Brad Feld

Tag: management

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.

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 Doesthis 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.