(This post also appeared on Bolster.com)

As we wrote in our Founding Manifesto, Bolster was started in part to create a new way for startup and scaleup CEOs to think about growing their leadership teams.

Why do CEOs need help with this?

CEOs of any company have too many things to do at all times. This is even more true at startups and scaleups, which by definition are more fast-paced, dynamic, CEO-driven, and thinly staffed. All those challenges point directly to the specific challenge CEOs have with their leadership team.

Think about the journey of a company from a founding team to 50 employees. My long time friend and former board member Greg Sands once compared the phenomenon

of companies growing out of the startup stage to cell development in small organisms. Amoeba or paramecia consist of one cell, and that cell has to do everything: eat, move, sense its surroundings, and respond accordingly. When the cell divides, the new cells still need to do everything – they’re just attached to other cells. As organisms grow more complex, individual cells need to specialize. And when things get really complex, you need a liver, a spleen, a stomach, and a pancreas. By and large, startups work the same way. In the early stages, you have to hire generalists who are both willing and able to take on dozens of tasks at once. Your developers will have to speak with potential customers; your accountants will have to give advice on product direction; and the born salesperson on your team will need to put the phone down a few hours a day and set up a new employee’s computer. That’s a really different team than when you need functional managers on top of engineering, sales, etc. — not to mention needing strategic leadership of those functions as the company grows from 50 to 100 to 250 to 500 employees.

That’s the journey that startup and scaleup CEOs are on. It’s less of a journey and more of a roller coaster ride. Jason is running HR today…but tomorrow, the job of “head of HR” will be different, and Jason might or might not be capable of it. Then your VP Finance Sally gets lured away by an even hotter and sexier new startup and leaves a sudden, gaping hole on your team. Then cracks start to show up with the job Jamie is doing as your marketing director and you lose confidence that your upcoming product launch is going to be a success. Every time one of these events happens – whether it’s an actual event, or just an “aha moment” for you as CEO, you add something to your plate. You add tasks to take over work yourself. You add the task of finding a new person. You add stress from having to deal with one more critical thing.

Leveling up a leadership team is probably the hardest part of the CEO’s job. 

Why don’t current solutions meet the CEO’s needs? Well, of course they do, sometimes. The problem is that the current solutions either aren’t tailored to the needs of startup or scaleup CEOs, or they’re ad hoc and inefficient. Executive search is slow and expensive, and it produces expensive full-time executives. And no matter how good an executive search firm is, I’ve never met a CEO who has a better than 50% success rate in hiring new leaders from the outside. Ever. Add all that up – expensive, slow, medium success rate, and perhaps most important for a startup CEO, leaving you with expensive full-time headcount in multiple areas of your company – that is not a recipe for startup success when you’re sweating your burn rate.

Frequently, the CEO just taps her network for execs or for on-demand executives like the ones Bolster places — that could be asking board members or friends or advisors for suggestions. Quite frankly, those suggestions stand a better chance of success than transactional executive search since the candidate referral source is usually somewhat of an insider. But those searches are really disorganized or one-off. When a CEO turns to their network for spot help, they often aren’t running a comprehensive process, creating a serious job spec, seeing a broad set of candidates for comparisons, and the like. 

Our job at Bolster is to make all of this easier and lighter weight. The rise of the gig economy means that startups no longer need to rely on the painful binary choice of “the person/opening I have today” and “the expensive full-time exec coming in from the outside.”The new way to scale an executive team is with a mix of interim executive talent to quickly fill gaps, fractional executive talent to provide strategic oversight and guidance to a team, part-time, functional mentors/coaches/advisors to advise a less experienced functional leader, project-based consultants to fill in specific holes, and yes, the occasional full-time outside hire, possibly via a search firm (or if your fractional CXO loves your company and joins full-time!). 

With Bolster, you have a network of all those types of talent, well curated and well profiled, available for near-instant matches and near-instant start dates – and a suite of tools and services designed to help you proactively identify your needs across all your functional areas so you’re never scrambling your way out of a tight spot.

What about the existing team? If you’re a leader inside a startup or scaleup, Bolster is ALSO created for you. The painful binary choice CEOs face that I wrote above is particularly painful for you if you’re no longer scaling quickly enough. Frequently, promising junior people are layered or shuttered aside because the CEO doesn’t have the time, or the functional expertise required, to coach or mentor the person to success. Bolster creates an easy mechanism for CEOs to help pinpoint the areas in which you need growth and development as well as an easy way to find either temporary leadership or a function-specific advisor/mentor/coach to help you grow with the role and with the company.

