Thoughts on the National Circles program, and our involvement in it.

The following email was a bit of free form thought processing that stemmed from a dinner conversation with friends about Windsor Circle’s pending commitment to participate in the National Circles program (being implemented locally by REAL Durham, of which Mel Williams is an active contributor).

It involves us making an 18 month, bi-weekly commitment to a single family.  It’s a big commitment.  Thoughts below….

———- Forwarded message ———-
From: Matt Williamson <>
Date: Thu, Jul 24, 2014 at 7:53 AM
Subject: National Circles program
To: ——

Friends -


This is the program that REAL Durham program we were discussing last night.

It’s based on the National Circles Program.
Last night’s conversation was helpful in processing the risk we’re taking as a for-profit entity considering a deep commitment to a family.  As I was reflecting, I thought I’d capture reactions, both positive and negative, as we’ve talked about this internally and externally.
  • Positive Reactions
    • It’s nice to see a company making a deeper commitment
    • It’s a good reflection of who the people in WC are as individuals, and who the company is as a group of individuals
    • This type of commitment is what makes Durham’s brand of entrepreneurship unique.
  • Negative Reactions
    • You might not get out of it what you think you will.
    • Companies may not be set up to deliver these sorts of services, and this could lead to some degree of failure for both the family and the company.
    • This was top down / mandated.  Is WC doing this b/c Matt wanted it done?
    • There’s only 4 people involved in the core group.  What about everyone else?
    • The great white knight…  you think you can ride in and be smart and make change without really knowing the people or the environment.  Lots of examples of this failing at a massive scale.
As I’ve contemplated this effort over the last few weeks, I’ve wrestled with:
  • Why are we doing this?  What attracted me / us to this (versus more standard corporate volunteerism, or volunteerism at all)
  • What are the risks of a for-profit entity doing this versus a non-profit?
  • What’s my role?
  • What do I hope to get out of this?
  • What value am I giving to the family, to the team, to the community, to my company?
I’ve observed, broadly, the following perceptions of businesses and business-types at or near the intersection of poverty issues and trying to address them.  These observations are informed not just in this effort, but also at the helm of various Habitat efforts over the past 20 years:
  • Companies don’t do enough
  • Greedy
  • Too focused on numbers, not focused enough on people
  • Companies / business people aren’t to be trusted
  • When engaged in community effort, company’s have ulterior motives (mostly around taking credit for doing good in a community, even if the good isn’t that impactful, and especially if that token effort is being used to distract from negative community impact driven by the company’s business practices).
I don’t have the answers to much of this.  They’re just observations, and probably skewed as I am one person, with one set of experiences, and I don’t always get it right (I usually don’t get it right).
So, maybe to attempt to answer one of my own questions….  Why are we doing this?  What attracted me to this?
I’m attracted to the National Circles program for two reasons.  
First, the model is showing quantifiable success in alleviating the conditions of poverty.  It’s early.  We’ll see if these numbers hold, but I can’t deny that I’m interested in programs that can show real progress.  And I care about my community, and the people in it, so I was attracted to the effort because it could make a difference in my community.
Second, I’m intrigued by the level of commitment and connection being implied here, and that no company to our knowledge has attempted this.  There’s nothing wrong with the team volunteering once a quarter (and we do).  But this is about getting involved with a family in our community…  in my community… every other week for 18 months.  Not painting walls…  Not picking up trash…  (we do that already and are happy to do it more)….  But opening ourselves to what may be some painful introspection about the disparities in our community.  Being vulnerable during the training to be told just sit there and listen…  that your family leader is going to be smarter/better/more capable than you are at directing what will make change in their lives and in their communities.  To risk becoming emotionally connected to others who live very different lives, and wrestling with what that may entail in our own lives.  To deal with the unpleasantness of being perceived as a person of privilege that is doing this for the wrong reasons (this one is particularly hard for me to digest).  And, maybe, if we risk that much commitment, a family in our community may make real progress in their own journey.  And, as this unfolds, we as allies to this family might make real progress in our journeys as well.
I don’t know where this will go.
I’ve been a bit surprised by some of the negative reactions to attempting this.  On the face of it, one would think that a group of people, organized for whatever reason, who wanted to help implement a program that is showing real success in other locales would be a good thing.  There’s something about the fact that our group of people happens to be organized as a company (versus a civic organization or a church group) that seems to make people uncomfortable.  Maybe it’s in the way that I’m presenting it.  Maybe there’s an inherent distrust of corporations (and perhaps well earned).  Maybe corporations can be good at creating opportunities for its individuals to do good work, but that they are inherently poorly suited to engaging in that work directly.  I don’t know.
All this said…  entrepreneurs take risks.  I think we’re going to give it a go.  It’ll be an interesting journey, with an uncertain outcome.  But I’m excited to be trying, and I’m pleased that the people in my company are the types that would even consider it.

