My podcast with OnBoards is live, talking with Raza and Joe about the importance of adding independence, first-time directors, and diversity to startup boards, and how Bolster helps companies achieve that quickly and inexpensively.

I’m writing a lot about Boards at the moment on the Bolster blog. We’re compiling all of those posts into a couple of eBooks. Once all of that is done, I’ll put some digests up here on StartupCEO.com as well as make the eBooks available for download.

But the gist of it is that we are working hard to break the logjam of diversity on startup boards, and we’re starting to meet with some great success with our clients.

Like Fingernails on a Chalkboard

Anyone who worked in the Internet in the early days probably remembers all-too-vividly how silly things got near the end.  Even those who had nothing to do with the industry but who were alive at the time with an extra dollar or two to invest in the stock market probably has some conception of the massive roller coaster companies were on in those years.

The memories/images/perceptions all come crashing down in the latest chapter of Tom Evslin’s blook hackoff.com in a manner that reminds me of the sound of fingernails racing down a chalkboard.  You’ve heard it before, you can’t forget it, you squirm every time you hear it, but you can’t tear yourself away from it.

I think Chapter 9, Episode 6 and Episode 7 lay out every single stereotype of the Internet’s bad old days in two easy tales:

– The CEO who says “The main reason for this meeting is to figure out how to get the stock price up again”

– The blaming of the investment bankers for the bad business model

– The head of sales who doesn’t understand his vanishing pipeline and the CEO who turns a blind eye, sacrificing future sales to make the current quarter’s numbers

– The surprisingly shocking realization that adding 30 new people per quarter costs a lot of money

– The parade of the lawsuits, lawyers, and insurance policies

– The notion that all problems can be solved with a new product, which of course must be built immediately, but with a smaller engineering team

– The struggle about laying off staff and the comment that “you can’t cut your way to growth and greatness”

If you’ve haven’t tried the blook yet, you can start at the beginning with the daily episodes, on the web or by RSS, or you can download chapters in pdf format on the site.  It’s a great piece of daily brain candy.

The Party's Over?

American party politics have had a few major realignments over the 220 years since we adopted our Constitution.  I took a class on this in school, but that was a long time ago, and I'll never remember all the details.  What I do remember is that they're somewhat chaotic.  And that they typically take several election cycles to take root.

I think we're in the middle of one now.  Arlen Specter's decision to become a Democrat is a particularly poignant example of it, though the fact that something like only 25% of the country now identifies with the Republican party is another.  With Specter, it's not that he changed his ideology — it's that his party changed its ideology.  Whether or not you view his switch as a cynical attempt to keep his job is irrelevant.  He has been a Republican for his whole public life of more than 40 years with a fairly consistent point of view and is a very popular public servant with his constituency at large, and now he believes he can't win a primary voted in mainly by party activists against Republican opponents. 

Something I read today – either the Journal or Politico – had a quote from a Republican hardliner that is further signifying the realignment:

South Carolina Senator Jim DeMint and welcome Mr. Specter's defection as an ideological cleansing. "I would rather have 30 Republicans in the Senate who really believe in principles of limited government, free markets, free people, than to have 60 that don't have a set of beliefs."

That doesn't say much for the future of the GOP now, does it?  That said, I think prognostications of a permanent Democratic majority are unfounded. If I remember my history correctly, a realignment occurs when one party gets too powerful and too big — its opponents are the ones who realign as a check and balance.  Examples range from the Anti-Federalists becoming the original Republicans in the early 19th century, to the rise of the Whig and then Republican Party in the mid 19th century, to the Roosevelt era in the mid 20th century, to the Reagan Revolution in the late 20th century.  American politics are streaky.  Parties usually have a stranglehold on at least one branch of government for long periods of time, then a realignment shakes things up for a while, then control switches.  With the Whigs/Republicans, once they settled down with the election of Lincoln, for example, the party dominated the Presidency for 80 years, winning 6 consecutive presidential elections, 11 of 13, and 14 of 18 from Lincoln up through Franklin Roosevelt. 

I guess my point is that Republicans as we know them today may be doomed, but Democrats shouldn't spend too much time dancing on their grave.  Realignments won't take 20 years to kick in any more.  We move too quickly, information is too freely available, and public opinion is fickle.

What's the lesson here for a business?  It's all about competition.  Having a commanding market share is a great thing, but it's unusual for it to last.  Smaller competitors attack when you least expect it.  They attack in ways that you pooh-pooh based on your perspective of the world.  And they can often combine with other smaller players, whether through M&A or just alliances, in ways that challenge a leader's hegemony.  They redefine the market — or the market redefines them.

