Category Archives: Entrepreneurs


It’s one of those things that make you cringe when you hear it in a meeting.

Each time.

You consider yourself a coach and want to pull the exec aside right
there and then when she/he does it more and more.

You want to explain how bad it sounds.  How it can inadvertently impugn perception and
reputation.  And ability to lead.

But the meeting goes on, business gets conducted, and it somehow gets
dropped into the “next time” conversation bucket.

But it’s a pretty big thing.

Sometimes it’s a nervous tic, like saying “like” or “you know”.

But it can do damage far worse than those words.

It’s when a CEO, CFO or other team leader talks about “I’ve
restructured…” or ” I’ve sold…” right in front of the team.

Or when a CFO talks about “my receivables” or “my expenses” in front
of the Board.

I can’t stand it.  It makes me crazy.

It sends a message that a leader really doesn’t want to convey.

head up ass

But it’s an easy trap to fall into.

When I’m getting to know a team while evaluating investment — and partnership — it sends an alarm.

It makes me want to keep probing and exploring in order to confirm or disprove my concerns about leadership style, partnering potential, ego. Maybe even character.

When mentoring a CEO, it can be one of the fundamental building blocks of professional development.

Most great entrepreneurs are, at their core, great and talented individual contributors.

Innovators, artists, and really smart people.

Then they become Founders, executives and managers with teams around them.

Teams they recruit and want to inspire, guide and retain.

It becomes time to “make the turn” and become leaders.

To not feel compelled to be the smartest and most valuable person in every room.

It’s not about themselves.  It’s about the team.  It’s about what they can build through collective success.

It’s about leading by example.  About creating an environment where team members feel
they play a big part in team success. And feel they are recognized.

Great teams are composed of special people.

People who look for the vision and passion of leaders who can pull them towards a beacon.

People who look to leadership that demonstrates public appreciation and support for their contributions.


It’s not hard to say.

And the alternatives are not what you want.

Burning Bridges

A bit of a warning here.  A rant follows.

I had an experience the other day with a young investor from another firm and it got me thinking.

More directly, it got me recalling time spent on the other side of the table, raising capital from Silicon Valley VCs during the height of the bubble in 1998.

It got me remembering why I had a dim view of most venture capitalists at the time.

You might have heard that things then were, well, comparatively pretty easy.  And they were.

Easy for teams like the ones I led to raise capital at outrageous valuations. With important technology, good market timing, a real business model, a great team and business traction, the sky was the limit.

It was easy for VCs to select opportunities to invest in from a deep inventory of disruptive opportunities.

It was easy for VCs to be self-absorbed in their success.

And to forget about their real purpose as VCs.

The real purpose of a VC is to help special people build special companies. To help create value for all shareholders.  To help teams to delight their customers. To help develop talent. To build effective, long-lasting partnerships which help entrepreneurs and the venture firm alike.   And to generate strong investment returns to Limited Partners.

Forgetting their real purpose made it easy for investors back then to confuse their part in a start-up’s success.

It was easy to demand teams to “get big quick” (I still hate that term) without thoughtful business guidance.  And it was easy to be super-arrogant.

Push, slash, burn, move up, move on.


This was true of some of the veteran investors who made their bones when the going was good.  Certainly not all.  But enough. They were not shy about telling and directing management — as opposed to coaching and partnering.

But it was also agonizingly true of many of the junior investors.  The ones who might have sat in the back of the board room.  The ones who hadn’t yet experienced success as an entrepreneur, operator nor investor.  Certainly not enough to substantiate the inflated sense of self  that was displayed.

Neither personal success nor failure gave their advice context. But they barked out opinions and directives in support of their agendas, nonetheless.

That was then.

As a board member years later, one thing that I pride myself is being grounded in the knowledge of how hard it is to do what the folks we invest in and partner with do for a living.

Creating, building, leading and developing is incredibly fun.

But it’s seldom “up and to the right”.

It’s hard to solve problems, to lead the way and build both exceptional value and team culture.

Lots of peaks and valleys to the journey. Lots of amplitude in the trend line of growth.

It’s hard to be an entrepreneur and a company’s leader.

