Registration is open for the 2022 Q4 Leadership Bootcamp , which is happening in Boulder, Colorado, on Nov 10-13, 2022.

Regular readers of this blog know about my long-time (back to 1996) friendship with Reboot co-founder and CEO Jerry Colonna . What you may not know is that several years ago, Jerry and his partner Ali Schultz moved exactly 0.8 miles away from me (there is one 40-acre parcel of land between us.) In the evening, when we are both in Boulder (well, Longmont), he sits under his Cottonwood Tree, I sit 0.8 miles away on my couch next to my pool, and we text and wave at each other.

I’ve been to several Reboot Leadership Bootcamps as a special guest. They are unique and powerful experiences for entrepreneurs. As a bonus, the Reboot Retreat Center is actually on my property in a building called “The Carriage House.” Amy and I don’t charge Reboot for the use of The Carriage House – it’s our gift to entrepreneurs and Reboot for this amazing experience.

If you’re looking to reboot and refresh your leadership, join Team Reboot this November 10-13, 2022 , in Boulder, CO, for their fall Leadership Bootcamp.

My partner Chris Moody recently sent around a note on a concept he refers to as Leader Leverage. I encourage every CEO to read and consider it. His rant follows.

Many of you are probably tired of hearing me rant about some form of what I often refer to as “leader leverage”. If you’ve been lucky enough to avoid these rants, the quick summary is that your biggest lever as a board member is the CEO and your biggest lever as CEO is your direct reports. I learned this lesson the hard way running a very decentralized business with 70 offices in 17 countries at Aquent.

https://youtu.be/rlFT-1YV_zQ

A critical learning about a company’s leadership is whether or not employees trust and respect their senior-most manager. Yet, asking this question directly often doesn’t get a great answer. However, asking it indirectly can be magical.

Using an NPS approach, the example below asks the question, “The company is in a position to really succeed over the next three years.” The different answers are by department.

The average employee believes the Company is in a position to succeed over the next three years. The exception is the employees in one particular department (the red box) who all believe the company is completely fucked. This perfectly illustrates the point that the collateral damage of having a bad leader goes far beyond that leader’s ability to perform their technical job because a bad leader will usually poison a team’s perception of the entire company. 

We’ve known for a long time that we needed a new leader in that department for the Company. However, we’ve always viewed the issue with the current leader to be an issue around technical skills. It turns out the ramifications of not having a leader that people can trust and respect goes far deeper.

At Aquent, we found similar results around crazy specific things like compensation where people would go from feeling grossly under-compensated to feeling like they were compensated fairly simply because we made a change in the leader of their market.  

If you found this useful and want more of Moody on topics like this, I encourage you to go watch his vlog Venture Kills . For example:

For the last several months, I’ve heard or read the phrase “the new normal” 7,354 times. I’ve steadily grown tired of it and now I believe it is an invalid concept.

There is no new normal. We have move forward and get better.

Steve Case wrote a great OpEd recently titled There’s no going back to the pre-pandemic economy. Congress should respond accordingly.

This week, Congress will likely take up the next steps in the economic response to the covid-19 pandemic. If the package is like previous efforts, it will focus on trying to turn back the clock to February 2020: treating the economy as if it were Sleeping Beauty, merely needing to be awakened to be fully restored. This strategy is a mistake: Congress needs to stop solely backing efforts to restore the old economic reality and focus on how to develop a new one.

The Kauffman Foundation recently came out with a mission to Rebuild Better .

Comprised of more than 150 entrepreneurship advocates across the country, the Start Us Up coalition is working to elevate the voices of entrepreneurs so policymakers reverse decades of misplaced priorities that have made it far easier for big businesses to grow than for new businesses to start at all. Our goal is not just to restore the economy, but to rebuild better by ensuring all Americans — especially female, minority, immigrant, and rural entrepreneurs who have historically been marginalized by investors and lenders — can turn their ideas into businesses.

The goal should not be the new normal. The old normal didn’t work for many Americans. The old normal had incredible income inequity, racial inequity, gender inequity, and many other inequities. When I wrote that I’m Fast-Forwarding to 2025 , I had this in the back of my mind, but I couldn’t articulate it.

Change is unpredictable, bumpy, impossible to predict, challenging, stressful, and non-linear. But, as humans, all of these things make us incredibly uncomfortable. Often, we want to go back to “the way things were” since that felt safe, or predictable, or even if we didn’t really like it, was at least something we understood.

Going back to the way we were, with some adjustments, is how I interpret the phrase “the new normal.” I don’t think it will work. I don’t think it’s desirable. I don’t think it’s progress.

So many of the leaders I respect like Steve Case and The Kauffman Foundation are being clear about this. They may use different words, but I feel completely aligned with their vision.

I have no interest in a new normal. I’m only interested in something much better across our society that what was the old normal.

I encourage leaders to embrace change. Embrace complexity. Embrace uncertainty. I certainly am.

Our Colorado governor, Jared Polis, displayed an amazing act of leadership in his response to what I consider a question posed in an extreme and divisive way yesterday.

Colorado Gov. Jared Polis gets choked up when he’s asked about people who have compared COVID-19 stay-home orders to Nazism. Polis is Colorado’s first Jewish governor. pic.twitter.com/noJqbqVObZ

— Next with Kyle Clark (@nexton9news) April 15, 2020

The question asked was:

We are hearing a lot of reports around here … about neighbors reporting on other neighbors for not following the orders … rebellion out here against your orders which have been called tyrannical, against local health department orders being equated to Naziism. How do you react to that? What do you say to those people who are clearly getting frustrated with this stay at home order?

