Setting Up Shop With No Money.

To read the Green Pants Chronicles from the beginning, click here.

Act 2: Launch

Recap of the Inception Phase. No Axe Murderers.

Alright, so let’s recap… It’s fall of 2010. Brad and I had an idea that crapped out (BuzzBox), then circled around for the next one (RFMConnex). Adam Covati called me a coward, only in not so nice terms (don’t worry Covati, I’ve got nothin’ but love for ya baby), which forced me to confront the fact that I had to just jump if I was ever going to be an entrepreneur. Lovely wife, Laurie, supports me in the decision to recklessly throw myself into the abyss.

Scot met Brad while looking for an “in” at Bronto, they geeked out about the fact that RFMConnex was in theory close to what Scot and his former boss, Chris, did at LSSIData, just in a different industry, and that in contrast to Brad and I, may know how to actually build this thing out. We all had lunch at Ted’s Montana Grill at Southpoint, where Chris turned up the heat and grilled us cheesy sales guys more vigorously than the cooks were working the bison burgers in the back, but came to the conclusion that Brad and I were probably alright and the idea wasn’t half bad. We wrestled our way through the founder’s equity conversation (which I now call the “Hearts and Wallets” talk) and declared our corporate values, culminating in a family dinner to make sure that none of us or our children were axe-murderers.

Ask, the Worst They Can Say Is No

This next bit is one of my favorite parts of the entire journey because it speaks to the generosity of the human spirit, and the tendency of big hearted people to pull for those who are up against the odds. As “day zero” approached, I knew I was going to need a place for us to work. My boisterous and lovingly-lived-in (read “shoes all over the place and crumbs on the floor”) house wasn’t going to be conducive to the effort. So, I invoked a lesson that my [best ever, number one, one in a million] Mom, Carol Chelette, incessantly drilled into my brother, John, and I throughout our trajectories:

“Ask…. The worst they can say is “no.”

I just started asking everyone I could think of if they knew of free space. I got a bunch of “no’s” (which didn’t bother me at all), but within a few days, I’d generously been given two “yeses! “

Free Office Space

The first was Adam Klein who was working at the Durham Chamber of Commerce at the time, and who was passionate about stoking the fires of entrepreneurship in Durham. He was going to square away an empty cube or two for us in the Chambers offices, and I was so appreciative. The second was Michael Kerr of Edge Office. I’m not sure how I even got connected to Michael, but the net of it was that he had sublet the middle third of the 1st floor of the Penny Furniture building (owned/renovated by none other than the talented and ambitious Cynthia Hill), and was using it as his Downtown Durham showroom. It had internet, nice office furniture that could seat 6-8 people, a conference table…. The works! He met me at Beyu Caffe (whose founder/owner Dorian Bolden is now a good friend) and after chatting for a few moments, said that he had been involved in a few startups, knew what the grind was all about, and offered to let us use the space, and the furniture, and the electricity, and the internet…. For free. No strings attached.

Just Don’t be a D!&k

As he led me across the street to the office, I remember feeling a little dumbstruck, and in awe of this guy’s easy generosity. We’d just met. He didn’t know me from Adam. Well, not the Adam that I just mentioned. Nevermind, you know what I’m saying. He didn’t know me at all, and he was about to let me use the space for free.

As he gave me a key and showed me the security code, I asked… “do I need to sign anything?” to which he replied, “No, just don’t be a d!&k.”

I’m mostly good at not being a d!&k (although I’m sure Laurie would say I have my moments). So, I giggled a bit (not very cool) and confirmed that I could live up to that expectation, and away I went. Full office cubes, awesome rolling chairs, and the spottiest internet Frontier had to offer in Downtown Durham at the time. Beggars can’t be choosers.

(Not to get ahead of ourselves, but Michael had the sublease through early summer, and by then we were rocking and rolling, so we eased into a shared lease as we went through 2012, and in 2013 we took on most of the sublease but then let him continue to use our space. As we later moved into the American Underground in mid-late 2013, there was a competing furniture group that had everything locked up, but we insisted that Michael get the furniture contract for our space as we moved in, or we wouldn’t do the deal. Generosity begets loyalty. Michael took a chance on us when he didn’t need to, and helped propel us forward at a time that we had absolutely nothing, and for that I’m supremely thankful. If you’re reading this, and are in the Triangle, and need office furniture, please contact Michael and tell him that I sent you. Much love, friend.

Free Parking

So, the next thing was that we needed to park somewhere. While parking was significantly easier to find in Downtown Durham in 2011-2012, it wasn’t free, so the team and I scouted out all the little side streets and actually documented on our intranet where you could park your car all day for free within 2-3 blocks of the office. Those days are long gone, but it spoke to the hustle.

We were going to figure out how to launch this thing, and do it on the resources we had. It was the true definition of scrappiness.

