(This is the third in a series of three posts on this topic.)

In previous posts (here, here) , I talked about the difference between Mentors and Coaches and also how to select the right ones for you. Once you’ve selected a Mentor or Coach, here are some tips to get the most out of your engagement.

Starting to work with a CEO Mentor is fairly easy. Give them some materials to help understand your business, and then come prepared to every session with a list of 1-2 topics that are keeping you up at night where you want to benefit from the person’s experience.

Kicking off a CEO Coach engagement is more in-depth. I always recommend starting to work with a CEO Coach by doing a DEEP 360.  Not one that’s a bland anonymous survey instrument, but one that involves the Coach doing 15-20 in-depth interviews with a wide range of people from team to Board to others in the organization to people you’ve worked with outside the organization, including some non-professional contacts.  Let the Coach really learn about you from others.  The reason for this is that, although you may have an area of development that you want to focus on (like I did when I met Marc), you may actually need help in other areas a lot more acutely.

In general,  I’d say these are a few good rules of thumb for getting the most out of your Coach or Mentor relationship and sessions of work together:

• Do your homework.  If you have an assignment to read an article, take a survey, or just write something up, either do it or cancel the next meeting or it will be a waste of everyone’s time
• Be present.  Step away from your desk. Turn off email.  Silence your phone.  These are some of the most valuable times for your own personal development and growth, and they are few and far between when you get to be a CEO.  Treasure them
• Bring your whole self.  Even if your coach is a full 5 on the Shrink-to-Management Consultant scale I mentioned above, people are people, and you’re no exception.  You have a bad day at home — it will show through at work and it will impact your Coach conversations (maybe less so your Mentor ones).  Don’t ignore it.  Mention it up front
• Don’t bullshit.  You know when you’re wrong about something or have made a mistake.  You may or may not be great about admitting it publicly, or even admitting it to yourself.  ADMIT IT TO YOUR COACH.  Otherwise, why bother having one?
• Encourage primary data collection.  The biggest place I’ve seen coaching relationships fail is when the Coach or Mentor only has access to a single point of information about what’s happening in the organization — you.  Even if you’re not in full-on 360 mode, encourage your Coach or Mentor to spend time with others in the organization or on your board here and there and have a direct line of communication with them.  If they don’t and all they’re working off is your perspective on situations, their output will be severely limited or subject to their own conjecture.  Especially if you can’t get the prior bullet point right (garbage in, garbage out!)
• Make it your agenda even if it means changing on the fly.  You may be working on an analysis of your team’s Myers-Briggs profile with your Coach – and that’s the topic of your next meeting – but right before the meeting, you learn that one of your CXOs is resigning.  Change the agenda.  It’s ok.  It’s your time, make it work for you
• Learn to fish.  At the end of the day, a good CEO Coach should offer you ways of thinking about things, ways of being, ways of learning in your organization, processes to give you the ability to do some elements of this by yourself – not just answering questions for you.  Sports trainers are useful for an athlete’s entire career to push them harder in workouts, but they also teach athletes how to work out on their own
• Reality check the advice.  Make sure to test the strategies that Coaches or Mentors are giving you against your organization.  All strategies won’t work in all organizations.  These conversations should offer a variety of strategies – you can pick one or pick none and do something totally different.  The value isn’t in being told what to do, it is in going through the process of deciding what to do for YOUR organization with some expert inputs and reflections on other experiences
• Close the loop.  I’ve written before about how to solicit feedback as a CEO.  To make sure your coaching work is effective, be sure to include feedback loops with your key stakeholders (team and board) on the things you’re working on with your CEO Coach

It’s worth the money.  CEO Coaches can be really expensive.  Like really, really expensive.  $500-1,500/hour expensive.  CEO Mentors can be free and informal, but sometimes they charge as well or ask for advisor equity grants.  Even if you have a thin balance sheet, don’t be shy about adding the expense, and you shouldn’t pay for this personally.  Adding 10-20% to the cost of your compensation will potentially make you twice as effective a CEO.  If your board doesn’t support the expense…well, then you may have a different problem.

