Tag: ceo

Jul 11 2018

CEO Problems

Recently, I was talking to a CEO of a company I’m on the board of. We were discussing a problem in the category of something new Is fucked up in my world every day

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.

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Jul 13 2017

The Loneliness of an Entrepreneur

This showed up in my inbox the other day from a friend of 20 years. He’s been involved in a number of companies that we’ve invested in over the years in different senior and/or co-founder roles, including CEO. It was short and sweet but captured the essence of something I often talk about with founders.

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

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Feb 28 2017

Don’t Play Hurt

I heard a great line from a CEO recently: “I don’t want to play hurt.”

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.

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Jan 13 2017

The Three Machines

Lately, I’ve been stewing over increased complexity being generated by companies around their organization approaches. While this activity varies by stage, in many cases the leadership team expands to a large (greater than six) number of people, there become two executive teams (the C-Team and the E-Team), the CEO gets sucked into endless distractions and working “in the company” rather than “on the company”, and I could go on with a 1,000 word rant on the challenges and complexity.

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.

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Dec 26 2016

CEOs Who Are Pleasers Should Spend More Time With Customers

I woke up this morning thinking about people who have a desire to please. This is not my personality type, but I encounter it regularly. Amy often describes herself as an “approval-seeking people pleaser” and I’ve learned a lot from my 30 years of interacting with her.

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.

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Jun 21 2016

Don’t Waste A Crisis

This cliche, which has uncertain attribution (Winston Churchill, Rahm Emmanuel, M. F. Weiner) is a priceless line that gets tossed out periodically, especially in the middle of a crisis.

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 TechnologiesI 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.

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May 5 2016

Your Wall Is Dingy

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.

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Mar 27 2016

Building Long Term Companies

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 CompaniesI 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 coachMany 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 itI’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 spiritWhile 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 DayI tell a short version of the Buddhist saint Milarepa’s story Eat Me If You WishComing 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 yourselfI 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.

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Jul 20 2015

Sometimes I Ask Myself If The Juice Is Really Worth The Squeeze

One of my all time favorite blog posts is Ben Horowitz’s The StruggleIf 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.

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Jun 1 2015

Hot Seat by Dan Shapiro: A Book Every Startup CEO Should Read

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.

  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 EntrepreneurIn 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.

First Email Between Shapiro and Feld

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 Capitalistwhich 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.

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