I appreciate the fact that, more often than not, the people sitting across the table are simply smarter and more talented than I am. In fact, given my modest intellect, it’s a pretty easy grok for me.

The people across the table are visionaries, creators, artists and executors.

Investor partners who do our job correctly are coaches & mentors.  We impart street wisdom and a guiding voice to help others avoid the roadblocks we experienced.

We help them to replicate the principles & practices that enabled us to experience the successes we enjoyed. Whether as operators, board members and/or investors.

That shared philosophy is why I selected my Polaris partners years ago — first as an independent director — then as an investor.

Until that point, the thought of doing what I now do for a living as a second career was less than appealing to me.

Good investor partners are not on the playing field.  We don’t need to originate that many ideas nor dedicate years of blood, sweat and tears executing them. We don’t live every moment of the company’s life. We don’t need to be the smartest people in the room. The people we choose to invest in — many of them several times over — fill that role.

Over the years, I found that the most effective investors rarely are the smartest people in the room.  If they are, they’re likely in the wrong room.

Like the best operating leaders, their key competencies reside in helping to build teams, to catalyze goal-setting, to orchestrate the ideas and talents of others. But really good investor partners  “clear the brush” and create an environment which enables the success of the management team.  And they stay off the playing field unless invited on.

So…back to my recent experience.  This is not then — but now.

An inexperienced investor, one who’s experienced little success, who confused all of this.  He thought HE was the company.  HE was the reason why the company is on a roll. HE was calling the shots for the founder, CEO, management team and company.

Pretty big job. He obfuscates a level of insecurity with arrogance. And he’s lost the trust and confidence of his management team in the process.

He brought it all back to me. Kind of a good reminder, all in all. And just as repugnant an experience this time around.

Sometimes, when really special, incredibly-intelligent people consistently come to an investor asking for money, and then experience great progress, it’s easy to confuse one’s role.  It’s possible to feel more important than you really are.

Unless you have real purpose clear in your own mind.  And work with people who share those beliefs.

Otherwise, it’s hard to be an effective partner to folks — after you give them that money.

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When you don’t know that you don’t know, it’s a lot different than when you do know that you don’t know.  Knowledge is confidence.  And confidence lets you play fast.                                                             

                                                                                                                                                        – Bill Parcells


Reflecting on a work life lived in the world of SaaS, it’s compelling how the practices of Product Management, Performance Marketing and Sales have each evolved at a breakneck pace. And how they have become more and more alike in their foundation.

Like Triplets Separated at Birth.

We all know that tectonic trends in data science, predictive analytics and consumerization of IT all present huge opportunities for building the next generation of great software companies.

But each also brings a mandate for entrepreneurial teams to adopt and install data-driven, disciplined — almost scientific — operating cultures in product management, marketing, and sales — to a degree few imagined five short years ago.

This change of state has totally transformed how to look at strategy formation, executive management and daily activities alike in each of these functional areas of an emerging startup.

One of the earliest SaaS companies to “get it” was LogMeIn (Nasdaq: LOGM), where we were and early investor and where I served on the BoD.

In my mind, they were the pioneers and a reigning benchmark for Product, Marketing and Sales launching themselves together into the current generation.

@seanellis (LOGM VPM and now CEO of GrowthHackers/Qualaroo, after having built the growth engines of Dropbox, Lookout, Eventbrite and others),  @andrewfburton (SVP Product and now CEO of Logentries) and ex-SVP Sales Kevin Harrison were all on the same page in driving this manner of thought and practice. Each led by the unified vision of CEO Michael Simon.

Each functional team installed and drove a culture of using data to sample, test, measure and iterate.

And then to re-sample, re-measure, re-test and reiterate — to build user-elegant products, transform performance marketing to aggregate users, optimize funnel and accelerate conversion.  And to refine the link between data, experimentation and execution to drive a world-class, high velocity selling machine.

All incorporated a culture which embraced not just metrics, quant analysis and testing — but also the practice of treating customers —  users — as partners in learning how to rinse and repeat.

Growth Hacking before Growth Hacking.

I spend every day with SaaS companies.  Each is different, yet themes are consistent.

Each strives to strike the right harmony with its users in optimizing the Product/Market fit journey.

