Serial CEO and entrepreneur Jeff Hoffman has had his hands in a number of different ventures, including Priceline, a Grammy-winning jazz album, an Emmy Award-winning television show and a best-selling book. On this episode of the Reboot Chronicles, I spoke with Jeff about 1871, the travel industry, helping entrepreneurs, the current financial craze of SPACs and crowdfunding and how to successfully scale your business.

Inspired by 1871

As the chairman of the Global Entrepreneurship network, Jeff’s focus is to create ecosystems for entrepreneurs in any geography and ecosystems, allowing for a breadth of experiences and backgrounds. Jeff was inspired early on by our Chicago-based incubator 1871, ranked the top global business incubator, with over $1 billion of funding associated with the member companies since inception. We have various corporate and entrepreneurial programs, with hundreds of startups and DEI initiatives for women, Hispanics, African-Americans, Veterans and Neighborhood Accelerators. Jeff and the Global Entrepreneurship team are also focusing on initiatives for female entrepreneurs and minorities, ensuring that they have the resources to succeed and grow their companies.

The Art of Scaling

Jeff and I have been deeply involved in scaling businesses, which led to an interesting conversation about how every startup is different. It’s not enough to provide generic advice to an entrepreneur—you need to assess the business, people and market to give advice situationally. While some might need examples of how to pitch investors, others might require direct funding and scaling help. As scalers, we exist to create the experiences and space that early stage, growth stage and corporate innovators need while they build extraordinary businesses.

Unreasonable Expectations

Working with one of his mentees, Daniel Epstein, Jeff’s involved in the Unreasonable Group, which was named after the George Bernard Shaw quote that reasonable people adapt to the world around them, while unreasonable people expect to adapt to them. The idea behind the group is that entrepreneurs are the people most likely to solve the world’s biggest problems, so they focus on social entrepreneurship. To play into the idea of being “unreasonable,” the team spent over 100 days on a research ship, dedicating different boat decks to various initiatives. For example, the fifth deck was an incubator, where mentors would meet with entrepreneurs and help them grow their start-ups—sounds like the area I’d hang out in!

Mentors would join the ship as they circumnavigated the globe, creating a collective of investors that companies could tap into for all aspects of their growth strategy. While this might not have been your traditional cruise ship, participants enjoyed themselves, and over $4.5 billion was raised though this and the other Unreasonable initiatives so far.