Brad Feld

Month: February 2015

I get 300+ non-spam emails a day. No matter how diligent I am at unsubscribing from stuff, I still get an endless stream of valid, opt-in email that I want to unsubscribe to. Google takes good care of my spam and they even jumped all over my complaints about their spam filtering, figured out the problem, and fixed it (thanks friends at Google). So, I’m not talking about spam, but all the rest of the stuff that I don’t need to see right away.

I’ve tried to use Google’s categories, but it doesn’t really work well for me. Others are emails I never want to see and want to unsubscribe from, but (a) it takes longer to do that, (b) trying to unsubscribe from a mobile client is painful, (c) many of my unsubscribes don’t seem to work (I just end up seeing the email again in a few weeks), and (d) the whole experience / UI is sucky.

Now, before you jump to “use a different channel than email”, recognize that I have also Slack, Kato, iMessage, Twitter, Facebook, Skype, and Google Hangouts open on my desktop with stuff hitting them all day long. Voxer lights up regularly on my iPhone, along with notifications from each of these apps. Channel proliferation has become a mess for me and one of the companies we are investors in is working on that problem earnestly.

Ultimately though I spend most of my time in Gmail especially given the amount of email I get from all different senders. It is unyielding – here’s an example from last week.

Email stats from last week

About 25% are emails that I do not need to see right away. Probably 10% are ones that I want to unsubscribe to.

OtherInbox’s Unsubscriber and Organizer solves both of these for me. Josh Baer, a long time friend and leader in the Austin Startup Community, was the co-founder. OtherInbox was acquired a few years ago by Return Path, which I’m on the board of. I used OtherInbox for a little while before and after the acquisition, but in one of my mad Gmail / Chrome plugin-performance-misery-slowdown-cleanup-fits I stopped using it.

OtherInbox folder list

Last fall, after playing the endless unsubscribe-to-clean-things-up-each-morning I decided to try OtherInbox again. I went all in this time. Within one week I was in email heaven.

Here’s how it works. If I want to unsubscribe to something, I simply label it “Unsubscribe” using Gmail labels and I never ever see it again. Then, OtherInbox constantly moves new emails that match certain criteria to folders. This happens automatically and in the background it figures out the organization of the emails.

I can adjust it if I want, but I’ve found that I spend almost no time adjusting it anymore. Typically, I have some unreads in there and they show up as unreads normally do in Gmail, so at the end of the day I just go to label:oib is:unread and take a quick look.

Give Unsubscriber and Organizer a try. I think you’ll find them as magical as I do.


SOPP_BookTourLogo-PNGSean Wise, my co-author for my next book, Startup Opportunities, is a professor at Ryerson University in Toronto. When we first started writing this book in late 2013, we knew that we were going to do both a United States tour and a Canadian book tour. We flipped a coin to see which one we’d do first and Canada won.

The book is comes out in March (pre-order right now to give me some love) and we’re celebrating that with a Central and Eastern Canadian book tour. Sean and I will also be putting the topics in our book directly to work. At each book tour event, a few idea stage companies will be pitching us for an investment prize out of the fund Sean’s involved with, Ryerson Futures.

Canada has always been good to me and I have some fun memories of both work and play from our neighbor in the north. If you’re in the area, join me at one of the tour stops listed below.

March 23rd, 2015: Winnipeg with Innovate Manitoba. Registration here.

March 24th: Waterloo with Communitech. Register here.

March 25th: Ottawa with L-Spark, Algonquin, and Fresh Founders. Register here for the afternoon event.

March 26th: Toronto with Ryerson Digital Media Zone. Register here.

March 27th: Montreal with Real Ventures + portfolio. Register here.

Each of the organizations is an integral part of their startup community. They help out with community engagement, mentorship, and/or capital. In addition to investing a lot of time, energy, and money in their startup communities, they have done a huge amount of work organizing this book tour – thank you, as we couldn’t do this without you.

A number of the most entrepreneurially-minded companies in Canada act as our national sponsors for the Startup Opportunities book tour.

SOPP_Sponsor_Grid_3
Our Naming Sponsor QuickBooks is dedicated to getting new, high-growth businesses off the ground.

BDC Capital is our National Pitch Tour Sponsor and will be joining Sean and I on the judges’ panel at all the events.

