I got an email from Matt Blumberg this morning with the above image that said,

“We have been blogging for 19 years. I can remember sitting together above Super Liquor futzing with Typepad like it was yesterday.”

“Super Liquor” is Superior Liquor in Superior, Colorado, which was on the first floor of the building off of Hwy 36, which was my office at the time. There was also a pizza restaurant on the first floor.

I asked Matt if we started on the same day because I couldn’t remember. He said,

“Literally the same day.  We sat at a desk right outside your office in Superior, pulled up our laptops, and taught ourselves Typepad together and created our templates.  Fred had already been blogging for about 6 months, and we had dinner the night before (can’t remember where, think The Med) and decided we would give it a try.  We couldn’t find other good examples of VC or CEO blogs. “

I went and looked at some of those first few posts. Matt’s was You’re Only a First Time CEO Once. Mine included To Blog or Not to Blog (which called out a handful of VC bloggers who started before me), Blog tools – Newsgator and Moveable Poster, TDC (Thinly Disguised Contempt), and my first book review: Free Prize Inside the Radioactive Boy Scout Rate Hikes.

My favorite of those was TDC (Thinly Disguised Contempt).

As was the tradition at the time when new bloggers appeared on the scene, Fred Wilson wrote nice posts linking to each of us. His welcome to Matt was Welcome to the Blog World Matt, and his welcome to me was This Is Going To Be Interesting.

This post wouldn’t be complete without my hat tip to Fred, who, in my view, is the OG VC blogger. His first post was creatively (well – not really) titled MY First Post.

19 years is a long time to do anything. It’s close to my board service record, which ironically was on Matt’s company Return Path with Fred. The ending of Fred’s first post resonates with me today as it did 19 years ago.

“I have no idea if i’ll write a lot in my blog or rarely. I hope its a lot, because i have a lot to say. But we’ll see about that.”

Historically, almost everything I do uses a network model. Foundry Group runs as a network. If you take a look at the Foundry Group partner funds or talk to us about our investment strategy, you’ll immediately see the texture of a network. Techstars is a worldwide network that helps entrepreneurs succeed. All of my ideas around Startup Communities incorporate network theory. If you are involved in any organizations I’ve helped create, such as Energize Colorado, you’ll immediately recognize the network model underlying them.

For me, a network is very different than a social network such as Facebook, Twitter, and LinkedIn. Now that my entire life has shifted to a virtual one, I’ve been playing around with a lot of new network concepts and how they apply to work.

My long time friend Matt Blumberg just launched a new company today called Bolster. It’s a new way to scale your executive team and board. Fred Wilson, also a long time friend of Matt’s, has a great detailed post up today about it titled Bolster Your Management Team And Board that goes through Bolster in detail. A key section from Fred’s post is:

The Bolster team believes that scaling a high growth company means that you need to adapt, grow, and supplement your management team continuously along the way. And a big part of doing that is accessing “fractional talent” which means people that don’t work for your company full-time and permanently. All of this is outlined in the Bolster Founding Manifesto which explains why they started this company.

Sign up for Bolster if you:

• are looking to fill executive or board roles
• are looking for a flexible executive role
• are an investor who is looking to connect your CEOs with flexible executive talent

While we are not direct investors in Bolster, we are indirect investors in three of Bolster’s investors: High Alpha, USV, and Costanoa. It’s a great example of our investment strategy around a network model.

I know the near term plans for Bolster and there’s an enormous amount of value coming quickly around executive and board hires, especially on the dimension of networks, inclusion, and diversity. I encourage you to give it a try and get involved at the beginning.

I got the following email from Reid Hoffman this morning.

Inspired by Lin-Manuel Miranda’s Hamilton, I produced a battle rap music video about centralized and decentralized currencies, pitting Alexander Hamilton against Satoshi Nakamoto. I hope the video gets more people talking about crypto and its evolving role in global commerce. 

It seemed oddly coincidental with Fred Wilson’s post from yesterday titled Some Thoughts on Crypto.

I’m waiting patiently for someone to start talking about Crypto AI.

Insight Timer popped up this message after my daily morning meditation yesterday.

I’ve been meditating on and off for a while. But it’s been an on and off thing, not a daily habit.

In April, after some complex emotional dynamics (how’s that for a euphemism), I decided to start meditating daily. I missed a few days here and there and then in mid-May decided to cut the bullshit with myself and just do it first thing every morning when I woke up.

Last week, both Fred Wilson and Seth Godin blogged about the power of streaks and how they’ve both built daily blogging habits. Fred highlighted the same section of Seth’s post that I’m highlighting below, which is just pure gold.

Streaks are their own reward.
Streaks create internal pressure that keeps streaks going.
Streaks require commitment at first, but then the commitment turns into a practice, and the practice into a habit.
Habits are much easier to maintain than commitments.

