Markus Frind, the plentyoffish guy comes to mind. Bootstrapped the biggest dating site in the US with zero employees or VC, and sold out for $500m around ten ye

Markus Frind, the plentyoffish guy comes to mind. Bootstrapped the biggest dating site in the US with zero employees or VC, and sold out for $500m around ten years ago. He runs a winery now. https://www.frindwinery.com/Our-Story/Our-Team/Markus-Bio https://www.frindwinery.com/Our-Story/Our-Team/Markus-Bio https://www.businessinsider.com/how-markus-frind-bootstrapped-plentyoffish-and-sold-it-for-575-million-2015-7?op=1 https://www.businessinsider.com/how-markus-frind-bootstrappe...