Brad Feld

Tag: ceo

One of my favorite books of all times is Zen and the Art of Motorcycle Maintenance. I read it every few years and recommend that every entrepreneur read it early in their journey.

While a plethora of entrepreneurship books have come out recently, including the ones I’ve written in the Startup Revolution series, there hasn’t yet been the equivalent of Zen and the Art of Motorcycle Maintenance for entrepreneurship.

Matt Blumberg’s new book –Startup CEO: A Field Guide to Scaling Up Your Business – has elements of it and is awesome. It should be out next month and every entrepreneurial CEO should buy a copy of it right now as it’ll be an incredibly important book to read for any CEO at any experience level.

Riz Virk’s post on TechCrunch yesterday – The Zen of Entrepreneurship – also caught my eye. He’s got a book out called Zen Entrepreneurship: Walking the Path of the Career Warrior. He’s sending me a copy but I went ahead and grabbed it on Amazon to read this weekend.

I know Riz from the 1990’s in Boston – I was an advisor to his first company Brainstorm Technologies. It was long ago enough at this point that I don’t know if I was helpful or not, but I had warm feelings toward Riz and smiled when I saw his name pop up again after not seeing it for a while.

Jerry Colonna and I have talked on and off about really digging into this topic and trying to write a philosophical treatise on entrepreneurship and the entrepreneurial way that will stand the test of time. I’m not ready to take this on as I’ve got enough on my plate, but I know it’s out there somewhere. In the mean time, I’m psyched to see more CEOs writing real books about entrepreneurship, rather than yet another ego testament to themselves.

Matt and Riz – thanks for putting the effort into this!


Our Foundry Group CEO list lit up this morning with a question about CEO coaches and whether they were helpful.

My quick response was:

I think a great CEO coach can be awesome and not-great CEO coach can be very detrimental. Jerry Colonna is the best CEO coach I’ve ever met or worked with. There are others that I’m sure will emerge from this discussion but make sure you know what you are getting / looking for.

Like many of our CEO threads this one filled up quickly with great thoughts and suggestions. Then one just nailed it.

“The key for me is that it was a cross between coaching and therapy. You can talk about business issues *in the context* of how you feel about them. This is a crucial benefit, because no matter how good your relationship with board members, expressing those feelings necessarily affects the business conversation; and no matter how astute your spouse, he or she is likely not to put enough weight on the business considerations. Consequently, the normal mode for a CEO is to have all of it in your head; and sometimes it just rolls around in there and makes you crazy.

I suspect this is true no matter how “transparent” you are.

Consequently, the key for a CEO coach is that they be able to quickly understand the business issues AND the emotional issues, and tie them together.”

CEO coaches aren’t for everyone, but I’ve seen amazing impact when a CEO gets a match with a coach that fits well with what he/she needs. And I’ve also seen the opposite – total mismatches between coach and CEO that drove the CEO over a cliff. Make sure you know what you are looking for, and assess regularly what you are getting from the relationship. But don’t be afraid to try.


Rajat Bhargava and I have been working together since 1994. We’ve been involved in creating seven companies together (the most recent ones are MobileDay and Yesware) and, while most have been successful, we’ve had a huge number of positive and negative experiences along the way. We’ve mostly had a lot of fun and, when we haven’t, we always made sure we figured out what went wrong.

 just put up an interview with us on the Inc. Magazine site titled 4 Signs You Should Say ‘No’ to a VC which I thought was excellent. She explores the entrepreneur – VC relationship and suggests four warning signs for an entrepreneur when interacting with a VC.

  1. The VC isn’t fascinated with your product
  2. He (or she)’s just not that into you
  3. You can’t be completely honest
  4. The VC doesn’t treat you like an equal

The paragraph on “you can’t be completely honest” is a seminal moment in my relationship with Raj. It also was a key point in my work career where, upon reflection, I completely and totally grokked the importance of being honest in the moment, clear about my reasoning, and willing to change my perspective based on new information, rather than feeling stuck in simply delivering a message. The section from the article follows:

“The important thing is to be completely transparent,” Bhargava says. “It’s very, very difficult to be transparent about your business, but it goes a long way toward building that relationship. ‘Here’s what I’m going through; here’s what I’m struggling with; here’s what I need help with.’ You have to know if that will spook the investor or if they’ll want to dig in and help you.”

