Who's Craig Garber
Fun Stuff Outside of Work
I'm originally from New York City and have been living in Florida since 1989. I live in Tampa with my wife of 34 years, and what is almost certainly too many rescue cats.
For a lot of those years, work - and suffering over work - came first. Over time, I realized success wasn’t a win without a life outside of work, more time together, and time for activities I enjoy. So now I make sure our lives come first, work after that.
We have 3 adult children, and besides spending time with my wife, I love playing guitar, working out, listening to music, and traveling. I also enjoy street photography, meeting new people, interesting conversations, good coffee, a good cigar, and the occasional whisky.
I live in gratitude, and I don't mean this in a new-agey way. The truth is, considering where I started and where I am today, I feel incredibly fortunate.
I’ve been lucky enough to overcome a ton of obstacles and build a life I genuinely enjoy. I've spent over three decades with a woman I love... raised three adult children, all of whom, thankfully, still talk to me... and I still wake up curious and excited about what’s next.
That’s what I mean when I say I’m grateful.
Business is important. So is everything else.
(Bryant Park Holiday Market)
Lessons, Wins & Mistakes
I started working at 14, and never looked back...
After college, I began my career as a "Big 8" CPA, auditing Fortune 500 companies, S&L's, and manufacturing companies. From there, I spent several years in sales before spending nearly two decades as a direct-response copywriter and marketing strategy consultant, working with over 300 clients across 120 industries. Over time, this evolved into the work I do today.
Along the way, I was a property and casualty insurance agent. Fun fact: my wife was my client before she was my wife. I also ran an estate & financial planning practice, earning the CLU & ChFC designations.
I owned and operated several businesses, including e-commerce (vitamins, supplements, skin care, merch) & publishing... spent years in real estate wholesaling, and made more than my fair share of mistakes.
These experiences gave me a firsthand understanding of analytical, regulated, and relationship-driven businesses. It also taught me how to recognize connections between business decisions and customer behavior - and why they may be difficult to see from inside the business.
One of the most meaningful experiences of my life was interviewing 950 musicians, producers & engineers over seven years, as the host of a podcast called Everyone Loves Guitar. From major international touring artists to prolific session players most people have never heard of... these conversations were never really about music or gear. They were about people's lives, creativity, work, relationships, decision-making... overcoming addiction, trauma, difficult childhoods and countless other challenges… and the unusual paths people take to build meaningful lives and careers.
When people ask where my perspective comes from, it’s a combination of everything: Resilience and lessons learned from a challenging childhood... decades of business experience... thousands of conversations... a lifelong curiosity about people and their journey... being open to possibilities... and an ongoing effort to understand why some things work and others don’t. An interest that began long before I put on my first business suit.
And of course, from making mistakes. Lots of ‘em. I think paying tuition in the form of mistakes is ultimately one of the best teachers - as long as you're open and honest with yourself about what's going on. Being honest with myself has helped me quite a bit.
If you want to get a sense for how I think and how I approach conversations, feel free to listen to a few interviews I particularly enjoyed from my Everyone Loves Guitar show:
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Ian Paice (Deep Purple) - A masterclass in humility from one of the most accomplished drummers in the history of rock and roll
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Jeff Carlisi (38 Special) - An incredible conversation about life, music, and reinvention. EVERYONE wants 38 Special to get into the Rock & Roll Hall of Fame. Except, apparently… the Rock & Roll Hall of Fame
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Al Berry - One of the most honest and inspiring conversations I’ve ever had. The grace this man maintained in what anyone would consider one of the most difficult points in a life, still gives me chills
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Beth Hart - A remarkable discussion about creativity, struggle, mental illness, and resilience
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Amy Ray (Indigo Girls) - An honest conversation about identity, conviction, creativity, and staying true to yourself
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Mark Farner (Grand Funk Railroad) - Truly one of the most unbelievable stories I've heard about a band getting screwed by their record company
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Andy Summers (The Police) - Yes, he really can't stand Sting, and for good reasons
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Matt Bissonette (Elton John, Joe Satriani, David Lee Roth) - A conversation that unexpectedly opened the door to faith for me
Some things changed. Others didn't.
(Fortunately, one of these changes was my hair!)
What I Like About My Work
I enjoy this work for a few simple reasons:
First, I get to spend time with intelligent, hard-working people. My clients introduce me to new business models, new ways of thinking, and new problems to help them solve. I’ve always been a curious person, and learning is what keeps me engaged and excited about life.
Second, I really enjoy talking with other business owners. We’ve chosen a path most people wouldn’t want. Building a business is difficult. It requires risk-taking, resilience, and a willingness to accept responsibility for our actions. And I’ve always felt at home around people like this, long before I even understood what this was.
Third, I got into this business because this is how my brain naturally thinks. I’m interested in people’s perspectives and feelings, but I'm also analytical, and naturally drawn to recognizing patterns.
Plus, connecting dots is what I'm doing anyway when I speak with people and listen to their stories and situations. In both professional and personal settings, understanding the "why" matters to me.
I like solving problems and talking them through thoughtfully and clearly. I've been extremely fortunate to have had a wide range of experiences in business and life. And I’ve learned some great lessons along the way.
I’ve also felt the cost of friction, and how it exhausts you in business and at home. Reducing unnecessary friction is now a major consideration in the decisions I make. I’ve learned that success isn’t just about growth. It’s also about creating a business and a life you actually enjoy living, every day.
That’s something I care about, and it’s one of the reasons I enjoy helping others do the same.
Hard work lets you build. Having fun sets you free.
Let's Stay in Touch
Occasional emails on making better business decisions, reducing friction, and having a business that's easier to run