Over the past several months, I’ve published two series of posts on the Bolster blog about Boards. The first series is designed to help CEOs better understand how to build, diversify, and scale their boards of directors. I’ll write about the second one next week. Both series of posts will feature in the second edition of Startup Boards, a book originally published in 2014 by Brad Feld and Mahendra Ramsinghani. The second edition, which is also co-authored by me, will be out late this year or early next year.

As I’ve gone about building our business at Bolster, including leading several dozen board searches for companies of all sizes and stages from pre-revenue to public, I’ve noticed that there are still a lot of questions among company leaders about board-building best practices. Without a lot of documentation and analysis about private company boards, most startup CEOs learn about building and managing boards through trial and error. As a result, this critical component of corporate governance is often under-utilized. Directors’ skills and networks are under-leveraged, term lengths are rarely re-negotiated, and board diversity becomes an afterthought.

This is why I set out to publish a comprehensive look at building boards, written from one CEO to another. You can read the full series here:

• The New Way to Scale A Board of Directors
• The Purpose of a Board
• Size and Composition of Boards
• Board Evolution and 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 Independent Directors
• How to Build a Director Bench or Advisory Board
• How to Evaluate Your Board

The team at Bolster also compiled all of these posts into an eBook you can download by clicking on this link, entitled How to Build Your Board. No matter where you are in your journey as a CEO or company leader, I hope this is a resource and reference for you to look back on over time.

By the way – if you’d like to get access to more content like this or start a search for an independent director for your own board, you can sign up as a Bolster client here.

Blogiversary, Part VII

Today marks the seventh anniversary of OnlyOnce.  I haven’t marked the date with a post in three years, but here was my last such post (with links to prior posts in it).  In sum up until now, my reasons for blogging have been written up as:

• “Thinking” (writing short posts helps me crystallize my thinking)
• “Employees” (one of our senior people once called reading OnlyOnce “getting a peek inside Matt’s head)
• My book reviews help me crystallize my takeaways from books and serve as a bit of a personal reference library
• I like writing and don’t get to do it often

After seven years, though, I’m going to add another important point of value for me for writing OnlyOnce:  now, at 672 posts (including 27 that are scheduled but not yet posted – easy a record for me), this blog now serves as a repository for me of my own lessons learned, best practices, anecdotes, and aphorisms.  Thanks to Lijit, it’s easy for me and others to search.  Thanks to the new WordPress format and design by my friends at Slice of Lime, the categories and tagging make it much easier to navigate.

I probably get one question a week from a fellow CEO or prospective entrepreneur or employee that, instead of typing out an answer or setting up a meeting, I can actually just send a link as a starting point.  Sometimes there are follow-up questions, sometimes there aren’t.  But the blog is proving to be a very efficient form of documentation.

One of the new sections in the Second Edition (order here) that I’m excited to share is a deep dive with several chapters on selling your company.  The next few blog posts will share some of my thinking on the subjects as they’re arranged into chapters in the book.  For many startup CEOs the culmination of their life’s work is an exit of some kind (other than being fired!). Personally, there were a range of emotions surging through me when we got to the point of a sale and while the financial reward can be enticing, there are a lot of things that you start to think about, like all the things you created, all the offsites with your team, the good and bad times and, especially, the deep relationships you’ve developed over the years.

If you’re a founder entrepreneur who has led your company for several years, the odds are you have a significant amount of emotional investment in your company, too.  For many entrepreneurs, the company is a deeply embedded part of their identities as a human – right or wrong, for better or for worse. 

I said in the First Edition that entrepreneurship is full of extreme highs and lows and the most difficult thing to accept is when they happen at the same time. Nothing describes the process of selling your company more accurately than that saying because you’re gaining some financial reward, but you’re losing your life’s work. You’re also creating some chaos and uncertainty for all your employees.

One of the most important questions you can ask yourself is, “Am I ready to let go?” For me I used a simple litmus test to help answer that question and I used the answers to these four questions to figure out the sell-don’t sell dilemma:

• Am I having fun at work?
• Am I learning and growing as a professional?
• Is my work financially rewarding enough, either in the short-term or in the long-term?
• Am I having the impact I want to have on the world?

