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.

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 through this and the other Unreasonable initiatives so far.

Going Public

Jeff worked closely with Jay Walker, the founder of Priceline and one of the most patented entrepreneurs to help bring the company public. In working with Jay, Jeff discovered the three core buckets of people needed as an entrepreneur: Inventors, Builders and Operators. Inventors come up with brilliant IP and patents and the builders come in and create companies out of IP. This eventually paves the way for operators to come in and run the organization as it becomes public.

Similar to my Ted Talk about Spotters, Planners, Builders and Sustainers, Jeff used his concept when he was the CEO of uBid, aggregating demand for products with unsold inventory, mirroring the model of selling empty airline seats and hotel rooms through Priceline.

Most Dangerous Words Business

The three most dangerous words for a company are “we’re doing fine.” Those companies are often ignore innovation and are too comfortable. I refer to these types of companies as “big, fat, slows.” They are at times on the verge of irrelevance, obscurity or decline and often not aware of it. To break this cycle, it is up to leaders to act with a renewed sense of urgency and start thinking innovatively again.

Becoming a Better Entrepreneur  

Instead of having people asking about your experience, let your work speak for yourself. For new entrepreneurs just starting out, don’t let people question your credibility. Stop trying to sell yourself and instead focus on what your product or service offers. For example, when he was first starting out, Jeff created airport check-in kiosks. In bringing these kiosks to airports across the county, Jeff ignored specific results and turned all of his focus to making customers happy. Whenever people questioned his credibility, he turned to a video of happy customers in airports, which led to an quicker sales.

Next, in order to get people to work with you, Jeff advises that you stress happiness as one of the main parts of the equation. He starts off conversations by asking prospective employees what matters to them, what they want to do in life and how they want to make a long-lasting impact on the world.

To hear more about Jeff’s perspective on entrepreneurship and scaling up businesses, watch or listen here, or wherever you listen to podcasts.

About the Reboot Chronicles Podcast

Hosted by Dean DeBiase. The Reboot Chronicles is a popular no-holds-barred podcast on iHeart Radio, iTunes, Spotify, Google Podcasts, and YouTube that has been bringing together CEOs, entrepreneurs, authors, and global leaders, for over a decade, to discuss how organizations are rebooting their leadership-competitiveness of everything from growth, innovation, and technology to talent, culture, and governance. Tune in wherever you listen to podcasts or at

About Dean DeBiase

Named a Growth Guru" by Inc. Magazine, Dean DeBiase is a Faculty Member at Kellogg School of Management and Silicon Valley serial CEO, where he has served in chief executive and chairman roles of more than a dozen emerging growth companies, CEO of Fortune 500 subsidiaries, and a director on public, private, family-enterprise, CVC, PE and VC boards. He is a Technology Fellow at Northwestern University, a Board Leadership Fellow at The National Association of Corporate Directors, and an Advisor to the National Science Foundation. A Forbes Contributor and co-author of the best-selling book The Big Moo, Dean, is working on his next book, Dancing with Startups. Connect with Dean here: