Scot Chisholm - CEO, Founder, and Investor

Be fierce with the fierce. Scot Chisholm is a four-time founder with over 20 years of experience in building and leading companies. He founded Classy, which he scaled to over $100 million in revenue and led significant strategic investments and acquisitions, including the sale of Classy to GoFundMe in 2022. Currently, Scot is building Highland, a private accelerator and community designed to support and elevate startup CEOs and founders. In his conversation with Ryan, Scot highlights some of the key moments throughout his journey as a leader, with the theme of resilience at the forefront of his story. Scot speaks on the value of having a co-founder when starting a company, and also gives his opinion on the importance of friendship and family in business partnerships. The two also discuss the concept of “speed to truth” when trying to resolve difficult conflicts, and Scot explains some of the successful strategies he’s implemented at his organizations to make sure all employees are heard and valued.