#63 Jon Staenberg: Investing in Startups, Venture Funds & Search Funds

John took Nataraj through his early days growing up in Omaha and attending Stanford University, where he was inspired by the culture of creativity and trying new things.

After graduating, John worked in real estate and then got his MBA, also at Stanford. He became fascinated by the nascent world of venture capital and startups in Silicon Valley.

John landed a job at Microsoft in the late 1980s, when the company was still small and growing fast. He described the exciting “change the world” energy there, where people worked tirelessly to spread personal computers.

After Microsoft, John started his own venture funds focused on bridging Seattle and Silicon Valley. He's been involved with around 200 startups over his venture career.

John reflected on missing out early on companies like Google and Amazon that became huge wins. But he's also had some big successes, like Seagate. He emphasized that surprise and timing are always at play in VC investing.

Nataraj and John also discussed how venture capital has matured and become overcrowded, making it hard to generate outsized returns. So John has pulled back on direct startup investing.

Pivoting gears, they talked about John's passion project - starting a wine business in Argentina 17 years ago. He saw it as a way to pursue his interests and bring people together.

John then explained his latest venture to Nataraj - launching a search fund to invest in other funds that acquire small businesses for entrepreneurs. He believes this model can provide great returns and opportunities.

Throughout his wide-ranging career, John has stayed focused on connecting people and giving back, including through the many events he has hosted.