There’s a lot written publicly about this topic.  Jason Lemkin at SaaStr has a particularly good post that really puts a fine point on it.  And the coaching team at Beyond CEO Coaching a new boutique coaching firm specializing in coaching black CEOs, writes in “Who are you not to be great?”, “You can play it safe and reduce your risks and likely the rewards, or you can go big.  We at Beyond CEO Coaching want to help you to go big.”

By the way, this entire framework applies to non-CEOs as well.  Every professional would benefit from having a Coach and a Mentor in their life, even if those aren’t paid consultants but more senior colleagues or members of the company’s People Team.  Sometimes a Mentor and a Coach are one and the same…sometimes they are not.

Thanks to a large number of Bolster members I know personally who are CEO Coaches and Mentors for reviewing these posts — Chad Dickerson, Bob Cramer, Tim Porthouse, Marc Maltz, Lynne Waldera, Dave Karnstedt, and Mariquita Blumberg.

As I finished up my work on the Second Edition of Startup CEO:  A Field Guide to Scaling Up Your Business and started working on a new startup, my colleagues and I started envisioning a new book as a sequel or companion to Startup CEO that is going to be published on June 9 with our same publisher, Wiley & Sons.  The book is called Startup CXO:  A Field Guide to Scaling Up Your Company’s Critical Functions and Teams.

Simply put, the first book left me with the nagging feeling that it wasn’t enough to only help CEOs excel, because starting and scaling a business is a collective effort. What about the other critical leadership functions that are needed to grow a company?  If you’re leading HR, or Finance, or Marketing, or any key function inside a startup, what resources are available to you? What should you be thinking about?  What does ‘great’ look like?  What challenges lurk around the corner as you scale your function that you might not be focused on today?  If you’re a CEO who has never managed all these functions before, what should you be looking for when you hire and manage all these people?  If you’re an aspiring executive, from entry-level to manager to director, what do you need to think about as you grow your career and develop your skills?

Startup CXO is a “book of books,” with one section for each major function inside a company.  Each section is be composed of 15-20 discrete short chapters outlining the key “playbooks” for each functional role in the company – Chief People Officer, Chief Financial Officer, Chief Marketing Officer, Chief Revenue Officer, etc., hence the title Startup CXO – which is a generally accepted label in the startup ecosystem for “Chief ____ Officer.”

Here are the front and back covers of the book, with some great endorsements we’re so proud of on the back.

This is an important topic to write about at this particular time because America’s “startup revolution” continues to gather steam.  There are only increasing numbers of venture capital investors, seed funds, and accelerators supporting increasing numbers of entrepreneurial ventures.  While there are a number of books in the marketplace about CEOs and leadership, and some about individual functional disciplines (lots of books about the topic of Sales, the topic of Product Development), there are very few books that are practical how-to guides for any individual function, and NONE that wrap all these functions into a compendium that can be used by a whole startup executive team.  Very simply, each section of this book serves as a how-to guide for a given executive, and taken together, the book will be a good how-to guide for startup executive teams in general.

Startup CXO has my name on it as principal author, and I’m writing parts of it, but I can’t even pretend to write it on my own, so the book has a large number of contributors who have the experience, credibility, and expertise to share something of value with others in their specific functional disciplines — most of my Bolster co-founders are writing sections, and the others are being written by former Return Path executive colleagues — Jack Sinclair, Cathy Hawley, Ken Takahashi, Anita Absey, George Bilbrey, Dennis Dayman, Nick Badgett, Shawn Nussbaum, and Holly Enneking.

Startup CXO is also pretty closely related to Bolster’s business, since we are in the business of helping assess and place on-demand CXO talent, and as such, the final section of the book has a series of chapters written by Bolster members who are career Fractional Executives about their experience as a Fractional CXO.