Inception: Values. Family Dinner.

To read the Green Pants Chronicles from the beginning, click here.

Act 1: Inception

Values Matter

Before we all got on board, it was important to all of us, but perhaps most to Chris, that we express our values so that we knew what kind of people we were going to be together. I didn’t know it at the time, but we were laying a foundation for a very, very strong culture in this shared expression of what we thought was important.

Family Dinner

I’m sharing the values below, but before I do so, I’m going to capture one more very important event that happened before we all truly committed. Chris suggested that we all get together for a family dinner. This was a bit unexpected, but I like hosting, so… game on!

What transpired that night was that the four of us founders, and all of our families, got together at my house for a bit of a coverdish. (If I remember correctly, I think I made sliders). But the important thing that happened was that we got a few hours as families to interact and assess one another. Did the families and spouses interact in respectful and loving ways? Did the kids get along? Were we gracious to one another within our families, and in our interactions with each other?

It was an important lesson. A founder’s entire family is taking the risk. A founder’s family hears and sees the ups and downs that the founder is going through. Chris was right to make sure that we all meshed together well. And, we did.

Windsor Circle Values

Without further ado, here are the values that deeply defined us for almost a decade.

Mission Statement

Windsor Circle makes data-driven life-cycle automation simple, actionable and measurable for all marketers.


We are revolutionizing retail marketing by giving every retailer incredibly simple access to the rich data stored in the retail ecosystem. In doing so, we will build a world class software company employing 300 creative class professionals in Downtown Durham!

Principles / Guiding Thoughts


Openness and Transparency in All Cases.

Above all things, people want to trust one another. People are strong enough to handle the truth. We speak openly about things, and have the courage and conviction to trust one another with difficult topics. This is true regardless of who’s involved (employees, customers, investors, partners or others).

Facts, Not Claims.

Our communications, both as individuals, and as a company, should be rooted in fact. If you say it, be able to back it up.

Fairness Starts with Objective Data Points.

Do your research. Be open to others’ research. Trust each other not to skew or obscure the data.

Two Ears, One Mouth.

It is a human tendency to speak first. It is far better to “seek first to understand, then to be understood.”

Start by listening.

Single Source of the Truth.

We strive for a single source of the truth, and make sure everyone can get to it. At Windsor Circle, “truth” regarding our clients and our sales will reside in our CRM system. The “truth” regarding internal operations will reside on our Wiki (not floating around in email, etc). Everyone should dedicate themselves to communicating through these mechanisms so that everyone can get to the Truth quickly, and with confidence that we’re all singing from the same hymnbook.


All Employees are Shareholders.

The best way to achieve alignment between employees and their goal of maximizing value to shareholders is to make them shareholders. Everyone at Windsor Circle will have equity and/or options as part of their compensation plan.

Teams Survive Longer than Individuals.

A common team building exercise involves a hypothetical crash in the desert or in the arctic. You can only take 10 items as you try to survive. You do the exercise first as an individual. You do it again as a group. You then compare the results to those of survival experts, like Navy Seals, who theoretically could survive the best. The group almost always gets more items right than the individual. Lesson: teams survive longer than individuals.

Employees Grow the Business. Leaders Grow the Employees.

Both roles are accountable to excellence.

Lead from the Front.

Do what you expect your team to do.

Make Mistakes.

It’s ok to be wrong and it’s ok to make mistakes. Admit them, learn from them, and move on. People not making mistakes are either not taking enough risks, or they’re not admitting them, or both.

Dish the Ball.

Delegate responsibility and then get out of the way. Your teammates are as committed and capable as you.

Efficiency and Focus

Pareto’s Law rules.

80% of the value will come from 20% of the effort. Focus on the most important things and execute on them relentlessly.

The Goal of the Firm is to Maximize Profit for Shareholders.

Windsor Circle is not a non-profit. It’s not a social change agent. It is not a club. We are a for-profit entity. It is in our nature to be good corporate citizens, but while at work, we should be executing together with a single purpose in mind, and that is to maximize profit for the shareholders of Windsor Circle. And remember, all employees are shareholders.

The Paying Customer Dictates the Truth.

This is more than “the customer is always right.” This is an orientation, throughout our company, that we build products that people pay us for. If there is a question about what direction to take on a specific issue, ask what the paying customer thinks. That will be the answer.

Everyone is in Sales.

Those who think that sales is someone else’s job should find another job. Everyone should be asking, at all times, “What problem are you trying to solve?” If we can help, then we should forthrightly say so, and ask for an opportunity to explain why we think so and to seek the opportunity to win that business.

If You Can’t Measure It, Don’t Do It.

Things that cannot be measured cannot be improved. Things that cannot be improved are rarely worth doing.