That ability to be honest was a great asset in Feld and Bhargava’s relationship when they worked together on Interliant, the only one of their ventures that did not survive. After some politicking by a different executive, Feld removed a part of the company’s operations from Bhargava’s oversight. Bhargava took a few days to calm down, but then he explained forthrightly how disappointed he was and why he believed Feld had made the wrong decision. “Being open and directly confronting the issues, you get through it,” Bhargava says now. “I felt hurt, but I think our relationship is that much stronger.”

As for Feld, he recalls returning to his hotel after discussing the matter over dinner and feeling physically ill. “I knew I had completely screwed up,” he says.

I count Raj as one of my closest friends and trust him with my life. He’s had an enormous influence on how I behave as an investor and how I interact with entrepreneurs. Raj – thanks man – I look forward to many more years working together.


This week I had two meetings with CEOs of companies we’ve recently invested in where the question of “what is an ideal board meeting” came up. I’m writing an entire book on it called Startup Boards: Reinventing the Board of Directors to Better Support the Entrepreneur so it’s easy for me to define my ideal board meeting at this point since my head is pretty deep into it intellectually.

One of the things I always suggest to CEOs is that they be an outside director for one company that is not their own. I don’t care how big or small the company is, whether or not I have an involvement in the company, or if the CEO knows the entrepreneurs involved. I’m much more interested in the CEO having the experience of being a board member for someone else’s company.

Being CEO of a fast growing startup is a tough job. There are awesome days, dismal days, and lots of in-between days. I’ve never been in a startup that was a straight line of progress over time and I’ve never worked with a CEO who didn’t regularly learn new things, have stuff not work, and go through stretches of huge uncertainty and struggle.

Given that I am no longer a CEO (although I was once – for seven years) I don’t feel the pressure of being CEO. As a result I’ve spent a lot of the past 17 years being able to provide perspective for the CEOs I work with. Even when I’m deeply invested in the company, I can be emotionally and functionally detached from the pressure and dynamics of what the CEO is going through on a daily basis while still understanding the issues since I’ve had the experience.

Now, imagine you are a CEO of a fast growing startup. Wouldn’t it be awesome to be able to spend a small amount of your time in that same emotional and functional detachment for someone else’s company? Not only would it stretch some new muscles for you, it’d give you a much broader perspective on how “the job of a CEO” works. You might have new empathy for a CEO, which could include self-empathy (since you are also a CEO) – which is a tough concept for some, but is fundamentally about understanding yourself better, especially when you are under emotional distress of some sort. You’d have empathy for other board members and would either appreciate your own board members more, or learn tools and approaches to develop a more effective relationship with them, or decide you need different ones.

There are lots of other subtle benefits. You’ll extend your network. You’ll view a company from a different vantage point. You’ll be on the other side of the financing discussions (a board member, rather than the CEO). You’ll understand “fiduciary responsibility” more deeply. You’ll have a peer relationship with another CEO that you have a vested interest in that crosses over to a board – CEO relationship. You’ll get exposed to new management styles. You’ll experience different conflicts that you won’t have the same type of pressure from. The list goes on and on.

I usually recommend only one outside board. Not two, not three – just one. Any more than one is too many – as an active CEO you just won’t have time to be serious and deliberate about it. While you might feel like you have capacity for more, your company needs your attention first. There are exceptions, especially with serial entrepreneurs who have a unique relationship with an investor where it’s a deeper, collaborative relationship across multiple companies (I have a few of these), but generally one is plenty.

I don’t count non-profit boards in this mix. Do as much non-profit stuff as you want. The dynamics, incentives, motivations, and things you’ll learn and experience are totally different. That’s not what this is about.