Silicon Valley Bank is a close partner to me and my partners at Foundry Group here in the US and I’m excited to work with them in Canada as well.

Startup Canada has embraced the #GiveFirst mindset which has made Boulder a awesome startup community.

Canadian Business is the center of business and entrepreneurial news and information in Canada.

Wiley Canada, who works with Sean Wise his other books, publishes quality business and instructional content.

For more details about the book tour and all the sponsors, you can take a look at document that the FG Press team put together.

If you’re curious about this pitch competition, you can find more information here, and be sure to reach out to the city partners as they are the ones selecting the companies to pitch their events.


Tomorrow, the FCC is expected to vote on a proposal for new rules around Net Neutrality. The vote is likely to be 3-2 in favor of the rules, split along partisan lines (3 democrats, 2 republicans – shocker…). There has been an enormous amount of bombastic rhetoric in the past few months about the issue that has recently become especially politicized in the same way the debate about SOPA/PIPA unfolded.

I’ve been very public about being a supporter of net neutrality and the idea that the FCC should put down clear, legally enforceable rules around it. However, every time I write or tweet something about the topic, I get a flurry of responses telling me why I’m wrong, why this is bad, or why I’m an idiot. I find these helpful as they force me to focus on the objectionable issues, although I have to put some work in to separate the noise from the signal. And unfortunately there’s a lot of noise these days around anything our government tries to do.

I’m not a lawyer, nor do I ever plan to be one, but I spent plenty of time with them. As a result, over the past 20 years I’ve learned a lot about how the law works in the context of innovation, new products, infrastructure, and consumer protection. I’ve been involved in a number of public policy debates, especially around the Internet, innovation, and immigration. And I’ve made a bunch of friends, on all sides of the discussions, who I’ve argued with, agreed with, been frustrated by, and likely annoyed greatly with my strong opinions and continuous questions to better understand whether my opinions are valid. I learn, evolve, and change my mind based on data and compelling arguments, not on sound bites, so this can be hard work to sort through, but it’s the way my brain was trained, both through my experience at MIT and reflecting on many of the successes and failures I’ve had along with what I’ve learned from them.

A few weeks ago I wrote the post Explaining Net Neutrality to My Dad. He and I engaged in a continuous discussion about this in the past few weeks. He’s endlessly intellectually curious and deeply negative about our government as a result of their engagement with the healthcare system so he has been sending me the “anti-net neutrality” and “the government is taking over the Internet” messaging that has been floating around. I was able to directly respond to some of it, especially the real nonsense, but there were some things that I didn’t completely understand, so I talked to some of my lawyer friends about it.

A few days ago, I decided to summarize what I believe to be the truth around several of the key things I keep hearing over and over as opposition to the FCC proposal, especially around the reclassification of ISPs as Title II telecommunication services. My perspective is informed by two meetings I’ve attended with Wheeler – one a year ago where I was terrified by where he was starting from and one a month ago where I strongly endorsed where he had ended up. In the most recent meeting, I learned a lot about his own intellectual framework for what he’s proposing, which I wrote about in my post Death of Distance and the End of Time.

So – here are a few of the things that I’m regularly hearing as opposition to the new FCC proposal, along with what I’ve believe to be the facts. This comes from the premise that I have which is that strong net neutrality rules are critical to protect an Open Internet and that I’m directly aligned with companies like Twitter who recently wrote why they favor #NetNeutrality and Tim Berners Lee, who invented the World Wide Web, who recently said “YES to #NetNeutrality.”

The Government Is Taking Over The Internet: The rules will not lead to the FCC regulating the Internet. The rules around Title II only allow the FCC to regulate transmission which many refer to as the on-ramps to the Internet provided by cable and telephone companies. There used to be rules around this, but there haven’t been for over a year since the federal court struck down the prior rules.

Title II Will Make the Internet a Public Utility: Reclassifying ISPs as Title II “telecommunications services” will not make them “public utilities.” While Title II is the firmest legal ground for the net neutrality rules, the FCC is applying a light-touch version of Title II where there will be no rate regulation, no tariffs, no burdensome administrative filings, and no last-mile unbundling. Instead, there will be prohibitions on blocking, throttling, and paid prioritization.The FCC will be able to stop any practice that harms user choice or edge providers’ ability to reach users and will be able to act on complaints that ISPs are acting unreasonably when they interconnect with transit providers (e.g. Level 3) or content delivery networks (e.g. Netflix, Amazon.)

