Book Short:  Steve Jobs and Lessons for CEOs and Founders

First, if you work in the internet, grew up during the rise of the PC, or are an avid consumer of Apple products, read the Walter Isaacson biography of Steve Jobs (book, kindle).  It’s long but well worth it.

I know much has been written about the subject and the book, so I won’t be long or formal, but here are the things that struck me from my perspective as a founder and CEO, many taken from specific passages from the book:

• In the annals of innovation, new ideas are only part of the equation. Execution is just as important.  Man is that ever true.  I’ve come up with some ideas over the years at Return Path, but hardly a majority or even a plurality of them.  But I think of myself as innovative because I’ve led the organization to execute them.  I also think innovation has as much to do with how work gets done as it does what work gets done.

• There were some upsides to Jobs’s demanding and wounding behavior. People who were not crushed ended up being stronger. They did better work, out of both fear and an eagerness to please.  I guess that’s an upside.  But only in a dysfunctional sort of way.

• When one reporter asked him immediately afterward why the (NeXT) machine was going to be so late, Jobs replied, “It’s not late. It’s five years ahead of its time.”  Amen to that.  Sometimes product deadlines are artificial and silly.  There’s another great related quote (I forget where it’s from) that goes something like “The future is here…it’s just not evenly distributed yet.”  New releases can be about delivering the future for the first time…or about distributing it more broadly.

• People who know what they’re talking about don’t need PowerPoint.”  Amen.  See Powerpointless.

• The mark of an innovative company is not only that it comes up with new ideas first, but also that it knows how to leapfrog when it finds itself behind.  This is critical.  You can’t always be first in everything.  But ultimately, if you’re a good company, you can figure out how to recover when you’re not first.  Exhibit A:  Microsoft.

• In order to institutionalize the lessons that he and his team were learning, Jobs started an in-house center called Apple University. He hired Joel Podolny, who was dean of the Yale School of Management, to compile a series of case studies analyzing important decisions the company had made, including the switch to the Intel microprocessor and the decision to open the Apple Stores. Top executives spent time teaching the cases to new employees, so that the Apple style of decision making would be embedded in the culture.  This is one of the most emotionally intelligent things Jobs did, if you just read his actions in the book and know nothing else.  Love the style or hate it – teaching it to the company reinforces a strong and consistent culture.

• Some people say, “Give the customers what they want.” But that’s not my approach. Our job is to figure out what they’re going to want before they do. I think Henry Ford once said, “If I’d asked customers what they wanted, they would have told me, ‘A faster horse!’” People don’t know what they want until you show it to them. That’s why I never rely on market research. Our task is to read things that are not yet on the page.  There’s always a tension between listening TO customers and innovating FOR them.  Great companies have to do both, and know when to do which.

• What drove me? I think most creative people want to express appreciation for being able to take advantage of the work that’s been done by others before us. I didn’t invent the language or mathematics I use. I make little of my own food, none of my own clothes. Everything I do depends on other members of our species and the shoulders that we stand on. And a lot of us want to contribute something back to our species and to add something to the flow. It’s about trying to express something in the only way that most of us know how—because we can’t write Bob Dylan songs or Tom Stoppard plays. We try to use the talents we do have to express our deep feelings, to show our appreciation of all the contributions that came before us, and to add something to that flow. That’s what has driven me.  This is perhaps one of the best explanations I’ve ever heard of how creativity can be applied to non-creative (e.g., most business) jobs.  I love this.

My board member Scott Weiss wrote a great post about the book as well and drew his own CEO lessons from it – also worth a read here.

Appropos of that, both Scott and I found out about Steve Jobs’ death at a Return Path Board dinner.  Fred broke the news when he saw it on his phone, and we had a moment of silence.  It was about as good a group as you can expect to be with upon hearing the news that an industry pioneer and icon has left us.  Here’s to you, Steve.  You may or may not have been a management role model, but your pursuit of perfection worked out well for your customers, and most important, you certainly had as much of an impact on society as just about anyone in business (or maybe all walks of life) that I can think of.

