Behind the stories of most first-time venture-backed CEOs building startups and attacking markets at breakneck speed, there is usually a tight network of mentors and peers showing them the ropes of company building. That’s certainly been my experience at Pantheon—we likely would not exist if not for the crucial help of James Lindenbaum, Adam Gross, Steve Anderson, Ryan McIntyre, Brad Feld, and all of the advisors who have assisted us on our journey.
However, I’ve found there is a hard limit to how much you can learn about building a company from speaking with advisors. Before deciding on how to go about building your company, it is critical to build an understanding of other companies’ paths to success and learning from their mistakes along the way. I’ve found to really do that, often times you need to be there—out of your own office and physically present in theirs—to see with your own eyes how a company actually works.
That is the goal of CEO shadowing: to put you in the shoes of another CEO, let you observe, ask questions, and form a rich and detailed mental model of how another company operates. I’ve done it twice so far, and both times have learned more in a day of shadowing than I do in months of working sessions with mentors and peers.
My first time CEO Shadowing: Jud at Gnip in 2012
The first CEO I shadowed was Jud, who then ran Gnip which has since been acquired by Twitter. Foundry Group is a mutual investor of ours, and Jud and I met at an event in Boulder that they organized for portfolio CEOs.
In Boulder I ran around asking a number of CEOs and Foundry Partners for company management advice—how to run one-on-ones, structure executive meetings, manage my board, etc. Three times in row an answer to my question was prefaced by:
“You should really ask Jud this question because they just did this at Gnip and did a fabulous job.”
We were a 20-person company at the time, and Gnip had hit its stride and was growing very quickly. They were 50, soon to be 100—about a year and a half ahead of us in terms of scale. Gnip was known for being a very well-run company.
I cornered Jud at the event and soaked up as much data from him as I could. Then I went home, and realized how much more I really needed to learn from him and Gnip. The only way I thought I could really get answers to my questions was to go to Gnip and observe how Jud and his team ran the company.
So I sent this email:
“Can I fly to Boulder and shadow you for a day, and be a fly on the wall in yours and your team’s meetings?”
This was his response a couple of hours later:
“Fun! You bet! Only question is timing. Thoughts?”
Jud invited me to attend his management meetings and let me interview anyone on his entire team at will. In one day on-site I was a part of his exec kick-off meeting, attended a company product strategy meeting, and interviewed two executives, two engineers, and individuals from their sales and marketing team. I took notes, asked questions, and tried to fit in. I approached it like a journalist whose goal it was to write a profile on how Gnip, the company, worked.
I found the Gnip team to be incredibly focused and busy—while still gracious, helpful, and happy to talk at the same time.
What I learned
At the time I shadowed Jud, Pantheon had a very early executive team and not much in terms of process or structure. We operated on tribal knowledge and had the benefit that everyone implicitly knew what the others were doing. We knew we needed to build our team and create more structure, but how were we going to do that without screwing up what was working so naturally?
What I learned at Gnip was:
1) It was absolutely possible to build a 100-person company that operated as efficiently, or even more efficiently, than our 20-person company.
2) Process and structure could be additive to company culture, because it forces you to get specific about implicit assumptions that are so important to a company’s future (values, strategy, management philosophy, etc.)
3) There is good management and bad management, and you need effective leadership and stiff penalties when you fail to lead. It was up to us to build the company right. Gnip was built right, and it worked.
On top of that, I learned many, many small tactical things—from how to structure the agenda of an executive meeting, to how to arrange teams and desks, to optimizing how the people worked together.
But the tactics were built on the big learnings, which were important for this reason: seeing how Gnip worked gave me confidence to trust my gut in building my company. To be clear, Pantheon is built very differently from Gnip. Many of the things that worked for them won’t work for us—we picked our own path. But there are so many internal obstacles to building structure in a startup as it undergoes massive change, and to know that it could work because I saw it work enabled to me to keep my head down and keep working towards my goal without getting blown off course.
