I’ve been working with Matt since 2000. That year, we merged two companies: Return Path and Veripost. Matt was the co-founder/CEO of Return Path. Fred Wilson was his lead investor. I was the lead investor for Veripost. The two companies did the same thing and were the only two competitors in a nascent category called “email change of address” (Veripost’s original name was IECOA which stood for “Internet Email Change of Address”). They were bashing each other over the head in a non-existent market as the Internet bubble began collapsing.

The founders of each company talked and, in between efforts to decimate the other, agreed it might be worth merging to survive. This guy named Greg Sands at a firm called Sutter Hill had met with both and was interested in the category and encouraged them to merge, at which point he’d fund the combined company. Fred called me and said, “Let’s figure out a deal.” I said, “They are both worthless right now – how about 50/50?” Fred responded with, “I have more money invested in Return Path than you do in Veripost – how about 55/45.” I answered, “Deal.” So for the deal, investors on both sides converted to common, we split the combined company 55/45, Matt became CEO, and Greg led a new Series A financing into the combined company. Twenty years later, we sold the business, a $100 million, profitable company, to Validity. Matt was still CEO. Fred, Greg, and I were still on the board.

Last year, Matt started a new company called Bolster. He co-founded it in partnership with High Alpha (we are LPs) and SVB. Soon thereafter, USV (Fred’s firm – we are LPs) and Costanoa (Greg’s firm – we are LPs) invested. It’s off to a great start. If you are looking to expand your leadership team or board, are looking for a part-time executive role or board role, or are an investor looking for fractional executives to join your portfolio companies, you should become part of the Bolster network right now.

I’ve worked with Matt for over 20 years and have experienced many ups and downs. His hard-won lessons from Return Path show up in Startup CEO: A Field Guide to Scaling Up Your Business.

For lessons from Matt and his Return Path management team, many of who are now execs at Bolster, you want to read Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams. When I saw the outline for Startup CXO, I grinned a wry smile. The book is 132 chapters broken into 11 sections. After the intro, the following sections are written by each exec.

• Finance – Chief Financial Officer – Jack Sinclair
• People – Chief People Officer – Cathy Hawley
• Marketing – Chief Marketing Officer – Nick Badgett and Holly Ennerking
• Sales – Chief Revenue Officer – Anita Absey
• Business Development – Chief Business Development Officer – Ken Takahashi
• Customers – Chief Customer Officer – George Bilbrey
• Product – Chief Technology Officer and Chief Product Officer – Shawn Nussbaum
• Privacy – Chief Privacy Officer – Dennis Dayman
• Operations – Chief Operating Officer – Jack Sinclair

There’s a final part on The Future of Fractional Executive Work with a chapter by a different leader for each area above. Matt’s writing shows up regularly throughout, including an ending chapter for each section titled CEO-to-CEO Advice.

Each chapter is two to five pages long. It’s tons of information, organized well, in tight, bite-sized chunks. For example, here are the chapters in Part Five: Sales by Anita Absey (p. 247-302)

• Ch 54: In the Beginning: From Prospect to Customer
• Ch 55: Hiring the Right People
• Ch 56: Profile of Successful Salespeople
• Ch 57: Some Myth Busting
• Ch 58: Compensating Sales Team Members
• Ch 59: Pipeline
• Ch 60: Scaling the Sales Organization
• Ch 61: Scaling Your Team Through Culture
• Ch 62: Scaling Sales Process and Methodologies
• Ch 63: Scaling the Operating System
• Ch 64: Marketing Alignment
• Ch 65: Market Assessment and Alignment
• Ch 66: Expanding Distribution Channels
• Ch 67: Geographic Expansion
• Ch 68: Pricing and Packaging
• Ch 69: CEO-to-CEO Advice

The brilliance of this book is that everyone on your leadership team, including the CEO, should read it and then discuss it. Pick one section each week. At the end of a quarter, the entire team will have discussed all the functional roles, have a deeper understanding of expectations and responsibilities, use a common language for talking about what people are doing, and be able to adapt things to your own company. Also, if you aspire to be a CXO – you can figure out your career path by understanding the whole functioning of the relevant and adjacent departments.

