Startup CEO (OnlyOnce- the book!), Part IV – Book Launches Today!

My book is officially on sale on Amazon and iTunes today.  The full detailed outline is here if you’re interested, and the link to buy it is here.

This is very exciting.  I had been saying for a while that I had no idea whether 50 people would buy it or 5,000, but the publisher (Wiley) tells me we had over 2,000 pre-orders, so that’s a great start, at least.

So thanks to those 2,000 brave souls, and anyone else who buys it as well.  I hope you enjoy it and look forward to your feedback directly, via OnlyOnce, via the #StartupCEO hashtag, via a rating/review on Amazon, or via the Startup Revolution web site.

I hope to get back to more regular blogging soon.  As you hay have noted, I’ve been more quiet than usual the last six months while writing the book.  But I have lots of great posts stored up…

This was a catchy title I caught in our shared Kindle library at a moment when I wasn’t connected to wifi and had nothing to read. Thanks to Mariquita for buying it…it was a good read.

The book is funny, irreverent, and deep. It speaks a lot about pain and failure and how those can help create resilience. It is also chock full of great anecdotes including a particularly memorable one about Pete Best, the original drummer for the Beatles who got fired by the rest of the band on the eve of their becoming famous.

Here’s one particularly representative quote:

Pain is an inextricable thread in the fabric of life, and to tear it out is not only impossible, but destructive: attempting to tear it out unravels everything else with it. To try to avoid pain is to give too many fucks about pain. In contrast, if you’re able to not give a fuck about the pain, you become unstoppable.

Every founder would benefit from reading this book. It won’t stop you from giving a f*ck about everything (it can’t), but it might give you a couple tools for not giving a f*ck about some things, which would clear up some mental capacity for other more important things!

What Makes an Awesome Board Member

(This post was requested by my long-time Board member Brad Feld and is also running concurrently on his blog today)

I’ve written a bunch of posts over the years about how I manage my Board at Return Path.  And I think part of having awesome Board members is managing them well – giving transparent information, well organized, with enough lead time before a meeting; running great and engaging meetings; mixing social time with business time; and being a Board member yourself at some other organization so you see the other side of the equation.  All those topics are covered in more detail in the following posts:  Why I Love My Board, Part II, The Good, The Board, and The Ugly, and Powerpointless.

But by far the best way to make sure you have an awesome board is to start by having awesome Board members.  I’ve had about 15 Board members over the years, some far better than others.  Here are my top 5 things that make an awesome Board member, and my interview/vetting process for Board members.

Top 5 things that make an awesome Board member:

• They are prepared and keep commitments.  They show up to all meetings.  They show up on time and don’t leave early.  They do their homework.  The are fully present and don’t do email during meetings
• They speak their minds.  They have no fear of bringing up an uncomfortable topic during a meeting, even if it impacts someone in the room.  They do not come up to you after a meeting and tell you what they really think.  I had a Board member once tell my entire management team that he thought I needed to be better at firing executives more quickly!
• They build independent relationships.  They get to know each other and see each other outside of your meetings.  They get to know inviduals on your management team and talk to them on occasion as well.  None of this communication goes through you
• They are resource rich.  I’ve had some directors who are one-trick or two-trick ponies with their advice.  After their third or fourth meeting, they have nothing new to add.  Board members should be able to pull from years of experience and adapt that experience to your situations on a flexible and dynamic basis
• They are strategically engaged but operationally distant.   This may vary by stage of company and the needs of your own team, but I find that even Board members who are talented operators have a hard time parachuting into any given situation and being super useful.  Getting their operational help requires a lot of regular engagement on a specific issue or area.  But they must be strategically engaged and understand the fundamental dynamics and drivers of your business – economics, competition, ecosystem, and the like

My interview/vetting process for Board members:

• Take the process as seriously as you take building your executive team – both in terms of your time and in terms of how you think about the overall composition of the Board, not just a given Board member
• Source broadly, get a lot of referrals from disparate sources, reach high
• Interview many people, always face to face and usually multiple times for finalists.  Also for finalists, have a few other Board members conduct interviews as well
• Check references thoroughly and across a few different vectors
• Have a finalist or two attend a Board meeting so you and they can examine the fit firsthand.  Give the prospective Board member extra time to read materials and offer your time to answer questions before the meeting.  You’ll get a good first-hand sense of a lot of the above Top 5 items this way
• Have no fear of rejecting them.  Even if you like them.  Even if they are a stretch and someone you consider to be a business hero or mentor.  Even after you’ve already put them on the Board (and yes, even if they’re a VC).  This is your inner circle, and getting this group right is one of the most important things you can do for your company