I thought Jared’s response was incredible. It included:

As a Jewish American who lost family in the holocaust, I’m offended by any comparison to Naziism. We act to save lives. The exact opposite of the slaughter of six million Jews and many gypsies and Catholics and gays and lesbians and Russians and so many others.

Ok. Pause and consider that for a moment. When you watch the video (which I hope you do), pay attention to Jared’s behavior as he starts to lose his composure, but then regains it.

He follows with:

It’s not a contest to see what you can get away with. It’s a contest to see how well you can stay at home. By not staying at home, by having parties, by congregating, you are not sticking it to the government. You are not sticking it to Jared Polis. You are sticking it to yourself because you are putting yourself and your loved ones in jeopardy and you are prolonging the economic pain and difficulties your fellow Coloradans face.

He finishes with:

Now is the time for us to act with unity, to act together, to do the best that we can …

This is leadership in the time of crisis. This is how I want my leaders to lead and to react to challenging questions, divisive and ad-hominem attacks, and analogies to things that are personally offensive.

Notice that in the midst of a question that clearly provoked an emotional reaction, Jared answered the question incredibly clearly with a positive, thoughtful, and unifying, rather than divisive and hostile, response.

Jared – thank you for your amazing leadership in this crisis. Fellow Coloradans, let’s all pull together in this crisis, no matter what.

Jerry Colonna has written a “must read for everyone on planet earth book” titled Reboot: Leadership and the Art of Growing Up .

Seriously, go buy it right now. I’ll be here when you return.

Regular readers of this blog know that Jerry and I are extremely close friends and have been for 23 years. I first met Jerry when he was beginning his partnership with Fred Wilson at Flatiron Partners. But, I didn’t meet him through Fred. I met him through NetGenesis, a company I was chairman of at the time that had been started by Rajat Bhargava (who we still work with as CEO of JumpCloud ), Matt Cutler (who we still work with as CEO of Blocknative ). I won’t repeat the story of Brad, Jerry, eShare, and NetGenesis , but it makes me incredibly happy to reflect on 23 years of friendship, which nicely lines up with my 23 official years of marriage to Amy .

If you want to get a feel for Jerry, listen to one of my favorite Reboot podcasts, where we flip the script and I interview Jerry.

Jerry has been on the road promoting the book the past few weeks. Dip into a few of the podcasts and interviews or get a taste on the CNN interview that he did.

Reboot: Leadership and the Art of Growing Up is extraordinary. It’s 100% Jerry, on every page, and is the book he was put on this planet to write.

If you are an entrepreneur, investor, leader, or human being, do yourself a favor and read Reboot: Leadership and the Art of Growing Up . I’m serious – it will change how you think about yourself, leadership, and life.

I read Bad Blood: Secrets and Lies in a Silicon Valley Startup last week on my Q2 vacation. In my post talking about the various books I read , I wrote the following about it.

“Every entrepreneur and VC should read this book. John Carreyrou has done something important here. Maybe this book will finally put a nail in the phrase “fake it till you make it”, but I doubt it. The amount of lying, disingenuousness, blatant and unjustified self-promotion, and downright deceit that exists in entrepreneurship right now is at a local maximum. This always happens when entrepreneurship gets trendy. Carreyrou just wrote a long warning for entrepreneurs and VCs.”

This morning, Amy emailed me a link to an article by Matthew Herper titled Elizabeth Holmes’ Superpower . He strongly recommends Carreyrou’s book and talks about his coverage of Theranos and how he was snowed over the years, partly through his interactions directly with Holmes. In contrast, Holmes never talked to Carreyrou, leaving Herper to reflect:

“Holmes never did talk to Carreyrou, leaving her greatest weapon, her weird charisma, holstered. Now his portrayal of her, put together from other people’s recollections, will define her in the public memory, especially if the planned movie starring Jennifer Lawrence gets made. For those of us she did talk to, at least to me, the book presents a humbling puzzle. Why was what seems so visible now invisible when Holmes was in the room?”

While this is all complicated stuff, Herper’s self-reflection is helpful. At a meta-level, it’s just another example of the challenge of promotion vs. substance. Or, aspiration goals vs. what’s actually going on. Or fantasy vs. reality. Or what you hope to create being articulated as what you have created.

Entrepreneurship is incredibly difficult. Among other challenges a founder has is balancing the vision of what is being created compared to what exists today. At the very beginning of the journey, this is easy because it’s obvious that it is all aspirational. But, as things progress, the substance of what has been created so far starts to matter, especially as the founder needs to raise more money to continue to fund the aspiration goals.

The best founders that I’ve worked with combine a mix of their aspirational goals with a real grounding in the current reality of where the business is. They know that their aspirational goals are goals – not current reality. And they know that there isn’t a straight line to the goals. If they use their reality distortion field  as a charismatic founder, it’s to motivate their team to build something, not deceive investors or customers into believing it has been built.

Because, after all, in the end, we are all vulnerable to facts.

I finished James Comey’s book A Higher Loyalty: Truth, Lies, and Leadership  last night. Everyone who thinks or cares about leadership should read it and allow themselves to process it at a meta-level.

