Meet Expert in Residence Matt Gartland

How did you get started in entrepreneurship?

I chose to “retire” from my leadership-track career in enterprise IT to get into startups. I’d always been an entrepreneur at heart going back to childhood. And I’d been motivated to become a full-time entrepreneur ever since the early days of the dot-com revolution.

The decisive moment came very unexpectedly: a mentor of mine from the corporate world left to join a mega venture-backed med-tech (medical technology) startup. He recruited me to join his senior team on a one-year contract. That was on a Friday; I gave notice the following Monday. The deal with my mentor was one year only because we both knew that med-tech was not where I wanted to be long-term. So, in parallel, the aim was to start my own venture in an online market segment that fascinated me and transition it into full-time at the end of the contract. That’s when Winning Edits, my creative agency/studio, was born. It was very early days in what we now call the “Creator Economy.” There are a good number of these service-based firms today; back then, not so much. Little did I know then that it would be the catalyst for so much of my entrepreneurial growth to this very day.

What makes you tick?

Engaging in high-performance pursuits that aim to achieve big goals and serve others along the way. Within that context, leading others and playing an influential role in their own leadership development is a massive motivation. Nothing makes me happier than when my team, my partners, my friends, my members, etc., knock something out of the park and I know that I’ve played a small (or large) role in helping them achieve that.

Additionally, my self-improvement drive at all levels is both irresistible and unquenchable. This intrinsic drive comes, in part, from the chip on my shoulder that I’ve carried most of my life. It comes from people expecting less of me, betting against me, bullying me, betraying me, etc. Every time I get punched in the mouth — metaphorically speaking, and that’s happened a lot — I come back stronger and more ready for what’s next.

What does an average day in your entrepreneurial life look like?

Depends on the day. 🙂 My routine is an asymptotic work in progress. Much of my day, most days, is spent helping others: coaching my direct reports on how to solve an emergent problem as leaders; interacting with our community members and helping them think through a new opportunity or challenge; teaching my mastermind members the ins and outs of business-critical disciplines like strategic planning; connecting with my partners in private and being their safety outlet for whatever new fear, challenge, or insecurity they have and need to process; talking with friends at other companies about their growth plans and where, if possible, we can help one another.

Somewhere in all of that, I carve out time for my own work: developing and expanding the vision for the company, forecasting the future in numbers, staying up to date on the industry (as best I can without going insane from all the noise that’s shared online), and crafting thoughtful content that aims to express a strong, clear, and opinionated point of view on the world of entrepreneurship and what the future of small business online looks like.

What are your areas of expertise?

I’m a founder and leader with lots of range. Rather than a very narrow specialization in only a single field, my career has afforded me opportunities to get very good at the skills needed to succeed as a non-venture-backed startup founder leading companies and teams with long-term ambitions.

Leadership itself is a pronounced area of my expertise. I was incredibly fortunate to be exposed to world-class leadership training beginning in my undergraduate studies and accelerating through an exclusive leadership development program in the corporate world at the start of my professional career. I’ve gone on to hold various executive leadership roles in a number of startups I’ve either founded, co-founded, or been a partner in. At the top level, leadership comprises many components: vision, team-building, relationship-building, persuasion, negotiation and deal-making, etc.

Additionally, I’m an expert in small business finance, which — while not classically trained — I’ve figured out myself by doing the work aided by my studies in data science and technology. “Product” is another strength, largely in the tech and education/community sectors.

Finally, the confluence of all things operations and management has become a strong area of expertise over time. From designing organizations and standard operating procedures to orchestrating how to craft, govern, and execute various projects and innovation initiatives, all roads usually lead into this body of work.

What are you looking forward to most in your residence with the SPI Pro community? How specifically do you want to help entrepreneurs?

I’m most looking forward to playing a major role in helping independent entrepreneurs achieve greater levels of resiliency, sustainability, and longevity in their businesses. Most small businesses don’t make it; in fact, 50 percent of such companies flame out by the five-year mark. Pros are at the point in their own entrepreneurial journeys where “what got them here isn’t likely to get them there.” It’s an exciting, challenging, and rewarding time in the lifespans of those small businesses. Helping them successfully evolve into their next lifecycle phase is incredibly rewarding work.

For me personally, that “work” manifests as a deep concentration on business fundamentals upon which small businesses can build for the long term. Strategic planning, business finance, executive leadership disciplines, team-building, product development: these areas (and more) are core to the long-term prospects of small businesses in any market.

Why did you join the Expert in Residence program? What is it about Pro that makes it a special place/community for entrepreneurs?

The EIR Network is precious to me because it directly targets a massively under-served need in the “become an entrepreneur” market: actual business mentorship, training, and support that isn’t one-dimensional, marketing-only, and/or mostly hype and inspiration without much substance. Most brands and personalities out there don’t help independent entrepreneurs in a complete way. Lots of the advice is super-niche, often shallow, difficult to replicate, and skewed heavily toward the outdated notion of building an audience first, at all costs, and then figuring out your business later. Maybe that worked in 2012; it doesn’t today, a decade-plus later.

The internet is a different place. Macro market conditions have changed, dramatically. People’s individual circumstances and finances face new needs and challenges. The EIR Network within SPI Pro is our outspoken answer to this problem. Instead of indexing only on one “niche,” we are building an integrated network of legitimate business experts spanning the diverse aspects of small business. Where others provide incomplete experiences and expertise, we provide full coverage. Where others hype up a single marketing channel, we discuss aligning with the right marketing channel for you. While others seem to forget that marketing is very different than sales, we don’t, and actually help our members with sales-based questions and needs. And where most ignore the presence and importance of finance, we celebrate it, talk about it, and help our members with all manner of finance questions.

All of that together is what makes SPI’s EIR Network so very special and different from the rest.

What is your biggest professional challenge to date, and how did you overcome it?

Broadly speaking, the doubt and disbelief of others. The average entrepreneur will face a good bit of skepticism throughout their journey. I feel I’m above average in this regard. But that’s okay; I’ve come to see all that as a notable competitive advantage. When you’re the underdog, it gives you more space — which is what you need to adapt, innovate, and seize opportunities. And per my personality and character, it adds to my drive. I wasn’t always grateful for this set of challenges, but I am now. And I’m grateful for yet more of this to come.

What is your biggest professional win to date and what did you do to make it happen?

I have maintained some of the closest and most treasured relationships in my life since the early days of my entrepreneurial career. It’s extremely hard to do this when you’re an ambitious entrepreneur operating in an environment that often celebrates and incentivizes fame, ego, opulence, status, and other forms of self-interest and comparison. It’s extra tricky when deep friendships form with those you work with — partners, employees, anyone.

During these years, I’ve been on the receiving end more than once of a close friend sacrificing our relationship to protect their own self-interests. These moments have been few and far between. Nevertheless, they’ve had an outsized impact. Learning to forgive has been hard, but it’s absolutely what’s helped the most, in part because it’s made me that much more grateful for people in my career and life like Pat (my dear friend and partner of 10-plus years) and Mindy (also a dear friend and my first employee from ~2010 who is still on my team). Those relationships promote the values and principles that remain near and dear to me: humility, hard work, generosity, optimism, resiliency, and abundance. Those qualities seem to sell for very little — I refuse to sell. In doing so, it’s led me — through one form or other — to others who believe and behave similarly, including Jason and Terry — our first two amazing EIRs inside SPI Pro — whom I now consider friends as well.