Memory Lane or Dark Alley?

We had an interesting meeting today.  A small group of the old-timers at Return Path, including one of our founders who doesn’t work at the company any longer, convened a summit to brainstorm ways to reinvent our original, original business, Email Change of Address (ECOA).

For those of you who don’t know what it is, ECOA is a very simple idea — that people who change email addresses need help updating their personal and business contacts, and also their most trusted commercial email newsletter relationships.  It’s a free service for consumers, and a paid service for opt-in email marketers and publishers who use our service to reacquire their customers with renewed permission and a shiny new email address.

When we created ECOA in 1999, we were sure it was the proverbial $100 million idea (what idea wasn’t in 1999?).  More than six years later, the product is a success and profitable, but it never took off with that explosive growth we all imagined early on.  Return Path has grown a lot since then, both organically and through M&A, and since about 2002 or early 2003, we basically put the ECOA business on “auto-pilot,” tending to it as needed and making sure it still worked well for consumers and clients and was adequately competitive in the market, but no longer investing meaningfully in its growth.

Now that we’re much larger and have the time and resources to put into it, we decided earlier this year to pay some attention to our neglected first child and see what we could do with it.  Today’s meeting was the first step, and boy was it interesting.

So I can’t decide whether the process of preparing for and going through this meeting was like a pleasant walk down Memory Lane…or a scary run through a Dark Alley late at night.  It was fun having a conversation about a part of the business that was so important to us at one time in our lives (it was all we had!), and the group of us were literally reminiscing in the meeting about all the different thoughts and ideas we had for the business over time, as well as about different former colleagues who worked with us on the business.  At the same time, it was pretty painful to look at some of our original projections for market size and of course business size — not to mention some of the marketing efforts, Powerpoint templates, logos, and names that fell by the wayside.

The good news is, either way, we do have lots of great ideas for how to move the ECOA business forward con gusto…so look for more news on this front as the year unfolds.

(This blog post was first published as an article in Entrepreneur Magazine on April 15.)

Creating strong boards can help propel a board forward. Weak and ineffective boards hold a company back.

As a CEO, one of the most important (yet overlooked) tools in the playbook is building and leading a board of directors. Throughout my 20+ years of entrepreneurship, I’ve led four companies (including Bolster, where I’m a co-founder and CEO today) and served on eight boards. I’ve learned that strong boards can help propel a company forward and I’ve also witnessed how weak and ineffective boards can hold companies back. Mediocre or mismanaged advice, plus lack of accountability, can do long-term damage to a business as well.

Drawing from personal experience and anecdotes from dozens of Bolster’s client CEOs, here are some tried and true “Seven Habits of Highly Effective Boards.”

Habit 1: Begin with the board in mind

A lot of CEOs treat board curation as an afterthought, which means that boards tend to consist largely of who happened to be in their network at the company’s inception: investors. CEOs also tend to treat their boards as a distraction or an annoyance. Both of these lines of thought are problematic. 

Boards should be viewed as a CEO’s second team (along with their management team), as a strategic weapon that helps the company succeed and as an opportunity to bring new voices and perspectives. Research has shown the more independent and diverse a board is, the better it performs.

Habit 2: Be proactive about board recruiting

Devote as much focus to building a board as to building the executive team. This process is time-consuming and can’t be delegated to anyone else. Aspire to reach people who may feel out of reach. Asking someone to join the board is a big honor, so that ask becomes a good calling card. When recruiting, interview as many contenders as possible, don’t be afraid to reject those who aren’t a good fit and have finalists audition by attending a board meeting. Source broadly, too. Diversity is really important for many reasons; challenge any recruiter, agency or platform to surface diverse board candidates.