If you are a CEO of a startup company and you aren’t on one other board as an outside director, think hard about doing it. And, if you are in my world and aren’t on an outside board, holler if you want my help getting you connected up with some folks.


tl;dr – Yes.

I’m on the all@company.com list for a number of the companies I’m on the board of. CEOs and entrepreneurs who practice TAGFEE welcome this. I haven’t universally asked for inclusion on this list mostly because I hadn’t really thought hard about it until recently. But I will now and going forward, although I’ll leave it up to the CEO as to whether or not to include me.

In an effort to better figure out the startup board dynamic, I’ve been thinking a lot about the concept of continual communication with board members. The companies I feel most involved in are ones in which I have continual communication and involvement with the company. This isn’t just limited to the CEO, but to all members of the management team and often many other people in the company. Working relationships as well as friendships develop through the interactions.

Instead of being a board member with his arms crossed who shows up at a board meeting every four to eight weeks to ask a bunch on knuckleheaded questions in reaction to what is being presented, I generally know a wide range of what is going on in the companies I’m on the board of. Sure – there are lots of pockets of information I don’t know, but because I’m in the flow of communication, I can easily engage in any topic going on in the company. In addition to being up to speed (or getting up to speed on any issue faster), I have much deeper functional context, as well as emotional context, about what is going on, who is impacted, and what the core issue is.

Every company I’m involved in has a unique culture. Aspects of the culture get played out every day on the all@company.com email list. Sometimes the list is filled with the mundane rhythms of a company (“I’m sick today – not coming in”; “Please don’t forget to put the dishes in the dishwasher.”) Other times it’s filled with celebration (“GONG: Just Closed A Deal With Customer Name.”) Occasionally it’s filled with heartbreak (“Person X just was diagnosed with cancer.”) Yet other times it is a coordination mechanism (“Lunch is at 12:30 at Hapa Sushi.”) And, of course, it’s often filled with substance about a new customer, new product, issue on tech support, competitive threat, or whatever is currently on the CEO’s mind.

As a board member, being on this list makes me feel much more like part of the team. I strongly believe that board members of early stage companies should be active – and supportive – participants. My deep personal philosophy is that as long as I support the CEO, my job is to do whatever the CEO wants me to do to help the company succeed. Having more context, being part of the team, and being in the flow of the all@company.com communication helps immensely with that.

There are three resistance points I commonly hear to this:

1. “I don’t want to overwhelm my board members with emails.” That’s my problem, not yours, and the reason filters were created for people who can’t handle a steady volume of email. If you are a Gmail user, or have conversation view turned on in Outlook, it’s totally mangeable since all the messages thread up into a single conversation. So – don’t worry about me. If your board member says “too much info, please don’t include me”, ponder what he’s really saying and how to best engage him in continuous communication.

2.”I don’t want my board members to see all the things going on in the company.” That’s not very TAGFEE so the next time you say “I try to be transparent and open with my investors”, do a reality check on what you actually mean. Remember, the simplest way not to get tangled up in communication is just to be blunt, open, and honest all the time – that way you never have to figure out what you said. If you don’t believe your board members are mature enough to engage in this level of interaction on a continual basis, reconsider whether they should be on your board.

3. “I’m afraid it will stifle communication within the company.” If this is the case, reconsider your relationship between your board members and your company. Are you anthropomorphizing your board? Are you shifting blame, or responsibility to them (as in “the board made me do this?”) Are you creating, or do you have, a contentious relationship between your team and the board? All of these things are problems and lead to ineffective board / company / CEO interactions so use that as a signal that something is wrong in relationship.

Notice that I didn’t say “all investors” – I explicitly said board members. As in my post recently about board observers, I believe that board members have a very specific responsibility to the company that is unique and not shared by “board observers” or other investors. There are plenty of other communication mechanisms for these folks. But, for board members, add them to you all@company.com list today.


I get to work with a lot of great CEOs. When I reflect on what makes them great, one thing sticks out – they are always building their muscles. All of them.