You can turn these questions into a scale if you want to be more sophisticated but there are two important points: one, you have to do it and two, you have to look at all four questions as really just providing one piece of information. If I walked into an executive team meeting and said, “I’m not having fun at work,” my team would probably look at me and say (or think to themselves), “Hey, buddy, suck it up.” They’d be right, but if you have low scores on all four questions, that tells a different story. 

So how do you know when it’s time to sell? Usually there’s an inflection point of some kind–either positive or negative. On the positive side, you can receive an out-of-the-blue inbound offer, something you never expected and believe me, that will get the juices flowing! Or maybe when you look two years out you realize that your company is at its highwater mark in valuation, so it becomes a timing issue. Sometimes you can have a major internal problem related to the cap table–a founder with a lot of stock needs liquidity or you need to push this person out of the company. Institutional investors can require liquidity too, and while it’s possible to buy out shareholders or create a debt / equity financing, you might think about selling the company instead.

Other points on selling your company that I make in the Second Edition revolve around who you sell to (financial buyer, strategic buyer) and what the likely outcome of those types of sales are for you and your employees. You’ll need to brace yourself, your team, and your company, and your family for a major impact–the sales process is disruptive, non-linear, and intense and it’s not done until the final agreement is signed. 

Above all else, There is no right or wrong answer here about selling your company.  But there probably is a right or wrong answer for YOU.  That’s the most important thing to think through, deeply, at the early stages of working on selling your company.

My father-in-law, who is a doctor by training but now a health care executive, was recently talking about an unusual medical condition that someone in the family was fighting.  He had a wonderful expression he said docs use from time to time:

When you hear hoof beats, it’s probably horses. But you never know when it might be a zebra.

With experience (and presumably some mental wiring) comes the ability to recognize patterns.  It’s one of those things that doesn’t happen, no matter how smart you are, without the passage of time and seeing different scenarios play out in the wild.  It’s one of the big things that I’ve found that VC investors as Board members, and independent directors, bring to the Board room.  Good CEOs and senior executives will bring it to their jobs.  Good lawyers, doctors, and accountants will bring it to their professions.  If X, Y, and Z, then I am fairly certain of P, D, and Q.  Good pattern recognition allows you to make better decisions, short circuit lengthy processes, avoid mistakes, and much better understand risks.  The value of it is literally priceless.  Good pattern recognition in our business has accelerated all kinds of operational things and sparked game changing strategic thinking; it has also saved us over the years from making bad hires, making bad acquisitions, and executing poorly on everything from system implementations to process design.  Lack of pattern recognition has also cost us on a few things as well, where something seemed like a good idea but turned out not to be – but it was something no one around the Board table had any specific experience with.

But there’s a limitation, and even a downside to good pattern recognition as well.  And that is simple – pattern recognition of things in the past is not a guarantee that those same things will be true in the future.  Just because a big client’s legal or procurement team is negotiating something just like they did last time around doesn’t mean they want the same outcome this time around.  Just because you acquired a company in a new location and couldn’t manage the team remotely doesn’t mean you won’t be able to be successful doing that with another company.

The area where I worry the most about pattern recognition producing flawed results is in the area of hiring.  Unconscious bias is hard to fight, and stripping out markers that trigger unconscious bias is something everyone should try to do when interviewing/hiring – our People team is very focused on this and does a great job steering all of us around it.  But if you’re good at pattern recognition, it can cause a level of confidence that can trigger unconscious biases.  “The last person I hired out of XYZ company was terrible, so I’m inclined not to hire the next person who worked there.”  “Every time we promote someone from front-line sales into sales management, it doesn’t work out.”  You get the idea.

Because when you hear hoof beats, it’s probably horses.  But you never know when it might be a zebra!

A New Path Forward

Welcome to the world, Path Forward, Inc.!

I’m thrilled to announce the launch today of Path Forward, a new non-profit with a goal of empowering millions of women to rejoin the workforce after taking time out for childcare. We are launching today with a Crowdrise campaign.   See more about that below.  And we launched with a bang, too – the organization is featured in this really amazing story on Fortune.

The concept started at Return Path two years ago, as I wrote about here and again here, when our CTO Andy Sautins came to me with a simple but powerful idea of creating a structured program of paid fellowships with training for women who want to reenter the workforce but find it difficult to do so because of rusty skills, lapsed networks, or societal bias. We expanded the program later that year with partner companies ReadyTalk, SendGrid, MWH Global, SpotX, and Moz, as I wrote about here.  The response from both participants and companies has been nothing short of amazing.

