After nearly three decades of building companies, Gerald Heydenreich speaks less about success and more about judgment, timing, and the discipline to face what is not working.

Gerald Heydenreich did not begin his career as a founder. He started inside a large corporation and was asked to leave within a year. The experience made one thing clear. He was not suited to corporate life. In 1999, he started his first company, just as the internet was becoming commercially usable.

The business was a B2B software platform, an early version of what would later be called SaaS. At the time, it was known as an application service provider model. The company grew quickly. By its second year, close to a billion dollars in transactions were moving through the platform, and an IPO was planned.

Then the events of September 11 changed everything. The IPO collapsed, funding disappeared, and the company went bankrupt. Heydenreich describes this period as his first real lesson in resilience. The team was cut from 120 people to 20. Offices were shut down. The business was rebuilt slowly into a simpler software company and eventually sold in 2006.

His next venture, BuyVIP, was an ecommerce marketplace offering discounted branded products to a large member base. The timing was right. Ecommerce was growing fast, and BuyVIP scaled with it. By 2011, the company had around 350 employees and annual sales of about 130 million dollars. When Amazon expressed interest, Heydenreich chose to sell. He had learned from his earlier experience that waiting too long can be costly.

After taking a year off to travel, he returned to build another company, this time a social selling business. The company produced jewelry, cosmetics, and accessories and sold them through a network of independent salespeople. The goal was to support first-time entrepreneurs and show a more realistic picture of what building a business involves. The company faced several challenges, including operational and quality issues, and was sold in 2019.

Around this time, Heydenreich became deeply interested in blockchain and later AI. He began investing in early-stage projects and eventually built a venture studio focused on AI, Web3, and businesses at the intersection of both. He works closely with founders, often at the idea or prototype stage, and is involved in strategy, fundraising, and early execution.  In 2022 he founded EtherMail, a Web3 email communication platform that bridges the gap between Web2 and Web3 by giving users full ownership, control and sovereignty over their inboxes.

Across all his ventures, his views on entrepreneurship have become very clear. Every company needs one person who is fully committed and driving it forward. Teams matter, but they form later. Without a clear driver, companies stall. Most failures, he believes, come down to three reasons. Either the founder is no longer the right person for the stage of the company, the team is not working well together, or there is no real product market fit.

Watch the intervew on YouTube here.