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

Book Short: Wellness Redefined

Well Being: The 5 Essential Elements, by Tom Rath and Jim Harter from the Gallup organization, is a solid read and incredibly short. It’s one of those books that’s really a long article stretched and bound. But it goes beyond the basics of what I expected, which was something like “having healthy employees cuts down on absenteeism” and has a couple great elements of food for thought for leaders looking to build cutting edge and uber-productive organizations. It comes out of the same general body of research as four other very strong books I’ve written about over time — First, Break all the Rules, Now, Discover Your Strengths, 12: The Great Elements of Managing (book, review), and Go Put Your Strengths to Work (book, review).

The authors define well being as having five separate components:  career well being, social well being, physical well being, financial well being, and community well being. Ok, that makes sense, but the three most interesting points the book made from my perspective were:

1. Well being isn’t just about one of these five elements – it’s about all five, and how they interact together, and how the workplace can support all of them
2. Achieving long-term objectives around well being requires finding short-term incentives that drive the same behavior in more obvious and immediate ways, as most long-term well being drivers require short term sacrifice. So figure out how to make eating a salad better for you not just years from now but TODAY (you’ll have more energy after lunch than if you eat that cheeseburger), for example
3. Financial well being isn’t something a lot of companies focus on, and maybe it should be. Particularly in our industry we hire knowledge workers and assume therefore that they’re smart and educated about everything…but maybe there are ways that the company can support financial well being that aren’t necessarily obvious

The book is full of stats from the underlying research, most of which show that most people are shockingly unhappy, and that most workplaces dont do enough to support employee wellness. The book also notes, as is the case with most things, that promoting well being among employees requires more than just setting up programs. Doing it right requires constant vigilance, measurement, and follow up. At Return Path, we do a bunch of programs along the lines suggested by the book (but can and should do more!), but we’ve never been rigorous with follow up. Good food for thought.

Note there is also a free whitepaper on the economics of well being that you can download here.  The white paper is ok…but not nearly as interesting as the book, and note that it does not substitute for the book.  Thanks to my colleague Cathy Hawley for this book!

Startup CEO (OnlyOnce – the book!), Part III – Pre-Order Now

My book, Startup CEO:  A Field Guide to Scaling Up Your Business, is now available for pre-order on Amazon in multiple formats (Print, Kindle), which is an exciting milestone in this project!  The book is due out right after Labor Day, but Brad Feld tells me that the more pre-orders I have, the better.  Please pardon the self-promotion, but click away if you’re interested!

Here are a few quick thoughts about the book, though I’ll post more about it and the process at some point:

• I’ll be using the hashtag #startupceo more now to encourage discussion of topics related to startup CEOs – please join me!
• The book has been described by a few CEOs who read it and commented early for me along the lines of “The Lean Startup movement is great, but this book starts where most of those books end and takes you through the ‘so you have a product that works in-market – now what?’ questions”
• The book is part of the Startup Revolution series that Brad has been working on for a couple years now, including Do More (Even) Faster, Venture Deals, Startup Communities, and Startup Life (with two more to come, Startup Boards and Startup Metrics)
• Writing a book is a LOT harder than I expected!

At this point, the best thing I can do to encourage you to read/buy is to share the full and final table of contents with you, sections/chapters/headings.  When I get closer in, I may publish some excerpts of new content here on Only Once.  Here’s the outline:

Part I: Storytelling

• Chapter 1: Dream the Possible Dream…Entrepreneurship and Creativity, “A Faster Horse,” Vetting Ideas
• Chapter 2: Defining and Testing the Story…Start Out By Admitting You’re Wrong, A Lean Business Plan Template, Problem, Solution, Key Metrics, Unique Value Proposition and Unfair Advantages, Channels, Customer Segments, Cost Structure and Revenue Streams
• Chapter 3: Telling the Story to Your Investors…The Business Plan is Dead. Long Live the Business Plan, The Investor Presentation, The Elevator Pitch, The Size of the Opportunity, Your Competitive Advantage, Current Status and Roadmap from Today, The Strength of Your Team, Summary Financials, Investor Presentations for Larger Startups
• Chapter 4: Telling the Story to Your Team…Defining Your Mission, Vision and Values, The Top-down Approach, The Bottom-Up Approach, The Hybrid Approach, Design a Lofty Mission Statement
• Chapter 5: Revising the Story…Workshopping, Knowing When It’s Time to Make a Change, Corporate Pivots: Telling the Story Differently, Consolidating, Diversifying, Focusing, Business Pivots: Telling a Different Story
• Chapter 6: Bringing the Story to Life…Building Your Company Purposefully, The Critical Elements of Company-Building, Articulating Purpose:  The Moral of the Story, You Can Be a Force for Helping Others—Even If Indirectly

