The old carpenter’s axiom of being extra careful to plan before executing is something not enough executives take to heart in business. Just like cutting a piece of wood a little too long, sometimes you execute in ways that can be modified on the fly; but other times, just like the cases where you cut a piece of wood too short, you can’t. And of course, in business, sometimes it’s somewhere in between. Some examples:

• One example that’s a little more literal is around cutting staff or planning a layoff. Layoffs are traumatic for everyone involved – mostly those impacted, but for you as CEO and for your remaining organization as well. Being thoughtful about how much you cut and (unlike the case of a piece of wood) erring on the side of cutting more than you think you need to can prevent you from having to do a second set of even more traumatic layoffs down the road
  
• Getting a lease on a new office? Plan, plan, and plan again – you can end up spending too much if you get too much space and can’t sublet it…you have a real headache if you don’t get enough space and need to scramble for more
  
• Planning a major investment in a new product? You don’t want to spin up a whole new effort internally and hire people before you’ve done enough discovery and planning to know it’s worth it

It’s an interesting question as to whether or not this axiom conflicts with the startup mentality of moving quickly and with agility. I don’t think it does, although in the startup ecosystem, a lot of fixed decisioning has moved to variable, which means you may be faced with fewer times where you need to measure twice. For example, a lot of SaaS licenses you have to buy are per-seat, or AWS costs are fluid. All that is much easier than perpetual license software models or standing up servers in a data center.

I’m a big fan of Eisenhower’s line that “plans are nothing but planning is everything.” That’s why I like to measure twice, cut once when I’m working on something big. It just raises the odds of getting it right, whatever it is.

The Nachos Don’t Have Enough Beef in Them

Short story, two powerful lessons.

Story:  I’m sitting at the bar of Sam Snead’s Tavern in Port St. Lucie, Florida, having dinner solo while I wait for my friend to arrive.  I ask the bartender where he’s from, since he has a slight accent.  Nice conversation about how life is rough in Belfast and thank goodness for the American dream.  I ask him what to order for dinner and tell him a couple menu items I’m contemplating.  He says, “I don’t know why they don’t listen to me.  I keep telling them that all the people here say that the nachos aren’t good because they don’t have enough beef in them.”  I order something else.  Five minutes later, someone else pounds his hand on the bar and barks out “Give me a Heineken and a plate of nachos.”  The bartender enters the order into the point-of-sale system.

Lesson 1:  Listen to your front-line employees – in fact, make them your customer research team.  I’ve seen and heard this time and again.  Employees deal with unhappy customers, then roll their eyes, knowing full well about all the problems the customers are encountering, and also believing that management either knows already or doesn’t care.  Or both.  There’s no reason for this!  At a minimum, you should always listen to your customer-facing employees, internalize the feedback, and act on it.  They hear and see it all.  Next best prize – ask them questions.  Better yet – get them to actively solicit customer feedback.

Lesson 2:  Always remember another person’s person-ness, especially if he or she is in a service role.  The old story about the waiter spitting and coughing in the obnoxious customer’s soup would dictate that self-preservation, if nothing else, should inspire civility towards people who are serving you, be it a B2B account manager or a waiter in a diner.  Next best prize – self-interest to get a higher level of service.  Better yet – engagement and kindness like you’d want people to show you.  Chances are, they’re trying to make your day a bit better.  Shouldn’t you try to do the same for theirs?

(Lesson 3:  Always listen to your bartender!)

Almost a year into my second journey as a startup CEO at Bolster, and I’m getting more and more questions from other CEOs about what it’s like doing a second startup after almost 20 years at the first one…and achieving pretty good scale by the end.  The short answer is, it’s the same, only it’s way better.  Here’s why.

I’m more confident.  So is our whole founding team.  When Jack and I started Return Path, we were 29.  This time, we were 49 — and the average age of the founders was probably 46 or 47.  The bottom line is that we don’t know everything about the business we’re building, but we know what we’re doing in terms of building a business, a startup, a software company, a service-oriented business, leading a team, planning, executing, and on and on.  Confidence in all of those areas means large portions of our day and brain space are freed up to focus on the actual construction of the business without worrying if we’re doing things right or wrong.