I asked my exec team for their own take on what makes an awesome Board member.  Here are some quick snippets from them where they didn’t overlap with mine (with only two inside jokes that I couldn’t resist putting up for the Board):

• Ethical and high integrity in their own jobs and lives
• Comes with an opinion
• Thinking about what will happen next in the business and getting management to think ahead
• Call out your blind spots
• Remembering to thank you and calling out what’s right
• Role modeling for your expectations of your own management team – Do your prep, show up, be fully engaged, be brilliant/transparent/critical/constructive and creative.  Then get out of our way
• Offer tough love…Unfettered, constructive guidance – not just what we want to hear
• Pattern matching:  they have an ability to map a situation we have to a problem/solution at other companies that they’ve been involved in – we learn from their experience…but ability and willingness to do more than just pattern matching.  To really get into the essence of the issues and help give strategic guidance and suggestions
• Ability to down 2 Shake Shack milkshakes in one sitting
• Colorful and unique metaphors

Disclaimer – I run a private company.  While I’m sure a lot of these things are true for other types of organizations (public companies, non-profits, associations, etc.), the answers may vary.  And even within the realm of private companies, you need to have a Board that fits your style as a CEO and your company’s culture.  That said, the formula above has worked well for me, and if nothing else, is somewhat time tested at this point!

From Blog to Book – Beyond Bullets

Hats off to fellow blogger Cliff Atkinson, who has just published a book called Beyond Bullet Points.  Cliff and his company, Sociable Media, consult on PowerPoint and presentations and have a great theory about how to do great presentations.

They follow the “clear, simple, and please God not so boring” guidelines espoused by a number of us in the business world, including Brad and of course Seth.  (BTW, if you haven’t read Seth’s e-book/treatise on Really Bad PowerPoint, you should do that as well, although I can’t find a link to it at the moment.)

One of the coolest parts of the book is that it really started out as Cliff’s blog, Beyond Bullets, then got Microsoft’s attention, then became a book.  What a great demonstration of old and new media reinforcing each other!

Fred, Brad, and Jerry have done a bunch of postings recently, and threaten to do more, sharing the VC perspective on many aspects of startups and entrepreneurship. I thought it might be interesting to share the entrepreneur’s perspective on the same subjects. I’ll try to cross-post and keep pace, but I’m already a couple behind, and I can’t crank out postings as fast as these guys can! (For reference, Fred and Brad are on my board, and Jerry as Fred’s partner is an advisor to my company, Return Path.)

Topic 1: Boards of Directors. All three have many good points. Brad says that boards come in three flavors (working, reporting, and lame duck), and that small companies need working boards which include other entrepreneurs in the industry as well as management and investors. He also advises to take good care of directors and not let them get bored. Fred calls the good ones engaged boards (interactive, candid, engaged, passionate, and involved) and says that while you can have a good company without an engaged board and even with a bored bored on occasion, to have a great business you need an engaged board. Finally, Jerry says that you should pick your board carefully and build it with some diversity like you would a management team and to avoid people who will yes you.

I basically agree with all of these points, and would add the following four thoughts for entrepreneurs:

1. Building a board can be one of a CEO’s greatest trump cards. Without being even a little bit disingenuous, you can use the “I’m the CEO and would like to talk to you about a potential board seat with my company” as an entree to meet face to face with some of the most interesting, senior, brand-name people in your industry (turns out, flattery will occasionally get you somewhere). Use this card wisely and sparingly, and always be prepared to follow up on your meetings, but take full advantage of it as a way to network. You never know what opportunities you’ll uncover along the way.

2. Don’t think of managing your Board as a burden. Communicate early and often to your Board members and make sure all big conversations and debates are pre-wired in one-to-one conversations before Board meetings, and that debates are framed and researched properly in advance of meetings. Nail the basics (reporting, financial reviews, well-crafted and easy-to-read materials sent out several days before the meeting), so you can focus the valuable meeting time on strategy, not on the minutiae.