The Weekly Planning Sheet

Years ago, I spent some real time digging into Stephen Covey’s 7 Habits of Highly Effective People.

In quick summary, his thesis is:

  • He studied a bunch of very successful people (not just financially, but those w/ high degrees of respect in their community and having accomplished interesting things but not at the sacrifice of their families and friends).
  • He tried to isolate what was similar in how these people lived their lives (hence the 7 habits, see below, copied from wiki).
  • In essence, these people think of their legacy, plan long term objectives that are in line w/ the legacy they want to leave, and then proactively take action against them.  He suggests a weekly planning framework to operationalize this thesis.

It’s been very effective for me personally.  I’m not a “Covey-head,” and won’t project that it works for everyone in all cases.  But I do know that most of the interesting accomplishments in my life have been because I was thinking about the person I wanted to be remembered as when it’s all said and done, what creative and fun life experiences I wanted to have to get me to that place, and then having a plan for taking action to drive me towards those goals.

My Most Recent Tracking Spreadsheet

Over my career, I’ve swayed back and forth between good usage of the methodology and not using it.  In this most recent return to the methodology, I built it Google Spreadsheets and discipline myself to spend time each week.  I’m not perfect at it, but it helps to keep things balanced when I do.

Here’s my sheet: 7 Habits Tracking Template


In case you’re curious….

7 Habits of Highly Effective People (taken from Wiki)

  • Habit 1: Be Proactive Take initiative in life by realizing that your decisions (and how they align with life’s principles) are the primary determining factor for effectiveness in your life. Take responsibility for your choices and the consequences that follow.
  • Habit 2: Begin with the End in Mind Self-discover and clarify your deeply important character values and life goals. Envision the ideal characteristics for each of your various roles and relationships in life.
  • Habit 3: Put First Things First A manager must manage his own person. Personally. And managers should implement activities that aim to reach the second habit. Covey says that rule two is the mental creation; rule three is the physical creation. Interdependence
  • Habit 4: Think Win-Win Genuinely strive for mutually beneficial solutions or agreements in your relationships. Value and respect people by understanding a “win” for all is ultimately a better long-term resolution than if only one person in the situation had got his way.
  • Habit 5: Seek First to Understand, Then to be Understood Use empathic listening to be genuinely influenced by a person, which compels them to reciprocate the listening and take an open mind to being influenced by you. This creates an atmosphere of caring, and positive problem solving.
  • Habit 6: Synergize Combine the strengths of people through positive teamwork, so as to achieve goals no one person could have done alone.
  • Habit 7: Sharpen the Saw Balance and renew your resources, energy, and health to create a sustainable, long-term, effective lifestyle. It primarily emphasizes exercise for physical renewal, prayer (meditation, yoga, etc.) and good reading for mental renewal. It also mentions service to society for spiritual renewal.


Should you work at a Start Up? (Cross post from Bessemer)


Note: This article, originally in Venturebeat and cross-posted on the Bessemer Venture Partner’s website was so spot on that I’m quoting it in it’s entirety.  

Source: Bessemer Venture Partners Blog



Should you work at a “start-up”?

January 2014

This article was originally published by Venturebeat

I recently made the switch from start-up to VC, joining BVP after three years as part of the team at Foursquare. Recently, people have been asking me a lot about my experience switching careers and what they should consider when thinking about transitioning into the start-up world. Over the course of these conversations, I’ve boiled it down to four questions that I think are worth asking yourself before taking that leap…

1) What is your definition of “start-up”? – The phrase “start-up” can be misleading, describing businesses in many different stages. Be honest with yourself about the level of risk you’re willing to take – do you want to join a company with traction, financial runway, and one that will give you the opportunity to learn from experienced people, or do you want to join an earlier stage company with more potential upside, but more uncertainty? Your experience will largely be based on the company’s size, financing history, and experience level of the people you will be working for and with. With just 20 colleagues and less than $2M in funding, Foursquare was a different company when I joined than the company that I left three years later with 170 employees and over $100M raised, but it was definitely a “start-up” throughout

2) Why do you want to work there? – If you’re thinking of joining a start-up because it sounds cool or your roommate is doing it – don’t. Make sure you think the company has great leadership and a product or service you can get behind. Sure, the offices will likely be a fun place to spend your days compared to your current corporate digs (and there might even be beer on tap), but things aren’t always easy when dealing with the ups and downs of an organization finding its way. Make sure you are excited to be in that space going forward, as you will likely be gaining expertise that will guide what you do next.

3) Are you ready to define your role? -  The earlier in the company’s life, the more you will have to dictate how you spend your time. Earlier stage start-ups have an endless number of things they could be doing. No matter what your role is, it will be largely up to you to prioritize your time and figure out how to add value. Nobody will be holding your hand or giving you constant feedback, so understand that is what you are signing up for.

