Let me start right out by saying that I never finished college.

In fact, I dropped out of more schools than a person typically applies to. A friend of mine once said that I got my MBA “on the streets,” which is a nice way of saying that when I've seen an opportunity, I've gone for it and learned by doing and through hands-on experience. Even if doing so took me off of the prescribed path.

And along the way, I've likely learned more about how business (and the world) really works than I ever would have in the classroom.

🏢 Work

I’d love to say that I had a plan - I really would - but the truth is, I just sort of went for it.

Looking back, it's clear that my entire career has been nothing if not some combination of luck, hustle, opportunism, timing, and a near frenetic changing of mind and continual re-shaping of what I love and believe.

I’ve always led with heart and gut, making the decisions that felt right in the moment, and unrelentingly charging towards the things I felt would make me (and those around me) better, faster, and stronger.

Luckily, it's all worked out fairly well. I've had the opportunity to work in-house at major brands, build venture-backed startups, lead a strategy team for a major ad agency, and even start my own creative shop. This totally scattered and wonderfully circuitous route has left me with a pretty unique cross-section of experiences and skills, that make me as close to being one of those mythical full-stack marketers as anyone out there.

GreenZebras
Customer Service Advocate -  2000 to 2001

I hit the tail end of the dot-com bubble, but man did I land at a wonderful representation of the moment - a place called GreenZebras.

With big funding and a bunch of founders from MIT, the idea was to sell landscape equipment (think tractors and shovels) to landscape professionals over the web, in 2000.

Housed in an incubator company, complete with Aeron chairs, big team outings, and the total opposite of product/market fit, the company went bust about as quickly as you'd think it would, and we were all laid off right after the winter holiday.

I'd link to something that proves the company was real, but it's literally as if all evidence of its existence has vanished from the web.

Green2Go
Production Artist -  2001

With the market imploded and unemployment checks coming in, I did what most 22-year-olds would have probably done and just sort of hung out for a while.

A few months later, a former colleague reached out and asked if I'd be interested in doing some rather repetitive image reformatting for Green2Go, the company that had somehow ended up with the remnants of the now-collapsed GreenZebras.

My job was to essentially mask and resize product images (pulled from manufacturer websites), so they would be uniform and easily dropped into the product catalog on the Green2Go website. It was something a Photoshop action could do fairly easily, and they paid me per image.

Green2Go didn't last very long, either.

Focalex
Sales Operations - 2001 to 2004

After getting my fill of the volatility that came with the new economy, I decided to start looking for something a bit more stable but in the same general online space.

I can't recall the exact title of the job listing, but I applied for a position at a small email marketing company just outside of Boston called Focalex. My role would be to set up and deploy large-scale email campaigns, sent to Focalex's email marketing lists, on behalf of clients like Cingular, Royal Caribbean, and others.

I didn't realize it then, but I was about to enter one of the most transformative periods of my professional life. The perfect combination of atmosphere, work, people, timing, and my desire to absorb everything around me, allowed me to grow enormously and set me up for what would become a career in the digital space.

Part of this growth meant expanding beyond my core email-sending responsibilities and saying "yes" to almost anything that floated my way. As Focalex continued to add new people and products, I continued to take on more and more, ultimately becoming a utility sales operations guy of sorts, acting as the main link between the technical and non-technical teams, and ensuring everything behind the scenes, went smoothly.

And though I wasn't a formal part of the front-facing sales team, I was embedded enough within the group that I began to interface more and more with our external affiliates and partners, allowing me to develop some core client relations skills that I still rely on today.

Intermix Media
Ad Product Development - 2004 to 2005

In late 2004, Focalex was acquired by Intermix Media, a Los Angeles-based company in the same general space (affiliate marketing) we were. While the name Intermix Media may not ring many bells, one of their sub-brands probably does.

It was around this time that, in a far-flung corner of the Intermix offices, a few guys were messing around with an idea for a social network called MySpace. I remember distinctly being out in Culver City, meeting Tom and the team (maybe 15 deep at the time), and getting a black MySpace t-shirt that I still have - and wear - with pride.

