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Four Years North of the Wall

Matt Mittino
7 min readMay 21, 2019

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I’m coming up on a major anniversary.

August 1, 2015 was the first day, in more than 20 years, on which I didn’t have a corporate job. The easy math tells me I’m soon to mark four full years I’ve been north of the Wall and out living with the wildlings.

As I’ve written about before, Why I Did What I Did, going off the rolls was on purpose — after an ever-expanding career with a fantastic, global, industry-leading life-sciences company, and a timely divestiture, I decided to strike out into, for me, unexplored frontiers.

On July 31st, 2015, I walked through the gate at our office and left the safety and security of the large, corporate kingdom behind. I was striking out to explore the world of entrepreneurs, investors, advisors and coaches.

I wasn’t sure what I was getting into, though I did feel I was prepared — I knew I had built up the skills and tools that would help me survive. I just wasn’t sure how I’d apply them in the new world.

This post comes as I look back on the last couple of years of serving as an advisor, board member, VC-backed portfolio company CEO, and most recently “back to work” leading the European business for a medtech startup.

I capture a few observations to frame the new world in the light of the old. So here goes . . .

This is a whole different world

What struck me immediately was the real focus on business — on customers and product. I’ve been amazed at how much time I’ve been spending on building businesses — actually applying knowledge and skill to launch or grow a new company or product. Nearly all of my time has been spent working with companies on the business — no discussions about enhancing corporate finance processes or global SAP implementation. These companies are able to leverage my experience in strategy, sales and marketing, coaching and executive development, product design, market research, and commercial execution to drive their businesses forward. I’ve seen small teams make great strides in a short time because most of the energy is going toward building better products and selling them.

And speed. The hustle. Shocking. I have a real sense of what the speed of business is today and we are talking hours, not days or weeks, to execute. I was impressed with one team’s ability to identify issues, discuss, analyze and take action. Every Monday morning, that CEO and I met for coffee. We would have lively discussion about the business — direction, customers, sales, partnerships — and, at the end of each weekly coffee meeting, with any decisions we had made in-hand, we walked across the street to the office and implemented. Within the span of a few hours, we would analyze, debate and decide. And we were able to drive remarkable growth in the sales trend and take important decisions about the direction of the company. That was really speed. I am helping companies get to decisions in hours, that would have taken me weeks or months to coordinate in my prior corporate roles (e.g. licensing of products).

Resources, it probably goes without saying, are tighter. Not just cash, but personnel. Fewer hands to do the work makes prioritization a constant battle. Not so different to large companies, but I see the preoccupation with resources can have a crippling effect on getting things done. In these small companies, money panic can drive inaction, even on important activities. With less experience it’s difficult for some new CEOs to know how to leverage outside resources (designers, writers, independent attorneys, translators, social media pros, health economics experts). This was an interesting find given that there is so much of the current employment culture is gig culture. I would have expected more knowledge of, and readiness to embrace, more outside resources. It doesn’t all have to be hired in.

But, It’s actually not so different

“What’s our value? What problem are we solving? What pain are we treating?”

“Who is going to benefit from this? Who are we selling to?”

“Why do they want this product?”

I’ve repeated these and similar questions non-stop over the last couple of years; in different settings, with different companies driving toward the same outcome — better understanding of the business we have and how to grow it. It’s common for me to see companies not have a clear sense of the value of their offer and/or who really wants it. Asking these questions helped when I led my own corporate teams and they are paying dividends with these new organizations. These are essential questions each business leader needs to answer. In the past, I worked with my corporate product teams struggling to find this clarity, and can see these other companies dealing with the same challenge.

When products hit the market, it has been pleasing to see a focus on performance indicators. Maybe the CEOs are sensitized to the need for monitoring due to the dearth of advice published about start-up analytics. I am a firm believer in measurement and monitoring. But I believe more that there are appropriate metrics for any given time and place of the evolution of the company and not every metric of the moment is for every company. I was surprised by this focus on performance indicators without really understanding why. As an example, I worked with a CEO who was obsessed with customer acquisition cost (CAC). He had to know the customer acquisition cost and spent a lot of energy calculating it. In the prior year, they had closed less than 100 customers. The ultimate goal was to reach into the hundreds of thousands with similar resources. The CAC was too high and I didn’t need an excel spreadsheet tracking a weekly metric to know this. A hand-full of new customers a month was not efficient nor acceptable nor ready-to-scale. Getting all spun up about a CAC metric didn’t fit the stage of the company. We probably should have been more focused on current customer metrics like engagement, repeat use, or duration of use. Or really tracked well the actual acquisition process vs. the costs until we had something we felt was solid. Tracking for the sake of tracking isn’t adding anything.

This type of move drives a lot of introspection

One thing for certain I wasn’t prepared for was getting out from behind the company brand. Representing my own brand.

Though I had worked on personal branding and identity before leaving the job, I hadn’t thought about it profoundly enough. It was weak, surface-level thinking. Being out on my own, without the name of the company to stand behind, was more of a struggle. I was responsible for crafting, presenting and building my own personal brand, and I needed to appreciate more how much control and thought it takes. Without the company brand and title, without a strong personal brand and personal direction, I had no identity. Having been a very successful executive (and with years of development plans and leadership assessments), I was surprised by how much I needed to re-think about what I do, about my unique value, about what I want.

I really became aware of the problem when I had the opportunity to represent one of my start-up clients at a pitch event. The CEO recommended that I use the standard company pitch deck. I assumed he was well versed in pitching the company. I assumed his pitch deck would fit. Hell, he had already used it to raise the first round of venture money. As I sat through the two opening presentations of the event, I knew we were in trouble. I jumped on stage, and in front of important investors and other hot start-ups, I gave a terrible presentation (of course trying to save what I could in the meanwhile). I slipped back to my seat and realized that though the company certainly wasn’t going to win an award, I had made a huge personal error. If the pitch had gone well, I could have picked up new clients or partners and/or made new important connections. As much as the company came off looking poorly, so did I. It was as much me on stage as the company and I didn’t prepare to deliver my best.

The new brand is “me” and every single opportunity is less about the company I’m working with and more about my personal brand and how I’m building it. Needless to say, I took control of the next opportunity and made a killer pitch. Lesson learned.

Too, I found many more big swings between emotional highs-and-lows. Since there’s no consistency in the day-to-day operation of “Me Inc.”, one day would be: “This is fantastic. I’ve got great traction and made some great contacts. Things are going well.” day. While the very next day could be a: “What am I doing? Will this work out?” day. Without a guiding star, it’s tough to know if you are on the right path.

So where did I end up?

I know that what I do is build businesses and teams. Maybe this hearkens back to my early days as an engineer and so isn’t a far leap to understand, but it took some time to really reflect and get comfortable with this identity. I’m not the idea guy that has a burning product idea in my head that needs to see the light of day; nothing I need to birth to the world. I don’t have a company to launch. I’m not a venture capitalist. What I can do is quickly assess a business situation, build a course of action, and motivate a team to go along for the ride. That’s what I do. I grow and operate businesses. Give me a problem to solve in business and I’ll fix it.

The upshot of all of this introspection is confidence. Some will say it wasn’t possible for me to be more confident, but there it is.

This seems long enough. It’s clearly not a full analysis of the last few years; just a few observations.

Before I walked through the gate after turning in my company ID, I thought: “This could really suck; I wonder if I’ll have to go back home.”

For now, I can report, I’m still out and about.

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Matt Mittino

Family First --- CEO | BOARD MEMBER | ADVISOR --- My own views on management, authenticity and leaving the corporate nest. Find me here: http://bit.ly/2gOgf06