4) Have you cut through the hype? - If you want to know how well a company is really doing, what it’s like to work there, and whether or not it’s a good fit for you, then you need to talk to current and former employees. One thing you learn quickly while working at a start-up is that there is often a massive disconnect between perception and reality. So get connected or introduced to people who know the real story.

At Foursquare, I was lucky enough to work with smart, passionate colleagues, experience rapid growth and the associated growing pains first hand, and witness fundamental product and strategic shifts. It was an amazing team to be a part of and the operating experience has served me well in my early days of working with entrepreneurs. If you can get comfortable with the answers to these questions, then go for it.

Foursquare team meeting, June 2010 (photo by Mari Sheibley)

- See more at:


The Culture Sandwich

We have an informal professional development thing going at Windsor Circle.  The group chooses a book, company buys copies for everyone that wants to participate, and then we meet for several weeks and discuss the book as we progress through the chapters.

In a recent conversation, we discussed at length how culture is set in an organization.

In most cases, the culture is set by the leaders.  If there’s apathy at the top, it will flow throughout.  If there’s a solid set of principles, well applied, that too will propagate.

But the thing that I found interesting was how the team at large receives and amplifies the culture.

Initially, the leaders set the culture at the top.

But then that culture gets codified into systems and practices.  At Windsor Circle, things like the quarterly team day and our Friday Sales Meetings are examples of things that codify the culture.  At this juncture, we’re still small enough that our team has regular interaction with our leaders.  The culture can be communicated directly.

As we scale, however, that culture will not be directly interpreted from my mouth.  As we scale to 100 people, or 300 people, or 1,000 people, the culture will actually come from the bottom up.  People will interpret the culture from the people around them, and the systems that support them.

In essence, you have people at the top setting culture, and people at the bottom setting culture…  and what lies in between is the true test of what a firm is made of.  A culture sandwich.

It reinforces how critical it is to document and constantly refer to one’s principles and then find ways to cement them in via routines, practices, and events so that large groups of people interpret and reinforce the culture in the same way.  Failing that will surely lead to a disjointed and apathetic organization.



5 Critical Components of Building A Winning Startup Team

This week I was invited to speak at an entrepreneur’s only lunch hosted by CED, on the topic of building winning teams in a startup environment.

The attached presentation highlights what I think of as 5 Critical Components of Building a Winning Startup Team.

CED Entrepreneur Series Nov 2013

  1. Founding Team – Share Equity and Play Fair
  2. Commander’s Intent – Capturing Vision, Mission and Principles
  3. Know Thyselves – Personality Profiles with Myers Briggs
  4. Be Big Now – Ruthlessly Repeating Who You Want to be Tomorrow, Today
  5. A Little Crazy is Good – Tapping into Creativity, Spontaneity, and Uniqueness

The presentation contains specific examples from our experience as a startup (although you’ll have to forgive a few greyed out areas to protect confidentiality).



The Power of Myers Briggs for Start Ups

We hold a quarterly team day to ensure that we are nourishing our most important asset…  our people.  In an entrepreneurial environment, it can be hard to come up with the resources (cash, expertise, time) to create meaningful exercises that dramatically accelerate a team’s ability to form and perform, beyond the stereotyped foosball table and free sodas.

Don’t get me wrong…  we have our Friday Sales Meeting (a weekly all-company happy hour where you have to pound your tasty beverage if you are caught talking about work) and we regularly get the team together for outings like the Thanksgiving Texas Hold’Em Smackdown or the July 4 “Grill ‘em.”   But these are social events, intended to be casual, easy, and free flowing.

At Windsor Circle, we actively engage each team member with a Myers Briggs Assessment and then spend 2-3 hours going through exercises to understand how various types of people interact, and how it applies to the people in our team as they express those personalities.


  • Human Metrics has a quick and free assessment here.
  • Typelogic has good descriptions of the various types here.
  • John Fahlberg, a retired Target executive, has coached us numerous times on this disciple.  If you’d like him to coach your team, visit his site, and tell him I sent you.


Just to get the juices flowing, I thought I’d summarize some of the comments and observations from our experience yesterday.