Part II: Building the Company’s Human Capital

• Chapter 7: Fielding a Great Team…From Protozoa to Pancreas, The Best and the Brightest, What About HR?, What About Sales & Marketing?, Scaling Your Team Over Time
• Chapter 8: The CEO as Functional Supervisor…Rules for General Managers
• Chapter 9: Crafting Your Company’s Culture…, Introducing Fig Wasp #879, Six Legs and a Pair of Wings, Let People Be People, Build an Environment of Trust
• Chapter 10: The Hiring Challenge…Unique Challenges for Startups, Recruiting Outstanding Talent, Staying “In-Market”, Recruitment Tools, The Interview: Filtering Potential Candidates, Two Ears One Mouth, Who Should You Interview?, Onboarding: The First 90 Days
• Chapter 11: Every Day in Every Way, We Get a Little Better…The Feedback Matrix, 1:1 Check-ins, “Hallway” Feedback, Performance Reviews, The 360, Soliciting Feedback on Your Own Performance, Crafting and Meeting Development Plans      
• Chapter 12: Compensation…General Guidelines for Determining Compensation, The Three Elements of Startup Compensation, Base Pay, Incentive Pay, Equity              
• Chapter 13: Promoting                …Recruiting from Within, Applying the “Peter Principle” to Management, Scaling Horizontally, Promoting Responsibilities Rather than Swapping Titles               
• Chapter 14: Rewarding: “It’s the Little Things” That Matter…It Never Goes Without Saying, Building a Culture of Appreciation
• Chapter 15: Managing Remote Offices and Employees…Brick and Mortar Values in a Virtual World, Best Practices for Managing Remote Employees
• Chapter 16: Firing: When It’s Not Working…No One Should Ever Be Surprised to Be Fired, Termination and the Limits of Transparency, Layoffs

Part III: Execution

• Chapter 17: Creating a Company Operating System…Creating Company Rhythms, A Marathon? Or a Sprint?
• Chapter 18: Creating Your Operating Plan and Setting Goals…Turning Strategic Plans into Operating Plans, Financial Planning, Bringing Your Team into Alignment with Your Plans, Guidelines for Setting Goals
• Chapter 19: Making Sure There’s Enough Money in the Bank…Scaling Your Financial Instincts, Boiling the Frog, To Grow or to Profit? That Is the Question, First Perfect the Model, Choosing Growth, Choosing Profits, The Third Way
• Chapter 20: The Good, the Bad, and the Ugly of Financing…Equity Investors, Venture Capitalists, Angel Investors, Strategic Investors, Debt, Convertible Debt, Venture Debt, Bank Loans, Personal Debt, Bootstrapping, Customer Financing, Your Own Cash Flow
• Chapter 21: When and How to Raise Money…When to Start Looking for VC Money, The Top 11 Takeaways for Financing Negotiations
• Chapter 22: Forecasting and Budgeting…Rigorous Financial Modeling, Of Course You’re Wrong—But Wrong How?, Budgeting in a Context of Uncertainty, Forecast, Early and Often
• Chapter 23: Collecting Data…External Data, Learning from Customers, Learning from (Un)Employees, Internal Data, Skip-Level Meetings, Subbing, Productive Eavesdropping
• Chapter 24: Managing in Tough Times…Managing in an Economic Downturn, Hope Is Not a Strategy—But It’s Not a Bad Tactic, Look for Nickels and Dimes under the Sofa, Never Waste a Good Crisis, Managing in a Difficult Business Situation
• Chapter 25: Meeting Routines…Lencioni’s Meeting Framework, Skip-Level Meetings, Running a Productive Offsite
• Chapter 26: Driving Alignment…Five Keys to Startup Alignment, Aligning Individual Incentives with Global Goals
• Chapter 27: Have You Learned Your Lesson?…The Value (and Limitations) of Benchmarking, The Art of the Post-Mortem
• Chapter 28: Going Global…Should Your Business Go Global?, How to Establish a Global Presence, Overcoming the Challenges of Going Global, Best Practices for Managing International Offices and Employees
• Chapter 29: The Role of M&A…Using Acquisitions as a Tool in Your Strategic Arsenal, The Mechanics of Financing and Closing Acquisitions, Stock, Cash, Earn Out, The Flipside of M&A: Divestiture, Odds and Ends, Integration (and Separation)
• Chapter 30: Competition…Playing Hardball, Playing Offense vs. Playing Defense, Good and Bad Competitors
• Chapter 31: Failure…Failure and the Startup Model, Failure Is Not an Orphan