I made a conscious decision many years ago that I wouldn’t blog daily, but regularly, partly in reaction to my desire to go off the grid for chunks of time (digital sabbath, weekends, weeks, or even longer in some cases.) I didn’t want the blog to be a habit that I did daily, but then took vacations from.

I’m the same with running. It’s a deeply developed habit that I love, but I know the importance of rest, so I don’t try to run every day.

But, for me, meditation is different. I’m 90 days into a daily routine and it has definitely become a habit. It’ll be interesting to see if the streak lasts 180 days, or 365 days, or 3653 days.

I spent the past few days in Tokyo at the Kauffman Fellows Annual Summit. Over the past five years, there has been a large increase globally in the number of venture capitalists and people interested in becoming VCs. As a result, an organization like Kauffman Fellows is more important than ever as it helps build an incredible community of the next generation of VCs to learn from each other.

In the mid-1990s, I learned how to be a board member by sitting on a lot of boards, learning from other experienced board members, and making a lot of mistakes. I still make a lot of mistakes (that’s that nature of venture capital, and of life in general), but I like to believe that I’m a much more effective board member than I was 25 years ago. That said, I still have my bad days and walk out of a board meeting feeling unsettled for one reason or another.

Recently, Mark Suster, Fred Wilson, and Seth Levine each wrote excellent posts on how to be a good board member. Each post is worth reading from beginning to end carefully.

Mark Suster: How to Be a Good Board Member

Fred Wilson: How To Be A Good Board Member

Seth Levine wrote a five post series: Designing the Ideal Board Meeting

• Designing the Ideal Board Meeting
• Before the Meeting
• Your Board Package
• The Board Meeting
• Board Conflict

I especially love Fred’s punch line, which I strongly agree with.

“Which leads me to my rule for being a good board member.

It comes down to one word.

Care.

*If you care, really care, deeply care, like the way a parent cares for a child, you will be a good board member.”*

If you are a board member (or interact with a board as part of a leadership team) and want to go even deeper on this, I encourage you to grab a copy of my book Startup Boards: Getting the Most Out of Your Board of Directors

And, if you are having a board meeting that I’m a part of, take a look at my post from 2014 if you want hints about My Ideal Board Meeting.

It’s the second week of December, which is about the time that all of the predictions for 2019 start occurring. Last week’s announcements of the confidential S-1 filing of Lyft, Uber, and Slack helped prime the pump for some of these. By the way, did anyone other than me think it was a strange turn of events that companies are now announcing their confidential S-1 filing?

Fred Wilson’s post Thinking Ahead To 2019 is worth reading. Unlike the endless stream of predictions that are about to come out, it’s an analysis of the spread between the public market and private company valuations. Fred is not predicting anything in particular but makes several useful observations, including the following:

“And yet storm clouds are on the horizon for the capital markets in 2019. Rates have risen significantly in the last eighteen months, pulling capital out of the equity markets and into the fixed income markets. There are some leading indicators that suggest a business slowdown is on the horizon, which would be the first one in the US in a decade. And, of course, the situation in DC is getting dicey and that will weigh on markets as well.”

Last week I was talking to a friend who is a growth investor. He and his firm see most of the bay area growth deals (e.g. the unicorns stampede to their front door). He made an observation that a number of deals he’s now seeing are for flat rounds with companies that need to raise more money to keep going and he’s feeling the slow down of investor interest at this level. This dynamic is reflected in the article Scooter Firm Chases Funding to Staunch Losses about the current Lime and Bird financings.

Any student of history knows that there is a linkage between the push to the public markets, demand dynamics of the public markets, and the availability and attractiveness of capital in the private markets. If you lived through the Internet-bubble between 1999 and 2002 you know this cycle well. And, you know that the companies that survived it were the ones with very strong fundamental businesses (e.g. Google), regardless of whether they were private or public at the time.

At the same time, entire categories collapsed. The web hosting business – lead by Exodus – almost entirely went bankrupt or was restructured. Out of this mess came several long-term companies and a huge number of pennies on the dollar type acquisitions. If you were on the winning side of this, it was incredibly lucrative, because even in a massive collapse there is a huge long-term opportunity. But you had to be thinking about the economics and capital structure of the business, versus just chasing growth with more equity dollars.

I have no interest in predicting anything, including how any specific category or company will perform. I also have no idea what the timing of anything is. I do know that if you are an entrepreneur or investor, you should pay attention to the context but be very focused on building a durable long-term business. And this moment in time is one that feels like you should be aware of how much capital you have, how you are spending it, and when (or if) you will need to raise more.

Remember – it can all go to zero (a post I wrote when Bitcoin was at $12,000.)

While it’s easy to tell people things, it’s much more powerful to learn things. And, as I get older, I see the same lessons being learned by subsequent generations. While this isn’t a post that says “everything is the same as it was before”, there are foundational lessons in life that play out over and over again.