I’m going to encourage every leadership team I work with to take this approach with Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams.

Matt and team, thanks for writing this!

However, I used it today for a company that is doing well and has exceptional strengths and some fundamental weaknesses.

This is true of every company that is doing well.

But it’s hard to deal with reality all the time. When things are going well, leaders (and boards) often avoid dealing with weaknesses. Some board members and investors are great at motivating a CEO to level things up. Others aren’t. Some CEOs want to embrace the challenge of leveling up in areas where they, and the business, are fundamentally weak, even if it’s emotionally and functionally challenging. Others don’t, or their own behavior and wiring get in their way.

There are many points in a company’s life where the CEO and the board can either deal with or deny reality. When dealing with reality, a key factor is embracing the business, team, and individual’s weaknesses and then deciding how to address them. Collectively. With empathy and emotional support for each other.

This isn’t easy. Over the past 30 years, I’ve been in this position many times, often multiple times as a board member in a particular company. These are different than crisis moments, where everything is on the line. It’s often when many things are going well, but there are prominent areas of the business that aren’t keeping up with what’s working.

I’ve never figured out magic words to say as a board member in these moments. Instead, I say what is on my mind, take responsibility for my participation in any weaknesses, dysfunction, or challenges, and focus on where I think we need to put additional energy in improving the business.

This is often an acknowledgment that we need to add a few experienced people to the leadership team. The CEO has to drive this. When the right people are added, notable positive shifts in the weaknesses can happen extremely quickly. But, in the absence of them, the talk generally continues, without action. Reality is not dealt with – just poked around the edges.

One of an effective board’s roles is to speak clearly about the weaknesses and hold the CEO accountable for addressing them. When I am effective as a board member, I do this well. When I’m not, I don’t. I’ve got plenty of cases of both in the last 30 years.

My mantra as a board member is:

“As long as I support the CEO I work for her. If I don’t support her, my job is to do something about that, which is not to replace her, but to try to get back to the place where I support her.”

Ultimately, as a board member and major investor, I can participate in replacing the CEO. While I’d prefer not to do that, I’m not afraid of doing it. But dealing with reality with the existing CEO is much more enjoyable and has generally been a more successful path for me.

All of this is extremely challenging, as it has to do with personal growth in the context of business growth. It’s easier to have entrenched thinking, play out the exact historical patterns that worked or be resistant to addressing whatever the current reality is. It’s compounded by the fact that exogenous factors are constantly changing and often change extremely fast.

The probability of long term success increases with a CEO, a board, and a leadership team is tuned into whatever the current reality is, their strengths and weaknesses, and focus on continually leveling up the weaknesses while continuing to play to their strengths.

If you are a CEO, spend a few minutes today contemplating whether your board is highly effective at helping you grow, scale, and evolve the business. Are you systematically and continuously addressing your weaknesses as an individual, leadership team, and company?

Are you dealing with reality?

Matt and I originally conceived of Startup CEO when I was writing Venture Deals where Matt organically ended up writing a sidebar for many of the chapters which we called “The Entrepreneur’s Perspective.”  At the time, we talked about him writing a full “instructional manual” for first-time CEOs, and that’s what Startup CEO became, with over 50 short chapters with practical “how to” advice on everything from Fundraising, to People issues, to Board management, to Self-Management. 

In the Second Edition, Matt, who led the sale of Return Path last year, added six new chapters on Selling Your Company, which really rounded out the book.

I have given or recommended Startup CEO to hundreds of CEOs over the years. Matt has been very generous with his time in mentoring other entrepreneurs or bringing his book to life in online education and webinars.  Today, he posted one of the new chapters from the Second Edition of Startup CEO on Techstars’ blog, TheLine, on Preparing Yourself for An Exit:  How Do You Know It’s Time to Sell? which is a great example of the new material in the book.