The book is available for pre-order now at Amazon and Barnes & Noble.

Oh, and stay tuned for a third book in the series (kind of) due out late this year. More on that over the summer as the project takes shape!

As I mentioned the other day, the second edition of Startup CEO is out.  This post is a teaser for the content in one of the new chapters in this edition on Authentic Leadership.

As I mentioned last week, the book went to press early in the COVID-19 pandemic and prior to all the protests around racial injustice surrounding the George Floyd killing, so nothing in it specifically addresses any of those issues.  In some ways, though, that may be better at the moment since the book is more about frameworks and principles than about specific responses to current events. Two of those principles, which are timeless and transcend turmoil, uncertainty, time and place, are creating space to think and reflect and being intentional in your actions. In a world in which CEOs are increasingly called upon to deal with more than traditional business (pricing, strategy, go-to market approaches, team building, etc.) it’s imperative to approach and solve challenging situations from a foundation that doesn’t waver. 

At Return Path our values were the foundation that provided a lens through which we made every decision. Well, not every decision, only the good ones. When we strayed from our core values, that got us into trouble. The other principle, outlined in Chapter 1 of the Second Edition, is leading an organization authentically.

Let me provide a couple concrete examples of what I mean by “Authentic Leadership” since the term can be interpreted many ways.

One example is to avoid what I call the “Say-Do” gap.  This is obviously a very different thread than talking about how the company relates to the outside world and current events.  But in some ways, it’s even more important.  A leader can’t truly be trusted and followed by their team without being very cognizant of, and hopefully avoiding close to 100%, any gap between the things they say or policies they create, and the things they do.  There is no faster way to generate muscle-pulling eyerolls on your team than to create a policy or a value and promptly not follow it. 

I’ll give you an example that just drove me nuts early in my career here, though there are others in the book.  I worked for a company that had an expense policy – one of those old school policies that included things like “you can spend up to $10 on a taxi home if you work past 8 pm unless it’s summer when it’s still light out at 8 pm” (or something like that).  Anyway, the policy stipulated a max an employee could spend on a hotel for a business trip, but the CEO  (who was an employee) didn’t follow that policy 100% of the time.  When called out on it, did the CEO apologize and say they would follow the policy just like everyone else? No, the CEO changed the policy in the employee handbook so that it read “blah blah blah, other than the CEO, President, or CFO, who may spend a higher dollar amount at his discretion.”

What does that say about the CEO? How engaged are employees likely to be, how much effort are they willing to devote to the company if there are special rules for the executives? You can make any rule you want — as you probably know if you have read a bunch of my posts or my book over the years, I’m a proponent of rule-light environments — but you can’t make rules for everyone else that you aren’t willing to follow yourself unless you own the whole company and don’t care what anyone thinks about you or says about you behind your back.

Beyond avoiding the Say-Do Gap, this new chapter of the book on Authentic Leadership also talks about how CEOs respond to current events in today’s increasingly politicized and polarized world.  This has always felt to me like a losing proposition for most CEOs, which I talk about quite a bit in the book.  When the world is polarized, whatever you do as CEO, whatever position you take on things, is bound to upset, alienate, or infuriate some nontrivial percentage of your workforce.  I even give some examples in the book of how I focused on using the company’s best interests and the company’s values as guideposts for reacting (or not reacting) to politically divisive or charged issues like guns or “religious liberty” laws.  I say this noting that there are some people who *believe* that their side of an issue like this is right, and the other side is wrong, but the issues have some element of nuance to them.

Today’s world feels a bit different, and I’m not sure what I would be doing if I was leading a known, scaled enterprise at this stage in the game.  The largely peaceful protests around all aspects of racial injustice in America in the wake of the murder of George Floyd — and the brutality and senselessness of that murder itself — have caused a tidal wave of dialog reaching all corners of the country and the world.  The root of this issue doesn’t feel to me like one that has a lot of nuance or a second side to the argument.  After all, what reasonable person is out there arguing that George Floyd’s death was called for, or even that black Americans don’t have a deep-seeded and widespread reasonable claim to inequality…even if their view of what to do about it differs?