As a marathon runner, I’ve got massive legs. Marathoner legs. They’ll look familiar to anyone who runs a lot. In contrast, I have a wimpy upper body. I’ve never enjoyed lifting weights. So I don’t spend any time on it.

Dumb.

I’d be a much better marathon runner if I worked on a bunch of other muscles as well. I’m starting to get into a swimming regimen, I’m riding my new bike around town and this summer I’ve got pilates three days a week as a goal of making it a habit. By the end of summer I hope to have a bunch of other muscles developing and a set of habits that enables me to finally maintain them.

The key phrase above is “I’ve never enjoyed lifting weights.” When asked, I say I’m bad at it. Or that I simply don’t like it. Or, when I’m feeling punchy, that jews don’t lift weights.

Of course, these are just excuses for not working on another set of muscles. If I don’t like lifting weights, surely there are things I like doing instead. I’ve always been a good swimmer – why don’t I have the discipline to go to the pool three days a week and swim? Most hotels I stay in have a swimming pool or have a health club nearby. Swimming is as easy as running – you just get in the pool and go.

“I’m bad at it and I don’t like it.” That’s what runs through my head when I lift weights. For a while, I used this narrative with swimming. But when I really think about swimming, the narrative should be “I’m ok at it and I like it.”

So why don’t I do it? I don’t really know, but I think it’s because the particular muscles I use when I swim are intellectually linked to the weight lifting muscles, which gets me into a loop of “I’m bad at it and I don’t like it.” So rather than break the cycle, I let my muscles atrophy.

Yoga is the same way. I struggle with Ashtanga Vinyasa Yoga. It’s too fast for me, I struggle to remember the poses, and my glasses constantly fall off, and I can’t follow what’s going on. So I say “I’m bad at it and I don’t like it” and then don’t do it. But I do like Bikram Yoga. It’s slower, there are the same 26 poses, and I like the heat. So why don’t I do it? Once again, the narrative gets confused in my mind and it turns into “I don’t like yoga.”

All of this is incredibly self-limiting. Rather than fight with “I’m bad at it and I don’t like it” how about changing it to “I’m not good at it but I’m going to try new approaches and find something I like.” There are many different approaches to building a particular muscle so rather than use a one-size fits all approach (e.g. I must go lift weights, which I hate), search for a different approach that you like.

If you want to be a great CEO, you need to be constantly building all of your muscles. There are going to be a lot of areas you think you aren’t good at. Rather than avoid them, or decide you don’t like them, figure out another way to work on these muscles. You’ll be a better, and much more effective CEO as a result.


I had two similar experiences last week where I heard from employees of two different companies that I’m on the board of. In each case, a senior exec said something like “I heard the board wants us to do blah.”

I was in each board meeting and the board most definitely did not say “we want the company to do blah.” Rather, in each case there was a discussion about the topic in question. In one of the cases consensus was reached quickly; in the other there was a robust discussion since two of the board members disagreed and the CEO wasn’t sure what he wanted to do. Ultimately in that case as well there was consensus.

In each case I asked the executive what he’d heard back from the CEO. I got two versions of “the board had a discussion, there was a lot of disagreement, but the board wanted us to do blah.” I then asked, as non-politically as I could, “Do you think CEO wants to do that?” In both cases, the answer was “I’m not sure, but he knows the board wants that.”

I think this is a brutal communication mistake on the part of each of the CEOs. I’ve seen this many times over the past sixteen years since I stopped being a CEO and started being a board member. In each case the CEO is abdicating some responsibility for the decision. In the worst situation, the CEO is blaming the board for a decision and ultimately setting up a very negative context if the decision is an incorrect one – as in “see – I didn’t want to do this but the board did – so it’s not my fault.”

I’ve come to believe that the only real operating decision that a board makes is to fire the CEO. Sure, the board – and individual board members – are often involved in many operational decisions, but the ultimate decision is (and should be) the CEO’s. If the CEO is not in a position to be the ultimate decision maker, he shouldn’t be the CEO. And if board members don’t trust the CEO to make the decision, they should take one of two actions available to them – leave the board or replace the CEO.