I spent the weekend with a friend from the last 1990s who was the lead banker on the Interliant IPO (I was a co-founder and co-chairman.) Last night, at the Aspen Entrepreneurs event, I was asked to describe several failures and I rolled out my story about Interliant, which, for a period of time (1999 – 2000) appeared to be hugely successful before going bankrupt in 2002. If you like to read IPO prospectuses, here’s the final S-1 filing after INIT went effective and started trading on July 8, 1999.

A few days ago, Fred Wilson wrote a post titled Capitulation? In the middle, he’s got a sentence about the theme of the post.

“Now, the crypto markets are in the eighth month of a long and painful bear market and we are starting to see some signs of capitulation, particularly in the assets that went up the most last year.”

On January 16, 2018 (almost seven months ago) I wrote a post titled It Can All Go To Zero. While I included a lesson from the Interliant experience, I highlighted the top 10 crypto prices, which had already fallen 30% – 50% from their high points a few weeks earlier.

Compare those to the prices right now.

Bitcoin is down another 50% (from 12,001 to 6,157). Ethereum is down over 75% (from 1,118 to 264). XRP, holding strong as the third most valuable cryptocurrency, is down 81% (from 1.37 to 0.26). Stellar, which rallied from #9 to #5, is only down 55% (0.49 to 0.22).

My guess is there are a lot of people who wish they sold their XRP at 1.37. Or, maybe around its all time high of 3.83 on January 4, 2018.

Capitulation in markets is one of those endless lessons that gets learned over and over and over again. My first moment with this was Black Monday in 1987. But that’s not when I learned the lesson. My foundational moment, where I really learned the lesson, happened during the collapse of the Internet bubble in 2000 and 2001.

It’ll be interesting to see if this is the crypto generation’s capitulation lesson moment.

I love today’s post from Fred Wilson titled The Valuation Obsession. It has some good hints in it about valuation vs. ownership dynamics for founders, employees, and investors. It also calls out the silliness about focusing on the wrong things.

Go read it.

I’m even a bigger fan of a statement Fred makes in the post that William Mougayar calls out in the comments.

“I like to invest in companies that smart people are joining. Capital should follow talent, not talent following capital.“

This is not just a statement on capital. It’s another hint to the importance – to a founder – of building an awesome team at every level of the journey. It matters at the beginning, as things ramp, and as a public company.

Capital should follow talent. That’s a line I know I’ll be using. I’ll try to remember to say “Fred Wilson says capital should follow talent, not the other way around, and I strongly agree.”

The past is ungraspable,
the present is ungraspable,
the future is ungraspable.

– Diamond Sutra

Now that it’s 2018, the inevitable predictions for 2018 are upon us.

I’m not a predictor. I never have been and don’t expect I ever will be. However, I do enjoy reading a few of the predictions, most notably Fred Wilson’s What Is Going To Happen In 2018.

Unlike past years, Fred led off this year with something I feel like I would have written.

“This is a post that I am struggling to write. I really have no idea what is going to happen in 2018.”

He goes on to make some predictions but leave a lot in the “I have no idea” category.

I mentioned this to Amy and she quickly said:

And that, simply put, is my goal for 2018.

As I read my daily newsfeed this morning, I came upon two other predictions that jumped out at me, which are both second-order effects of US government policies changes.

The first is “tech companies will use their huge hoards of repatriated cash to buy other companies.” There is a 40% chance Apple will acquire Netflix, according to Citi and Amazon will buy Target in 2018, influential tech analyst Gene Munster predicts. The Apple/Netflix one clearly is linked to “Apple has so much cash – they need to use it.” While the Amazon one is more about “Amazon needs a bigger offline partner than Whole Foods”, it feels like it could easily get swept in the “tons of dollars sloshing around in US tech companies – go buy things!”

The second is “get those immigrants out of the US, even if they are already here and contributing to our society.” H-1B visa rules: Trump admin considers tweak that may lead to mass deportation of Indians is the next layer down, where the Executive Branch can just modify existing rules that have potentially massive changes.

I’ve been reading The Lessons of History by Will and Ariel Durant. Various Cylons on BSG had it right when they said, “All of this has happened before. All of this will happen again.”

I’ve had an emotionally challenging morning so far. I woke up too early and was deeply agitated. I tried to get rolling, couldn’t, and went back to bed. But I wasn’t able to fall asleep and my brain kept cycling on all the political chaos and societal hatred that is going on. I’ve tried to compartmentalize it but it broke through again the last couple of days after Charlottesville.

I got up and realized the Internet was down. I decided to just go running. Two minutes in, Brooks came up lame and I walked him back home. I started again with Cooper but my left knee was a little twingey so I decided to bail and take a few rest days. The Internet was still down.

Amy and I then spent time at breakfast talking about how to reconcile the intolerable. I felt a little better and was helped by Fred Wilson’s post If You Lie Down With Dogs, You Come Up With Fleas and Mark Suster’s post Finding My Tribe — The Upside of the Downcast Year.