ISPs and Broadband Companies Will Invest Less In Their Networks: There is no evidence that Title II will cause ISPs to invest less in their networks. Most Wall Street analysts have said that they see no threat to investment from reclassification because there will be no rate regulation. Sprint, Google, Verizon, Charter, Comcast, Time Warner Cable and others have told Wall Street that Title II poses no threat to investment. Mobile voice is already regulated under light-touch Title II and wireless companies invested nearly $300 billion in their networks in the last 20 years.

Obama is Forcing the FCC To Do This: When I met with Wheeler about a year ago, he had a very different starting point around this issue. I had a strong negative public reaction to this during the initial public comment period and made my point of view clear on the original set of proposals along with about four million of my American friends. I’ve been told this was by far the most comments on FCC rules of any sort. The vast majority of people asked for the strongest possible net neutrality rules which align with the Title II approach. These got incorporated into the proposal as a result of this public response and Obama didn’t actually weigh in publicly until after Title II was incorporated into the proposal. When I checked on history, it turns out that it’s not unusual for the President to weigh in on FCC matters as Nixon, Reagan, Clinton, and Bush have all publicly urged the FCC to take certain actions on regulatory matters.

Everything Was Done In Secret: This is a talking point that apparently started when one of the FCC Commissions (Ajit Pai) put it out there that the upcoming final proposal (what government people call “the order”) was not made public before the FCC vote. It turns out that no FCC Chairman has ever made the full text of an order public prior to a vote. Given how the existing process works, which incorporates public comments on the draft (remember those four million comments I mentioned above), the notion around the FCC making the final proposal public before the vote seems like a cynical ploy for delay, as any comment on the proposal would have to then be considered and incorporated, leading to an endless cycle of public comment.

Ultimately, Congress can weigh in with new laws around this. Remember that the FCC can’t make new laws, they can only enforce things under current laws. There’s a clear-minded article in the New York Times this morning titled F.C.C. Net Neutrality Rules Clear Hurdle as Republicans Concede to Obama that create additional perspective on both the partisan dynamics at play along with the challenge that paralyzes Congress in general right now.

While this certainly isn’t the end of this issue, and given the dynamics around networks in general, I expect it will be one we face for the rest of time, I continue to believe strongly in the proposal the FCC is considering. And I’m proud that so many people have engaged constructively in the discussion.


When your website crashes on launch day it really sucks. It’s ridiculous to me that that still happens today as a regular course of business.

Every time a marketing team works with a web design firm, there is the usual painful and broken handoff between the outside agency and the technical operations of the client which culminate on launch day. So many things have to go right for your launch to be flawless: server configuration, load testing, and deployment. For our portfolio companies, this requires diverting senior DevOps engineers to ensure things go right, which of course comes at the expense of delivering and operating their product and even then there are no guarantees.

Our portfolio company Pantheon is fixing this. Today they are launching Pantheon for Agencies, which enables professional web designers and developers to standardize all DevOps for all of their clients and nail every launch every time. If you know anyone who designs or builds websites for a living they should know about it.

It includes Pantheon’s most developer loved features, their enterprise tools for managing teams and websites en masse, and lessons learned powering 85,000 Drupal and WordPress websites. It is available instantly to digital agencies and for free. Agencies that standardize their work on Pantheon are generating hundreds of thousands of dollars a year in additional profit by efficiency gains due to time saved by the Pantheon development and deployment tools.

Pantheon for Agencies gets everyone on the same page with a common set of management and testing tools for clients and their agencies. It makes handoffs seamless and it ensures everything just works the way you expect it to on launch day.

If I take a step back, it’s so clear to me how much the website market needs to change. Websites are a huge industry that is now bigger than digital advertising business, much of which is serviced by digital agencies (e.g. every web design, development, and digital marketing company on the planet.) Until now agencies have had to bear the responsibility of website DevOps for their customers by necessity. At the end of the day agency clients expect their website to work, even if it’s a server problem at 3AM on a client site that the agency last worked on six months ago.