Part IV: Building and Leading a Board of Directors

• Chapter 32: The Value of a Good Board…Why Have a Board?, Everybody Needs a Boss, The Board as Forcing Function, Pattern Matching, Forests, Trees, Honest Discussion and Debate
• Chapter 33: Building Your Board…What Makes a Great Board Member?, Recruiting a Board Member, Compensating Your Board, Boards as Teams, Structuring Your Board, Board Size, Board Committees, Chairing the Board, Running a Board Feedback Process, Building an Advisory Board
• Chapter 34: Board Meeting Materials…“The Board Book”, Sample Return Path Board Book, The Value of Preparing for Board Meetings
• Chapter 35: Running Effective Board Meetings…Scheduling Board Meetings, Building a Forward-Looking Agenda, In-Meeting Materials, Protocol, Attendance and Seating, Device-Free Meetings, Executive and Closed Sessions
• Chapter 36: Non-Board Meeting Time…Ad Hoc Meetings, Pre-Meetings, Social Outings
• Chapter 37: Decision-Making and the Board…The Buck Stops—Where?, Making Difficult Decisions in Concert, Managing Conflict with Your Board
• Chapter 38: Working with the Board on Your Compensation and Review…The CEO’s Performance Review, Your Compensation, Incentive Pay, Equity, Expenses
• Chapter 39: Serving on Other Boards…The Basics of Serving on Other Boards, Substance, or Style?

Part V: Managing Yourself So You Can Manage Others

• Chapter 40: Creating a Personal Operating System…Managing Your Agenda, Managing Your Calendar, Managing Your Time, Feedback Loops
• Chapter 41: Working with an Executive Assistant…Finding an Executive Assistant, What an Executive Assistant Does
• Chapter 42: Working with a Coach…The Value of Executive Coaches, Areas Where an Executive Coach Can Help
• Chapter 43: The Importance of Peer Groups…The Gang of Six, Problem-Solving in Tandem
• Chapter 44: Staying Fresh…Managing the Highs and Lows, Staying Mentally Fresh, At Your Company, Out and About, Staying Healthy, Me Time
• Chapter 45: Your Family…Making Room for Home Life, Involving Family in Work, Bringing Work Principles Home
• Chapter 46: Traveling…Sealing the Deal with a Handshake, Making the Most of Travel Time, Staying Disciplined on the Road
• Chapter 47: Taking Stock of the Year…Celebrating “Yes”; Addressing “No”, Are You Having Fun?, Are You Learning and Growing as a Professional?, Is It Financially Rewarding?, Are You Making an Impact?
• Chapter 48:  A Note on Exits…Five Rules of Thumb for Successfully Selling Your Company

 If you’re still with me and interested, again here are the links to pre-order (Print, Kindle).

Was anyone else as appalled as I am by the contents of Connie Loizos’s recent article, Coming out of COVID, investors lose their taste for board meetings? The stories and quotes in the article about VCs reducing their interest and participation in Board meetings, not showing up, sending the junior associate to cover, etc. are eye opening and alarming if widespread. 

The reasons cited in the article are logical—overextended VCs, Zoom fatigue, and newbie directors. Connie’s note that “privately, VCs admit they don’t add a lot of value to boards” is pretty funny to read as a CEO who has heard a ton of VCs talk about how much value they add to boards (although the good ones DO add a lot of value!).  

For the most part, everything about the substance of this article just made me angry.  

Disengaged or dysfunctional boards aren’t just bad for CEOs and LPs; they’re bad for everyone. If the world has truly become a place where the board meeting is nothing more than a distraction for CEOs, and investors think it’s a tax they can’t afford, then it’s time to hit the reset button on boards and board meetings. 

Here are four things that need to happen in this reset:

VCs need to do their job well or stop doing it. The argument that investors did too many deals in the pandemic so now they don’t have any time is a particularly silly one, since the pandemic reduced the amount of time VCs needed to spend on individual board meetings as well. I used to have four board meetings each year with directors who were traveling for the meetings, having dinners, spending time with the team and sitting in on committee meetings. 

Today, boards are lucky to have one in-person meeting a year (more on that later). And as everything else takes less time, and there’s little transit, any given VC should have doubled the time they spend on board meetings.

Serving on a board post-investment is a central part of the VC role. They have obligations to the founders they back and to the LPs they represent. The entire role is “find deals, execute deals, manage the portfolio.” 

If they no longer have time for the third job, they need to admit that to both founders and LPs before stepping down. If a VC can’t be bothered to focus on minding their investments and adding value, they should work with the company to find their replacement.  

CEOs need to take their job as leader of the board seriously. Would a good CEO just throw their hands up if they found management team meetings boring or a waste of time? No. They’d fix the structure of the team or meetings. If not, they shouldn’t be the CEO. 

It’s no different with boards. Whether or not the CEO is the board chair, they’re the leader of the organization. So, one of the few “must do” items in their job description is leading the board. The board is part of the CEO’s team, just like the management team. 