Visiting Gnip in 2012 was like visiting the hopeful, successful, parallel future to Pantheon. It was like getting to travel to a foreign, and more advanced planet, and then getting to return and apply what I learned.
Want to do this? Here are my suggestions for how to get the most out of CEO shadowing:
- Find a CEO at a company that is approximately 1-2 years ahead of yours (if you are $1M ARR, then $5-10M; if you are $10M, then $30-$60M). Ideally this is a CEO you admire, and one you already have a relationship with.
- Confidentiality is incredibly important. You should probably sign an NDA.
- Book a full day in the office with the CEO. I highly recommend visiting the day the CEO does the most “management” in a workweek—when executive meetings, planning, strategy, etc are scheduled.
- Get yourself invited to everything. Everywhere the CEO goes, you go. This requires the CEO to warn their company ahead of time and get the OK of their execs and team members.
- Spend half of your time observing in meetings, and half in one-on-ones with their team.
- Meet one-on-one with execs, managers, and individual contributors, ideally from numerous different teams.
- Ahead of time, prepare a list of questions with the CEO that you can ask of their team members, or research topics you can report back on that CEO wants to know (while respecting anonymity). Example questions:
- “What do the values of this company?”
- “What are the company priorities? Your team’s priorities? Your priorities?”
- “What did this company get right that has enabled it to succeed?”
- Take copious notes during all meetings and interactions. Anonymize feedback and send a full report of what you learned back to the CEO (this can be partial repayment for letting you shadow them).
- Keep asking questions and observing until you feel like you could give a valuable five-minute presentation on “how the company works” to your team and the CEO you are shadowing.
Asking to shadow a CEO of a company is a big ask. It’s out of the norm, and it takes time from their team. You can repay some of that by offering to share useful observation or doing outside research as part of your time there, but at the end of the day this may be the ultimate “pay it forward” generous act the startup community is willing to take on for fellow CEOs.
Investors: I believe this could be one of the most valuable things you could help facilitate for your portfolio company CEOs. If anyone else has shadowed a CEO, I’d love to hear how you approached it and how well it worked for you.
I got to spend a lot of time with my close friend Rand Fishkin the past few days. The first was at Denver Startup Week, where we did a panel discussion with Ben Huh and Bart Lorang where we discussed the pact between CEO and Board, the pact between Founder and Investor, and how to be transparent and direct.
The next day, Rand led a full day offsite for a number of CEOs in our portfolio.
In between, he wrote an epic blog post titled A Long, Ugly Year of Depression That’s Finally Fading. Go read it now – I’ll wait.
I love Rand – not in that surface “I love you man” kind of way. Ever since I met him and his wife Geraldine, I’ve adored them as a couple and each as individuals. I often develop deep personal relationships with the people I work with which can be challenging when businesses struggle and difficult decisions have to be made. I’ve had a few friendships fail as a result of the pressure, stress, and intensity of working through certain situations, but far more have strengthened as a result. It’s a risk I decided to take a long time ago and I’ll continue to do it, even when I have to cope with my own anxiety, emotional struggles, and even depression, as a result.
We invested in Moz in April 2012. Rand wrote so extensively about it in his post Moz’s $18 Million Venture Financing: Our Story, Metrics and Future that almost all of the major tech blogs declined to write about it “because all the news was covered in the post.” Whatever.
The first nine months were great – the business grew as planned as I started to get to know everyone and how things worked at Moz. The company was working on a major rebrand (from SEOMoz to Moz) as well as a huge software expansion which was started before I invested. But by mid-year 2013 things were not going as planned. Rand has written extensively about it, but when he and Geraldine visited us in Boulder for a few days around that time both Amy and I thought Rand was depressed.