Matt and others are working on a companion/sequel to Startup CEO which will come out in late 2020/early 2021. So, get Startup CEO now so you’ll be ready for that one when it comes out.

There are endless gems in the book, many of them from Ben’s own experience. My favorite of all time, that stays with me through all the work I do, is his distinction between “peace time” and “war time.”

I think the first time he wrote about this was in his post in 2011 titled Peacetime CEO/Wartime CEO. There has been plenty of commentary on the web about it (see The Myth of the Wartime and Peacetime CEO, which really only says a CEO has to be effective in both wartime and peacetime to be successful.)

Ben has an incredible rant in the post that starts off with:

Peacetime CEO knows that proper protocol leads to winning. Wartime CEO violates protocol in order to win.

The rant is worth reading every single word, but I want to highlight and comment on a few of my favorites.

The first one is:

Peacetime CEO always has a contingency plan. Wartime CEO knows that sometimes you gotta roll a hard six.

BSG fans know about rolling a hard six even though the definition is contested by pilots who think non-pilots confuse planes with dice. In wartime, the odds are often very against you. Sometimes you just have to get lucky.

Another one that I love is:

Peacetime CEO strives for broad based buy in. Wartime CEO neither indulges consensus-building nor tolerates disagreements.

Things during wartime are intense. Decisions have to be made quickly. Many will be wrong, need to be overturned, and new decisions have to be made. Sitting around arguing about what to do simply doesn’t work. Get all the ideas out on the table, but then choose. And then execute like crazy.

Finally:

Peacetime CEO sets big, hairy audacious goals. Wartime CEO is too busy fighting the enemy to read management books written by consultants who have never managed a fruit stand.

Your big hairy audacious goal in wartime is not to die.

As an investor, I’m involved in some companies operating in peacetime and others in wartime. There’s a lot of emotional dissonance during the day as I go back and forth between them. I’ve learned how to be calm in both modes and deal with my emotions outside the context of interacting with CEOs, founders, and leaders. But, Ben’s metaphor of peacetime vs. wartime has been so incredibly helpful to me as an investor in identifying what mode I’m in that I should probably get him some sort of a gift as a thank you.

He gave me a great idea. He apparently plays a game with his young (I think around 10 years old) daughter. When they are sitting around in the evening, she occasionally says “Daddy, give me a CEO problem.” He does, she thinks about it a little, and then gives him a solution. He suggested to me that this often helps break him out of whatever thought rut he is in given how wacky and creative the answers typically are.

Unfortunately, I don’t have a daughter (or a son). While I have two golden retrievers and I’m a practitioner of rubber duck debugging, I don’t think this works as well as what my friend is doing. Oh – and I’m not a CEO, although the list of CEO problems that I’m exposed to is pretty long.

The next time you have a CEO problem (which will likely be in the next seven minutes if you are a CEO and awake), try to think about it through the lens of a 10-year-old and see if that gives you any new ideas.

Heard you and Jerry on CPR this morning, nice job!

What struck me was your point about the gap between expectations in the role of CEO or startup founder, or investor – and the reality of depressive events/emotions that are often present – but no one gets to expose or relinquish.

I felt this first hand in my experience, both as co-founder and later as CEO. I used to *hate* seeing people around town or whatever because they’d ask “how’s the startup going?” and usually extra commentary like “oh startup rockstar, and you must be killing it, etc…” and my answer was always “no, it’s fucking unbelievable hard, and anxious, and trying, and most of the time shit is more fucked up than you could ever imagine”. You live with that veil and it always made it worse when people wanted to interact with you but position it as only successful sounding answers would work.

I learned to approach others the way I wanted to be approached:

1. I recognize everyone has a “bag of despair” they carry – you can’t see it, and anything can be in there, work, home, friends, family – serious shit is wrong somewhere for everyone at most points in time. So know it’s there, don’t assume and ask questions from ridiculously positive framing, but rather in a way that lets folks share honestly and is then actually helpful dialog to them (if they do want to take the opportunity to disclose challenges and discuss)

2. when someone asks “how’s it going” be honest – share the good and the bad, but don’t feel like you have to fulfill the stereotype and give them the sugar coated answer

I loved that line.