CEOs get to call the meetings, run the meetings, and insist on attendance. The CEO’s obligation is to make it easy and meaningful for everyone so the board isn’t a tax but rather a secret weapon for the company’s success. As my long-time independent director Scott Weiss used to tell me, boards consume whatever you put in front of them. Garbage in, garbage out. That means paying careful attention to the board materials, to meeting etiquette, and everything in between.

If the CEO doesn’t know how to do that, they should find a CEO mentor who can teach them, observe some well run boards in action through their network, or read Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, a book I just published along with co-authors and VCs Brad Feld and Mahendra Ramsinghani.

Here’s one tip on making Board prep more efficient: work your Operating System and your Board Book formats so you do one set of reporting for the company and management team that is 95% reusable without any changes for your board.

The format for Board meetings needs to evolve. Board meetings need to evolve in our world of hybrid work just as office work needs to evolve. The format that works for in-person can’t just “lift and shift” to Zoom as is, indefinitely.

Here’s how I’m steering my board:

• I insist on one or two “old school” meetings per year, meaning in-person attendance required, half a day long, and including a meal and even an activity. If I’m only going to see my directors together infrequently, I make it mandatory, but I also make it worthwhile and fun.
  
• Remote meetings that happen between the in-person meetings are becoming shorter and tighter. I still send out a lot reading material beforehand, but I make sure to keep the focus on a fixed number of major topics to keep the discussion engaging.
  
• We need a new set of expectations around Zoom meeting etiquette for long meetings. It’s okay to ask people to close their email, browser, and Slack before the meeting starts. If a meeting is more than two hours long, a 15 minute break in the middle is important. Use breakout rooms to mix up topic discussions and working sessions.
  
• I am trying a new meeting format to maximize director conversation and team development. I start every meeting with a director-only session for half an hour that’s not exactly an Executive Session but is more fun and social—usually including a nonwork discussion topic, as if we were sitting around the dinner table having a cocktail. That gets the conversational juices flowing. Then when my team and observers join the meeting, I ask those people to turn their video off, and I ask directors to adjust their Zoom setting to “hide participants not on video” to keep the number of Zoom squares down to the bare minimum. Any time a team member or observer wants to engage in a particular topic, they turn their video on. Then we follow the meeting with Executive Session and Closed Session and a single-director debrief with me. That is a lot of moving pieces to manage, I find that but doing so keeps the meeting fresh and well paced.
  
• Finally, I’m following Fred Wilson’s advice and running a very short survey post-meeting to ask directors basic questions so they can summarize their thinking for me and the team: What are we doing well? What do we need more work on? And did the meeting meet your expectations?

Companies need to Follow the Rule of 1s

The secret to engaged and diverse boards is to mix up their membership more than most companies do. Our Board Benchmark study at Bolster indicates that the vast majority of private company boards have no independent directors at all—only founders and investors—and every year, the vast majority of the “open independent seats” specified in those companies’ charters go unfilled. 

It’s hard work hiring a new independent board member, and it rarely rises to the top of the CEO’s priority list. But the more independent the board is, and the more diverse the board is in every way (in terms of demographics as well as experience and background), the more robust the conversations around the table become, and the more valuable the board is to the CEO.

My Rule of 1s for building highly effective boards is simple:

• Add independent directors to your board on Day 1
• Try to limit your Board to 1 founder/team member
• Then, for every 1 investor on your board,
• Add 1 independent director

A great board is one of a company’s greatest assets. A weak board can kill a company. A mediocre board is just a waste of time. There’s no question that running an effective board, or serving as an effective director, takes serious time and energy and diligence. But that’s not a reason not to try.

(This post first ran on TechCrunch+ and is also running on the Bolster blog)

The Boomerang Club, or How to Quit Your Job, Part II

My post last week on How to Quit Your Job has generated about two dozen comments as well as a really lengthy thread on Y Combinator’s Hacker News.  My various replies to comments are worth summarizing here – this is a reprint of my comment on Hacker News:

First, my post was not intended to be general advice to employees of all companies on how to handle a situation where they’re starting to look for jobs.  Of course, many environments would not respond well to that approach.  My point was just that that’s how we encourage employees to handle the situation at Return Path, and we have created a safe environment to do so.  By the way, it doesn’t happen here 100% of the time either, by any stretch of the imagination.  But I wish it did.  When it happens, it’s better for everyone — the company as well as the employee, who either (a) ends up staying because we resolve some issue we weren’t aware of, or (b) has a less stressful and more graceful transition out.

Second, the way we run our business is around a bit of a social contract — that is to say, a two-way street.  And just as we ask employees to start a dialog with us when they are thinking of leaving, we absolutely, 100% of the time, are open and transparent with employees when they are in danger of being fired (other than the occasional urgent “for cause” situation).  We give people ample opportunity to correct performance and even fit issues.  In terms of someone’s question below about lay-offs, we fortunately haven’t had to do those since 2001, but if I recall, even then, we were extremely transparent about our financial position and that we might need to cut jobs in 30 days.