By the winter time, Rand had decided to hand the CEO roles to his longtime partner and COO Sarah Bird. Shortly after, he acknowledged his depression in his post at the end of 2013 when he wrote Can’t Sleep; Caught in The Loop. Regardless of his struggle, he continued to work incredibly hard, but we started having a different conversation, this time as friends rather than investor / board member and CEO / founder. I was more concerned about Rand’s mental health than his activity at Moz, and our conversations were generally around this. At the same time, Sarah grabbed the CEO reins firmly and has done an outstanding job, which I knew would ultimately be helpful to Rand.
Rand looked better in the past few days than I’ve felt he looked in several years. I was thrilled to see his post come out between our rambling Denver Startup Week discussion and the full day of the CEO offsite.
Most of all, I’m delighted that my friend Rand’s depression is finally starting to fade. Rand – you are amazing – and loved by me and many. Carry that with you all the time.
I had a fun email exchange with an investor I’ve worked with for almost 20 years in response to something a CEO send out from a board we are both on. I said “fucking awesome.” He said “that’s an understatement.” I said “CEO is such a delight.” He said “CEO is negative maintenance.”
I loved this. So I’m going to use this post to think through the idea out loud and I’d love your feedback since it’s still a messy / blurry concept in my mind.
My hypothesis is that the opposite of high maintenance is not zero maintenance but rather it’s negative maintenance.
There are days that I’m high maintenance. Everyone is. But if you subscribe to my “give before you get”, or #givefirst, philosophy, you are constantly contributing more than you are consuming. I’ve talked about this often in the context of Startup Communities, but I haven’t really had the right words for this in the context of leadership, management, and employees in a fast growing company.
Suddenly I do. When I think about my role as an investor and board member, I’m often tangled up in complicated situations. I’ve often said that every day something new in my world gets fucked up somewhere. This used to be distressing to me, but after 20 years of it, if I don’t know what the new fucked up thing is by 4pm, I start to get curious about what it’s going to be.
We all know that creating companies from nothing is extremely difficult. The problems that arise come from all angles. Some are exogenous and some are directly under your control. Some are random and some are obvious. Some are compounded by other problems and mistakes, resulting in what my father taught me at a young age was the worst kind of mistake – one that was a mistake compounded on a mistake compounded on a mistake – which he called “a complicated mistake.”
Personally, when I find myself in a complicated mistake, I stop. I step back and pause and reflect. And then I try to figure out how I can change the dynamic into something positive, not continuing to build on my complicated mistake, but instead getting clarity on what the right thing is to do to get out of the ditch.
Negative maintenance people do this. I’ve seen, been involved in, and made some epic mistakes. The CEO I’m referring to above has a great company, but has also experienced some epic mistakes. How he handles them, works through them with his team, and his board, is exemplary. There is work involved by me and the other board members, but it’s not inappropriately emotional. It’s not high maintenance. It’s just work. Decisions have to be made and executed. And there are impacts from these decisions, which lead to more decisions. Ultimately this CEO is putting energy into the system as we work through the issue, which is where the negative maintenance (as opposed to high maintenance) behavior pattern arises.
I like this idea of negative maintenance people. I’m obviously trying to think it through out loud with this post, so weigh in and help me understand it better.
A few years ago, David Cohen and I started a Colorado CEO Jobs list in response to the regular stream of inbound email we got from folks looking to move to Colorado and interested in tech-related jobs. We seeded this list with CEOs from companies Foundry Group and Techstars had invested in. As other CEOs requested access to the list, we added them.
The list was managed in Yahoo Groups and had about 100 CEOs on it. It was simple – emails from people looking for jobs came to me or David and we forwarded them to the list. The hit rate was very high – I regularly get feedback from people that they’ve ended up with multiple interviews and a job from the introduction.
Both David and I felt like the list was pretty tedious to manage in Yahoo Group so about three months ago we restarted it and made it a Google Private Community. We culled the list a little and re-invited everyone, ending up with 56 active CEOs. We’ve been using the Google Private Community for a while and are comfortable that it’s a significant improvement over the Yahoo Group.