But while MySpace was taking off, back in Boston, it was becoming clear that our ad product team was somewhat of a forgotten appendage, left to do the unsexy (and increasingly irrelevant) work that no one else wanted to deal with. Specifically, my role had become to help integrate the Focalex ad products into the massive network of Intermix web properties. As you can imagine, it was a lot of cross-country conference calls, systems that didn't play nice together, and plenty of political wrangling over who owned what.

And to top it off, now being part of a publicly traded internet company meant that we were bogged down constantly with Sarbanes-Oxley and CAN-SPAM compliance exercises.

But everyone just sort of hung on and dealt with it because the MySpace rocket was propelling us, and we all wanted to see where it would go.

Fox Interactive Media
Business Development Manager - 2005 to 2006

It turns out that the MySpace rocket went straight to Rupert Murdoch and News Corp in what was, at the time, a somewhat controversial acquisition. We were now part of a newly formed business unit at News Corp called Fox Interactive Media, which was to be anchored by MySpace, and filled out with a mish-mash of other online properties that News Corp was acquiring for eye-popping amounts.

Once the dust settled, it was back to business as usual. And business as usual for me in the new regime was a role as a Business Development Manager. Specifically, this meant selling what remained of our affiliate ad products to legacy publishing partners on a revenue share basis. A role and product set that did not fit AT ALL into the master Fox Interactive plan. Within weeks of the acquisition, it became pretty evident that News Corp would soon be putting any Intermix assets, not called "MySpace", onto the chopping block.

So after being part of three companies and two acquisitions in the span of just ten months, I decided to be proactive and make a change.

Prospectiv
Marketing Manager -  2006

For me (as well as a few others), the road from a crumbling Focalex/Intermix/Fox Interactive Media, led directly up Route 93 north to Prospectiv Direct.

Prospectiv was home to Eversave.com, and a suite of products (affiliate, rev-share ad products) that were near perfectly aligned with the types of things I had been working on for the past few years. In fact, at the time, there were maybe four or five companies in the entire country doing this particular brand of affiliate marketing, so the fact that Prospectiv was just 15 minutes away (the other companies were out of state), made this move feel almost preordained.

My job as Marketing Manager at Prospectiv Direct was, as the name suggests, direct. I was to sell in CPA and co-registration offers to publisher partners on a rev-share basis, and I got a salary plus commission based on my rate of success.

For years I had played within the sales department while deftly avoiding being a proper "sales guy", but now, despite the "Marketing Manager" title, I was a sales guy. I was cold calling, tracking my numbers, and really feeling it when I'd make or miss my goals. It sucked.

And compounding the general suckiness of being a sales guy, I was continually dealing with ding-dong web publishers who were getting rich from the ad products I was pushing. While I was busting my ass chasing small commissions, the guys on the other end of the conversation were making hacky coupon and sweepstakes websites, arbitraging traffic, and raking in six figures a month, while only "working" two hours a day.

Clearly, I was on the wrong side of this equation.

Around the same time, my friend (and former Focalex CEO) Seth was returning from some time off after selling his company and looking for his next venture. Over a few dinners, we talked about these arbitrage websites, how the model worked, what the numbers looked like, and where we thought the opportunity was.

It didn't take long before we decided to go for it. I'd leave Prospectiv, Seth would fund the move, and we'd set up shop as a publisher.

Pangea Media
Director of Business Development - 2006 to 2010

I distinctly remember day one of Pangea Media. Sitting in a Finnish coffee shop in Jamaica Plain (called "Sweet Finnish"), Seth and I looked over our laptops, kind of starting from a blank page.

Sketching assumptions and estimates over drinks was one thing, but turning those assumptions and estimates into a functioning and profitable company, was another.

We decided to start in the sweepstakes game and set up a really simple website called AtomicRewards.com. We plugged in some of the rev-share ad products I had previously been selling, and we turned live some modest search buys to get the traffic flowing.