Book Short: There is No Blueprint to $1B

Blueprint to a Billion: 7 Essentials to Achieve Exponential Growth, by David Thomson (book, Kindle) sounds more formulaic than it is. It’s not a bad book, but you have to dig a little bit for the non-obvious nuggets (yes, I get that growing your company to $1B in sales requires having a great value proposition in a high growth market!). The author looked for commonalities among the 387 American companies that have gone public since 1980 with less than $1B in revenues when they went public and had more than $1B in revenue (and were still in existence) at the time of the book’s writing in 2005.

Thompson classifies the blueprint into “7 Essentials,” which blueprint companies do well on across the board. The 7 Essentials are:

– Create and sustain a breakthrough value proposition

– Exploit a high growth market segment

– Marquee/lighthouse customers shape the revenue powerhouse

– Leverage big brother alliances for breaking into new markets

– Become the masters of exponential returns

– The management team: inside-outside leadership

– The Board: comprised of essentials experts

As I said above, there were some nuggets within this framework that made the entire read worthwhile. For example, crafting a Board that isn’t just management and investors but also includes industry experts like customers or alliance partners is critical. That matches our experience at Return Path over the years (not that we’re exactly closing in on $1B in revenues – yet) with having outside industry CEOs sit on our Board. Our Board has always been an extension of our management and strategy team, but we have specifically gotten some of our most valuable contributions and thought-provoking dialog from the non-management and non-investor directors.

Another critical item that I thought was interesting was this concept of not just marquee customers (yes, everyone wants big brand names as clients), but that they also need to be lighthouse customers. They need to help you attract other large customers to your solution – either actively by helping you evangelize your business, or at least passively by lending their name and case study to your cause.

The book is more of a retrospective analysis than a playbook, and some of its examples are a bit dated (marveling at Yahoo’s success seems a bit awkward today), and the author notes as well that many of the “blueprint” companies faltered after hitting the $1B mark. But it was a good read all-in. What I’d like to see next is a more microscopic view of the Milestones to $100 Million!

Counter Cliché:  And Founders, Too

This week, Fred’s chiche is that "the success of a company is in inverse proportion to the number of venture capitalists on the board".

I’d argue that the same statement is true of founders or management.

Boards help govern the company and watch out for shareholder interests.  Boards give outside perspectives and strategic advice to the company’s leadership.  Boards hire and fire the CEO.  And — more and more every day with large public companies — boards keep management honest.  How can these critical functions occur when a Board has too many members of the management team on it?  They can’t.  We’ve had outside directors at Return Path from Day 1.

I’m not advocating that Boards meet 100% apart from senior management.  On the contrary, our most productive Board meetings at Return Path are the ones where we have lots of management participation.  But execs present and discuss — and don’t vote — and they generally leave the last 30-60 minutes of every meeting for just the Board to discuss issues in private.  I’m also not advocating that CEOs don’t sit on boards or that the CEO never hold the Chairman role.  I think both of those items are critical to unify the watchdog function of looking out for all company stakeholders — shareholders, employees, and customers — at the highest level.

But while the success of a company may well be in inverse proportion to the number of venture capitalists on the board, that same success is jeopardized by too many execs, too.

That’s not just the title of a mediocre 1980’s sitcom starring Tony Danza, it’s a question I get periodically, including last week in an interview. A writer I know is working on an article on entrepreneurship and asked me, “Before you started your own business, how did you like working for other people?”

The question made me think a little bit. I know what she was asking — how I liked being the boss instead of working for one — but the way she phrased it is interesting and revealing about what it’s like to be a CEO. One of the biggest differences between being in a company and starting or running one is that you’re not working for a person, you’re working for many people.

As CEO of the company, I work for a Board and shareholders, I work for our customers, and I work for our employees. That’s how I approach the job, anyway.

Return Path’s Board of Directors is my boss, even though I’m one of the people on it. I report to the Board, and the Board is responsible for hiring and (hopefully not) firing the CEO, so technically, that’s my boss. The Board is also made up (for small private companies, anyway) of representatives of our biggest shareholders. As the main owners of the business, they are concerned with the growth, profitability, and overall health of the company, and they want to make sure we are building shareholder value day in, day out. That’s one very important perspective for me to have every day.

