Someone asked me the other day how things are going at Bolster, the new company I started along with a bunch of long-time colleagues from Return Path last year. My visceral answer was “I’m having a blast!”  I thought about it more after and came up with five reasons why. 

First, I am working with a hand-picked group of people. My co-founders, I’ve worked with for an average of 15 years – we know and trust each other tremendously. And for the most part, the same is true about our cap table. Almost everyone else at the company is also someone multiple of us have known or worked with for years. That may not last forever, but it makes things so much easier and almost friction-free out of the gate here. 

Second, this is the “second lap around the track” for a few of us on the founding team in terms of starting something from scratch, and even those at the company who haven’t done a raw startup before are super experienced professionals and many have worked in and around early stage businesses a lot. All this combines to cut down our error rate, reduce anxiety, and speed up the pace of work. More friction-free or at least low-friction work.

Third, after a 20-year run at Return Path, it’s great to start with a clean slate. No mountains of tech debt and legacy code bases. No installed base of customers with contracts or pricing we no longer like or offer. No institutional debt like a messy cap table, legacy people issues, leases for offices we don’t want or need any more.  This also points to low friction as part of what’s going on…and while that’s a theme, the next two areas are different. 

The fourth reason I’m having a blast at Bolster is that I love — and really live in — the problem space we are working in.  When we started Return Path, I was deeply familiar with email marketing and the challenges faced by our client set and had a good vision for the early product.  But as the years went on, the product got geekier and nicher — and even when it wasn’t, I was never a USER of the product since I’m not an email marketer.  In fact, at our peak of 500 people, the company employed one email marketer and therefore had one user of our own product.  At Bolster, we have three user personas — Member, Client, and Partner.  And I’m all three of them.  I’m constantly in the product, multiple times a day.  I’m deeply familiar with all angles of the executive search and board building process.  It’s MUCH better to be this close to the product, and the same is true for many of our team members.

Finally, the thing I was really worried about with starting another company from scratch — moving from a leadership role into an individual contributor role — has been nothing short of fantastic.  I love working with clients.  I love talking to members.  I love advising and coaching CEOs. I love being a pretend product manager.  I love writing marketing copy.  It’s just great to be on the front lines. (I still love working on strategy and leading the board and engaging with people internally — but those are things that never stopped being part of my day to day.)

I was trying to think if there’s some priority to this list. Almost all of these items are or can be made to be true in your second+ startup. But while four of the five can theoretically be true in your first startup as well, I don’t think it’s quite the same. So I’d have to weight “second lap around the track” a bit higher and also note that during your second lap around the track, hand-picking your team and cap table, appreciating a clean slate, and appreciating individual contributor work are that much easier and things you can appreciate a lot more as a repeat entrepreneur.

Give the Gift of a 360 to Your Board of Directors

I recently ran our biennial Board 360, and I thought it would be interesting to share the details.  Attached are a few pages from, my book, Startup CEO:  A Field Guide to Scaling Up Your Business  which describe the process as well as share the survey I developed, which I adapted from one that the legendary Bill Campbell uses at larger public companies like Intuit.

If you’ve read this blog a lot over the years, you know that we are big on 360s for staff at all levels at Return Path , and at some point a few years ago, I thought, “hmmm, shouldn’t we do this for the Board as well?”

Most of our directors had never been part of one before as Board members, and they reacted to it with varying levels of interest and trepidation.  But all of them loved the output and the discussion we had afterwards.  Extending the level of transparency we have internally to the Board was a great thing and a great use of time, and I think making the Board members review themselves and their peers critically and then seeing the results sharpened overall Board performance.

The document also shares the survey we use, which we have each director take anonymously and compile the results to share in Executive Session at a Board meeting.  We also ask a few members of the senior management team to fill out the survey as well so the Board gets feedback from them, too.

The Social Aspects of Running a Board

I’ve posted about the the topic of Boards of Directors a couple of times before, here and here.  We had one of our quarterly in-person Board meetings yesterday, which I always enjoy, and one of my directors pointed out that I never posted about the social aspects of running a Board.  Since this is a critical component of the job, it is certainly worth mentioning.

A high functioning Board isn’t materially different from any other high functioning team.  The group needs to have a clear charter or set of responsibilities, clear lines of communication, and open dialog.  And as with any team, making sure that the people on a Board know how to connect with each other as individuals as critical to building good relationships and having good communication, both inside and outside of Board meetings.

