Howard Katkov: CEO, Dirtbag Skier, & Leader

On this episode, Kevin chats with Howard Katkov, CEO and co-owner of Red Mountain Resort in Rossland, British Columbia, about his 45 consecutive years pulling a steady paycheck from seven different companies he's started and successfully operated. Howard shares his love for the game of business and building successful ventures from vision to execution with strong teams, exploring how you don't always have the luxury of confidence in decision making yet still need to lead. The conversation emphasizes the critical importance of truly understanding the risks in real estate deals, especially regarding time required to properly execute—accepting a mismatch between the deal and investor timelines is a recipe for trouble, making patient money and autonomy essential to secure upfront. Howard discusses being a rule breaker rather than a rule maker, balancing the interests of capital and community while being a steward of both, and his conviction that pound for pound there's no better ski location in North America than Red Mountain. They cover building teams as a partner rather than a conventional top-down boss, removing inter-departmental communication walls, choosing investors carefully, empowering younger team members to influence company direction when they reflect your target market, possessing active humility to listen and observe, and looking back to learn instead of looking back with regret.