It’s much easier to build a startup today.  1999 wasn’t the dark ages, but it feels like a different millennium in terms of what it’s like to start a technology company from scratch.  The cloud and micro services/APIs mean that we are able to build our platform much more quickly at much lower cost than in the past.  And in terms of tooling the business, we got up and running with about 20 different DIY cloud/SaaS solutions in about 6 weeks for a cost of less than $10k/year.

We are sharper on execution and impatient for success.  Your first startup in your 20s is a lot about “enjoying the startup journey.”  This time around, our team is significantly more focused on critical stage-gate success metrics.  In both cases of course, the objective was to win, but this time around, we are much more focused on getting to that point sooner and with less waste.

We are a lot more productive.  Ok, fine, we’re cheating because of COVID and working from home.  No train commutes.  No plane trips.  No water cooler chatter.  No fluff.  It’s not sustainable, and I’ll write about that more in a future post.  But it’s leading to a surge of productivity like I’ve never experienced or seen before in my career.  I do like to think at least some of it comes from professional maturity — we’ll see when life returns to something more closely approximating normal.

I am having a blast being on the front lines.  I went from running a 500-person company, where I’d honed my job and skill set around communication, people issues, and mobilizing the army to go do things…to spending less than 5% of my time running the company and managing people.  Now depending on the moment, I’m an SDR, a customer success manager, a product manager, and a marketing copywriter.  And probably some other things, too.  And I love every minute of it.  It’s a lot more fun to see the direct impact of my actions on the business as opposed to only really seeing the direct impact of my actions on the people in the business (and occasionally then on some aspect of the business as an individual contributor).

Maybe I’m not having a typical second startup experience.  I know some friends who had successful first exits and hated going back to square one, or failed at a second business and were really disappointed about it, only to shift careers.  But my experience so far is a much better second verse, even though it’s a bit like the first.

I wrote part I of this post in 2011, and I feel even more strongly about it today. I generally keep this blog away from politics (don’t we have enough of that running around?), but periodically, I find some common sense, centrist piece of information worth sharing. In this case, I just read a great and very short book, Six Amendments: How and Why We Should Change the Constitution, by former Supreme Court Justice John Paul Stevens, that, if you care about the polarization and fractiousness going on in our country now, you’d appreciate.

If nothing else, the shattered norms and customs of the last several years should point people to the fact that our Constitution needs some revision. Not a massive structural overhaul, but some changes on the margin to keep it fresh, as we approach its 250th anniversary in the next couple decades.

You, Too, Can Take Six Weeks Off

Note:  I have been really quite on OnlyOnce for a few months, I realize.  It’s been a busy stretch at work and at home.  I keep a steady backlog of blog topics to write about, and finally today I’ve grabbed a couple minutes on a flight to knock one out.  We’ll see if this starts me back on a more steady diet of blogging – I miss it!

I’ve written in the past about our sabbatical policy at Return Path, from what it is (here) to how much I enjoyed my own (here), to how great it is when my direct reports have been on Sabbatical so I can walk a few miles in their shoes (here and here).

But recently, a fellow CEO asked me if there was a special set of rules or advice on taking a sabbatical as a CEO.  My quick answer to his specific question was:

Well, first, you and your co-founder can’t take them at the same time. 🙂

But I have a longer list of thoughts as well.  It’s not easy, but as I’ve said many times, it’s important and wonderful.  Some tips:

• You have to make sure your balance sheet is strong and you’re not raising a round of financing
• You’re best off doing it a week or two after a Board meeting (and obviously, don’t miss one)
• You need everyone on your team to know about it and get excited for you!  They will rally/rise to the occasion more than you think
• You have to do a total disconnect, otherwise it doesn’t count.  Literally turn off email.  But make sure the team knows they can call you if there’s a true emergency
• Put someone in charge of keeping a running list of things that happened and be in charge of your “re-boarding”
• Put one person clearly in charge while you’re out, or tell your senior team that they’re responsible for collectively being in charge – either can work as long as you’re clear about it
• Be prepared to cancel or shift your plans if an emergency comes up before you leave

This last one is important.  I’ve postponed sabbaticals twice, and while it’s been a little tumultuous both at work and at home, it’s been better than going on a sabbatical and interrupting it with work, which I’ve also done.

