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

I first saw the hotel Castelfalfi from the back of a cab, its stone exterior rising out of the Tuscan hills. Inside waited founders who collectively generate more in annual revenue than some small countries — and each had paid thousands of dollars for the privilege of being there.

On paper, I had no business being at a $14,000 retreat for seven- to nine‑figure founders in Tuscany. I don’t run a massive consumer goods brand or a unicorn startup, and my net worth is far from impressive. But when I was invited to sit in on three days of keynote sessions and fireside chats at the OOAK Mastermind conference, I couldn’t turn down the chance to see what happens when ultra‑successful founders gather behind closed doors.

OOAK Mastermind was hosted by OOAK, short for One Of a Kind. The global consumer brand-building company creates, scales and acquires brands.

The three co-founders of OOAK were everywhere at this event. Bob Verlaat, Nick Nijhof and Vince Nijhof delivered the keynotes and moderated the fireside chats. The three of them are actually best friends from childhood; Nick and Vince are brothers.

The three founders came up with the idea for this event after hosting two smaller iterations in Dubai. They originally intended to keep this conference small, with only a few dozen participants, but kept attracting more interest and selling out.

What surprised me most was how young everyone was. Vince, Nick and Verlaat are all under 30 years old, and they were able to attract an audience of about 100 young founders.

The experience 

The event was at the Castelfalfi resort in the heart of Tuscany, Italy. The village of Castelfalfi was a five-minute walk from the hotel and featured a row of shops ranging from a clothing store to a gelato shop. Everywhere I looked, there were scenic views. 

Event participants paid $14,000 for five-star accommodations, meals and airport transfers. Attendees had to apply and have a proven track record of leading a seven- to nine-figure brand.

Besides the three OOAK founders, speakers at the event included Jeff Srithongrung, director of creative strategy at TubeScience, and Ray Jang, founder and CEO at AI ad company Atria. Srithongrung spoke about how to run an effective ad campaign and the benefits of changing an ad to appeal to different audiences. Jang spoke about the transformative effect of AI in advertising and said that AI has reduced the cost of testing concepts and trying new things to “close to zero.”

On Saturday afternoon, I joined the conference participants for a truffle-filled lunch: We had beef tartare with truffle as a starter, truffle risotto for the main course and vanilla truffle mousse for dessert. I sat with founders working on selling everything from supplements to gold. 

One attendee spoke about his success

Most event participants were brand founders. One speaker, 32-year-old Alvaro Gellings, revealed that he built an apparel brand and sold $1.4 million worth of products within the first hour of launch. He then built a sportswear brand called Day One and tapped into a partnership with German creator and endurance athlete Arda Saatçi. Gellings, who was also an attendee at the conference, knew that selling sportswear required more than just having a quality product. 

“Nobody’s looking for the next gym tank to buy,” he says. “Nobody’s in urgent need of the next T-shirt, the next socks, the next shoes. You have to create a story.”

Gellings created a highly publicized story: Saatçi would run 1,960 miles from Berlin to New York. 

He would start in Berlin and run across Europe to Porto, Portugal, then take a flight from Porto to Boston. For the final stretch, he would run from Boston to New York. He would do it all while wearing Day One sportswear, and the company’s official launch would be tied to him completing his run.

It took Saatçi 74 days in 2024 to complete the task. The ad campaign had “everyone posting,” Gellings says. It was a prime example of how companies can leverage partnerships with influencers to make their brands more recognizable and focus on the story, not the product. 

Framing products in new ways

The OOAK co-founders hosted a number of talks at the retreat, and I sat down with the trio before the event started to hear more about their entrepreneurial journeys.

Even if you don’t know OOAK, you may recognize one of their portfolio brands, like earplug company Hears and sleepwear startup Dore & Rose. Verlaat, Nick and Vince founded Dore & Rose in 2022, followed by Hears in 2023 and subsequently grouped the businesses under the holding company OOAK.

Verlaat oversees brand, creative direction and positioning while Nick handles product and people and Vince focuses on growth, paid acquisition and supply chain execution. 

“We all had a very separate skill set [when we started], and we still have [that],” Verlaat says.

He added that his blueprint for launching brands, his core thesis, was to take a “boring” product and frame it differently. For example, the founders position Dore & Rose as a premium sleep-wellness brand rather than a conventional bedding retailer, selling mulberry-silk sleep products infused with silver ions. They emphasize overnight skin recovery and restorative sleep.

The founders took a relatively familiar product, the silk pillowcase, and pushed it toward an emotionally richer category: beauty, wellness and sleep quality. It’s a silk pillowcase brand positioned as beauty, not bedding. 

Hears applies the same playbook to hearing protection: It sells earplugs for music, nightlife and event environments but positions them as a premium lifestyle product rather than a mere accessory. Its public narrative is about enjoying music clearly and confidently while protecting hearing. The founders repositioned the earplugs as a fashion product, not a medical device.

The outcome

So far, the way they market their products is paying off: The founders disclosed that OOAK Brands is making a combined yearly revenue of $100 million. They are targeting $200 million this year. 

In addition, they have sold over one million silk items through Dore & Rose and have placed their silk products in 50 five-star hotels, like Four Seasons, Belmond and Cheval Blanc. Dore & Rose has partnerships with over 150 retailers, including Nordstrom, Mecca and Namshi.

Meanwhile, Hears hit $7 million in revenue in its first year, 2024. Since then, the brand has sold more than 250,000 pairs of earplugs. Hears partnered with the Hearing Health Foundation to donate a portion of revenue and raise awareness for hearing protection. 

Their advice

Verlaat’s advice for potential founders waiting to make the leap is to “just do it.” “What’s the worst thing that could happen, really?” he says. “You don’t die.” 

He says that he knew from the start that he would succeed. “We always believed that we’re going to get to where we are today.”

Vince pursued entrepreneurship because he “wanted to work and make money.”

“I wanted to just go harder,” he says. “For me, I think I figured out really, really soon that working for a boss was not going to cut it for me.”

Nick was candid that founders needed to “wear multiple hats,” especially in the early stages of building a business. He is also an advocate of just getting started, even if a founder doesn’t have everything figured out. “You don’t need to see the finish line. You don’t need to know where it will end,” he says. “As long as you know your next step, eventually you will get there.”

I first saw the hotel Castelfalfi from the back of a cab, its stone exterior rising out of the Tuscan hills. Inside waited founders who collectively generate more in annual revenue than some small countries — and each had paid thousands of dollars for the privilege of being there.

On paper, I had no business being at a $14,000 retreat for seven- to nine‑figure founders in Tuscany. I don’t run a massive consumer goods brand or a unicorn startup, and my net worth is far from impressive. But when I was invited to sit in on three days of keynote sessions and fireside chats at the OOAK Mastermind conference, I couldn’t turn down the chance to see what happens when ultra‑successful founders gather behind closed doors.

OOAK Mastermind was hosted by OOAK, short for One Of a Kind. The global consumer brand-building company creates, scales and acquires brands.