But I also work for our customers. I have to see myself as serving them — and more important, I have to steer the organization to believe that our customers are at the top of our food chain. If I do, then things will go well in the business. We will have the right products in the market at the right time to bring in new accounts. We will have a tremendous service delivery organization that wows customers and keeps them coming back for more. We will beat out our competition any day of the week. We will keep people paying our bills!

Most important, though, I work for our employees. This is very simple. An organization thrives because the people who make it up come to work inspired, focused, and productive. When they don’t, it doesn’t. I can’t wave a wand and make everyone happy all the time, but I try to focus a significant part of my time on making sure this is a great work environment; that the managers and executives are religiously focused on developing, managing, and motivating their teams; and that we’re doing a good job of communicating our mission, our values, and why each person’s job is important to the cause. This one’s the hardest of the three to get right, but it’s worth the effort.

Certainly, I don’t respond to each of my “bosses” every day as I would a direct supervisor, but in the long haul, I have to balance out the needs and interests of all three constituencies in order to have the organization be successful.

I’ve posted a lot over the years about feedback in all forms, but in particular how much I benefit from my 360 reviews and any form of “upward” feedback.  I’ve also posted about running a 360 process for/with your Board, modeled on Bill Campbell’s formula from Intuit.

I have a lot of institutional investors in our cap table at Return Path.  I was struck this week by two emails that landed in my inbox literally adjacent to each other.  One was from one of our institutional investors, sharing guidelines and timetables for doing CEO reviews across its portfolio.  The other was from one of our other institutional investors, and it invited me to participate in a feedback process to evaluate how well our investor performs for us as a Board member and strategic advisor.  It even had the Net Promoter Score question of would I recommend this investor to another entrepreneur!

The juxtaposition gave me a minute to reflect on the fact that over the 18 years of Return Path’s life, I’ve been asked to participate in feedback processes for Board members a few times, but not often.  Then I went to the thought that all of my reviews over the years have been self-initiated as well.  Just as it can be easy for a CEO to skip his or her review even when the rest of the company is going through a review cycle, it can be easy for investors to never even think about getting a review unless they get one internally at their firms.  I suspect many CEOs are reviewed by their Board, if not formally, then informally at every quarterly Board meeting.

It’s unfortunately a rare best practice for a venture capitalist or any other institutional investor to ask for CEO feedback.  I bet the ones who ask for it are probably the best ones in the first place, even though they probably still benefit from the feedback.  But regardless, it is good to set the tone for a portfolio that feedback is a gift, in all directions.

Running a Productive Offsite

A couple OnlyOnce readers asked me to do a post on how I run senior team offsites.  It’s a great part of our management meeting routine at Return Path, and one that Patrick Lencioni talks about extensively in Death by Meeting (review, book) – a book worth reading if you care about this topic.

My senior team has four offsites per year.  I love them.  They are, along with my Board meetings, my favorite times of the year at work.  Here’s my formula for these meetings:

–          WHY:  There are a few purposes to our offsites.  One for us is that our senior team is geographically distributed across 4 geographies at the executive level and 6 or 7 at the broader management team level.  So for us, these are the only times of the year that we are actually in the same place.  But even if we were all in one place, we’d still do them.  The main purpose of the offsite is to pull up from the day-to-day and tackle strategic issues or things that just require more uninterrupted time.  The secondary purpose is to continue to build and develop the team, both personal relationships and team dynamics.  It’s critically important to build and sustain deep relationships across the Executive Team.  We need this time in order to be a coordinated, cohesive, high trust, aligned leadership team for the company.  As the company has expanded (particularly to diverse geographies), our senior team development has become increasingly critical

–          WHO:  Every offsite includes what we call our Executive Committee, which is for the most part, my direct reports, though that group also includes a couple C/SVP titled people who don’t report directly to me but who run significant parts of the company (7-8 people total).  Two of the four offsites we also invite the broader leadership team, which is for the most part all of the people reporting into the Executive Committee (another 20 people).  That part is new as we’ve gotten bigger.  In the earlier days, it was just my staff, and maybe one or two other people as needed for specific topics