Habit 3: Keep your board balanced using the Rule of 1s

Whether it’s a three-person startup board or a seven-person scale-up board, it should include representation from all three director types: investors, management directors and independents. A few basic principles on board composition that work well are what I call the Rule of 1s: First, boards should include one, and only one member of the management team: the CEO. Even if co-founders or C-level managers are shareholders, don’t burn a board seat for a perspective that you have access to regularly. Second, for every new investor to the board, add one independent director, which is the biggest opportunity to introduce external perspectives. If your board gets too crowded with subsequent funding rounds, ask one or more investors to take observer seats to make space for independents. And don’t be afraid to change your board composition over time. Companies are dynamic and boards should be, too.

Habit 4: Cultivate mutual accountability and respect

While a board might seem intimidating, work past the power dynamic and push toward collaboration and mutual accountability. To ensure board members are prepared for meetings, keep commitments and leverage their networks, set the example by demonstrating preparation, consistency and reliability. By regularly delivering pre-read materials to the board several days in advance, the board will build a new habit. By soliciting feedback from board members after each meeting (and even offering them feedback), you’ll show the board that you’re listening. Over time, they’ll lean in, too.

Habit 5: Drive intellectually honest discussions

Even on the healthiest leadership teams, it can be scary to disagree with or challenge a sitting CEO (after all, they are still the one in charge!). But this power dynamic flips in a boardroom, which gives that group a unique opportunity to push and challenge business assumptions. While it may be tempting to look for board members with softer dispositions, it can be more beneficial to have tough, direct board members who aren’t afraid to express their opinions, but who are also good listeners and learners. My favorite discussions are conversations where I’m pushed to consider a different direction. It helps get more done, surfaces better ideas and increases the effectiveness of the company.

Habit 6: Lean in on strategic, lean out on tactics

Even board members who are talented operators have a hard time parachuting into any given situation and being super useful. Getting 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 and ecosystem. This is an easy habit to reinforce in meetings. If board directors drift toward getting too tactically in the weeds, that’s great feedback to offer after the meeting.

Habit 7: Think outside the box

Good board members understand all the pieces on the chess table; great board members go one step further and pattern match to provide advice, history, context and anticipated consequences. This is an enormous benefit to CEOs focused on the minutiae of the day-to-day, particularly if a business operates in a trailblazing industry where many of the rules may not yet be written. As a CEO, if you’ve never seen something first hand before, it’s hard to get clarity and external perspectives, which is why it’s crucial that great board members bring pattern recognition and “out-of-the-box thinking” to their role.

At the end of the day, boards are there to support and direct a company. There’s no perfect formula, but by implementing these steps with a few healthy habits, CEOs can cultivate strong, dynamic boards for their companies.

People talk a lot about Imposter Syndrome — “What am I doing here? I’m not qualified to do X at all” regularly when it comes to women and people of color in the workplace. That is a real thing. It shouldn’t in any way be discounted. It’s painful to go through and painful to watch.

I’d guess that 9 our of 10 founders have Imposter Syndrome at least once during their founder journey. Maybe it’s even more like 99 out of 100. And I bet most of them have it more than once…some regularly. This may be even more true for founders from underrepresented populations, but it happens regardless of demographic.

Being a founder is inherently unnatural. Seeing the world through a different lens, inventing something, and being crazy enough to act on it, quit your job, raise capital, and convince other people to quit their jobs to join you on your journey is a tall order no matter who you are.

No founder’s journey exists without speedbumps and moments where things aren’t working and you feel like your company is going to die a horrible and painful (and worse, public) death – what my former Board member and friend Scott Weiss famously calls the WFIO moment (We’re F’d – It’s Over), popularized by Ben Horowitz in The Hard Thing About Hard Things.

Founders, it’s ok. We’ve all been there. Take a step back. Solve the problem. Change the approach. You’re not in the wrong place. You’re just having a bad moment. And most important, remember, you’re not alone.

Who Wants to Get Hit by a Bus, Anyway?

Fred had an accurate if somewhat morbid posting today about succession planning, one of the many higher-order HR tasks that small entrepreneurial companies are particularly bad at.  He’s completely right — for one example in our industry, you only have to look back about 9 months or so to Phil Goldman’s shocking death to see the impact it had on Mailblocks.  I’ll have to post on succession planning in a startup in more detail sometime soon.

