The startup community curing the Sunday scaries

Business networking is fundamentally broken. The traditional model built around LinkedIn, corporate retreats and boring presentations often feels more like a corporate chore than a genuine opportunity.
According to a survey cited by SalezWORKS, 73% of professionals actively dread networking events. Retreats often feel like training camps to reinforce a business culture that prizes superficial connection over meaningful interaction.
This is exactly the problem the founders of the Art of Mondays decided to change. Art of Mondays is an exclusive community actively dismantling the outdated conference model and replacing it with something radically different.
Founded by two young Australians, Jai Howitt (28) and Evan Bryce (31), Art of Mondays is an application-only community dedicated to “lifestyle founders.” These are entrepreneurs who run online businesses, travel the world, and prioritize their physical health and genuine friendships over perpetual burnout.
Their core philosophy is simple yet subversive in the modern startup world: work to live, not live to work. Both Howitt and Bryce run the company remotely from anywhere in the world, living the very lifestyle they champion.
“We believe that you can create a business that works and also not have to sacrifice the love of your day-to-day life,” explains Bryce. “There’s always time and place for [the hustle]… but we take that business side of things and combine that with our personal philosophies.”
- Global Reach: Intimate 10-to-12-day residencies held in diverse locations like Japan, Alaska, Italy, New Zealand, Australia and South Africa.
- Camp Mondays: Recently, they booked out an entire French village for 112 vetted founders. The event featured special guests like Sam Kolder and Matt Gray. Demand was so intense that tickets sold out in minutes, with one batch vanishing in just 71 seconds.
- Future Adventures: This September, the community is taking over a private island in Southeast Asia for an event appropriately dubbed “Founder Residency: Castaway.”
The big idea: Summer camp meets business education
Instead of renting out lifeless convention centers, The Art of Mondays moves founders into rural villages or onto private islands. For a few years, it has conducted its residencies (Bryce told me they prefer not to call them retreats because of the continuing value they offer members) at inspiring locations around the world.
In these 10- to 12-day sessions, they live, build, play and connect. The idea is to bridge the gap between childlike play and serious business problem-solving, and the founders’ intention is to replace superficial contacts with genuine memories and life-long connections.
Bryce, who has a background in facilitating youth camps, integrates these informal educational elements into the retreats, utilizing games and activities to break the ice among highly successful adults.
Howitt’s background is equally untraditional. “I think for him, a lot of his entrepreneurial drive comes from his parents,” said Bryce, “because they invested a lot in alternative education for the kids,” even spending six months traveling the US in an RV while being homeschooled. “They would play CASHFLOW at the dinner table.”
This shared appreciation for alternative learning forms the bedrock of their events. As Bryce notes, “You can learn about business anywhere, but where can you get that feeling of true belonging? Where can you get that feeling of youth or nostalgia that you had going to summer camps as a kid? I think that’s what makes us really special.”
Over time, Howitt and Bryce have perfected the recipe for these trips. “The first few days must be about connection. It must create vulnerability because vulnerability is the fastest way to connection,” says Bryce. “Then the next few days are always about collaboration and creation, and the last few days are usually about celebration.”

Protecting the Vibe: The Strict Vetting Process
The model isn’t just an idealistic concept. The demand for their residences has grown exponentially. In just two years, the company has executed around 30 founder residencies across six continents.
With over 7,000 applications and only about 300 accepted members, Art of Mondays boasts an acceptance rate of roughly 3.8%. This exclusivity is entirely by design. Prospective members must meet specific revenue requirements and run an online business, but the ultimate deciding factor is values alignment.
“We’re not trying to be the community that grows the fastest and makes the most money,” Bryce notes. “We’re not the kind of founders who wear Rolexes and drive Lamborghinis. We’re the kind of founders who maybe make a fair bit of money but give that money to their parents to help them retire, or go on a trip.” He calls the kind of founders attracted to Art of Mondays the “quiet achievers.”
Ego is left at the door, and presence is prioritized. During events, they actively promote digital detoxes.
“Offline is the new luxury,” Bryce emphasizes. “We’ll do family-style dinners … and we just ask everyone to leave [their] phones and don’t bring them to the dinner table. And then we’ll hold hands and do a little gratitude at the beginning.”
Redefining the Monday Morning
The partnership between Howitt and Bryce started through a podcast interview and was cemented by a shared work ethic. Howitt serves as the creative visionary, while Bryce acts as the logical operator. Together, they are aiming to cure the isolation often felt by solo entrepreneurs, offering virtual monthly calls and an online hub alongside their physical events.
As for the name of the company, it strikes at the very heart of their mission. For most of the world, Mondays are synonymous with the “Sunday Scaries” and the dread of the daily grind.
“Most people dread waking up on a Monday. They have to go to a job they hate just to pay the bills,” says Bryce. “The Art of Mondays comes from the idea of, if you can create a life that you can’t wait to wake up to — if you can’t wait to wake up on Monday, that’s the goal. How people feel about Mondays often is a representation of how they feel about a lot of things. So we want to make Monday the best day of the week.“
Brooklyn-based financial journalist Will Kenton has over a decade of experience covering the intersection of money, economics and culture. Specializing in investing, personal finance and retirement planning, his work has appeared in Investopedia, AP News, Business Insider and TIME Stamped. While at Investopedia, Will was the creative force behind the Anxiety Index, a proprietary tool used to gauge investor sentiment. His expertise is rooted in behavioral economics — a field he explored as associate editor of the New School Economics Review — and he aims to help readers navigate the “predictable irrationality” that influences financial decisions. Will holds a BA from Ohio University, an MA in economics from The New School and a Ph.D. in English literature from NYU. Beyond his financial career, he is also an award-winning playwright featured in the Red Bull Theater’s annual festival.