As I procrastinate from going for a run this morning, I started writing a post titled The Pro-Rata Gap Myth. After two paragraphs, I got tired of writing it and hit the “this is bullshit” wall – it’s too complicated to explain a myth that I’m not sure even matters.
So I deleted the post and decided to tell a story instead. This is a story I roll out occasionally with CEOs to help them explain how their words can easily be misinterpreted by their teams, especially as the teams get bigger. But it’s also a way that CEOs misinterpret what their investors or board members (or chairperson) is saying. And it creates endless organizational waste and misalignment when the CEO / investor / board member / leader isn’t clear about what she is saying and who her audience is.
Between 1996 and 2002 I was co-chairman of Interliant, a company I co-founded with three other people. Interliant bought about 25 companies during its relatively short life, helped create the ASP business (the pre-cursor to the SaaS world we know and love today), went public, and then blew up post-Internet bubble and ultimately went bankrupt before being acquired, partly because we created a capital structure (through raising a bunch of debt) that was fatally flawed, ultimately wiping out all the equity value.
While I learned a ton of finance lessons from the experience, I also learned a lot a leadership lessons. Your wall is dingy is one of them.
We had just acquired a company (I don’t remember which one or in which city) sometime in 2000. I was visiting the company post acquisition and wandering down the main hallway with the founder of the company we had just acquired. We were having a causal conversation and I offhandedly said “wow – your wall is dingy.” We kept walking, I did a Q&A thing with the founder and the company, and then went out to a mellow company lunch celebration type thing.
I had other stuff to do in the city so I stayed overnight and came back in early to have some meetings at the company the next day. As I was wandering down the same hall, I saw that there was a crew already in the office painting the wall with a fresh coat of paint. I got my coffee, wandered over to the founder’s office (he was also already in early), and asked why there was someone in the office painting the wall?
Founder: “You told me the wall needed to be painted.”
Brad: “I did?”
Founder: “It was while we were walking down the hall. We were talking about the new car I was thinking about buying and you said that the wall was dingy.”
Brad: “Oh yeah – that was said out of admiration for how frugal you are. You were telling me how this is the first new car you will have, since all of your other cars have been used cars. I admire how thrifty and scrappy you’ve been and thought I was paying you a compliment.”
Founder: “Shit, I thought you were unhappy with how low rent our offices are and were commenting that we needed to make things a lot nicer.”
Brad: “Double shit. I was saying the opposite. Part of the reason you’ve been so profitable is that you don’t waste money on your offices. This is part of what we love about your company. And it’s part of why we were willing to stretch in the deal – we knew you know how to make money and that you value every dollar.”
We eventually both started laughing. It was a good bonding moment. Fortunately, it was just paint and didn’t cost that much, although it was one of 27,393 incremental expenses that helped sink Interliant, especially in a time when rent was skyrocketing and everyone needed fancier and fancier offices because, well, because everyone else had fancier offices.
Ever since that moment I’ve been a lot more tuned into what I say. I still talk the way I did then – plainly and with whatever is on my mind – but I try to add the reason so that I’m not misinterpreted. If I could teleport myself back to that hallway in 2000, I’d say “Wow – your wall is dingy, and I love it, because it reminds me how frugal you are.”
As a leader your words matter. It’s not that you have to necessarily choose them carefully, but make sure you explain them and try to confirm that they are understood.
I was catching up on a bunch of reading on the web from last week and came across a post by Lars Dalgaard titled Thoughts on Building Weatherproof Companies. I don’t know Lars, but know of him as the founder/CEO of SuccessFactors and now a partner at A16Z, and was curious after recently reading a Forbes article about Zenefits a few weeks ago titled ‘A Lot Of Things Went Wrong’: Lars Dalgaard On Zenefits Scandal.
Any CEO I’ve ever worked with has heard me say “build the company and make decisions as though you’ll be running it forever” many times. While forever is a very long time and so far the idea of running a company forever hasn’t happened, it’s a great frame of reference for a CEO to operate from. So, I found myself nodding at a bunch of things Lars wrote in his post and I encourage you to read it.
Following are a few of the headlines of the points that resonated with me along with my quick thoughts.
Successful companies are bought, not sold: This cliche is said 100x per day by VCs. And it happens to be true. Build something great and important and opportunities to be bought, whether you want to pursue them or not, will come to you.