I’m off to grind through a massive backlog of email today. I leave you with a beautiful video of the eclipse from 2015.

Over the weekend, Mark Suster and Fred Wilson each put up awesome posts discussing the idea of profitability in startups. Mark’s is a master class about how to look at the financial characteristics of a startup and Fred’s discusses what he’s been working on with some of his more mature companies.

They are both worth reading right now. I’ll be here when you get back.

Between the spring of 2000 and the end of 2001, I had the worst, most stressful, and most painful business period of my life. While I’m sure the financial crisis of 2008 was worse for many people, for me it paled in comparison to the misery of this 21-month stretch.

A very simple thing happened that year in my world. The market shifted from rewarding (and funding) growth to rewarding (and funding) profitability. It happened over a few quarters, but with the perspective of time and age, it feels like it happened overnight. I remember the trigger point being a 3/20/2000 article in Barron’s titled Burning Up: Warning: Internet companies are running out of cash — fast. I was on the board of several companies on their list of 100 public companies that would be out of money by the end of 2000 and remember that my reaction to the article was anger, frustration with being maligned, and incredulity that Barron’s would write such an irresponsible article.

My reaction was stupid and immature. Instead, I should have paid attention to the message, thought about it, and taken appropriate action. Instead, I, like many of my colleagues (investors, board members, founders, and CEOs), operated in a state of blissful denial until everything blew up.

I learned that the markets reward growth until they don’t. Then they reward profitability. The trick is to be in a position to make the switch when you need to. Lots of CEOs and boards fantasize about this, but don’t actually have a plan in place to do this as they expect the future – where the switch from growth to profitability – will never come. Or, they hope the exit will happen before this moment.

I was too inexperienced in 2000 to understand this. Given the exuberance, many of my mentors, who had been through other financial cycles, chose to ignore this. The phrase “it’s different this time” echoed broadly throughout the land. I succumbed to the siren song of growth at any cost and paid the price – both literally and figuratively.

Now, I have zero prediction for when the markets will shift from rewarding growth to profitability. Instead, I operate under the assumption that this can happen at any time, and the best companies can grow quickly and either be profitable or be able to become profitable by making manageable modifications to the cost structure within whatever cash constraints they currently have.

Some version of this was on my mind when I wrote the post titled The Rule of 40% For a Healthy SaaS Company in 2015 and the post titled Is 2017 The Year Of Flat Headcount? earlier this year. While I think about this regularly, Mark and Fred’s posts prompted me to pile on to their point and write about it.

There’s a special bonus in Mark’s post, which is in the section titled Revenue is Not Revenue is Not Revenue. He does a nice job of discussing the importance of understanding gross margin and has a line that made me smile.

If you’re shaking your head and thinking, “duh” I promise you that even some of the most sophisticated people I know get off track on this issue of “gross revenue” versus “net revenue.”

I’d add that this includes getting confused about GMV and MRR when talking about revenue and amazingly occasionally confusing revenue with income. It keeps going, when one asks the question “does profitability mean being EBITDA positive, cash flow positive, or net income positive? Or something else?”

If you are a CEO of a company and any of this makes you nervous in any way, I encourage you to grab a few of your investors who have been investing in startups for at least 20 years, take them out to lunch, and talk through these issues with them to understand them better and figure out whether or not to care about this in the context of your company.

At 18 minutes into this awesome talk that Fred Wilson did at MIT a few weeks ago, he finishes the statement “The best time to invest in something is ...”

“… when nobody wants to invest in it but you.” He adds “And – you have to believe in it and know why.”

Truer words have never been spoken about investing as, or in, VC. Just don’t forget the phrase “and – you have to believe in it and know why.”

Fred is one of my closest friends in the VC business and someone I’ve learned an amazing amount from him since first meeting him in 1996 when he was just starting to work with one of my male soulmates Jerry Colonna.

Watch the video. Listen carefully. Learn from his experience.

Fred – thank you for everything you’ve done for and with me over the years.

Fred Wilson, Joanne Wilson, Amy, and I are doing our second Monthly Match. This one is in support of the National Immigration Law Center. We will be matching $20,000 of contributions that our respective communities make to NILC.

We’ve made it easy to contribute – simply go to this page on Crowdrise.

Any level of contribution is super helpful. Since we are matching 1:1, each dollar you contribute gets NILC another dollar.

The four of us did this on an impulse last month after the Executive Order on Immigration hit. We were all extremely upset about the executive order and decided to do something about it. We ended up raising over $120,000 for the ACLU over the weekend during a period where the ACLU got a lot of visibility for making the first major move against the executive order and ended up raising over $24m.

As a result, we’ve decided to do a Monthly Match fundraiser (where the four of us match $20,000 in donations) for a different organization that supports the rights of minorities who we feel are at risk under our current administration. We’ve committed to do this for a year and expect this will evolve as things unfold over the course of the year.