The idea was simple - make money in the spread. Spend $1 on getting a user to enter our sweepstakes, then try to squeeze out $1.50 in revenue via a series of co-registration ads along the way - scaling what worked and pivoting away from what didn't.

Things initially moved pretty slowly - a few hundred dollars here and there as we got our feet steady. But the whole system was pretty automated (by design), and didn't take much in the way of hands-on man-hours. So while AtomicRewards.com was ramping up, we looked to diversify and test out other products.

Having convinced a developer friend (also from Focalex) to come join us as employee number three, we now had full-time engineering talent at our disposal. We dedicated this resource to building out a community-based quiz/survey/polling website called Quibblo.com. The idea here (again, a really broad sketch idea) was to build a better lead-generation mousetrap. Our entire company was based on the premise that we could buy cheap traffic and turn it into valuable leads for advertisers. And our working theory was that quizzes would be a great way to grease the skids and get more people to willingly fill out forms and provide information that we could, in turn, sell to advertisers.

While this theory ultimately turned out to be right in a big way, we didn't have our "ah-ha" moment for some time. Quibblo began attracting users from day one, all of them more than willing to fill out nearly anything we put in front of them. Unfortunately, these users were all teens, thus worthless to us and our model. We had lots of traffic and no one that could buy it.

It wasn't until we combined the sweepstakes and quiz mechanics in a more deliberate way that things really took off.

Our next product, QuizRocket, combined the best (or the worst?) of both platforms. We used quizzes as the entry point, driving super cheap traffic on hundreds of topics into our platform, and then ran users through a gauntlet of co-registrations ads while holding their quiz results hostage.

We had figured out how to buy traffic for $0.40 and sell it out the other end nearly instantaneously for $1.00. And we had figured out how to do it 100,000 times a day.

Pangea Media had exploded.

It was nuts. Back when Alexa rankings were a thing, QuizRocket held steadily at #40, right between Major League Baseball and Bank of America. We were launching new sites weekly, we were spending nearly seven figures per month on media, and doing it all with a skeleton staff of about 15 people.

My role as Director of Ad Operations was a bit of a catch-all, but my main focus was on the revenue side of the business. While my great friend Adam ran the media buys, I acted as the other side of that coin, ensuring that we covered (plus a margin) the cost of whatever traffic he was sending in. We created and fine-tuned ad products daily, day-traded with partners and offers in our registration flow, and worked with silly amounts of traffic and money.

But as quickly as our empire rose, it fell.

Because arbitrage games like these are an indefensible business, our would-be competitors could see too easily from the outside just what we were doing and how we were doing it. And it wasn't long before the space was jammed with other players, creating a bubble in the market. A glut of traffic buyers caused previously low user acquisition costs to spike while our ability to monetize those users stayed flat or even dipped. One day we'd make $100,000, and the next day we'd lose $40,000.

It was time to get out of this space and pivot the company towards something that would provide deeper and more lasting value. The timing was right for me to move on, and shortly thereafter, Seth ended up selling off this part of the business and re-launching a new product suite called SnapApp.

The Boston Beer Company (Samuel Adams)
Online Marketing Manager - 2010 to 2011

My friend Sharon initially tipped me off to this opportunity, and I immediately knew that this was what I wanted to do next.

Sam Adams was looking to make its first and only digital hire in the company's nearly 30-year history - and as I read it, this was the perfect role for me. It was a chance to leverage my jack-of-all-trades background to help create the digital practice for a brand that I'd genuinely and wholeheartedly loved for years as a consumer. This person needed to be a Swiss army knife of marketing with an entrepreneurial approach. This person wouldn't lead a team; this person would BE the team. It was a unique role that would require a unique person. And that person was me.

Unfortunately, the in-house recruiter disagreed, and after our first phone call, I received a polite but direct email thanking me for my interest and letting me know that she "didn't see a fit".

They were looking for a Harvard MBA type with a deep brand background and an academic approach. Someone who was well-studied in the science of Marketing (with a capital "M") and looked good in a blue button-down and a pair of khakis.

In other words, they were looking for the opposite of me.