3. Figure out how to work differently with investor directors and outside directors. VCs who sit on your board have very different interests, time availability, and things to contribute than outside directors, especially non-retired industry executives. Not all directors are created equally, and you don’t have to behave as if they are.

4. Sit on a board yourself. There’s nothing like a real-live counterpoint to make you take a step back and think about how to build and run an effective board. Find something — another startup, a nonprofit, your high school or college alumni association — to join as a board member. Watch and learn.

All that said, the most important thing I’ve found in running a board is following Brad, Jerry, and Fred’s collective wisdom about fostering an engaged/working board. Definitely don’t let them get bored on you!

I was trading emails a few weeks ago Elliot Noss from Tucows about the current state of the economy after being on a panel together about it, and he wrote:

The market is fascinating right now. Heated competition AND layoffs and hiring freezes. It feel like an old European hotel where there are two faucets, one is too hot and the other too cold.

While a quick rant about European hotel bathrooms could be fun…we’ll just stick to the sink analogy. As anyone who has ever tried to use one of these sinks that Elliot describes knows, they’re hard to use and illogical. Sure, sometimes you want freezing water and sometimes you want scalding water (I guess), but often, you want something in between. And the only way to achieve that is to turn on both freezing and scalding at the same time? That’s weird.

Then I was on another email thread recently with a group of CEOs, when John Henry from Ride With Loop said this:

Whatever the climate, we all surely agree there is no bad time to build a good business.

How true that is!

But here’s the worrisome part. It’s impossible to predict what’s going to happen next. We are in uncharted territory here with a land war in Europe, a partial global oil embargo of a top tier oil producer, a pandemic, supply chain problems, etc. etc. There are days and circumstances where everything feels normal. Plenty of businesses, especially in the tech sector, are kicking ass. And yet there are days and circumstances that feel like 2001 or 2009. It’s tough to navigate as a startup CEO. Yes, it’s obvious you should try to have a couple years of cash on hand, and that you should be smart about investments and not get too far ahead of revenue if you’re in certain sectors (presumably if you’re in an R&D intensive field and weren’t planning to have revenue for years on end, life isn’t all that different?). But beyond that, there’s no clear playbook.

And that’s where the worrisome line comes in. I saw Larry Summers on Meet the Press last weekend, who predicted that

a recession would come in late 2023.

Wait, what? Aren’t things messed up now? Yes, inflation is high, the stock market is down, and interest rates are creeping up. But the economy is still GROWING. Unemployment is still LOW. Summers’ point is a reminder that contraction is likely, but it may still be a ways off, it depends how the Fed handles interest rate hikes (and about a zillion other things), and it’s impossible to predict. That was more worrisome to me. If we’re navigating choppy waters now, it may not just be for a couple of quarters. It may be that 4-6 quarters from now, we are in for 2-3 quarters of contraction. That is a more than most companies are able to plan for from a cash perspective.

Frothy macro environments lead to bad businesses getting created, too many lookalike businesses popping up, or weak teams getting funded. When the tide goes out, as they say, you can see who is swimming naked. But if you’re building a good business, one that has staying power and a clear value proposition, with real people or clients paying real money for a real product or service, and if you’re serious about building a good company, keep on keeping on. Be smart about key decisions, especially investment decisions, but don’t despair or give up.

We’ll all get through this.

Sometimes It’s Worth Travelling 5,000 Miles for a 5 Minute Meeting

I re-learned this lesson shortly before the holidays.  We’re negotiating a big deal with a company out on the west coast, and we were at a tense and critical spot in the negotiations.  I knew that the only way to move the deal forward to a handshake and a term sheet was to meet face to face with the decision makers on the other side of the table, in person. 

So I got on a plane.  It wasn’t my first choice of activities, and although I was able to work a couple of other meetings into the trip, the trip was a long way to go for a really short meeting.  But it was 100% worthwhile, with a very specific mission accomplished.

As I mentioned in one of my earliest posts, it’s important to be "Present AND Accounted For" in business settings, and with everyone’s busy schedules and increasingly frenzied and multi-tasking office environments, it’s harder than ever to really get someone’s attention.  There’s just no substitute for looking someone in the eye and doing a real handshake, not a virtual one.