Pantheon fixes this broken and frustrating dynamic. They enable digital agencies to walk into any customer at any scale and know they can nail the launch no matter how demanding the requirements.

Every digital agency should try Pantheon out – it’s free!

And yes – this site is on Pantheon and my friends at Young & Hungry who did the design and migration from my previous hosting hell are now experts at this.


Several years ago, Alex Iskold wrote a great overview of What It Is Like To Sell Your First Company. I thought it was a great description and encourage every entrepreneur who has never been through the sale of a company to read it.

Rereading Alex’s post inspired me to write my first person account of selling my first company. I’m sure I’ll get stuff wrong since it was over 21 years ago (I was 27.) But I’ll try to capture the good stuff that I can remember, especially since I know I had absolutely no idea what I was doing and could only rely on verbal conversations with other entrepreneurs I knew to help me figure things out since there was no web, no real books to read, and entrepreneurship still wasn’t a word being used regularly. When I reflect on it, independent of the modest economics, the experience changed the trajectory of my life in a very powerful and positive way, even though it was an extremely confusing time for me.

It 1993, I sold my first company, Feld Technologies, to a company called Sage Alerting Systems (which, after several name changes, became AmeriData Technologies.) It was a six month journey for me and my partner Dave Jilk which was at some points exciting, often stressful, and occasionally extremely confusing. It didn’t help that I was in the middle of a deep two year depression which I kept hidden from everyone in the world except Dave, Amy (who I was living with at the time before we got married), my parents, Eric von Hippel (my PhD advisor), and my therapist.

It started, like many things, completely randomly. When we installed a network for a client, we used a company called Allcom (run by two brothers – Jim Galvin and Mike Galvin.) They were great guys, easy to work with, and we sent some business back and forth. This was before WiFi networks so the cabling jobs, especially in downtown Boston, were never trivial, especially in the older buildings. One day, Jim called me and said something like, “Brad – we’ve been acquired and the chairman of the company wants to get together with you for lunch.” At the time I had no real idea what this meant, but figured, what the hell, I’ve got to eat.

I had lunch with Jim and Len Fassler at a restaurant near our office by South Station in downtown Boston. I can’t remember the name but it was a funky place I went to all the time. Jim and Len showed up a few minutes after me and we sat at a table. Len looked like a cross between a powerful New Yorker and Yoda – sharply dressed in his jacket and tie but short and with a friendly face weathered from experience. I was nervous. Very nervous.

We ordered and chatted for a little while. Len asked me softball questions about myself, Feld Technologies, what we did, how we did it, how many people we had, and what our backgrounds were. I can’t remember if Dave was there, but I don’t think he was. In the middle of lunch, Len said, “Jim speaks very highly of you. We’d like to buy your company.”

I was in the middle of a bowl of soup. I remember having to use all my self control so it didn’t get spit out all over the table. I wasn’t expecting this in any way, shape, or form.

We kept talking. I asked a bunch of naive questions, in the form of “What do you mean?” I remember feeling completely clueless and out of my depth. Len explained Sage Alerting Systems’ strategy, talked about how as a public company they were doing a rollup and growing quickly through acquisition, and said they were looking for a lot of small companies in the IT services business. They’d acquired a few companies so far and had LOIs out to a few more. They were really happy with Jim, Mike, and Allcom and wanted to buy more companies in Boston. I learned that they weren’t in New York, but were in Stamford, Connecticut, which I’d never been to.

Lunch ended and Len told me to think about it and call him if we were interested. I don’t really remember the next few conversations with Dave and my Dad (who was an advisory and co-owner) but I do remember a lot of vacillation on my part. Eventually Dave and I decided to go to Stamford to visit Len and his partner Jerry Poch.

We made the drive down on what I remember was a brilliantly sunny day. We didn’t really know what to expect, but when we got to Sage’s office, it was a mad-house of phone calls, people moving from room to room with stacks of paper, and rapid discussions. It was a small but lovely office overlooking the Stamford Canal (I think the address was 700 Canal Street). Len’s assistant Mildred, who I ended up getting to know pretty well over the years, greeted us and put us in the big conference room, which wasn’t very big. A new guy I hadn’t heard of yet named Jerry LeBow came in. Jerry, along with Len and Jerry Poch became a very close friend over time, but in this meeting we just sat and listened to him tell us about Sage Alerting Systems (which he was President of), the emergency warning system (which he knew more about than anyone else on the planet), and the technology he was working on. It was a one-way conversation and it became clear at some point that Lebow was filling up airtime while we were waiting for Len, but that was ok because it was interesting and we were nervous.

