Brad Feld

Tag: wilson

Bill Gurley wrote an incredible post yesterday titled On the Road to Recap: Why the unicorn financing market just became dangerous … for all involvedIt’s long but worth reading every word slowly. I saw it late last night as it bounced around in my Twitter feed and then read it carefully just before I went to bed so the words would be absorbed into my brain. I read it again this morning when I woke up and I expect I’ll read it at least one more time. I just saw Peter Kafka’s summary of at at Re/code (We read Bill Gurley’s big warning about Silicon Valley’s big money troubles so you don’t have to) and I don’t agree. Go read the original post in its entirety.

Fred Wilson’s daily post referred to the article in Don’t Kick The Can Down The RoadFred focuses his post on a small section of Bill’s post, which is worth calling out to frame what I’m going to write about today.

“Many Unicorn founders and CEOs have never experienced a difficult fundraising environment — they have only known success. Also, they have a strong belief that any sign of weakness (such as a down round) will have a catastrophic impact on their culture, hiring process, and ability to retain employees. Their own ego is also a factor – will a down round signal weakness?  It might be hard to imagine the level of fear and anxiety that can creep into a formerly confident mind in a transitional moment like this.”

Fred and I have had some version of this conversation many times over the past twenty years as we both strongly believe the punch line.

Entrepreneurs and CEOs should make the hard call today and take the poison and move on

But why? Why is this so hard for us a humans, entrepreneurs, investors, and everyone else involved? Early in Bill’s post, he has a section titled Emotional Biases and it’s part of the magic of understanding why humans fall into the same trap over and over again around this issue. The “Many Unicorn founders …” quote is the first of four emotional biases that Bill calls out. If that was it, the system could easily correct for this as investors could help calibrate the situation, use their experience and wisdom to help the founders / CEOs through a tough transitional moment, and help the companies get stronger in the longer term.

Of course, it’s not that simple. Bill’s second point in the Emotional Biases section is pure fucking gold and is the essence of the problem.

“The typical 2016 VC investor is also subject to emotional bias. They are likely sitting on amazing paper-based gains that have already been recorded as a success by their own investors — the LPs. Anything that hints of a down round brings questions about the success metrics that have already been “booked.” Furthermore, an abundance of such write-downs could impede their ability to raise their next fund. So an anxious investor might have multiple incentives to protect appearances — to do anything they can to prevent a down round.”

Early in my first business, a mentor of mine said “It’s not money until you can buy beer with it.” I’ve carried that around with me since I was in my early 20s. Even when I personally had over $100 million of paper value in an company I had co-founded and had gone public (Interliant), I didn’t spend a dime of, or pretend like I had a nickel of, that money. In 2001 and 2002 I learned a brutal set of lessons, including experiencing that $100 million of paper money going to $0 when Interliant went bankrupt. And, as a VC, I experienced a VC fund that was quickly worth over 2x on paper that ultimately resulted in being a money losing fund. I didn’t buy any beer or spend all the money on random shit I didn’t need and fundamentally couldn’t afford.

This specific bias is rampant in the VC world right now. As Bill points out, many funds are sitting on huge paper gains which translate into large TVPI, MOC, gross IRR, or whatever the current trendy way to measure things are. However, the DPI is the interesting number from a real perspective. If you don’t know DPI, it’s “distributed to paid in capital and answers the question “If I gave you a dollar, how much money did you actually give me back?” This is ultimately the number that matters. Structuring things to protect intermediate paper value, rather than focusing on building for long term liquid value, is almost always a mistake.

Let’s go to number three of the emotional biases in Bill’s list:

“Anyone that has already “banked” their return — Whether you are a founder, executive, seed investor, VC, or late stage investor, there is a chance that you have taken the last round valuation and multiplied it by your ownership position and told yourself that you are worth this amount. It is simple human nature that if you have done this mental exercise and convinced yourself of a foregone conclusion, you will have difficulty rationalizing a down round investment.”

This is linked to the previous bias, but is more personal and extends well beyond the investor. It’s the profound challenge between short term and long term thinking. If you are a founder, an employee in a startup, or an investor in a startup, you have to be playing a long term game. Period. Long term is not a year. It’s not two years. It could be a decade. It could be twenty years. While there are opportunities to take money off the table at different points in time, it’s still not money until you can buy beer with it, so the interim calculation based on a private valuation when your stock is illiquid just shifts you into short term thinking and often into a defensive mode where you are trying to protect what you think you have, which you don’t actually have yet.

And then there’s the race for the exit, in which Bill describes the downward cycle well.

A race for the exits — As fear of downward price movement takes hold, some players in the ecosystem will attempt a brisk and desperate grab at immediate liquidity, placing their own interests at the front of the line. This happens in every market transition, and can create quite a bit of tension between the different constituents in each company. We have already seen examples of founders and management obtaining liquidity in front of investors. And there are also modern examples of investors beating the founders and employees out the door. Obviously, simultaneous liquidity is the most appropriate choice, however, fear of price deterioration as well as lengthened liquidity timing can cause parties on both side to take a “me first” perspective.

This is one of the most confounding issues that accelerates things. Rather than making long term decisions, individuals optimize for short term dynamics. When a bunch of people start optimizing independently of each other, you get a situation that is often not sustainable, is chaotic and confusing, and inadvertently increases the slope of the curve. In the same way that irrational enthusiasm causes prices to rise faster than value, irrational pessimism causes prices to decline much faster than value, which increases the pessimism, and undermines that notion that building companies is a long term process.