Drawing the LineWe are having a bit of a debate at the moment internally around our Sender Score deliverability business about how to handle clients who are in businesses that are, shall we say, not exactly as pure as the driven snow.  As a company that provides software and services to businesses without a vertical focus, we are often approached by all sorts of companies wanting our services where we don’t love what they do.  Examples include:

Gambling
Tobacco
Neutriceuticals
Guns
Adult content or products

Our challenges are along three dimensions, each of which is a little different.  But common threads run through all three dimensions. 

Dimension 1:  Our deliverability technology platform.   Our basic technology is used by mailers of all shapes and sizes to preview their campaigns, monitor their deliverability, and analyze their reputation metrics.  It doesn’t deploy campaigns.  Do we care who the users are?

Dimension 2:  Our full service deliverability practice that comes with consulting and high-touch account management.  This service offering has an additional layer of complexity in that our employees work closely with accounts and their web sites.  We already allow employees to opt-out of accounts where they find the work objectionable.  But is that enough?

Dimension 3:  Our whitelist, Sender Score Certified. This one is even trickier.  On the one hand, our program has fairly clear, published standards.  We do a thorough qualitative check of the client’s web site and email program to make sure, among other things, that the program is opt-in.  We monitor the client’s quantitative reputation metrics in real-time to make sure its complaint rate is low, signifying that its customers like (or at least don’t mind) receiving its email.  On the other hand, this program is supposed to signify the best of the best for email marketing and newsletters, which is why it’s used by so many ISPs and filters as their standard for defining “good mail.”  And yet on a third hand (perhaps there’s some sort of herbal remedy that can help me with that problem), for many ISPs, our program is their only whitelist, so clients who are above board, even if in a grey industry, may have no other option.

So is it our place to legislate morality, or should we just focus on what’s legal and what’s not legal?  How much accountability do clients bear for content that shows up in their emails from advertisers?  For example, and I’m making this up, what do we do if a men’s health magazine that’s a client has links in its email newsletters that are placed by an affiliate network that click through to a pornography site?  What if the pornography in question is legal in one country but not another?  How much time and energy should we spend vetting clients before we take them on?  Or monitoring them around these issues once they’re a client?  Does it matter which product they’re using?

I’d love feedback from the outside world (or the inside world) on how we should think about and handle these issues.

Drawing the Line:  Where We Come out

In the first post in this series, I laid out a dilemma we’ve had internally at Return Path in recent months: whether and how we accept clients who are in “grey” businesses like alcohol, pornography, and neutriceuticals, and whether that applies uniformly across all of our products (software vs. consulting vs. whitelist). In the second post, I reposted a summary of all the comments we received from readers. Now comes the fun part — the so what.

We had a good series of conversations internally on this issue that included some very spirited debate. Here’s where we come out.

First, we drew a distinction between three types of potentially “troublesome” clients: those whose businesses are illegal, or who advertise or sell illegal products; those whose businesses are involved in litigation around email, data, privacy, or security; and those whose businesses are in the grey area, or what we called in our discussions “morally hazardous.” In the end, we decided that for us, there’s no difference by type of product in terms of how we handle the situation. But each class of client has its own issues as well as enforcement mechanisms.

Let’s start with the easy one. Clients who break the law or whose businesses encourage others to do so have no place in our company. The challenge here is more on the edge cases — what about companies whose products or advertising are sometimes illegal (by geography or by age of target audience)? I will come back to that topic.

Next, we move on to those companies who are involved in email-related litigation. We added this category to our thinking because we view ourselves as advocates for end users, the champions of good, high quality email. Ultimately, the decision about whether or not to take on a client who is involved in email-related litigation is subjective. One example of a client we would take on is a very reputable company that has a single instance of a CAN-SPAM violation or investigation by the FTC. But there are other companies who are in much deeper. I will somewhat impolitely refer to them as “pissing in the pool.” As advocates for good email and as stewards of the email ecosystem, we can’t in good conscience allow some of these people to be clients, even of our software, if they have the potential to use the software for evil and not for good. Of course, once the litigation is finished we can re-assess, assuming the company was found to not have violated any laws.

