Evan Bryce Riddle shares his journey of building a $10 million business from scratch, reflecting on his background of financial scarcity that fueled his ambition. He discusses his struggles with commitment to various ventures due to fear of failure before co-founding Art of Mondays, a community-focused company. The video highlights the rapid growth of their initiative, the Founder Sports Club, and details their three-day cabin retreat where they mapped out a strategic plan to scale Art of Mondays to their $10 million goal, emphasizing community, content, and team building.
A cabin surrounded by a forest with text "$10 Million" overlaid, representing the business goal and the cabin setting.
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The word "stopped" overlaid on an image of a couple, symbolizing the end of his wedding photography venture.
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A screenshot of "THE TRAVEL" website, representing one of Evan's past online ventures.
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Evan and Jai sitting opposite each other with the text "an internal battle that lasted years", representing his prolonged struggle with commitment.
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Evan experimented with various ventures, including a travel website, wedding photography, videography, and a boutique marketing agency, but struggled to fully commit to any of them.
He was driven by the fear of failure and the prospect of returning to a state of financial insecurity.
An aerial view of a luxurious villa surrounded by lush greenery, representing Art of Mondays' focus on creating spaces for ambitious people.
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A graphic showing "$50,000" and arrows pointing to a website and a Stripe link logo, representing initial membership sales before the product was fully ready.
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Evan holding a sticky note with "A DEEP NEED NOT MESS THIS UP" written on it, reflecting the pressure and determination to succeed with Art of Mondays.
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A company founded with his co-founder, Jai, aimed at creating a community and experiences for ambitious individuals.
The company focused on travel, growth, connection, and inspiration through online business.
Despite initial success and revenue, the company faced challenges in scaling and maintaining financial stability due to its messy and financially unstable nature.
People playing padel tennis, illustrating the community activities of the Founder Sports Club.
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A bar chart showing rapid growth from December 2023 to April 2025, representing the quick expansion of the Founder Sports Club's membership.
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A split screen showing "Art of Mondays" and "Founder Sports Club" with text indicating "2155 founders in 45 cities played sports together in January," showcasing the reach of their community.
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A community-driven initiative that brings together entrepreneurs through sports and activities.
The idea emerged from playing paddle with friends.
Founder Sports Club grew rapidly, reaching 5,000 members in 150 cities within six months, becoming a thriving community within its first year.
Evan pointing to a whiteboard outlining the "Growth Engine" with "People, Product, Profit" and a "long-form" and "short-form" strategy leading to "$10M".
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Evan holding a paper illustrating the "$1M to $10M" growth target, symbolizing their ambitious scaling plan.
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A cyclical diagram showing "Attract, Engage, Convert, Referrals," outlining the optimization of the customer journey for growth.
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Evan and Jai locked themselves in a cabin for three days to map out a plan to scale Art of Mondays into a $10 million business.
The plan focuses on strengthening the core of the business by focusing on the community and optimizing the customer journey.
Restructuring the team and making key hires, specifically aiming for 15 rockstar individuals, is part of the plan to achieve their financial goal.
The ultimate goal wasn't just about making $10 million, but to lay the foundation for something that would shape the rest of their lives and the lives of thousands of other problem-solvers and travel junkies.
