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

Like all CEOs and VCs, I’m a big believer in the power of pattern matching. I just wrote a whole blog post about the limits of pattern matching after hearing the quote above at a board meeting recently. But then a little alarm rang in the back of my head, and realized that I wrote about the value and limitations of pattern matching here years ago with an even better quote from my father-in-law:

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

So rather that rewrite that entire post, I thought I’d just add onto it a bit here with a current example in my head about executive recruiting and hiring executives. But then I realized I wrote that as well – the myth of the playbook. Think I’ve been blogging too long now, or what?

So let’s focus on these two angles instead: first, how do you know when you’re in a situation where You’ve Seen One, You’ve Seen Them All, or if you’re in a situation where You’ve Seen One, You’ve Seen One? And second, how can you protect yourself from a “seen one, seen one” situation when you are approaching the situation as “seen one, seen them all”?

Here are three ways to think about the decode – is this a pattern or is it a one off?

1. The list is long. It’s not actually Seen One… so much as it’s Seen X. The longer the list, the more likely you’re seeing a link in a chain instead of a one-off
2. The item is more everyday/less bespoke. Back to my example in the playbook post I referenced above, hiring a late-stage CFO is bespoke. Hiring an entry level collections person for your AR team is a lot more everyday
3. The item is more specialized. No two companies are exactly alike. No two SaaS companies are alike, but they’re more alike than two random companies. No two B2B SaaS companies are alike, but they’re even more alike than two SaaS companies. B2B SaaS companies with email marketing platforms. B2B SaaS companies with email marketing platforms serving SMBs. You get the idea

And here are a couple tactics to mitigate against calling a pattern where a pattern doesn’t exist:

1. Do a premortem (I wrote about this concept in this post) and ask yourself “If this turns out to be wrong, what are the possible reasons it was wrong?”
2. Build a very small bullet-point level mitigation plan against the top three reasons you come up with

There’s no guarantee that the sound you hear is horses and not zebras. But these indicators may help raise the odds that your pattern match is on point or protect against an unexpected herd of zebras.

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.

You Have to Throw a Stone to Get the Pond to Ripple

This is a post about productive disruption.  The title comes from one of my favorite lines from a song by Squeeze, Slap & Tickle.  But the concept is an important one for leaders at all levels, especially as businesses mature.

Founders and CEOs of early stage companies don’t disrupt the flow of the business.  Most of the time, they ARE the flow of the business.  They dominate the way everything works by definition — product development, major prospect calls, client dialog, strategy, and changes in strategy.  But as businesses get out of the startup phase and into the “growth” phase (I’m still trying to figure out what to call the phase Return Path is in right now), the founders and CEO should become less dominant.  The best way to scale a business is by not being Command Central any longer – to build an organization capable of running without you in many cases.

Organizations that get larger seek stability, and to some extent, they thrive on it.  The kinds of people you hire into a larger company aren’t accustomed to or prepared for the radical swings you get in startups.  And the business itself has needs specifically around a lack of change.  Core systems have to work flawlessly.  Changes to those systems have to go off without a hitch.  Clients need to be served and prospects need to be sold on existing products.  The world needs to understand your company’s positioning and value proposition clearly — and that can’t be the case if it’s changing all of the time.  Of course innovation is required, both within the core and outside of it, but the tensions there can be balanced out with the strengths of having a stable and profitable core (see my colleague George Bilbrey’s guest post on OnlyOnce a couple months back for more discussion on this point).

Despite all of this required stability, I think the art of being a leader in a growth organization is knowing when and how to throw that stone and get the pond to ripple — that is, when to be not just disruptive, but productively disruptive.

If done the right way, disruption from the top can be incredibly helpful and energizing to a company.  If done the wrong way, it can be distracting and demotivating.  I’ve been in environments where the latter is true, and it’s not fun.  I think the trick is to figure out how to blaze a new trail without torching what’s in place, which means forcing yourself to exercise a lot of judgment about who you disrupt, and when, and how (specifically, how you communicate what it is you’re doing and saying — see this recent post entitled “Try It On For Size” for a series of related thoughts).

Here are a few ideas for things that I’d consider productive disruption.  We’ve done some or shades of some of them at Return Path over the years.