But I wasn't going to walk away so easily. I knew the recruiter was wrong. I knew I was the right person for the role and intended to get it.

Having emailed with the recruiter, I knew the corporate email syntax, so the next step was to hit LinkedIn and figure out the person that this role would ultimately report to and contact them directly with a pitch on why I was the man for this position, which is precisely what I did.

Six weeks later, I began my role as Online Marketing Manager for Sam Adams.

My initial instincts regarding the type of person required for this job were dead on. No two days were alike, and I had my hands on every aspect of every digital channel in the brand's arsenal. For instance, managing the monthly email newsletter meant choosing the content, writing the copy, coding the templates by hand, helping with the graphics and design, managing the lists and software, deploying, tracking, and troubleshooting anything that may go wrong along the way.

This was a down-and-dirty, in-the-trenches, get-shit-done sort of role, and it was awesome.

Essentially anything that lived on a screen (outside of television) was my domain. And anything in my domain required a fully hands-on approach, tip to tail. Generating content, managing social media channels, copywriting, video strategy, website development, mobile experimentation, email program management, paid digital media, event support...even light graphics and HTML work were all standard on any given day.

I wasn’t looking for a change when I met Mike Proulx at a Radian6 conference one afternoon, not far from the Sam Adams offices. And I certainly wasn't looking to work at an ad agency. But Mike is persistent, and in his words, he began "courting me".

Over the next several weeks, Mike and I met up, maybe four times, to broadly discuss his team at Hill Holliday, and how I may fit into the group. After each of the first three meetings, I politely declined the opportunity. I was happy where I was, and there was still lots to be done at Sam Adams.

But as I said, Mike is persistent. In what would be our last coffee meeting, Mike persuaded me to "just come in and meet some people" which I agreed to do, and then he made me an offer that I couldn't say no to.

Hill Holliday
Vice President, Social Media Strategy - 2011 to 2013

Before joining Hill Holliday, the total of my time spent in ad agencies (all time) was maybe three hours.

I remember being shown to my office on day one, which was totally barren save for a phone and a laptop. I suddenly realized that when you get hired at the Vice President level, there's probably an expectation that you know what to do and that'll you just jump right in and start doing it.

I had no idea what I was doing or where to begin, and it was fairly terrifying.

But once again, this total blind lack of experience served me well. I wasn't held back by any past agency baggage, I had no bad habits, and I wasn't yet covered in that jaded and grisled exterior that comes after a few years served inside most ad agencies.

My precise role was Vice President, Digital Strategy, and I was initially allocated across five brands - Liberty Mutual, Safeco, TJMaxx/Marshalls, MLB, and Great Wolf Lodge. While the client variety was both intellectually stimulating and fun, the stress levels were insane when all five clients needed something at once, which happened fairly frequently.

To preserve my sanity, we pared back the workload, allowing me to give better focus to a smaller client set. One of the brands that I was immediately able to give more attention to, was Liberty Mutual. While spending rather heavily for years on television, outdoor, and digital display, Liberty Mutual had just begun exploring social media. Both the client-side social media team and the agency team meant to serve them were small. As were the budgets and the programs.

And while the combination of insurance and social media didn't sound all that sexy at first blush, it turned out that there was a lot of interesting stuff below the surface that we could work with.

There were thousands of local agents across the country that we could activate on social, we had traditionally offline referral behavior that we could try and replicate digitally, we had a chance to make boring insurance content interesting, and most of all, we had the chance to leverage amazing advancements in social media ad products as a means to drive hardcore customer acquisition for the brand.

We did all of this and then some. In just 18 months, we brought social media to the center of the brand's marketing efforts, growing the team by 3x and the social media budgets by nearly 10x. All the while holding social media accountable for driving the business and having a measurable impact on the bottom line.

As the Liberty Mutual business matured and hit its stride, I took on more varied client work again. I was able to participate in several new business pitches, including wins like Puma, Cadillac, Merrell, Liberty Mutual (incremental work), and Crabbie's Alcoholic Ginger Beer.