–          WHERE:  Offsites aren’t always offsite for us.  We vary location to make geography work for people.  And we try to contain costs across all of them.  So every year, probably 2 of them are actually in one of our offices or at an inexpensive nearby hotel.  Then the other 2 are at somewhat nicer places, usually one at a conference-oriented hotel and then one at a more fun resort kind of place.  Even when we are in one of our offices, we really treat it like an offsite – no other meetings, etc., and we make sure we are out together at dinner every night

–          WHEN:  4x/year at roughly equal intervals.  We used to do them right before Board meetings as partial prep for those meetings, but that got too crowded.  Now we basically do them between Board meetings.  The only timing that’s critical is the end of year session which is all about budgeting and planning for the following year.  Our general formula when it’s the smaller group is two days and at least one, maybe two dinners.  When it’s the larger group, it’s three days and at least two dinners.  For longer meetings, we try to do at least a few hours of fun activity built into the schedule so it’s not all work.

–          WHAT:  Our offsites are super rigorous.  We put our heads together to wrestle with (sometimes solve) tough business problems – from how we’re running the company, to what’s happening with our culture, to strategic problems with our products, services and operations.  The agenda for these offsites varies widely, but the format is usually pretty consistent.  I usually open every offsite with some remarks and overall themes – a mini-state-of-the-union.  Then we do some kind of “check-in” exercise either about what people want to get out of the offsite, or something more fun like an envisioning exercise, something on a whiteboard or with post-its, etc.  We always try to spend half a day on team and individual development.  Each of us reads out our key development plan items from our most recent individual 360, does a self-assessment, then the rest of the team piles on with other data and opinions, so we keep each other honest and keep the feedback flowing.  Then we have a team development plan check-in that’s the same, but about how the team is interacting.  We always have one or two major topics to discuss coming in, and each of those has an owner and materials or a discussion paper sent out a few days ahead of time.  Then we usually have a laundry list of smaller items ranging from dumb/tactical to brain-teasing that we work in between topics or over meals (every meal has an agenda!).  There’s also time at breaks for sub-group meetings and ad hoc conversations.  We do try to come up for air, but the together time is so valuable that we squeeze every drop out of it.  Some of our best “meetings” over the years have happened side-by-side on elliptical trainers in the hotel gym at 6 a.m.  We usually have a closing check-out, next steps recap type of exercise as well.

–          HOW:  Lots of our time together is just the team, but we usually have our long-time executive coach Marc Maltz from Triad Consulting  facilitate the development plan section of the meeting.

I’m sure I missed some key things here.  Team, feel free to comment and add.  Others with other experiences, please do the same!

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

Gambling
Tobacco
Neutriceuticals
Guns
Adult content or products

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

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

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

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

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

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

(Post 1 of 4 in the series on Scaling CROs)

In most startups, the founder is the first salesperson and while it may be difficult to let that go you’ll eventually scale, add sales reps, or maybe some form of a Sales Manager once there are more than a couple of reps.  In Startup CXO our Return Path CRO, Anita Absey, wrote about the journey of startup sales, from “selling on whiteboard” to “selling with PowerPoint” to “selling with PDF.” I encourage you to read that section if you’re wondering about hiring a CRO, but all of the hiring of sales reps and (possibly) a sales manager happens during what Anita calls the “White Board” stage as you’re beginning to transition to “Selling with PowerPoint.” 

Selling from a White Board means that you are essentially working with an interested potential customer on a custom and conceptual sale; selling from PowerPoint means that you are selling tailored solutions—you’re no longer at the discovery stage. Selling from either the White Board or Powerpoint stage is fine for an early-stage company, but eventually you’ll want to scale and hire your first CRO. Here are some of the telltale signs that will help you figure out if you should bring in a CRO.

First, you’ll know it’s time to hire a CRO when you’re nervous about HOW you’re going to make this quarter’s number — not just that WHETHER or not you’ll make it (since you should know that as much as anyone). Another sign that it’s time to hire a CRO is when you aren’t clear what the levers are, or what the pipeline/forecast details are, to hit those quarterly numbers. 