Yes, They Are THAT Important

Our enterprise spam filter has been down for about a day as we reconfigure some servers here.  It has been just this side of crippling, especially travelling and getting spammed to death on my Treo.

Spam filters have become good enough (though still not perfect on the false positive side, of course) and prevalent enough, that I had forgotten just how important a role they play in today’s corporate IT environment.  We’d be in really sorry shape without them!

As we wrote in Bolster’s Founding Manifesto, one of the reasons we started Bolster was to create a new way; a faster, easier, and more cost-effective way, for startup and scaleup CEOs to grow their boards of directors and make them more diverse.

There’s a lot of research out there that the more independent a board is, the better it performs for companies — and that there’s a high degree of correlation between more independent boards and higher performing companies as well. There’s also a lot of research out there that shows that teams which have diversity of gender and race/ethnicity perform better. And everyone who has ever been on a high-functioning board of directors knows that a board is a team.

These facts are well known, yet it is still the case that most private company boards are overwhelmingly made up of founders and investors who are still largely white and male. I believe that the lack of independence and diversity on boards is a big miss for the whole startup ecosystem, and it’s a part of the startup game that we at Bolster want to help change.

Startup boards are tricky things. One of the very unique aspects of a CEO’s job that sets it apart from other executive positions is building and leading a board of directors. But most startup CEOs have either little or no experience building and leading a board, so that part of the job tends to default to a “because that’s the way I assume it’s always been done” kind of task. Of course, if you’re not intentional about building and managing a board, you’re likely to get lousy results. 

Building, shaping, and leading a world class board is one of the single most important things startup CEOs can do to help their businesses thrive and become industry leaders. It’s on par with building and leading an executive team. I’ve seen amazing companies held back by weak and ineffective boards and investor syndicates, and I’ve seen so-so companies succeed because the strategic advice, experience, and accountability coming out of the board room drives the management team in extraordinary ways.

So how is Bolster helping startup CEOs change the game with respect to Boards? We are doing three things. 

First, as you know, what gets measured gets managed. Our first-of-its-kind Board Benchmark application will soon produce an industry standard set of data around private company boards. You can’t find data on private company boards but we’ll soon have important data like size, composition (independents/management/investors), independent director compensation and diversity (gender/race-ethnicity/age). This will help answer questions that I know I have had many times over the years as a CEO such as 

• How big should my board be at this stage? 
• How many independent directors should I have? 
• What is the right profile of an independent director? 
• How many options should I give a board member? 

Starting next week, we’re opening up our Board Benchmark application to any company who creates a free Bolster account. It will tell us a lot about the baseline across the ecosystem, and it will answer a lot of questions startup and scaleup CEOs have but can’t get answers to. Although this is an ongoing real-time benchmark tool, I’ll post some results here when we have enough critical mass to start reporting out.

Second, Bolster is in the talent business, and helping match VC-backed companies with a strong diverse slate of board candidates who are well-matched with their company is at the core of our business. We are already working on many searches for independent board members, and we’ll only be doing more of them as our client base and member base grow.

Finally, this blog post is the beginning of a whole series of posts about startup boards that we hope will demystify them a bit and help change the world’s thinking about how to grow them. Some of the material I will borrow from other blog posts I’ve written, or from the Board of Directors section of Startup CEO. Some will come from other influential VC and CEO bloggers and from Brad Feld and Mahendra Ramsinghani’s book Startup Boards. But much of the content will be new. And because Bolster is a two-sided marketplace, roughly half of the content will be aimed at startup CEOs and the other half at executives who are interested in serving on boards and aren’t sure how to get from where they are today into a board room. We’ll be sending out all the CEO posts as an eBook to CEOs who complete the Board Benchmark study, and all the Member posts as an eBook to Bolster members who fill out their Board profiles. I’ll post both of those eBooks here eventually as well.

