On this episode of High Stakes with Steve Rozenberg, Steve talks with Jackson Wyne Mason, owner of a construction company and founder of Crew Glue, a business built to help contractors estimate faster and more consistently. Jack's path started as a young employee at a general contracting company in Minnesota, where he was surprised by how chaotic the day-to-day operations really were. Instead of walking away, he leaned in, leaving that job to work as a carpenter for one of the GC's subcontractors so he could understand construction from the ground up, while building estimating systems for contractors on freelance platforms at night. Jack opens up about the brutal early stretch of building his business: piling up credit card debt at 19 years old, living out of an Extended Stay America, and one specific night stuck at an all-night Perkins in Minneapolis during a snowstorm with no gas and bad tires, unable to leave until he made a sale. That moment became a turning point in how he thinks about business, sales, and what it actually takes to push through the parts of entrepreneurship nobody glamorizes. The conversation moves into how Crew Glue works, serving contractors in the one to ten million dollar range by systemizing the thought process of an experienced estimator into a repeatable, consistent template rather than just handing over more software. Jack and Steve also dig into where AI is genuinely useful for contractors versus overhyped, why structure and consistency will matter more than technical know-how going forward, and the damage well-meaning people can do when they don't believe you can pull something off. Jack closes with a hard truth for anyone starting out: the biggest obstacle usually isn't other people's opinions, it's letting the doubts of people closest to you become the ceiling on what you believe is possible for yourself. Conect with Jackson: LinkedIn: https://www.linkedin.com/in/jwmason/ __________________________________ https://steverozenberg.com/ __________________________________ Steve Rozenberg, originally aspiring to be an international pilot, navigated a challenging shift in his career trajectory when the 9/11 attacks jeopardized his pilot career. Turning adversity into opportunity, he embraced his entrepreneurial spirit and transformed his situation into a multimillion-dollar success story. As the proud owner and founder of The Rozenberg Group, an esteemed international consulting firm, Steve is dedicated to helping clients achieve their goals and regain control of their time and freedom. Beyond his role as a successful entrepreneur, Steve is renowned for his dynamic keynote presentations. He delivers motivational and inspiring speeches that resonate with audiences, providing actionable steps, business systems, and a roadmap to success. His direct yet hopeful messages engage audiences both mentally and emotionally, instilling a positive outlook and guiding them toward success in various aspects of life. Despite facing an unimaginable tragedy on March 6th, 2023, with the loss of his beloved son Jett in a motorcycle accident, Steve demonstrated an indomitable spirit. In honor of Jett’s remarkable life, filled with global adventures, martial arts, music, and inspiration, Steve and his wife Renee established the LIVE LIKE JETT SCHOLARSHIP FUND. Learn more: livelikejett.org This scholarship fund serves as a tribute to Jett’s legacy, encouraging others to embrace life fully and persistently pursue their dreams. The fund specifically supports high school students seeking to enter the trade industry, mirroring Jett’s passion as a welder. Currently, Steve Rozenberg channels his extensive experience as a successful real estate investor to mentor and guide individuals toward prosperity. Despite the challenges he has faced, Steve remains committed to inspiring, uplifting, and creating a positive impact on the lives of those around him. ➤https://www.facebook.com/SteveRozenberg1 ➤https://www.instagram.com/rozenbergsteve _______________________________________________________________________ #SteveRozenberg #TwoDayTakeoff #Opportunity #ChangeYourLife #Entrepreneur #LiveLikeJett #FinancialFreedom