The day after I put up that last post about v2 of the program, a human resources leader at PayPal gave me a call and asked if we could help them structure a program for their engineering organization, too.  That’s when it struck me that the idea of midcareer internships as one means of providing an on-ramp to the paid workforce for people who’d been focused on caregiving could work for many companies, and also that for this program to work and scale up, it couldn’t be an “off the side of the desk” project for the People Team at Return Path.  So we decided to create a new company separate from Return Path to carry out this important work.  And we decided that with a practical, but social mission, it should be a non-profit, dedicated to creating and managing networks of companies offering opportunities to many more people.

To date, the program has served nearly 50 participants (mostly women, but a couple of stay-at-home dads, too!) and 7 companies in 6 cities around the world, producing an impressive 80% hire rate.  The participants who have been hired by us and our partner organizations have made impressive contributions to their companies’ businesses and cultures.  The companies have benefitted from their experience and passion.  That’s what I call product-market fit.  Now it’s time to officially launch the new organization, and scale it up!  Our BHAG (Big Hairy Audacious Goal, in the language of Jim Collins) is that within 10 years, we want to serve 10,000 companies and 1 million women and men.  We want to reduce the penalty that caregivers face when they take time away from paid work.  We want to transform lives by getting people who want to work, back to work in jobs that leverage all their many skills and talents.  We want to help companies tap into an incredibly important but overlooked part of the talent pool to grow their workforces.  We want to change the world.

We’ve been able to assemble a strong Board of Directors to lead this effort.  Joanne Wilson, often better known as Gotham Gal and the founder of the Women’s Entrepreneur Festival, is joining me as Board Co-chair. Joanne is a force to be reckoned with in championing women founders in tech.  Brad Feld joins our Board with great credentials as an early-stage investor, but more importantly he’s served for more than 10 years as Board Chair of the National Center for Women and Technology.  Media luminary and investor Cathie Black was most recently the President of Hearst Magazines having previously served as President and Publisher of USA Today.  Cathie has been the “first” woman many times and has broken her share of glass ceilings.  Rajiv Vinnakota is the Executive Vice President of the Youth & Engagement division at the Aspen Institute and prior to that was the co-founder and CEO of The SEED Foundation, a non-profit managing the nation’s first network of public, college-preparatory boarding schools for underserved children which he started and successfully scaled up for more than 17 years.  Cathy Hawley, our long-time VP of People at Return Path, gets (though often deflects) the lion’s share of the credit for conceiving and championing the original return to work program at Return Path.  It is, truly, an embarrassment of riches. We are so thrilled to have them all on board Path Forward’s Board.

On the staff side I’m also pleased to announce that one of my long-time executive lieutenants at Return Path, Tami Forman, has accepted the role of Executive Director of Path Forward. I can’t think of anyone better for this role. Tami is the consummate storyteller, which every good founder and Startup CEO needs to be! More importantly she has been living and breathing work/life integration for eight years since the birth of her daughter (followed by a son). She is absolutely passionate about the idea that women can have jobs and families and live big lives. And, more importantly, she’s dedicated to the idea that taking a “break” (she and I agree it’s not a break!) to care for a loved one shouldn’t sideline anyone’s career dreams.

I can’t wait to see how far this idea can go. I truly believe this program can have a measurable, positive impact on thousands of companies across the country and the world.

Please join me and Tami and our talented Board on this journey.  Help us change the world.  There are three ways to participate:

• Click here if your company would like to learn more about having the Path Forward program in the future
• Click here if you would like to return to the workforce after a break and think a Path Forward fellowship might be a good, well, path forward for you
• And as a non-profit, we need financial help! Click here to contribute to our Crowdrise campaign, the goal of which is essentially a $500k “Series A” round (although it’s a non-profit, so this is a purchase of emotional equity, not actual equity) to move from product-market fit to a proven business model!

(Please note – we haven’t yet received word of our non-profit status yet from the IRS, though we expect it in the next couple of months.  As such, any donation now is not tax deductible until after the certification comes through.  While there’s some risk that we don’t gain non-profit status…we don’t think the risk is large.)