In my world, some companies beat their Q416 numbers. Others made their Q416 numbers. Some missed their Q416 numbers. That’s life. Any VC who says otherwise (e.g. “All my companies are killing it”) is either full of shit or doesn’t have very many investments. It’s especially true by Q4 when a budget was finalized in Q1 since Q4 is by far the hardest quarter to forecast / predict.

We are now 67% of the way through Q117.  Plans for 2017 are either locked or getting finalized. These plans get reset based on the 2016 data, especially trends and progress (or lack thereof) from the second half of 2016. A year ago seems a very, very long time ago.

Let’s assume you missed Q416. I don’t care what the reason was for the miss. Your entire team is bringing that thinking into the budget process. “We need more resources to grow faster.” Or “There’s no way we can grow that fast.” Or “We made some expectations about what was going to have in Q4 around Christmas that didn’t come true.”

At a high level, these are rational reactions. But they don’t really help in thinking about 2017 or the budget process because they don’t get to the root cause. Using the Five Whys or some other process is key. Figure out what happened as your starting point. If you’ve already built and approved your plan without doing this, go ahead and stress test your plan by doing this now. Use the root cause analysis to lower your costs and increase your revenue so that you beat your plan. Ask yourself why what happened, happened. Keep asking why to the answers until you feel like you’ve gotten to the root cause.

Let’s assume 2016 resulted in some layoffs in the second half of the year. You were on a growth trajectory that wasn’t working, or you had invested in some products you decided to shut down. Or in 2015 you had raised a bunch of money, hired a lot of people, and assumed it was all going to just work out according to the spreadsheet model you used to build headcount and revenue expectations based on the headcount. And then it didn’t.

It’s now 2017. You’ve made real cuts and now have a core team that is sized correctly for your current business. The process sucked, but it’s more than a quarter behind you. The dust has settled and people are heads down working. You had a more sanguine budget process this year, with solid revenue growth but much lower head count growth.

Don’t play hurt. Get back on the metaphorical field. As CEO, put the Q4 miss or the Q3 layoffs behind you. Pick your head up and realize that you have a real business, but you hit a giant air pocket last year. That is normal – it happens all the time on the way to building a great business. Any CEO who denies that (as in “Yup – everything was awesome all the time – there were never any issues in our success”) as as full of shit as the VC who says something like “Every one of my companies is doing great.”

I encourage those VCs (and entrepreneurs) to read my post Something New Is Fucked Up In My World Every Day and reflect on their actual reality.

The struggle can be extremely painful, especially in the moment. But, if you are a great CEO (or manager), keep focusing on what you need to do to fix the immediate problem while continuing to play your long term game. And, most importantly, don’t deny reality in any way whatsoever.

And … Don’t play hurt.

Recently, I saw a structure rolled out by a CEO at a company I’m an investor in that made me pause because of its simplicity and brilliance. I didn’t like the labels the CEO used, but I loved the intellectual approach.

It coincidentally had three categories. Three is my favorite number and has been since I was three years old. While I can carry more than three things around in my head at a time, when there are only three attached to a specific thing I find that it’s second (third?) nature to me and requires no additional processing power to remember and organize my thoughts around three things.

If you recall my post on Three Magic Numbers, this will immediately make sense to you. Or if you’ve ever heard my story about struggling with clinical OCD in my 20s where the number three was one of my key anchor points, you’ll have empathy for my relationship with the number three.

I abstracted the structure I saw from the CEO recently into what I’m currently calling “The Three Machines.” While this can apply to any size company, it’s particularly relevant to a company that is in the market with its first product, or a company that is now scaling rapidly with a set of products.

The three machines are: (1) the Product machine, (2) the Customer machine, and (3) the Company machine.