Speaking of which…I’m coming up on my 17^th anniversary, which in our book means it’s time for another one!

The 90-Day Reverse Review

Like a lot of companies, Return Path does a 90-day review on all new employees to make sure they’re performing well, on track, and a good fit.  Sometimes those reviews are one-way from the manager, sometimes they are 360s.

But we have also done something for years now called the 90-Day Reverse Review, which is equally valuable.  Around the same 90-day mark, and unrelated to the regular review process, every new employee gets 30 minutes with a member of the Executive Committee (my direct reports, or me if the person is reporting to someone on my team) where the employee has a chance to give US feedback on how WE are doing.

These meetings are meant to be pretty informal, though the exec running the meeting takes notes and circulates them afterwards.  We have a series of questions we typically ask, and we send them out ahead of time so the employee can prepare.  They are things like:

-Was this a good career move?  Are you happy you’re here?

-How was your onboarding experience?

-How do you explain your job to people outside the company?

-What is the company’s mission, and how does your role contribute to it?

-How do you like your manager?  Your team?

-Do you feel connected to the company?  How is the company’s information flow?

-What has been your proudest moment/accomplishment so far?

-What do you like best about the company?

-If you could wave a wand and change something here, what would it be?

We do these for a few reasons:

-At the 90-day mark, new employees know enough about the company to give good input, and they are still fresh enough to see the company through the lens of other places they’ve worked

-These are a great opportunity for executives to have a “Moment of Truth” with new employees

-They give employees a chance to productively reflect on their time so far and potentially learn something or make some course correction coming out of it

-We always learn things, large or small, that are helpful for us as a management team, whether something needs to be modified with our Onboarding program, or whether we have a problem with a manager or a team or a process, or whether there’s something great we can steal from an employee’s past experiences

This is a great part of our Operating System at Return Path!

Child Prodigies, or Misspent Youths?

I just got an email from a reader of this blog with a subject line of "15 year-old entrepreneur" and a series of engaging questions around starting a business (and actually, quite a good idea for one as well).  It got me thinking about being a kid and being an entrepreneur at the same time.  The author of this email is impressively savvy and focused on the world of business and startups.

Ben Casnocha is another one.  Ben is 19, has already started two companies, and has written and published a book called My Startup Life. 

When I was 15, I actually did have an inkling that I was going to go into business someday, and probably even that I wanted to start a business someday.  After all, it’s what my dad did, and what both of my grandfathers did.  But the key words in that sentence are INKLING and SOMEDAY.  I’m not sure it would have occurred to me in a million years to actually start a real business.  I suppose I could have figured out how.  But I wasn’t interested in doing it, or I didn’t have a good peer network of business-minded teens, or something.

It’s interesting to think about whether or not I’d be a better entrepreneur or CEO today if I’d started entrepreneurial pursuits at age 15 instead of age ~25.  Certainly, one makes a huge number of mistakes the first time one does anything, so perhaps better to get those out of the way early.  But I have to imagine that there are some things that one learns with age about dealing with other people that can’t be hurried up just because one starts businesses early.

Anyway, my hat is off to guys like Ben and the even younger guy who wrote into me…I just hope they’re making enough time for more standard teenage fun with their friends as well!

Sometimes, There Is No Lesson To Be Learned

We had a very unusual employee situation this week at Return Path.  A brand new senior executive we brought in to the company to be our first ever head of HR and Organization Development resigned very abruptly after only a few weeks on the job, citing a complete change of heart about her career direction and moving on to a government position in economic and community development.  Unfortunately, the person gave no notice and provided no assistance with transition, and resigned by cell phone.  What a disappointment, especially coming from an HR professional!

After getting over my disbelief/irritation/rage (not easy, not a small amount), after communicating this difficult message to the company, and after sending a thoughtful-yet-cathartic note to the person, I sat down to think a little bit about how I could have prevented or at least spotted the situation in advance.