Eventually Len came in, apologized for keeping us waiting, and sat down to business. He’d asked us to bring our financing statements so he could look at them to come up with an offer. We gave them to him (no NDA required – we didn’t even know, or care, what an NDA was) and he started going through them. We always had very clean financials because we took it seriously so he quickly sized up our income statement and balance sheet. He asked us a few confirmatory questions, including how much salary we were each getting paid, separate from any distributions from the business, which was $100,000 / year each.

He turned over a piece of paper and scribbled an offer on it. It was 40,000 shares of Sage stock, options for another 40,000 shares of Sage stock, the cash and working capital on the balance sheet (which was about $250,000), salaries of 100k for year 1, 110k for year 2, and 120k for year 3, and 10% of the profits of our group going forward. I’m 99% sure that was the offer, although Dave might remember something different, so it’ll be interesting to see if he weighs in here and corrects us.

Len explained that was their formula for doing deals – 2x multiple of Net Income + balance sheet cash + a three year employment deal. At the time, Sage stock was around $6 / share so it was like a $500,000 offer for the business, half with cash that we’d already earned but had tied up in the business, but upside in the stock and the options. Len made the point that the stock and the options had a lot of upside.

By this point I think Len could have offered us $1 for the business and we would have taken it. We were both totally burned out running the company, had never really thought about the business, were excited about the idea of being able to sell it, and entranced by what was going on around us. Remember that I was very depressed (although I used up all my energy not showing it) and I’m sure Dave was totally worn out from dealing with me. I knew I liked Len from lunch and fell in love with him in that meeting, a love which endures to this day.

Len didn’t propose this as a “bid/ask” type offer – it was a very soft, straightforward “take it or leave it” offer – and it was clear that they were doing lots and lots of transactions and if we weren’t interested, that was fine and they’d quickly move on.

Suddenly Jerry Poch came in the room. In contrast to Len’s calm fatherly approach, Jerry was awesomely full of fire, power, and energy. He was loud, aggressive, and enthusiastic. He knew about us, even though we hadn’t met yet, told us how excited he was to be talking to us, and mentioned how the Galvin’s thought we were great and hoped we could do a deal together. And, before I knew it, he was gone, off to the next thing.

I remember meekly telling Len to send us an offer. I remember shaking hands and vaguely felt like we’d just agreed to a deal. We said our goodbyes, Dave and I left the office, and went to our car for the three hour drive back to Boston.

to be continued…


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.


I was fortunate to spend an hour with a group of about 30 people and Tom Wheeler, the chairman of the FCC yesterday morning. It was a super interesting and stimulating conversation that preceded an excellent speech that Wheeler gave on his Net Neutrality proposal. Go read it and ponder it. It’s in English (not legalese), is blunt, direct, and at times humorous. And it hits the soundbites that are being used against “the government takeover of the Internet” and “the end of the Internet as we know it” crowd quite effectively.

But in this post I want to talk about a phrase Wheeler tossed out early in the conversation that really stuck with me. He said:

“In the 1800s, in a very short period of time, we experienced two innovations that created the death of distance and the end of time.” 

If you don’t know what these two innovations were, they are the railroad (death of distance) and telegraph (end of time).

I’ve been very open about my belief, which I wrote about for the first time in my book Startup Communities, that the global financial crisis was the point at which networks overtook hierarchies in importance in our society. And, while I’ve read about the history of railroads and the telegraph, I never really thought about them as the starting point for the creation of networks given the death of distance and the end of time.

It’s a powerful construct. Today we are starting to see the self-actualization of networks and the path to what many refer to as the singularity. Regardless of whether you believe this, are comfortable with it (like I am), or are afraid of it (like many others are), it is inevitable that innovation, networks, machines, and AI will continue to evolve at an extremely rapid pace. If you don’t believe me or understand this, go read William Hertling’s amazing Singularity Novels.

