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:

One of my favorite Bezo-isms is “Disagree and Commit.” I’ve seen it in articles a handful of times recently as the adulation around Amazon and Bezos’ management reaches a fever pitch.

Notwithstanding the disappointing forecast for Q418, Amazon’s recent operating performance has been spectacular. But, more interesting is that it has been “spectacular at scale” and across a very large and complex business.

While Revenue Growth YOY has been strong,

the real story has been YOY growth in Operating Income.

Those are beautiful numbers. It’s clear that in the past few years the company has turned on the profit machine.

For many years, Amazon (and Bezos) trumpeted their focus on revenue growth. The mantra was “we are reinvesting all of our profits in growth.” This is the same thing most startups say (and most VCs push for) as growth compounds rapidly if you can keep the growth percentage (yup – it’s simple math.) This has been particularly true for B2B SaaS companies, not withstanding the notion of the Rule of 40 for a Healthy SaaS Company.

While growth in revenue is still important, Amazon’s ability to generate this kind of growth on its operating income is a reminder that turning on the profit switch at some point does matter, if only to show how much leverage your operating model has (me thinks Tesla did that in Q318 for the same reason). The AWS numbers are remarkable to me – their YOY growth is 46% and their operating income is about 30%. That’s well above the rule of 40.

I would have loved to be in the meetings during the shift from “grow at all costs” to “keep growing fast, but flip the operating income switch.” There were many moments in time over the past 15+ years where I’m sure this came up. But clearly the focus on this changed in the last few years, and the results are now front and center.

I don’t hold any Amazon stock directly, nor do I play the stock market, but the financials in public companies have a myriad of lessons buried in them for private companies that are scaling. That said, the management lessons buried underneath the numbers are even more important. “Disagree and commit” seems to be working well these days for Amazon.

I recently heard the line “sandpaper only works if it is rubbing against something” and loved it.

From Wikipedia: “The first recorded instance of sandpaper was in 1st-century China when crushed shells, seeds, and sand were bonded to parchment using natural gum. Shark skin (placoid scales) has also been used as an abrasive and the rough scales of the living fossil, Coelacanth are used for the same purpose by the natives of Comoros. Boiled and dried, the rough horsetail plant is used in Japan as a traditional polishing material, finer than sandpaper. Glass paper was manufactured in London in 1833 by John Oakey, whose company had developed new adhesive techniques and processes, enabling mass production. Glass frit has sharp-edged particles and cuts well whereas sand grains are smoothed down and do not work well as an abrasive. Cheap sandpaper was often passed off as glass paper; Stalker and Parker cautioned against it in A Treatise of Japaning and Varnishing published in 1688. In 1921, 3M invented a sandpaper with silicon carbide grit and a waterproof adhesive and backing, known as Wet and dry. This allowed use with water, which would serve as a lubricant to carry away particles that would otherwise clog the grit. Its first application was in automotive paint refinishing.”

Every company I’m involved in has issues. Some are minor. Some are major. Some are easy to fix. Some sneak up on you when everything feels like it’s going great. Some are existential crises. Some just feel like existential crises.

Simply put, Something new is fucked up in my world every day.

That’s just the way companies work. And, as long as the company is still around, no matter what size, or level of success, the dynamic is endless. When you think things are going great, it’s just a signal to pay attention to what is going wrong. While there are lots of issues that are exogenous to you, that you can’t control, or impact, many others are issues on the surface of your company.

Use sandpaper on your company daily. Be gentle with it, but precise.

There’s a magnificent exercise that I like to do for myself on a periodic basis. I’m sure it has a more formal name but I call it “Good Bad Like Dislike.”

I create a two by two matrix that looks like this:

I then go through my calendar for the next few months as a starting point to stimulate things to put in each box. I’m careful not to put specific items in the box, but concepts. For example, “Managing Other People” often ends up in “Bad – Dislike” box when I realize, through my forward calendar review, that I have a set of activities where I’m managing others. Or, instead of Good-Dislike: Company X Board Dinner, I end up writing “Board Dinners” in the Good-Dislike Category.

To be more specific, I deeply dislike managing others. While I might have been good at it a long time ago, and I could also likely be good at it if I worked at it, since it’s in the Dislike category, I don’t want to work on it. In contrast, I like “Leading Other People” and am good at it.

Part two is a personal reflection. Instead of being prompted by my calendar, I sit quietly and think about the things I’m doing that I dislike. I’ll often talk to Amy about this as she knows my Good Bad Like Dislike better than anyone on the planet. This is a particularly hard exercise for me because I often rationalize that I should be doing things in the Dislike category. I often overrate my ability on certain things that I feel that I should be good at, so they land in the Good category instead of the Bad category. Having a Fair Witness in one’s life helps with this.