We’ve always done a dinner either before or after every in-person Board meeting to drive this behavior.  They take different forms:  sometimes they are Board only, sometimes Board and senior management; sometimes just dinner, sometimes an event as well as dinner, like bowling (the lowest common denominator of sporting activities) or a cooking class, as we did last night.  But whatever form the “social time” takes, and it doesn’t have to be expensive at all, I’ve found it to be an incredibly valuable part of team-building for the Board over the years.

You’d never go a whole year without having a team lunch or dinner or outing…treat your Board the same way!

Book Short:  Unsung Heroes

If you like “entrepreneurship by analogy” books, you’ll like The Innovators:  The Engineering Pioneers Who Made America Modern, by David Billington.  I have to admit some bias here — Professor Billington was my favorite teacher and senior thesis advisor at Princeton (I almost majored in civil engineering because of him), and this book is one of a number he’s written that are outgrowths of his most popular courses at Princeton.  And while there’s no substitute for the length or energy of his lectures, the book works.

The book is basically a person-focused engineering history of America from 1776-1883.  Billington talks about four classes of engineering product:  public structures (mostly bridges), machines that produced power, networks like the railroads and telegraphs, and processes like steel manufacturing.

His approach is to acknowledge that the Americans innovators couldn’t do much without the right context:  learnings from their counterparts in Britain, a supportive government here at home, and abundant raw materials and capital.  But with that backdrop in place, Billington tells the tale of a number of the inventions that built our modern society with a focus on the engineers who got things right.  While some of them are familiar names (Morse, Edison), many are not (Thomas Telford, J. Edgar Thomson, Joseph Henry).

Sound familiar?  It feels at many point in the book that you could insert some different names and dates and be reading a history of the Internet or information age.  And as with the Industrial Revolution, while many of the innovators in our world today are known (Bezos, Yang, Brin/Page), there are probably an equal number who are unsung heroes — either software engineers or even buisness model pioneers who haven’t sought or won’t end up in the spotlight even though their contributions to society or to their companies are giant.  I know there are a number of unsung heroes in our own engineering department at Return Path — people who aren’t market facing and who never get quoted in press releases, but who really make a difference in how the company works and how competitive we are.  This book celebrates those people as much as it does the entrepreneurs you’ve heard of.

Warning, there are lots of pages which are full of mathematical formulas, which may or may not be interesting to you, but the book still holds together 100% if you skip over them.

Book Short:  A Brand Extension That Works

Usually, brand or line extensions don’t work out well in the end.  They dilute and confuse the brand.  Companies with them tend to see their total market share shrink, while focused competitors flourish.  As the authors of the seminal work from years ago, Positioning: The Battle for Your Mind, Jack Trout and Al Reis would be the first people to tell you this.

That said, The New Positioning, which I guess you could call a line extension by Jack Trout (without Reis), was a fantastic read.  Not quite as good as the original, but well worth it.  It’s actually not a new new book – I think it’s 12 years old as opposed to the original, which is now something like 25 years old, but I just read it and think it’s incredibly relevant to today’s world.

Building on the original work, Trout focuses more this time on Repositioning and Brand Extensions — two things critical to most businesses today.  How to do the impossible, to change people’s minds about your brand or product mid-stream, whether in response to new competitive activity or general changes in the world around you.  And how to think about brand extensions (hint:  don’t do them, create a new brand like Levi’s did with Dockers).

The book also has a very valuable section on the importance of sound and words to branding and positioning, relative to imagery.  Trout has a short but very colorful metaphor about women named Gertrude here that’s reminiscent of the research Malcolm Gladwell cited in Blink.

If you haven’t read the original Positioning, that should be on your wish list for the holidays.  If you have, then maybe Santa can deliver The New Positioning!

Book Short:  Is CX the new UX?

Outside In: The Power of Putting Customers at the Center of Your Business, by Harley Manning and Kerry Bodine from Forrester Research, was a good read that kept crossing back and forth between good on the subject at hand, and good business advice in general.  The Customer Experience (CX) movement is gaining more and more steam these days, especially in B2B companies like Return Path.  The authors define Customer Experience as “how your customers perceive their interactions with your company,” and who doesn’t care about that?

A few years ago, people started talking a lot more about User Experience (UX) as a new crossover discipline between design and engineering, and our experience at Return Path has been that UX is an incredibly powerful tool in our arsenal to build great technical products via lean/agile methods.  The recurring thought I had reading this book, especially for companies like ours, was “Is CX the new UX?”