We are still keeping it private for now but are looking for any CEOs of tech companies in Colorado who want to join the list as we expand it from Foundry / Techstars related companies. Our goal is to have a wide audience of CEOs for anyone coming to Colorado who is looking for a tech related job.
We are keeping the list ONLY to CEOs for now as we plan to expand some of the things we are doing with the list.
So, if you are a CEO of a tech company in Colorado and want to be on our Colorado CEO Jobs List, just email me (firstname.lastname@example.org).
And – if you are looking for a job in a Colorado tech company, email me also and I’ll forward your info to the list.
I spent the last few days at CEO Bootcamp – Leadership Reboot. It’s run by my close friend Jerry Colonna with an awesome team of four. The next one is going to be in Tuscany, Italy from 6/4/14 – 6/8/14 and I expect it will be amazing. I encourage you to explore it and apply – the deadline for applications is 4/20/14. I arrived at Devil’s Thumb Ranch on Wednesday afternoon.
The first evening was a wonderful dinner and introduction to each other (about 20 of us) along with an evening session with a taste of what was to come. I attended as a special guest (I’m the only non-CEO / entrepreneur here) but participated as a peer.
Thursday was extremely intense with the focus on what a CEO does and the five challenges of a CEO. Everyone opened up, the discussion was incredible, and emotions were high, and yes, there were tears, as one of Jerry’s superpower’s is getting the tears to flow.
If you need a taste of Jerry and haven’t seen him in action before, the following TWIST Interview on The 6 Biggest Mistakes Founders Make is dynamite. By Thursday evening, we were deep into it. Some people were tired (I ended up taking a nap for 90 minutes during the late afternoon break), others were confused, and some were inspired. A word that was repeated regularly was grateful. Grateful to be with peers. Grateful to realize one wasn’t alone. Grateful to be able to be human in the midst of a group of other entrepreneur/CEOs.
A magical thing happened after Thursday dinner. The gang from Playback Theatre West came and spent two hours with us. I’d experienced Playback Theatre West last year at Boulder Startup Week. I was one of the stories they performed – I shared my story of moving to Boulder with Amy and they re-enacted it – interpreting things in real time – magnificently. Since I knew what we were in for, I knew that once things started happening the collision of improv and entrepreneurship would be a wonderful capstone to the day.
After a warm up, Rebecca asked for volunteers. Sam, who had been with us all day (as he’s one of the CEO Bootcamp founders as well as a member of Playback Theatre West), was one of the actors.There was a lull – everyone was unsure what to do next. So I stood up and went first.
When I stood up, I had no idea what story I was going to tell, so there was some meta-improv going on. By the time I sat down next to Rebecca to start telling my story, I decided I’d tell the story of my 50 mile race. The emotional fallout from the race, which I only mildly understood two weeks after I finished it, has had a profound impact on how I’m currently living my life given the deep depression that set in for me about seven months after the race and then lasted six months.
I told the story of the race. Rebecca and the gang asked questions along the way, pulling out pieces of my motivation for the race, along with the implications of the race. Some of the questions were simple, like “Why”, but set me off on a tangent that had nothing to do with the race. Then I sat back and watched them perform for five minutes. I laughed. And then I laughed some more. And then I had tears in my eyes. And then a wave of emotion flowed over me as I made a connection to something I hadn’t realized before. And then I settled down and smiled as they tied together some threads around my own motivations that had eluded me.
They did several more performances for different CEOs in the room including one about a hiring story that was happening and was unresolved and one about starting a company. Each was a hilarious and absolutely beautiful interpretation of the story told. After a super heavy and intense day, it was a perfect way to wrap things up. To realize we are all humans, by acting out the reinterpretation of our human stories.
I’ve become a huge fan of Playback Theatre West. I hope to do a lot more with them in the future.
I’ve been thinking about the concept of “the duo” a lot recently.
