I wrote a little bit about the experience of being a multi-time founder in this post where I talked about the value of things like a hand-picked team, hand-picked cap table, experience that drives efficient execution, and starting with a clean slate. The second lap around the track (and third, and fourth) is really different from the first lap.

Based on what we do at Bolster, and my role currently, I spend a lot of time meeting with CEOs of all sizes and stages and sectors of company, as they’re all clients or prospects or people I’m coaching. Lately, I’ve noticed a distinct set of work and behaviors and desires among CEOs who are multi-time founders and operators that is different from those same things in first-time founders. Not every single multi-time founder has every single one of these traits, but they all have a majority of them and form a pretty common pattern. I’ve noticed this with non-profit founders as well as for-profit ones.

• They have an Easier Time Recruiting team members and investors. That may sound obvious, but there are significant benefits to it. They also tend to have Much Cleaner Cap Tables, because they lived the horrors of a messy cap table when they exited their last company without thinking about that topic ahead of time!
  
• They have a Big Vision. Once you’ve had an exit, whether successful or not or somewhere in between, you don’t want to focus on something niche. You want to go all-in on a big problem.
  
• They are interested in creating Portfolio Effect. A number of repeat founders want to start multiple business at the same time, are actually doing it, or are creating some kind of studio model that creates multiple businesses. Once you have a big team, a track record with investors, and a field of deep expertise, it’s interesting to think about creating multiple related paths (and hedges) to success.
  
• They are driving to be Efficient in Execution and Find Leverage wherever they can. One multi-time founder I talked to a few weeks ago was bragging to me about how few people he has in his finance team. At Bolster, our objective is to build a big business on a small team, looking for opportunities to use our own network of fractional and project-based team members wherever possible.
  
• They are Impatient for Progress. While being mindful that good software takes time to build no matter how many engineers you hire, repeat founders tend to have fleshed out their vision a couple layers deep and are always eager to be 6 months ahead of where they are in terms of execution, which leads me to the next point, that…
  
• They are equally Impatient for Success (or Failure). More than just wanting to be 6 months ahead of where they are in seeing their vision come to life, they want to get to “an answer” as soon as possible. No one likes wasting time, but when you’re on your second or third company, you value your time differently. As a friend of mine says in a sales context, “The best answer you can get from a prospect is ‘yes’ – the second best answer you can get is a fast ‘no’.” The same logic applies to success in your nth startup. Succeed or Fail – you want to find out fast.
  
• They are Calm and Comfortable in Their Own Skin. At this stage in the game, repeat founders are more relaxed. They know their strengths and weaknesses and have no problem bringing in people to shore those things up. They know that if things don’t work out with this one, there’s more to life.
  
• They are stronger at Self Management. They are more efficient. They exercise more. They sleep more. They spend more time with family and friends. They work fewer hours.

Anyone else ever notice these traits, or others, in repeat founders?

Fred Wilson wrote an iconic blog post years ago entitled What a CEO does. In it, he outlined three broad themes:

A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank.

I wrote a response in a post entitled What Does a CEO Do, Anyway?, in which I added some specificity to those three items and added three key behaviors of successful CEOs. I also added to Fred’s list when I wrote Startup CEO, CEOs have to build and lead a board of directors, CEOs have to manage themselves, and CEOs ultimately have to think about and execute exits.

But recently, as I’ve been coaching a few CEOs, I’ve answered the question differently, because the questions have been a little less about the broad themes and more about how to prioritize — how to know what NOT to do. So in addition to Fred’s wisdom and my other thoughts above, here’s the answer I’m giving CEOs these days:

• First, do what you MUST do. There are some things that are in your job description. Do them first. You have to run your board meeting. You have to pitch investors. You have to write performance reviews for your direct reports.
• Second, do what ONLY YOU can do. There are also some things that, while not in your job description, are things that CEOs and/or founders have special impact when they do. No one can call a team member who just lost a parent or spouse and offer support and sympathy like you can. No one can get on a plane and save a key customer from leaving you like you can. No one can congratulate a sales rep on a key win like you can.
• Third, do what you’re BEST IN CLASS at. Finally, there are things that may be in other people’s job descriptions, but where you’re the stronger executer. I remember reading years ago that Bill Gates, long after he even stopped being CEO of Microsoft and was Chairman, still got involved in some major technical architecture decisions and reviews. Whatever your superpower is, or whatever it was when you were in your pre-CEO jobs, there’s no reason not to jump in and help your team excel at (and ideally train/mentor them) whenever you can.