Part three of the exercise is to take specific action around the high-level categorizations. Since I used my calendar to stimulate the review, I have my next three months in the front of my mind. I can then take specific actions. For example, I systematically decide not to do any board dinners in the future. Or, I change the management structure around the project that I’ve ended up managing so that I’m a participant in the project instead of the manager.

I just did this over the weekend as I was considering what 2018 was going to look like for me. I’m also sneaking up on v52 of myself, so it’s a good time for me to think about these kinds of things.

Mark Cuban had a great line a few weeks ago at the interview I did with him and Charlie Ergen at Denver Startup Week. He said:

“I like to invest in people who reduce stress and avoid people who increase stress.”

As I was dealing with something yesterday, this reappeared in my brain but slightly modified.

“I like to be the person who reduces stress and avoid people who increase stress.”

My world is filled with people who increase stress. It’s particularly true around negotiations, but it is also prevalent in board level interactions, relationships with founders, dynamics with leaders, and everything else that has to do with companies. And this is just in my business world. When you wander into other areas, like politics, news, and even social situations, the level of stress (which often masquerades as drama) is remarkable.

One of my meditation routines from Headspace that I like is on Anxiety. Another favorite is on Stress. In both cases, the goal is not to eliminate anxiety or stress but to acknowledge it and be more effective in interacting with it.

The word I’ve anchored on in the past few years around this is equanimity. It’s at the essence of my own personal approach to things. Given the work and larger world context I live in, I’ve accepted that I can’t eliminate stress. I also can’t avoid it. And, while I can avoid people who increase stress, they will still appear and I will need to interact with them.

So, by turning an element of this around 180 degrees, I’ve been able to change my relationship with stress. I accept that stress is everywhere. I don’t try to eliminate it. However, through my behavior, I try to be the person who reduces it. I do this through my approach to all things, carrying the notion of equanimity as a core principle.

This doesn’t mean I’m perfect. I know I generate stress for others in some situations. I know I can always get better at this. Whenever I realize I’ve created stress for someone else, I try to learn from it and improve.

On Tuesday, Jerry Colonna and I had a fireside chat hosted by the Blackstone Entrepreneurs Network titled Making Mental Health a Priority. We did it at DU in partnership with Project X-ITE and had a powerful afternoon.

Last night I had dinner with a CEO I like a lot where we talked about some of the things he was struggling with. I used a concept with him that I’d been mulling about and tried out publicly at the event with Jerry.

I call it the responsibility glitch.

It’s a glitch I’ve had, and have struggled with, since I was a teenager. It’s also a glitch I see in many founders and CEOs.

I started my first company when I was 19 years old. By that point I felt immense responsibility for what I did. I was at MIT working hard on school. I had spent the previous two years – part time during the school year and full time in the summer – writing software for a company called PetCom. One of the products I wrote for them (PCEconomics) was very popular in the oil and gas industry and sold a lot of copies. I got a 5% royalty on every copy sold so I was getting monthly royalty checks ranging from $1,000 to $10,000 (I think the largest one I got was just over $12,000.) I had a long distance relationship with my high school girlfriend who became my first wife. I was the treasurer of my fraternity. While I had an adequate amount of fun in college, I was very serious. And responsible.

As I drifted into my 20s, as my first business grew, I felt responsible for many things around it. I got married and felt responsible for the relationship, my wife, and her actions. I was in a Ph.D. program and felt responsible for the work I was doing there.

At some point, the glitch appeared. It was likely stimulated by a variety of things, including too much overall feeling of responsibility and no perspective on how to manage or modulate it. I had clinical OCD (although I didn’t know it at the time) and had a need to try to control everything in my environment, although my attempts to do this were often hugely irrational and often entertaining to others. For example, I came up with the notion that if every cigarette butt that I passed on the sidewalks in Massachusetts wasn’t parallel to the street then my mother would die. While I clearly had plenty of spare cycles in my brain to ponder stuff like this, the image of me wandering down the sidewalk straightening cigarettes with my sneakers still causes me to cringe even 30 years later.

Then my circuits overloaded. I got kicked out of the Ph.D. program. My wife had an affair and we ended up getting divorced. My business was fine, but the stress from it, and everything else around me was overwhelming. I suddenly started feeling responsible for things I had no business feeling responsible for. I worried about my ex-Ph.D. colleagues, how they were doing, and wondered what I could do to help them avoid my fate. I was empathetic to my ex-wife when she called to ask for help when she was having problems with her boyfriend. I felt responsible for every client we had and whatever flaws were in our software and every moment.

I felt too responsible.

This eventually overwhelmed me and was part of what trigged my first depressive episode which lasted two years. Fortunately I was in therapy so I had a good solid two years to explore the feeling of being deeply depressed and all the elements around it. While there was no joy in that, it was profoundly important to my character and who I am today.