I don’t know James Comey and other than seeing his name, photos, opinions, interviews, criticisms, and analysis of him all week, have never really thought much about him. I noticed him during the 2016 election around the Hillary Clinton investigation – both when he announced it, ended it, re-opened it again, and closed it again. I noticed when he was fired and thought everything around it was odd.

I’ve never studied the FBI, know anyone who works there, or have really thought much about its relationship to the rest of the Executive Branch (or the government in general), other than knowing that it is part of the Executive Branch and that the director of the FBI reports to the Attorney General. Beyond than that, most of what I know about the FBI I’ve learned from fictional movies and TV shows, which I know is as accurate as the Fast and Furious movies.

My sense, from all the attention around the book in the last few weeks, was that this would be an important book. I didn’t know how it would be important, but the combination of the extremely aggressive criticism of Comey, the endless ad-hominem attacks on him, the promotion of the revelations that the book held, and a latent curiosity that I had around the dynamics of the director of the FBI before and after the most recent election, caused me to pre-order the book.

I’m going to use the reaction people had to Emily Chang’s book Brotopia: Breaking Up the Boys’ Club of Silicon Valley  to frame my view of Comey’s book. When I wrote the post Book: Brotopia: Breaking Up the Boys’ Club of Silicon Valley  I was simply writing about my reactions and thoughts after reading the book. Over the few weeks following my post, I had several conversations with men, all who I respect, about the book. In most of these conversations, I was surprised that they had a different, and generally negative, reaction to the book from me. When I pressed on why they had the reaction they had, it always came back to an excerpt that was published before the book was released and the ensuing controversy around the event and whether or not it happened as Emily portrayed it in the book. When I asked the question, “Did you read the book or just the excerpt” each one answered some version of “I’ve only read the excerpt.”

The remarkable thing about some of the criticism about Comey and his book was that it occurred before the book was released. The attacks – both substantive and ad-hominem, have been amplified to a volume of 11.

Comey starts the book off strong by acknowledging his own weaknesses and goals for the book. He asserts that he is focused on defining and describing ethical leadership, using his own experiences as support for the ideas of what he believes (and I agree) is a powerful and important leadership approach. While the book uses the format of a memoir, I think he did an excellent job of putting the reader in the moment of the decisions he had to make, how and why he made them, and the legal context in which he made them. As a result, the notion of ethical leadership gets developed and defined throughout the book.

The criticism of the book that I keep seeing focuses on Comey. It talks about his self-absorption, his need for personal absolution, his inability to see things from a perspective other than “his truth”, and a plethora of other weaknesses, including using his personal descriptions of the people he was talking to at various points in the book.

This is why I encourage you to read the book and reflect on it at a meta-level. There are different ways to be a successful leader. Truth and empathy are powerful, and key traits, of many of the great leaders I know and respect. For these leaders, loyalty is earned rather than demanded. Comey casts himself as this type of leader, but also acknowledges mistakes, misjudgments, and conflicts along his journey. This is another powerful message – leaders are imperfect. And, when you reflect on the various anecdotes Comey describes, from his perspective, one can see this very clearly in all of the leaders he describes his interactions with.

As I need a break from current reality, Sunday’s book will be science fiction …

A few weeks ago I was in Atlanta for Techstars Atlanta Demo Day and the Venture Atlanta Conference . I had a great time and it’s fun to see the vibrancy of the Atlanta startup community. My brother Daniel came with me and we had dinner with our cousin Kenny, who lives in Atlanta, so we got some nice, quiet, emotionally intimate family time.

My favorite keynote at Venture Atlanta was from Scott Dorsey . While our paths have intersected for more than a decade and I knew him from a distance, I’ve gotten to know Scott pretty well over the past year. I put him in the awesome category.

If you don’t know Scott, he was the co-founder and CEO of ExactTarget (2000) – one of the original SaaS companies. ExactTarget went public in 2012 and was acquired by Salesforce.com in 2013 for $2.5 billion and became the core of the current Salesforce Marketing Cloud . He was on the Salesforce.com leadership team until he left to start High Alpha in 2015.

If you are doing something SaaS related and you don’t know or follow what Scott says, you should.

At Venture Atlanta, part of his keynote was a riff on the Attributes of Great SaaS Leaders. While the web is peppered with SaaS metrics and the state of SaaS, there’s a dearth of CEO-centric qualitative information. While Scott’s attributes could be for any leader, they are particularly relevant to SaaS CEOs given the dynamic of how high-growth SaaS companies – and great leadership teams – need to work to scale.

His five attributes, which he went deeper on individually in the keynote, reflect his personality and leadership style.

1. Start with the end in mind
2. Are always learning
3. Value team and culture above everything
4. Are both optimistic and never satisfied
5. Give back!

For those of you that are Simon Sinek fans, starting with the end in mind is analogous to starting with your Why. Are always learning is the essence of being a leader in a super high growth rapidly changing world which most SaaS companies operate in. Valuing team and culture above everything is easy to say, but extremely hard to do, especially when your VCs are pressuring you to perform at a certain financial level for rational, or irrational , reasons. Are both optimistic and never satisfied is interestingly similar to Andy Grove’s “only the paranoid survive” while at the same time having a completely different tone.

If you know me, it won’t surprise you that I almost jumped out of my seat at the event and did a happy dance when Scott started talking about Give back! I know I need to train him to say “Give First”, but it’s the same concept. Scott was a leader here, with the creation of the ExactTarget Foundation (now Nextech ) in 2011. Nextech works to elevate technical, critical-thinking and problem-solving skills of K-12 students, inspiring and enabling young people from all backgrounds to pursue careers in technology, so he’s been ahead of the curve on the importance of computer science and technical skills in K-12, something which is a big part of addressing many of the social and educational gaps in our country.