Develop a perpetual, aggressively help-seeking mindset: A simpler way to say this is “learn quickly, do it continuously, and surround yourself with people you can learn from.” There’s a subtext about sublimating your ego and fears, which appears in several other parts of the post and is a characteristic of everyone I know who is a learning machine.
Invest in a coach: Many of the CEOs (and founders, and execs) we work with have coaches. We strongly recommend them. My partners and I have used Nancy Raulston since we started Foundry Group and my extremely close friend Jerry Colonna is someone I describe as “the best startup CEO coach on the planet.” I have a running coach, even though all I do is run marathons, and not competitively. I’ve never understood why people who are trying to be excellent at something don’t recognize the value of a coach.
Build a real board of directors … and use it: I’ve long been an advocate of building a real board early in the life of your company. Lars talks about adding non-VC directors early and I strongly agree. I’ve seen too many boards that are just gradual expansions of the number of VCs around the board table with each successive round of financing. While the CEO works for the board, a great board effectively works for the CEO also, doing whatever it can (as individuals and collectively) to help the CEO be successful with one fundamental governance role – that of insuring that if the CEO is not being effective, the board can take action to change this, which often, but not always, means replacing the CEO. If you want to go deeper on this, I’ve written a book on it called Startup Boards: Getting the Most Out of Your Board of Directors.
Kill the monsters of the mind, while preserving your spirit: While a provocative title, I’m not sure your goal should be to kill the monsters of the mind. In my post titled Something New Is Fucked Up In My World Every Day, I tell a short version of the Buddhist saint Milarepa’s story Eat Me If You Wish. Coming to terms with the monsters (or demons) is much more powerful (and efficient) than killing them, since it often makes them simply disappear.
Don’t lie to yourself: I remind you of the great John Galt quote “Nobody stays here by faking reality in any manner whatever.” If you ever stay in my guest condo in Boulder, you’ll see a painting by my mother with this quote incorporated into it hanging on the wall.
It’s Sunday – if you are reading this, take some time to read Thoughts on Building Weatherproof Companies and ponder it in the background, instead of burning brain cells on whatever political crap is discussed on the internets today. Lars, thanks for taking the time to write it.
One of my all time favorite blog posts is Ben Horowitz’s The Struggle. If you are a founder and you haven’t read it, open it up in another tab for after your finish this post.
On Friday, a CEO I know sent me the following message.
“Brad – I crafted the entry pasted below this morning for my eyes only (and for my own therapeutic purposes), but in thinking about it today, I realized that you’re probably one of the only people I know who might be able to relate or who has interacted with others with similar sentiments. I’m in a good place mentally and it simply feels good to share this with someone else.”
I read it and immediately asked if I could post it anonymously. It’s in the same category for me as The Struggle, but with a different tone. Fortunately, the CEO said yes so I can share it with you. It follows.
Sometimes I wake up and look in the mirror and don’t recognize myself.
Sometimes I haven’t slept properly in days or weeks and I look in the mirror and most certainly don’t recognize myself.
Sometimes I get frustrated that going to bed is like suiting up for battle. I know that many sleepless and restless hours lay ahead before it’s okay to go back to work.
Sometimes I see how physically drained and weak I’ve become. Long gone are the days of being a muscular collegiate baseball player with MLB scouts at my heels or a lean and mean Ironman triathlete and marathon runner. My mental desire to achieve athletic greatness is at an all-time high, but my physical prowess leaves a lot to be desired.
Sometimes I wonder about underlying health issues that aren’t noticeable in the mirror and might not rear their ugly head until years into the future.
And sometimes, I see the disappointing medical test results and wonder if I’m on a path towards failure. Sometimes I don’t even know where to get started to get back on track.
Sometimes I look around and realize that many childhood friends have steady corporate jobs, children and other pursuits. They work to live rather than live to work and they are able to parse work stresses from the rest of their lives.
Sometimes I’m jealous, but mostly I’m lonely and longing for friendship with those who understand how emotionally and physically draining running a business can be. Can’t someone else understand why I can’t commit to an 8pm dinner on a Tuesday night when I’m absolutely drained?
Sometimes I ask myself if the juice is really worth the squeeze.