After that, you can fill in the rest of your time with other tasks. In the world of Covey’s big rocks, this is all the sand. All the other things that come by your desk or inbox that people ask of you. They are the least important. Hopefully this is another helpful lens on how CEOs should spend their time.

I lived one of my favorite metaphors last week as we announced the closing of Bolster’s Series B financing and had our first post-round Board meeting, and I realized I’ve never blogged about it before: that raising rounds of financing is like having a good night at the blackjack table.

When I go to Vegas or AC — and admittedly I haven’t done that in several years — I usually start playing Blackjack at the $5 table. It’s lightweight entertainment, low stakes, good way to warm up and remind myself how to play. If I start winning and accumulating a bigger pile of chips, I move to the $10 table. Rinse and repeat, to the $25 table and the $50 table. I’m not sure I’ve ever been to a $100 table, and I assume there’s a somewhat tense and scary back room somewhere with higher stakes tables. As I progress through an evening, it’s more fun, but it’s also more stressful.

Raising successive rounds of financing has the same feel to it.

You’re playing the same game as you progress from Series A to Series B to Series C. You’re still CEO of your company. You may be playing with different strategies, more or less aggressive. But it feels different. It’s a little more stressful. Every bet is a higher percentage of your net worth, upside as well as downside. Expectations are higher, and external expectations are more noticeable.

What if blackjack isn’t going so well? If I am doing so-so, I just stay at the $2 table, and ultimately get bored with treading water. That’s probably the equivalent of running a company that’s just going sideways. I won’t go deep on extending the metaphor to a bad night of blackjack, but I’m sure it has a lot in common with down rounds and ultimately things like Chapter 11. Those loom large in lots of situations, too, but they’re not where my head is today!

(This is the first in a series of three posts on this topic.)

Harry Potter was lucky.  He had, in Albus Dumbledore, the ultimate wise elder, in his corner.  Someone who could teach him how to be a better human being (er, wizard), how to be more proficient with his wand and spells, how to think strategically and defeat the bad guys.

All of us would benefit from having an Albus Dumbledore in our lives.  But most of us don’t — and most of the people we’d call on to be that wise elder in our corner aren’t capable of the full range of advice and counsel that Dumbledore is. 

Why work with a Coach or a Mentor?  I’ll start this post with a quick argument in favor of CEO Coaches and Mentors (sometimes called Advisors).  Even as a 20-something first-time CEO years ago, I was deeply skeptical of the value of a Coach, but that was in 1999 or 2000 when coaches weren’t so commonplace.  Now that their value seems much more obvious, and there are so many amazing Mentors and Coaches available, I’m surprised by how many CEOs I speak to still seem skeptical about their value.  Just think — the world’s greatest athletes, the ones who get paid zillions of dollars because they are the best in the world at something, use MULTIPLE coaches DAILY to perfect their craft and keep them focused.  Why should Rafael Nadal or Serena Williams have a trainer and a coach, but not you?

I’ve benefited over the years from the advice of more people than I can ever count or thank.  But when it comes to being a CEO, I have leveraged the counsel of a CEO Coach or Mentor principally in three different areas:

1. Functional topics on the craft of being a CEO from the lofty “how to run a board meeting” to the nitty gritty details of “how to do a layoff”
2. Developmental/behavioral topics like “how I show up as a leader in the organization,” or “how to be a better listener”
3. Team Effectiveness topics like “how do I get the most out of my leadership team,” or “why doesn’t Person X trust Person Y and how does that impact team performance?”

In some unusual circumstances, you can find a person who does all three of these things for you and can scale as you and your company grow.  But for the most part, getting all three of these things requires engaging two different people, and maybe even more mentors.  

What’s the difference between a CEO Mentor and a CEO Coach?  Counsel on Item 1 above — what I would call CEO Mentorship — almost certainly requires someone to have been a CEO — preferably multiple times, or for a long period of time, or through multiple stages of company growth, or two or three of those qualifiers.  This is the kind of person who can literally teach you how to do CEO things.  These people are super busy, they won’t have open ended amounts of time for you, but you should expect sage wisdom and answers when you need them.  And you can have more than one of them at a time, or change them out as your company evolves and your needs change.

Counsel on items 2 and 3 — what I would call CEO Coaching — frequently come together in a professional who is and has been for a while, a coach.  The person might have had a significant career in business before becoming a coach but wasn’t necessarily a CEO.  The person probably has some kind of academic grounding, like a Master’s degree in Organizational Development or Industrial Psychology, or a Certificate in Coaching.  This is the kind of person who can do things for you and your team like facilitate meetings, run assessments like Myers-Briggs or DISC, and coach other leaders on your team.  This person is dedicated to helping you be the best leader, professional, and CEO that you can be and must be both empathetic and comfortable pushing you hard.  