In one of the cases, I asked the executive “if I told you the CEO was strongly in favor of the decision, would that impact you.” The response was a simple one: “yes – I’d be much more motivated to make sure we did it right.” I smiled and reinforced that the CEO was in fact supportive, which I think was a relief (and motivator) to this particular executive.

In my leadership experience, people really value when a leader takes responsibility for a decision, even if it turns out to be an incorrect one. CEO’s – don’t be the guy who says “the board made me do it.”


I’ve started a new category on my blog called “Best Practices.” These are going to be posts inspired by my experiences with various companies that I feel are above and beyond the normal activities you’d expect. The first one comes from Matt Blumberg, the CEO of Return Path. Earlier this week the board received an email from him that included the following:

“Although [our CFO] approves my expenses in our accounting system, inspired by Mark Hurd, I decided it would be a good idea to add a level of transparency to you in terms of my expenses.

To that end, I’m doing two things:

  • I’ve asked our auditors to include some analysis/testing of my expenses in this year’s audit
  • Attached, please find a spreadsheet which details all expenses, with a summary tab that has the overall picture and a few explanatory notes

Trash or treasure, as they say, but please feel free to ask any questions or poke any holes you’d like.  I can assure you that I’m pretty disciplined about expenses (both in terms of not being profligate and in terms of not abusing company money for personal use), but I did think it would be good housekeeping for you to have visibility.”

To a person, we responded that while unnecessary, this was a nice gesture of transparency. The spreadsheet that Matt sent around had every expense item he was reimbursed for in the year. The summary was helpful for putting it all in perspective, but I could look and see where (and with whom) Matt ate dinner, which hotels he stayed in, how much he paid for plane flights, and what he charged to the company as miscellaneous expenses.

I thought about it more and decided it was an awesome display of trust. I have immense respect for Matt, his leadership, and his management skills. But more than that, I’d go to the ends of the earth to do anything for him. Unilateral, unexpected gestures like this one just reinforces that for me. So, more than just transparency, this best practice increases the level of trust between a CEO and his board.


For some reason I’ve been doing a lot of interviews lately.  In many of them I get asked similar questions, including the inevitable “what makes a great entrepreneur?”  When I’m on a VC panel, I’m always amused by the answers from my co-panelists as they are usually the same set of “VC cliches” which makes it even more fun when I blurt out my answer.

A complete and total obsession with the product”

The great companies that I’ve been an investor in share a common trait – the founder/CEO is obsessed with the product.  Not interested, not aware of, not familiar with, but obsessed.  Every discussion trends back toward the product.  All of the conversations about customer are really about how the customer uses the product and the value the product brings the customer.  The majority of the early teams are focused entirely on the product, including the non-engineering people.  Product, product, product.

And these CEO’s love to show their product to anyone that will listen.  They don’t explain the company to people with powerpoint slides.  They don’t send out long executive summaries with mocked up screen shots.  They don’t try to engage you in a phone conversation about the great market they are going after.  They start with the product.  And stay with the product.

When I step back and think about what motivates me early in a relationship with an entrepreneur, it’s the product.  I only invest in domains that I know well, so I don’t need fancy market studies (which are always wrong), financial models (which are always wrong), or customer needs analyses (which are always wrong).  I want to play with the product, touch the product, understand the product – and understand where the founder thinks the product is going.

I don’t create products anymore (I invest in companies that create them), but I’m a great alpha tester.  I’ve always been good at this for some reason – bugs just find me.  While my UX design skills are merely adequate, I’ve got a great feel for how to simplify things and make them cleaner.  Plus I’m happy to just grind and grind and grind on the product, offering both detailed and high level feedback indefinitely. 

