Running a US Real Estate Fund From a Costa Rica Surf Town | Sarah Miskelly

How do you run a US real estate fund, SEC-regulated, entirely US-based investors, from a surf town in Costa Rica, and still turn down most of the deals you're offered?Sam sits down with Sarah Miskelly, founder and fund manager of Hylee Capital, a firm that helps accredited investors access carefully selected US real estate and alternative investments. Sarah grew up in her family's real estate business in Toronto, built a multi-six-figure brokerage, and then walked away from it at its peak, burned out and planning an exit from the start. She'd been quietly investing as an LP on the side, so she shut the brokerage down, moved her family to Costa Rica, and rebuilt as a fund manager she can run from her laptop. To date, Hylee Capital has deployed over $16M alongside roughly 100 investors.In this conversation:The full origin story, from managing family multifamily properties to running a fundWhy she walked away from a multi-six-figure brokerage business at its peakWhat relocating a family abroad actually costs, and why "it's cheaper" is a mythWhether managing capital remotely helps or hurts credibility with investorsDiversifying across verticals and the capital stack, not just asset classesMatching deals to an investor's actual buy box and stage of lifeWhy fund-manager compensation weighted toward exit keeps interests alignedWhat real due diligence looks like: underwriting, whisper networks, background checksThe large-name sponsor deal she passed on, and what the capital stack gave awayWhy she turns down almost everything sent to her inboundHer one piece of advice for relocating and for breaking into the space: bet on yourselfTopics covered: real estate, fund management, private real estate, due diligence, capital stack, preferred equity, common equity, LP investing, portfolio diversification, alternative investments, accredited investors, real estate syndication, passive income, relocating abroad, Costa Rica, expat life, lifestyle design, women in finance, private marketsGuest: Sarah Miskelly, Founder & Fund Manager, Hylee Capital | https://hyleecapital.comNewsletter: https://www.mechanicsofmoney.coWebsite: https://silvermancapital.comSubscribe for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth.#realestateinvesting #fundmanagement #privatemarkets #alternativeinvestments #duediligence #accreditedinvestor #mechanicsofmoney #lifebydesign #passiveincome #wealthbuilding