One of the things I learned about myself during this journey was that by being too responsible, I caused a number of unintended negative side effects. Some of these were easy to identify. For example, I learned that I undermined the people working for me since I allowed them to be less responsible, since I’d overcompensate for them. I realized that I was spending a lot of energy trying to control exogenous forces that I had no influence on. As I understood and resolved my OCD, I figured out that I was exhausting part of myself by continually processing a bunch of irrelevant linkages between things that either didn’t need to be controlled, or that I had no ability to impact.

Over the last 25 years, I’ve seen many other founders and CEOs be in the trap of feeling too much responsibility. Their instantiation of this occurs in different ways. There are often elements that are powerful for short moments of time, especially in a crisis. But when the behavior persists, crazy shit starts to happen. Often, feeling too much responsibility is a destructive force to the people around the founder / CEO, the company, the founder / CEO’s family, or the founder / CEO herself.

When I’m sitting with a CEO who feels anxious or self-identifies as depressed, even when she can’t really articulate why or what it means, I often look for the feeling of being overly responsible. It’s common and comes out quickly. When I dig in, I often find the person feels responsible for everyone and everything around her except for herself. She comes last in the list and rarely even gets to herself.

This is the responsibility glitch. If you identify with this, I encourage you to be aware of two things. First, be responsible, but try to stay on the right side of the “too much” line. This is different for everyone, but there definitely is a line where your feeling of responsibility starts to become destructive.

More importantly, be responsible for yourself first. As Jerry likes to say, go on a continuous journey of radical self-inquiry. Understand yourself. Learn about yourself. Take care of yourself. Be responsible for yourself. Only then can you be constructively responsible for others and things around you.

And now it is time to go for a run.

By definition, as a company scales rapidly, it adds people quickly. There are many things about this that are difficult, but a vexing one has to do with the leadership team.

Often times, the wrong people are in senior positions. The faster a company grows, or the less experienced the CEO is (e.g. a first time founding CEO), the more likely it is a problem. Per Fred Wilson’s famous post What A CEO Does, this is one of the three key responsibilities of a CEO.

“A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank.”

I’ve slightly modified in my brain to be that a great CEO has to do three things well. These three things. They can be great at many other things, but if they don’t do these three well, they won’t be successful long term.

Let’s focus on “recruits, hires, and retains the very best talent for the company.” This is where the vexing part comes in. As a company grows from 25 to 50 to 100 to 200 to 500 to 1000 people, the characteristics of who is the very best talent in leadership roles will change. It’s rarely the case that your leadership team at 1000 people is the same leadership team you had a 25 people. However, the CEO is often the same person, especially if it’s a founder.

Stress on fast growing companies comes from a lot of different places. The one that is often the largest, and creates the most second order issues, is the composition of the leadership team. More specifically, it’s specific people on the leadership who don’t have the scale experience their role requires at a particular moment in time.

Take a simple example. Imagine a 50 person company. Now, consider a VP Engineering who has never worked in a company smaller than 5,000 people. His last job was VP Engineering on top of a division representing 25% of the development resources of a very large company, reporting up to the division president. By definition he has never worked in a company that grew from 50 people to 100 people in a 12-month period. He might argue that he’s seen that kind of growth within a segment of the company, but he’s never experienced it working directly for a CEO of a small, rapidly growing company.

In comparison, consider a VP of Engineering who has worked in three different  companies. She started with one that grew from 20 to 200 and was acquired. The next one grew from 5 to 100 and then shrunk again to 10 before being acquired. The one you are recruiting her from grew from 100 to 1000 while she was in the role and is still going, but she’s now tired of the larger company dynamic and wants to get back to a smaller, fast growing company.

Which one sounds like a better fit? I hope you chose the second one – she’s a much better fit in my book.

Now, here’s the magic trick – if you are a CEO who is interviewing for a new member of your leadership team, ask the person you are interviewing if they have every been in the same role as a company that grew from size -50% to +200% of yours. So if you are the CEO of the 50 person company, you are looking for someone who has been in at least one company that grew from 25 to 100 people. Ideally, they participated in growth to a much larger scale, but at a minimum they should bracket these numbers.

Now, ask her to tell you the story of the company, the growth experience, how she built and managed her team, and how she interacted with the rest of the team. Keep digging into the dynamics she had with the CEO, with other executives, and with the people who worked for her. Focus a lot on a size you will be in a year so you know how she’s going to handle what’s in front of her.

Remember – you are looking for competence fit and culture fit. By using this approach, you are exploring both, in your current and near term context.

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.

Jon Hallett, a prolific angel investor and successful entrepreneur who I’ve gotten to know over the past few years, dropped a major knowledge bomb on me yesterday afternoon when he sent me a post from David Politis titled This is How You Revolutionize the Way Your Team Works Together… And All It Takes is 15 Minutes.

I remember having a meal in December 2011 with David at the Plaza Food Hall in New York and talking about BetterCloud which we foolishly passed on investing in. So I wasn’t surprised to have the reaction I had after reading the post, which I said out loud to myself.

“Fucking brilliant!”