But outside of new business (where roles are a bit more fluid), I found myself feeling somewhat confined - departmentally tethered to just doing social media. I wanted more leeway to explore the ideas and concepts most interested me. The things that didn't fit neatly into any one department. The things that were part content, part social, part technology, part media, part creative, but weren't owned by any one group.

I was desperate to shed the social media title as a means to break out of the typecast and do bigger things. So I found a home in a seedling of a group we were calling "Experience Planning".

Hill Holliday
Vice President, Experience Planning - 2013

Agencies continually struggle with what to call things. On the one hand, they need to be on-trend, or even better, ahead of the trend, keeping pace with what's next and positioning themselves as future-forward. On the other hand, they need to name roles and departments in ways that make it easy for clients to buy their services.

Clients know how to buy "social media" and are willing to pay for it. Clients don't know how to buy "Experience Planning," and they aren't sure they're willing to pay for it.

So I knew that my pushing for a title change could theoretically make it more difficult for me to be consistently billable, which can be a risky position to hold within an agency environment. You always want to have a clear role, and you always want to be billable. Always.

As it turned out, the timing was on my side once again. The agency was just about to undertake planning for a campaign in support of Liberty Mutual's Winter Olympic sponsorship and was in need of someone to help ensure that this integrated campaign was, in fact, fully integrated.

Having backfilled my day-to-day social media role, I was now free to spend my days moving between the media, content, creative, technology, and social departments, acting as the glue and working to ensure everything we were doing was connected.

While not perfect (these things rarely are), the final result was a marked improvement over previous campaigns, with "Rise" launching in January 2014 as a unified program spanning digital and traditional channels simultaneously.

As the details of this campaign were finalized, I again began to get restless. Maybe I saw the writing on the wall, maybe I wasn't able to outrun that inevitable jaded feeling, or maybe big advertising just stopped being fun for me. Whatever the exact reasons, I found myself becoming increasingly frustrated with the heaviness of it all. What were once tolerable annoyances with the process and what passed for "good work", were now starting to boil over, and I decided it was time to step away.

It was a tough decision, but once it was made, I felt a wave of relief, of freedom, of excitement. Not because I disliked Hill Holliday (quite the opposite, I love(d) it), but because the future was in my hands. There were possibilities in front of me again. Possibilities that I could control.

Making things more interesting (again, timing is everything), my friend and planning/strategy/creative partner in crime Thomas was feeling similarly. So similarly, in fact, that he, too, had decided it was time to move on and try something different.

During moments and days of frustration in the past, Thomas and I had casually discussed "doing our own thing" over countless beers at Clarke's.

So had everyone, though. Clarke's was littered nightly with frustrated ad duos complaining about work and talking an ambitious game after a few pints. But rarely did anything material come of those bitch-sessions. After all, it was a pretty big leap from talking tough to walking tough.

But here we were, sitting on our bar stools once again. Except this time, we had moved beyond talk. It was time for action.

Heart
Founder/Partner - 2013 to 2014

Momentum in moments like these is everything. If we were going to formalize and do something, we needed to hit the ground running. No vacation, no sitting on our heels, no ambiguity about where we were headed or what we were setting out to do. We had to convert this frustration and fear into energy.

In order to "launch", we needed four things - a name, a website, an office, and a boatload of confidence.

We threw around a handful of names, but none felt right. For a minute, we leaned towards "Misfits & Makers" which was the best of the weak lot. Luckily we didn't stick with it because that name sucks. Instead, we returned to an old business plan that Thomas had written for a creative shop called "We Make Heart" which we both loved. What we loved, even more was just using the name "Heart" - because in a single word, it told everyone exactly who we were and what we were about.

We got some freebie office space in Boston's South End (thanks, Sarah!), and we put up a rag-tag website, which in hindsight, probably read a bit juvenile at the time. But it served its purpose, getting us a bunch of attention and rubbing a few people the wrong way in the process.