But I wanted to take this post to emphasize a related, second point.  If it’s a given that you are going to quit your job, then HOW you quit your job becomes super important.  And this is general advice, not something specific to Return Path.  Even if you’re unhappy – even if you feel totally wronged or burned in some way – there is never a good reason to burn bridges on the way out the door.  In fact, the opposite is what I would consider best practice:  make the transition as easy as possible for your company.

Document your job really well, including specifics of all open projects.  Work with your manager and teammates to hand off all responsibilities.  Be frank and constructive in your exit interview.  Make the extra effort to leave things in good working order.

We have a long history of hiring back former employees here.  We proudly call it The Boomerang Club, and there have been a dozen or so members over the years.  We try to make it easy to come back if you leave.  First, we celebrate the return of a former employee pretty widely, and we obviously modify our usual extensive interview process.  If you come back in less than a year, we pretend that you never left in terms of giving you credit for continuous service.  If your gap is more than a year, we don’t give you credit for the time you were gone, but we do give you full credit for the time you’d been here before you left.

But you can’t really be a member of The Boomerang Club if you leave your job in the wrong way.  HOW you do that says a lot about you, and everyone at your company will take note and remember it.

Last week, I wrote about the concept of the Operating Philosophy, and how it fits with a company’s Operating Framework and Operating System and defines the essence of who you are as a company…what form of company you are.

While we had a loose Operating Philosophy at Return Path, we never really crisply articulated it, and that caused some hand-wringing at various points over the years, as different people interpreted our “People First” mantra in different ways. So this time around at Bolster, we’re trying to be more intentional about this up front. We have labeled our company a “Mostly Self Managed Organization” or MSMO (pronounced Miz-Moh). We made those up.

Our Operating Philosophy – we are a Mostly Self-Managed Organization, or MSMO (pronounced Miz-Mo, a term we just made up). The MSMO is the product of years of work, research, practical learning, and thinking on our part.  Self-Management has been important to me my whole career as a manager and leader.  Over the last 15 years, the team and I have studied various forms of self-management with interviews and onsite meetings at Netflix, Gore, Nucor, Morningstar, and Zappos.  While we implemented some aspects of it at Return Path, we are trying to take the implementation a step further here at Bolster from the beginning.

Of all those companies, what we’re doing is probably closest to the Operating Philosophy of W.L. Gore & Associates, which you can find written out online without a name but with the description that “individuals don’t need close supervision; what they need is mentoring and support.” The embodiments of the Operating Philosophy at Gore may be different from those we create at Bolster, but the essence of the philosophies is pretty similar.

Why a MSMO?  We employ smart people, and smart people crave autonomy, purpose, and mastery (according to Daniel Pink) and do their best work when they have those things in alignment.  

So, how do we define self-management at Bolster?  We aren’t going to be a DAO.  I don’t think that model works for a for-profit multifaceted corporation – complete Self-Management is too chaotic.  Leadership and mentorship matter and make a difference in guiding strategy, critical decisions, and careers. Holocracies or other unnamed structures like that of Morningstar are ok, but they are so rigidly ideological that they require an immense amount of work-around, or scaffolding, to be practical.

But we aren’t a traditional fixed top-down hierarchy, either.  We are going to run the business in a way that lets people co-create their work and be responsible for driving their own feedback and development with a support structure.  That’s the ideology we have. Letting talented people loose to do their best work is critical; but leadership, judgment, and experience matter, too. If not, why bother having a CEO, or a VP of anything? Why not just pay everyone the same thing and hope they can all figure out the complexities of the business together?

We believe the MSMO is the best operating philosophy to allow high performers to do their best work. 

At Bolster, we are leaning into things like social contracts, peer feedback, career mentorship, individuals translating our Operating Framework into priorities and work, flexible work streams and team leadership, instead of fixed permanent hierarchies, rotating chairs of key company meetings, and market-level-based compensation.  

What we are steering away from are things like traditional titles, micromanaging or overmanaging, traditional performance reviews linked to compensation and complex incentive compensation structures, and fixed organization boundaries and structure.

We’ll see if our MSMO Operating Philosophy works. If not, we’ll iterate on it. That’s the good thing about adherence to an ideology of philosophy as opposed to an ideology of practices. Who knows – maybe the MSMO concept and even its quirky name will catch on!

Getting the Most out of Your Investors

Fred Wilson has been a venture investor and director in Return Path since 2000, first with Flatiron Partners and then with Union Square Ventures.  We’ve been through a lot of wars together.  In a couple of weeks, he and I are team-teaching a class in Entrepreneurship at Princeton, and the professor gave us the assignment of writing two pairs of blog posts to tee up discussion with the class.  The first two posts were mine on selecting investors and Fred’s on selecting investments.  This is my second one…and Fred’s post on the other side of the topic is here.