I *think* what I would be doing in a broader leadership role today is figuring out what my organization could be doing to help reduce or eliminate structural racial inequality where we could based on our business, as opposed to driving my organization to take a specific political stand. I know for sure that I wouldn’t solicit feedback from a select group of people only, but I would create a space where voices from across the organization (and stakeholders outside of it as well) could be heard. That’s not a solution, but a start, and in challenging times making a little bit of headway can lead to a cascading effect. It can, if you keep the momentum.

And, in line with “authentic leadership,” it’s okay to admit that you don’t have the answers, that you might not even know the questions to ask. But doing nothing, or operating in a “business as usual” way won’t make your company stronger, won’t open up new opportunities, won’t generate new ideas, and won’t sit well with your employees, who are very much thinking about these issues. 

So, in today’s challenging times I would follow my own advice, be thoughtful and reflective, and intentional in searching for common solutions.  I’d try to avoid “mob mentality” pressure — but I would also be listening carefully to my stakeholders and to my own conscience.

In the coming weeks, I’ll write posts that get into some of the other topics I cover in the book, but none of them will be as good as reading the full thing!

Must-Read New Blog

I’ve talked about Why I Love My Board a few times in the past.  I was reminded at my quarterly Board meeting and dinner this week that it’s a great and unusually strong group, and we’re lucky to have them.  Fred and Brad have both been prolific bloggers for years,and I know many of you follow their blogs closely.  Think of that as getting a taste of the input and wisdom you’d get by having them on your Board.

In a very exciting development, one of my independent directors, Scott Weiss, has now started blogging on the Andreessen-Horowitz platform.  Scott is probably our most outspoken and colorful director (and that’s saying something).  Scott just joined Andreessen-Horowitz as a partner in their fund, so he now a VC, but his experience as an operator both at Hotmail in Internet 1.0 and then at Ironport have been incredibly valuable for me as an entrepreneur, and I expect most of his posts to focus on the entrepreneur’s perspective.

Two of Scott’s first three posts, Looking Bigger and Ridiculously Transparent, are perfect examples of the value I’ve gotten out of my six year relationship with Scott as a Board member.  If you want a taste of what it would be like to have him in your corner…subscribe to his blog!

More thoughts on some of Fred’s and Brad’s points about VC deal algebra, valuation, and liquidation preferences for venture-funded startups. My apologies if this gets a little too technical or too long!

On liquidation preference: Preferred stock makes sense, participating preferred makes less sense. Sure, a VC who puts capital at risk in a startup should be entitled to get his or her money out before management and common shareholders who are paid to run the business. But I’ve always had an issue (even when I was in the venture business, although admittedly not as a partner) with the participating preferred security which allows VCs to get their money out first, and then still receive their proportional share of the rest. Fred calls this “a loan with an option,” and that’s the best presentation I’ve ever heard of the security. But what’s always struck me as a bit over the top about this is that it gives VCs downside protection at the same time they’re negotiating even more upside in a deal.

One simple solution to this, if you can negotiate it, is a “kickout” provision which makes the participation feature on the security go away if the company becomes worth a multiple (usually 2x or 3x) of the post-money valuation of the financing. In other words, it gives the VC the downside protection they want but gives you and other shareholders more of the upside if things go really, really well.

On valuation and deal algebra: I completely agree that valuation is a derived number and that it’s completely misunderstood in early stage investing. However, I think that while there may be low correlation between valuation and what the business is worth today, there are a few things that have always bugged me about VC valuations:

While I understand that valuation is more a function of future potential than current value, it sometimes feels like companies get punished for having a track record. Let me clear about my point – it’s not that that I actually think VCs lower valuations unfairly when companies demonstrate poor results. It’s actually the opposite. VCs are quick to bid up the valuation on companies that don’t have revenue or even a lot of operations just because the idea is cool or because the theoretical market is large (Friendster, anyone?). I don’t think VCs as a group do a good enough job of risk-adjusting or future-competition-adjusting valuations for new companies, or they get caught up in what Fred once called Venture Fratricide and just pour money into new sectors en masse. This has the unintended side effect of making management teams of existing companies feel like their ideas aren’t interesting any more because they’re not new and shiny.