The swagger came easy, as did a flurry of funny press that we did not expect. It turns out we were a convenient foil for major agency stories back then, and we got some good mileage out of that. Even though many outlets printed "quotes" from me that I literally never said. I guess maybe what I actually said wasn't interesting enough.

When the dust settled (which was quickly...the industry news cycle is 24 hours, max), it was time to get to work. We fell a bit ass-backward into some quick jobs, and right out of the gate, we were making money. This was easier than we thought!

But the curse of early easy money was complacency. And going into the winter holiday, we were staring at a pretty dry pipeline. While working on our initial projects, we hadn't been thinking enough about the next job, and when the work stopped, it stopped abruptly. The novelty had worn off, budgets were not moving, and the reality of bootstrapping a business from nothing was setting in.

Worse still, with no client work to occupy our time, we fell into the dangerous trap of tinkering with and overcomplicating our own offering - searching for an open niche in the market to occupy. We agonized over bits of language, wrote and rewrote and rewrote again, and lost countless hours chasing our tails trying to thread some terminology needle of our own making - solving for a problem that no one even saw but us. All the while watching confused clients walk directly out our front door because they didn’t know how to buy what we were selling.

After spinning around for the better part of two months, we decided to simplify how we positioned ourselves drastically. We pivoted away from being a vague strategy and ideas shop and very deliberately began calling ourselves a creative agency. Websites, banners, ads, whatever you wanted...we could do that. Simple language, simple offering, no preciousness. We were a creative agency straight away.

From there, it became about inbound and filling the funnel as broadly as possible - getting clients in the door with block and tackle projects, then looking to get to more interesting work once trust was established. And while this new approach started to loosen things up fairly quickly, we knew it would take some time before this would really bear fruit.

Unfortunately, time was something that I (personally) was running out of.

When I left Hill Holliday and started Heart, my wife was three months pregnant with our first child. This was not an insignificant added pressure, and with it would come a set of milestones against which I'd measure the business as it related to its impact on my family situation.

One of those milestones was my wife's return to work after maternity leave and our subsequent need to send our daughter to daycare - at a cost of nearly $3,000/month.

Dropping your three-month-old kid off at daycare for the first time feels like a punch in the gut. Dropping her off at daycare so that you can go to a job you don't love - a job that barely covers the cost of sending her to daycare in the first place, feels like an uppercut on top of it.

So I decided it was time to make a change.

🗓️ Present Day

Upon leaving Heart, I decided to take a few months off and really think deeply about what I wanted to do for my next act.

I spent two days a week with my young daughter, enjoying some downtime in the summer, and the other three days a week cross-crossing the city, having coffees and beers with anyone and everyone in my network who would take the time out to meet.

I chatted with friends in venture capital, friends in advertising, and friends at in-house brands and startups. I got good advice, and I got bad advice. I went on interviews, had phone calls and sidewalk chats, and did all manner of things to try and home in on where I wanted to point myself next.

It was fun and informative and energizing and centering in all ways that I hoped it would be.

And as is often the case, my next move would sneak up on me rather unexpectedly.

One afternoon, while home with my daughter, a recruiter reached out about a role at EF (Education First), heading up the global marketing and creative team for one of their cultural exchange products.

I remember thinking that while this role (on paper) didn’t seem very interesting, it was only a few minutes from my apartment. So, why not go check it out?

Long story short, I fell in love with the people, the place, and the opportunity. And in October 2014, I took the job and the responsibility of running a 30-person marketing team that covered business in 26 countries across 14 languages.

And after three years in that role, in December 2017, I took over a 60-person creative and marketing team for EF Educational Tours - which I ran through December 2019.

Next, I spent five years heading up marketing, creative, and technology for the higher-ed division within Education First, including EF Gap Year and EF Study Abroad.

Currently, I am leading a new initiative within EF Education First, building out a Lifecycle and Loyalty marketing group that will work to better connect and leverage the broad network of businesses and product brands here at this amazing global organization.

Someday, I'll write in more detail what I learned from my summer off, the job search I undertook, and my fantastic time at EF so far. But for now, I've got work to do.

And as always, follow along with me here or here for more frequent updates.