(This is the second post in the series… the first one When to Hire your first Chief Privacy Officer is here)

Most Chief Privacy Officers are fairly specialized, often coming from a legal or law enforcement background, but regardless of background I’ve found that ideal startup Chief Privacy Officers do three things particularly well.

First, a great Chief Privacy Officer will work to create educated evangelists inside the company.  Our Privacy team at Return Path, under Dennis Dayman’s leadership, had a lot of experience and industry certifications, but that experience was not something only for regulators and other companies, or only bragging rights within their team. They also took the time to make sure others in the company, especially in the product management and engineering teams, received some of that same training and those same certifications.  By not making the Privacy team a single point of knowledge or failure, Dennis was able to make Privacy part of our product strategy and offense as opposed to a mitigation or defensive function

A second ideal characteristic of a Privacy Officer is that they also handle the basics of InfoSec, in addition to privacy.  If you’re actually a security-related company or a massive consumer or financial organization, you may need a dedicated Chief Information Security Officer.  If you aren’t, then a good Chief Privacy Officer should be able to handle a number of the functions that a CISO would otherwise handle, especially on the policy and communication front.

And third, a great Chief Privacy Officer is an excellent communicator, both internally and externally, and they help connect you to the relevant members of your community or ecosystem.  When we had a sizable data breach on Thanksgiving Day about 10 years ago, our fractional head of privacy, Tom Bartel, was on the spot. He wrote emails and external blog posts that needed almost no review.  He was also instantly communicating with dozens of his counterparts at related companies so that the industry knew where we stood and what we were doing about the problem.  It was like an instant activation of an emergency response system!

Don’t wait until you have a data breach to hire a great Chief Privacy Officer because by the time you need one it will be too late.

(You can find this post on the Bolster Blog here)

What Convergence Really Means

Rebecca Lieb wrote a great column last week in ClickZ about Advertising Week and how disappointed she was in it.  The article is worth a read for many reasons, but there was one quote in particular that stuck out to me as I re-read it tonight.

Some people talk about convergence as the coming together of old media and new media.  Others talk about digial meeting analog.  Still others talk about the melding of cable, telco, Internet, and wireless.  A brave few even talk about direct marketing and brand advertising.

But Rebecca quoted the head of global advertising for American Express, who really nailed what convergence means in the world of media today — the convergence of advertising and publishing:

“No longer can we view our job as filling gaps between other peoples’ content,” said Scotti. “Soon, there won’t be gaps to fill because everything is content.”

Boy, isn’t that the truth?  And it’s not just the much-hyped world of user-generated content, YouTube, Facebook, MySpace, and blogs.

It’s as much about advertisers getting smarter and becoming content publishers themselves.  Think about any good email you get from a marketer.  What makes it good?  Sure, a nice discount, maybe free shipping, certainly a relevant offer based on your preferences and purchase behavior.  But the other thing that makes it good is the presence of content to surround and drive the marketing messages.  The applesauce around the pill, if you will.

It works.  We see it every day.  And we only see more of it happening in the future as consumers get smarter and more discerning about the brands with which they choose to interact.

Blogiversary

Next week will mark the one year anniversary of my blog (and for that matter, Brad’s blog).  It’s been a lot of fun, so I think I’ll celebrate by taking two weeks off and going to Europe with Mariquita (well, ok, I was planning on doing that anyway).

Even if no one read OnlyOnce, I’d be happy I’m writing it for all of the reasons I expressed here back in June.  But lots of people do read it, more and more every day.  In fact, an executive at Yahoo! who I met earlier this week actually quoted it to me — as Bruno Kirby said in When Harry Met Sally, “the first time someone has ever quoted me back to me before.”

In my very first posting, which explains the blog’s title and mission, I said I’d try not to be too extraneous with the material I post.  So I took a look through some stats this morning about the last year of blogging:

– Including this, I’ve written 131 postings, about one every three days

– Typepad doesn’t keep stats on blog topics/categories, so this is an estimate (and postings can be associated with multiple categories), but it looks like I’ve posted 6 times about books, 10 times about current events, 4 times about travel, 7 times about blogs, 9 times about “business” (whatever that means), 52 times about email/web/tech, 40 times about entrepreneurship, and 38 times about leadership/management.  So at least I stayed more or less on point.