For CEOs, the topics we will cover include 

• The purpose of a board
• Size and composition on boards
• Board evolution & turnover
• Diversity in the boardroom and the importance of appointing first-time directors
• What to look for in a director
• How to recruit and interview directors
• How to onboard directors, especially first time directors
• How to compensate directors
• How to build a director bench or Advisory Board
• How to evaluate your board

For executives searching for a board role, the topics we will cover include 

• What startup corporate boards look like
• How to prepare yourself to get on your first board
• Should you serve on an advisory board?
• How to interview for a Board role
• What you need to know about board compensation
• How to approach your first board meeting
• How to think about corporate governance as a board member
• How to be a great board member
• How to give advice or difficult feedback as a board member
• Making sure your voice is heard during a board meeting
• How to know if you’re doing a good job as a board member

We believe that boards can make or break a company and we intend to chart a new course for startup boards. I look forward to sharing thoughts and data with you on that topic in the weeks to come.

I haven’t done a book review yet on this blog because I haven’t found a very relevant one. I will do more as I go here — I’ve actually read a few pretty useful business books lately — but there’s no better book to kick off a new category of postings here than the one I just finished: The MouseDriver Chronicles: The True-Life Adventures of Two First-Time Entrepreneurs.

The book details how two freshly-minted Wharton MBAs skipped the dot com and investment banking job offers to start a two-person company that produced the MouseDriver (a computer mouse shaped like a the head of a golf club) back in 1999-2000. It’s a great, quick read and really captures the spirit of much of what I’m trying to do with this blog, which is talk about first-time CEO issues, or company leadership/management issues in general.

Although it’s not about an internet business, the book also has an interesting side story, which is the powerful impact that email had on the MouseDriver business, with an email newsletter the entrepreneurs started that developed great readership and ultimately some viral marketing. Sort of like a blog, circa 1999.

Thanks to Stephanie Miller at Return Path for giving me the book!

I was having breakfast with the CEO of another SaaS company the other day, as I often do to network.  He was telling me about his experience working with his company’s new Private Equity owner.

There are always a mix of pros and cons that come with any particular shareholder, Board member, or owners, of course.  In his case, my fellow CEO was bemoaning the 29-year old associate who acted like a know-it-all in every Board meeting.  Lots of CEOs have been there.  There’s a lot of value you can get from an associate or VP-level person at an investor who is the Master of the Spreadsheet and who has access to a lot of data about your company.  And there is certainly a lot of value to be gained from investors with large portfolios of similar companies who can identify learnings from experience you haven’t had as a CEO and help you apply that experience thoughtfully to your company in any given situation.  In The Value and Limitations of Pattern Matching, I quoted my father-in-law, who noted once that When you hear hoof beats, it’s probably horses. But you never know when it might be a zebra.  I am still a firm believer that it’s the “thoughtful application” that matters as much as recognizing the pattern.

But this breakfast conversation led me to another conclusion, which is less about pattern matching and more about the pattern matcher.  And that is:

You don’t know how to drive a car because you know how to read a map

Being a Master of the Spreadsheet is a great starting point to coming up with ideas and insights for a business.  Quantitative analysis can tell you a lot of things, including a lot of things that you wouldn’t be able to get on instinct or experience alone, like slow, subtle changes in customer behavior, customer-level profitability, the impact of pricing changes, or compound effects of salary or benefit changes on a cost structure over time.  Think of quantitative analysis a bit like a road map.  It can show you the shortest distance and combination of roads and turns to get from Point A to Point B.

But quantitative analysis stops there.  It is not the same as actually getting yourself from Point A to Point B.  Driving a car in and of itself is a skill that requires a lot of learning and practice.  And it certainly doesn’t forecast traffic or road hazards that require a last minute detour.  Being right about what roads to take is a lot less important than actually getting yourself to the destination safely and in a timely manner.  The value of having experienced executives operating a business is those things – the actual driving of the car.  The knowing of the customers or the employees.  The skill of managing change and emotions.