If you are spending too much of your own time managing individual deals and pricing, or teaching individual reps how to get jobs done, that’s a clear indicator that a CRO is needed. If your board asks you if you’re ready to step on the gas and scale your revenue engine (e.g., move from Powerpoint to PDF), and you don’t have a great answer and aren’t sure how to get to one then you need to hire a CRO.

A fractional CRO can add a lot of value, especially at a small volume where a full-time CRO would be overkill. Or, if your sale is very complex or to a very senior buyer, and a more junior sales team needs a fair amount of deal support from above, a fractional CRO makes a lot of sense. Sometimes a fractional CRO can help you enter a new adjacent segment (e.g., mid-market going to enterprise), and then you’ll need a seasoned professional to help translate sales processes from one segment to the other while keeping the initial segment running smoothly. 

If you’re not sure what kind of sales leader you’ll need long-term and full time because you’re not at enough scale yet, a fractional CRO can help you “try before you buy.” You can try out a specific type of revenue leader to see if that type works, for example, sales only, sales + customer success, manager of hunters, or builder of a high velocity sales engine, to name a few different options.

Hiring a CRO will definitely free up time for founders and allow them to work on other things that drive the business, without worrying about sales.

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

(Post 1 of 4 in the series of Scaling CCOs)

Very few startups start life with a Chief Customer Officer, even though customers are the lifeblood of every startup; instead, you’ll likely start your customer service organization with a “jack of all trades” account manager position. You’ll have one person who handles all customer issues from basic support all the way through to true customer success. Sometimes these functions will be handled by the product team but most often they are handled by a customer service team.  Specialized roles and multiple teams (e.g, support vs. professional services) with their own managers can emerge quickly in the life of a startup and these roles will usually come before a full-time CCO, unless one of the company’s founders happens to be playing that role.

But you won’t be able to scale effectively (or quickly) with a hodge-podge of customer support roles and there are some telltale signs that will let you know you need to bring in a CCO. For example, you’ll know it’s time to hire a CCO when you realize you’ve never measured customer satisfaction. You don’t have any metrics at all — no Net Promoter Score, no basic customer satisfaction measures, no product engagement levels…nothing. You’re just hoping for the best, and hope is not a strategy. Another sign that you need to hire a CCO is if you are spending too much of your own time putting out customer fires rather than thinking about how to make customers more successful by using your product.

A second telltale sign will come from your board, if you have one. If your board asks you which of your customer segments has the highest margin, or has the most opportunity, and you don’t have a great answer and aren’t sure how to get to one then it’s time to consider hiring your first CCO. Of course, you don’t have to wait for a board member to ask that question and if you want to be proactive you can create a list of questions that a board member might ask and see whether or not you can answer them. If you can’t, or if it takes a ton of time to track down the answers, you’re probably ready for a CCO.

The search for a CCO can be long and time-consuming and in a future post I’ll talk about what “great” looks like for a CCO, but if you’re at the point where you need a CCO but don’t have the money or time to bring in an executive, a fractional CCO is a great option. A fractional CCO can work well if you have a relatively contained or small customer success/account management organization, but it is already very diverse in its sub-functions (support, account management, success, professional services) and none of the team leaders of those teams have the range of experience to orchestrate the handoffs and synergies across the sub-functions. A CCO touches nearly every part of the organization, from sales, to product, to marketing and this person needs to be a collaborator, a champion for customers, and a strategic thinker that understands consumer trends and demographics. A fractional executive CCO can bring a lot of skills to a startup and help to grow both the customer organization and the individuals in it, including mentoring those in the Customer organization who can become eventual leaders, or helping to reorganize the Customer organization for greater efficiency, or even help interview, vet, and find their replacement.

If you’re a startup and you have potential to scale but seem to be spending a lot of time and energy working on customer issues—without being able to actually move forward—a Chief Customer Officer should be a role you’d want to fill as soon as possible. Almost nothing takes down more companies than poor customer support. 