As a species, I do not think we can control this. Nor should we. We should enable it. We should explore ways to make us a more amazing species. A more fascinating society. We should embrace our innovations and evolve with them.

The path we are on started in the middle of the 19th century. The debate over Net Neutrality is a tiny blip on this path. If we study history, at all points along this path companies behave in their self-interest. We expect that. Human behavior and economic interest always move toward the question, “How can I maximize the position I’m in?” Think about the evolution of the railroad industry. Think about the evolution of the telegraph, and then the telecommunications industry. Think about where we would be if AT&T still prevented us from putting non-AT&T manufactured things “on their network.” Or, maybe more importantly, think about where AT&T would be, which given the passage of time would likely be still promoting Picturephones. Ok – that was gratuitous and unnecessary, but I couldn’t help myself.

In our discussion yesterday, the idea of epistemological modesty came up, reminding us that we can’t predict the path of innovation even in something we know well. I live this every moment in my business as a VC and strongly believe that we should enable, not try to control, innovation.

After listening to Wheeler, reading his speech, and thinking deeply about this over the past few years, it’s clear to me that he understands this. And for those saying “he’s using 1930s monopoly-style regulation to have the government control the Internet”, you are simply wrong. Read his words:

“We will forgo sections of Title II that pose a meaningful threat to network investment.  That means no rate regulation. No unbundling. No tariffs or new taxes. I would note that when applied to mobile voice service over the past two decades, the use of such light-touch Title II – which, by the way, was sought by the industry – went hand-in-hand with massive investment.”

It’s really hard to ignore the soundbites and dig into the facts. But I encourage everyone to try.


I spent the weekend in Las Vegas with my dad. He’s almost 77 and I’m 49. We had an awesome weekend which I expect he’ll write about in detail on his blog Repairing the Healthcare System in the next few days since he generally does a really nice retrospective of our annual trip together.

As I was reflecting on our weekend during my flight home yesterday, I remembered a discussion I had with Todd Vernon, the CEO of VictorOps, and a long time friend (we’ve been investors in the last three company’s of Todd’s – Raindance, Lijit, and now VictorOps – going back almost 20 years.)

I was at dinner with Todd, his wife Lura the rocket scientist, Amy, and Krista Marks / Brent Milne a few weeks ago. It was just after we’d closed an investment in Krista and Brent’s company WootMath and the six of us were enjoying a meal at the awesome but very loud Blackbelly. Todd and I were at one end of the table and couldn’t really hear the conversation very well without leaning over so we ended up just talking to each other for a little while. That little while turned into a really intense conversation.

Todd made the assertion that something happens to guys between the age of 47 and 50. We started talking about all of our male friends who had gone through various things between 47 and 50, including all the classic mid-life crisis stuff. We reflected back on what each of us had been through in the past few years and where we had ended up. Some was gossipy, some was introspective, and some was piecing together a puzzle to support the assertion.

After a few examples, it came into clear focus for each of us. Todd said a line that has really stuck with me.

“The age of 47 to 50 is optimizing for what you are. Up to that point, we are optimizing for what you are going to be.”

We both acknowledged that we don’t really know much about the psychology of women (well – generally – but especially in this age range), so I’m focused on what happens to men. When I reflect on my own experience over the past few years, I’ve struggled with depression, had a few health scares and had to come to terms with my older body, practiced the concept of detachment, deepened my relationship with each of my parents, built a sustainable relationship rhythm with my brother Daniel, and developed a new level of deepness in my relationship with Amy.

As we went back and forth, we realized that our time in this age bracket is a confluence of a bunch of decisions we’ve made about life. There’s a classical notion of a midlife crisis, but that cheapens the dynamic. A few of our friends have had relationships, especially with their spouse or significant other, blow up while many others have their relationships deepen. We all bought sports cars in our 30s so that cliche doesn’t really hold, and a group of us were divorced in our early 20s. Bizarrely, many of the guys in the gang of divorcees I’m part of all had their first wife cheat on them in their early to mid 20s, so none of us would ever consider cheating on our current wife as the emotional devastation of a busted marriage from your wife’s affair at that stage in life seems to never go away, at least for us. So, as we rolled it around, it wasn’t really a midlife crisis.