Indianapolis’ startup community, like Atlanta’s, is thriving. There’s no question in my mind that Scott’s leadership has contributed to this in a meaningful way.

All of this comes back to the idea that as a leader you should play a very long game. Scott does this brilliantly and it’s been hugely educational and inspiring to me to get to know him.

Yesterday I talked briefly about taking a break from media. However, I wasn’t precise, as the one thing I read each week is the New York Times Sunday paper. When Amy and I lived in Boston we started reading it every Sunday morning and continued whenever we travelled. Several years ago I started having it delivered to our house on Sunday morning and it is a delightful Sunday morning ritual for us.

Some Sundays I read it quickly – other Sundays I savor it. I generally spend most of my time in The New York Times Book Review, Sunday Business, Sunday Review, and The New York Times Magazine. I turn all the other pages, only stopping when I find a headline that interests me. For example, I learned today from “Jogging the Brain” that running increases neurogenesis, the creation of new brain cells, which is good for recovering from a night of too much drinking. I’m not drinking alcohol right now so this doesn’t apply, but it reminded me of something that I know from experience for some day in the future when I drink too much.

One of my favorite sections is the Sunday Business Corner Office  by Adam Bryant. I read them all and almost always learn something or have an idea reinforced. I also learn about people I often know – either directly or by one degree of separation.

Today’s Corner Office is with John Lilly , a partner at Greylock Partners , is titled Simplify the Message, and Repeat Often . I’ve only met John once in person (for breakfast at the Hotel Gansevoort in NY) but have long followed him on Twitter and occasionally exchanged messages with him. From this near distance, I respect his thinking a lot.

Under the question “Early leadership lessons for you?” he reinforced something I strongly agree with.

“So my big lesson was the importance of a simple message, and saying it the same way over and over. If you’re going to change it, change it in a big way, and make sure everyone knows it’s a change. Otherwise keep it static.”

I think it’s worth repeating.

“So my big lesson was the importance of a simple message, and saying it the same way over and over. If you’re going to change it, change it in a big way, and make sure everyone knows it’s a change. Otherwise keep it static.”

Did you see what I did there?

When we raised the first Foundry Group fund in 2007 we took over 100 first meetings. We told our story several hundred times. As part of it was a slide called “Strategy.” I still repeat the elements of that slide regularly, a decade later, as our core strategy has not changed. Sure – we’ve modified the implementation of parts of the strategy, and learned from what has worked and what hasn’t worked, but the fundamental strategy is unchanged.

When I wrote Startup Communities in 2012, I came up with a concept I call The Boulder Thesis. I have described it in similar language over 1,000 times in various talks and interviews I’ve given since then. If you want the three minute version, just watch the video below.

While I’ve learned a lot about startup communities over the past four years, my fundamental thesis has not changed. When I come out with the book Startup Communities – The Next Generation (or whatever I end up calling it) in 2018, it’ll incorporate all of these new ideas and things I’ve learned, but will be built on a simple message that I expect I’ll say another thousand times.

I regularly see leaders change what they say because they get bored of saying the same thing over and over again. It’s not that they vary a few words, or change examples, but they change the message. As John says so clearly,

“So my big lesson was the importance of a simple message, and saying it the same way over and over. If you’re going to change it, change it in a big way, and make sure everyone knows it’s a change. Otherwise keep it static.”

Enough said, for now.

One of my core values is diversity of everything.

I’ve been involved deeply in several organizations, such as National Center for Women and Information Technology , that have been focused on increasing gender diversity in computer science and entrepreneurship. More recently, I’ve expanded my lens a lot to include many other dimensions of diversity. The mission of the Techstars Foundation , which is improving diversity in tech entrepreneurship, is an example of that.

One thing that I learned from my work with NCWIT is the power of examples. So, Amy and I have been supporting independent filmmakers for a few years. The first film we helped fund was CODE: Debugging the Gender Gap. Then, following the leadership of Joanne Wilson , we helped fund Dream, Girl which you can watch for free on their website until November 14th.

Recently, a group of us have been helping a young filmmaker, Ashley Maria, who is on her own personal journey to find out why careers are much more complicated and difficult when a woman tries to have one.

Pioneers in Skirts  focuses on cultural and personal setbacks women still face in our society when they pursue a career. The film focuses on hot social topics that women encounter – like the mommy penalty and unconscious biases we find in our culture, the need for mentorship, sponsors, and men to advocate for their female co-workers, and how to nip the problem in the bud during adolescence.

Pioneers in Skirts is currently in post-production aiming for an early 2017 premiere in festivals and then VOD, Streaming and Television. Ashley and team need a little more funding to get things done so if you are inclined to support an ambitious young female filmmaker working on what Amy and I think is an important film, go to her support page and make a donation to the effort.

As I procrastinate from going for a run this morning, I started writing a post titled The Pro-Rata Gap Myth. After two paragraphs, I got tired of writing it and hit the “this is bullshit ” wall – it’s too complicated to explain a myth that I’m not sure even matters.