In other words, should we just be taking the same kind of lean/agile approach to CX that we do with technical product development and UX — but basically do it more holistically across every customer touchpoint, from marketing to invoice?  It’s hard to see the answer being “no” to that question, although as with all things, the devil is in the implementation details.  And that’s true at the high level (the authors talk about making sure you align CX strategy with corporate strategy and brand attributes and values) as well as a more granular level (what metrics get tracked for CX, and how do those align with the rest of the companies KPIs).

The book’s framework for CX is six high-level disciplines: strategy, customer understanding, design, measurement, governance, and culture — but you really have to read the book to get at the specifics.

Some other thoughts and quotes from the book:

• the book contains some good advice on how to handle management of cross-functional project teams in general (which is always difficult), including a good discussion of various governance models
• “to achieve the full potential of customer experience as a business strategy, you have to change the way you run your business. You must manage from the perspective of your customers, and you must do it in a systematic, repeatable, and disciplined way.”
• one suggestion the book had for weaving the customer experience into your culture (if it’s not there already) is to invite customers to speak all-hands meetings
• another suggestion the book had for weaving the customer experience into everyone’s objectives was one company’s tactic of linking compensation (in this case, 401k match) to customer experience metrics
• “Customer Experience is a journey, not a project. It has a beginning but it doesn’t have an end.”

Thanks to my colleague Jeremy Goldsmith for recommending this book.

I haven’t done short book summaries in a LONG time, but I’ll try to start adding that back into the mix as I read interesting and relevant books. Here’s one to add to your list: One Life to Lead, by Russell Benaroya. I was recently connected to Russell by a mutual friend, TA McCann at Pioneer Square Labs. TA had a sense Russell and I would hit it off, and we did. Russell is a multi-time founder/CEO, a Coach, and an author, so we have a lot in common.

One Life to Lead is an excellent book. First, it is short and easy to get through. Unlike a lot of business books, it doesn’t go on too long or contain anything extraneous. It’s to the point!

Second, the book is a business book that’s not really about business. It’s about life and what Russell calls Life Design, which is a great framing of how to be intentional about leading your life. While I have become less and less of a life planner as I’ve gotten older under the headline of “man plans, God laughs,” I am a huge believer in being intentional about everything, which I talk about in Startup CEO quite a bit in the nuts and bolts context of building your business.

Finally, Russell’s framework is easy to understand and full of concrete exercises you can to. Here are his five steps, but you’ll have to read the book to get the details:

• Ground stories with facts. This reminds me a lot of the principles we have taught team members over the years in our Action/Design (and related) trainings. First, start with absolute concrete facts that everyone will agree are facts.
• Establish your principles. This is brilliant. Your company has documented values or operating principles. Why don’t you?
• Harness energy from the environment. Figuring out what makes you tick, and what drains your energy, is so important.
• Get in and stay in your genius zone. Shouldn’t we all focus our time on the things we do best and love the most?
• Take action. How to put it together and make it all happen.

If you don’t get out in front of life, it will happen to you, and Russell’s framework is about how to make sure you are in the driver’s seat of your own life. Here’s to that.

Reboot – The Fountainhead

Happy New Year!  Every few years or so, especially after a challenging stretch at work, I’ve needed to reboot myself.  This is one of those times, and I will try to write a handful of blog posts on different aspects of that.

The first one is about a great book.  I just read Ayn Rand’s The Fountainhead for (I think) the 5^th time.  It’s far and away my favorite book and has been extremely influential on my life.  I think of it (and any of my favorite books) as an old friend that I can turn to in order to help center myself when needed as an entrepreneur and as a human.  The last time I read it was over 10 years ago, which is too long to go without seeing one of your oldest friends, isn’t it?  While the characters in the book by definition are somewhat extreme, the book’s guiding principles are great.  I’ve always enjoyed this book far more than Atlas Shrugged, Rand’s more popular novel, which I think is too heavy-handed, and her much shorter works, Anthem and We The Living, which are both good but clearly not as evolved in her thinking.

As an entrepreneur, how does The Fountainhead influence me?  Here are a few examples.