The simple idea is to write a user manual about how to work with you. My partner Seth has an email he sends out to companies he joins the board of titled Welcome to Foundry which is a roadmap for working with him, but also reflects how to work with all of us. It’s similar and touches on some of the questions that David addresses in his article, which he based on a presentation from Adam Bryant, a columnist for The New York Times, titled “The CEO’s User Manual.”

In this presentation Adam gave there were two sets of questions to answer to sketch out the User Manual. The first set, focused on the individual person, were:

• What are some honest, unfiltered things about you?
• What drives you nuts?
• What are your quirks?
• How can people earn an extra gold star with you?
• What qualities do you particularly value in people who work with you?
• What are some things that people might misunderstand about you that you should clarify?

The second set are focused on how the individual acts with others.

• How do you coach people to do their best work and develop their talents?
• What’s the best way to communicate with you?
• What’s the best way to convince you to do something?
• How do you like to give feedback?
• How do you like to get feedback?

I’m going to do this exercise over the weekend and share with my partners and all of the CEOs I work with to get their feedback on whether (a) it’s helpful and (b) it’s truthful. I’m going to let them give me feedback (which will help me learn myself better). As I iterate through it, I’ll eventually publish it on this blog. And, if the exercise works, I’m going to encourage every leader I work with to consider doing it.

After skimming the New York Times this morning (while Amy reads it word by word), I felt like a philosophical dump. Maybe it was the article on why Trump is so popular. Or the completely banal business section where everyone knows what is going on.

Confidence is an attribute that humans value. We like and are attracted to confident people.

Competence is an attribute that we also value. But it’s often more subtle and harder to determine, especially on a first interaction.

Over a long period of time, I’ve come to realize that a balance between confidence and competence is very appealing to me. I’m attracted to people who know what they know and know what they don’t know. These people are constantly learning and their competence around a particular topic increases linearly with their confidence.

Recently, I realized that we refer to people as over-confident or under-confident, but rarely refer to people as over-competent or under-competent. We do refer to people as clueless, ignorant, stupid, and other things that imply under-competent, but often in the context of their level of confidence. I don’t really know of a phrase we use for over-competent.

In an era where everyone is an expert, the ratio between these two concepts strikes me as particularly compelling. Lets define cluefulness (CLUE) as:

CLUE = confidence / competence

CLUE = 1 is ideal. If CLUE > 1 then you’ve got an over-confident person. If CLUE < 1 then you’ve got an under-confident person. But interpreting this on the under-confident / over-confident spectrum doesn’t really tell you much. Is the person a blowhard, or are they shy? Are they bombastic, or just quiet power? Are they an extrovert or an introvert? Are they full of shit, or just unconcerned with whether you realize how competent they are.

I’m attracted to people with CLUE <= 1. And I find people with CLUE > 1, especially by a significant amount, insufferable.

Do I have a CLUE about this? Feel free to help me get my ratio in balance.

This is one of my favorite lines to use to explain the business life I live. When asked what it’s like to be a partner in a VC firm, be on a bunch of boards, and have a continuous stream of random interaction come my way, I like to level set my reality.

It’s simple. Something new is fucked up in my world every day.

Now, just because something new is fucked up, doesn’t mean I’m unhappy. Quite the opposite – I’m usually happy, although when the pile of fuckedupness gets high enough I get tired. And day after day after day of 12+ hour days also make me tired. I used to be able to work through the weekends – now at 49 years old I need them to recover, get patched up by Amy, and get ready to go back out there.

Jerry Colonna at Reboot.io tells a wonderful story about the crucible of leadership on Fred Wilson’s blog with a section titled Eat Me If You Wish (read the whole post but the parable is about half way through.) It’s worth repeating here. Take your time reading it.

“One day,” begins a story re-told by Aura Glaser in the latest issue of Tricycle Magazine, “[the Buddhist saint] Milarepa left his cave to gather firewood, and when he returned he found that his cave had been taken over by demons. There were demons everywhere! His first thought upon seeing them was, ‘I have got to get rid of them!’ He lunges toward them, chasing after them, trying forcefully to get them out of his cave. But the demons are completely unfazed. In fact, the more he chases them, the more comfortable and settled-in they seem to be. Realizing that his efforts to run them out have failed miserably, Milarepa opts for a new approach and decides to teach them the dharma.

“If chasing them out won’t work, then maybe hearing the teachings will change their minds and get them to go. So he takes his seat and begins… After a while he looks around and realizes all the demons are still there…At this point Milarepa lets out a deep breath of surrender, knowing now that these demons will not be manipulated into leaving and that maybe he has something to learn from them. He looks deeply into the eyes of each demon and bows, saying, ‘It looks like we’re going to be here together. I open myself to whatever you have to teach me.’

