Thursday, August 30, 2012

Thank you

I started this blog almost five years ago, on November 6, 2007.

This is my 365th post and -- as of today -- this strangely personal collection of ideas, impressions and hypotheses has been viewed more than 200,000 times. I know that's a drop in the ocean given the 2+ billion connected humans in the world, but it's a staggering number to a 40-something guy in Seattle trying to do something productive with his remaining time on earth.

I am floored by the power of the Web to give any human being with a keyboard and a connected browser a voice -- to offer them a platform for self-expression and connect them with others who share, or wish to challenge, their views. 

More than anything, this one thread -- putting magic in the hands of the many, making the gift of creation and connection available to all -- is my animating passion as an investor. This blog helps keep me connected to that mission in a deeply personal way.

It has taken me a while to find a voice and rhythm as a blogger -- I continue to be awed by Fred Wilson's daily pace and Brad Feld's clarity of vision -- but I have come to love the regular discipline of shaping my messy and unformed ideas into semi-intelligible packages and casting them on the waters of the public Web for anyone to read, react to and call bullshit on.

I'll get back to my usual rantings shortly, but today I just want to say thank you to each of you who have taken the time to visit, read, share, praise or criticize my writings and ideas over the past five years.

You make me better, smarter, happier and more motivated and I am grateful to you for it.

Wednesday, August 29, 2012

Postmodern Software

One of our portfolio CEO's made me laugh -- and think -- this week by describing a new investment opportunity I'm pursing as "very postmodern".

As an undergrad American Studies / Lit geek I spent many happy hours puzzling over the ambiguous and perspective-shifting fiction of writers like Don DeLillo and Donald Barthelme, but before this week's conversation I hadn't heard the "postmodernist" label applied to the current state of the software business.

Of course, as soon as I typed the phrase "postmodern software" into Google, I turned up a fascinating set of citations that traced the term as far back as 2009 (with a focus on software development methods and processess), but progressing to more recent citations that describe the entire polyglot IaaS / SaaS / PaaS landscape as "postmodernist".

The idea hit the mainstream in 2011, when Gartner analyst Anne Thomas Manes asserted in an industry presentation (at Gartner's 2011 AADI Summit) that contemporary IT architecture design solutions require "postmodern" principles. Here's the description from the conference agenda for her track:
"Externalization, consumerization, and democratization are disrupting business-as-usual in IT organizations. Postmodern IT requires a conscious break with the past and the rejection of old narratives. This Summit track explores the latest trends in application architecture."
There's more than tongue-in-cheek lit-geekery at work here: the enterprise software business is currently undergoing a rapid phase of disaggregation and abstraction, both "vertically" (in the form of multi-platform / polyglot Infrastructure- and Platform-as-a-Service environments), and "horizontally" (from integrated, single-vendor enterprise systems to highly fragmented, multi-vendor "best of breed" SaaS environments).

As the pace of software innovation and disruption continues to accelerate, even technically competent enterprises are losing the battle for "single perspective" centralized IT control and provisioning regimes -- organizations just can't ship software fast enough to meet customer demand without loosening their grip on platform selection, tooling and supporting infrastructure services among their many divisions and business units.

What does "enterprise IT" even mean when every user -- both technical and non-technical -- is empowered to chose her own software tools, vendors and and services from the open source / cloud supermarket?

As with literary postmodernism, only the reactionaries believe the user-centric genie can be put back in the bottle. The functional needs of centralized Enterprise IT -- security/access control, provisioning, business intelligence and cost management -- aren't going away, but successful IT managers will have to embrace radically new methods of delivering these services that actually enable agile, user-driven self-provisioning rather than impeding it.

As an investor, I'm excited to see so many entrepreneurs tackling the knotty technical problems embodied in the user-driven enterprise. Companies like AppFog (a Founders Co-op portfolio company), and Cloudability (a TechStars Cloud and PIE PDX grad) are lighting the way for me on this topic, but I'm actively on the lookout for more.

Friday, August 24, 2012

By the numbers: Why early-stage VCs are greedy bastards

I had yet another conversation with a talented entrepreneur today in which I tried to explain why early-stage venture investors (as distinct from angel investors) can't afford to bet on "small" opportunities -- where "small" is defined as exit values in the single- or low-double-digit millions of dollars.

I remember being puzzled and annoyed by this attitude when I was the entrepreneur asking for money, and it's taken several years of hard-won experience as a "professional" seed investor to really grok the truth of it:

Venture math is brutally hard -- especially so for early-stage investors -- and if you're raising seed money that math will probably find its way into your term sheet and cap table.