You can find this post on the Bolster Blog here

I realize I haven’t posted much lately.  As you may know, the title of this blog, OnlyOnce, comes from a blog post written by my friend and board member Fred Wilson from Union Square Ventures entitled You Are Only a First-Time CEO Once, which he wrote back in 2003 or 2004.  That inspired me to create a blog for entrepreneurs and leaders.  I’ve written close to 1,000 posts over the years, and the book became the impetus for a book that another friend and board member Brad Feld from Foundry Group encouraged me to write and helped me get published called Startup CEO:  A Field Guide to Scaling Up Your Business back in 2013.

Today is a special day in my entrepreneurial journey and in the life of the company that I started back in 1999 (last century!), Return Path, as we announce that Return Path has entered into a definitive agreement to be acquired by an exciting new company called Validity.  Press release is here.

Over almost 20 years, we’ve built Return Path into one of the largest and (I think) most respected companies in the email industry.  We’ve had a culture of innovation that has led to some groundbreaking products for our customers and partners to help make email marketing work better for consumers as well as marketers, and to help keep inboxes safe and clean for mailbox providers and security companies.  

But the company is unusual in many respects.  One of those is longevity. I’m not sure how many Internet companies started in 1999 are still private, backed and led by the same team the whole time, and generally in the same business they started in.  Another is our values-driven “People First” culture. From Day 1, we have believed that if we attract and retain and develop and invest in the best people, we will make our customers successful with great products and service, and that if we do right by our customers, we will do right long term by our shareholders.  While I know that not every employee who ever walked through our doors had a great experience, I know most did and hope that all of them realize we tried our best. Finally, I’m proud that our company gave birth to a non-profit affiliate Path Forward a few years back at the hands of executives Andy Sautins, Cathy Hawley, and Tami Forman.  Path Forward helps parents get back to work after a career break and helps companies improve their gender diversity and hiring biases and has already been a game changer for dozens of companies and hundreds of women.

Today, Return Path serves almost 4,000 customers in almost every country on the globe, with $100 million in revenue, profitable, and excited about the next leg of our brands’ and our products’ lives in the care of Validity.  If you haven’t heard of Validity before today, watch out – you will hear a LOT about them in the weeks and months ahead. They are an incredibly exciting new company with a vision to help tens of thousands of companies across the globe improve their data quality but also help them use data to improve business results.  That vision, inspired by a new friend, CEO Mark Briggs, is a wonderful fit for Return Path’s products and services and people.

To finish this post where I started, Fred’s exact words in that post which got this blog going were:

What does this mean for entrepreneurs and managers? It means that the first time you run a business, you should admit what you are up against. Don’t let ego get in the way. Ask for help from your board and get coaching and mentoring. And recognize that you may fail at some level. And don’t let the fear of failure get in the way. Because failure isn’t fatal. It may well be a required rite of passage.

All of that is true and has been great advice for me over the years.  But Fred left out one important piece, which is that entrepreneurs need to constantly thank the people around them who either work their butts off as colleagues in the business or who give them helpful advice and coaching.  Return Path’s journey has been a long one, longer than most, and the full list of people to thank is too long for a blog post.

I’ve noted Fred and Brad in this post already and I want to thank them and also thank Greg Sands from Costanoa Ventures, the third member of our “dream team” investor syndicate, for their friendship and unwavering support and good counsel for me and Return Path for almost two decades, as well as many other board members we’ve had over the years including long-time independent directors Jeff Epstein, Scott Petry, and Scott Weiss.

I want to thank my co-founders Jack Sinclair and George Bilbrey, and anyone who has ever been on my executive team, including long-time execs Ken Takahashi, Shawn Nussbaum, Cathy Hawley, Dave Wilby, Anita Absey, Angela Baldonero, Andy Sautins, Louis Bucciarelli, Mark Frein, and David Sieh.  There’s nothing quite like being in the proverbial foxhole with someone during a battle or two or ten to forge a tight bond. I want to thank Andrea Ponchione, my extraordinary assistant for 14 years, who keeps me running, sane, and smiling every day. I want to thank my executive coach Marc Maltz and the members of my CEO Forum for allowing me to be unplugged and for their friendship and advice.  I want to thank all of Return Path’s 430 employees today and over 1,300 ever for their hard work in building our company and culture together and for our 4,000 customers and partners for putting their faith in us to help them solve some of their biggest challenges with email.