“In that moment all the demons but one disappear. One huge and especially fierce demon, with flaring nostrils and dripping fangs, is still there. So Milarepa lets go even further. Stepping over to the largest demon, he offers himself completely, holding nothing back. ‘Eat me if you wish.’ He places his head in the demon’s mouth, and at that moment the largest demon bows low and dissolves into space.”

I put my head in a demon’s mouth every single day. Often, it’s a different, or new, demon. Sometimes it takes me a few days to get ready for this so the demons back up. Other days two or three new demons appear and I can only deal with one of them so the others hang around.

I learned how to deal with this in 2001. That year started out miserable with companies I was involved failing all around me. I did everything I knew how to do to help. I’d go to bed at the end of the day thinking, “Ok, that totally sucked, but tomorrow will be better.” It wasn’t – each day was worse. By about June I realized that every single day of 2001 had been worse than the previous day. I finally metaphorically threw up my hands and internally said, “Fuck it, let’s see what the world can bring on today.” That’s when I started to sit with the demons.

Up to that point, I was fearful of what the day would bring. I would fight against it. I would thrash around looking to solve every problem, chasing the demons around my cave trying to get them to leave. And then 9/11 happened, on a beautiful morning in New York, while I was fast asleep in a hotel room in midtown Manhatten at The Benjamin Hotel after taking a redeye from San Francisco. As the planes crashed into the World Trade Center towers, Amy frantically called me from the road as she was driving to the airport to come visit me in New York. I had turned off my phone so I expect I snored happily away as the first tower fell. When I finally woke up I to whatever station the clock radio was on, I thought it was all a joke. For about a minute, I struggled through the post redeye haze that enveloped me, along with the existential fatigue I was feeling from nine months of companies failing everywhere, people being angry, unhappy, depressed, stressed, scared, and under immense pressure, and then I realized it wasn’t a dream.

When I finally woke up enough to turn on my phone and call Amy, I was lucky enough to get through. She pulled over to the side of the road and cried. She was sure I had been on one of the planes that had crashed. After a few minutes, we realized a trip to NY was silly so she turned around and went home. I then took a shower and tried to process what was going on and figure out what to do next.

There’s a lot more from that day that shaped me, like it shaped so many others, but suddenly many of my demons just disappeared and went to torture other people. I realized that as fucked up as my world was, it was trivial compared to what was going on 60 blocks away. While I was terrified and trapped in The Benjamin for a while, I had at least four hours before I took action to just sit and process things.

Dealing with the particular set of demons in my cave at this point to another three months. That period was my second of three clinic depressions that ended around my birthday on December 1st. I spent these three months sitting with all of my demons, welcoming more into my world, and just learning from them.

When the really scary ones showed up, I didn’t fight. I just placed my head gently in each of the scary demons’ mouthes and said “eat me if you wish.”

Just like with Milarepa, it worked. And it’s now how I live every day.

Have you ever finished something and thought to yourself, “That didn’t need to take an hour?”

In my world, I have an endless stream of requests to do something for an hour. I just looked at my calendar for the next two weeks and almost everything that someone else scheduled and invited me to is for an hour.

In contrast, all of the things I (or my assistant) have scheduled are for 30 minutes. And many of them will take five minutes.

If you schedule a meeting for an hour, it’s remarkable to me how often it takes an hour, even when it doesn’t need to. Three hour board meetings, especially when board members have traveled to them, take – wait for the drum roll – three hours.

During the day, between Monday and Friday, I generally have a very scheduled life. I go through phases where I shift into Maker Mode, now no longer schedule anything before 11am my time (with occasional exceptions), and try to have a very unscheduled weekend. But Monday to Friday looks like the following:

Over time, I’ve come up with some approaches to deal with this massively over-scheduled life in order to stay sane. Here are a few of them.

30 minute schedule slots: I’ve tried it all. 60 minutes. 15 minutes. 5 minutes. 45 minutes. 37 minutes. The only thing that I’ve found that works is 30 minutes. If I schedule for 15 minutes, I inevitably have too many things in a day and get completely exhausted. If I schedule for more than 30 minutes, I find myself twiddling my thumbs and trying to get finished with the meeting. 30 minutes seems to be the ideal amount to get any type of meeting done.

A walk: If I have a longer, more thoughtful discussion I want to have with someone, I go for a walk. I have four routes around downtown Boulder – 15, 30, 45, and 60 minute walks. All of these walks have the same loop so even when I schedule for a 60 minute walk, I have an easy way to turn it into a 30 minute walk if it’s clear that’s all it’s going to take. Or, if I’m into the first 15 minutes and realize it needs to be an hour, I just extend to the 30 minute segment. My worst case on a walk that goes too long is that I get some steps for my daily Fitbit habit.

Phone calls: I schedule almost all phone calls, except for ones with high priority people. This high priority ones interrupt whatever I’m doing or get done on a drive to and from the office. If you hang around me, you’ll see that my phone rarely rings (except for Amy) and I rarely make calls outbound as most of my world runs on email or real-time messaging.