So I deleted the post and decided to tell a story instead. This is a story I roll out occasionally with CEOs to help them explain how their words can easily be misinterpreted by their teams, especially as the teams get bigger. But it’s also a way that CEOs misinterpret what their investors or board members (or chairperson) is saying. And it creates endless organizational waste and misalignment when the CEO / investor / board member / leader isn’t clear about what she is saying and who her audience is.

Between 1996 and 2002 I was co-chairman of Interliant, a company I co-founded with three other people. Interliant bought about 25 companies during its relatively short life, helped create the ASP business (the pre-cursor to the SaaS world we know and love today), went public, and then blew up post-Internet bubble and ultimately went bankrupt before being acquired, partly because we created a capital structure (through raising a bunch of debt) that was fatally flawed, ultimately wiping out all the equity value.

While I learned a ton of finance lessons from the experience, I also learned a lot a leadership lessons. Your wall is dingy is one of them.

We had just acquired a company (I don’t remember which one or in which city) sometime in 2000. I was visiting the company post acquisition and wandering down the main hallway with the founder of the company we had just acquired. We were having a causal conversation and I offhandedly said “wow – your wall is dingy.” We kept walking, I did a Q&A thing with the founder and the company, and then went out to a mellow company lunch celebration type thing.

I had other stuff to do in the city so I stayed overnight and came back in early to have some meetings at the company the next day. As I was wandering down the same hall, I saw that there was a crew already in the office painting the wall with a fresh coat of paint. I got my coffee, wandered over to the founder’s office (he was also already in early), and asked why there was someone in the office painting the wall?

Founder: “You told me the wall needed to be painted.”

Brad: “I did?”

Founder: “It was while we were walking down the hall. We were talking about the new car I was thinking about buying and you said that the wall was dingy.”

Brad: “Oh yeah – that was said out of admiration for how frugal you are. You were telling me how this is the first new car you will have, since all of your other cars have been used cars. I admire how thrifty and scrappy you’ve been and thought I was paying you a compliment.”

Founder: “Shit, I thought you were unhappy with how low rent our offices are and were commenting that we needed to make things a lot nicer.”

Brad: “Double shit. I was saying the opposite. Part of the reason you’ve been so profitable is that you don’t waste money on your offices. This is part of what we love about your company. And it’s part of why we were willing to stretch in the deal – we knew you know how to make money and that you value every dollar.”

We eventually both started laughing. It was a good bonding moment. Fortunately, it was just paint and didn’t cost that much, although it was one of 27,393 incremental expenses that helped sink Interliant, especially in a time when rent was skyrocketing and everyone needed fancier and fancier offices because, well, because everyone else had fancier offices.

Ever since that moment I’ve been a lot more tuned into what I say. I still talk the way I did then – plainly and with whatever is on my mind – but I try to add the reason so that I’m not misinterpreted. If I could teleport myself back to that hallway in 2000, I’d say “Wow – your wall is dingy, and I love it, because it reminds me how frugal you are.”

As a leader your words matter. It’s not that you have to necessarily choose them carefully, but make sure you explain them and try to confirm that they are understood.

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.

As the Boulder Startup Community evolved, I started to become inundated with people who wanted to get involved. Some of these were locals while others where people looking to move to Boulder, or who had recently moved here. Some where people known to me while others were new relationships. As the momentum, size, impact, and reach of the Boulder Startup Community grew, I found myself overwhelmed by the amount of requests I was getting to get together, meet, explore ways to work together, and just generally share food and drink in the quest for figuring out ways to work together.

A while ago I came up with an approach where I could separate leaders from doers from everyone else. I’ve been applying this approach to the Boulder Startup Community, and a number of other things I’m involved in, since then and offer it to you as a simple, yet elegant way to triage an overwhelming amount of inbound requests to figure out who is really going to make shit happen.

The trick: I identify leaders by giving people assignments.

Here’s how it works. I’m going to use a really simple example. Recognize that the range of inbound is all over the place, from a wide range of people, with very different degrees of experience. The initial interactions can be complex and my assignments vary dramatically, but with a goal of intersecting (a) what the person is asking for and (b) a result that will be interesting to me in some way.

So, for a simple case (and assignment), assume that I get an email like the following:

“Brad, I’m new to Boulder and very excited about getting involved in the Startup Community. I moved here from New York and have a deep background in devops, being an entrepreneur, and various meditation techniques. I’d love to get together for a cup of coffee to see how I can get involved in things going on in Boulder. My resume is attached.”

I quickly respond with an assignment. It will be something that will take the person less than 30 minutes to do and require no specific knowledge on their part. For example, my response might be:

“Welcome to Boulder. Unfortunately I don’t have time for coffee in the next few weeks, but I’d be happy to get you plugged in to some of the local entrepreneurs who might be relevant to you. Can you look through our portfolio and tell me who you’d like to get introduced to?”

I never hear back from 50% of the people. I kid you not. It doesn’t matter whether it’s email or someone coming up to me at a public event. I give them a simple assignment, with an easy way to focus what I’m going to do for them so it’s more useful from their frame of reference, and then I never hear back from them again.

This is a very good thing. It reduces my workload of this kind of stuff immediately by half and filtered out people who weren’t going to follow through.

25% (half of the remaining 50%) send me an email something like:

“I took a look at your website and am very interested in VictorOps and Techstars. My last company used pagers for tech support and I really want to do something better than that and VictorOps looks interesting. I’ve got a lot of experience mentoring entrepreneurs, so I’d like to figure out if I can become part of Techstars.”