Sometimes you get mentorship and coaching in the same person, but almost only with CEO Coaches who are also CEO Mentors by my definition above.

Five signs you need a CEO Mentor and/or Coach:

• You are playing ‘whack-a-mole’ — running from crisis to crisis in your organization and are not able to make time to think, be current with email, or make time for important things like hiring senior executives
• Your board is getting frustrated with you, your team and/or the lack of progress in the business
• The company isn’t scaling as fast as it should
• Your leadership team is not a cohesive team and you are in the middle of all decisions
• The company has high employee turnover and/or poor reviews on Glassdoor 

Do yourself and your company a favor and invest in a CEO Coach and Mentor(s). It’s an investment in accelerating your own and your company’s success. In later posts, I’ll talk about how to hire and best leverage both Coaches and Mentors. 

Next post in the series coming:  How to Select a CEO Mentor or CEO Coach

The Social Aspects of Running a Board

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

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

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

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

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.

The 2×4

I took a Freshman Seminar in my first semester at Princeton in 1988 with a world-renowned professor of classical literature, Bob Hollander.  My good friend and next-door neighbor Peggy was in the seminar with me.  It was a small group — maybe a dozen of us — meeting for three hours each week for a roundtable with Professor Hollander, and then writing the occasional paper.  Peggy and I both thought we were pretty smart.  We had both been high school salutatorians from good private schools and had both gotten into Princeton, right?

Then the first paper came due, and we were both a bit cavalier about it.  We wrote them in full and delivered them on time, but we probably could have taken the exercise more seriously and upped our game.  This became evident when we got our grades back.  One of us got a C-, and the other got either a D or an F.  I can’t remember exactly, and I can’t remember which was which.  All I remember is that we were both stunned and furious.  So we dropped by to see Professor Hollander during his office hours, and he said the same thing to each of us:  “Matt, sometimes you need a 2×4 between the eyes.  This paper is adequate, but I can tell it’s not your best work, it’s decent for high school but not for college, and almost all the others in the class were much more thoughtful.”

Ouch.

Ever since then, Peggy and I have talked about the 2×4, and how it helped us snap out of our own reality and into a new one with a significantly higher bar for quality.  That phrase made it into Return Path‘s lexicon years ago, and it means an equivalent thing — sometimes we have to have hard conversations with employees about performance issues.  The hardest ones are with people who think they are doing really well, when in reality they’re failing or in danger of failing.  That disconnect requires a big wakeup call — the 2×4 between the eyes — before things spiral into a performance plan or a termination.

Delivering a 2×4 between the eyes to an employee can feel horrible.  But it’s the best gift you can give that employee if you want to shake them back onto a successful trajectory.

I went to an amazing event this weekend. One of my close friends, Raj Vinnakota, started an education foundation about 7 years ago in Washington, D.C., called the SEED Foundation. The foundation’s first venture is the nation’s first urban public charter boarding school, located in the Anacostia section of town and dedicated to providing a college prep environment for kids who otherwise might not even finish high school in the inner city of D.C. The school has had a tremendous amount of national recognition, from Oprah, to Time, to Good Morning America, to Newsweek.

The school has now been up and running for six years, starting with a group of seventh graders back in 1998, and this Saturday, that first class graduated. Impressively, all 21 seniors are going to college, including some going to Princeton, Georgetown, and Penn. Alma Powell spoke at commencement. The event was one of the most moving things I’ve ever attended. The kids and their families were all so proud, and justifiably so.

Raj and I have followed fairly similar paths since meeting in college. Almost 100% of the same activities at Princeton, same first job after college at Mercer Management Consulting, lots of friends in common, similar family backgrounds. The only thing we have in common from the last 5 years, though, is that we’ve raised the same amount of money as leaders of our respective organizations — me for the for-profit Return Path, Raj for SEED.

Attending the SEED graduation gave me a twinge of guilt that I’m not doing something quite as overtly good for society, but it has an inspirational effect on me in two ways. First, it gave me hope for mankind’s future that people as talented as Raj are doing overt good for the less fortunate every single day. Second, it gave me lots of encouragement to build a successful company so that both the company, and I personally, can give back to society over time in other ways, both with money and with time.

Raj tells me that, now that he’s proven the model, he’s going to have a second school up and running by 2006, with more to come after that. All I can say is, good luck, and let me know how I can help!

How Many Thermometers Do You Need to Know the Turkey’s Done?

