I Went to a $14,000 Retreat for 9-Figure Founders in Italy

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Inside the Exclusive OOAK Mastermind Conference in Tuscany

In late August, the picturesque Tuscan hills played host to a unique gathering of some of the world’s most successful founders at the OOAK Mastermind conference. Held at the luxurious Castelfalfi resort, this retreat was not open to just anyone. Attendees, who collectively generate revenues surpassing those of some small countries, were required to apply and pay a steep $14,000 fee to participate.

Designed exclusively for founders operating seven- to nine-figure businesses, the event aimed to provide an intimate environment for high-level networking, learning, and strategic growth. Despite not fitting the typical profile of such an attendee, I was invited to witness firsthand the insights and exchanges that happen when elite entrepreneurs convene behind closed doors.

The OOAK Brand-Building Powerhouse

The mastermind was organized by OOAK, an innovative global consumer brand-building company known for creating, scaling, and acquiring brands. The event was spearheaded by OOAK’s three co-founders—Bob Verlaat, Nick Nijhof, and Vince Nijhof—all under 30 years old and childhood friends, with Nick and Vince being brothers. Their youthful energy belied the sophistication and scale of the brands they manage, drawing around 100 ambitious founders to Tuscany for the event.

Originally hosting smaller iterations in Dubai, the trio expanded the conference after overwhelming demand, turning it into a sold-out event that attracts the cream of the entrepreneurial crop.

The Experience: Luxury, Learning, and Networking

The setting itself was a highlight: the Castelfalfi resort, located in the heart of Tuscany, offered not only five-star accommodations but also stunning views and a quaint village with boutique shops just a short walk away. Participants enjoyed gourmet meals, including a memorable truffle-themed lunch featuring beef tartare, truffle risotto, and vanilla truffle mousse.

To attend, founders needed to demonstrate a proven track record with seven- to nine-figure brands, ensuring a high-caliber group. Besides the OOAK co-founders, speakers included industry experts like Jeff Srithongrung, director of creative strategy at TubeScience, who shared best practices for ad campaigns, and Ray Jang, founder and CEO of AI ad company Atria, who discussed how AI has drastically lowered the cost of testing advertising concepts—bringing experimentation “close to zero.”

Success Stories and Strategic Branding

One standout attendee, 32-year-old Alvaro Gellings, shared how he achieved $1.4 million in sales within the first hour after launching an apparel brand. His subsequent sportswear brand, Day One, leveraged a compelling influencer partnership with German endurance athlete Arda Saatçi. Saatçi’s 74-day, 1,960-mile run from Berlin to New York became a powerful narrative for the brand, demonstrating the importance of storytelling over just product quality in capturing consumer attention.

At the core of OOAK’s approach is the strategy of reframing “boring” products into emotionally resonant categories. For example, Dore & Rose, a premium sleep-wellness brand founded in 2022, markets mulberry-silk sleep products infused with silver ions not just as bedding but as beauty and wellness essentials. This repositioning taps into consumers’ desires for restorative sleep and overnight skin recovery.

Similarly, Hears, an earplug brand launched in 2023, transforms hearing protection from a medical necessity to a premium lifestyle accessory. By emphasizing the joy of clear and confident music enjoyment at events, Hears appeals to a fashion-conscious audience and partners with organizations like the Hearing Health Foundation to promote awareness and donate proceeds.

Impressive Outcomes and Ambitious Goals

OOAK’s portfolio brands showcase significant market traction. The company disclosed an annual revenue of $100 million across its brands, with a target to double that figure in the current year. Dore & Rose has sold over one million silk items and secured placements in prestigious hotels such as Four Seasons, Belmond, and Cheval Blanc, as well as partnerships with over 150 retailers including Nordstrom, Mecca, and Namshi.

Meanwhile, Hears reached $7 million in revenue within its first year (2024), selling over 250,000 pairs of earplugs and making a notable social impact through its collaboration with hearing health organizations.

Founders’ Wisdom: Embrace Risk and Adaptability

When asked about advice for aspiring entrepreneurs, Bob Verlaat urged potential founders to “just do it,” emphasizing that the worst outcome—failure—is not fatal. He credits their success to unwavering belief from the start. Vince Nijhof shared his motivation to pursue entrepreneurship as a means to work hard and achieve financial independence rather than working under a boss.

Nick Nijhof highlighted the importance of versatility in early-stage startups, encouraging founders to wear multiple hats and focus on the immediate next step rather than the entire journey. His pragmatic advice resonates with many entrepreneurs who face uncertainty but must keep moving forward.

For those interested in exploring the exclusive world of high-level brand founders and the strategies behind their success, the OOAK Mastermind conference provides an enlightening glimpse into the intersection of luxury, innovation, and entrepreneurial drive.

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