Finally, no thank you list for this journey would be complete without saying a special thank you to my wonderful wife Mariquita and kids Casey, Wilson, and Elyse.  They deserve some kind of special honor for being inspirational cabin-mates on the entrepreneurial roller coaster without ever being asked if they were up for it.

This event may inspire me to begin writing more regularly again on OnlyOnce.  Stay tuned!

Startup CEO (OnlyOnce- the book!), Part II – Crowdsourcing the Outline

As I mentioned a few weeks ago here, I’m excited to be writing a book called Startup CEO:  A Field Guide to Building and Running Your Company, to be published by Wiley & Sons next summer.  Since many readers of OnlyOnce are my target audience for the book, I thought I’d post my current outline and ask for input and feedback on it.  So here it is, still a bit of a work in progress.  Please comment away and let me know what you think, what’s missing, what’s not interesting!

1           Part One: Vision and Strategy (Defining the Company)
1.1          Setting the Company’s Agenda
1.2          NIHITO! (or, “Nothing Interesting Happens in the Office”)
1.3          Setting the Business Direction
1.4          Strategic Planning, Part I: Turning Concepts Into Strategy
1.5          Strategic Planning, Part II: Creating the Plan
1.6          Defining Mission, Vision and Values
1.7          Communicating Vision and Strategy
1.8          The Role of M&A
1.9          The Art of the Pivot
1.10       How Vision and Strategy Change over Time

2           Part Two: Talent (Building the Company’s Human Capital)
2.1          Building a Team
2.2          Scaling the Team
2.3          Culture
2.4          Interviewing
2.5          Recruiting
2.6          Onboarding
2.7          Setting Goals
2.8          Feedback
2.9          Development
2.10       Compensation
2.11       Promoting
2.12       Rewarding
2.13       Managing Remote Offices and Employees
2.14       Firing: When It’s Not Working
2.15       How Talent Changes over Time

3           Part Three: Execution (Aligning Resources with Strategy)
3.1          Making Sure There’s Enough Money in the Bank
3.2          Types of Financing
3.3          Fundraising Basics
3.4          Negotiating Deals
3.5          Pros and Cons of Outside Financing
3.6          Forecasting and Budgeting
3.7          Creating a Company Operating System
3.8          Meeting Routines
3.9          Driving Alignment
3.10       A Metrics-Driven Approach to Running a Business
3.11       Learning
3.12       Post-Mortems
3.13       Thinking About Exits
3.14       How Execution Changes over Time
3.14.1      Finance
3.14.2      Execution

4           Part Four: Management And Leadership (The How of Being a CEO)
4.1          Leading an Executive Team
4.2          Critical Personal Traits
4.3          Being Collaborative
4.4          Being Decisive: Balancing Authority and Consensus
4.5          The Value of Symbolism
4.6          Getting the Most out of People
4.7          Diving Deep without Being Disruptive
4.8          Articulating Purpose
4.9          Collecting Data from the Organization
4.10       Managing in an Economic Downturn
4.11       Managing in Good Times vs. Bad Times
4.12       Communication
4.12.1      Macro (to Your Company and Customers)
4.12.2      Micro (One-on-One)
4.13       How Management and Leadership Change over Time

5           Part Five: Boards (A Unique Aspect of the CEO’s Job)
5.1          Building Your Board
5.2          Meeting Materials
5.3          Meetings
5.4          Between Meetings
5.5          Making Decisions and Maximizing Effectiveness
5.6          The Social Aspects of Running a Board
5.7          Working with the Board on Compensation
5.8          Evaluating the Board
5.9          Serving on Other Boards
5.10       How Boards Change over Time

6           Part Six: Managing Yourself So You Can Manage Others
6.1          Creating a Personal Operating System
6.2          Working with an Executive Assistant
6.3          Working with a Coach
6.4          Finding Your Voice
6.5          The Importance of Peer Groups
6.6          Your Family
6.7          Taking Stock
6.8          Staying Fresh
6.9          Staying Healthy
6.10       Traveling