Sea2Sky Investments is a Whistler-based partnership acquiring well-run service businesses from owners ready for their next chapter.
We're operators, not a fund — local, hands-on, and in it for the long term.
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Between us we've founded and exited companies, led hundreds of strategic planning engagements, and built the back-office systems that keep small businesses running smoothly.
Sea2Sky Investments exists to acquire well-run service businesses from owners ready for their next chapter — and to grow them the way we've grown our own.
We're not deploying a fund on a clock. We aim to close one or two acquisitions a year, and only when the business, the owner, and the fit are right. Quality over pace, always.
Most of the business owners we know built what they have over decades. We treat transitions with the care they deserve — honest conversations, fair valuations, and transition plans that protect the team, the brand, and the legacy.
We live here. We know the corridor. After acquisition, we're actively involved in strategy, systems, and leadership — not just writing cheques from a spreadsheet somewhere else.
Kelvin grew up on a family farm in southern Manitoba and has spent the last decade building service businesses in Whistler and the Sea to Sky corridor. He co-founded and sold a property management company, scaled Sierra Window & Property Services into a profitable brand now in a planned exit, and currently runs Summit Hospitality, a premium cleaning and property services company built for Whistler's nightly rental market. Based in Whistler with his wife and family.
Chad is the General Manager at TradeBrain, where he leads back-office operations support for trades and small service businesses across Canada. His work is turning day-to-day chaos into predictable growth — building the processes, checklists, and accountability systems that let operating businesses run smoothly without the owner in every email. He believes work should be fun, kind, and intentional. Based in Pemberton.
Tim is the founder of The Lief Group, a boutique consultancy based in Whistler providing strategic planning, executive coaching, and fractional COO and CFO services to owner-led businesses. Over the last several years he's worked inside dozens of companies across services, retail, food, and professional sectors — diagnosing what's actually driving performance, aligning leadership teams, and installing the operating cadences that make growth repeatable. Based in Whistler with his wife Briar and their family.
If you've built something worth protecting and you're starting to think about what comes next, we're a good first conversation.