Rather than just wave my hands over this, I decided to try to lay out the economics of a hypothetical seed fund in a very simple Google Spreadsheet that anyone can play with: you can find it here.

The goal of this exercise was not to model in full detail how a seed-stage venture fund works, but rather to offer a simple, interactive visualization of just why seed investors get so hung up over valuations and ownership stakes (at the beginning) and exit valuations (for that happy few that make it all the way to the end).

If you like, you can save a copy and play with the assumptions to your heart's content (they're in blue) -- and if you make enhancements (or corrections) just let me know and I'll recirculate (UPDATED: see Brad Feld's comment below + revised model reflecting his comments here) -- but the headlines are pretty easy to see.

First, here are the basic assumptions:
  • Our hypothetical $10MM Seed Fund has the capacity to make ~16 investments of $500K each over a 10-year fund life (after netting out the 2% annual expense burden)
  • The average funded company raises a first round of $500K at a $3.5MM pre-money valuation (pace the YC valuation bubble, this is a realistic -- even lofty -- historical average for seed-stage software deals)
  • For its $250K initial investment, the fund's average ownership stake starts at about 6%, and gets diluted down by 33% over the life of the investment (even allowing for a 1:1 reserve ratio for follow-on investment -- i.e., $250K of reserve for every first $250K investment -- later rounds, option pool increases and tuck-in acquisitions inevitably whittle away your early stake)
  • A third of the companies fail outright and another third return capital, leaving just five companies to produce the bulk of the fund's returns.
  • The target returns that venture fund LPs demand to participate in such a risky and illiquid asset class are steep: 3x at a minimum, 5x for (moderate) outperformance
Use these assumptions to backsolve for total required fund return, and here's what you'll see:

The total shareholder value that the fund's five "winners" have to return just to hit the 3x minimum returns hurdle is over $650 million.

The average exit valuation for each of the fund's 5 "winning" deals has to exceed $120 million. And that's just for acceptable performance.

This isn't an extreme case -- if anything my assumptions about the percentage of winners to losers is on the generous side, and the current seed valuation trend (especially for Valley/YC deals) makes things look dramatically worse.

So, as it turns out, there's a very good reason why professional investors screen out deals that don't at least have a shot at a nine-figure exit valuation -- they can't stay in business without them. 

General Partners that don't meet Limited Partner expectations in their current fund (usually) aren't able to raise their next one. And a VC without a fund is just another out-of-work guy in khakis and a blue shirt.

The only real levers fund managers have to manage these lofty expectations are:
  • Owning more -- both by lowering entry valuations and investing more aggressively in the first round (which adds risk by reducing follow-on reserves); and
  • Winning more -- by being smarter, luckier + harder-working than anyone else in the business.
Creating winners happens over time -- years and years of focused effort -- long after that first check clears.

Which explains why investors tend to favor deals with bigger potential outcomes, and also get hung up on the few things they *can* control (or at least influence) at the time of the investment -- things like price, pro rata rights, option pool, board seats, etc. 

Don't weep for the professional seed investor -- all the ones I know (myself included) do it because they love it and can't imagine doing anything else. 

But if you want to raise money from these folks, take a minute to think about how their business works, and don't be offended when they tell you that you're not thinking big enough -- from where they sit, it just might be true.

Wednesday, August 15, 2012

Happy Ears

I first heard this phrase from one of my favorite co-investors. We we chatting during a break in a board meeting in which the CEO was predicting a quick, favorable outcome on a very large enterprise deal. The investor's summary -- which turned out to be correct -- was that the CEO had "happy ears": a tendency to hear only the good news and tune out the bad.

Happy Ears can be an adaptive trait for CEOs, and entrepreneurs more generally. Creating a company from scratch is brutally hard and often discouraging. If you let the bad news get you down too much you'll never make it through.

But too strong a case of Happy Ears in a founder can also drive companies -- and all their employees and investors -- off a cliff.

Andy Grove said it best: "only the paranoid survive". The most effective founders maintain a controlled state of schizophrenia at all times: using their Happy Ears to keep themselves and their teams motivated with big dreams, while at the same time expecting all their best laid plans to go awry.

Shit happens. Deals don't close. Promised term sheets don't appear. Key hires back out at the last minute. Don't let Happy Ears keep you from anticipating -- and recovering from -- the million inevitable setbacks you'll encounter on your way to success.