Imagine you are running one of the top five programs of your kind in the entire world. You have the prestige, the history, and the brand recognition, but you realize that despite all that success, you are actually stuck. You’re competing against giants with more resources and more scale, and you can see a “gradual decline” on the horizon if you keep doing things the traditional way.
Our guest today faced that exact existential crisis. He was handed a blank sheet of paper and asked: if you can’t be number one where you are, where can you be number one?
By turning the problem on its side and making a bold move away from his original core service, he didn’t just survive—he redefined an entire industry category and secured a new path to the top.
Welcome to today’s episode of Your Business Growth Podcast. I’m your host, Jeremy Shapiro, author of Your Business Growth Playbook, and my guest today is Andrew Ackerman.
About Andrew Ackerman
Andrew Ackerman is a serial entrepreneur turned early-stage investor and innovation expert who has invested in over 70 startups over the past two decades. He currently serves as the Strategic Advisor and Head of REACH Labs for Second Century Ventures, the venture capital arm of the National Association of Realtors. In this role, he consults on innovation strategies for corporate venture funds, accelerators, and venture studios, while also sharing his expertise as an adjunct professor of entrepreneurship.
Previously, Andrew was the Managing Director at Dreamit Ventures, where he was instrumental in launching and building both their Edtech and Urbantech (Proptech and Construction) verticals. His extensive leadership background includes serving as the founding CEO of Layercake.com and managing a family office where he incubated new ventures while overseeing more than $50M in hedge, private equity, and venture capital funds.
Andrew’s foundational entrepreneurial experience was built over eight years as the founding COO of Bunk1, where he grew the company from scratch into the leading web services provider for the summer camp industry. Prior to that, he contributed to the digital evolution of the education sector at Kaplan, helping transition their traditional classroom test prep services into successful online products.
A prolific thought leader, Andrew has published over 60 articles for major publications including Fortune, Forbes, and AlleyWatch. He is also the author of the book The Entrepreneur’s Odyssey, a unique work described as a textbook disguised as a novel that details the realities of taking an idea to a funded startup. When he isn’t mentoring startups or managing investments, he brings his killer research and critical thinking skills to the classroom to help the next generation of founders.