Finally, the tough category, the “morally hazardous.” There certainly is something that resonates with us around one user’s comment that, to paraphrase, if you’re not comfortable telling everyone around the dinner table that you work for Client X, you shouldn’t work for Client X (or, Client XXX, as it were). But at the end of the day, legislating morality is impossible to get right for everyone, at every time. We think it’s not our business what kind of legal business our clients are in. In fact, we go so far as to say that as advocates for end users, our criteria around which clients to accept should be as objective as possible — that is to say, much more around their email reputation (how much do users like the content) than about some arbitrary judgment about what’s right and what’s wrong. We feel like as long as we maintain our policy of allowing employees to opt-out from working with clients or seeing clients’ content that makes them uncomfortable, we’re in as good shape here as we’re going to be.

Of course, that’s not to say we won’t, on a case-by-case basis, turn down a client because of their business. We aren’t a public utility. We have the right to walk away from a client for any reason (or, not to put too fine a point on it, no reason at all). But as a matter of policy we’ve decided to focus on email practices as a basis for who we work with and leave questions of morality of certain types of business aside.

As a final note, we clarified our policies for vetting and enforcing these standards. These do differ a bit by product. For our by-application whitelist, Sender Score Certified, we will continue to ask questions around the types of products and content that prospective clients include or link to in their emails. We will perform extra pre-client research on clients that check a number of boxes on the application that indicate they might be in a grey area or are involved in litigation. We will ask clients to self-certify their goodness. We will perform spot audits of these clients to make sure they stay in compliance with the things that are impossible to automatically monitor, even those tricky ones which are “sometimes legal.” And we will not be shy about terminating those who aren’t.

For our software and professional services, we have a “client vetting” document that asks some of those same questions, and against which we will research and audit as appropriate. For clients of our professional services, we require that sales/client services fill out this document 100% of the time for our standards and compliance team to review. For software clients, we leave it up to sales/client services management to flag the cases where there might be an issue and to run only those clients through the same vetting process.

I think that about wraps this topic up, at least for now. We do our best on this stuff, but it’s tricky, and I have no doubt that however we handle these situations, we will upset someone. I appreciate everyone’s input on this, and I welcome more by commenting below.

Executive and Closed Sessions

Brad has a good post up about what he calls “closed sessions” in Board meetings — time at the end of the meeting reserved for a conversation with Board members ONLY, no other observers or non-Board management.  While we differ in terminology, I agree completely with the sentiment and with his logic.

We call the part of the meeting that Brad describes the Executive Session.  We’ve always done them.  And the Board and I find it incredibly useful, and a good practice, even if there are no contentious or puzzling issues during a meeting.  Not that our Board holds back much, but the Executive Session is a good time for us to connect 100% freely about management issues as well as elements of business strategy and performance that might be better hashed out without others present.

We also have an additional part of the meeting at the very end which we call the Closed Session.  This part of the meeting has NO MANAGEMENT in it, even me, although I’m Chairman of the Board.  This time allows the other directors an even greater degree of freedom to discuss the business or my performance without worrying about saying something in front of me — and without hearing my opinion.

Both sessions are incredibly valuable parts of high functioning Boards.

Book Short:  Just One Minute

What The One Minute Manager does for basic principles of management and goal setting, The One Minute Manager Meets the Monkey does for delegation.  Both are blessedly quick reads (the classic “airport” book), and Ken Blanchard really nails some of management’s most critical components with simplicity and grace.

I’m a fan of the One Minute Manager school, and it does work well for some of the basics, but it has its limitations in terms of how broadly it can be applied.  My colleague Whitney McNamara‘s words in an email to me a few months back say it all:

OMM has actually been useful.  I have to agree that it’s got a bit of a “Jonathan Livingston Seagull” mystical simplicity thing going, but as you say, simple is sometimes what works best.

It’s really strong in that the basic lessons are at root so simple that they’re easy to forget about day to day…having them articulated in a similarly simple way, so that they stick at the top of mind easily, is nice.

The other side of that is that it presents such a simplified, best-of-all-possible-worlds sort of scenario that I did sometimes find myself wanting to set fire to the OMM’s office building and scream “let’s see you deal with *this* in 60 seconds, buddy”…but on balance a pretty good experience. 🙂

In the end, it’s not that good management is easy — but it can be quick and relatively painless if done well and regularly.