• When I think about The Fountainhead, the first phrase that pops into my head is “the courage of your convictions.”  Well, there’s no such thing as being a successful entrepreneur without having the courage of your convictions.  If entrepreneurs took “no” for an answer the first 25 times they heard it, there would be no Apple, no Facebook, no Google, but there’d also be no Ford, no GE, and no AT&T
• One great line from the book is that “the essence of man is his creative capacity.”  Our whole culture at Return Path, and one that I’m intensely proud of, is founded on trust and transparency.  We believe that if we trust employees with their time and resources, and they know everything going on in the company, that they will unleash their immense creative capacity on the problems to be solved for the business and for customers
• Another central point of influence for me from the book is that while learning from others is important, conventional wisdom only gets you far in entrepreneurship.  A poignant moment in the book is when the main character, Howard Roark, responds to a question from another character along the lines of “What do you think of me?”  The response is “I don’t think of you.”  Leading a values-driven life, and running a values-driven existence, where the objective isn’t to pander to the opinion of others but to fill my life (and hopefully the company’s life) with things that make me/us happy and successful is more important to me than simply following conventional wisdom at every turn.  Simply put, we like to do our work, our way, noting that there are many basics where reinventing the wheel is just dumb
• Related, the book talks about the struggle between first-handers and second-handers.  “First-handers use their own minds.  They do not copy or obey, although they do learn from others.”  All innovators, inventors, and discoverers of new knowledge are first-handers.  Roark’s speech at the Cortland Homes trial is a pivotal moment in the book, when he says, “Throughout the centuries, there were men who took first steps down new roads armed with nothing but their own vision.  The great creators — the thinkers, the artists, the scientists, the inventors — stood alone against the men of their time.  Every great new thought was opposed.”  In other words, first-handers, critical thinkers, are responsible for human progress.  Second-handers abdicate the responsibility of independent judgment, allowing the thinking of others to dominate their lives.  They are not thinkers, they are not focused on reality, they cannot and do not build
• The “virtue of selfishness” is probably the essence of Rand’s philosophy.  And it sounds horrible.  Who likes to be around selfish people?  The definition of selfish is key, though.  It doesn’t inherently mean that one is self-centered or lacks empathy for others.  It just means one stays true to one’s values and purpose and potentially that one’s actions start with oneself.  I’d argue that selfishness on its own has nothing to do with whether someone is a good person or a good friend.  For example, most of us like to receive gifts.  But people give gifts for many different reasons – some people like to give gifts because they like to curry favor with others, other people like to give gifts because it makes them feel good.  That’s inherently selfish.  But it’s not a bad thing at all
• Finally, I’d say another area where The Fountainhead inspires me as a CEO is in making me want to be closer to the action.  Howard Roark isn’t an ivory tower designer of an architect.  He’s an architect who wants to create structures that suit their purpose, their location, and their materials.  He only achieves that purpose by having as much primary data on all three of those things as possible.  He has skills in many of the basic construction trades that are involved in the realization of his designs – that makes him a better designer.  Similarly, the more time I spend on the front lines of our business and closer to customers, the better job I can do steering the ship

One area where I struggle a little bit to reconcile the brilliance of The Fountainhead with the practice of running a company is around collaboration.  It’s one thing to talk about artistic design being the product of one man’s creativity, and that such creativity can’t come from collaboration or compromise.  It’s another thing to talk about that in the context of work that inherently requires many people working on the same thing at the same time in a generalized way.  Someday, I hope to really understand how to apply this point not to entrepreneurship, but to the collaborative work of a larger organization.  I know firsthand and have also read that many, many entrepreneurs have cited Ayn Rand as a major influence on them over the years, so I’m happy to have other entrepreneurs comment here and let me know how they think about this particular point.

It feels a little shallow to try to apply a brilliant 700 page book to my life’s work in 1,000 words.  But if I have to pick one small point to illustrate the connection at the end, it’s this.  I realize I haven’t blogged much of late, and part of my current reboot is that I want to start back on a steady diet of blogging weekly.  Why?  I get a lot out of writing blog posts, and I do them much more for myself than for those who reads them.  That’s a small example of the virtue of selfishness at work.

Book Short:  Next, Write a Sequel

Written by Rodd Wagner and James K. Harter and billed as “the long awaited sequel to First, Break All the Rules” (one of the best management books I’ve ever read), I thought 12: The Elements of Great Managing, was good, but not great.  12…, along with the original book First… and Now, Discover Your Strengths, the latter two both by Marcus Buckingham, are all based on an extensive database of research done on corporate America by the Gallup organization over many years.  All three are valuable reads in one way or another, although I found this to be the weakest of the three.  (Note that Now… is different from the other two in that it’s not about management, it’s about self-management — very different, though based on the same research.)

Anyway, the elements of great managing, so say the authors, is all about creating employee engagement.  I totally buy into that.  And since no book short on 12… would be complete if it didn’t list out the 12…

1. Do I know what is expected of me at work?
2. Do I have the materials and equipment I need to do my work right?
3. At work, do I have the opportunity to do what I do best every day?
4. In the last seven days, have I received recognition or praise for doing good work?
5. Does my supervisor, or someone at work, seem to care about me as a person?
6. Is there someone at work who encourages my development?
7. At work, do my opinions seem to count?
8. Does the mission/purpose of my company make me feel my job is important?
9. Are my co-workers committed to doing quality work?
10. Do I have a best friend at work?
11. In the last six months, has someone at work talked to me about my progress?
12. This last year, have I had the opportunities at work to learn and grow?

