Brad Feld

Tag: ceo

Matt Blumberg’s new book, Startup CEO: A Field Guide to Scaling Up Your Businessis about to come out. If you are a CEO and haven’t preordered it, I recommend you go get it right now.

I had a chat with a CEO I work with who has had a challenging year scaling up his company. He – and the company – have made a lot of progress after hitting a low point this spring. After the call, he sent me the following note he has pasted on his desk.

1. Lead by example by holding myself and all accountable, no matter how hard.

2. Set the overall vision and strategy of the company and communicate it to all stakeholders.

3. Recruit, hire, and retain the very best talent and inspire them.

4. Makes sure there is always enough cash in the bank.

5. Be the advocate for the customer over the company’s short-term needs.

6. Drive the execution and evolve the operating system.

7. Champion the company and our mission to the world.

You might recognize #2, 3, and 4 from Fred Wilson’s magnificent post What A CEO DoesI give a talk for many of the Techstars CEOs called “How to be a Great CEO” and I focus the conversation around Fred’s points. Matt’s book also uses Fred’s three points as a framework. And when I think about how a CEO is doing, I always start with 2, 3, and 4.

I’ve come to believe that you can’t be a great CEO if you don’t do these three things. But, great CEOs do many more than just these three things. So – I view them as “price of admission” – if you can’t / aren’t doing these three things, you won’t be a great CEO.

I always encourage the CEOs I talk with to create a clear framework for what they are doing. What you are doing, and spending time on, will change over time based on the stage of your company. When you are 10 people, you’ll have a different set of priorities then when you are 100, or a 1,000 people. But having a clear framework for what you, and how you do it, is powerful.

I love what this CEO has done to make Fred’s framework his own. Notice that each sentence starts out with the imperative form of an action verb (Amy told me that – doesn’t it sound smart!) – basically a statement of action. Lead, set, recruit, make, be, drive, champion. Great words.

If you break it down, it also defines a value set for the CEO, and for the company.

Finally, you are going to hear a lot more from me about the Company Operation System (what you see in #6). That’s the essence of what Matt Blumberg has figured out in scaling up Return Path, and uses to define his approach to scaling a business in Startup CEO: A Field Guide to Scaling Up Your Business.

My experience with all of this is that it’s incredibly hard, breaks regularly at different points in the life of a company, and requires a great CEO to continually grow and learn from mistakes, adjust course based on new information, and work diligently at being honest with himself, his team, and his board about what is going on. But, if you get it right, it’s magical.


I’m doing a one hour CEO roundtable on an “about weekly basis” with each of the Techstars classes. Yesterday I did a face to face with the Techstars Boulder CEOs (they are across the hall from my office) and then I did my meetings with the Techstars Chicago CEOs and the Kaplan EdTech Accelerator CEOs by video conference.

This is a new experiment for me. I’m trying a different approach to mentoring the Techstars teams this year. I’m still a lead mentor for two of the Boulder teams (Kato and SnowShoe) but for all the other programs, including Boulder, I’m trying a weekly one hour CEO only session.

One of my big goals is to generate more peer interaction between the CEOs of the various companies. We do this aggressively within the Foundry Group portfolio and it’s one of the really powerful things about Techstars. But historically it’s been adhoc and random, rather than in an organized way. This is an effort to get the CEOs to really bond with every one of the other CEOs during the program.

So far the experiment is working great from my perspective. I’m stunned by the depth of the conversation and I can see the relationship dynamics being very broad as well as intellectually and emotionally intense.

Each of the three meetings yesterday were totally different, as Techstars Boulder is in week 8, Techstars Chicago is in week 4, and Kaplan EdTech is in week 2. As I was taking a shower this morning, I kept thinking about the rant I went on during the last 10 minutes of the meeting with the Techstars Chicago CEOs.

By week 4, a team is deep in things. The stress is showing. Everyone is tired and working at their max capacity. They’ve been exposed to a wide range of mentors and lots of conflicting data. Stuff is breaking all the time. Everything is uncomfortable and – in some cases – distressing.

In reaction to a particular conversation, I strung together quotes from three of my favorite books about entrepreneurship. The rant went as follows:

  • It’s not that I don’t suffer, it’s that I know the unimportance of suffering.” – John Galt in Atlas Shrugged
  • Fear is the mind-killer.” – the Bene Gesserit is Dune
  • “Anxiety, the next gumption trap, is sort of the opposite of ego. You’re so sure you’ll do everything wrong you’re afraid to do anything at all.” – Robert Pirsig in Zen and the Art of Motorcycle Maintenance

I used the quotes as the anchors on a longer rant, but I did it extemporaneously. I hadn’t realized how nicely these quotes fit together until this particular moment, prompted by the particular situation. In hindsight, the only quote I forgot was my favorite of all time – “Do or do not, there is no try.” – Yoda.

And – it reminded me that three books should be on every Startup CEO’s reading list along with Matt Blumberg’s new book, Startup CEO.


Pre-orders for the new book Startup CEO: A Field Guide to Scaling Up Your Business by Matt Blumberg, CEO of Return Path, are available now on Amazon. Matt, who writes the awesome blog Only Once (which stands for “you can only be a first time CEO once”) has put a herculean effort into writing an amazing book while running a very large company.

This is the latest book in the Startup Revolution series of books that include Startup Communities: Building an Entrepreneurial Ecosystem in Your CityStartup Life: Surviving and Thriving in a Relationship with an Entrepreneur, and Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist.

I’ve worked with Matt since 2001 when I joined Fred Wilson and Greg Sands on the board of Return Path. At the time I was an investor in a company called Veripost that was a direct competitor with Return Path. Fred was an investor in Return Path. Each company was about 20 people. The founders knew each other well and were in a brutal competition in a market that didn’t yet exist. They decided they wanted to join forces, Fred and I cut a deal over the phone in 5 minutes, and Greg Sands (at Sutter Hill at the time) led a financing round that set a price for the combined company.

Twelve years later Matt is still Return Path’s CEO. George Bilbrey, one of the Veripost founders, is the President. They are incredible partners and Matt is still a first time CEO, but now running a 400 person company that dominates its market.

The book is broken up into five parts:

  • Part I: Storytelling
  • Part II: Building the Company’s Human Capital
  • Part III: Execution
  • Part IV: Building and Leading a Board of Directors
  • Part V: Managing Yourself So You Can Manage Others

Matt  has the entire outline of Startup CEO up on his blog. As with all books in the Startup Revolution series, it combines practical experience with advice with stories with commentary from other experts.

I think Startup CEO is going to be a must read for any CEO. Do Matt a solid and go pre-order it today.


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.

Minda Zetlin 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.