– I’ve received a total of 125 comments, or less than one per posting (this is NOT a truly interactive medium!)

– I have about 1,000 regular readers, roughly 70% via RSS feed, 20% via email subscription, and 10% via live alerts or just regular web visitors

– My Amazon Associates link has generated about 150 sales for a total of $2,700 and about $170 in affiliate fees to me, which basically covers the cost of my Typepad subscription

Thanks to everyone who reads and comments.  Feedback is always welcome for year two!

Post 4 of 4 in the series of Scaling CPO’s- the other posts are, When to Hire your First Chief People Officer, What does Great Look like in a Chief Privacy Officer and Signs your Chief Privacy Officer isn’t Scaling.

You won’t have a ton of time to engage with the Chief People Officer but there are a few ways where I’ve typically spent the most time, or gotten the most value out or my interactions with them. So, you’ll need to capitalize during those few moments when you do get a chance to engage with the Chief People Officer.

I ALWAYS work with the CPO as a direct report.  No matter who my HR leader is, no matter how big my executive team is, no matter how junior that person is compared to the other executives. I will always have that person report directly to me and be part of the senior most operating group in the company.  That sends the signal to everybody in the company that the People function (and quite frankly, diversity, culture, and a whole host of other things) are just as important to me as sales or product. I guess that’s walking the walk, not just talking. If I’m not serious about diversity, about our core values, and about the people in the company, no one else will be either. So, I always have the CPO as a direct report.

A second way to engage with the CPO is to insist on hearing about ALL people issues. First, I am a very “retail-oriented” CEO, and I like to engage with people in the business—at all levels, in all departments, and in all locations.  So I like know what’s going on with people — who is doing particularly well and about to be promoted, who is struggling, who is a flight risk, who is going through some personal issue (good or bad) that we should know about. This isn’t prying into people’s lives, but a real way to engage with people beyond business and a way to show that you care about them as a person. Even more than just me wanting to be in the know, I want others in the company to have a deep level of awareness of our contributors. For example, in our Weekly Sales Forecast meeting at Return Path, because our head of People knew that I wanted to know about all these details on our employees, they insisted that all the other People Business Partners roll those issues up as well. That means everybody in the room was in the know as well.  It’s not just to have a better understanding of people, there’s a business case for knowing what’s going on at a very detailed level and the number of issues we nipped in the bud, the number of opportunities we were able to jump on to help employees over the years because of this retail focus, has been immense.

I also engage with the CPO as an informal coach for myself and with my external coach.  In an earlier post I mentioned that a great Chief People Officer can—and should—call a CEO out when a CEO needs to be called out.  And that also means that great Chief People Officers engage with CEOs deeply about how they are doing, they help CEOs process difficult situations, and help them see things they might not otherwise see.  Being a CEO is a lonely job sometimes, and it’s good to have a People partner to be able to collaborate with on some of the most personal and sensitive issues.

Finally, I engage with the CPO to design and execute Leadership/Management training.  This is an important skill that a great CPO brings to the company and I have found that it is the best way to create a multiplier effect of employee engagement and productivity. The CPO in your organization needs to teach all leaders and managers how to be excellent at those crafts — and how to do them in ways that are consistent with your company’s values.  This is a tall order for one person to put together so I always took a lot of time, in large blocks of hours or days, to either co-create leadership training materials and workshops with my head of People, or to lead sessions at those workshops and engage with the company’s managers and leaders in a very personal way.  That always felt to me like a very high ROI use of time.

(You can find this post on the Bolster Blog here)

I just did a podcast recording the other day for someone who asked me the biggest mistakes founders make and what to do about them. I divided my response into “early stage” and “later stage” founders. Here’s a summary of what I said about early stage founders.

1. They cling to a “good enough person” or someone who is a good performer but a weak cultural fit because they either feel beholden to that person for their output, or worse, they’re actually afraid of losing them because they’ll miss a milestone or maybe trigger some other departure.
   
   The “what to do” of course is to have courage and make the change! I wrote an essay years ago in Brad Feld and David Cohen’s book, Do More Faster, entitled Hire slowly, Fire quickly, in which I compared a poor cultural fit to a cancer that can infect the whole body of your company. A “good enough” person obviously isn’t quite that toxic, but someone like that can still prevent you from achieving your potential. In either case, the faster you realize what’s going on and make a move, the better off you are.
   