The best startup CEOs I know are the ones who are already using multiple types of on-demand talent at the same time to help their companies along that journey from single-cell to complex organisms. I believe three years from today, the frequent usage of this kind of talent will move from the realm of early adopters to mainstream. The ones who embrace it first will have a competitive advantage.

I’ve written a lot about Boards this past year related to Bolster’s work in helping founders/CEOs build great boards:

• The New Way to Scale a Board of Directors
• My New Startup Board Mantra – 1:1:1
• The Startup Ecosystem Needs More Independent Board Members – That’s the Clearest Path to Having Better and More Diverse Boards
• Startup Boards eBook: How to Build Your Board
• Startup Boards eBook: How to Succeed in Your First Board Role

But more recently, I’ve been thinking a lot about Board effectiveness, as I’ve been working with Brad Feld and Mahendra Ramsinghani on a second edition of Startup Boards, which will be published in mid-2022. And in the middle of our feverish writing and editing, Reid Hoffman sent Brad a great document which I want to amplify here:

Some of these rituals are more important than others (or at least more widely applicable), but they’re all worth reading. I am definitely going to start incorporating some version of the “Dory and Pulse” ritual into my meetings to make sure we’re covering everything that each director wants to cover in meetings (or answer smaller things ahead of time).

Thanks to Reid for this great contribution to the world of Startup Boards.

The Best Place to Work, Part 0

I keep getting questions about a deck I’ve used several times at Techstars, Seedcamp, DreamIt, and the like which is called “7 Ideas for Creating the Best Place to Work.”  So today I will launch a 7-part series over the next 7 weeks to describe my 7 points.  As always, this is not intended to be perfect or comprehensive, but it is a bit of lessons learned over the last 12-13 years at Return Path.  It’s just 7 ideas – not the only 7 ideas.  And there’s nothing magic about the number 7, despite what George Costanza says.  Or Steven Covey.

Here’s the outline:

1. Surround yourself with the best and brightest
2. Create an environment of trust
3. Manage yourself very, very well
4. Be the consummate host
5. Be the ultimate enabler
6. Let people be people
7. Create a thankful atmosphere

Let’s go!  I will create a tag cloud for this series called Best Place to Work.

What Kind of Entrepreneur Are You?

I think there are two kinds of entrepreneurs, and sometimes, you can be both.  There is the kind that starts businesses, and there is the kind that builds businesses.

The kind of entrepreneur who starts businesses but usually doesn’t like running or building them are typically serial entrepreneurs.  How can you spot one?  They:

• Have an idea a minute and a bit of ADD – they are attracted to bright shiny objects – they can’t focus
  • Would rather generate 1 good and idea and 19 bad ones than just 1 good one
  • Are always thinking about the next thing, only excited by the possibility of what could be, not by what is
  • Are more philosophical and theoretical than practical
  • Probably shouldn’t run businesses for more than a few months
  • Are likely to frustrate everyone around them and get bored themselves
  • Are really fun at cocktail parties
  • Say things like “I thought of auctions online way before eBay!”

The second kind of entrepreneur is the kind of person who can run businesses but may or may not come up with the idea.  Typically, these people:

• Care about success, not about having the idea
• Love to make things work
• Would rather generate 1 idea and execute it well than 2 ideas
• Are problem solvers
• Are great with people
• May be less fun at cocktail parties, but you’d want them on your team in a game of paintball or laser tag

It’s the rare one who can do both of these things well.  But you know them when you see them.  Think Dell or Microsoft…or even Apple in a roundabout way if you consider the fact that Jobs hired Cook (and others) to partner with them to run the business.

People First

I do not think it’s telling that my fourth post in this series of posts on Return Path’s core values (kickoff post, tag cloud) is something called People First.  Ok, it probably should have been the first post in the series.  To be fair, it is the first value on our list, but for whatever reason, the value about Ownership was top of mind when I decided to create this series.

Anyway, at Return Path,

We believe that people come first

And we aren’t shy about saying it publicly, either.  This came up in a lengthy interview I did with Inc. Magazine last year when we were profiled for winning an award as one of the top 20 small- and mid-sized businesses to work for in America.  After re-reading that article, I went back and tried to find the slide from our investor presentations that I referred to.  I have a few versions of this slide from different points in time, including one that’s simpler (it only has employees, clients, and shareholder on it) but here’s a sample of it:

That pretty much says it all.  We believe that if we have the best and most engaged workforce, we will do the best job at solving our clients’ problems, and if we do that well, our shareholders will win, too.