Second, it’s interesting to note that while VCs use valuation as a way of placing limits and getting protection on their bet about the future potential of the company and entrepreneur, entrepreneurs have no corresponding mechanism to place limits or receive protection against having a bad VC. (VCs actually have many tools at their disposal to reign in poorly performing management teams once the deal is signed – they can fire them, cram them down, force all their common stock to be on a vesting schedule or subject to clawback.) But make no mistake about it – a bad VC can almost kill a company, or certainly keep it from realizing its full potential, and once that deal is signed, the entrepreneur typically has little recourse. I’m not sure there’s an easy solution to this particular problem either, but it’s one that’s worth thinking through with a good lawyer the next time you negotiate a term sheet with a new venture investor (and certainly one that is easier to negotiate if you either have a good track record as an entrepreneur or multiple VCs interested in your company). I made one suggestion around participation in future financings in my earlier posting on term sheet negotiations — item #8.

The final thing that’s bugged me about valuations stems from what Fred calls the 1/3 rule (1/3 of a VC’s investments work out well, 1/3 go sideways, 1/3 go bad). As a result of the rule, valuations and deal structures can end up being about VCs getting as much upside as possible out of their winning deals to cover their losses from their zero-return deals. What bugs me about this is that entrepreneurs don’t have that same luxury of a diversified portfolio – they are 100% invested in terms of their human capital and often their investment capital in their company. I fully realize that this is the nature of the beast, but I’ve always felt as a result that entrepreneurs should negotiate – and VCs should be willing to give – proportionally much more upside to management in the event that the deal turns out to be a big winner. This point relates back to my first point about participating preferred securities.

Next up in this series…Reverse Engineering Venture Economics, and managing other kinds of investors (Angel and Strategic).

Beyond Policy

Policies are an important part of managing employees. Similarly, contracts are an important part of running the commercial side of the business.  But it’s impossible to legislate every potential down-the-road situation ahead of time. That’s why one of the 13 core values at Return Path is

We believe in doing the right thing

I’ll admit that more than most of our values, this one sounds like Motherhood and Apple pie. Who doesn’t want to do the right thing?  The reason this value is an important part of our culture is that when we are in a tough situation, we stop and ask ourselves the most basic, yet thought provoking question — what’s the right thing to do here?

• When you fire an employee immediately before a major block of stock options vest, what’s the right thing to do?  Vest the options
• When you have a client who for some reason can no longer use your product or service or legitimately can’t pay their bill, what’s the right thing to do?  Let them out of their agreement, or at least let them suspend their agreement, even if it’s a long term contract
• When you make a payroll mistake and the employee doesn’t notice it but you discover it after the fact, what’s the right thing to do?  Let the employee know…and make them whole (the reverse is true of course as well, in cases where employees are the beneficiaries of an unnoticed payroll error – the right thing is to let the company know and make the company whole)
• When you have a choice of a car service (price equal) that runs only hybrid cars or more luxurious gas guzzlers for your routine trips to the airport, what’s the right thing to do?  Go green, baby!
• When you make a mistake and a client is adversely impacted but doesn’t notice it, what’s the right thing to do?  Fess up, quickly and thoroughly

I’m sure we don’t always get the tough calls right. That’s part of being a community of humans with emotions and faults. But we know that our reputation as a business goes well beyond following our policies and contracts and try to do the right thing as circumstances dictate.