Once you’ve done a venture financing and the smoke clears, you have to transition the relationship you have with your new investor from the courting phase to building a CEO-Director relationship for the long haul.  Here are a few thoughts on how best to do optimize the relationship once it’s established.

1. Take onboarding seriously.  I always say that the hiring process for new employees doesn’t end when the employee starts…it ends 90 days later after some deliberate onboarding and a two-way review to check in and see how things are going.  Adding a new Board member is the same.  Onboard him or her with some of the same rigor and materials with which you’d onboard a new executive.  Touch base a lot early on.  Schedule an in-person 1:1 check-in after a few months to see how things are going
2. Give news early and often.  CEOs who wait until Board meetings to share all news are missing out on the point of a good director relationship, as well as missing the point of how communications work in the 2010s.  This is especially true with bad news.  No one likes to get it, but the earlier people hear it, the more they can thoughtfully process it and provide help
3. Ask for and give feedback early and often.  Though there are certainly some exceptions, venture investors are notoriously bad about giving and receiving feedback.  If you set the tone by asking for feedback regularly – then being sure to internalize and act on it and check back in to see if improvements are obvious – you can get even the most reticent director to speak up.  And there’s no reason you shouldn’t be providing feedback in near-real time as well.  Just because a director is your boss doesn’t mean he or she is meeting your expectations, and it’s a partnership, not a true hierarchical relationship
4. Ask for help and give assignments.  As a friend of mine says to her kids all the time, You don’t A-S-K, you don’t G-E-T.  If Board members don’t have specific things to work on, they either do nothing, or they do things you don’t need help on.  Drive the work like you would with any team member
5. Foster independent relationships with your team and other directors.  The hourglass model – where the CEO sits in between the Board and the management team and filters all dialog and data from one group to the other – is outdated.  A director will be much more able to add value to you and to the organization if he or she has an independent point of view as to what’s going on with your team and what other directors are thinking
6. Encourage directors to speak their minds.  As awful as company politics are, Board politics are worse.  Try to create an environment where directors aren’t shy about saying what’s really on their mind.  You don’t want to get through a Board meeting and then have someone pull you aside and say “what I really think is…”  This means you need to ask them direct questions, not be defensive in your verbal or body-language reaction, and make sure you allow for Executive Sessions at Board meetings
7. Hold directors accountable.  If you give a Board member an assignment, make sure it gets done on time and the way you asked for it.  If you have a director who is sitting in your Board meetings doing email the whole time, politely (and maybe privately, at least the first time) call him out on it.  If you don’t hold directors accountable, then just like your staff, they will learn that you don’t really mean what you say
8. Use their time wisely.  No one likes to waste time – certainly not professional investors who sit on a dozen boards.  Get Board materials out early, run productive Board meetings, and while you include some social element like a dinner or outing, make sure even that has the right group and is at the right kind of venue
9. Augment the Board with independent directors.  Venture directors can be amazingly helpful resources for you and your company.  But they typically have limitations as to their range of operating experience.  If you want to build a great Board and add some counterweights to your VCs, add one or more independent directors who are experienced business operators with experience serving on Boards as well

Year ago when we both first started blogging, Fred and I wrote a whole series of Venture Cliché and Counter-Cliché posts.  Writing these two makes me realize how much fun that was!  I’m looking forward to the class at Princeton next week and to seeing the kinds of questions these four posts inspire.

Well, that’s a mouthful.  Let me break it down.

Ideas Matter Less Than Execution

Execution Matters Less Than Timing

Timing Matters Less Than Luck

There’s a persistent myth about entrepreneurs as heroes – the people with the brilliant ideas and Eureka moments that bring companies to life and create success.  I’ve never believed in that myth, or at least not in its universality, as I’ve always valued both ideation and execution in terms of business building.  But as I was thinking about that construct more the other day, it occurred to me that there’s actually a hierarchy of the two, and not just of the two, but of timing and luck as well.  The best businesses — the runaway successes — probably have all four of these things going, or at least three.  And in many cases, THE IDEA is the least important of the bunch.  Consider these examples:

Plaxo was launched a year or two before LinkedIn.

Friendster was launched a couple years before MySpace, which was launched before Facebook.  (You can go back even further and look at things like PlanetAll and Classmates.com).

Geocities predated blogging and Tumblr by more than a decade.

The Diamond Rio was launched three years before the first iPod.

Lycos, Excite, Infoseek, Altavista, Yahoo, and lots of other search engines and web crawlers were started well before Google.  Goto.com (Overture) did paid search before Google.