  • 100% Intuitive, 0% Sensing – This vector has to do with how people take in data.  Sensing types do a lot of research, and then shape their world around the existing data.  Sensing types seek “what is.”  Intuitive types engage high level concepts and patterns, placing high importance on imagination.  Intuitive types seek “what could be.”  It was fascinating to find that in our team, we were 100% “what could be.”  We theorized there was a selection bias here…  that the startup environment attracted those who loved the art of the possible, and that the risk and unknowns of the very early stage process might drive those who seek data and structure away.  It also made us think about next hires…   might be good to balance us out a bit!
  • “I hate being praised publicly” – One of our engineers, who has a strong expression of introversion, shared with me that he not only didn’t care about being praised publicly for doing well, that it actually made him uncomfortable.  A well meaning extravert (like me) might sing his praises in a team meeting, completely unaware that this is actually a painful experience.  What this specific team member expressed was that he was much, much more motivated by being given a thorny technical problem to solve and the time to solve it.  Unlocking his zeal and passion for Windsor Circle, therefore, is much more about planning and allocating tasks than it is remembering anniversaries or publicly praising him.
  • Brad’s Time of the Month and Carrie’s Internalization - My co-founder, who runs sales, holds responsibility for client renewals.  During our monthly billing cycle with clients, there are always a few that raise their hand to cancel their contracts (primarily for non-usage on the clients’ part).  And it drives Brad batty.  He wants our clients to be successful.  He wants Windsor Circle to be successful.  And when he processes a few calls / emails in one day (triggered by the billing) he gets grumpy.  Under stress, his personality type (ENFP) feels overextended and edges towards shutting down.  One of his team members, Carrie, has a high social component to her personality type (ENFJ), and therefore internalizes others’ stress.  They discovered that when Brad is in “his time of the month” that she also feels stress because she’s wondering what she has done wrong.  Knowing the pattern will help them operate more smoothly.
  • I Get Irritated by Those Who Won’t at Least Consider the Impossible – The book that we’re using details each personality type, and describes what irritates them and how they may irritate others.  Two strong traits of mine are that I am drawn to things that others haven’t done before, and that I deeply believe that they can be accomplished with enough vigor, passion, intelligence and hard work.  I have a very strong negative reaction to those who look for reasons why something won’t work instead of inventing innovative ways to actually pull it off.  In reading my personality type handout, I discovered that it’s a known phenomenon that us ENFPs get irritated “by those who won’t consider the impossible”.  And, interestingly, other personality types may become irritated by an overly optimistic and unrealistic approach to new projects that my personality type expresses in extreme situations.  The awareness of types is what’s important here..
  • I Need Time to Process – My co-founder and CTO, Chris, is a strong INTP.  He draws energy from having time to center, without distraction, and process things.  His predilection towards logical, data driven, non-emotional information gathering and decision making means that in times of high stress, he needs time to go process things.  My personality type in the same situation requires high degrees of social interaction and group brainstorming.  Both approaches are fine…  but under stress, operating without an understanding of what the other person needs is a recipe for conflict.  Here’s a post about a specific experience that started off hard but ended up bringing Chris and I even closer as co-founders.

We uncovered a lot of other interesting insights during our session.  I hung the resulting charts in the kitchen area so that our team will see where we landed, how we interact and perceive the world, and how to engage one another in ways that will help us out-compete those who are not specifically working to build their teams with the intentionality that we are.

I’m excited to be blessed with a team that works so well together and trusts each other with personal perceptions and sensitivities.  It was amazing to me how often a team member would speak not only about how their personality type may become irritated by others, but how often they named how they might irritate others.  That high trust is the hallmark of a good group of people who are pulling together to excel at a shared task and who are investing in each other.

Sales Compensation – Account Executive 1 – RDU / Southeast SaaS

Sales compensation is always tricky…  Most folks that haven’t “carried a bag” (vernacular for being in sales and carrying a quota) aren’t aware of the high risk, high reward nature of sales compensation plans.

We recently updated our comp plans and I thought I’d share the datapoints that I gathered.


The big concepts to focus on are:

  1. Quota - What is the rep responsible for bringing in to the company in new revenue?
  2. Base – What does the rep get for showing up?
  3. Variable – What commission do they earn for hitting quota?
  4. OTE – On Target Earnings – Easy…  this is simply base + variable.  This is also a confusing number since people who don’t live on a comp plan assume that this is what sales reps make.  They don’t.   A third of your reps will make or exceed quota.  Another third will bobble around it.  The last third will feel the heat and will move on or be moved on.  (Hence the high risk, high reward nature of sales compensation).
  5. Efficiency - This is a measure of what percent of new revenue you are paying out in quota to get the new revenue.


The averages we found for the Account Executive 1 role were:

  • $370k Quota
  • $42k Base + $37k Variable for $79k OTE
  • 22% Efficiency


  • Startups tended to have a higher risk reward scenario (lower baser, higher OTE)
  • Established firms tended to have a higher base, with a lower OTE (less risk, less reward)
  • Recruiters play to established firms (who can pay the commissions required for head hunting) and they reported in numbers that looked more like the established firms.


My google spreadsheet (link).


What are your thoughts on sales compensation plans?  If you’d like to offer additional data points to help flesh this out, I will add them anonymously.  Just reach out to me directly.