The book fleshes out each of the 12, gives examples (some of which are better/clearer than others), and then addresses compensation in a very interesting chapter at the end.  Key takeaways on comp:

– Higher pay doesn’t guarantee greater engagement
– Good and bad employees are equally likely to think they deserve a raise
– Money without meaning isn’t enough
– Most employees, most of the time, feel undercompensated
– Individual pay can/should be private, but comp criteria should be very public
– People who feel well-compensated generally work harder

The book also cites a very provocative article suggesting that organizations would handle comp better if they made everyone’s comp public (in contrast to the final bullet above, yes).  I’m going to write more about compensation in future postings, so I’ll leave this section on those notes.

Finally, the book’s two closing thoughts are perhaps its most prescient:  one critical element of BEING a great manager is HAVING a great manager; and the managers who put the most into their people, get the most out of their people.

CEO Diary:  What Makes a Great Day?

5:30 a.m. – run (have to keep up with Brad)

8:45 a.m. – networking coffee with former main contact at large strategic partner; now CFO of another company in the industry

9:30 a.m. – work time/email/read newsletters, Wall St. Journal online, various RSS feeds

10:30 a.m. – internal meeting to discuss mothballing a product feature that’s hard to maintain and doesn’t generate much revenue

11:00 a.m. – internal meeting to clarify roles and responsibilities between account management and  client technical operations

11:30 a.m. – brainstorm 2006 strategy with head of one of our lines of business

1:00 p.m. – great sales call on a Tier I prospect with new sales person; business almost certainly forthcoming!

3:00 p.m. – meet with head of sales and hea of HR to discuss candidate for sales position and potential changes to sales compensation structure

3:30 p.m. – review draft of new (revolutionary!?!?) corporate web site; do deep dive on critical headlines and copy points with team members

4:30 p.m. – status meeting with new head of marketing,including quick stand-up meeting on PR strategy for upcoming trade show with one line of business head and product manager

5:30 p.m. – work/email/planning next Board meeting agenda/blog posting

7:00 p.m. – dinner with CTO

Energizing (frenetic?).  Diverse in terms of functions/departments covered.  Good balance of internal vs. external.  Some items high level, some more detailed.  Mix of brainstorming vs. decisions vs. status checks.  Some social mixed in with hardcore work.  This is why I love my job!

Book Short:  The Religion of Heresy

At the end of Tribes: We Need You to Lead Us, Seth Godin’s new book, Seth says this:

I’m going to get a lot of flak from people about what you just read. People might say that it’s too disorganized or not practical enough or that I require you to do too much work to actually accomplsh anything. That’s ok.

He’s kind of right. The book is a little breezy and meanders around, just like riffing with Seth. It’s not practical in the sense that if the entire world operated this way in the extreme, we’d have serious problems. But the fact that he requires you to do “too much work to actually accomplish anything” is part of the brilliance of his message.

This was Seth’s best book in years, mostly because it is fresh. It is not a rant about marketing; it is a wonderfully succinct look at how we as a society are rallying and organizing around causes, campaigns, companies, and collective beliefs. It’s not about the Internet, though its principles are easily implemented and amplified using online tools. It’s not a how-to guide to being a fancy corporate leader, but it’s one of the most pointed descriptions of the ethos of a certain type of leader (the upstart, or as Seth says, the heretic). It’s not about a particular revolution; it’s about how mini-revolutions are becoming the norm these days.

Tribes is short, inspirational, and pure Seth. Though quite different in its nature and mission, it really evoked for me Mark Penn’s Microtrends (post, link) — a study of larger tribes and heretics in contemporary America.

A listing of Seth’s books over the years follows:

• Permission Marketing — the original

• Unleashing the Ideavirus — good follow up on viral marketing

• Really Bad Powerpoint (ebook) — the standard for not being boring when you present

• The Big Red Fez — the standard on designing great web sites

• Survival Is Not Enough — motivating about being a nimble company

• Free Prize Inside — on being buzzworthy

• Purple Cow — on being remarkable, a great book

• The Big Moo — good follow-up with remarkable examples

• Small Is the New Big — not worth it if you read his blog

• All Marketers Are Liars — fine, a little “more of the same”

• The Dip — haven’t read it

• Meatball Sundae — haven’t read it

• Tribes — see above