End everything early: I try to end everything when it’s done. I jump right in and finish when we are finished. When you give things 30 minutes, you don’t have time to futz around with intros and catch ups. When someone starts this way, I break in and say as politely as I can, “What’s on your mind?” On the phone, I minimize chit chat and just try to get to the point. And, after five minutes when we are done, I revel in the notion that I’ve got 25 minutes to do whatever I want.

I’m always experimenting with new things. What do you do to keep meetings manageable and sane?

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 had a fun email exchange with an investor I’ve worked with for almost 20 years in response to something a CEO send out from a board we are both on. I said “fucking awesome.” He said “that’s an understatement.” I said “CEO is such a delight.” He said “CEO is negative maintenance.”

I loved this. So I’m going to use this post to think through the idea out loud and I’d love your feedback since it’s still a messy / blurry concept in my mind.

My hypothesis is that the opposite of high maintenance is not zero maintenance but rather it’s negative maintenance.

There are days that I’m high maintenance. Everyone is. But if you subscribe to my “give before you get”, or #givefirst, philosophy, you are constantly contributing more than you are consuming. I’ve talked about this often in the context of Startup Communities, but I haven’t really had the right words for this in the context of leadership, management, and employees in a fast growing company.

Suddenly I do. When I think about my role as an investor and board member, I’m often tangled up in complicated situations. I’ve often said that every day something new in my world gets fucked up somewhere. This used to be distressing to me, but after 20 years of it, if I don’t know what the new fucked up thing is by 4pm, I start to get curious about what it’s going to be.

We all know that creating companies from nothing is extremely difficult. The problems that arise come from all angles. Some are exogenous and some are directly under your control. Some are random and some are obvious. Some are compounded by other problems and mistakes, resulting in what my father taught me at a young age was the worst kind of mistake – one that was a mistake compounded on a mistake compounded on a mistake – which he called “a complicated mistake.”

Personally, when I find myself in a complicated mistake, I stop. I step back and pause and reflect. And then I try to figure out how I can change the dynamic into something positive, not continuing to build on my complicated mistake, but instead getting clarity on what the right thing is to do to get out of the ditch.

Negative maintenance people do this. I’ve seen, been involved in, and made some epic mistakes. The CEO I’m referring to above has a great company, but has also experienced some epic mistakes. How he handles them, works through them with his team, and his board, is exemplary. There is work involved by me and the other board members, but it’s not inappropriately emotional. It’s not high maintenance. It’s just work. Decisions have to be made and executed. And there are impacts from these decisions, which lead to more decisions. Ultimately this CEO is putting energy into the system as we work through the issue, which is where the negative maintenance (as opposed to high maintenance) behavior pattern arises.

I like this idea of negative maintenance people. I’m obviously trying to think it through out loud with this post, so weigh in and help me understand it better.

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.

While driving down Highway 36 from Boulder to Denver for a FullContact board meeting, TA McCann told me a wonderful phrase that I’ve been carrying around with me for the past month or so.

“At RivalIQ, we’ve implemented ‘I Will’ instead of ‘We Should.’”

I’ve worked with TA since we invested in Gist in 2009. TA was a co-founder and the CEO. He’s been deeply involved in Techstars Seattle since inception. When RIM acquired Gist, he ran a big software team within RIM for two years. A year ago he co-founded RivalIQ. And last fall he joined the FullContact board. So he’s been around the block.

As part of working together, we’ve become very close friends. We ran the Madison Marathon together (my 17th). We’ve fought together in the trenches over some challenging issues. We’ve enjoyed each others’ friendship, advice, and guidance on some heavy personal issues.

TA embodies the concept of “I will instead of we should.” I’ve always known him to be willing to roll up his sleeves and just get something done. He’s quick to give feedback, challenge ideas, and ask questions, but he’s never afraid to do the work himself.

At Foundry Group, there are twelve of us. I like to believe we embody the “I will” spirit – if someone suggests that something is wrong or needs to be done, they do it. Sure – we pass things around and there’s some delegation, but there’s never a willingness to criticize or give feedback without a corresponding willingness to participate in doing the work.

It’s a small but powerful mental tweak that is similar to the I / We challenge I used to have. In this case it’s the inverse. By shifting to “we” instead of “I” when I talk about what Foundry Group accomplishes, our whole team gets the recognition for the work we’ve all contributed to. This is powerful externally. But internally, by saying “I will” instead of “We should” it puts the responsibility for getting it done on the person making the suggestion. Even if they only manage the work, they are still responsible for making sure it happens, instead of the non-specific and ephemeral “we.”

TA – thanks for the phrase. I continue to learn much from you.