The ideas were all pretty similar.  In most cases, if not all, execution won out.  In the case of the iPod vs the Rio, it’s not that the world wasn’t ready for portable music – my Sony Walkman from the early 1980s is testament to that.  It’s that the combination of iTunes and the iPod, combined with Apple’s phenomenal design and packaging — all elements of execution — won the day.

The role that timing plays is also key.  Sometimes the world isn’t ready for a great technology yet, or it may be ready, but not for sustained growth and usage.  Friendster and MySpace vs. Facebook is the best example of this.  Facebook isn’t necessarily a better service, better marketed.  Friendster and MySpace were similarly viral in adoption at the beginning.  But the world was still in the Visionary or Early Adopter stage (in the language of Geoffrey Moore’s Crossing the Chasm).  By the time Facebook came around, the world was ready to mass adopt a social network.  Geocities, for example, was a big financial success at the time (Yahoo acquired the business for $5B – they “only” acquired Tumblr for $1B, give or take), but then it disappeared from the scene, where Tumblr seems much more durable.

The role of luck is harder to explain, or at least harder to separate from that of timing, and there’s a good argument that luck can be at the bottom of this particular chain, not the top (as in, luck is hard to separate from ideas).  Sometimes luck means avoiding bad luck, as in the story about Southwest Airlines — a great idea with promising early execution and good timing — narrowly avoiding a major crash during its first week of operations in 1967.  Sometimes luck means being in the right place at the right time, or making an accidental discovery, as in the case of the Princeton University professor, Edward Taylor, who discovered a powerful cancer treatment a bit accidentally while studying the pigments that produce the colors on the wings of butterflies for a completely unrelated purpose.

Don’t get me wrong.  Ideas are still important.  They are the spark that starts the fire.  And ideas can be partly created by the luck of being in the right place at the right time, so maybe this whole construct is more of a virtual circle than a hierarchy.  But entrepreneurs need to remember that a spark only gets you so far.  As the old saying goes, I’d rather be lucky than good!

Innovating in New York City

Last week I wrote about speaking at the NYC Lean Startup Meetup.  One of my other key takeaways from this, which I’ve known for a while and have been meaning to blog about, is just how vibrant the tech startup community is here in New York.  I know others have been blogging about this like mad – Fred has some thoughts here, here, and here, and Charlie has some here and here.  Chris Dixon’s seminal post on this is here. (I even blogged a bit about why NYC is a good place to start a business back in 2006 here.)

I’ve had a little more time for networking and speaking in the past year than the prior year, and I’ve been blown away by how many startups there are here.  Like most things, New York City is such a massive and diverse place that it’s easy to “get lost in the crowd,” and there’s a lot going on.  So startups don’t tend to get the same level of social buzz that they do in Silicon Valley.  But Fred’s stat in one of those links above that over 150 startups were founded in NYC this year compared to over 300 in the Valley is interesting when you consider the geographic density here.  There are many more per square mile in New York.

Despite the geographic density to the startups, the New York startup scene is a long way from being a community.  There are some encouraging signs of late.  Charlie’s establishing a physical presence for First Round Capital is one. NextNY, with over 2500 members, is another, along with various Meetups.  I am learning more and more every day about local incubator-type organizations as well (take that term with a grain of salt).  I thought John Borthwick’s Betaworks was the only one until Charlie told me about Sunshine Suites, TechSpace, and the NYU/Poly program.  But something is still missing.  Some glue to hold it all together.

In the Valley, the startup community is  a cultural thing — plus, startups are part and parcel of a larger tech community.  Most of the big acquirers of internet companies are out there, so the ecosystem keeps cycling through companies and talent and investors.  In smaller cities like Denver/Boulder and Boston (and soon to be Seattle), TechStars fills a good void by providing a high profile “lure the talent here” combined with “meet the money” program. Seedcamp does that nicely in London, which, while it’s a big city, has a much smaller and more dispersed startup community than New York.

Since we’re unlikely to suddenly sprout a bunch of Fortune 500 tech companies in NYC, where’s our version of one of those programs in NYC?  Or is there some other “glue” lurking out there to tie it all together?

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.)

Stamina

A couple years ago I had breakfast with Nick Mehta, my friend who runs the incredibly exciting Gainsight.  I think at the time I had been running Return Path for 15 years, and he was probably 5 years into his journey.  He said he wanted to run his company forever, and he asked me how I had developed the stamina to keep running Return Path as long as I had.  My off the cuff answer had three points, although writing them down afterwards yielded a couple more.  For entrepreneurs who love what they do, love running and building companies for the long haul, this is an important topic.  CEOs have to change their thinking as their businesses scale, or they will self implode!  What are five things you need to get comfortable with as your business scales in order to be in it for the long haul?