Those are my thoughts on less than a third of Bill’s post. The rest of the post stimulated even more thoughts that are worth reflecting deeply on, whether you are a founder, employee, or investor. Unlike the endless flurry of short term prognostications that resulted from the public market decline and subsequent rise in Q1, the separation of thinking between a short term view (e.g. Q1) and a long term view (the next decade) can generate profoundly different behavior and corresponding success.


Last week, I joined the board of a new non-profit called Path Forward which has a mission to get people back to work after they’ve taken time off for caregiving. Specifically, Path Forward works with companies to create mid-career internship that are an on ramp back to the paid workforce.

Andy Sautins (at the time Return Path’s CTO) and Matt Blumberg (Return Path’s CEO) came up with the idea two years ago. After running two cycles at Return Path, they expanded it to other companies including ReadyTalk, SendGrid, MWH Global, SpotX, and Moz.

It’s now an independent non-profit organization that was launched last week with posts from Fred Wilson (who is on the board of Return Path with me), Joanne Wilson (who is the board co-chair of Path Forward), Matt Blumberg (CEO of Return Path and board co-chair of Path Forward), and Tami Forman (Executive Director of Path Forward). And, as a bonus, Fortune had a long article explaining things in This Nonprofit Wants To Put Stay-At-Home Moms Back to Work.

I’m very selective about the non-profits I’m on the board of. While I’m involved in a number of them and Amy and I support many others, I’ve limited myself to three non-profit boards at a time. I’ve been chair of NCWIT for many years and co-chair of Startup Colorado since inception. Until last year, I was on the UP Global board, but left the board when UP Global was acquired by Techstars. So, I had an open non-profit board position and immediately said yes when asked by Matt given the mission of Path Forward.

If you have a company in New York, California, or Colorado (they are starting in these three states) that would like to start doing returnships, go to Path Forward and fill out this form. If you are ready to restart your career after taking time off, go to Path Forward and complete this form.

Finally, Amy and I are making a substantial financial contribution and would encourage any reader who (a) supports the mission and (b) wants to give back in some way to go to Crowdrise, hit the donate button, and help support our launch.


After spending most of the day at littleBits yesterday, I finished it with an annual tradition that is one of my favorites.

At 6:45pm Amy and I met Joanne Wilson, Fred Wilson, Matt Blumberg, and Mariquita Blumberg at Marea for dinner. Fred and I are both on the board of Return Path, the company Matt has been running since he co-founded it in 1999. For over a decade, we’ve been having an annual dinner as a group when Amy and I are in NY, usually in the fall.

Joanne generally picks the restaurant and Amy and I are happy to defer to her excellent taste. We are staying at Columbus Circle so this year Joanne picked something within walking distance for us. As Amy and I were walking home around 9:30, we each commented on how wonderful this tradition is.

I woke up this morning thinking about annual traditions. I’m not a Hallmark holiday person, I don’t like Christmas (although I’ve learned not to be grumpy about it), Thanksgiving crushes my soul, and I’ve never really understood Easter. I’ve learned how to give awesome presents on Valentine’s Day, but I think that’s more because I’m uxorious and well-trained. So I like annual traditions that are out of step with everyone elses.

When I reflect on our dinner, and the conversation, the six of us are enjoying marking the passage of time with this tradition. We are all getting older together, a little softer looking (at least me and Matt),  greying at the temples and in the beard (again for me and Matt). We started doing this before Matt and Mariquita had kids and when Fred and Joanne’s kids were pre-teens. All three of Fred and Joanne’s kids are now out of the house and they are starting the empty nest phase of their life.

While it’s amazing to watch time pass, it’s even more powerful to experience the passage of time together. While we all interact regularly, this annual dinner, which is a deeply engaged three-ish hour meal, gives us a chance to really be together, in the moment, and share what is going on. When you link it together over a decade of more of three hour slices, along with all of the other interactions, it allows us to know each other in a uniquely intimate way.

I felt real love and real joy last night. Joanne, Fred, Matt, and Mariquita – y’all are awesome friends. Thanks for being part of my life.


Some of my favorite VC posts are ones that say what the VC posts that say what the VC thinks about how it all works. And – importantly – how it impacts the entrepreneur, his choices, and the dynamics between the entrepreneur and the VC.

Fred Wilson does this regularly. For example, see his post today on Valuation vs. Ownership.

My partner Jason Mendelson does the same. See his recent post The “VC Bargain”. Of course, Jason and I aspired to do the ultimate version of this in our book Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist.

You don’t have to agree with them. That’s what the comments are for. But they each say what is on their mind, why, how they think about it, and what the implications are for them.

If you want another example, take a look at my partner Seth’s post from last year titled I’m getting sick of the bullshit. And then reflect on the post from the anonymous entrepreneur that I highlighted yesterday titled My Startup has 30 Days to Live.

This shit is really hard and really complicated. It’s easy to have a surface view of it, to romanticize it, or to fall in love with the idea of it. Don’t. Do it because you love it. And find partners who want to go on the journey with you.

I’m going to hang out in the comments on Fred’s Valuation vs. Ownership post and Jason’s The “VC Bargain” post today. Come join me and tell me, Fred, and Jason what you think.