder how I originally got involved in Techstars, and how my role has evolved, those three criteria loom large.

I’ve been interested in private company data since I started Feld Technologies in 1987. Well before the web existed, I was physically tearing articles out of industry magazines and sending them to customers, prospects, other entrepreneurs, and my partner Dave, who probably got tired of the stack of paper with notes scribbled on them that landed on his desk each day. I’ve been through multiple iterations of competitive databases, endless applications for trying to keep track of companies I’m either an investor in or compete with, and every different type of alerting system you could imagine.

During the first decade of my experience with this, I couldn’t afford to subscribe to anything. Every now and then I’d get a free trial and realize how shitty the underlying data was. For the past almost 20 years, I’ve been able to afford the subscriptions, but the data is still shitty. There have been several efforts to crowdsource this kind of data, or make it publicly available, but none have resulted in anything magnificent.

So, regarding the question of “do I care about / have affinity for the product of Mattermark”, the answer was a strong, unambiguous yes. I know how hard the problem is, how wide open the opportunity is, how far it will scale in multiple directions (not just the data set, but the use case, target market, and ultimate product family.) My affinity in this case borders on obsession, just like it does with the Contact Management problem.

Now, let’s shift to #2: “Are the entrepreneurs obsessed about their product?” If you know Danielle, Kevin, and Andy, you know the answer is yes. But there’s nothing quite like experiencing it. Over the past year, as I’ve gotten to know Danielle, I’ve seen her obsession and focus, not just on the short term Mattermark product, but on the long game she and the team is playing. During dinner at The Kitchen, which was the first time we were face to face since we’d met at the beginning of the year, and the first time I’d interacted with Kevin and Andy, all I had to do was sit there, prompt every now and then, and I got another layer of product vision. Obsession. Endless intellectual exploration of where this could go. When I challenged ideas, there was no defensiveness, just more exploration. When I suggested things, there wasn’t blanket approval or rejection, but rather a socratic inquiry as Danielle, Kevin, and Andy tried to understand what I was suggesting. I watched Seth do his thing and the gang continue to engage the same way. At some point, Seth and I had the look I referred to at the beginning of this post.

I’ve always been impulsive about #3: “Do I want to be long term partners with the entrepreneurs?” For the first decade of my investing experience, I made a lot of mistakes on this dimension. Howard Diamond, a close friend and entrepreneur I’ve worked with since 1996 (now the CEO of MobileDay), regularly criticized me as been too trusting, too willing to see the good in people, and too patient with people. This kicked me in the ass very, very hard between 2001 and 2004. While it didn’t make me cynical, I calibrated my filters as I slogged through three more very long years between 2004 and 2007. I like to believe that I brought a new frame of reference around this to Foundry Group, informed by Howard’s constructive criticism, feedback from lots of other friends, learning from my mistakes, and all the long-term positive relationships that I now had as a frame of reference.

I also have a lot of people in my world who know me well, know what I like, and know who I will work well with. This includes a small set of VCs, such as Jon Callaghan at True Ventures and Greg Gottesman at Madrona who know me so well that they only approach me with companies and founders they know I will love. But mostly I use the many CEOs and entrepreneurs I have developed a long-term relationship with to help me calibrate what Amy likes to refer to as my “poor impulse control”, sort of like Raven’s from Snow Crash.

The combination of my own experience and feedback from my universe – both good and bad – made it clear that I wanted to be long term partners with Danielle and team. Recognize that I’m not looking for unambiguously good feedback – we are all flawed in different ways, make mistakes, and have endless and enormous opportunities to learn. An understanding and appreciation of that by the entrepreneurs I work with is deeply important to me.

Back to dinner. Seth eventually had to leave and we kept at it for a while. Driving home, I rolled around what was left in my mind as questions and concerns I had about making an investment. When I got home 20 minutes later, I had none. When we got together the next morning for more discussion, it was easy to look forward and pretend I was already an investor, which felt good. At some point, we shifted to a mode where I asked Danielle, Kevin, and Andy what they wanted, expected, and demanded from an investor. I let them ask me whatever they wanted for a while. But by this point I was all in, as long as they wanted to work with me.

Sure, we did some more up front work and some formal legal diligence, but in that moment at The Kitchen, Seth and I knew that we wanted to be investors in Mattermark.

And that was that. Last week we led a $6.5 million round in Mattermark. I’m delighted to finally be an investor in a problem I’ve been obsessed about for 20 years. We are at the beginning of the journey – check back in a decade from now to see whether or not we are successful. But, regardless, this is a team I hope to work with for the rest of my investing career.

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