The National Immigration Law Center was established in 1978 and is dedicated to defending and advancing the rights of low-income immigrants. Their mission is clear.

At NILC, we believe that all people who live in the U.S.—regardless of their race, gender, immigration and/or economic status—should have the opportunity to achieve their full potential. Over the years, we’ve been at the forefront of many of the country’s greatest challenges when it comes to immigration issues, and play a major leadership role in addressing the real-life impact of polices that affect the ability of low-income immigrants to prosper and thrive.

If this is important to you, please join in on our Monthly Match and make a contribution to NILC. To make sure we see it, follow the directions below:

1. Go to our monthly match page and hit the donate button and give whatever you feel like giving (min is $10).
2. After you complete the donation, TWEET your donation out on the post donation page. That will register it for our match.
3. If you don’t use Twitter, you can forward your email receipt. The instructions will be on the post donation page. We would vastly prefer you tweet it out.

For those of you who are part of our community and support this effort, feel good that you are taking a specific action today to support the rights of all immigrants in America.

This is a line my friend Jerry Colonna uses when something like the AT&T – Time Warner deal occurs. As time passes, the line has shifted to “We were right – just fifteen years early.”

Jerry was Fred Wilson‘s partner at Flatiron Partners. We were all investing in Internet-related stuff at the end of the 1990s. Jerry and Fred had one of the most successful VC funds during this time period until the Internet bubble burst and blew us all up for a while. We made plenty of investments together and I sat on a number of boards with Jerry – we had some big winners and a handful of craters in the ground.

At the peak, AOL bought Time Warner for $162 billion. We only know that was the peak in hindsight – at the time it looked like it validated a lot of what we were doing by investing in the Internet.

“This merger will launch the next Internet revolution,” said Steve Case, America Online’s chairman and chief executive, told a news conference Monday. “We’re still just scratching the surface.”

The market responded according to plan.

“Analysts expect competing Internet and entertainment companies to seek similar deals in hopes of keeping pace with AOL and Time Warner, and some of those stocks also got a lift Monday. Disney jumped $4.81 1/4 to $35.93 3/4 and News Corp. rose $7.31 1/4 to 45.06 1/4 on the NYSE. Lycos leaped $9 to $79.75 and Yahoo! climbed $28.81 1/4 to $436.06 1/4 on the Nasdaq Stock Market.”

Yup – you saw that correctly, Yahoo was at $436 / share. I think it split 2:1 twice, which would have made it priced at $109 / share. It’s currently at $42 / share so if I got the splits right, after its collapse in 2001 to a low of around $5 / share it took it 15 years to claw its way back to $42 / share (a 10x from the low, 40% of its high at the peak.)

Ponder Gartner’s Hype Cycle for a moment. You can apply this to pretty much anything in tech.

2000 was the Peak of Inflated Expectations. 2002 was the Trough of Disillusionment.

Now, choose any new and exciting technology now. Apply Gartner’s Hype Cycle to it. Ponder where you end up.

Steve Case wrote a book earlier this year called The Third Wave: An Entrepreneur’s Vision of the Future. In addition to looking forward to the future, Steve uses his lessons from the past to explore how things play out. It spans the time frame from 1985 – 2015 which you can just lay down on the Gartner Hype Cycle.

• 1985 – 1994 was the initial entrepreneurial Grind
• 1995 – 2000 was the climb up to the Peak
• 2001 – 2002 was the collapse to the Trough
• 2003 – 2012 was the climb to Enlightenment
• 2013 forward has been the plateau of Productivity

In the context of this, the AT&T – Time Warner deal seems extremely well timed and relevant. Now it’s all about execution.

Consider any of Apple / Google / GM / Ford buying Tesla. Where does that fall on Gartner’s Curve? How about the auto industry. Or drones. Or what people are currently calling AI. Or – well – keep going.

One of the biggest challenges in tech is not being right. It’s being ten or fifteen years too early.

If you’ve missed me, it’s because I spent a week in Australia. Ten days ago, after being there for a few days, I came down with salmonella poisoning. I’m finally starting to feel normal again although I’m still exhausted. This has easily been the sickest I’ve ever been.

While I was gone, the gang at Reboot put up the Reboot Podcast #45 – What’s Love Got to Do with It?- with Fred Wilson and Brad Feld which was a delightful conversation between me, Fred, and Jerry Colonna.

The three of us have a 20+ year history that gives me joy every time I think about it.

I first met Fred in the suburbs of Boston at Yoyodyne in 1996. It was also the first time I met Seth Godin. I had just started working with Softbank and had been commanded to go to Yoyodyne and do “due diligence” by Charley Lax. I had no idea what Softbank or Charley wanted in the way of due diligence, so I went, hung out with Fred and Seth, and wrote Charley an email after saying “Looks great – Seth is awesome” or something like that. Softbank (and Fred – via his new firm Flatiron Partners, which was partially funded by Softbank) invested.