The Art of the Possible

The “art of the possible” is a tremendous form of problem solving because it checks all of the “why nots” at the door. Focus on the desired result, name 100 ways to get there, and then choose the most viable option.

Don’t Think Outside the Box. Shred the Box.

It’s just business. The only rules (and they are of utmost and paramount importance) are honesty, integrity, and legality. If you can check those three boxes, you can and should break all other rules in the pursuit of maximizing profit. Question assumptions. Challenge the status quo.

Those Who Say It Can’t Be Done Should Not Get in the Way of Those Doing It.

The biggest accomplishments in human history are the ones that seemed impossible. But someone did them.

Ask. The Worst They Can Say Is “No.”

This is the execution part of “art of the possible.” When you think someone might turn something down, ask. Let them turn you down. On the off chance that they say “yes,” you will receive benefits that no one else thought possible.


No Substitute for Ownership and Fair Compensation.

Foosball and free sodas are poor substitutes for fair financial compensation and ownership in an exciting, growth-oriented business. Doesn’t mean that we won’t have fun. And we’ll very likely have free soda. But we won’t confuse the fact that our employees’ well-being, and that of their families, are of paramount importance to them. The nice-to-haves are just that. Nice to have.

Play to Your Stars.

Wow your top 10%. Excellence is hard to find. Once you’ve found it, secure it.

Risk * Execution^2 = Reward.

We’re building a world class software as a service company. As a startup, we need people taking risks. The more risk one takes, the more reward is embodied in the upside. That said, we must execute against our plans to mitigate the risks, or the reward will never materialize. So, risk times execution squared will be the lens we peer through as we think about financial compensation for members of our team.

Founder’s Equity. Hearts and Wallets.

To read the Green Pants Chronicles from the beginning, click here.

Act 1: Inception

This is a little out of order chronologically, and I think there may be some debate about how this all went down, but I’m going to write how I remember it, and if Brad, Chris, or Scot want to tell their version, I’ll post those, too.

Founder’s Equity

The net of it is that we were playing company again… Spending time on nights and weekends, and enjoying the feeling of entrepreneurship without the risks, but unfortunately without the progress and the focus either. Brad was still in the MBA program at UNC and interviewing for MBA-type jobs (including at GE… how corporate could you get!). Scot was consulting for Credit Suisse and had a good gig going, but was ready for a change. Chris was still at LSSiData, and getting paid well for a pretty low risk effort post acquisition. I had made the decision to leave my job though, so for me, the risk was about to get really real.

Brad and I had come up with some split for the purposes of incorporating as an LLC, but it was a placeholder until we could get something in place formally.

So, the question arose about sharing equity amongst the four founders, and we hit a bit of a chicken and egg problem. No one wanted to commit without knowing that they’d get equity. I didn’t think it was fair to assign equity without commitment to go full time in the venture. So, I built the simplest of cap charts in Google Sheets with 10% set aside for an eventual employee pool, and then 90% for the founders. And for the founders, I wrote 87%, 1%, 1%, 1% (see Chris’ note below) and then shared the spreadsheet. It met with the expected consternation from my fellow founders. “You can’t expect us to leave our jobs for 1%!”

Hearts and Wallets

I was happy to share, but I needed people to get in the game. I said “I have your hearts… I need your wallets, too. I need you to commit.”

So, we started having conversations about what was fair. I won’t share the specific numbers, but the levers that moved things around were:

  • Who had the original idea?
  • What kind of money where we leaving on the table by leaving our respective jobs?
  • What did market research give us in terms of norms that we could point to?
  • Who had the handsomest ears? (Me, clearly).

We also needed some startup capital. I put in $10k. Chris put in $10k. Scot put in $5k. Brad was in his second year of business school (ie, 2 years w/out income) and about to face a third. He didn’t specifically put money in, but he did get us into the UNC StartUp Challenge, where we won $7,500 (1st place, tech track). This all shifted the equity shares around a bit as well.

With everyone seeing a full view of the numbers, and no back-room dealing or obfuscation (extra points for the use of the word “obfuscation”), we had achieved our first full expression of a critical corporate value (Openness and Transparency), and we arrived at a set of numbers that felt fair (or at least fair enough) that we could all get on board for a year of no salary.

As I remember it, Scot committed first. Then Brad arranged it with his family. Chris worked it out with his wife. We had to make accomodations for Brad to finish out business school and spend all available time outside of it with Windsor Circle. Likewise, Chris had to finish out something at LSSiData, but in doing so, he was going to draw down his PTO and work nights and weekends.

Suddenly, we were sailing past our first milestone of team formation. We still had to formally commit it in legally, and technically, Chris, Brad and Scot had to formally turn in their notices, but we were now committed to each other, and honor and integrity were now in play.

