About

Tony Lillios

Hi there, I’m glad you’re here! Here's a bit more about myself. I’m the kind of person that steps into challenges while learning and growing through it. I love to work with and inspire that in others. My breadth of adventures personally and professionally often elicit the moniker, the World's Most Interesting Man! While I don’t drink Dos Equis, I do find others equally fascinating and have a passion to connect and co-create possibilities.

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Breaking Boundaries. Blazing Trails.

My first product design review at Apple was terrifying. As a young designer, I found myself trying desperately not to say anything stupid while presenting my team's work. This exhilarating mix of fear and possibility would come to define the most meaningful moments of my life.

I started my career as a young designer with IDEO, learning to navigate the high-stakes world of Silicon Valley innovation. I couldn't have imagined that within a decade, I'd co-found Speck Design and Speck Products that would propel Dell laptops from niche products into mainstream success, designing the hardware for multiple generations of Cisco Systems routers and then pioneering an entirely new category of protective cases for mobile devices that would grow into a business that sold more than $1 billion in product.

But success brought its own kind of constraint.

As we scaled rapidly - starting 5 companies in the process and landing on the Inc. 500 list three years running, reaching as high as #41 - I found myself becoming someone I didn't recognize. My critical designer's eye - trained to find flaws and improve them - had transformed me into someone perpetually dissatisfied, constantly judging everything and everyone around me. My responsibilities as a leader to our customers, clients and employees fueled me to do more and more.

Professional success masked a growing internal disconnect.

The wake-up call came during a rare sabbatical. Away from the relentless pace of startup life, I realized I'd become defined solely by what I did, not who I was Being. This insight sparked a personal revolution that would alter the trajectory of my life.

I set out to test the boundaries of my own limitations, starting with a seemingly impossible goal: completing an Ironman triathlon. I still remember standing at the starting line in Western Australia, having impulsively signed up months earlier, thinking: "Other people are Ironman athletes. Not me."

But I finished. And something profound shifted - "What else was I convincing myself I couldn't do?" This question became my compass for exploring what other self-imposed limitations were simply in my head.

Many more Ironman competitions have followed, including the World Championship in Kona. I pioneered the first-ever double-crossing swim of Crater Lake; traversing North America's deepest lake without a wetsuit or any assistance.

With each physical boundary broken, internal barriers fell too.

My expanding sense of possibility led me to Bhutan, where I helped create and execute the first human-powered expedition across the entire country - a year-long undertaking culminating in a 42-day journey documented in the film "Crossing Bhutan". Traversing mountains under my own power while immersed in a Buddhist-fueled country gave me a fresh perspective: life itself is a sacred adventure, not just a series of achievements.

When all the companies we founded, including Speck Products, were ultimately sold, I faced the entrepreneur's existential question: "What's next?" Rather than starting another company, I chose to help other leaders navigate their own crossroads.

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Around this time, I also challenged conventional expectations in my personal life. After coming out in my late twenties and reimagining what family could look like for me, I became a single father through surrogacy - pioneering yet another path less traveled and finding profound fulfillment in parenthood on my own terms.

Listen here for: - more about my journey to parenthood

Recognizing that my experience alone wasn't enough to effectively guide others, I spent two years training as a certified coach. Few successful entrepreneurs invest in mastering the art and practice of coaching, but I knew that combining my business experience with formal coaching methodologies would create something uniquely valuable.

Today, as a Leadership Coach, I work with high-performing executives who, despite their success, feel they’ve hit some limits. They are looking for more than tactical business advice; they want to increase their leadership acumen while growing personal fulfilment. Our work creates more skillful, clear, and effective leadership that drives tangible results with less stress and drama. I help illuminate what's possible when you consciously choose who you're being rather than obsessing over what you're doing.

The most powerful shifts happen when we learn to integrate our full selves into our leadership - when we bring not just our skills and expertise, but our authentic presence, values, and vision to our work and lives. This integration creates a foundation for more meaningful achievement and impact.

That's the journey I'm on, and the one I help others navigate.

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