21st Century Entrepreneurship

Scott Oldford is a lifelong entrepreneur who built his first seven-figure business at 16, and we spoke about what happened when decades of entrepreneurial instinct collided with an identity he was trying to force. By 2022, he was making roughly $7 million a year at a 70% profit margin while working 15–20 hours a week. Then he chased a bigger identity and a $100 million outcom...

Denis O'Shea is the founder and CEO of a technology services company, and we spoke about how a painful sales failure became the foundation for 22 years of helping organizations extract more value from technology. Early in his career at Nokia, a customer challenged him on why they should buy more technology when employees barely used what they already had. Denis says that conv...

Jonny Price is President of WeFunder, and we spoke about why startup investing should no longer be reserved for millionaires—and why founders may be overlooking one of their strongest sources of capital: their own customers. He explains how changes in U.S. regulation opened private investing to everyday people and why that shift creates opportunities not only for investors, b...

Kim Butler, Prosperity Thinkers founder, is a financial educator with more than 30 years of experience in banking, investing, and insurance, and we spoke about why strong earners often build wealth in the wrong order. Her starting question is direct: “You’re awesome at making money. How much of it are you keeping?” Rather than beginning with investment products, she helps ent...

Mike Ryan, BPN CEO, is a former Goldman Sachs analyst who later ran its global equity business and managed Harvard’s $18 billion endowment, and we spoke about why powerful AI still fails investors when its answers cannot be trusted. After repeatedly receiving polished but incorrect information from generic tools, he decided to develop a more reliable approach. As he puts it, ...