At the end of the day, there’s value in both ends of the spectrum – the reading of the map and the driving of the car.  As long as the two sides agree that there’s value to both tasks and that the two sides bring different expertise to the table, there’s a great partnership to be struck.  But too often these days I hear about investors who think that reading the map is all that needs to happen for a company to be successful.  Until someone comes up with the self-driving car of management, this metaphor should hold!

I’ve gotten to know a number of Bolster members over the last few years, and one who I have come to appreciate quite a bit is Tim Porthouse. I’m on Tim’s email list, and with his permission, I’m reprinting something he wrote in his newsletter this month on the topic of CEO engagement in politics and current events. As you may know, I’ve written a bunch on this topic lately, with two posts with the same title as this one, Should CEOs wade into Politics (part I here, part II here). Thanks to Tim for having such an articulate framework on this important subject.

Your Leadership Game: “No Comment.”

Should you speak up about news events/ politics?

Most of the time, I say, no!

Startup CEOs feel pressure to speak up on news events: Black Lives Matter, Abortion, LBGTQ+ rights, the conflict in Israel/Palestine, Trump vs. Biden. Many tell me they feel pressured to say something, but are deeply conflicted.

Like you, I am deeply distressed by wars, murder, restrictions on human rights, bias, and hate. But if we feel something, should we say something?

Before you speak up, ask the following questions:

1.      Mission relevance. Is your startup’s success or mission on the line? Are customers or employees directly impacted? Example: It makes sense for Airbnb to advocate when a city tries to ban short-term rentals. It makes sense to advocate for your LBGTQ+ employees when a state tries to restrict their rights.

2.      Moving the needle. Will speaking out change anything? If you “denounce” something or “take a stand,” what really happens? Example: If you have employees in a state banning abortion and you tell them your startup will support them as much as the law allows, this could create great peace of mind for employees. But if your startup does not operate in Ukraine or Russia, then denouncing Russia does little (and Russia does not care!)

3.      Expertise. Do you have a deep understanding of the situation? It’s usually more complicated than it appears, especially at first. Once you speak out, you have painted yourself into a corner you will be forced to defend.

4.      Precedence and equivalence. If you issue a statement about today’s news event, will you react to tomorrow’s event? Why not? Where do you draw the line?Someone will be offended that you spoke up about X but not Y.

5.      Backlash. Are you ready to spend significant time engaging with those who disagree with you?It can get ugly quickly, and mistakes can be costly. Plus, the American public is tiring of business leaders commenting on the news.

6.      Vicarious liability. Who are you speaking for? When you say, “Our startup denounces X”?Does the whole company denounce it? You don’t know, and probably not. Does the Leadership Team? They may feel pressured to support you. What you are really saying is, “I denounce X!” OK, great, then say it to your friends and family. Leave your startup to talk about business.

If your answers are “yes,” – then speak out.

If not, I recommend keeping quiet.

In my opinion, our job is to build great companies, not debate current events.

By not speaking out, you can say, “We don’t talk politics here.” You can shut down any two-sided arguments at work and say, “Let’s get back to work,”removing a big distraction. Remember when employees protested because Google was bidding for Pentagon contracts?

I realize that you will be challenged to make a statement, that, “Saying nothing is unacceptable/ complicit.” But whoever challenges you will only be satisfied if you support their view.

If you still want to speak out, I respect your choice. Some of you will be angry with me for writing this, and I accept that. I’m asking you to think carefully before you make a statement.

Come Fly With Me

I do a lot of travel for work.  That means I spend a lot of time on planes, some of which is “wasted” – or at least time that can’t be productive for work in the traditional sense of being connected, or in a lot of cases, of even reading.  One thing I’ve always appreciated in my career but have grown even more attached to of late is traveling with colleagues.  Any time I have an opportunity to do so, I jump on it.

First, I find that I get solid work time in with a colleague in transit.  A check-in meeting that isn’t rushed with a hard stop, interrupted by the phone or visitors, and in-person.