How a founder/CEO reacts to this speaks volumes to me.  I probably first noticed this when interacting with Dick Costolo at FeedBurner when I first met him.  I am FeedBurner publisher #699 and used it for my blog back when it was “pre-Alpha”.  I had an issue – sent support@feedburner.com a note – and instantly got a reply from Dick.  I had no idea who Dick was, but he helped me and I quickly realized he was the CEO.  Over the next six months we interacted regularly about the product and when he was ready to start fundraising, I quickly made him an offer and we became the lead investor in the round.  My obsession with the product didn’t stop there (as Eric Lunt and many of the other FeedBurner gang can tell you – I still occasionally email SteveO bugs that I find.)

I can give a bunch of other examples like FeedBurner, but I wrap up by saying that I’m just as obsessed with product as the founders.  And – as I realize what results in success in my world, I get even more obsessed.  Plus, I really like to play with software.


Sometimes a person says one sentence that just sticks with you and is so perfect that it defines a whole category of behavior.  Mark Pincus, the CEO of Zynga, riffed on the phrase “be the CEO of your job” in a board meeting a year or so ago.  It stuck with me and I’ve thought about it many times since.

On Sunday, the NY Times did a great “Corner Office” interview with Mark titled Are You a C.E.O. of Something?  Among other things it explored the idea of being the CEO of your job.  Fred Wilson – also an investor in Zynga – wrote a post on Sunday titled Empowering Your Team which talks about one aspect of this.  But Fred left out a great example from one of Mark’s earlier companies (Support.com) which really nails this concept.

“We had this really motivated, smart receptionist. She was young. We kept outgrowing our phone systems, and she kept coming back and saying, “Mark, we’ve got to buy a whole new phone system.” And I said: “I don’t want to hear about it. Just buy it. Go figure it out.” She spent a week or two meeting every vendor and figuring it out. She was so motivated by that. I think that was a big lesson for me because what I realized was that if you give people really big jobs to the point that they’re scared, they have way more fun and they improve their game much faster. She ended up running our whole office.”

Think about the conceptual progression.  First, the CEO (Mark) had to have to courage to make the young, motivated, smart receptionist “be the CEO of her job.”  Then, when the problem was put to him (“Mark, we’ve got to buy a whole new phone system”), Mark resisted doing something so many entrepreneurs (and executives, and managers) do – namely to “manage” the problem.  Instead of spending a lot of his time solving the problem, or setting up a committee to spend a month figuring out the phone system, or asking someone more senior to the receptionist to figure it out, he gave her the responsibility of solving the entire problem.  He anointed her “CEO of her job” – as the receptionist, she was the one that felt the most pain from the inadequate phone system and was probably in the best position to figure out a solution.

In this case, the notion of “be the CEO of your job” was in the culture of the organization so the receptionist – who was in Mark’s words young, motivated, and smart – took this seriously, spent real time figuring out the solution, and then solved it.  I’m sure the early culture of Support.com was “don’t spend a lot of money” so the financial constraint, while vague, was probably understood.  While there’s plenty more behind the scenes in the story, the young reception clearly “leveled up” (it’s impossible not to use game-speak when talking about Zynga) and ended up running the whole office.

I work with CEO’s every day.  So I’m naturally wired to encourage them to be CEO of their own job.  While this is pretty meta, it’s an important starting point as I already think this way all the time.  I’m certainly not perfect and have moments where I just jump in and try to solve a specific problem, but most of the time I let the CEO’s be CEO.  However, when I contemplate this, I realize I haven’t done a good job of encouraging the CEO’s to make everyone in their organization CEO of the job.  Some CEO’s do this naturally and – not surprisingly – these are generally the highest achieving companies. 

Pause and ponder the idea.  Assuming you are in an entrepreneurial organization, are you being the CEO of your job?  Is this culturally (and functionally) acceptable?  Do you get rewarded for taking risks and succeeding (or failing) like your CEO does?  If not, would you be more effective if you did? 

Now, if you are the CEO of an entrepreneurial organization, do you encourage everyone in the company to be CEO of their job?  Is this culturally (and functionally) acceptable?  Do they get rewarded for taking risks and succeeding (or failing) like you do?  If not, would they be more effective if they did? 

If you applied the lens of “be the CEO of your job” to you job, would you behave any differently?