And sometimes, I admonish myself for such thoughts. My life is not that hard relative to those who have more physically demanding jobs.
Most of the time, however, I love my life and my job has been a source of great energy and inspiration. I know we’re onto something big and the journey has allowed me to surround myself with amazing colleagues and supporters. I only wish that I could find the perfect harmony between health, happiness and my career.
On Saturday, I polished off Hot Seat: The Startup CEO Guidebook. I started it last weekend at the tail end of my Weekend Reading on Startup Communities but four books weren’t in me so I didn’t finish it.
It was excellent and is now on my “all startup CEOs must read” list. My recommended book list for startup CEOs is very long, but there are only three books on the must read list.
- Startup CEO: A Field Guide to Scaling Up Your Business by Matt Blumberg
- The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz
and now #3: Hot Seat: The Startup CEO Guidebook by Dan Shapiro.
All three are from experienced CEOs. Each is a delightful mix of stories, advice, and experiences. They are all contemporary, highly relevant, and fun to read. Regardless of the number of times you’ve been a startup CEO, from having started ten companies to being an aspiring CEO/founder, you will learn a lot from each of them.
I don’t think I’ve ever physically been in the same place as Ben, but we’ve exchanged emails in the past and he was willing to allow me to republish his classic essay The Struggle in the book I wrote with my wife Amy – Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur. In contrast, I’ve known and worked with Matt since 2001 when I first invested in his company Return Path (well – it’s a little more complicated than just an investment – see my post Return Path Launches Email Intelligence from 2012 where I recounted some of the story.)
Return Path is an extraordinary company that I’m proud to have been involved with for the past 12 years. At our board meeting last week, Matt gave me and Fred Wilson our 12 year anniversary gift – a pair of red Return Path-branded Adidas sneakers. I still vividly remember the phone call Fred and I had where we cut a deal to merge two nascent companies – Veripost and Return Path – in what became Return Path. We cut a deal in 10 minutes – I offered up a 50/50 merger and Fred suggested he wanted a little more since Return Path had raised 3x the money Veripost had. I responded with “how about 55/45″ and Fred said “it’s a deal.”
Matt has become one of my best friends and I treasure every minute I get to spend with him.
Dan is a new friend. The first email I remember getting from him was from 9/3/13, titled My new project: Robot Turtles, and he acknowledges in Hot Seat that it’s the one time he spammed everyone in his address book. I don’t know why I was in his address book, so I asked Dan, and he dug up his very first email to me, which happened to be about the term sheet series that my partner Jason Mendelson and I wrote that lead to our book Venture Deals.
The first substantive email exchange we had was on 3/18/15, as a result of an intro from Ben Huh, the CEO of Cheezburger and another long time friend. We went back and forth on a rapid fire thread about Dan’s newest company Glowforge and the round he was starting to raise. We agreed to terms on a financing on 4/20/15 and closed a $9m financing with True Ventures on 5/8/15, at which point Amy and I went to Paris to celebrate (actually, we just went on vacation for one of our quarterly off the grid vacations.) There were a number of articles around the financing, but the best – and most thorough explanation of the company – was in Natasha Lomas‘s Techcrunch article Seattle’s Glowforge Is Building A Maker Machine To Challenge Amazon Prime.
Suffice it to say that in 75 days, I’ve gotten a good dose of Dan and am having an absolute blast working with him. He’s definitely got a healthy dose of evil genius combined with deep wisdom from being around the startup block a number of times. He’s tireless, intense, but delightfully funny and witty. He’s got extremely broad range as a CEO and entrepreneur, which comes through in his daily activities as well as his writing.
Which brings me back to Hot Seat. Like Matt and Ben’s books, it’s very fast paced. The chapters are short, written in first person, and easy to read. He’s not shy about calling things out clearly, including his own crazy experiences, especially the things he totally fucked up or had no idea about when he first encountered them. His examples are great, including some from mutual friends including Rand Fishkin and Ben Huh. The book is well organized and easy to dip in and out of. He flogs Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist, which I put in the flattering special bonus category. And – he’s got great footnotes in each chapter which give you a special dose of his sense of humor.
I hope to get to work with Dan for a long time on Glowforge. But, regardless, I know I’ll be regularly recommending Hot Seat: The Startup CEO Guidebook to every CEO I know.
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 (email@example.com).
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.