Questions I Get Asked Most

I actually knew his brother AJ first. We sat next to each other at a Seton Hall basketball game, and years later, when I left SITO Mobile, AJ asked if I’d ever met Gary. Over dinner Gary asked me to describe what I do in one sentence, and I said I take dreams and visions and turn them into action plans. He told me he wanted to build a $500 million integrated, independent, international communications company and asked if I could help, and I said yes.

I started as a CPA in public accounting and was a global CFO by 30, so I came into marketing through the numbers, not the creative. That turned out to be my advantage. Knowing accounting and finance lets me fuel a founder’s vision instead of choking it. I took maybe one marketing class in my life, and I’ve spent 35 years in this business.

Vision isn’t enough. You need direction, and you can’t have direction if you don’t know where you stand. Besides vision, every growing business needs two things: knowing its numbers and integration. That’s what lets you spot patterns and grow on purpose instead of by guesswork.

Look at your calendar. Mark your hustle time in yellow and your paid, revenue-generating time in green. When the yellow starts crowding out the green, it’s time to hire. Some founders squeeze the baby so tight they choke it, so let go of what someone else can do and move to the work only you can do.

Fail fast, fix fast, learn fast. Speed is the differentiator, so get your content out, tweak it and get it out again instead of sitting in analysis paralysis. Then apply what you learned and lean into what’s working. Perfection is the death of innovation, and you can always make enhancements after launch.

No. I’ve spent 40 years in rooms at Goldman Sachs, Saatchi & Saatchi and VaynerX, and much of my success came from the second seat. I was once told I was too nice to become a CEO, and I didn’t change who I was because of it. Adapt to your environment, but don’t lose yourself trying to fit in.

The age of the logo was about authority. The age of the person is driven by authenticity, and people trust individuals more than corporate logos. Start with an anchor statement you can build your story on, then show up consistently. Silence does not scale, and if you’re not visible, you’re invisible.

vYve is leadership development and masterclass programming for entrepreneurs and Fortune 500 C-suite leaders who are running low in the tank. Andrea Sullivan and I built it as “the Passionate and the Practical,” pairing her C-suite world with my years serving entrepreneurs. Our first class ran 16 weeks, with a live kickoff in NYC, virtual programming and an in-person growth summit. The goal is to help leaders reach their greatest personal and business potential.

Absolutely, that’s exactly who I look for. Give your people a voice and encourage them to question the way it’s always been done. Someone still has to set the vision and steer, and that’s where experience earns its keep, because it shows you the pitfalls. And lead by example: if I’m in first, I make the coffee.

A visionary needs a partner to operationalize the dream. When a founder keeps throwing out big ideas, someone has to turn them into plans, structure and the right hires. I go wherever the founder needs me, and I work hard to fuel the vision rather than choke it in our own hallways.

I was CEO of SITO Mobile, a NASDAQ-listed company, and I’m glad I played that number one role. It showed me how lonely and difficult those big decisions are. It also taught me what I don’t want to be, which is why I’m happiest as a great number two who understands what the CEO is carrying.

Founders have the vision, but they’re often also the ones juggling ops, systems, people and processes. I’m bringing Factotum, the UK’s award-winning outsourcing agency, to the US so founders get senior expertise on demand and can hand off back-office work like bookkeeping, payroll and compliance. That frees them to work on the business instead of in it.

Even the most impressive leaders quietly struggle with loneliness and burnout, often at the exact moment everyone expects them to have it all figured out. Leadership is lonely. That’s why community and accountability matter: peers going through the same thing compress your learning curve and give you a sounding board. Iron sharpens iron.

Focus on your true strengths and double down on them instead of trying to be everything. Don’t be afraid to make mistakes, kill what isn’t working and try it again a better way. Give your people room to think differently, because “we’ve always done it this way” is how companies fall behind.