We interviewed the person thoroughly — 10 people internally conducted interviews, and I interviewed the person for almost four hours myself, conducting one of the most rigorous interviews I’ve ever conducted given how critical this position was to our organization at this time.  (The interview followed the Chronological In-Depth Structured interview format from Brad Smart’s book Topgrading — more on that in a future posting.)  I also checked five references on the person, all of which were sterling.  I had one outside person, an executive coach with whom I work, interview the person.  Everything checked out, and the person’s attitude and enthusiasm about the position couldn’t have been better.

My conclusion on the lesson learned here?  It’s “Sometimes, there is no lesson to be learned.”  There may be ancillary lessons around handling the situation once it became apparent, but I think the core lesson I’d hope to get out of this — that we could have done something different in the interview process or orientation or first few weeks to prevent or at least spot this ahead of time — appears to be nonexistent.  Hmmmph!

A couple of months ago, I was doing an internal lunch & learn for senior managers, and the topic came up as to “how do our VC firms work?”  In the spirit of deeply understanding our customers’ businesses in order to better serve them, I thought the same would be true of our investors and Board members – that educating our team on the inner workings and economics of our investors would lead to greater empathy of one of our other key stakeholders.

So with no small amount of help from my long-time investor and director Brad Feld and his colleague Jason Mendelson, whose book Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist I contributed to in a very small way by writing a series of sidebars called “The Entrepreneur’s Perspective” (that process led to my writing Startup CEO), I pulled together this presentation available on Slideshare entitled How Venture Capital Firms Work and Why You Should Care.

I redacted our cap table and pictures of our VCs, but otherwise, feel free to use it with your own management team, or even your whole company.

Last week, I blogged about Bolster’s Board Benchmark survey results, which really laid bare the lack of diversity on startup boards.  There are signs that this is starting to change slowly — one big one is that of all the board searches we are running at Bolster, about ⅔ of them are open to taking on first-time directors; and almost all are committed to increasing diversity on their boards.  

This is also something that I would expect to take some time to change.  Boards are small.  Independent seats aren’t necessarily easy to open up.  Seats don’t turn over often.  And they take a while to fill, as CEOs are thorough in their recruitment and selection process.

My new mantra for Startup Boards is simple:  1-1-1.  

1 member of the management team.

Then 1 independent for every 1 investor.

Simply put, this means you should grow from having 1, to 2, to 3 independent directors as your board grows from 3, to 5, to 7 members.

Here are four tough conversations you may have to have along the way, with some suggestions on how to navigate them.  All of these conversations need to come with a point of view of why independence and diversity matters to your company, a lot of empathy, and appreciation for the value the person brings to the table. 

The conversation with your co-founder about only one founder/executive on the board.  This one will be the most personally difficult, since you likely have a strong personal bond.  Expect to hear things like “Aren’t we partners in this business?” and “How come my vote doesn’t count?”  Just let your co-founder know that while of course they’re a key partner, the company has a limited number of board seats to fill — each one is a golden opportunity to get an outside perspective on your business and get really good mindshare of an industry expert and create a new brand ambassador.  You already have 100% of the mindshare and ambassadorship your co-founder has to offer.  You can make that person a board observer, you can make sure they’re in all the key board conversations, and you can even give the person some special voting right in your charter or by-laws if you need to.  But do not put them on the board.  It’s obviously easier to do this from the beginning as opposed to removing them from the board down the road, but at least try to have the conversation up front that someday, it’s going to happen (note this could be a different dynamic if the person is a founder but no longer active in the business).

The conversation with an existing VC about leaving the board to make room for new investors or an independent.  This one will be less personally difficult but will require you to be very artful since the VC is likely contractually given a board seat – meaning you’ll have to get them to give it up voluntarily.  You may also want to align with another VC on your board to help the conversation or process along.  Depending on the circumstances at hand, your key points of logic could be one of the following:  (1) you don’t own as high a percentage of the company as you once did, and I’d like to make room for the new lead investor to join the board without compromising our independents or making the board too big; or (2) I’d like to replace you with an independent director who brings operator perspective and comes from an underrepresented group – it’s important to me that we build a diverse board, and it’s not great that we have don’t have gender or race/ethnic diversity on our board in this day and age.  As with a co-founder, you could change this person’s designation to a board observer so they’re still present for key conversations, you’re not changing their Information Rights, which are likely contractually given in your charter, and if required, you can give the person or firm some sort of special voting rights if there’s something they can no longer block (but which they have a contractual right to block) by losing their board vote.