2. They get the balance wrong between “leading with vision” and “listening to customers”. Both are important for founders, but you can’t do too much of either. It’s really easy to get led to a too-narrow Product/Market Fit definition that has you building something awesome that only a dozen customers will be excited about That said, founders also have to listen if enough potential customers people say no. Your vision could just be too far ahead of the market.
   
   You have to get around this by constantly checking your enthusiasm with a mix of cold hard logic. Lots of market traction is great — but is all that traction coming from the same type of customer? Have you run your idea or wireframes by different segments, different buyers, different sizes of company (if B2B) or lots of different demographics (if B2C)? Are all of them equally enthusiastic and willing to buy? A complete lack of market traction when you’re sure your vision right is equally vexing. If literally everyone is saying “no” or worse, some polite but noncommittal version of yes, are you working to shape the vision, or at least shape how you articulate it? Sometimes your vision might be right, but your messaging might be off. Try different ones on for size.
   
3. They focus on fundraising and valuation over business fundamentals. Especially in this day and age, it’s really easy to get caught up in the “more money” hamster wheel. Raise, raise, raise. Finish one round, immediately start working on the next.
   
   In the end, business fundamentals matter — no fundamentals, no business (e.g., no next round). More than that, spend more time caring about your customers and learning and telling stories about how you made their lives better with your product or service. That’s more important to your next fundraise than just blowing through one round of money to get to the next.

Next week: the later stage founder answer (link won’t be live until 12/16/2021).

I hope this post doesn’t gross anyone out or offend anyone. I admit it’s a little weird, and that it’s more accessible to men. Hopefully everyone can get my point, even if men get it a bit more. I’m channeling Brad as I write this. So bear with me.

Here is a picture of a men’s room with floor mats under the urinals.

The difference between using a men’s room that has floor mats and using a men’s room that does not have floor mats is profound in multiple ways. I’ll leave out the specifics, but you can imagine the comparative experiences if you haven’t had one or both.

A really good floor mat, from a quick scan of Amazon and Uline just now, costs $11 if you buy in bulk and is built to last 4-6 weeks. That gives us an annual per urinal expense of about $100 – trivial in the scheme of maintaining an office, restaurant, or place of business.

But here’s the thing. These floor mats are few and far between. I don’t have scientific research on the matter, but I’d guess that between 1 in 5 and 1 in 10 places of business have them. Maybe even fewer.

So, urinal floor mats are (a) cheap, (b) easy to acquire, and (c) make a profound difference in the environment. And yet, they are only have 10-20% market penetration at most.

That market penetration is not far off from the prevalence of very good leadership and management in business. I hear stories all the time from executives about absolutely terrible leadership practices. I also hear plenty of stories that aren’t awful, but are evidence of non-leadership or non-management. The experience of working for a good manager, or in an organization with strong leadership, is profoundly different than working with the absence of those things.

To complete the analogy, good management and leadership are also (a) cheap, (b) easy to acquire, and (c) make a profound difference in the work environment. Sure, you can’t buy good leadership online, but it’s not all that difficult to be a caring, supportive, transparent manager. Heck, there’s even a book called The One Minute Manager.

So why the low market penetration of both? It makes no logical sense. It’s not as if most people haven’t had the experience of using a urinal with a floor mat…or of having a really good leader or manager. It’s not as if leaders and decision makers don’t appreciate those things themselves.

The answer boils down to three simple points that anyone who is a manager or leader can do, any day:

• You have to pay attention
• You have to care
• You have to act

Great leaders and managers exhibit all three of these traits. They pay attention to things around them, noting that Everything is Data. They care about people, about experiences, about impressions, about reputations. And when they notice that something is off – however small it is – they care enough to remember and then take the time to act. To make a small change. Send an email. Have a quick conversation. Make a suggestion. Give someone quick praise or constructive feedback.

And to come back to where this post started – it’s also not that hard to have a nice men’s room at your office or business or restaurant. You just have to pay attention to the fact that it’s a much better experience to buy floor mats. You have to care about the experience in the men’s room (for yourself, for employees, for customers, for vendors, for visitors). And then you have to act and either buy the stupid mats or ask an office manager to do the same!