Get more comfortable with not every employee being a rock star.  When you have 5, 10, or even 100 employees, you need everyone to be firing on all cylinders at all times.  More than that, you want to hire “rock stars,” people you can see growing rapidly with their jobs.  As organizations get larger, though, not only is it impossible to staff them that way, it’s not desirable either.  One of the most influential books I’ve read on hiring over the years, Topgrading (review, buy), talks about only hiring A players, but hiring three kinds of A players:  people who are excellent at the job you’re hiring them for and may never grow into a new role; people who are excellent at the job you’re hiring them for and who are likely promotable over time; and people who are excellent at the job you’re hiring them for and are executive material.  Startup CEOs tend to focus on the third kind of hire for everyone.  Scaling CEOs recognize that you need a balance of all three once you stop growing 100% year over year, or even 50%.

Get more comfortable with people quitting.  This has been a tough one for me over the years, although I developed it out of necessity first (there’s only so much you can take personally!), with a philosophy to follow.  I used to take every single employee departure personally.  You are leaving MY company?  What’s wrong with you?  What’s wrong with me or the company?  Can I make a diving catch to save you from leaving?  The reality here about why people leave companies may be 10% about how competitive the war for talent has gotten in technology.  But it’s also 40% from each of two other factors.  First, it’s 40% that, as your organization grows and scales, it may not be the right environment for any given employee any more. Our first employee resigned because we had “gotten too big” when we had about 25 employees.  That happens a bit more these days!  But different people find a sweet spot in different sizes of company.  Second, it’s 40% that sometimes the right next step for someone to take in their career isn’t on offer at your company.  You may not have the right job for the person’s career trajectory if it’s already filled, with the incumbent unlikely to leave.  You may not have the right job for the person’s career trajectory at all if it’s highly specialized.  Or for employees earlier in their careers, it may just be valuable for them to work at another company so they can see the differences between two different types of workplace.

Get more comfortable with a whole bunch of entry level, younger employees who may be great people but won’t necessarily be your friends.  I started Return Path in my late 20s, and I was right at our average age.  It felt like everyone in the company was a peer in that sense, and that I could be friends with all of them.  Now I’m in my (still) mid-40s and am well beyond our average age, despite my high level of energy and of course my youthful appearance.  There was a time several years ago where I’d say things to myself or to someone on my team like “how come no one wants to hang out with me after work any more,” or “wow do I feel out of place at this happy hour – it’s really loud here.”  That’s all ok and normal.  Participate in office social events whenever you want to and as much as you can, but don’t expect to be the last man or woman standing at the end of the evening, and don’t expect that everyone in the room will want to have a drink with you.  No matter how approachable and informal you are, you’re still the CEO, and that office and title are bound to intimidate some people.

Get more comfortable with shifts in culture and differentiate them in your mind from shifts in values.  I wrote a lot about this a couple years ago in The Difference Between Culture and Values . To paraphrase from that post, an organization’s values shouldn’t change over time, but its culture – the expression of those values – necessarily changes with the passage of time and the growth of the company.  The most clear example I can come up with is about the value of transparency and the use case of firing someone.  When you have 10 employees, you can probably just explain to everyone why you fired Joe.  When you have 100 employees, it’s not a great idea to tell everyone why you fired Joe, although you might be ok if everyone finds out.  When you have 1,000 employees, telling everyone why you fired Joe invites a lawsuit from Joe and an expensive settlement on your part, although it’s probably ok and important if Joe’s team or key stakeholders comes to understand what happened.  Does that evolution mean you aren’t being true to your value of transparency?  No.  It just means that WHERE and HOW you are transparent needs to evolve as the company evolves.

• Get more comfortable with process.  This doesn’t mean you have to turn your nimble startup into a bureaucracy.  But a certain amount of process (more over time as the company scales) is a critical enabler of larger groups of people not only getting things done but getting the right things done, and it’s a critical enabler of the company’s financial health.  At some point, you and your CFO can’t go into a room for a day and do the annual budget by yourselves any more.  But you also can’t let each executive set a budget and just add them together.  At some point, you can’t approve every hire yourself.  But you also can’t let people hire whoever they want, and you can’t let some other single person approve all new hires either, since no one really has the cross-company view that you and maybe a couple of other senior executives has.  At some point, the expense policy of “use your best judgment and spend the company’s money as if it was your own” has to fit inside department T&E budgets, or it’s possible that everyone’s individual best judgments won’t be globally optimal and will cause you to miss your numbers.  Allow process to develop organically.  Be appropriately skeptical of things that smell like bureaucracy and challenge them, but don’t disallow them categorically.  Hire people who understand more sophisticated business process, but don’t let them run amok and make sure they are thoughtful about how and where they introduce process to the organization.

I bet there are 50 things that should be on this list, not 5.  Any others out there to share?