So be mindful of market realignment — whether you are CEO of the Democratic Party or CEO of you.com, Inc.  Don't focus on what people have bought from you in the past, or why.  Focus on what they'll be buying in the future, and why.

(This post also appeared on Bolster.com).

As we wrote in The Gig Economy Executive, the major societal trend to “gig,” or part-time/freelance work, has reached the C-Suite.  We created Bolster to help organize a talent marketplace out of what is mostly an informal economy today – one where VC- and PE-backed companies find trusted freelance executives and consultants from their networks.  

In that earlier blog post, we wrote about the different types of on-demand executive work that C-level executives engage in:  interim, fractional, mentor/coach/advisor, project-based consulting, and board roles.

As we’ve been building Bolster this year, we’ve come to appreciate that not only are there different types of gig economy roles…there are several different archetypes of gig economy executives, too.  While there is a clear common theme of the desire to do some form of freelance, or non-full-time work that cuts across the four types, they are very different in their stage of life and their needs.  These are our four main Member user personae, to use the language of Product Management.

First, there is the In Between Executive.  This is the original concept of our founding investors at High Alpha and Silicon Valley Bank that drove their interest in Bolster.  The In Between Executive is someone who is generally mid-career and used to working in full time C-level roles and is, for whatever reason, between jobs at the moment.  Maybe her company just got acquired and she is taking a break.  Maybe her company restructured her out of a job.  Maybe she needed or wanted to take a break from work for family or health reasons.  Maybe she was just ready to look for a new career challenge.  The In Between Executive is perfectly suited to any of the on-demand executive role types but is a particularly good fit for interim CXO, mentor/coach/advisor, and project-based consulting roles.

Second, there is the Career On-Demand Executive.  The Career On-Demand Executive is usually someone who has had many years of experience as a full-time executive and who is now looking for something more flexible, or who just enjoys more variety in his work.  One of the Career On-Demand Executives in the Bolster network I spoke with early on described her journey to me like this:  she was “between things” when a friend of hers who had moved to France and started a company asked her to come set up her HR Department and run it for 6 months while hiring full-time staff.  She took a month off, lived in Paris for 6 months, took another month off, then started to look for something else like that.  Ooh la la.  Sounds pretty good to me.  The Career On-Demand Executive is a particularly good fit for interim CXO, fractional CXO, and project-based consulting roles.

Next, there is the Not Retired Executive.  When I think of the Not Retired Executive, I think of my Dad, who was a successful technology entrepreneur for 30+ years.  Since he sold his company several years back, he has helped a number of startup CEOs do everything from raise money to build a sales and marketing plan, to manage supply chains.  Sometimes he gets paid in cash as a consultant, sometimes he gets equity as an Executive Chairman.  Sometimes he talks to younger entrepreneurs and helps them out “just because.”  The reality of the Not Retired Executive today, however, is that many people are “not retiring” younger and younger because they’ve made enough money to take a step back from hard-charging full-time jobs.  The Not Retired Executive is perfectly suited to any of the on-demand executive role types.  The ones who are later in their careers and closer to being actually retired are particularly good fits for mentor/coach/advisor and board roles.

Finally, there is the Side Hustle Seeker.  The Side Hustle Seeker is someone who is a full-time executive somewhere but who is looking for additional professional opportunities.  She may be an experienced CMO who is excited about mentoring up-and-coming marketing leaders via a local or industry-based professional organization.  She may be looking for chances to “pay it forward” because someone mentored her along the way, earlier in her career.  She may have accumulated enough experience and wisdom to be ready for her first board of directors seat.  Regardless, she’s someone who is a “high wattage” professional who wants to learn and grow herself by connecting with others outside her day-to-day role.  The Side Hustle Seeker is best matched with mentor/coach/advisor and board roles.

So, what kind of gig economy executive are you, and how can Bolster help you find the kind of work you’re looking for while providing you with tools and resources to simplify your life?  Join Bolster as a member to find out!

Wanted!  Comp Benchmark Participants

Return Path is looking to benchmark our compensation structure with those of peer companies.  We would like to organize a project where an independent consultant gathers and compiles the data from a group of 10-20 companies and shares the aggregated results with individual benchmarks back with participants (the data will be anonymous on a per-company basis). 

The data we’d need from participating companies (for all positions) is:  Title and summary of the job description; Base Salary; Bonus; and Location.

