Tag: ceo

Jan 7 2014

Falling Out Of Love With Being CEO

I was a CEO once. In my first real company, Feld Technologies, there were two founders – me and Dave Jilk. I was President (we didn’t use the CEO title then, but as the President, I was the “chief executive officer”) and Dave was Vice President. As we grew, other people had different titles, but the two of us ran the business.

I’ve been told that I was a good CEO, but after about ten people I didn’t like the role of CEO. But we stayed after it and built a successful company that was consistently profitable and acquired by a public company in 1993 for a few million dollars.

At the time it was acquired, we had 20 people. For the next nine months, I ran the consulting group of this public company. I reported to the two co-chairman and we quickly scaled up to 50 people in two offices. By the time we got to 50 people, I hated being the CEO of consulting group (I have no recollection what my title was, but again my role was the CEO role of this group.)

The parent company acquired a much larger consulting company – about 200 people – and I quickly handed the keys over to the new CEO (well, President) allowing Feld Technologies to become two of the branch offices of what ended up being AmeriData Consulting.

I have never wanted to be a CEO since. It’s a really hard job. Some people love it. Some people are outstanding at it. Everyone I’ve ever worked with in the role has struggled immensely at different points in time.

And some people grow to hate the role.

Recently, Rand Fishkin, the CEO of Moz, took an incredibly brave step. In his post Swapping Drivers on this Long Road Trip Together, he handed the CEO role over to his long time business partner Sarah Bird. As of January 15th, Sarah will formally become CEO and Rand will become an individual contributor on the executive team, reporting to Sarah.

We invested in Moz in April 2012. Rand wrote an epic blog on the financing titled Moz’s $18 Million Venture Financing: Our Story, Metrics and Future. It was so epic that the mainstream tech press didn’t really want to report on the financing since there was no new information they could discover, since Rand blogged every last detail.

Since that date, I’ve developed a professional love affair with Rand and Sarah. As an investor, I have no hesitancy to become close friends with the entrepreneurs we invest in. Rand and his wife Geraldine have become extremely good friends, and I have deep respect and affection for Sarah.

In the middle of 2013, Rand called me up and said “What do you think of the idea of me handing over the CEO reins to Sarah?” I reacted immediately with “That would be awesome.” There was silence – I don’t think Rand expected that reaction.

I knew Rand was unhappy as CEO. He was exhausted in his role. He had a strong senior team but carried around every ounce of stress and responsibility for all aspects of the business. He traveled constantly evangelizing Moz, SEO, and marketing. He loved certain aspects of what he was doing, but hated others. And many of the ones he hated were the ones that a CEO of a scaling business is responsible for.

I recognized this. It’s the same stuff I would hate if I ran a company the size and stage of Moz. It’s the stuff I hated when I was co-chairman of a 1,000 person public company and effectively acting CEO since the CEO we had recruited bailed after accepting the job, leaving us with a four month scramble to find a new CEO. It’s the stuff I remember hating leading a company of 50 people.

Now, Rand and I are different people. But he’s special. And magical. And amazing. And his special, magic, amazingness was being squandered as CEO, especially when he sat next to Sarah, who will be an awesome CEO while allowing Rand to be special, magical, and amazing in the next chapter of Moz.

I’m so incredibly proud of Rand for how he’s approached this, talked openly about it, and dealt with his own emotions, insecurities, and fears around this decision. And I’m extremely excited about Sarah become CEO and unleashing her talents on the new wave of growth at Moz, while Rand spends his time being true to what he loves in the context of Moz.

Building a company is hard. Being a CEO is hard. Working with people you trust, admire, and adore is a delight.

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Oct 16 2013

I’m A Talking Rubber Duck

Phin Barnes at First Round Capital just nails it today with his post To get the most out of your investors, turn them into rubber ducks

Go read it – I’ll wait and will be here when you get back.

I love Rubber Duck Debugging. I use this approach when writing, which I call “Writing with Yoda.” I have a little Yoda figurine staring at me at all times and when I stall out I just talk to him for a little while and then get started again. He always looks serene and wise and I almost always get going after talking to him for a little while.

Phin describes five steps to turn your investors into rubber ducks:

  • Frame the problem you are facing: describe the challenge in enough detail that I can understand it without being an expert (because I am probably not an expert)
  • Create context for an answer: Explain why this problem is a priority for you and the business and why you need to solve it now (because I am not involved in the day to day operation of your company)
  • Propose a few solutions: Describe a few paths you might take and talk through how you would choose between them (this helps me understand the outcome you want to achieve)
  • Be patient: Be open and engage deeply in the questions that I have and explain your answers with specific detail (even if it seems obvious)
  • Be active: The goal is to debug the system and the builder is most likely to find the bugs we seek (and to see others along the way)

These are similar to how to engage a great mentor, which we teach over and over again in Techstars – both to the entrepreneurs and the mentors. If you’ve ever done a Top of Mind Drill with me, you’ll recognize the Rubber Duck approach with one twist – storytelling.