Gluecon’s early bird pricing ends Friday, April 4th and I wanted to make sure you got the chance to register prior to the registration rates going up. When we started Gluecon with Eric Norlin six years ago, I don’t think any of us really had any idea about the true size of the wave of innovation that we were catching. Glue started out like a lot of tech conferences do, with a “business track” and a “technical track,” but we quickly realized what a mistake that was. Since then, Gluecon has transformed into a conference of what I assert is the  deepest technical content available around the topics of cloud computing, mobile, big data, APIs and DevOps. The agenda is shaping up to be something really special. Use “brad12” to take 10% off of the early bird registration. 

One of the things I love best about my Foundry Group partners is that they each have strong opinions. Another thing I love about them is that they each have big open ears.

I know a lot of people who have strong opinions. I know a lot of other people who are excellent listeners. The venn diagram of the intersection of the two is uncomfortably small.

As I’ve written before, I love working with learning machines and silent killers. The best entrepreneurs are the ones who combine these traits.

I know a lot of people with strong opinions who think they are good listeners, but all you need to do is listen to a conversation between them and someone else to watch them talking all over the other person. Or asserting the same point over and over again, often using slightly different language, but not engaging in a process of trying to actually learn from the other person’s response. This is especially vexing to me when the person with strong opinions claims to have heard the other person (as in “I hear you, ok, that makes sense”) but then 24 hours later Mr. Strong Opinion is back on his original opinion with no explanation.

In contrast, I know a lot of strong listeners who won’t express an opinion. The VC archetype that I describe as Mr. Socrates is a classic example of this. I expect most entrepreneurs can give many examples of them being on the receiving end of a stream of questions without any expressed perspective, null hypothesis, or summary of reaction. I hate these types of board meeting discussions – where the VCs just keep asking questions but never actually suggesting anything. There’s not wrong with inquiry and I definitely have my moments of “I don’t get this – I need to ask more questions” but in the absence of a feedback loop in the discussion, it’s very tiresome to me.

Big open ears doesn’t mean that you just listen. It means you are a good listener. An active listener. One who incorporates what he is hearing into the conversation in real time. You are comfortable responding with a modification to an opinion or perspective as a result of new information. You are comfortable challenging, and being challenged, in the goal of getting to a good collaborate answer, rather than just absorbing information but then coming back later as though there was never any information shared.

I’ve always had strong opinions. I can be a loudmouth and occasionally end up in lecture mode where I’m just trying to hammer home my point. My anecdotes and stories often run longer than they should (I blame my father for teaching me this particular “skill.”) But I always try to listen, am always willing to change my opinion based on new data, or explain my position from a different perspective after assimilating new data. When I realize I’m bloviating, I often call myself publicly on it in an effort to shift to listening mode. And I always try to learn from every interaction I have, no matter how satisfying or unenjoyable it is.

Do you have strong opinions AND big open ears?

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 learned a very profound thing from my partner Dave Jilk at Feld Technologies 25 years ago. I have been practicing, and getting better at it, ever since. It’s a core part of the way I work with people and I have Dave to thank for it.

First, some context. Feld Technologies was my first company. Dave and I started it in 1987. We hired, then fired, a bunch of part time people and then just worked together – the two of us – for the next 18 months until we hired our first employee (Shawn Broderick). We were cash flow positive every month because we never raised any outside money. We both did everything, working very closely together. As the company grew, we partitioned a lot of things – I became the sales guy – generating much of our new business. Dave became the software guy, managing the team and getting the work done. But we continued to work closely together – he sold plenty of business and I did plenty of work, including doing all the network integration work for our clients, and occasionally managed something.

We were both young and very inexperienced so we learned a lot together, mostly by screwing things up and then fixing them. Sometimes we had a lot of fun, sometimes we were under tremendous stress, and every now and then one of us was miserable. We were (and continue to be) best friends so when one of us was very unhappy, the other could pick up on the vibe quickly and we talked about it.

I remember a stretch of time where I could tell that Dave was really aggravated with me. This wasn’t uncommon – our love and respect included plenty of “moments” as we were both developing into real adults. But this aggravation seemed deeper and didn’t surface in an obvious way.

I remember taking Dave out to dinner at a sushi place called Nara around the corner from our office at 260 Franklin Street in Boston. I can picture how the night felt – dark and empty with plenty of downtown Boston ambient noise. We went to Nara a lot – this was way before sushi became trendy and it was one of the few places in Boston, located a few blocks away from our office. They had excellent huge bottles of cold beer and amazing fish. And it was always quiet and there was always a booth open.

We sat down, got our beers, and I started with the issue, as I often do.

I asked, “Dave, what’s bugging you so much right now.”
“You.”
“Why? What am I doing that’s bugging you.”
“Working with you is like reading the last page of a novel first.”

I sat nursing my beer for a quiet, long minute pondering this. I mentally read the last page of a novel and thought I knew what Dave meant. Eventually Dave broke the silence.

“When I bring an issue to you, you immediately tell me the answer. 99% of the time you are correct. So I then go spend all of my time looking for a solution that is better that yours. But I only find it 1% of the time. This is incredibly unsatisfying to me.”