Full credit to my colleague Jack Abbot for using this awesome phrase in an Engineering Management meeting I observed recently. It’s a gem. Filed!  The context was around spending extra cycles creating more metrics that basically measure the same thing. And in theory, sure, you don’t want or need to do that, even if you do have a cool data visualization tool that encourages metric proliferation.

But as I was thinking about it a bit more, I think there are situations where you might want multiple thermometers to tell you about the done-ness of the turkey.

First, sometimes you learn something by measuring the same thing in multiple ways.  Triangulation can be a beautiful thing.  Not only does it work for satellites, but think of a situation where you have a metric that is really made up of multiple underlying metrics.  Net Promoter Score is a good example.  Aren’t you better off knowing the number of Promoters and Detractors as well as the Net?

Second, sometimes redundant metrics aren’t bad if there is a potential failure of one of them.  For critical systems metrics that are measured in automated ways, sometimes automation fails. The second thermometer could be thought of as a backup.  You can have an internal web performance monitoring system, but wouldn’t you feel better with Keynote or Gomez as well, just in case your internal system fails?

Finally, sometimes metrics move between “lagging” and “leading,” which are fundamentally different and useful for different purposes. For example, we talk about sales in a couple different ways here.  There are bookings, which are forward-looking, and there is recognized revenue, which is backwards looking.  They are both about revenue.  But looking only at recognized revenue tells you nothing about the health of new business.  And looking only at bookings tells you very little about the current and next quarter.

Jack, thanks for this gem of a phrase, and for the thinking it provoked!

Collaboration is Hard, Part III

In Part I, I talked about what collaboration is:

partnering with a colleague (either inside or outside of the company) on a project, and through the partnering, sharing knowledge that produces a better outcome than either party could produce on his or her own

and why it’s so important

knowledge sharing as competitive advantage, interdependency as a prerequisite to quality, and gaining productivity through leverage

In Part II, I suggested a few reasons why collaboration is difficult for most of us

It doesn’t come naturally to us on a cultural level, it’s hard to make an up-front investment of time in learning when you don’t know what you’re going to learn, and there’s a logistical hurdle in setting up the time and framework to collaborate

So now comes the management challenge — if collaboration is so important and yet so hard, how do we as CEOs foster collaboration in our organizations?  Not to say we have the formula down perfect at Return Path — if we did, collaboration wouldn’t show up as a development item for so many people at reviews each year — but here are five things we have done, either in small scale or large scale, to further the goal (in no particular order):

1. We celebrate collaboration.  We have a robust system of peer awards that call out collaboration in different ways.  I will write about this in longer form sometime, but basically we allow anyone in the company to give anyone else in the company one of several awards (all of which carry a cash value) at any time, for any reason.  And we post the awards on the Intranet and via RSS feed so everyone can see who is being appreciated for what reason.  This tries to lower the cultural barriers discussed in the last post.
2. We share our goals with each other.  This happens on two levels, and it’s progressed as the company has gotten more mature.  On a most basic level, we are very public about posting our goals to the whole company, at least at the department level (soon to be at the individual level), so everyone can see what everyone else is working on and note where they can contribute.  But that’s only half the battle.  We also have increasingly been developing shared goals — they show up on your list and on my list — so that we are mutually accountable for completing the project.
3. We set ourselves up for regular collaborative communication.  Many of our teams and departments use the Agile framework for work planning and workflow management, including the daily stand-up meeting as well as other regularly scheduled communication points (see other posts I’ve written about Agile Development and Agile Marketing).  Agile takes out a lot of the friction caused by logistical hurdles in collaborating with each other.
4. We provide financial incentives for collaboration.  In general, we run a three-tiered incentive comp program.  Most people’s quarterly or annual bonuses are 1/3 tied to individual goals achievement (which could involve shared goals with others), 1/3 tied to division revenue goals (fostering collaboration within each business unit), and 1/3 tied to company financial performance (fostering at least some level of collaboration with others outside your unit).  This helps, although on its own certainly isn’t enough.
5. We provide collaboration tools.  Finally, we have had developed reasonably good series of internal tools — Wiki, Intranet, RSS feeds — over the years, all of which are about to be radically upgraded, to encourage and systematize knowledge sharing.  This allows for a certain amount of "auto collaboration" but hopefully also allows people to realize how much there is to be gained by partnering with other subject matter experts within the company when projects call for it, alleviating in part the "you don’t know what you don’t know" problem.

So that’s where we are on this important topic.  And I’m only finding that it gets more important as the company gets bigger.  What are your best practices around fostering collaboration?

Why I Love My Board

Fred may be the only one of my directors who has done something this dorky, this publicly, but quite frankly, I could see any of us in the same position.  Guys, next meeting, we’re having nerd olympics.