• Challenge everyone in the organization or everyone on your team to make a “stop doing” list, which forces people to critically evaluate all their ordinary processes and tasks and meetings and understand which ones are outdated, and therefore a waste of time
• With the knowledge and buy-in of the group head, kick off an offsite meeting for a team other than the executive team by presenting them with your vision for the company three years down the road and ask them to come back to you in a week with four ideas of how they can help achieve that vision over time
• If you see something going on in the organization that rubs you the wrong way, stop it and challenge it.  Do it politely (e.g., pull key people aside if need be), but ask why it’s going on, how it relates to the company’s mission or values as the case may be.  It’s ok to put people on the defensive periodically, as long as you’re asking them questions more than advocating your own position

I’m not saying we have it all figured out.  I have no doubt that my disruption is a major annoyance sometimes to people in the organization, and especially to people to report to me.  And I’ll try to perfect the art of being productive in my disruption.  But I won’t stop doing it — I believe it’s one of the engines of forward progress in the organization.

Shifting Gears

My Grandma Hazel has a Yiddish saying that she uses to describe me from time to time — "gor oder gornisht" — which means "all or nothing."  My Dad has a Greek saying that he uses to describe me from time to time — "meden agan" — which means "everything in moderation."  These two approaches to life seem diametrically opposed.  Which is right?

Being a successful entrepreneur requires BOTH approaches, each at different times, and more important, the ability to shift gears between the two and be clear about the shift to yourself and to others.

There are periods of time when you need to be in "all or nothing mode."  Push extremes.  Demand more from your team.  Drop lots of the items on your to-do list and grow a singular focus on The One Big Thing.  Don’t go for a light jog — train for a marathon.

Then there are periods of time when you’re in execution mode.  The path has been defined.  Things are working.  Put the "life" back in your "work-life" balance.  A marathon?  Are you nuts?  Just run 3 miles a day and stay in shape.

You — and your organization — need to be able to shift gears between the two modes.  An organization that never goes through extreme periods is in grave danger of stagnating.  No one in an exciting company ever has "business as usual" emblazoned on their to-do list 365 days a year.  Organizations tend to take their biggest leaps forward when there’s an extreme situation, an all-hands on deck, a crisis.

But an organization that ONLY knows how to exist in crisis mode can be miserable.  Trust me, I’ve worked in one before.  There’s a shiny new object every week that everyone has to drop everything to pursue.  Everything gets started, but nothing gets finished.  People are frustrated.  They burn out. 

Companies and people (most mortals, anywway) have to go through periods of time where they thrive on the routine and celebrate their everyday achievements.

The trick to getting this duality right is to make sure you are clear to yourself, and when necessary to others, about when you’re shifting gears.  For yourself:  when you go into "gor oder gornisht" mode, clear that calendar and set aside the time to do the job right.  For others:  don’t make them guess where you’re coming from.  If you’re hitting an extreme patch, let them know by meeting or email/memo.  And make sure you’re fair to them as well.  If you’re forcing people in the organization to focus on The One Big Thing, make sure you recognize the changes that forces in their goals, their deliverables, and their external commitments and give them the flexibility they need to succeed.  Going back into "meden agan" mode is easier, but still requires a note of closure to your team, celebrating the success of the big push.

Fortunately, I can tell both Dad or Grandma that they’re right (how would I ever pick?).  I just hope the ancient Greek philosophers and bubbies everywhere aren’t spinning in their graves over the mixing of metaphors.

Last week, I wrote about surrounding yourself with the best and brightest.  Next in this series of posts  is all about Creating an environment of trust.  This is closely related to the blog post I wrote a while back in my series on Return Path’s Core Values on Transparency.  At the end of the day, transparency, authenticity, and caring create an environment of trust.

Some examples of that?

• Go over the real board slides after every board meeting – let everyone in the company know what was discussed (no matter how large you are, but of course within reason)
• Give bad news early and often internally.  People will be less freaked out, and the rumor mill won’t take over
• Manage like a hawk – get rid of poor performers or cultural misfits early, even if it’s painful – you can never fire someone too soon
• Follow the rules yourself – for example, fly coach if that’s the policy, park in the back lot and not in a “reserved for the big cheese” space if you’re not in Manhattan, have a relatively modest office, constantly demonstrate that no task or chore is beneath you like filling the coke machine, changing the water bottle, cleaning up after a group lunch, packing a box, carrying something heavy
• When a team has to work a weekend , be there too (in person or virtually) – even if it’s just to show your appreciation
• When something really goes wrong, you need to take all the blame
• When something really goes right, you need to give all the credit away

Perhaps a bit more than the other posts in this series, this one needs to apply to all your senior managers, not just you.  Your job?  Manage everyone to these standards.

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!

