From customer support to CEO, Maarja Pärt built Yolo Group by embracing risk, speed, and transparency
When Maarja Pärt joined Yolo Group, it wasn’t yet Yolo. It was a small team building Bitcasino – the world’s first licensed crypto casino – at a time when Bitcoin was still largely experimental. A decade later, Yolo Group is a diversified global organisation of over 1,000 people, operating at the intersection of fintech, gaming, and Web3. In a full-circle moment, the company has even expanded into physical spaces with the launch of Bombay Club – a luxury casino and hospitality concept in Tallinn’s Old Town, bringing the brand’s digital roots into the real world.
Maarja’s own journey mirrors this evolution. She started in customer support. Today, she leads the group as CEO.
In this episode of the Winning Friends podcast, Maarja reflects on the realities of scaling at speed – hiring fast, breaking things often, and rebuilding just as quickly. From navigating imposter syndrome in the C-suite to turning poor long-term planning into a competitive edge, she shares an honest take on what it means to lead through volatility.
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Growth at Yolo was relentless. At one point, the company was onboarding one new employee every single day, sustained over a two-year period. That level of recruitment came with both logistical and cultural challenges. Maarja recalls how things started breaking once they hit 300 people: “We realised we needed to restructure, split into smaller teams, and rethink the way we train.”
For Bombay Club, one of Yolo’s brands in the luxury gaming space, every team member was hired two months before launch to allow for proper onboarding. That level of preparation is rare in the hospitality sector in Estonia, and it reflected a shift in approach from speed to intentionality.
As Yolo grew, Maarja remained directly involved in recruitment. Her approach was intuitive: “You can see it in their eyes within ten seconds. If they have that spark, you know.”
She prioritised potential over pedigree, often hiring junior candidates and developing them internally. That mindset proved essential for building Yolo’s high-performance culture – a place where not everyone fits, but those who do, thrive.
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Strategic planning, in the traditional sense, has never been Yolo’s strong suit. “We’ve always been bad at it,” she admits. But in industries defined by volatility – crypto, iGaming, and finance – that has often played to their advantage.
The industry moves fast and their ability to move with it, to spin up new business models and shut down what doesn’t work, has been key to survival. Over time, the company formalised this agility by separating teams by function, giving product development and R&D more autonomy to experiment.
Pärt became COO in her mid-20s, leading teams older and more experienced than herself. Imposter syndrome, she admits, “was basically my second name.” But rather than pretending otherwise, she chose to speak openly about it.
“A bit of self-doubt is healthy – it keeps you from becoming overconfident,” she says. Her approach to leadership is grounded not in bravado but in transparency. She believes that sharing insecurities and leaning on others is a strength, not a weakness.
“There’s this idea that being a CEO is lonely,” she adds. “I disagree. If you’ve built the right environment, it doesn’t have to be.”
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Winning Friends is a podcast powered by Estonia’s e-Residency, hosted by Logan Merrick and Dylan Hey. Each episode explores how real relationships – with co-founders, teams, or even imposter syndrome – shape the way we build. This conversation with Maarja is no different: a story of culture under pressure, risk embraced, and teams built fast but held together by trust.
Want to dig deeper into how global entrepreneurs are building borderless businesses? Don’t miss our article on Estonia’s e-Residency programme – a way for founders around the world to launch, run, and scale companies with European access, no matter where they live.
Watch the full episode of Winning Friends featuring Maarja Pärt below.
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