Many of the companies I’m involved in have either two co-founders or two partners who partner up early in the life of the business. Examples of founding partners including Andrei and Peter (Kato.im), Keith and Jeff (BigDoor), James and Eric (Fitbit), and Matthew and Cashman (Yesware). Of course there are many other famous founding duos like Steve and Steve (Apple), Jerry and Dave (Yahoo!), Larry and Sergey (Google), and Bill and Paul (Microsoft). My first company (Feld Technologies) had a duo (me and Dave) and the company that bought Feld Technologies did also – Jerry and Len (AmeriData).
Now, these duos are not the leadership team. But there is a special magic relationship between the duo. I like to think about it like the final fight scene from Mr. and Mrs. Smith where Brad and Angelina are back to back, spinning around in circles, doing damage to the enemy.
This is not just “I’ve got your back, you’ve got my back.” It’s “we are in this together. All in. For keeps.”
It’s just like my relationship with Amy. We are both all in. It’s so powerful – in good times and in bad times.
I’m on the receiving end of phone calls and video conferences with CEOs all day long. And, at least once a day, I can feel the intense stress on the person I’m talking to oozing through the phone or the screen. The conversation is often calm and rational, but below the surface is a bubbling cauldron of pressure.
Welcome to life as a CEO of a fast growing startup. Every day something new and unexpected comes at you. Often multiple things. Some are awesome. Some are ok. Some are bad. And some are awful.
Ben Horowitz wrote what I think is the best post ever on this called The Struggle. After I read it, I asked him if I could include it in my book Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur. He graciously said yes, so I did.
I felt The Struggle regularly when I was running Feld Technologies in the 1980s. I put myself at a disadvantage – when something went wrong people often called for “Mr. Feld.” My partner Dave carried a lot of the burden as well so I wasn’t alone, but I was on the receiving end of a lot of unhappiness over the years.
While I got better at compartmentalizing it, I never mastered it. I still struggle with it today. I can absorb an enormous amount of stress from the CEOs I work with. But sometimes I get overloaded and end up far out on a deep tree limb trembling with anxiety. I like to refer to this as “inappropriate anxiety” because I know exactly what is at the root cause, but my obsessive mind has a difficult time letting it go.
So I do what I can. I talk to Amy. I walk Brooks the Wonder Dog. I take a bath. I try to sleep a little more. I run more. I let the obsessive thoughts roll around in my head, chasing each other like characters from SpongeBob SquarePants.
And sometimes I just go in a closet and scream for a little while. I let all the bad energy out. I put my all into it – expelling the stress. Trying to reset my mind. Knowing that the inappropriate anxiety will go away and I’ll feel ok again.
When I hear this in the voice of a CEO I’m working with, I offer up myself as a release valve. While I don’t invite it, I want them to know they can vent to me. That they can bare their soul safely to me. That I won’t judge them on the pressure they are under. That I won’t try to solve the problem for them.
But that I’ll be there.
And I let them scream if they want to.
On my run this morning, my mind drifted to a common characteristic of CEOs that I work with. It was prompted by me randomly thinking about two back to back meetings I had yesterday – the first with Eric Schweikardt (Modular Robotics CEO) and his VP Finance and then with John Underkoffler (Oblong CEO) and his leadership team.
I’m regularly blown away by these two guys ability to collect new information, process it, and learn from it. Any meeting with them is not an endless socratic session from me to them, but rather the other way around. They know what they are trying to figure out and use me, and my broad range of experience, data, and opinions, to solicit a bunch of data for themselves that they use as inputs into their learning machine. Sure – I ask plenty of questions, but they do also, and as we go deeper, the questions – and the things that come out – get richer.
So – as I turned around on my run and headed back home (today was an out and back run), I started thinking about other learning machines that I get to work with. The ultimate is David Cohen, the CEO of Techstars. The entire model of Techstars is build around the context of the entrepreneur as a learning – and teaching – machine, where learning and teaching (which we call “mentoring”) are the different sides of the same coin.
