Experiments

Patterns School

In 2013, Patterns began as a physical school to teach creative individuals how to support themselves as artists. Backed by legendary companies like Adobe, Mailchimp, Media Temple, Harvest and more, it was a beautiful 3,000 sq ft experiment in doing things in the most original way possible. People said I was crazy to start my own school with no formal certification or permission, but I’ve never been one to ask. It was a passion of the heart and what I learned there continues to shape Patterns to this day.

Seth Godin

Seth is a 20x best-selling author, entrepreneur and game-changer. I learned so much of what I understand about business from him through conversations, books, courses, articles and so much more. In 2012 and again in 2014, I was able to work with him in his office on two projects. The experience was a memorable one and I’ll never forget what he taught me. I’ll also never forget when he asked me, “You’ve done some great work, but when are you gonna do the big thing?”. That stuck.

Cheddar

In 2012, I acquired a popular to-do platform with apps for the web, iPhone and iPad. After a complete rebuild and overhaul, I was able to sell it for a substantial return. I learned a lot about design, development, and productivity from building one of the cleanest and most useful platforms in the space.

Happy Monday

In 2011, podcasts were in their infancy. Although podcasts had been around for years, hardly anyone saw their potential. In fact, when I started Simplecast, friends in the industry that I respected told me Odeo had already been done and failed. It was a lesson in following your instincts because podcasting is still booming until this day. I co-hosted one of the first and most popular podcasts in the design industry. Supported by great companies like Mailchimp, Adobe, Media Temple, Harvest and more, it was an opportunity to lay the foundation for so many others to follow.

Creative Mornings

In 2015, as Simplecast was beginning to gain traction, I did a six-month experiment in NYC with Tina Roth Eisenberg to build Creative Mornings. It was a community-based company with over 170 chapters worldwide. I learned a lot about building communities, communicating at a larger scale, and understanding the power of network effects. I helped solidify major sponsors and refine systems for growth and connection.

Execute Ventures

After the launch of the Execute book, Drew Wilson and I decided to do an experiment in supporting other builders to create and launch applications at break-neck speeds. We hired a film crew to fly to Australia to document a small team of product builders. It was a fun experience and it stretched my understanding and knowledge beyond just product.

Execute Book

A modern manifesto on action, momentum, and building a life through movement instead of hesitation. After Drew Wilson launched Spacebox (eventually Plasso, acquired by GoDaddy), I interviewed him on how he built the product in a short sprint. I wrote the book in 3 days after that and we self-published physical copies within 8 days. It was an experiment in shipping faster than the voice in your head could stop you. Execute reframes execution not as hustle or discipline alone, but as a behavioral loop: spark → action → proof → devotion. The book explores why people stall, overthink, and wait for permission—and how to redesign those loops through systems, rituals, constraints, and identity. At its core, Execute argues that clarity comes from movement, not contemplation, and that meaningful lives are built through repeated acts of courageous action. Under the larger Patterns philosophy, Execute becomes the operating system for turning intention into reality.

Design Evolution Book

Originally a book about product and digital design, Design Evolution evolves into something much larger: a framework for understanding design as pattern-making. The book explores how all design—from interfaces to businesses to culture itself—shapes human behavior through loops of attention, friction, reward, and identity. Moving beyond aesthetics and trends, it reframes designers as architects of systems and influence. The central idea is that great design is not about decoration, but direction: creating intentional patterns that guide people toward clarity, meaning, and sustainable behavior.

Jenius Book

Originally framed around the idea of “genius,” this book transforms the concept into a philosophy of pattern intelligence. The book argues that intelligence is not a fixed trait or IQ score, but the ability to recognize, connect, experiment with, and refine patterns across life and work. It explores how creativity emerges from observation, interdisciplinary thinking, experimentation, and reflection—and how anyone can cultivate these loops intentionally. It is a book of uncommon common sense for building businesses and supporting projects.

Silence Book

Silence is a philosophical exploration of stillness, awareness, and the hidden architecture beneath modern noise. The book examines how distraction fractures identity, attention, and meaning—and how silence acts as the precondition for clarity, wisdom, and conscious design. Rather than treating silence as emptiness, the book reframes it as a generative space where deeper patterns become visible. Through reflections on technology, philosophy, spirituality, creativity, and human behavior, Silence argues that modern people are not starving for information, but for stillness.

Other Notable Projects Included:

Execute Podcast, Execute iOS (online course), The Great Discontent (sponsorships), Brooklyn Beta (hosting and sponsorships), and Treehouse (online tech education).