The criteria for "peer company" is one that is comparable in size (50-250 people), geography (not rural, at least some in NY/Chicago/SF/LA), and industry (anything tech/Internet/services).

We will act as the project manager.  Participating companies will mainly just have to provide the data.  The cost of the consultant will be approximately $1,000-2,000 per participating company.  This is a small fraction of what a similar study would cost from one of the big HR/benefits consultancies — and should be much more targeted and useful as well.

If you are interested in participating please email us at [email protected].  VCs out there — please circulate this to your CEOs and CFOs!

When a group of us had dinner back in May, Brad posted that it was remarkable that 4 of the 6 people had blogs. Then Amy started a blog, making it 5 of 6. Today, Mariquita and her friend Sharon launched their blog about wine, making it a clean sweep.

There is almost a complete dearth of blog information and commentary about wine. You can tell — the URL she was able to get on Typepad was wine.blogs.com! When Mariquita and I went looking into other wine blogs a couple months ago, all we found were one or two somewhat lame ones, one not updated since February, one not updated since April, none with interesting information that helps average people learn more about how to buy, pair, and enjoy wine.

I think this will be a fun single-topic blog. Enjoy the first posting, and welcome to the blog world, Mariquita and Sharon!

The Good, The Board, and The Ugly, Part III

To recap other postings in this series:  my original, Brad Feld’s, Fred Wilson’s first, Fred’s second, Tom Evslin’s, and my lighter-note follow-up.

So speaking of lighter-note takes on this topic, Lary Lazard, Tom Evslin’s fictional CEO who ran Hackoff.com, now has his own tips for effective board management.  You have to read them yourself here, but I think my favorite one is #3, which starts off:

Never number the pages of what you are presenting.  Lots of time can be used constructively figuring out what page everybody is on.

Enjoy.

• terrygold.com: Hiring Salespeople
  Good posting from Terry Gold of Gold Systems on his experiences over the years hiring and ramping up a sales team.
  (tags: Entrepreneur Sales Management)

(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.

In From the Perimeter

I’m at the Direct Marketing Association’s annual massive trade show (DMA*05) in Atlanta.  While there are lots of things to potentially blog about, I think the most interesting one is the simplest.  When I started attending the DMA’s shows six years ago, the only interactive marketeing companies who exhibited were email vendors and the occasional sweepstakes company — and any interactive marketing company who did bother to show up was relegated to a small booth space in a corner of the trade show floor, away from the real action.  A friend of mine once told me it was easy for him to hit all the email guys at DMA — just walk around the perimeter of the room.

It’s 2005, and oh how things have changed.  The DMA put the “Interactive Marketing Pavilion” center stage this year, literally in the middle of the floor.  Besides Return Path, loads of other interactive marketing companies (and not just the email and sweeps guys!) have prime real estate at the show.  Within eyeshot of our booth are fellow email companies SilverPop, StrongMail, WhatCounts, Accucast, and ExactTarget, as well as analytics companies like Omniture, online ad companies like Blue Lithium, Kanoodle, and Advertising.com, lead gen companies like Cool Savings, and even a search firm or two.

The move is more than symbolic and more than just the fact that online marketing vendors have been around long enough to bid on better booth locations (although no doubt both of those things are true).  It’s representative of the way mainstream marketers now conduct business — increasingly online and increasingly multi-channel.  Online is another important part of the mix, not the stepchild.

Online marketing firms are now in from the perimeter, and we are happy to be here!

Mail Fusion

For 8 or 9 years now, we haven’t received a single bill by U.S. mail.  We use PayTrust (originally PayMyBills.com) for “online” bill pay.  We have a P.O. Box somewhere in South Dakota that we’ve redirected all our bills to.  The bills get opened, scanned, we get an email, we enter in a payment amount and date.  No fuss, no muss.  PayTrust even figures out which bills can be electronically delivered and provides an easy interface to set that up directly into the PayTrust account as well.  I haven’t received a bill or written a check in years.  I think we pay something like $9/month for the service.

I just ran across a new service this week called Earth Class Mail (thanks to my colleague Alex Rubin for pointing this out) that does the same thing for ALL of your snail mail, with a twist.  You direct all your mail (presumably not magazines) to a P.O. Box, and they first scan in all the envelopes.  You see them and decide what to do with each item — forward to you, scan in and show you online or via pdf, recycle, shred, etc.  The cost seems to range from $10-60/month depending on volume.

Certainly a good idea, at least for people who travel a lot or people who have to pay for a P.O. Box anyway (not sure it’s for everyone), and another interesting service where email takes center stage as the mission critical delivery vehicle.