I categorize this person as a doer. They responded directly to the assignment. I respond by making some introductions with context – usually double opt-in, but not always depending on the level of relevance. Quickly, the person becomes plugged into a few other nodes in the Startup Community and their journey has begun.

The last 25% is amazing. They blow my mind. Their response is something like:

“Brad, thanks for pushing me to be more precise. I realized I didn’t need you to make the intro for me, so I’ve gotten together with Todd Vernon at VictorOps, Nicole Glaros at Techstars, and Ari Newman at Bullet Time Ventures. It looks like there might be a nice fit with Todd’s company and we are exploring a way to work together. Nicole explained to me that there was a very long waiting list of mentors for the next program so the most effective thing I could do is find one of the older Techstars companies and help them out. I’m already talking to the guys from Sphero (which I know you are on the board of) since I have a lot of gaming experience. And, given my previous network management company experience, Ari hooked me up with the Distill Network guys. I hope you don’t mind if I write periodically and follow up with what I’m up to. By the way, I tried out FullContact for Gmail per your blog post and so far it’s working great.”

This person is a leader. They simply went out and did shit. They made it happen. They followed up. They did things that had a potential positive impact on my world. They didn’t ask me for more, but offered up plenty, which makes me want to do more for them.

Remember, these are simple examples. I categorize the responses three ways:

1. 50% of the people vanish
2. 25% of the people do the assignment
3. 25% of the people make shit happen well beyond what the assignment was

The folks who capture my attention and energy going forward are the ones in category 3. The leaders.

Jerry Colonna spent a few hours with me and Amy on Saturday at our house. Jerry is one of our closest friends on this planet so any time we get time with him is a treasure for us. It was a cold-ish, snowy, gloomy Colorado early winter day. Amy and I were pretty off-balance due to my blood clot so it was especially nice to be with him as he always helps rebalance us.

We talked some about his new company Reboot . I’m a huge supporter of Jerry’s work – recommending many of the CEOs we work with to him, or his associates, for coaching. I attended a recent CEO Bootcamp  as a special guest and it was amazing – I recommend it to every CEO.

Jerry mentioned that the recent Reboot podcasts were doing great and really fun. I noticed this morning that the podcast he did with Rand Fishkin, another close friend, titled #7 Depression and Entrepreneurship – With Jerry Colonna and Rand Fishkin , came out today. So I read the transcript (I can read a lot faster than I can list) and thought it was dynamite.

As usual, Jerry goes deep and intimate – very quickly. So does Rand – total, extreme, full transparency. Enjoy!

In a recent board meeting, at a particularly challenging part of the conversation, I did a retrospective of the past five years as a lead up to making a point. I prefaced it by saying “I need you to take a leader approach, not a victim approach.” I realized no one knew that I meant by this, so I told a quick story, which I first heard from Jeremy Bloom, the CEO of Integrate , retired pro-football player, retired Olympic skier, and someone I adore.

Jeremy’s summary is :

“I’ve learned that there are two types of people: leaders and victims. Leaders are those who see a complex problem and figure out a way either individually or collectively to solve it. These are the people who build successful businesses, become C-Level execs and start their own companies. Victims look at problems and instantly blame everyone else when they can’t solve it. They are the finger-pointers and can rarely admit when they make mistakes. I’ve seen firsthand in football and business how victims can bring down the morale of an entire team. It’s impossible to build anything with a victim mentality.”

In the longer version of the story, he talked about his experience on the Philadelphia Eagles (amazing talent, victim mentality) and the Pittsburgh Steelers (mediocre talent, leader mentality.) He also has a great cross-over line from his experience in athletics to being an entrepreneur:

“My journey in athletics provided me with numerous lessons I apply every day in business. In athletics, for every gold medal that I won I failed 1000 more times. I became conditioned to handle the emotional swings. Possessing the mental ability to stay even keeled during the highs and lows is one of the most important skills one can possess to increase the likelihood of long term success. Any entrepreneur will tell you that there are days when they are 100% confident that they are going to change the world and other days when they aren’t sure if the company will be around in a few months. Managing the emotional swings in business comes easier to me because of my experience in athletics.”

The retrospective with the company was powerful. The company is a real company with significant revenue and over 100 employees. They’ve had numerous challenges along the way, including many disappointments with larger partners who have behaved in ways that could easily cause anyone to be cynical and take a victim approach to the world, as in “we are a victim of the capriciousness and bad behavior of our much larger strategic partner.”

The core of the company is strong. The team, especially the leadership team, is dynamite. The customer base is incredible. The technology and products are very deep. The optimistic view (the leader view) of their prospects is strong. The pessimistic view (the victim view) is one of fatigue and frustration, especially of broken promises of others.

I led with the punchline. The business was profitable in Q3. It was cash flow positive after debt service. The Q4 pipeline is solid. The new product family looks great and is off to a strong start, even though it’s early in the cycle. The broad market for their new product line is exploding. The leadership team is dynamite and very, very tight knit. The employees are smart, committed, and a good mix of long-timers and relatively new folks.

We talked for a while. One of my comments was “Fuck your historical big company partners – you know how they are wired and what their behavior is going to be. Don’t depend on them and don’t worry about them. Work with them in a collaborative, friendly way, but don’t count on them. Be a leader and create your destiny, rather than be a victim to whatever their whims are.”