I’m a storyteller. I learned this from my dad. It’s part of why I love to write – it’s a way for me to think out loud and figure stuff out while telling stories. So – my favorite Rubber Ducks are the ones who can also tell stories, at the right time.

The risk of a Rubber Duck only approach as a VC is that you become overly socratic. We all know the VC who just asks question after question after question. The questions are often good, and they drive you deeper into the problem, but at some point you need to take a break. You need a breath from answering more questions. You need an analogy to relate to.

This is when the Rubber Duck should tell a story.

At a board meeting recently, the CEO looked at me and said “just tell me the fucking answer.” So I did. And that works also. But not until the CEO wants that. Until then, be a Rubber Duck.

Remember – the CEO makes the decision, not the VC. Unless the CEO explicitly asks. And – if as a VC you don’t trust the CEO to make the decision, you have that discussion with the CEO right now. And if you are a CEO who’s VCs aren’t letting you make the decisions, buy them some Rubber Ducks.

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Sep 6 2013

Building A Business Operating System

Matt Blumberg‘s amazing new book Startup CEO: A Field Guide to Scaling Up Your Business is out and shipping. The early reviews are great, including this detailed one from Tech Cocktail.

Matt’s book is already having an impact in my world. At Cheezburger, we just added Scott Moore to the leadership team. Ben Huh, the founder/CEO who I adore and love working with, send out a powerful email about how he’s approaching Cheezburger’s next stage of growth, and how he’s thinking about building the business operating system. He builds off many of the concepts in Matt’s book and told me I was free to blog this for the world to see.

Following is Ben’s email.

——–

Hey Cheezburgers,

After recruiting our new COO & President Scoot Moore, I am shifting one of my major projects to on boarding Scott. I’m kicking off the process of building the business Operating System for Cheezburger. This is a super important item that I am thrilled to get started on.

It’s perfect timing for us. As COO & President, Scott has management responsibility for a huge area of Cheezburger. By building the metrics, communication rhythms, reports, etc. I can really help Scott get a feel for our business and where we stand as we plan for 2014. It’s one part communication, one part feedback process, and one part creating clarity.

A business Operating System is a simple idea:

  • Using the company’s values (of Truth, Excellence, and Happiness)…
  • create a set of consistent rhythm for communications, meetings, procedures and decision-making…
  • which helps align everyone’s goals with the ultimate objectives of the company.

Put in other words: A business OS is how we consistently and clearly communicate, hire, make decisions, etc. that help us do more faster.

In practice, this comes down to some answers to questions like this: (examples)

  • When do we plan for the next year? And who owns the process?
  • How do I measure my performance against my, or my team’s goals?
  • I need another person on my team to help better reach my team’s goals. How do I go about doing that?
  • I’d like to send out a company-wide update on something my team did. How do I do that?
  • How do I know what I am working on aligns with the company’s goals?
  • What metrics do we report company-wide? And why?
  • etc. etc. etc.

It’s an idea I first heard from another Foundry Group CEO, Matt Blumberg. In fact, he’s written a book based on those ideas.

One of the key improvements you should see as a result of this should be more consistency and clarity in communications and processes. This is one of the reasons why I push for a single IT system like Google Drive vs having two, and why I want you to post content for dissemination in our intranet. I hope that the OS will help you see the bigger picture. The opposite of having an effective business OS is a company that is confused due to lack of clarity and unable to move in the same direction together, therefore missing goals and opportunities.

There are 6 key areas that I want to structure the OS around (this will evolve as I work with Scott and the exec team):

  1. Company-wide communications and meetings
  2. Creating, aligning, and sharing goals
  3. Measuring performance against goals and metrics
  4. Establishing cadence, rhythm, and deadlines
  5. Clarity in decision-making process, transparency, and openness
  6. Well-functioning systems and operational processes

For you, the impact will be that I will be talking about almost everything in the context of our Culture/Values, Goals/KPIs/Metrics, and Systems/Processes.

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Aug 16 2013

Being A Great 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.

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Jul 11 2013

Don’t Let Fear Dominate Your Thinking

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.

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Jul 9 2013

Pre-Order Startup CEO, The Newest Startup Revolution Book

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.

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Jun 12 2013

Zen and the Art of Entrepreneurship

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!

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Mar 28 2013

The Power of A Great CEO Coach

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.

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Aug 6 2012

The Power Of Honesty In An Entrepreneur – VC Relationship

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.

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Aug 4 2012

All CEOs Should Be An Outside Director For One Company

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.

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