How does this “people first” mentality influence my/our day-to-day activities?  Here are a few examples:

• We treat all employees well, regardless of level or department.  All employees are important to us achieving our mission – otherwise, they wouldn’t be here.  So we don’t do a lot of things that other companies do like send our top performing sales reps on a boondogle together while the engineers and accountants slave away in the office as second-class citizens.  That would be something you might see in a “sales first” or “customer first” culture
• We fiercely defend the human capital of our organization.  There are two examples I can think of around this point.  First, we do not tolerate abusive clients. Fortunately, they are rare, but more than once over the years either I or a member of my senior team has had to get on the phone with a client and reprimand them, or even terminate their contract with us, for treating one of our employees poorly and unprofessionally. And along the same lines, when all economic hell broke loose in the fall of 2008, we immediately told employees that while we’d be in for a rough ride, our three top priorities were to keep everyone’s job, keep everyone’s compensation, and keep everyone’s health benefits. Fortunately, our business withstood the financial challenges and we were able to get through the financial crisis with those three things intact.
• We walk the walk with regard to employee feedback.  Everyone does employee satisfaction surveys, but we are very rigorous about understanding what areas are making people relatively unhappy (for us, even our poor ratings are pretty good, but they’re poor relative to other ratings), and where in the employee population (office, department, level) those issues lie.  We highlight them in an all-hands meeting or communication, we develop specific action plans around them, and we measure those same questions and responses the next time we do a survey to see how we’ve improved
• We invest in our people.  We pay them fairly well, but that’s not what I’m talking about.  We invest in their learning and growth, which is the lifeblood of knowledge workers.  We do an enormous amount of internal training.  We encourage, support, and pay for outside training and education.  We are very generous with the things that allow our employees to be happy and healthy, from food to fitness to insurance to time off to a flexible environment to allowing them to work from another office, or even remotely, if their lives require them to move somewhere else
• I spend as little time as I possibly can managing my shareholders and as much time as I can with employees and prospective employees.  That doesn’t mean I don’t interact with my Board members – I do that quite a bit.  But it does mean that when I do interact with them, it’s more about what they can do for Return Path and less about reporting information to them.  I do send them a lot of information, but the information flow works well for them and simultaneously minimizes my time commitment to the process:  (1) reporting comes in a very consistent format so that investors know WHAT to expect and what they’re looking at, (2) reporting comes out with a consistently long lead time prior to a meeting so investors know WHEN to expect the information, (3) the format of the information is co-developed with investors so they are getting the material they WANT, and (4) we automate as much of the information production as possible and delegate it out across the organization as much as possible so there’s not a heavy burden on any one employee to produce it
• When we do spend time with customers (which is hopefully a lot as well), we try to spread that time out across a broad base of employees, not just salespeople and account managers, so that as many of our employees can develop a deep enough understanding of what our customers’ lives are like and how we impact them

There are plenty of companies out there who have a “shareholder first” or “customer first” philosophy.  I’m not saying those are necessarily wrong – but at least in our industry, I’ll bet companies like that end up with significantly higher recruiting costs (we source almost half our new hires from existing employee referrals), higher employee churn, and therefore lower revenue and profit per employee metrics at a minimum.  Those things must lead to less happy customers, especially in this day and age of transparency.  And all of those things probably degrade shareholder value, at least over the long haul.

Return Path Core Values, Part II

As I said at the beginning of this series, I was excited to share the values that have made us successful with the world and to also articulate more for the company some of the thinking behind the statements.

You can click on the tag for all the posts on the 13 Return Path’s core values, but the full list of the values is below, with links to each individual post, for reference:

1. We believe that people come first
2. We believe in doing the right thing
3. We solve problems together and always present problems with potential solutions or paths to solutions
4. We believe in keeping the commitments we make, and communicate obsessively when we can’t
5. We don’t want you to be embarrassed if you make a mistake; communicate about it and learn from it
6. We believe in being transparent and direct
7. We challenge complacency, mediocrity, and decisions that don’t make sense
8. We believe that results and effort are both critical components of execution
9. We are serious and passionate about our job and positive and light-hearted about our day
10. We are obsessively kind to and respectful of each other
11. We realize that people work to live, not live to work
12. We are all owners in the business and think of our employment at the company as a two-way street
13. We believe inboxes should only contain messages that are relevant, trusted, and safe

As I noted in my initial post, every employee as of August 2008 was involved in the drafting of these statements.  That’s a long post for another time, but it’s an important part of the equation here.  These were not top-down statements written by me or other executives or by our People team.  Some are more aspirational than others, but they are the aspirations of the company, not of management!