If you step back and think about all of the activities of a company in the phases I described above, they fit in one of these three machines. However, most leadership teams don’t mirror this. Instead, in a lot of cases, there is a traditional leadership team structure that has a CEO and a bunch of VPs (VP Engineering, VP Product, VP Finance, VP H&R, VP Sales, VP Marketing, VP Customer Care, VP Operations, …) which are often title inflated with CxO titles (CTO, CFO, Chief People Office, CMO, COO, CRO, …) or artificial demarcations between VPs and SVPs (and EVPs.)

Regardless of title structure, the CEO has a span of control that gets wider as the company scales, often with more people being added into the hierarchy at the VP or CxO level. As this continues, and CxOs are added, you end up with the C-team and the E-Team (which includes the non-CxOs). The focus of each person is on a specific functional area (finance, marketing, sales) and traditionally scoped.

In a few cases, big organizational experiments ensue, often after the organization dynamics hit a wall. Holacracy, which is still bouncing around, was a relatively recent trendy one. I disliked holacracy from the first time I heard about it and resisted even experimenting with is, preferring to watch what happened when others tried it. In 2013, Nick Wingfield wrote an often-citied article in the NY Times titled Microsoft Overhauls, the Apple Way that is liked to a now famous graphic of different org charts for Amazon, Google, Facebook, Microsoft, Oracle, and Apple.

I’ve wrestled with hundreds of conversations around this in the past few years. I never have felt satisfied, or even particularly comfortable, until I landed on the three machines recently.

My current hypothesis is that if you are a CEO, focus your organization on the three machines. Product, Customer, and Company. Then, have a direct report own one of them. If you have a sub-scale leadership team (e.g. you are three founders and four other employees), as CEO you can own one, but not more than one. As you get bigger (probably greater than 20 employees), hopefully how you have enough leadership to have one person own each, but recognize that if someone is being ineffective as a leader of one of the machines, you will have to replace them in that role (either by firing them or re-assigning them).

Let’s assume you have enough of a leadership team that you have a key leader who can own each one. Organize the company leadership around each machine. The titles don’t matter, but the hierarchy does. Naturally, you will have a product or engineering leader for Product, you will have a sales, marketing, or operations leader for Customer, and you will have a finance or admin leader for Company.

But, this does not mean that your VP Engineering is your VP Product and Engineering. That rarely works – you want to separate these two functions. But your VP Product, or your VP Engineering, or your CTO could be responsible for the Product machine, with the other VP functions reporting to her. You probably also don’t want to merge your VP Sales and VP Marketing and VP Customer Care function into a VP of Sales, Marketing, and Customer Care. But, if you have a Chief Revenue Officer, you may have done this. While that can work, recognize that it works if the CRO realizes he is in charge of the entire Customer machine.

I’m still in the first few weeks of really building a theory around this so there’s a lot of sloppy thinking on my part so far. For example, I don’t think this necessarily means that the CEO only has three direct reports. But it might. Or, in some cases, at certain scales it might. I haven’t focused on what it means in terms of the overall hierarchy. I haven’t really thought about how multiple different product lines come into play. I don’t know if there needs to be dramatic retitling at the top.

I do, however, have several companies that are very clearly focused on these three machines. Yet, they are at different scale points and have different formal hierarchies. Over the next few months, I’m going to use this lens across every company I’m an investor in as I poke and prod at how it might, can, and should work. And, determine if it’s a valid hypothesis.

Feedback of any type is welcome.

With CEOs I often notice the pleaser personality in the context of employees. The pleaser wants everyone around him to be happy. This creates a positive reinforcement dynamic for the CEO – if everyone is happy, things must be good. If employees aren’t happy for any reason, that becomes a priority for the CEO to solve.

This often happens independent of the situation. The CEO is not focused on the root cause of what is going on, but rather the specific activity that is causing an employee to be unhappy, especially in the context of the CEO or another employee. Often, the source of unhappiness, dissatisfaction, or frustration is exogenous to the CEO and the company.

As I was rolling this around in my early morning brain, the thought occurred to me that if you are a CEO and a people pleaser, you should spend more time with your customers.

