Vanishing Mediary

I love the phrase vanishing mediary. This is what I aspire to be. It’s the opposite of a visible intermediary.

In our ego-fueled world, many people want to be front and center. Leaders are told to lead from the front, even if all they do is get up on a white horse and exit stage left as soon as the battle starts. We all know the leaders who are more about themselves than about the organizations and the people they lead. Many of us interact with this type of leader on a daily basis and, while it can be invigorating for a while when things are going well and there are bright lights shining all around you and celebrations around every corner, it’s often complete and total misery when things get tough.

The media wants hero stories. It also wants goat stories. The most glorious media story arc is rags to riches to rags with redemption back to riches. None of this is new – it’s been going on since the beginning of time. Just look at the covers of magazines going back 100 years. And I find it completely boring and tedious.

I can’t remember who first shared the word vanishing mediary with me (if it was you, please tell me so I can update this post) but I instantly loved it. It’s the notion of a leader who helps get things started and gets out of the way. She’s available if needed, and continues to lead by example, but doesn’t need to be front and center on a daily basis. When needed, especially when things are difficult, complicated, or a mess, she shows up, does her thing, and then gets out of the way again.

When I reflect on how I like to lead, it’s very consistent with the notion of a vanishing mediary. As an investor, as long as I support the CEO, I work for her. If I’m not needed, I hang out in the background and offer thoughts and data without emotion when I encounter things. If suddenly I’m needed for something, or get an assignment from the CEO or anyone else on the leadership team, I get after it. If there’s a crisis, I’m there every day for the CEO for whatever she needs.

My role with Techstars is similar. While I have some visibility as a co-founder, I offer it up to David Cohen, David Brown, Mark Solon, and the rest of the Techstars leadership team to use however they want. If they need me, I’m there. If they don’t, that’s cool. I’m a resource that can appear on a moments notice and provide any kind of leadership they need but I don’t have to be front and center.

Great startup communities work the same way. Whenever someone introduces me as the leader of …, the king of …, or the creator of the Boulder Startup Community, I cringe and go into a rant about how I’m not that. I’m just one of the many leaders in the Boulder Startup Community. I’ve helped create a number of things that contribute to it and I play an active role in it. But, like many others, including serial creators like Andrew Hyde (Startup Weekend, Ignite, TEDx Boulder, Startup Week, now at Techstars) I am most happy when I can hand something off that I created to someone else to take it to the next level (Entrepreneurs Foundation of Colorado is a great example of this – thanks to my co-founder Ryan Martens and my partner Seth Levine for providing leadership that has made it what it is today.)

In the 1990s, I ended up being a chairman or co-chairman of a bunch of companies, including two that went public. Today, even though I’m asked, I don’t want to hold the title of chairman for anything (there are a few exceptions – all non-profits). I don’t want to be at the top of the organizational hierarchy. I can play a strong leadership role through my actions, rather than by a title that anoints me.

Most of all, I want to provide leadership through doing. And I think I can best do that by being a vanishing mediary.  And, I recognize that mediary isn’t a well defined word, or may not even be an official word, so hopefully we’ll get an urban dictionary definition of vanishing mediary soon.

Book: Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future

One of my favorite things in the world to do is lay on my couch and read.

Last night I finished Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future by Ashlee Vance. I didn’t expect to love it because I’m usually disappointed by biography written about people who are still alive.

I loved it and couldn’t put it down. I started it Sunday afternoon. A big biography typically stretches out over a week for me so gobbling it up in two evenings was pretty fast for me for a chunky (400+ page) biography.

I don’t know Elon Musk, but I know a lot of characters in the book. I’m friends with his brother Kimbal, who is prominently featured (I’ve invested in two of Kimbal’s companies – OneRiot, which wasn’t successful, and The Kitchen, which is doing incredibly well.) I’ve gotten a taste of Elon through my friendship with Kimbal, but I’m definitely not part of the social circuit the two travel in together, which has limited my frame of reference to random conversations with Kimbal after he’s come back from a SpaceX rocket launch.

In the past few years, Elon’s star as an entrepreneur has been burning bright. Vance’s book does what any good biography should – it covers the good and bad along the journey. Vance expresses his own skepticism and anxiety at the beginning, as his initial efforts to get Elon engaged in the book project didn’t work. Eventually a switch flipped, Elon engaged, Vance used it constructively.

From a purely factual point of view, I have no idea how accurate the book is. But many of the stories line up with whatever I remember from points in time. Some of the negatives are consistent with what I’d heard in the past, while others were new to me. Same with the positives. There’s plenty of broken glass along the way, including some that Elon has famously eaten while staring into the abyss.

Overall, the book paints a very comprehensive picture of someone who on the surface feels extremely complex, but simultaneously very internally consistent. This combination of complexity and consistency is by no means easy, nor does it result in a straightforward person or a clean path from past to present. I think that’s what I liked best about the book – Vance didn’t try to boil it all down, but let it flow with all the messiness that is an amazing life pushing the edge on all dimensions.

Highly recommended.

Cross Dressing With My Email

Here’s a perplexing thing to ponder.

After trying virtually every email configuration on iPhone and Android devices, the best experience that I have had so far is using Microsoft Outlook on my Apple iPhone to access Google Gmail.

I’ve been using Outlook on my iPhone for the past few months. I’ve tried several times to go back to Apple Mail, but it is impossibly bad when compared to Outlook. I’ve also tried using the Google iOS Gmail client, which – while better than Apple Mail – is still very klutzy at certain things.

I know that Microsoft Outlook is really Acompli rebranded at Outlook, but in the eight months since the acquisition the product has continued to get better and better.

Go figure.