Bart Lorang (FullContact CEO) is an awesome learning machine. While Bart isn’t a first time CEO, his level – and intensity – of inquiry is stunning. It reminds me of a younger Matt Blumberg, who has taken the concept to an entirely new level in his book Startup CEO.
I could keep going – almost of the CEOs I work with are in this category of learning machine. As I rounded the last turn and headed for home, I realized the learning machine model is consistent with a deeply held value of mine – reading and writing. More about that in another post.
I just did a long 90 minute video interview stretch with Boulder Digital Arts that generated a number of specific videos on entrepreneurship. While they are selling them, a few are free. One of the free ones is on Founder’s Syndrome and Origin Stories. Given the last few posts I wrote on CEOs, and some upcoming ones, I thought you might be interested in this one.
If you liked that, take a look at some of the others. They include:
- What I Wish I Knew About Business 20 Years Ago
- The Impact of My Book Startup Communities
- Essential Advice When Raising Capital
While they are inexpensive, if you use the discount code “Feld2014” you can get an additional 15% off.
tl;dr – If you are a CEO and want to take an amazing online course about being a CEO by Return Path’s Matt Blumberg, sign up for Startup CEO from NovoEd now.
Yesterday, I wrote about Rand Fishkin of Moz falling out of love with the CEO role. Today I read Jason Goldberg of Fab’s great post on his struggles as CEO in 2013 and what he learned from it. This topic is front of mind for me as many of the companies I’m on the board of are growing extremely fast and the demands on the CEOs are significant.
It’s really hard to be a CEO. Becoming a great CEO takes a lot of time, work, focus, coaching, and introspection. I’ve had the privilege of working with some incredible entrepreneurs who, over many years and several companies, became remarkable CEOs. Dick Costolo (Twitter CEO) immediately comes to mind. While I didn’t work with him at Twitter, I was on the board of FeedBurner and worked with him and his three founders (Eric Lunt, Steve Olechowski, and Matt Shobe), who are all still close friends. I learned an amazing amount from each of them, but especially from my time with Dick.
Another great CEO I’ve had the honor to work with is Matt Blumberg who has led Return Path since founding the company in 1999. Matt is a first time CEO and has a fun blog titled Only Once which references the idea that you can only be a first time CEO one time. In a delicious twist, he’s now been a first time CEO for 14 years. While Return Path has had countless twists and turns along the way, Matt has been CEO from inception and presides over a large and significant company that continues to be a leader in a market it helped create.
Fred Wilson, who is on the board of Return Path with me and Matt (along with the FeedBurner board, and the Twitter board) had a frank and insightful post about turning your team three times through the life of the company to meet the different challenges that face a company from its journey from sweat driven startup to massive scale. Often this process of turning the team includes the CEO; other times it doesn’t. In Matt’s case, there have been plenty of team changes along the way, but Matt has demonstrated an impressive ability to scale and adapt himself in the evolving role of a CEO of a rapidly scaling company.
As a result, when Matt started talking to me about writing a book about the role of a Startup CEO, I was super excited. I encouraged and supported this, and it resulted in another book in the Startup Revolution series that I’ve done with Wiley. Matt’s book, Startup CEO: A Field Guide to Scaling Up Your Business, is a must read for any CEO.
Last summer, Matt began exploring doing an online course around the content in Startup CEO. He teamed up with the Kauffman Fellows Academy to put together a course titled Startup CEO, an online class that really drills into the important material of the book. It’s the real deal with hours of video, Q&A that Matt did in front of a live studio audience of NYC startup CEOs, as well as engagement with the teacher through the NovoEd platform.
I’m encouraging all the CEOs in Foundry Group’s portfolio to take the class, and I encourage you to take the class as well.
The class starts on January 20th on the NovoEd platform. You can learn more about it on Matt’s blog post about the Startup CEO course.