We spent the weekend in Hudson, New York, a charming, urban-renewing town about two hours north of the city. My cousins Michael & Marianne opened a wine store called Hudson Wine Merchants on the main drag in town, Warren Street (343 Warren St. to be exact, you should definitely check it out if you’re ever in Hudson).

The store opened for the first time Friday evening, and we had the first full day on Saturday. Mariquita and I, and some other friends of Michael & Marianne’s, helped do everything from stock the shelves, to clean the windows, to use the price tag gun (fun!), to work the register and the very fickle POS software, to watch my cousin’s daughter as she rode her tricycle through the store. It was fun but exhausting. It inspired a few different postings here, which I’ll work on in the coming days.

The first thought I had is that being CEO of a two-person company has a lot in common with being CEO of a 200-person company, or, I imagine, a 20,000-person company:

– You worry incessantly about keeping your customers happy and providing a great customer experience and the right product

– You have numbers running in the back of your head all the time. How much are you selling? At what margin? Are you making money?

– You work your ass off and frequently put business first in order to see it succeed

– You think about the little things, the big things, everything, 24 hours a day

Obviously, there are many differences between running a two-person company and running a much larger organization as well; of course, the biggest is managing, developing, and worrying about lots of employees’ welfare. But it struck me that there are more similarities than meet the eye.

Fred beat me to it. I wasn’t at a computer to post this yesterday on the actual 4th of July, so today will have to do. I’ve read lots of books on the American revolution and the founding fathers over the years. It’s absolutely my favorite historical period, probably because it appeals to the entrepreneur in me. Think about what our founding fathers accomplished:

– Articulated a compelling vision for a better future with home democratic rule and capitalist principles. Life, liberty, and the pursuit of happiness is really the ultimate tag line when you think about it.

– Raised strategic debt financing from, and built critical strategic alliances with France, the Netherlands, and Spain.

– Assembled a team of A players to lead the effort in Washington, Adams, Jefferson, Franklin, Hamilton, and numerous others who haven’t been afforded the same level of historical stature.

– Built early prototypes to prove the model of democratic home rule in the form of most of the 13 colonial assemblies, the Committees of Correspondence, and the Articles of Confederation.

– Relentlessly executed their plans until they were successful, changing tactics several times over the years of 1774-1783 but never wavering from their commitment to the ultimate vision.

– Followed through on their commitments by establishing a new nation along the principles to which they publicly committed early on, and taking it to the next level with the Constitution and our current form of government in 1789.

And let’s not forget, these guys accomplished all of this at a time when it took several days to get a letter from Virginia to Boston on horseback and six weeks to get a message across the Atlantic on a sailboat. Can you imagine what Washington would have been able to accomplish if he could have IMd with Adams in Paris?

So happy 4th to all, with a big thanks to this country’s founding fathers for pulling off the greatest spin-off of all time.

What Kind of Entrepreneur Do You Want to Be?

I had a great time at Princeton reunions this weekend, as always.  As I was talking to random people, some of whom I knew but hadn’t seen in a long time, and others of whom I was just meeting for the first time, the topic of starting a business naturally came up.  Two of the people asked me if I thought they should start a business, and what kind of person made for a good entrepreneur.

As I was thinking about the question, it reminded me of something Fred once told me — that he thought there were two kinds of entrepreneurs:  people who start businesses and people who run business. 

People who start businesses are more commonly known as serial entrepreneurs.  These people come up with ideas and love incubating them but may or may not try to run them longer term.  They:

– generate an idea a minute
– have a major case of ADD
– are easily distracted by shiny objects
– would rather generate 1 good and idea and 19 bad ones than just 1 good one
– are always thinking about the next thing
– are only excited by the possibility of what could be, not what is
– are more philosophical and theoretical
– probably shouldn’t run the companies they start for more than a few months, as they will frustrate everyone around them and get bored themselves
– are really fun at cocktail parties
– say things like “I thought of auctions online way before eBay!”