Second, I find that I get more “creative” work time in with a colleague on a flight, especially a long one.  Some of the time that isn’t in a structured meeting invariably turns to brainstorming or more idle work chatter.  Some great ideas have come out of flights I’ve taken in the past 11 years!

Finally, my colleague and I get more social time in than usual on a plane.  Social time is an incredibly important part of managing and developing personal connections with employees.  Time spent next to each other in the air, in an airport security line or lounge, in a rental car, “off hours” always lends itself to learning more about what’s going on in someone’s life.

Don’t get me wrong – even when I travel with someone from Return Path, we each have some “quiet time” to read, work, sleep, and contemplate life.  But the work and work-related aspects of the experience are not to be ignored.

Self-Discipline:  Broken Windows Applied to You

Just as my last post about New Shoes was touching a bit of a nerve around, as one friend put it, "mental housecleaning," my colleague Angela pointed me to a great post on a blog I've never seen before ("advice at the intersection of work and life" — I just subscribed), called How to Have More Self-Discipline.  Man, is that article targeted at me, especially about working out. 

I think the author is right — more discipline around the edges does impact happiness.  But it also impacts productivity.  Not just because working out gives you more energy.  Because having your act together in small ways makes you feel like you have your act together in all ways.  As the author notes (without this specific analogy), it's a little like the "broken windows" theory of policing.  You crack down on graffiti and broken windows, you stop more violent crime, in part because the same people commit small and large crimes, in part because you create a more orderly society in visible, if sometimes a bit small and symbolic, ways.

I agree that the best example in the "non work" world is fitness.  But what about the "work world"?  What's relevant around self-discipline for professionals?  Consider these examples:

– A clean inbox at the end of the day.  Yes, it's the David Allen theory of workplace productivity which I espouse, but it does actually work.  A clean mind is free to think, dream, solve problems.  The quickest path to keeping it clean is not having a pile of little things to deal with in front of it, taking up space

– Showing up on time.  It may sound dumb, but people who are chronically late to meetings are constantly behind.  The day is spent rushing around, cutting conversations short — in other words, unhappy and not as productive.  The discipline of ending meetings on time with enough buffer to travel or even just prepare for the next meeting so you can start it on time (and not waste the time of the other people in the meeting) is important.  Have too many meetings that you can't be at all of them on time?  Say no to some — or make them shorter to force efficiency.  There's nothing wrong with a 10-minute meeting

– Dressing for success.  We live in a casual world, especially in our industry.  I admit, once in a while I wear jeans or a Hawaiian shirt to work — even shorts if it's a particularly hot and humid day.  (And even in New York, not just in Boulder.)  But no matter what you wear, you can make sure you look neat and professional, not sloppy.  Skip the ripped jeans or faded/frayed/rock concert t-shirt.  Tuck in the shirt if it's that kind of shirt, and wear a belt.  The discipline of "dressing up" carries productivity a long way.  Want to really test this out at the edges?  Try wearing a suit or tie one day to work.  You feel different, and you sound different

– Doing your expenses.  Honestly, I've never seen an area where more smart and conscientious people fall apart than producing a simple expense report.  Come up with a system for it — do one every week, every trip on the plane home, every time you have an expense — and just take the 5 minutes and finish it off.  Sure, expenses are a pain, but they only really become a pain and a millstone around your brain when you let them sit for months because you "don't have time" to fill them out, then you get accounting all pissed off at you, and the project's size, complexity, and distance from the actual event all mount

– Follow rules of grammar and punctuation.  Writing, whether for external or internal consumption, is still writing.  I'm not sure when everyone became ee cummings and decided that it's ok to forget the basic rules of English grammar and punctuation.  Make sure your emails and even your IMs, at least when they're for business, follow the rules.  You look smarter when you do.  Maybe — maybe — with Twitter or SMS you can excuse some of this and go with abbreviations.  But I wouldn't normally consider a lot of those formal business communications

I could go on and on, but I think you get the idea.  A little self-discipline goes a long way at work (and in life)!