Matt Blumberg has a new book out titled Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams. It’s a follow-up to his previous book, Startup CEO: A Field Guide to Scaling Up Your Business.
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.
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)
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!
I used to love the Matrix’s Red Pill / Blue Pill metaphor and still use it occasionally to try to make a point around dealing with reality in an entrepreneurial context. Several years ago, I became deeply bummed out about how this metaphor was being used in politics and gender equity situations. It’s gotten worse since then, and I find many of the cases it is used in and the people who use it reprehensible, so I don’t use it much anymore.
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?
Seven years ago this week, I posted about a new book in our Startup Revolution series called Startup CEO: A Field Guide to Scaling Up Your Business, by my friend Matt Blumberg, then CEO of email marketing company Return Path in the Foundry portfolio. Today, with more around 40,000 copies sold all over the world and in multiple languages and formats, Matt and our publisher Wiley & Sons in partnership with Techstars have published a Second Edition of Startup CEO, which you can pre-order here.
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.
I read Ben Horowitz’s The Hard Thing About Hard Things last weekend. This is the third time I’ve read it. It gets better each time. If you are a CEO and you haven’t read it, buy it right now and read it next weekend.
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.
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.
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.
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
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.
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.
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.