Dr. Evil’s Milk Run

Following is a guest post from my friend Eliot Peper. I met Eliot several years ago when he approached me about his first book. I loved his writing and FG Press went on to publish Eliot’s first two books – Uncommon Stock: Version 1.0 and Uncommon Stock: Power Play.

Eliot’s third book, Uncommon Stock: Exit Strategy came out recently and the topic is particularly timely. Enjoy some deeper thoughts of his on why. Oh – and grab Eliot’s books – they are awesome.

Our institutions are failing to protect us. In fact, they’re not even trying. That wasn’t what I set out to discover when I started drafting my first novel. I just wanted to write a page-turner about tech startups with enough real grit to make readers think (true fans may remember that I noted my original inspiration right here in a previous guest post). To research the book, I interviewed federal special agents, financial service executives, money laundering investigators, cybersecurity experts, investors, and technologists in order to deepen the story’s verisimilitude.

The novel turned into a trilogy and along the way I discovered how fact can be far more disturbing than fiction (a point of frustration for novelists). Every day, our government officials, bankers, and corporate leaders are betraying our trust through shortsightedness and technical ignorance.

The now-infamous breach of The Office of Personnel Management by state-sponsored Chinese hackers shocked the nation. Detailed background files on more than twenty-two million Americans were stolen. The pilfered data included medical history, social security numbers, and sensitive personal information on senior officials within The Department of Defense, The Federal Bureau of Investigation, and even The Central Intelligence Agency. The national security implications are staggering.

The emperor may have no clothes but he doesn’t stand alone. Every year, hundreds of millions of dollars are spirited away from major financial institutions. The United Nations estimates that organized crime brings in $2 trillion a year in profits and the black market makes up 15–20% of global GDP.

How do cartel bosses, arms dealers, and human traffickers stash their cash? By working with corrupt insiders, exploiting legal loopholes, lobbying crooked politicians, and taking advantage of the same kinds of technical weaknesses that made the OPM hack possible. They are only able to get away with it because banks and regulators turn a blind eye or, more often, don’t even know when it’s happening.

Large organizations like government agencies and international financial institutions started incorporating software into their operations decades ago. Ever since, they have consistently chosen to pile new updates on top of old code rather than rebuild systems from the ground up. Why? In the short run, it’s cheaper and easier to address the symptom instead of the cause. Now, that shortsightedness is catching up with them.

All of this is just what we know about already. It takes a median of 229 days for data breaches to even be discovered. That’s a long time for criminals to be inside our systems, building new backdoors for future exploitation. Worse, institutions are loath to report breaches even when they are uncovered for fear that our trust in them will degrade even further.

The software powering the digital infrastructure of our institutions is a mess of half-measures, lost source code, and mind-boggling integrations. It’s like a vault built out of swiss cheese, a house resting on a matchstick foundation, or the plot of a telenovela. You can choose your own metaphor, but every hole is a VIP ticket for society’s antagonists.

And that’s not all. In a study released earlier this month, The Government Accounting Office found that many federal examiners in charge of bank information security audits have little or no IT training. They also discovered that regulators are not even doing comparative analysis on system-wide deficiencies, limiting their scope to individual banks. Worse, the National Credit Union Administration lacks the authority to examine third party service providers to credit unions, leaving large segments of their systems beyond the jurisdiction of examiners. It’s painfully ironic that at a time when the NSA terrifies us with its digital omnipotence, so many government agencies can’t get their act together for legitimate enforcement. Our watchdogs are asleep on their feet.

Whether their endgames are espionage or financial malfeasance, we’re making it too damn easy for bad guys to do their dirty work. I was only trying to make my books feel real but now reality is forcing me to suspend disbelief. It makes for great plot twists, but verisimilitude isn’t worth this level of vulnerability.

These are big problems. Big problems always represent big opportunities for creative founders. Mattermark just released their first report on the hottest cybersecurity startups. But we need fixes that are even more fundamental than security. We must rebuild the technical infrastructure and human governance systems that shape our institutions. That change might come from an extraordinarily dedicated internal leader or it might emerge from a garage in Boulder.

We need hackers, makers, artists, and independent thinkers. We need to play smarter and think long-term. We need to call our leaders to action. We need to educate ourselves and build a future in which we can thrive, not fight to survive.  

Participate in the Context.IO App Challenge

Dealing with email is something I have become an expert in out of necessity. While it’s out of control, it’s a chore that is wired into my work in a deep way that, regardless of the explosion of real time communication channels, will likely continue to be the least common denominator for communication for the next 100 years.

That is one of the reasons why I’m interested in seeing the projects that come out of the Context.IO App Challenge, a long-format online hackathon that I’ll be judging in a few weeks along with David Cohen, Fred Wilson, Matt Blumberg and Josh Baer.

Context.IO is a product of Return Path, where I’ve been on the board since 2000. It’s an API that developers can use to build applications that integrate their users’ email data (contacts, files, messages, threads, receipts, and rule-based notifications). We’re expecting to see a healthy mix of inbox management tools along with apps that deliver value in other ways outside the inbox. A few of my favorites that have been built in the past using Context.IO are Mailtime, Paribus or Airhelp.

A common question is if projects from a hackathon can become a successful business. Not all ideas will be winners and it depends on the goals of the event and participants. There is certainly a higher chance with an online hackathon like this one where you have months to build something amazing instead of 24-48 hours. One of our portfolio companies, WootMath,  won a similar App Challenge back in 2013.

In some ways, the judging criteria we’ll all be working from are basic questions any founder should ask themselves:

  • Quality of Idea: Is the idea creative and original?
  • Implementation of Idea: Was the idea well executed by the developer?
  • Potential Impact: Does the application solve a specific problem or paint point for its users?
  • Market Readiness: Is the application market ready?

I’m looking forward to seeing what gets built.