Not Everyone Could Commit

There were actually a few more very capable people who wanted to join the founding team, and we wanted them there. But, as the day came when we needed the full commitment to jump in with both feet, not everyone could commit.

Some couldn’t convince a spouse to join. Some couldn’t quite get around whatever financial risk didn’t feel right (school loans, or mortgage payments, or healthcare, or whatever). I’m not demeaning that… in fact, I’m actively making a decision right now to join a team instead of starting my next company because I’m choosing some things in my personal life over my desire to start my next company.

Mark Suster calls it a time to learn, and a time to earn. The net of it is, that the stars have to align a bit. For some of the initial interest group, the stars didn’t quite align, and we had to keep moving forward without their contributions.

The next post will be about our values, which we committed in writing before formally committing as a team.

Chris’ Perspective on the Value of Openness and Transparency

I’m excited about incorporating the first of the memories and views from the outside in these posts. I asked the founding team to comment on this post before publishing it, and Chris shared this perspective:

I don’t actually remember [the 87%-1%-1%-1% splits to force the conversation], but I do remember the equity wasn’t at a point that I could commit to the risk and that we ultimately got there. The one thing that both encouraged me and surprised me was how open we had these conversations. All 4 of us knew what was happening for all 4 of us. That was a key not only for our relationships, but for the company surviving the ups and downs of a startup.

Rationalizing the Risk. Stop Worrying, Start Living. The $15k Deductible.

Act 1: Inception

To read the Green Pants Chronicles from the beginning, click here.

Stop Worrying and Start Living

Dale Carnegie has two books that achieved outsized recognition. The one that everyone knows is “How to Win Friends and Influence People” and I think it’s still wildly relevant even today. The other, perhaps less well-known tome is “How to Stop Worrying and Start Living.” I bring it up here because it was directly influential in how I rationalized the risk of leaving my job to start a company.

The basic gist of the book is that most of our worry comes from the unknown. All of the bad stuff that could happen to us starts swirling around in our minds, and as the permutations multiply exponentially, we find ourselves in a panic, unable to control all of the many terrible things that could come to pass. Carnegie simply provides a routine to get that stuff organized and then rationalize the worst case scenario.

Roughly speaking, it goes like this:

First, name one of the things that you are worried about…. Then, ask if it’s the worst outcome. Usually, your frightened mind says “no” and takes it down another level. So you name that one. So on, and so forth, until you realize the actual worst case.

And then you do two things:

  1. Recognize that it’s pretty unlikely, and,
  2. Work out what you’d do in that situation.

For me, it went like this:

Irrational Me: OMG, I’m leaving a high paying job with a successful company. What if I wreck our family’s financial situation and we end up destitute?

Rational Me:Ok, that’s not realistic. I’m a well known VP of Sales in the area. I could easily get a job as a VP again. Laurie is a well connected MSW. She could easily get a job as a social worker again.

Irrational Me: Yeah, but what if we can’t find jobs!

Rational Me: Ok…. If needed, I could start a regional or national job search and open up the opportunities.

Irrational Me: Yea, but what if I still can’t find anything!

Rational Me: Ok… well, that’s pretty unrealistic, but I’m not afraid of hard work, and I could always step back into being an individual contributor, and a skilled sales person can make a lot of money.

Irrational Me: Yeah, but what if you are too old, or too experienced, or too whatever and you can’t even get that job?

Rational Me: Ok… now this is getting silly…. But on the very low chance that I can’t find any job related to sales whatsoever, I’ve never been afraid of hard work. I ran a lawn service in high school. I could easily do manual labor to make ends meet.

Irrational Me: Ok, but what if it’s not enough money!

Rational Me: I’ve saved a bunch of money in my 401k and in my kid’s college funds. In the ultra-low-chance that all of this terrible chain of events did actually somehow occur, we could liquidate that until we get on our feet again.

Irrational Me: Yeah, but what if that runs out!

Rational Me: Dammit! This is silly! Ok, well, I have very little debt, I could use credit cards for awhile to cover my bets and dig out of the hole.

Irrational Me: What if you don’t! What if you go bankrupt and lost the house!

Rational Me: OMG. Won’t happen, but ok. Let’s say that happened. I’m very close with my brother, my mom, my step mom, my wife’s family, and my step-sisters. I also feel very fortunate to have several close friends. If the absolute most catastrophic things came to pass, someone among these many close connections would allow my family to move in for awhile until we got back on our feet.

Rational Me: And if that didn’t happen, Laurie ran a homeless shelter. We would at least know the ropes.

Rational Me: And if that didn’t happen, I camped for two months in my early twenties on a bit of a road trip. I know how to camp and could do that for awhile with my family if this absolute most terrible financial situation played out for us.