As I was going through my emails this morning catching up after a long day, I was pondering the tone of entrepreneurs I work closely with, most of whom behave like leaders almost all the time. This is in comparison to a lot of other entrepreneurs I interact with but don’t work with, some who behave like leaders but a surprising numbers who behave like victims. And then I pondered this in the context of my interactions with VCs and co-investors, where again I realized that there is a lot of victim mentality in the mix.

Are you a leader or a victim?

I got to spend a lot of time with my close friend Rand Fishkin the past few days. The first was at Denver Startup Week, where we did a panel discussion with Ben Huh and Bart Lorang where we discussed the pact between CEO and Board, the pact between Founder and Investor, and how to be transparent and direct.

The next day, Rand led a full day offsite for a number of CEOs in our portfolio.

In between, he wrote an epic blog post titled A Long, Ugly Year of Depression That’s Finally Fading . Go read it now – I’ll wait.

I love Rand – not in that surface “I love you man” kind of way. Ever since I met him and his wife Geraldine , I’ve adored them as a couple and each as individuals. I often develop deep personal relationships with the people I work with which can be challenging when businesses struggle and difficult decisions have to be made. I’ve had a few friendships fail as a result of the pressure, stress, and intensity of working through certain situations, but far more have strengthened as a result. It’s a risk I decided to take a long time ago and I’ll continue to do it, even when I have to cope with my own anxiety, emotional struggles, and even depression, as a result.

We invested in Moz in April 2012. Rand wrote so extensively about it in his post Moz’s $18 Million Venture Financing: Our Story, Metrics and Future  that almost all of the major tech blogs declined to write about it “because all the news was covered in the post.” Whatever.

The first nine months were great – the business grew as planned as I started to get to know everyone and how things worked at Moz. The company was working on a major rebrand (from SEOMoz to Moz) as well as a huge software expansion which was started before I invested. But by mid-year 2013 things were not going as planned. Rand has written extensively about it, but when he and Geraldine visited us in Boulder for a few days around that time both Amy and I thought Rand was depressed.

By the winter time, Rand had decided to hand the CEO roles to his longtime partner and COO Sarah Bird . Shortly after, he acknowledged his depression in his post at the end of 2013 when he wrote Can’t Sleep; Caught in The Loop . Regardless of his struggle, he continued to work incredibly hard, but we started having a different conversation, this time as friends rather than investor / board member and CEO / founder. I was more concerned about Rand’s mental health than his activity at Moz, and our conversations were generally around this. At the same time, Sarah grabbed the CEO reins firmly and has done an outstanding job, which I knew would ultimately be helpful to Rand.

Rand looked better in the past few days than I’ve felt he looked in several years. I was thrilled to see his post come out between our rambling Denver Startup Week discussion and the full day of the CEO offsite.

Most of all, I’m delighted that my friend Rand’s depression is finally starting to fade. Rand – you are amazing – and loved by me and many. Carry that with you all the time.

In yesterday’s post Mentors 4/18: Be Direct. Tell The Truth, However Hard , Joah Spearman left a very powerful comment about empathy.

“The older I get the more I realize that truth is something that is best coupled with empathy. Ultimately, you have to seek to understand before you can be understood and part of telling the truth is knowing that you’ll never know someone else’s truth until you hear it directly from them rather than assuming you know what someone has experienced or what’s best for them.”

This made me think of a deeply held belief that I hold with my partners at Foundry Group – brutal honesty delivered kindly.

When I invested in Moz , I thought a lot about TAGFEE , which is Moz’s code that reflects their core values.

Transparent
Authentic
Generous
Fun
Empathetic
Exceptional

I especially keyed in on Transparent, Authentic, and Empathetic as these three are core personal values of mine. However, these three ideas often come into conflict. It’s hard to be transparent and empathetic at the same time. Consider the situation where you fire a person. Legally, you likely have some constraints on what you say, limiting your transparency. You want to be empathetic to the person you fired, so this again limits your transparency (or, if you are transparent, you likely aren’t being very empathetic.) And then, at a meta-level, you will have some internal struggles with your authenticity around this situation.

The tension between the concepts is helpful as it makes you think harder about how you comport yourself is difficult, challenging, or complex situations.

The solution between me, Seth, Jason, and Ryan is to be brutally honest at all times but deliver feedback kindly.

While I’m sure we hold back on occasion, especially when one of us is unclear on what is going on, we subscribe to the notion of brutal honesty. We try hard to be fair witnesses  in the style of my wife Amy, saying what we believe to be the truth. When it’s a hypothesis, we frame it as such. When it’s an assertion, we state that. When it’s something we feel strongly about, we preface it appropriately. And when it’s a fact that we are certain of, we are unambiguous in what we say.

No matter how difficult, sharp, upsetting, or confrontational something is, we always deliver the message kindly. We are not decedents of the Stepford Wives and we each have our own personalities, so “delivered kindly” means something different for each of us. But we never mean malice, harm, or disrespect. We are quick to own our opinions, especially when we are wrong. And when on the receiving end, we listen, and try to understand the other person’s truth, as well as our own, and then reconcile them.

If you sat in a meeting with us, you’d see no yelling. No pounding on the table. No grandstanding. No aggressive body language. No passive aggressive behavior. But you would hear a lot of brutal honesty, And you’ll hear it delivered kindly.

I’ve been thinking about the concept of “the duo” a lot recently.