But there is acceptance that we are more than halfway through our lives. Our parents are getting older. Some have passed away, others like my dad acknowledge they are likely in the last decade of their life. If you are courageous like my dad is, you can openly talk about mortality and the implications of it. And, as a son, his mortality immediately reminds me of my mortality.

In Bora Bora when Amy and I were together for a month, we discussed mortality a lot. We talked about having “30 good years left in our normative case.” It could be longer, it could be shorter, and it can’t really be planned for.

As Todd and I cycled on this, we came to the notion of “what you are.” In this 47 to 50 segment, we each have spent a lot of time figuring out what we are and optimizing our lives for it. This notion of what we are isn’t static – we’ll keep learning and evolving – but we are no longer striving for “what we are going to be.” Instead of spending time and emotional energy on this, we are spending our time and emotional energy on what matters to us now. What we care about. Who we care about.

My weekend with my dad was profoundly wonderful. He knows what he is, what he likes, and what he cares about. He’s still learning all the time, but he’s not trying to be something he isn’t. He isn’t striving to be something new. He’s just being him.

Todd and I realized at dinner that we are having a lot of fun and getting a lot of satisfaction out of just being ourselves at this stage of life. We’ve each had lots of ups and downs, but we are each married to amazing women, living in a place that we love, surrounded by people who we love, working on things that give us each meaning, and having time to ourselves and with friends that are satisfying. Sure, we each have crappy moments and lousy days, and we each know that at some point the lights will go out, but for now we are focused on being what we are.


It’s late Saturday night after an awesome day in Las Vegas with my dad. We are doing our annual father-son weekend, where we head out on Friday somewhere he wants to go and return Sunday afternoon. Don’t ask my why we ended up in Vegas – it’s a mystery to both of us, but we are having fun.

Today we bought some art at the Martin Lawrence Gallery, tried to buy tickets to Rod Stewart but finally gave up, headed down to Downtown Las Vegas, had lunch at The Container Park, hung out with Tony Hsieh for a while at his new Airstream Park, had ice cream twice, dined at Nobu at the Hard Rock, and spent a lot of time talking about the government, health care, and net neutrality.

If you read my dad’s blog Repairing the Healthcare System, you know he’s incredibly passionate about healthcare, the importance of the relationship between the patient and the doctor, and how the current administration is completely bamboozling the public while subsequently nationalizing the healthcare system. Ok – that’s probably too soft – he’s certain that the system is being completely destroyed and a total collapse is imminent.

I’m not in the same headspace on this as him so we have entertaining conversations about it. I try to learn as much as I can by listening to him, challenging his assumptions, and going back and forth – sometimes lightheartedly – with my favorite Battlestar Galactica quotes, including “All this has happened before, and it will happen again.” And, as a classic misdirection on my part, I ask him “What do you think Ben Franklin would think of that.”

We have a lot of fun and learn a ton from each other. So when the conversation turned to Net Neutrality, I felt obligated to separate fact from fiction for my dad while at the same time understanding how someone like him was hearing what was going on. Not surprisingly, his understanding, which is consistent with the “anti-government” message, is to be absolutely appalled that the government is trying to control the Internet. Which, after an hour of talking about it, he started to understand that wasn’t really what was going on, or what the debate about the FCC, net neutrality, and Title II was really about.

Over ice cream (#3 for this trip) I drew him a detailed picture on a napkin of how the Internet actually worked. I rarely do this since I just assume everyone understands it. Bad assumption. It was fascinating to answer his questions, explain the parts he had wrong, and help him understand some nuances around data and how it gets from one place to another. At some point I mentioned John Oliver and Cable Company Fuckery to him.

We talked about a bunch of other things at dinner, forgetting for a while about health care, net neutrality, and the government. After ice cream #4, as we were heading up to our room, he said, “Show me that John Oliver thing on Net Neutrality.” So I did. And, if you haven’t seen it in a while, or have never seen it, it’s worth another 13 minutes of your life.

After he saw it, he said, simply, “I get it, but I’m still suspicious of the government’s intentions here.” So we watched a few more videos including this really good summary on The Verge.

We finished things off with the awesome testimony from Brad Burnham at Union Square Ventures in front of the Judiciary Committee last fall. My dad knows and really respects Brad, so after seeing this he totally got the whole picture.