I think he may have added something like “fucking demotivating” but by this point I totally groked it. We had an awesome dinner discussing what over the last 25 years we have regularly referred to as “the last page in the book problem.”

Today, I try hard not to start by telling the answer immediately. The CEOs and entrepreneurs I work with need to learn how to get to the answer. And their answer, in many cases, will be better than mine since I don’t have enough context or information to be right 99% of the time like I did when I was the president of Feld Technologies. But even more importantly, a great CEO knows this also. His team doesn’t want to always hear the answer first. Sometimes they do, or need to, but often they want to be able to talk openly, collect data, and come to it over time.

This brief moment has had a profound impact on how I work. While I despise Mr. Socrates (the guy who just asks question after question after question and never expresses a point of view) and don’t emulate him, I definitely ask more “guided questions” when presented with a problem. I tell more stories to try to give examples of how others have solved the problem. And occasionally, when I realize the CEO is asking for the answer (e.g. when Bart Lorang, in the middle of a board meeting, says “Brad, just tell me the fucking answer – I know you know it.”) I tell the answer. But in the back of my mind I always remember that part of learning the answer is figuring out how to find it.

I was fired from my first two jobs. Here’s the story of one of them, which first appeared as part of LinkedIn’s My First Job content package.

“You’re fired.” Those were the last two words I heard from my boss after working for six months at Potatoes, Etc., my first real job. I smirked, immaturely threw my apron at her (I was 15 years old after all), and slammed the door on my way out.

My final three words, preceding hers, were “you’re a bitch.” In hindsight, her response was predictable.

I remember riding my bike home the three miles from Prestonwood Mall where I worked. I had no idea what I was going to tell my parents, but I decided I’d just tell them what happened and see where the chips landed. I felt ashamed of myself for being so disrespectful to my boss, even though she had constantly demeaned me, and all the other people that worked at Potatoes, Etc. I didn’t have any respect for her, but my parents had taught me better and I was proud of my ability to suck it up and not lose my temper.

Potatoes, Etc. was one of those local fast food restaurants in a giant shopping mall from the 1980s. Remember Fast Times at Ridgemont High? Yup – that was us, except Potatoes (as we liked to call it) was staffed by the “honors kids.” I think the Greek souvlaki place was staffed by the jocks and the Corn Dog place was staffed by the stoners, but it all blurs together 30 years later.

In hindsight, the Potatoes, Etc. supply chain was pretty cool. Idaho spuds appeared magically in 50 pounds boxes and ended up in a dank, gross storeroom. Each shift, one person was responsible for getting them, cleaning them, putting them on trays, covering them with industrial grade salad dressing, and racking the trays. Another person was responsible for putting them in the convection oven and making sure there were enough potatoes cooking at all times to handle the spikes in demand. Another person manned “the bar” – cutting open the potatoes and filling them with whatever goop and toppings the customer ordered. And the last person worked the cash register. After we closed, we were all responsible for cleaning up.

Since we were honors kids, we had a lot of fun with the supply chain. We did a good job of load optimization. We figured out process improvements to cut, fill, and serve the potatoes. We ran a parallel process on cleaning and closing up, so we could be done in ten minutes. We were never, ever short on cash.

Our boss was a young woman – probably in her early 20s. I remember the smell of smoke and alcohol on her breath. I remember Saturday morning shifts where she would come in at 1pm, clearly hung over. She liked to yell at us. Her favorite form of managerial shame was to call someone into the back “room” (there was no door) and dress them down randomly so everyone in the food court could hear.

We were good kids. It took a lot to get a rise out of us. Sure – we’d complain to each other about her, but we bonded together and did a good job regardless of her antics. Every now and then she’d do something that she thought was motivating, like bring a case of beer into the back of the store and offer up cans to us (we always declined – remember, we were good kids). But I can’t remember a single time she praised us – or at least me – for anything.

I had been racking potatoes all day on the day I got fired. I was cranky – I wanted to work up front but today wasn’t my day. I was tired – lifting 50 pounds of potatoes and washing them one by one is a drag. And I was bored out of my mind.

My boss probably noticed I was in a bad mood. A kind word from her would have made all the difference in the world. Instead, she came over to the full rack of potatoes, started pulling them off the racks, and without even looking at me dumped them one by one in the sink.

“You suck at washing potatoes.”

“You’re a bitch.”

“You’re fired!”

My parents were gentle with me. They made sure I understood the lessons from the experience, which included the power of respect and not losing your temper with a superior.

But most importantly this was a key moment that I think back to whenever I consider motivation. My boss never did anything to create a context in which we were motivated. It wouldn’t have taken much. And, if she had, respect – and motivation – would have followed. At 15, I learned what it was like to be on the receiving end of a boss who had no idea how to create an environment in which the people that worked for her were motivated. I’ve carried that experience, and the resulting insight, to every subsequent thing I’ve been involved in.