I wrote a post the other day about innovating employee benefits practices, and I realized I’d never documented a couple other ways in which we have always tried to innovate People practices. Here’s one of them: the Open Expense Policy, which I wrote about in the second edition of Startup CEO in a new chapter on Authentic Leadership when talking about the problem of the “Say-Do” gap.  Here’s what I wrote:

I’ll give you an example that just drove me nuts early in my career here, though there are others in the book.  I worked for a company that had an expense policy – one of those old school policies that included things like “you can spend up to $10 on a taxi home if you work past 8 pm unless it’s summer when it’s still light out at 8 pm” (or something like that).  Anyway, the policy stipulated a max an employee could spend on a hotel for a business trip, but the CEO  (who was an employee) didn’t follow that policy 100% of the time.  When called out on it, did the CEO apologize and say they would follow the policy just like everyone else? No, the CEO changed the policy in the employee handbook so that it read “blah blah blah, other than the CEO, President, or CFO, who may spend a higher dollar amount at his discretion.”

When we started Return Path, we had a similar policy. It was standard issue. But then over time as our culture became stronger and our People First philosophy and approach became something we evangelized more, we realized that traditional expense was at odds with our deeply held value of trusting employees to make good decisions and giving them the freedom and flexibility they needed to do their best work.

So we blew up the traditional policy and replaced it with a very simple one — “use your best judgment on expenses and try to spend the company’s money like it’s your own.” That policy is still in place today for our team at Bolster. We do have people sign off on expense requests that come in through the Expensify system, mostly because we have to, but unless there is something extremely profligate, no one really says a word.

Similar to what happened when we switched to an Open Vacation policy, we had some concerns from managers about employees abusing the new un-policy, so we had to assure them we’d have their back. But do you know what happened when we implemented the new policy? We got a bunch of emails from team members thanking us for trusting them with the company’s money. And the average amount of expenses per employees went down. That’s right, down. Trusting people to exercise good judgment and spend the company’s money as if it was their own drove people to think critically about expenses as opposed to “spend to the limit.”

I don’t think in 15+ years of operating with an Open Expense policy that any of us have had to call out an employee’s expenses as being too high more than once or twice. That’s what the essence of employee trust is about. Manage exceptions on the back end, don’t attempt to control or micromanage behavior on the front end.

As I mentioned earlier this summer, I’ve been working on a new startup the past few months with a group of long-time colleagues from Return Path.  Today, we are officially launching the new company, which is called Bolster.  The official press release is here.

Here’s the business concept.  Bolster is a talent marketplace, but not just any talent marketplace.  We are building a talent marketplace exclusively for what we call on-demand (or freelance) executives and board members.  We are being really picky about curating awesome senior talent.  And we are targeting the marketplace at the CEOs and HR leaders at venture- and PE-backed startups and scaleups.  We’re not a search firm.  We’re not trying to be Catalant or Upwork.  We’re not a job board. 

To keep both sides of the marketplace engaged with us, we are also building out suites of services for both sides – Members and Clients.  For Members, our services will help them manage their careers as independent consultants.  For Clients, our services will help them assess, benchmark and diversify their leadership teams and boards. 

We have a somewhat interesting founding story, which you can read on our website here.  But the key points are this.  I have 7 co-founders, with whom I have worked for a collective 88 years — Andrea Ponchione, Jack Sinclair, Shawn Nussbaum, Cathy Hawley, Ken Takahashi, Jen Goldman, and Nick Badgett.  We have three engineers with whom we’ve worked for several years who have been on board as contractors so far – Kayce Danna, Chris Paynes, and Chris Shealy.  We have four primary investors, who I’ve also known and worked closely with for a collective 77 years — High Alpha and Scott Dorsey (another veteran of the email marketing business), Silicon Valley Bank and Melody Dippold, Union Square Ventures and Fred Wilson, and Costanoa Ventures and Greg Sands.  Pretty much a Dream Team if there ever was one.

So how did our team and I get from Email Deliverability to Executive Talent Marketplace?  

It’s more straightforward than you’d think.  If you know me or Return Path, you know that our company was obsessed with culture, values, people, and leadership development.  You know that we created a cool workforce development nonprofit, Path Forward, to help moms who have taken a career break to care raise kids get back to work.  You know that I wrote a book for startup CEOs and have spent tons of time over the years mentoring and coaching CEOs.  Our team has a passion for helping develop the startup ecosystem, we have a passion for helping people improve and grow their careers and have a positive impact on others, and we have a passion for helping companies have a broad and diverse talent pipeline, especially at the leadership level.  Put all those things together and voila – you get Bolster!

There will be much more to come about Bolster and related topics in the weeks and months to come.  I’ll cross-post anything I write for the Bolster blog here on OnlyOnce, and maybe occasionally a post from someone else.  We have a few opening posts for Bolster that are probably running there today that I’ll post here over the next couple weeks.

If you’re interested in joining Bolster as an executive member or as a client, please go to www.bolster.com and sign up – the site is officially live as of today (although many aspects of the business are still in development, in beta, or manual).