The conversation with a new potential investor about not taking a board seat.  If you have a big new lead investor writing a $40mm check into a growth round, you may not have a leg to stand on.  But new investors who write smaller checks as you get larger, who might only be buying a 5-10% stake in the business…there, you might have some wiggle room to negotiate.  Your best bet is to do it early in the process before you have a term sheet, and do it as an exploratory conversation.  Otherwise, your talking points are the same as talking to an existing investor above. Investors are starting to realize the power of a diverse board, and may be open to this conversation. Some are making this a proactive practice, notably two of my long-time investors and directors Fred Wilson and Brad Feld (and some of their partners at Union Square Ventures and Foundry Group) — and those investors have also been willing to mentor the new, first time board members once they join.

The conversation with an existing independent director about leaving the board when their term is up.  Perhaps you have an existing independent director who is not adding to the diversity of the board, but you already have a full board.  Or perhaps your existing independent director isn’t doing a great job or has grown stale in the role.  Once a director is fully vested, you have an easy opportunity to thank them graciously and publicly for their service, extend their option exercise period multiple years, and affirm that they’ll still take your call if you need help on something.  You should set this expectation up front when you give the director their initial grant.  If they ask why you’re not renewing them, you can simply say something like “We’d like to add some fresh outside perspective to the team.”  One thing to think about, particularly for early stage companies, is only giving new directors a 1 or 2-year vest on their first option grant, so you can make sure they’re a high value director…and so you can have the option of an easy exit (or re-up) in a shorter period of time than a traditional 4-year vest.

The net of it is that as CEO of a venture-backed company, you wield an enormous amount of (mostly soft) power around the composition of your board – probably a lot more than you think.  You just have to wield that power gently and focus on the importance of building a diverse board in terms of both experience and demographics.

Two Ears, One Mouth

Brace yourself for a post full of pithy quotes from others.  I’m not sure how we missed this one when drafted our original values statements at Return Path years ago, because it’s always been central to the way we operate.  We aren’t just the world’s biggest data-driven email intelligence company – we are a data-driven organization.  So another one of our newly written Core Values is:

Two Ears, One Mouth:  We ask, listen, learn, and collect data.  We engage in constructive debate to reach conclusions and move forward together.

I’m not sure which of my colleagues first said this to me, but I’m going to give credit to Anita, our long-time head of sales (almost a decade!), for saying “There’s a reason God gave you two ears and one mouth.”  The meaning?  Listen (and look, I suppose) more than you speak.

This value really has two distinct components to it, though they’re closely related.  First, we always look to collect data when we need to understand a situation or make a decision.  To quote our long-time investor, Board member, and friend Brad Feld, “the plural of anecdote is not data.”  That means we are always looking far and wide for facts, numbers, and multiple perspectives.  Some of us are better than others at relying on second-hand data and observations from trusted colleagues, which means often times, many of us are collecting data ourselves to inform a situation.  But regardless, we always start with the data.

Second, we use data as the foundation of our decision-making process.  I heard another great quote about this once, which is something like, “If we are going to make a decision based on data, the data will make the decision for us.  If we’re going to use opinion, let’s use mine.”  And while I’m at it, I’ll throw in another great quote from Winston Churchill who famously said “Facts are stubborn things.”  While we do have constructive debates all across our organization, those debates are driven by facts, not emotion.

Finally, when this value says that “we move forward together,” that is the combination of the points in the two prior paragraphs.  People may have different opinions entering a debate.  Even with a lot of data behind a decision, they may still have different opinions after a decision has been made.  But we work very deliberately to all support a decision, even one we may disagree with, and we are able to do that, move forward together, and explain the decision to the organization, because the decision is data-driven.