The second type of entrepreneur is the type who runs businesses (and may or may not come up with the original idea).  These people:

– care about success, not just having the idea
– love to make things work
– would rather generate 1 idea and execute it well than 2 ideas
– are problem solvers
– are great with people
– are maybe less fun at cocktail parties, but
– you’d definitely want them on your team in a game of paintball or laser tag

Neither one is better than the other, and sometimes you get both in the same person, but not all that often.  But understanding what type of entrepreneur you are (or would likely be) is probably a good first step in understanding whether or not you want to take the plunge, and if so, what role you’d like to play in the business.

A Better Way to Shop

I love Zappos.com.  It’s rapidly becoming the only place I buy shoes.  Their web site experience is ok – not perfect, but pretty good, but their level of service is just unbelievable.  They are doing for e-commerce (shoes in particular) what Eos is doing for air travel.

They’re always great at free shipping and have always been super responsive and very personal and authentic when it comes to customer service.  But today took the cake.  I emailed them when I placed an order for new running shoes because I also wanted to buy one of those little “shoe pocket” velcro thingies that straps onto shoelaces and holds keys and money for runners.  I didn’t find one on the Zappos site and just asked if they carried the item in case I missed it.

Less than 24 hours later, I got an email reply from Lori, a Customer Loyalty Representative there, who apologized for not carrying the item — and then provided me with a link to buy it on Amazon.com which she had researched online herself.

Zappos’s tag line on their emails says it all:

We like to think of ourselves as a service company that just happens to sell shoes.

Does your company think of itself and its commitment to customer service like that?

I Don’t Want to Be Your Friend (Today)

The biggest problem with all the social networks, as far as I can tell, is that there’s no easy and obvious way for me to differentiate the people to whom I am connected either by type of person or by how closely connected we are.

I have about 400 on Facebook and 600 on LinkedIn.  And I’m still adding ones as new people get on the two networks for the first time.  While it seems to people in the industry here that “everyone is on Facebook,” it’s not true yet.  Facebook is making its way slowly (in Geoffrey Moore terms) through Main Street.  Main Street is a big place.

But not all friends are created equal.  There are some where I’m happy to read their status updates or get invited to their events.  There are some where I’m happy if they see pictures of me.  But there are others where neither of these is the case.  Why can’t I let only those friends who I tag as “summer camp” see pictures of me that are tagged as being from summer camp?  Why can’t I only get event invitations from “close friends”?  Wouldn’t LinkedIn be better if it only allowed second and third degree connections to come from “strong” connections instead of “weak” ones?

It’s also hard to not accept a connection from someone you know.  Here’s a great example.  A guy to whom I have a very tenuous business connection (but a real one) friends me on Facebook.  I ignore him.  He does it again.  I ignore him again.  And a third time.  Finally, he emails me with some quasi-legitimate business purpose and asks why I’m ignoring him — he sees that I’m active on Facebook, so I *must* be ignoring him.  Sigh.  I make up some feeble excuse and go accept his connection.  Next thing I know, I’m getting an invitation from this guy for “International Hug a Jew Day,” followed by an onslaught of messages from everyone else in his address book in some kind of reply-to-all functionality.  Now, I’m a Jew, and I don’t mind a hug now and then, but this crap, I could do without. 

I mentioned this problem to a friend the other day who told me the problem was me.  “You just have too many friends.  I reject everyone who connects to me unless they’re a really, super close friend.”  Ok, fine, I am a connector, but I don’t need a web site to help me stay connected to the 13 people I talk to on the phone or see in person.  The beauty of social networks is to enable some level of communication with a much broader universe — including on some occasions people I don’t know at all.  That communication, and the occasional serendipity that accompanies it, goes away if I keep my circle of friends narrow.  In fact, I do discriminate at some level in terms of who I accept connections from.  I don’t accept them from people I truly don’t know, which isn’t a small number.  It’s amazing how many people try to connect to me who I have never met or maybe who picked up my business card somewhere.

The tools to handle this today are crude and only around the edges.  I can ignore people or block them, but that means I never get to see what they’re up to (and vice versa).  That eliminates the serendipity factor as well.  Facebook has some functionality to let me “see more from some people and less from others” — but it’s hard to find, it’s unclear how it works, and it’s incredibly difficult to use.  Sure, I can “never accept event invitations from this person,” or hide someone’s updates on home page, but those tools are clunky and reactive.

When are the folks at LinkedIn and Facebook going to solve this?  Feels like tagging, basic behavioral analysis, and checkboxes at point of “friending” aren’t exactly bleeding edge technologies any more.