Many of the companies I’m involved in have either two co-founders or two partners who partner up early in the life of the business. Examples of founding partners including Andrei and Peter (Kato.im ), Keith and Jeff (BigDoor ), James and Eric (Fitbit ), and Matthew and Cashman (Yesware ). Of course there are many other famous founding duos like Steve and Steve (Apple), Jerry and Dave (Yahoo!), Larry and Sergey (Google), and Bill and Paul (Microsoft). My first company (Feld Technologies) had a duo (me and Dave) and the company that bought Feld Technologies did also – Jerry and Len (AmeriData).

But many of the companies I’m involved in have duos that develop over time. Sarah and Rand (Moz ). Bre and Jenny (MakerBot ). Matt and George (Return Path ). David and David (Techstars ).

Now, these duos are not the leadership team. But there is a special magic relationship between the duo. I like to think about it like the final fight scene from Mr. and Mrs. Smith where Brad and Angelina are back to back, spinning around in circles, doing damage to the enemy.

This is not just “I’ve got your back, you’ve got my back.” It’s “we are in this together. All in. For keeps.”

It’s just like my relationship with Amy. We are both all in. It’s so powerful – in good times and in bad times.

I’m on the receiving end of phone calls and video conferences with CEOs all day long. And, at least once a day, I can feel the intense stress on the person I’m talking to oozing through the phone or the screen. The conversation is often calm and rational, but below the surface is a bubbling cauldron of pressure.

Welcome to life as a CEO of a fast growing startup. Every day something new and unexpected comes at you. Often multiple things. Some are awesome. Some are ok. Some are bad. And some are awful.

Ben Horowitz wrote what I think is the best post ever on this called The Struggle . After I read it, I asked him if I could include it in my book Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur . He graciously said yes, so I did.

I felt The Struggle regularly when I was running Feld Technologies in the 1980s. I put myself at a disadvantage – when something went wrong people often called for “Mr. Feld.” My partner Dave carried a lot of the burden as well so I wasn’t alone, but I was on the receiving end of a lot of unhappiness over the years.

While I got better at compartmentalizing it, I never mastered it. I still struggle with it today. I can absorb an enormous amount of stress from the CEOs I work with. But sometimes I get overloaded and end up far out on a deep tree limb trembling with anxiety. I like to refer to this as “inappropriate anxiety” because I know exactly what is at the root cause, but my obsessive mind has a difficult time letting it go.

So I do what I can. I talk to Amy. I walk Brooks the Wonder Dog. I take a bath. I try to sleep a little more. I run more. I let the obsessive thoughts roll around in my head, chasing each other like characters from SpongeBob SquarePants.

And sometimes I just go in a closet and scream for a little while. I let all the bad energy out. I put my all into it – expelling the stress. Trying to reset my mind. Knowing that the inappropriate anxiety will go away and I’ll feel ok again.

When I hear this in the voice of a CEO I’m working with, I offer up myself as a release valve. While I don’t invite it, I want them to know they can vent to me. That they can bare their soul safely to me. That I won’t judge them on the pressure they are under. That I won’t try to solve the problem for them.

But that I’ll be there.

And I let them scream if they want to.

It’s really hard to be a CEO. Becoming a great CEO takes a lot of time, work, focus, coaching, and introspection.

My very close friend Jerry Colonna is hosting his second CEO Bootcamp from April 2 – April 6. Several CEOs from the Foundry Group portfolio went last year and each had an amazing time. This year I’m going to be attending as a special guest and participating throughout the four day program.

I’ve learned an enormous about from Jerry over the past 20 years.  We first met in 1994 when I was a chairman of NetGenesis. Jerry had recently invested in a company called eShare, which ended up buying a product called net.Thread (one of the first, if not the first, threaded discussion group system – which was written in Perl) from NetGenesis. I joined the eShare board as part of the deal and a very deep friendship and working relationship ensued.

When Jerry told me about the first CEO Bootcamp a year ago I encouraged a number of CEOs in our portfolio to attend. Each one came back saying some version of “it changed my life”, which wasn’t really a surprise to me knowing Jerry but was a strong positive affirmation of the experience.

This year, when Jerry told me the dates for CEO Bootcamp and asked me to spread the word, I asked if I could come and participate. It’s in Colorado at an awesome place called Devil’s Thumb Ranch so I can drive to it and is a topic that’s front of mind for me given my relationship with the various CEOs in our portfolio.

I try hard to develop a deep personal relationship with the CEOs I work with. I’ve written in the past about Being Vulnerable and think it’s one of the most important qualities of a leader. As Jerry says so well in the overview of the requirements for attendees, “you may be tired, but you must be vulnerable, curious and courageous.” The full list of requirements follows:

• You’re the CEO of a tech start­up that has employees.

• This is the first time you have been a CEO within a company of this scale.

• You’ve logged immeasurable hours and have made tremendous sacrifices.

• You’ve had success with your company. You realize there is more to this game than “success.”

• You may be tired, but you must be vulnerable, curious and courageous.

I’m planning on participating in the entire event. The agenda is still being finalized, but the current plan is for me to do a joint talk with Jerry on Friday, fireside chats with Jerry on Friday and Saturday, and hikes after the main sessions.

I know two of Jerry’s three partners in this endeavor and think Sam Elmore and Ali Schultz are dynamite. To be clear, I’m volunteering my time and participating – this is Jerry, Sam, Ali, and Michael’s gig so I’m going to do whatever they want me to – or not to – do.

Registration is open until 2/9/14 at midnight MST. 20 CEOs will be accepted. I hope to see you there.