BIO: David Siegel is a Silicon Valley entrepreneur who has founded more than a dozen companies. He has written five books on technology and business, was once a candidate for the dean of Stanford Business School, and is now an AI thought leader leading an AI startup he hopes will pave the way for the agentic economy.

STORY: David invested heavily in launching a longevity coaching business, believing people would pay to extend their lives through lifestyle change. Despite strong science, personal results, and significant marketing spend, demand proved nearly nonexistent.

LEARNING: A great idea without real demand is still a bad investment.

David Siegel is a Silicon Valley entrepreneur who has founded more than a dozen companies. He has written five books on technology and business, was once a candidate for the dean of Stanford Business School, and is now an AI thought leader leading an AI startup he hopes will pave the way for the agentic economy.

After years of building companies and studying major technological shifts, David found himself pulled deeply into the longevity movement. This wasn’t casual curiosity. He read more than 20 books, radically transformed his lifestyle, and developed a deep understanding of insulin resistance, nutrition, exercise, and long-term health.

The results were personal and visible. David was fit, disciplined, and energized. The idea that science could help people live 10 to 15 years longer, with a higher quality of life, felt not only possible but urgent. Helping others do the same seemed like a natural next chapter.

Confident in both the science and his own experience, David decided to turn longevity coaching into a scalable business. His target audience was people in their 50s and 60s, individuals who were pre-diabetic or heading toward serious health issues and stood to benefit the most from early intervention.

He approached the venture like a seasoned entrepreneur. He built funnels, ran Facebook ads, spoke at retirement communities, and spent months on discovery calls explaining how lifestyle changes could dramatically reduce the risk of cancer, Alzheimer’s, and diabetes.

This wasn’t guesswork; it was disciplined execution.

Then reality set in.

Despite spending over $100,000 on advertising and investing countless hours in conversations, demand was almost nonexistent. People listened. They nodded. They agreed the logic made sense. Then they walked away.

Many believed the healthcare system would save them. Others hoped for a pill instead of discipline. Even those clearly facing insulin resistance weren’t willing to make sustained lifestyle changes.

The most sobering realization wasn’t about marketing or pricing. It was this: most people don’t actually want to live longer if it requires consistent effort.

In the end, only about one percent of the people David spoke to were already doing the work and didn’t need coaching. Everyone else opted out, fully aware of the consequences.

The investment failed not because the science was wrong, but because the market wasn’t there. David ultimately gave the information away for free and walked away from the business, having learned an expensive but clarifying lesson about belief versus demand.

BIO: Jon is the Founder and CEO of FranBridge Consulting, a 2-time Inc. 5000 company, and he is a top 1% franchise consultant.

STORY: Jon co-founded a marketing and call-center business that appeared successful on the surface, growing to millions in revenue and dozens of employees. However, excessive customization and an inability to charge prices that matched rising costs meant the business never became sustainably profitable.

LEARNING: Profitability is oxygen. Knowing when to admit you’re wrong matters just as much as knowing how to start.

Jon Ostenson is the Founder and CEO of FranBridge Consulting, a 2-time Inc. 5000 company, and he is a top 1% franchise consultant. Jon is also the author of the bestselling book, Non-Food Franchising. Jon draws on his experience as a former Inc. 500 Franchise President and Multi-Brand Franchisee in helping his clients select their franchise investments.

Leaving the corporate world felt like freedom. After years of structure, predictability, and steady paychecks, you finally get to build something of your own. That was precisely where Jon found himself: grateful for his corporate experience, energized by the idea of business ownership, and eager to prove he could create something meaningful on his own terms.

Shortly after leaving corporate life, Jon partnered with a colleague to launch a marketing and sales company. He owned 60 percent of the business and ran day-to-day operations, while his partner held the remaining 40 percent.

The vision was compelling. The company would help franchise businesses grow by handling their marketing, answering inbound calls through an in-house call center, and booking appointments directly for clients. The promise was simple: make the phones ring and convert those calls into revenue.

At first, it worked. The business grew quickly, attracting a strong leadership team and building a culture Jon was proud of. With around 35 employees and annual revenues of $3 million to $4 million, the company appeared successful from the outside. The team was energized, clients were signing on, and the pace was exciting.

But beneath the surface, there was a quiet, persistent problem.

The business wasn’t profitable.

Despite all the effort, the long hours, and the constant tweaking, the company hovered around breakeven. Some months it lost money. Others it barely scraped by. Payroll was always looming, and profitability felt just out of reach. Jon tried adjusting pricing, shifting emphasis between marketing and call center services, and introducing new technology to increase value.

But every fix only delayed the inevitable question he didn’t want to answer: What if the model itself was broken?

The core issue turned out to be customization. The business was designed to scale by serving franchise systems with repeatable processes. Instead, each franchisee insisted their market was different, their staff was unique, and their customers required special handling. Wanting to please early clients and drive revenue, Jon said yes. Again and again.

Over time,...

BIO: Edwin Endlich is the Chief Marketing Officer of Wysh and President of the National Alliance for Financial Literacy and Inclusion.

STORY: Edwin’s worst investment was buying Tilray stock at $143 during the early hype of legal cannabis investing. Swept up in the excitement of a “new frontier,” he held on as the price crashed—eventually selling at around 30 cents and losing over 99% of his investment.

LEARNING: The fundamentals always apply, even in new or exciting industries. Don’t let hype replace due diligence.

Edwin Endlich is the Chief Marketing Officer of Wysh and President of the National Alliance for Financial Literacy and Inclusion. Edwin has spent his career at the intersection of marketing, fintech, and AI, helping financial institutions tell more human stories in an increasingly digital world. He’s passionate about making financial protection simple, accessible, and even a little more fun — proving you don’t need buzzwords or hype to make banking and technology relevant.

There’s nothing quite like the rush of feeling early—early to a trend, early to a movement, early to a once-in-a-lifetime opportunity. That’s precisely what Edwin felt in 2015–2016, when investing in legal cannabis became possible in parts of the United States.

For the first time, regular people could invest in a newly legalized industry. It felt like history happening in real time, a frontier market ready to explode. Edwin and his friends didn’t want to miss out, especially when companies were going public, and their share prices seemed destined to skyrocket.

One of those stocks was Tilray. At $143 a share, Edwin was convinced he was buying the future. He imagined stock splits, booming demand, and a cannabis empire rising from the ground floor. Instead, he watched that $143 tumble month after month, until he finally sold it for around 30 cents. The emotional rollercoaster of hope, disappointment, and finally acceptance was a journey Edwin will never forget.

A 99.3% loss.

He now calls it his worst investment—not just because of the financial hit, but because of how powerfully excitement and hype clouded his judgment.

• Every investor thinks their situation is unique. But in reality, the same patterns repeat again and again.
• Markets take time to mature.
• Regulation can shift overnight.
• Early doesn’t always mean right.
• Excitement is not a strategy.

• A portfolio isn’t just about diversification by industry or geography; it’s also about diversifying across stages of maturity.
• Stable, well-regulated companies like Coca-Cola or Pepsi behave very differently from early-stage, hype-driven industries, such as the cannabis sector.
• Even large companies, with teams of top analysts, often get it wrong.

If Edwin could offer one piece of advice to anyone starry-eyed over the next big thing, it would be this:

Do your due diligence. Seriously.

Before you invest in anything—especially something exciting, futuristic, or rapidly trending—slow down and ask:

• Has this been done before?
• What can I learn from past bubbles?
• What does...