A Culture of Appreciation

As I mentioned in my last post in the Collaboration is Hard series, we’ve tried to create a culture of appreciation at Return Path that lowers barriers to collaboration and rewards mutual successes.  We developed a system that’s modeled somewhat after a couple of those short Ken Blanchard books, Whale Done and Gung Ho! It may seem a little hokey, and it doesn’t work 100% of the time, but in general, it’s a great way to make it easy for people to say a public “thanks” to a colleague for a job well done.

The idea is simple.  We have an “award request” form on our company Intranet that any employee can use to request one of five awards for one or more of their colleagues, and the list evolves over time.  The awards are:

ABCD – for going Above and Beyond the Call of Duty

Double E – for “everyday excellence”

Crowbar – for helping someone in sales “pry our way in” to a new customer

Damn, I Wish I’d Thought of That – for coming up with a great insight for the business (credit for the name of course goes to our former colleague Andy Sernovitz)

WOOT – for Working Out Of Title and helping a colleague

Our HR coordinator Lisa does a quick review of award submissions to make sure they are true to their definitions and make sure that people aren’t abusing the system, and the awards are announced and posted on the home page of the Intranet every week and via RSS feed in near-real time.

Each award carries a token monetary value of $25-$200 paid with American Express gift checks, which are basically like cash.  We send out the checks with mini-statements to employees every quarter.

It’s not a perfect system.  The biggest shortcoming is that it’s not used evenly by different people or different groups.  But it’s the best thing we’ve come up with so far to allow everyone in the company to give a colleague a virtual pat on the back, which encourages great teamwork!

Doing Well by Doing Good, Part IV

This series of posts has mostly been about things that people or companies do that help make the world a better place — sometimes when it’s their core mission, other times (here and here) when it becomes an important supporting role at the company.

Today’s post is different — it’s actually a Book Short as well of a new book that’s coming out later this fall called Green to Gold:  How Smart Companies Use Environmental Strategy to Innovate, Create Value, and Build Competitive Advantage, published by Yale Press and written by Daniel Esty (a Yale professor and consultant), and a good friend of mine, Andrew Winston, a corporate sustainability consultant.

Green to Gold is a must-read for anyone who (a) holds a leadership position in business or is a business influencer, and (b) cares about the environment we live in.  Its subtitle really best describes the book, which is probably the first (or if not, certainly the best) documentation of successful corporate environmentalstrategy on the market.

It’s a little reminiscent to me of Collins Built to Last and Good to Great in that it is meticulously researched with a mix of company interviews/cooperation and empirical and investigative work.  It doesn’t have Collins “pairing” framework, but it doesn’t need to in order to make its point.

If you liked Al Gore’s movie, An Inconvenient Truth, this book will satisfy your thirst for information about what the heck the corporate world is doing or more important, can do, to do its part in not destroying our ecosystem.  If you didn’t like Gore’s movie or didn’t see it because you don’t like Al Gore or don’t think that many elements of the environmental movement are worthwhile, this book is an even more important read, as it brings the theoretical and scientific to the practical and treats sustainability as the corporate world must treat it in order to adopt it as a mainstream practice — as a driver of capitalistic profit and competitive advantage.

This is a really important work in terms of advancing the cause of corporate social responsibility as it applies to the environment.  Most important, it proves the axiom here that you can, in fact, Do Well by Doing Good.  If you’re interested, you can pre-order the book here.  Also, the authors are writing a companion blog which you can get to here.

Email Marketing Good and Bad:  Case Study Snippets

I had a good meeting this morning with one of our long-time multi-channel retailer clients who is in town for Shop.org’s Annual Summit.  Over the course of our conversation, she relayed two things going on in her world of email marketing at the moment that bear repeating (with her permission, of course).

First, the good.  In a recent study, our retailer hero determined that customers who receive their email newsletters and offers (not even open/click, just receive) spend on average 3x as much on in-store purchases than their non-email counterparts in any given week or for any given campaign.  Talk about deriving non-email or non-click value from your email marketing efforts!

