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HUSBAND AND WIFE BUSINESS, BUILT TO SAIL

Ryan O’Leary & Kristin O’Leary
ft. Ryan O’Leary & Kristin O’Leary

Ryan and Kristin O’Leary, husband and wife co-founders of Sonapay, join Raman Sehgal to unpack how they built, scaled, and sold a bootstrapped Canadian payments business. They explore the risk of going all in with four kids at home, the power of residual revenue and values-led selling, the reality of burnout and earn-outs, and how a dream written into their wedding vows became the compass for life after the exit.

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IN THIS EPISODE

In this episode, Raman Sehgal sits down with husband and wife team, Ryan and Kristin O’leary.

Ryan is the co-founder and former CEO of Sonapay (SONA), a Canadian merchant services company he built from scratch in Bedford, Nova Scotia in 2016. Over eight years, bootstrapped and values-driven, SONA grew to serve 5,000 merchants across Canada, processing over $1B in annual volume with industry-leading retention rates and a culture built on transparency and solution selling. In 2024, SONA was acquired by Celero Commerce. Ryan is now the founder of ROKO Holdings and Investments, deploying capital into fintech, venture, and early-stage companies. He and his wife Kristin are preparing to circumnavigate the globe aboard their Oyster 625, Distraction, in the 2028 Oyster World Rally — a dream that was literally written into their wedding vows 19 years ago.

LinkedIn: https://www.linkedin.com/in/ryanoleary1/
Kristin is the co-founder and former COO of Sonapay (SONA), where she built and ran the operational engine behind one of Canada’s most respected merchant services brands. A CAIB-certified insurance broker turned entrepreneur, Kristin previously acquired and successfully exited her own business before joining SONA full time. She is the integrator to Ryan’s visionary — the steady hand who kept the business, the family, and the mission on track through eight years of bootstrapped growth. She is now co-steering the family’s next chapter, including a global sailing circumnavigation in 2028.
LinkedIn: https://www.linkedin.com/in/kristin-o-leary-34176115b/
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WHAT WE COVER

  • Leaving a stable day job with 4 kids at home, betting on a values driven approach to payments built on transparency and trust
  • Building a residual revenue model that compounded over time to create a scalable distribution engine
  • Designing an agent model that rewarded people fairly, created loyalty, and became a self sustaining fintech brand
  • The reality of founder burnout, and why what got them here would not get them where they wanted to go next, hence the deal
  • Running a tight, targeted sale process by preparing 2.5 years in advance, then generating multiple LOIs fast with only 5 acquirers approached
  • Navigating the emotional complexity of staggered earn outs, including resentment, identity shift, and rebuilding routines after the exit
  • The long term pull that anchored their decision making, a 2028 Oyster World Rally circumnavigation that was literally written into their wedding vows, plus a foundation focused on care and youth at risk

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