It’s not that employees shouldn’t be happy. That’s a cultural norm that can be a great goal. But it should be an embedded cultural norm, not the sole responsibility of the CEO. So, the CEO who is a people pleaser runs the risk of misallocating her time to ensuring employee happiness.

There are a plenty of CEOs who spend a lot of time with customers, but I’ve never met a CEO who spent too much time with her customers. Early stage CEOs often do this effectively but as the company grows, the time spent with customers as a percentage of overall time goes down. There are plenty of rational reasons for this, but it ends up in the same place – the CEO steadily spends a lower percentage of time with customers.

If you are naturally a pleaser, spend more time with your customers in 2017. Re-energize yourself by getting in the feedback loop with the users of your product. While they’ll have plenty of negative and critical feedback, you can then filter what matters, solve for it, and stay in a feedback loop that generates positive feedback as you make your customers happier, solving for your pleaser needs.

If you think your customers are uniformly happy, you are deluding yourself. If your employees are happy but your customers are unhappy, you are screwed as a business. And, if you are a CEO who is naturally a people pleaser and you are in this situation (happy employees, unhappy customers) you are likely destroying your business.

You are not going to please all of your employees. That’s not your job as CEO.  Instead, channel your need to please to spending time with customers.

Over the years I’ve been involved in many business crises. I qualify this, since my crises have never involved life and death or the survival of the human race. But they are still crises. Some have lasted moments while others have lasted months, and I can think of one that went on for three years – or at least took three years to dig out of.

I’ve only occasionally been in the CEO (or equivalent) role during a crisis. Most of the time I’m a board member or investor. As a result, I’ve participated in dealing with the crisis, but I’ve also been able to observe the behavior of the leader during the crisis. While I’ve had to go throw up in the bathroom after a particularly distressing conference call more than once, I’ve been fortunate to be able to be one level removed from the essence of the crisis.

A typical leader has a natural tendency is to be defensive in the face of a crisis. The first reaction is to blame someone – or something – else. Often the blame is aimed at something abstract or non-controllable, which often has nothing to do with the crisis, but is adjacent to whatever is going on so it’s an easy target. As soon as the blame is out there, the attack begins, which often causes others to be defensive, generating a vicious cycle of anger, hostility, frustration, and obfuscation at the beginning of the crisis.

Over time, I’ve learned that the best leaders take a completely different approach. When the crisis erupts, rather than immediately go into action, she pauses and takes a deep breath. She starts collecting data about what is happening. In parallel, she communicates the crisis to the key people who need to be involved – the board, the leadership team, and anyone specifically engaged in the crisis.

If the crisis lasts moments, rapid action is critical. But if it’s simply the beginning of a broader issue, especially one where the root cause isn’t known yet, the worst thing a leader can do is act immediately. As a teenager, my dad taught me about the idea of unintended consequences and I’ve had the experience, and how to deal with it, pounded into my soul over the years.

If you want to understand this better, I encourage you to read Charles Perrow’s classic book from 1984 – Normal Accidents: Living with High Risk Technologies. I often forget to mention it when asked which books have influenced me the most – Normal Accidents is in the top 10.

So, you are now in the crisis. As CEO, you feel an immense need to address whatever is causing the crisis and resolve it. But that’s only half of it. If all you do is focus on solving the crisis, you are missing the big opportunity, which is to learn from it and integrate it into the fabric of your company. It’s not that you won’t ever have a crisis again – you most certainly will. But if you can change the way your company functions in the context of a crisis in a positive way, you can actually get some value out of the crisis.

Don’t forget to breathe.

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.

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.

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.

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.

1. Startup CEO: A Field Guide to Scaling Up Your Business by Matt Blumberg
2. 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.

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 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.

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 (brad@feld.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.

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.

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).

But many of the companies I’m involved in have duos that develop over time. Sarah and Rand (Moz). Bre and Jenny (MakerBot). Matt and George (Return Path). David and David (Techstars).

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.