Each strives to drive the never-ending journey of experimenting, testing, projecting and tweaking the activity/metrics mix which creates the ultimate growth hacking recipe.

Each strives to experiment, test and adjust their self-service, inside sales and business development models in order to tailor interpretation of high velocity.

Some use predictive and guiding data science technology – like — to push the envelope towards acceleration.

I often hear some execs and investors claim that they have “the playbook” for Product/Performance Marketing/High Velocity Sales that applies universally to SaaS startups.

They are either misinformed, inexperienced, or misleading.  Hey, I’m being kind.

There is no “playbook”.  No one size that fits all.

But there are cultural and operational principles which form the foundation by which repeatability can be iterated and tested.

Product Management, Performance Marketing and New Age High Velocity selling models — and leadership — now have more in common that many would believe.

Building a culture and selecting teams which are driven to experiments, measurements, tests, analysis — a constant life cycle of iteration.  Using customers as their partners. A culture which recognizes the interdependencies of each of the three functions.

Building great growth and sales engines in line with the products being sold.  And the products coming down the runway.

The great companies – and their CEOs – “get it’ and recruit and select leaders and teams which share a common passion to use data, technology, customers and testing disciplines to hack their way to velocity, scale and greatness.

Selecting a new age Sales VP is to look for qualities not unlike a growth hacking Marketer or best-in-class Product Manager.

Product Management, Performance Marketing, High Velocity Sales.

Like Triplets Separated at Birth.

Lily Pads

Several times over the past several days I’ve been speaking with both entrepreneurs with whom I’m working, as well as those with whom I’m exploring.

Again and again, the subject of balancing opportunity and focus comes up:

  • How to establish a strong first market beachhead. And then to select and execute crisply on a second. And then a third.
  • How to prioritize introductions of products on a roadmap.
  • How to think about planned company acquisitions and the value of a target company’s product as it applies to our company’s core business, assets and values.
  • How to get started on the journey of ideation behind founding a company.

When my thoughts are asked about how to approach these decisions, the conversations — while about completely different subjects relating to companies at very different stages of development — invariably come back to a simple strategic principle I’ve followed for many years.

The Principle of Lily Pads.


What the what?

It’s a concept I’ve incorporated into my personal thinking and advice I’ve offered as an entrepreneur, operator, company leader and investor.

It’s a checkpoint I’ve used on myself in building my career and in building my company partnership portfolio.  And also in helping to build our firm’s technology investment team strategies.

It’s input I give again & again to talented founders, managers and investors:

  1. Aim to be truly competent — and be known for that competence.
  2. Realize real, measurable success in that area of competence.
  3. Weigh the value of adjacencies.
  4. Assess the value of leverage.
  5. Then — and only then — consider expansion to other areas of target focus.

Brilliant Old Schoolers like Geoffrey Moore and his market entry philosophy of “Bowling Pins”  touch upon my principle. Target one market, then the next adjacent one.  Rinse & repeat.

But the Principle of “Lily Pads” — maybe someone can quote me and call it a Law — that would be awesome :) — can be applied to company formation, career development, corporate development, growth hacking, striving for K-factor or Seeking Alpha.

Get established as the best in an area.  But critically — pick the next areas by virtue of not just opportunity — but also the adjacency of  skills, assets, success and reputation.  And the potential leverage of each.

  • Company founding: Is the founding vision broad enough to enable the balance of laser focus and future expansion?
  • M&A: Can the to-be acquired product(s) be sold to the same customers?  Economic Buyers? Through the same selling effort?
  • Product Roadmap prioritization: Beyond business plan benefits, does it leverage existing dev skills & resources? Go-to-Market readiness? Customer support inferences?
  • Career Development: Has one’s experience, body of work, reputation and advisory network yet enabled expansion to broader focus?

On & On.

A pretty simple Principle.  So, OK, maybe not on par with Bernoulli.  And, as potential Laws go, certainly below the pay grade of Metcalfe.

But one that cross-checks for me in my simple mind again & again.

Get really good.  Then think about the merits of the next leap.  Ensure probability of execution by making the leap short.  Drive long-term success by testing, sampling, measuring,  Attain repeatability.  And increase the speed of every leap that follows.

Simple is as simple does.

frog lily