Second, the bad (ok, well, it’s the ugly as well).  Our retailer hero was just nailed by Spamhaus because someone out there complained about a transactional email he or she received from the retailer.  She estimates that the poor Spamhaus listing is costing her millions of dollars a year in lost sales from regular customers.  The email was literally about a refund that the retailer owed the customer (why there was a complaint — who knows?).  What did Spamhaus suggest the retailer do?  Repermission their list around transactional messages — “or else.”  Seems to me that that’s a pretty tough stance to take on rather shaky evidence and with no appropriate dispute resolution mechanism (e.g., one that’s not just tuned to mailers’ interests, but one that’s fair in the broadest sense of the word).  No wonder Spamhaus is being sued, and no wonder the vigilante blacklist providers of the world are losing traction with ISPs and corporate system administrators.  Authentication and real, professionally run reputation systems with ample amounts of representative data, feedback loops, and dispute resolution mechanisms will ultimately win the day over the vigilantes of the world.  Folks like Spamhaus can get things right lots of the time and in fact do provide a valuable cog in the global world of spam fighting, but they’re less great at making amends when they don’t.

So email continues to have its challenges around filtering and deliverability…but how cool is it that marketers are really sinking their teeth into metrics that prove how effective the email channel is for driving sales, both online and offline?

A Tale of Two Strategies

Two headlines right next to each other in today’s Wall Street Journal tell an interesting story.  First, they tell of Google’s strategy to allow advertisers to use Google’s web site to bid on and buy print advertising in over 50 leading newspapers. Then comes CBS’s strategy to bring in a new executive digital media M&A guru, Quincy Smith from Allen & Company, to “find the next YouTube.”

(These links should work for a week, but I think that’s all the Journal allows – sorry!).

So there you have it.  CBS’ grand interactive plans are about trying to do value-based Internet acquisitions.  Best of luck.  Les Moonves’ quote is somewhat sad — “This shows how serious we are about new media.”

All that against a backdrop of Google probably dropping three engineers and a case of Jolt Cola into a room for a week and coming up with an automated way of buying print ads in newspapers whose circulations are declining precipitously.  Eric Schmidt’s quote is equally interesting for its contrast to Moonves:  “Anything that we can do to improve the economic efficiency of the old model [of advertising] transfers money from the old model to the new model.”

Now to be fair, Google did say that eventually they would have 1,000 people working on offline media placements, 10% of its workforce, but they will probably grow their way there profitably, instead of turning into a private equity firm.

Why Do Companies Sell?

Fred has a good post today about Facebook and why they shouldn’t sell the company now, in which he makes the assertion that companies sell “because of fear, boredom, and personal financial issues.”  He might not have meant this in such a black and white way, and while those might all be valid reasons why companies decide to sell, let me add a few others:

• Market timing:  As they say, buy low – sell high.  Sometimes, it’s just the right time to sell a business from the market’s perspective.  Valuations have peaks and troughs, and sometimes the troughs can last for years.  Whether you do an NPV/DCF model that says it’s the right time to sell, or you just rely on gut (“we aren’t going to see this price again for a long time…”), market timing is a critical factor
• Dilution:  Sometimes, market conditions dictate that it isn’t the best time to sell, BUT company conditions dictate that continuing to be competitive, grow the top line, and generate long-term profits requires a significant amount of incremental capital or dilution that materially changes the expected value of the ultimate exit for existing shareholders (both investors and management)
• Fund life:  Fortunately, we haven’t been up against this at Return Path, but sometimes the clock runs out on venture investors’ funds, and they are forced into a position of either needing to get liquidity for their LPs or distribute their portfolio company holdings.  While neither is great for the portfolio, a sale may be preferable to a messy distribution

Fred’s reasons are all very founder-driven.  And sometimes founders get to make the call on an exit.  But factoring in a 360 view of the company’s stakeholders and external environments can often produce a different result in the conversation around when to exit.