I first met Jerry in a conference room at NetGenesis in Cambridge. I was chairman and we has three product lines at that point: NetForm (an HTML form filler that was getting its but kicked by Allaire), NetThread (which was super cool but getting its butt kicked by something – maybe again Allaire), and NetAnalysis, which was the first weblog analysis tool and became the focus of the company. We sold NetForm to a company called Virtuflex (which went on to become Channelwave, which I became an investor in) and NetThread to eShare. Jerry, again through Flatiron (he and Fred had become partners), was an investor in eShare. I joined the eShare board as an outside director. eThread was acquired by Melita International in 1999 after a crazy ride that included a midnight negotiating session on the 173rd floor of some building in midtown Manhattan to try to merge with iChat. I remember walking about at around 2am with Jerry, completely wasted and frustrated. Welcome to 1999.

Over the last 20 years, the three of us have worked on lots of things in different configurations, but I’d put the deep friendship we’ve developed ahead of all of our business deals. We’ve won and lost together, had great moments as well as deep disappointments. But throughout, we’ve stayed best friends.

I enjoyed making the podcast, I hope you enjoy listening to it.

I woke up feeling subdued this morning. I didn’t know why but after talking to Amy I realized that the emotional impact on me of the horror in Nice is weighing on me. Amy described her connection to it to me – she’s been physically in the same spot that the tragedy happened – and even though we are far away, something very personal hit home about the whole thing.

We are long-time friends with Fred and Joanne Wilson. After my call with Amy, I did my daily news routine, which includes a few minutes in Feedly skimming all the blogs I subscribe to and reading the ones that catch my attention. Both Fred’s and Joanne’s did today.

I read Joanne’s post from yesterday titled Pledge 1% first. It perked me up a little and made me smile, as Pledge 1% is the evolution of the Entrepreneurs Foundation of Colorado which I co-founded in 2007. My partner Seth Levine took the lead a few years in and, with a few other people including Ryan Martens, the co-founder of Rally Software, have evolved our model into a national one. It makes me very happy to see it expanding to NYC in a significant way with Joanne supporting it. If you are in NYC and interested in learning more, attend the Pledge 1% Happy Hour on July 27th.

I then ended up on Fred’s blog. He wrote What Do You Do? What Do You Say? about Nice. In many of the recent attacks and violent situations I’ve felt emotional kinship to Fred. He’s written about things right away in words that are heartfelt and reflect my emotions. I’ve commented on the posts, supported the charities Fred has pointed out, such as the Fund for Nice, and occasionally written a post pointing at them. But I’ve definitely been more reserved about my emotions as it takes me at least a day or two to process them, and at that point the world has often moved on from the immediate aftermath of whatever happened.

Today I didn’t feel like waiting. Amy and I have a quiet weekend together and plan to have dinner with my parents and aunt Cindy/uncle Charlie on Saturday and then brunch with David and Jill Cohen on Sunday. These are all people we love deeply and we get to be with them in a very safe and comfortable context. I’m going for two long runs, will spend time finishing up the third edition of Venture Deals, and just being with my beloved.

Against the backdrop of this, the Nice events are extremely unsettling. Fred ended his post with a powerful introspection / call to action:

There is an epidemic in the world, a sickness that is spreading and afflicting more and more people. It is mental illness. We need to diagnose its cause and treat it. Until we do that, we will be facing more of these mornings. I think many of us are wondering what we can do to help with that. I certainly am.

I hear entrepreneurs use the word disruption on a daily basis and continuously hear the cliche change the world. In entrepreneurial circles, it’s clear to me that violence, hatred, and discrimination or whatever you want to label it is another category where we need to pay attention to disruption before it changes the world in ways we don’t want it to. Or that we need to change the world away from the themes that are starting to appear on a very regular basis. I don’t have answers, but I know I’ll have reflections this weekend.

This weekend I’m co-hosting the Reboot.io VC Bootcamp at my house in Boulder. It starts tonight and goes through mid-day Sunday. It’s an experiment with Jerry Colonna and about 15 other VCs to see if the Reboot.io bootcamp construct works with VCs, where the tag line for the experience is:

Practical Skills + Radical Self-Inquiry + Shared Experiences = Enhanced Leadership + Greater Resiliency

It’s either going to be valuable to this group or not. We’ll know more on Monday. The only way to learn is to try.

As part of the pre-work for the weekend, I went back and re-listened to several of the Reboot.io podcasts that Jerry recommended in advance (for you Soundcloud people I made a Reboot.io VC Program collection.)

• Brad Feld
• Fred Wilson
• Bijan Sabet
• Bryce Roberts and Chris Marks
• Parker Palmer​

So, my brain was already trending toward the headspace around radical self-inquiry in the context of venture capital. Yesterday, Fred Wilson wrote what is the best VC-related post of 2016 so far titled Losing Money. In addition to exemplifying the notion of radical self-inquiry, it is filled with gems about how to think about struggling companies and what to do with them in the context of a VC portfolio.