This seems like an infinitely silly exercise, but it mattered to me. I really did reconcile myself to the fact that no matter how bad it got, I wasn’t going to die, and I was pretty sure I wouldn’t lose my family. I could figure it out, no matter how far down this ladder of increasingly unlikely events I fell.

Which led me to a very freeing conclusion:

As long as I had my wife, my kids and my dog, everything else was gravy.

Walking around everyday thinking that everything you have above and beyond your immediate family is icing on the cake is a wildly liberating sensation.

It was going to be ok. This wasn’t going to be a risk of survival…. This was going to be a risk of comfort. We might not get to go on expensive vacations for awhile (and we didn’t). We might not have fancy cars (I drove a used Honda Civic for several years). We might drink boxed wine and eat a lot of beans instead of fancy dinners (yep, did that too). But it was all gravy. And we were going to be fine. And I was free.

Setting Milestones and Trying to Fail Fast

Another part of the rationalization was setting milestones that were weeks or months away, and being committed to shutting down the effort if we didn’t hit those milestones (or have a reasonable path to hitting them). The very first milestone was getting a team to commit to the journey with me. The next milestone was getting a prototype built. The next milestone was getting a single paying client to commit.

In my mind, those first milestones of team formation, incorporation and prototype had to be wrapped up by April, or we’d hang it up and I’d go back and get a “real” job. (Spoiler alert: We hit those milestones).

The $15,000 Deductible on the Catastrophic Insurance Plan

If there was one thing that crystalized the risk the most for me, it was the catastrophic insurance plan that my kids and I were on in those first months. We were pretty healthy as a family, and I needed to just get several months of attempting RFMConnex under my belt. Extending my COBRA insurance from Bronto was a scary amount of money, and joining Laurie’s plan at United Way wasn’t much better. I had money saved in my 401k and my credit cards had high limits and low balances. So I chose a plan with a $15,000 family deductible for Jack, Cora and me, with the assumption that if we were all in a wreck together that I had the money to cover that bet, and that these next months of no salary was all about day to day cash management.

So, we rolled the dice and it worked out (but, yeah… scary!).

Committing to Risk. Stop Being a Coward. Just Jump.

To read the Green Pants Chronicles from the beginning, click here.

Act 1: Inception

All You Do Is Talk. Stop Being a Coward.

At some level, I owe the entire entrepreneurial journey to friend and fellow entrepreneur Adam Covati. I’d worked with Adam and Eric Boggs at Bronto, and they’d decided to turn a URL shortener that Adam had built into a full fledged Social Media Management platform called Argyle Social (refer to #UNCArgyle… go Heels!), and they were living the dream. High growth, excited customers, venture capital, white-knuckled fear of the velocity they were traveling… the whole enchilada. I was so hungry to do what they were doing. (As an interesting aside, I said as much to them about joining their efforts, and they both thought I was kidding, so a follow up a conversation never happened. Ah, what might have been…).

At any rate, Scot Wingo had created a StartUp Showcase at the ChannelAdvisor Catalyst annual user conference, and Argyle Social was one of the young companies selected to showcase their solution. The conference was being hosted at the Washington Duke (pretty swanky, with a nice golf course), and Adam, Eric and I were enjoying a beer on the putting green just outside of the restaurant. I was headily discussing BuzzBox, RFMConnex and about six other ideas.

And then, Adam dropped a load of bricks on me. “Matt, you have a bunch of great ideas, but when are you going to actually quit your job and do something. Stop being a coward.” He actually used an unsavory word that I won’t repeat here, but man did it hit me hard. I laughed it off in the moment, but my head was reeling.

I’m Afraid That I’ll Wake Up One Day and Never Have Been More Than A VP for Someone Else

My wife Laurie will tell you that I’m one of the hardest and deepest sleepers around (don’t ask her about the snoring… sheesh). I’m out like a light the moment my head hits the pillow. But not this night. I tossed and turned, and finally she said “what’s going on?” I recounted the story for her, and then laying there in the darkness, said “I’m afraid I’m going to wake up one day when I’m 60, and never have done more than be a VP of Sales in someone else’s company.” There’s nothing wrong with that…. It’s just that I really, really wanted to be an entrepreneur, and unless I jumped in with both feet, I would always just be that guy with ideas.

Laurie, to her credit, whispered that if it was that important to me, that she’d go back to work so that I could quit my job and make a go at it. So that night, with Laurie’s support, I decided to leave the safety and security of Bronto and make a run at it.

At Some Point, You Have to Decide: Just Jump

I started this series with the goal of just capturing the story, and not boiling it down to platitudes. I’ll keep faith with that mission, but here’s something I learned that is probably worth passing along. There is some very finite point in every entrepreneur’s journey where there’s a seminal, terrifying, and wildly freeing moment in which you decide that you’re just going to jump, damn the consequences.