Go read Fred’s post Losing Money right now. I’ll be here when you get back.

When I woke up this morning, I noticed a tweet from Rand Fishkin aimed at me and Fred.

@bfeld Q: Do you regret every investment that fails? Or do you ever think “I’d place that same bet again”? @fredwilson

— Rand Fishkin (@randfish) April 7, 2016

Fred answered “it is one of my weaknesses that I let a bad experience sour me on a market for life.” And, I’ve seen some of Fred’s own behavior around this, as he won’t touch anything hardware-related at all because of some miserable hardware-related failures during the Internet Bubble (or is it “internet bubble” now that the AP Style Guide says not to capitalize internet.)

But I had a different response to Rand’s question “Do you regret every investment that fails?” 

I’d like to think that I no longer regret any investment. As Fred discusses in his post, many VC investments fail. I’ve yet to meet a VC who says “This is a totally shitty company and a lousy opportunity so I’m going to invest in it anyway.” When a VC makes an investment, she is incredibly enthusiastic about the opportunity. If you know that failure is part of the process, then there is enormous emotional dissonance that gets generated if you regret the investment in hindsight, as you are going to have a lot of regret over the years as a VC, which I think creates a very negative feedback loop in terms of how you think about new investments.

Instead of “regret”, I think it’s much more important to embrace failure as part of the overall experience and focus on learning from every investment that fails. And, a failed investment often has many lessons – some new and some old. Some of these lessons are temporal and while others are foundational. In Fred’s post, he opens with:

“I remember back in the mid 90s, I used to say with some pride that I had not lost money on any of my VC investments. Then one day, someone told me “then you are not taking enough risk.” I ended that streak of not losing money on VC investments in the late 90s in a series of epic flameouts. I lost somewhere between $25mm and $30mm on one single investment. I am not proud of those mistakes. They were stupid. I am ashamed of them to be honest. But I learned a lot from them. Not only was my “winning streak” a case of not taking enough risk, it was also a case of not enough learning. The go-go Internet era of the late 90s fixed both of those things for me. I took more risk and learned a ton.“

The bold section is what I’m trying to say. And, when I say “embrace failure”, I’m not suggesting that one be proud of failing, but I also don’t think there’s any shame in failing. There’s only shame in not learning.

The second part of Rand’s question “Or do you ever think ‘I’d place that same bet again’” is more complicated for me and my view diverges from Fred’s quick response of “it is one of my weaknesses that I let a bad experience sour me on a market for life.” For starters, I don’t think of my investments as bets, so I have an immediate knee-jerk reaction to characterizing investments as bets. That always creates fog for me in answering something, so I have to let the fog clear. Then, given that we invest in a set of themes over a very long period of time, a failed invested is a fundamental component of our ongoing learning in a theme. So I thought hard about what about a failed investment would cause me not to invest in some aspect of the investment again.

The answer appeared before me as “bad people.” My favorite entrepreneurs to back are ones who have had success and failure, so I’m very comfortable making multiple investments over time with people I trust and enjoy working with, even if we’ve had failures along the way. But if the people are fundamentally dishonest, immoral, unwilling to listen and learn, or behave in what I consider to be inappropriate ways, I don’t want to work with them again.

So the essence of regret for me comes from when I make a mistake around people. This is not only the founders but also co-investors. And, after 20+ years of doing this, I’m much better (but not perfect) in figuring out in advance who I shouldn’t work with.

I’ve accepted that in the end we all die. So, as part of my own radical self-inquiry, I’ve tried to isolate and limit my own regret to situations where I spent a lot of time and learn (or teach) nothing. Fortunately, this rarely has anything to do with the investments that I make.

Amy and I watched The Big Short on Tuesday with my partner Jason and his wife Jenn. We were electrified as we walked out of the theater – all four of us loved it. Jason commented that it was a particularly impressive movie given the subject matter. I couldn’t stop saying “that’s the best explanation of what created the financial crisis that I’ve ever seen.”

I remember reading The Big Short in 2010 when it came out. I’m a huge Michael Lewis fan and gobbled it down in a day or two. As we walked to the parking lot, I commented that the big four actors (Gosling, Carell, Bale, and Pitt) in the movie totally nailed their roles. I particularly identified with Pitt’s character Ben Rickert (based on Ben Hockett) who lives in Boulder in the movie.

As we got into our car, Amy said, “What do you think is happening today that no one sees?” This was the underlying theme of the movie – there were some completely obvious things in hindsight going on at the time that no one saw, or wanted to see. A few did notice and made huge financial bets, in non-obvious ways – about what they saw and believed was going to happen. Their foresight and conviction paid off massively, but it scarred each of them in different ways that the movie dramatized extremely well.