This was my moment. Laying on my back, in the darkness of the early morning hours, with my mind racing and my heart thumping…. I decided to just jump. It was different than planning, or contemplating, or considering. It felt like the same thing that happens when you jump off a cliff into the lake below… you fret, and think, and shuffle, and then suddenly, the moment of abandon hits you and off you go.

Actually Jumping

I don’t remember the exact timing, but having made the decision, I started to set my affairs in order to make this happen. I reframed our budget (which Laurie and I later called the year of boxed wine and beans and rice). I did an assessment of all things that would potentially throw me off. I set up every medical, dental and eye appointment I could think of so that I could square it all away while I was still insured (and “ensured” so to speak…. That if I discovered something, I’d be able to ride it out while I was still employed at Bronto). I’ll spare you the gory details, but let’s just say that if it could be poked, prodded, cleaned, updated, or examined, I had it done. I was all clear and ready to rock and roll.

In about mid-November, 2010, Chaz Felix (Bronto co-founder) and I went for a walk and talk (something that we did often and which I enjoyed doing with him) and I shared my decision to leave Bronto and start a company. He respected my need to try because he’d felt that call too, years before. With that conversation, I was committed. I would enter January 2010, recklessly unemployed, with a catastrophic insurance plan, no salary and no full commitments from my team to follow me off the cliff.

And I was as excited and free as I’d ever been in my professional career.

In my next post, I’m going to briefly discuss the rationalization of the risk, because it was an important part of the decision.

Finding Our Founding Team. Sales Schmoes and Geeks.

To read the Green Pants Chronicles from the beginning, click here.

Act 1: Inception

Finding the Founding Team

I wish that I could claim more than luck on this front, but ultimately, it was luck. Or divine providence. Or something. Here’s the story…

Brad and I were playing with the concept of RFMConnex (oof, what a bad name), but we were two business guys with coding skills roughly on par with our proficiency in ancient Sumarian… that is to say, that we couldn’t code a single line and needed help.

As it turned out, Scot Catlin was in the hunt for his next job, and was eyeing an open position at Bronto Software. Scot was connected to Brad McGinity through LinkedIn, and reached out for an informational interview and a possible reference. Brad was in UNC Kenan-Flagler’s Full Time MBA Program at the time, and while he couldn’t blindly refer someone he didn’t know, he was happy to get together for lunch and chat.

As they sat together, it became obvious that what Scot had done at LSSi was similar in concept. In that business, LSSi was aggregating directory information for the purpose of directory assistance and marketing. You know when you move and change addresses, how you get that little flood of mailers that says “welcome to the neighborhood, here’s 20% off of lawn care…” They were one of the leaders in maintaining that type of database.

So Brad shares the start up concept we’re working on with RFMConnex, and Scot says “wow, we should get my former boss Chris Humphres involved!” Excitedly, Brad and Scot set up a lunch for the meeting of the minds.

Ted’s Montana Grill – Sales Schmoes and Geeks

I’m not sure how we picked it, but it was decided that Ted’s Montana Grill at Southpoint Mall was where this epic meeting of the minds was to take place. As we all arrived, we assumed the positions… Sales Schmoes on one side, Geeks on the other. One side leaning forward and jabbering excitedly. The other side contemplating intently, with a subtle hint of cynical suspicion clouding their eyes.

It was the first time we’d met Chris. As anyone who knows Chris would attest, he’s a hard interviewer. Let’s just say that the collaborative, generous spirit that we know and love Chris for doesn’t shine through in a first meeting (unless you’re a rabid Crimson Tide fan, in which case you get fast tracked to pure love and devotion). Brad and I are both Tarheels, so we got pointed questions about RFMConnex that highlighted the inconsistencies in our logic, and clearly demonstrated our need for some engineering talent. In spite of the tough inspection, Chris said he liked the idea, but that he had something else brewing, and if it worked out that he’d be pursuing that with someone he already knew and trusted.

However… and this was a big moment…. If that didn’t work out, he might be interested in exploring further. Within a few weeks, the other thing didn’t work out, and RFMConnex suddenly became a real possibility for Chris and Scot.

Playing Company, Again

So, we were back to “playing company” again, but with a new idea and a new cast of characters. We met at my house a couple of Saturdays. We had a few other folks that had expressed interest engaged as well… so there was perhaps 5-7 of us poking around on this concept. Powerpoint slides started forming. Sketches of the first tech concepts started to come together.

But no one was on a payroll, no equity had been decided, no articles of incorporation formed. Just guys futzing around in their free time.

The next couple of posts will be important ones as they set up one of the most important early stage moments of commitment to “just jumping” and to defining the equity splits.

Moving Quickly to Next Idea: RFMConnex

To read the Green Pants Chronicles from the beginning, click here.

Act 1: Inception

“Call Me Back, I’ve Got the Next Idea.”

While history will not commemorate these words in the same way that it did with “Mr. Watson, come here…”, it was a seminal moment in our trajectory. We’d just killed the BuzzBox idea, and I pinged Brad back 5 minutes later with “call me back, I’ve got the next idea.”

The idea was to platform integrations between eCommerce systems and email marketing systems so that it was super simple to transform data into targeted marketing. I’d been exposed to the concept of Recency, Frequency, Monetization while in business school, commonly known as RFM modeling.  I knew packaged integrations would make the hard work of integrating platforms much, much simpler.  I knew that this would work.

Good Idea, Terrible Name

My working name for the idea was RFMConnex, which I’m a little horrified of today (did I really come up with a name that sucky?). We’ve taken a lot of good natured ribbing over the name Windsor Circle (which I’ll explain in a later post) but oh, man, was it better than RFMConnex.

Moving Quickly to the Next Idea

All kidding aside, this moment was critical to the journey for a non-obvious reason. After several months of work on BuzzBox, it would have been easy to just roll over and be done with it when we killed the idea. The drive to build something, however, was stronger than the idea itself, so moving from one idea to the next was important.

This played out later in our journey as well, because as we kept steering towards Product-Market-Fit, we had to keep morphing the idea, dropping what wasn’t working, and shifting towards what was working.

We didn’t realize it at the time, but the ability to let go was critical to moving forward. (Come to think of it, the writing of these Green Pants Chronicles is probably an act of letting go of the idea that has consumed me for the last 8 years).

BuzzBox. Killed by Truck Rolls. No More Playing Start Up.

To read the Green Pants Chronicles from the beginning, click here.

Act 1: Inception

BuzzBox – Our First Idea

The very first idea I played with had nothing to do with Windsor Circle. My thesis, in 2008-2009, was that smartphones were too expensive to gain wide adoption but that social media was taking over the world. I guess I was batting 500 on predictions. It was easier to believe then as the iPhone launched on June 29, 2007, and most of us considered ourselves lucky if we had a BlackBerry. WiFi was not ubiquitous, and 3G ruled the airwaves, and most of us had flip phones if we had anything more than a landline.

Simultaneously, pay phones were in steep decline and disappearing from the landscape, leaving in their wake millions (billions?) of dollars of hardwired infrastructure to every public place imaginable, from restaurants, to airports, to street corners. And no one was using that infrastructure!

So, the idea was to put an elegant touchscreen everywhere a payphone used to be. The user-friendly interface would be tied to social media sites, and allow users to post to Facebook or Twitter, or check email, or search for directions, in exchange for answering a few quick survey questions. This would allow brands and advertisers unparalleled first party research opportunities as demographic data based on location is well documented.

Killed by Truck Rolls

The net of it was the marketers loved the idea and VCs hated it. But the VCs didn’t hate the idea because of the cost of the hardware… we assumed that was going to be the issue. What killed the idea was the infamous “Truck Roll.” The hardware was a fixed cost, and one whose unit cost would come down with scale. However, every time a device went offline, or some drunk in a bar put her or his fist through a screen, we’d have to send a contracted service provider out to fix it. That scary, unknown, largely variable cost killed the concept. I spoke to some pretty high level RedBox management team members for perspective, but their footprint was less extensive that what I was imagining, and their units could be “hardened” in ways that didn’t limit the attractiveness of the user experience.

No More Playing Start Up

At the time, one of my most dynamic classmates from UNC Kenan-Flagler’s 2005 Full Time MBA program, Allison Philips, had joined up with Brad McGinity and me to investigate the idea. We were taking real steps to validate the concept (or invalidate it, as it turned out), but there was a point where the weight of the truck roll was looming large and we needed to make a decision about how to proceed as we were consuming valuable evening and weekend time as we were trying to figure it all out.

At the time (summer 2010), Chris Heivley and Dave Neal were underway with the Startup Factory at the American Underground, an accelerator and early stage investment fund. The call went out for applications for the next class of program participants. It would require me to quit my job, Brad to configure his second year of business school in a way that allowed him full time participation in our efforts, and Allison to move from DC to NC for at least the 12-week accelerator program. As I saw it, it’d be a good vehicle for forcing the conversation about whether or not we were serious about BuzzBox, as it would require real (and scary) life decisions.

As we explored the idea of filling out the application, the conversation had the intended consequence. We decided as a team to kill the idea, thinking that it did not have the right long term prospects to be worth the amount of sacrifice we were going to have to make. We were not ready to go from “Playing Startup” to committing, which in hindsight was a good thing.

“Call Me Back… I’ve Got the Next Idea!”

5 minutes later, I pinged Brad and said, “call me back… I’ve got the next idea!”