I like some time to pass before I look at history. While some people are good at reflecting on the past year and looking forward to predict the next year (one of the best in the VC world is Fred Wilson – read his posts What Didn’t Happen, What Happened In 2015, and What Is Going To Happen In 2016), I’ve never been particularly good at a one year time frame. Instead, I generally like a ten year moving window to process things. So, the lens of 2005 (history) and 2025 (future) is the one I’m currently enjoying.

The Big Short is picking up major steam in 2005. The climax happens in 2008 and the denouement continues on until 2011. So, from a history window perspective, the time frame landed directly on my boundary. Subsequently, Amy and I went on a binge the past few days of other media around this, including the movie Too Big To Fail (which is really about what happened in the fall of 2008) and Inside Job (which covers a broader time range, but focused on 2005 – 2008).

As I sit here on January 2nd, 2016, I’m pondering “what is happening today that no one sees?” When I go back a decade, we were just making the decision not to raise another Mobius Venture Capital fund. My partners and I hadn’t yet created Foundry Group. Techstars didn’t exist. Venture Capital and entrepreneurship was dramatically out of favor. Early stage and seed capital was extremely difficult to find.

I remember having deep conviction that there was an enormous wave of technological innovation coming. I knew that many of the things that had been created in the Internet bubble were great ideas, but they were just – as Jerry Colonna and I like to say – a decade ahead of their time. Today, it’s pretty obvious that was correct. At the time, talking about this stuff was a conversation stopper of the sort that Michael Burry (played brilliantly by Christian Bale) seems to generate every time he talks to someone.

Unlike Mark Baum, who is based on Steve Eisman (and played even more brilliantly by Steve Carell), I’m not angry, cynical, and convinced the world is a giant, rigged, inside game. But I do believe that the vast majority of people have absolutely no idea what is really going on, especially those who are in the middle of whatever game they are playing.

While this comes out in The Big Short, it’s even more apparent when you watch (or read) Too Big To Fail. And, while watching Inside Job, you see people lying or trying to obscure the truth in almost every interview. You can’t fake reality – it always catches up with you.

In the mean time, I’m getting ready for the next season of Game of Thrones.

I got the following email recently, titled “Unicorns Without The Magic.”

“With the rise in venture capitalism it’s hard to say the word “start up” and not be offered an abundance of accelerator programmes, free office space, free apartments & a free bible of connections. I myself have felt the pressures of the world of start up wonders & the prospects of investment. Whilst finishing my finals at university, I created my own algorithm for a business model to achieve a sustainable competitive advantage in a digital space. Through this I’m now building my first digital ecosystem, but along with it I’ve been offered numerous places in accelerator programmes, numerous loans and a wave of unicorn magic dust that seems to be collecting in my inbox. I’m not complaining, but what happens if the purpose of a business is greater than ones own self interest and certainly greater than a VCs interest? Our purpose is to give other people the tools to create their own opportunities, which is not necessarily in line with most VCs sentiments. I know in the next five years my company will make a lot of money, but what I don’t know is how as a 23 year old entrepreneur to says yes to the right VC and no to all the magic dust.”

My short answer was:

“My advice is simple – if it doesn’t feel good / right, say no. Keep focusing on building your business. Don’t avoid the interactions, but use your filter – which seems well tuned and appropriate – to make sure you are only spending time with people who you want to spend time with.”

I was reminded of this by Fred Wilson’s post this morning Go East Young Man (or Woman). He tells Henry Ward’s story of the financing for eShares.

“We were 0 for 21 with Silicon Valley VCs. I never got close. Most of the big firms wouldn’t even meet. A few had an associate do a Skype call even though we were 20 minutes away.

After 21 meetings in SV, I took a Hail Mary trip to the east coast and met with 3 funds. All 3 invested.”

We see this all the time. Founders who are entranced with Silicon Valley VCs. They pursue them with no focus on anyone outside of the bay area, get rejected right and left, often by associates, and end up feeling like they’ve failed. Fred’s post – and Henry’s at eShares Series A – has a great punch line that reinforces the importance of a founder having an effective filter.

“Fundraising is simple: find investors that get excited about your company. It is a filtering exercise. Too many founders believe they have the wrong pitch instead of realizing they have the wrong audience.”

Special bonus points (and some 1990s nostalgia for you): Do you remember the other company named eShares which Fred previously invested in via Flatiron Partners? I sat on the board of with Fred’s partner at the time Jerry Colonna. (a) What did they do? (b) Who acquired them? (c) How much where they acquired for? (d) Who did they compete with and what happened to their competitor?

2007 was only 8 years ago. Back then, you could see VCs everywhere tapping away on the Blackberry keyboards. If you don’t believe me, I have video evidence of it from Fred Wilson, Bijan Sabet, Roger Ehrenberg, and Howard Lindzon.

If you, like me, have been grinding along on email and phone calls all day and need a back to the future type of laugh, I think this will do it for you.