(Insert dramatic cliffhanger here so that you’ll come back and read the next post about how the idea that became Windsor Circle came to be!)

Introducing “The Green Pants Chronicles”

To read the Green Pants Chronicles from the beginning, click here.

False Bravado and Platitudes

The entrepreneurial journey is an exhilarating, terrifying, empowering, destructive and addictive experience. So often, what is written about these journeys falls into one of two categories… Platitudes and False Bravado.

The False Bravado is that annoying “we’re killing it” thing that many entrepreneurs feel trapped into saying anytime they are asked “how’s it going?” If 90% of startups fail, everyone is decidedly not “killing it.” The Platitudes are those distilled bits of wisdom that we all write to make it look like “we are killing it” or have already “killed it” and which tend to leave out situational variables, larger context, and dumb luck. I’m hoping to avoid these traps.

The Green Pants Chronicles

My hope in writing this series about my own entrepreneurial journey with Windsor Circle, which I’m dubbing “The Green Pants Chronicles” (after our team’s penchant for wearing said kelly green knickers) is to capture the experience in rough chronological order, and to do so with the Openness and Transparency that we valued so highly in our team. Some of the journey was amazing, and made us look like heroes. Some of it sucked, and at best showed that the stars don’t always align, and at worst, highlighted very human moments of not landing on the right strategy or execution soon enough to realize the rare air that Unicorns breathe. Above all things, I hope that these entries are real in their rendering of the 8 year journey.

My friend Christopher Gergen wisely counseled that I should capture the play in a series of acts (versus the time-based journal series I’d originally conceived). After some deep thought, I decided to frame it as such:

  1. Inception – How did the formation process happen?
  2. Launch – What did we do to actually get going?
  3. Validation + Early Growth – How did we set and pass through early milestones?
  4. High Growth – What did we do to pour fuel on the fire?
  5. Decision to Pivot – When did we start seeing issues and what did we do?
  6. Pivot – Once the decision was made, how did we push through this hard phase?
  7. Exit – As buyers looked at Windsor Circle, what did we do to exit?

I’m giving the decision and act of pivoting their own “chapters” because getting to the decision, and then making that decision and living with it, are very different things.

Two Caveats and An Admission

I’m going to write as openly as possible, with two caveats and an admission… First, I care about the people that were involved on the journey, and I’ll craft my entries in a way that respects everyone that was involved to the best of my ability. Secondly, there are things that require my continued confidentiality, and where those obligations exist, I’ll observe them.

As for an admission: Humans remember things based on perception, and those perceptions are obscured by time. I’m all too human. I’ll actively and openly incorporate feedback from the many people involved in the journey. In some places, that might be to modify my writing if I’ve just gotten something plain wrong. In others, it might be to capture and offer a differing perspective directly in the post so that numerous views and vantage points can be considered by the reader. Either way, I’m open to feedback and will incorporate it to the best of my ability.

I’m looking forward to capturing the journey on “paper” and reliving the wildest professional experience of my life… See you out there.

And, that’s a wrap!  Off to my next adventure…

What an amazing ride.

When Chris Humphres, Brad McGinity, Scot Catlin and I started Windsor Circle in 2011, we had a vision of democratizing data for online retailers.  We rocketed out of the gates with a pre-product, pre-revenue round, and scaled to 70+ people over the next several years, with fun team wins such as winning the prestigious Google Demo Day award, SxSW Pitch Competition, Best Place to Work in the Triangle, and an Inc. 500 Fastest Growing Company.

We took some punches, too, when we pivoted in 2017 to focus on the enterprise market, a hard strategic move that reduced our team by half, but ultimately proved successful as it led to a 2018 exit to OSG and a merger with its’ email marketing subsidiary, WhatCounts.

We were a hard-working, values-oriented, smart crew, with a penchant for Green Pants and funny mascots, and I am so proud of what this unique group of people achieved together.

All journeys eventually come to an end, and for me, it’s time for my next adventure.

Starting in September, I will join SalesPad, which is on a mission to radically transform distribution operations worldwide.  In my role as Chief Revenue Officer, I’ll be working with the team to strategically and tactically scale new and existing revenue streams for the business.  In doing so, I’ll be opening and staffing an RDU office, primarily in sales, account management and business development roles (so get those resumes ready… we’re looking for adventurers and buccaneers who are ready to get into the fight and have a blast as we grow the business together!).

To my beloved family, my fellow founders and cherished team, our investors and advisors, our customers and partners, to my new friends at OSG and WhatCounts, thank you.  It was an amazing journey that I am immensely proud of, and I feel privileged to have been on the quest with each of you.

ps – We are going to hold a Friday Sales Meeting Grand Finale in the near future, and name the next and final not-so-very-sacred order.  If you know what either of these things are, I look forward to seeing you there!  Stay tuned for more info!