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How Startups Win When Founders Ignore the Old Rules

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The conventional wisdom on how to start and run a business is evolving. Young, innovative leaders are disrupting well-entrenched industries by rethinking what has always been done and asking themselves, “Why can’t this be done differently?”

Douglas MacArthur once said, “You are remembered for the rules that you break.” Let’s take a look at three young founders who embody that spirit by building thriving companies that change the way things are done in the sports, logistics, and food industries. We’ll explore the lessons they learned, the unusual business models they used, and the rules they ignored or broke as they turned their vision into reality. 

First Broken Rule: Follow the market data (not your gut) 

If there is one true thing about the way business is done today, it’s that business is driven by data. Hardly a decision is made that involves committing capital without analyzing market data first. But Julianne Ponan, founder of Creative Nature, broke that rule by ignoring market research that said allergen-free foods were too niche to succeed. She chose to prioritize her own lived experience combined with anecdotal evidence from others over what the market was telling her to create. So, she created an allergen-free foods company that catered to an underserved market.

“I didn’t have decades of corporate conditioning telling me what not to do,” she says, “so I was fearless in challenging the status quo. That naïveté became an asset.” Her fearlessness resulted in a company whose food has a presence in major retailers and airlines.

Evan Floersch, founder of the Texas Ranchers professional pickleball franchise, also went against the data. While most metrics painted pickleball as a casual hobby, he saw a sport that had huge recreational adoption and imagined its future as a professional sport. He developed his team based purely on that vision. “We rebranded from a very fun, very light brand to one that was more serious. There was risk in doing that…but we anticipated the sport would be taken more seriously as it matured.”

These two approaches show that customer empathy and seeing potential where others don’t can reveal emerging demand before the data catches up to it.

Second Broken Rule: Chase capital first

As Shark Tank has taught us, capital is king. Fledgling businesses flock to that popular pitch show because they feel their business can go nowhere without a huge influx of cash. But Kevin Damoa, founder of Glīd, took a different approach. He’s developed “Glīders,” electrified vehicles that can move shipping containers straight from the road onto rail lines, cutting dozens of handoffs and days of waiting to make freight movement faster. To get there, Damoa formed solid partnerships first. He aligned with rail operators and other industry professionals who believed in his vision, and that brought the investors. Damoa remembers the fruits of that labor fondly. “When the time came to raise, we didn’t just pitch — we showed a coalition. That’s why our pre-seed was oversubscribed at $3.1M. Founders often chase capital like it’s oxygen. I chased trust.” 

Floersch broke from the capital-first playbook by structuring ownership around partners who could add cultural reach and credibility, not just funding. He saw teams owned by Tom Brady, LeBron James, and Mark Cuban and wondered, “How am I gonna compete against the influence and resources that these folks have? With my background in community building, I think the best way to do that is through partnerships."

He gave up some of his ownership to harness the power of a collective group. “We’ve got three kinds of buckets. We have athletes and celebrities who help us globalize the brand and reach new eyeballs like Li’l Wayne and Scottie Scheffler.” He continues, “The second one is individuals who are in sports or own sports teams. So we have the DeVos family, Dennis Wong who is part of the LA Clippers, and then kind of a third bucket which is industry leaders, industry heads. So these are sports marketers, PR folks, digital marketers who are definitely the best at what they do.”

Both of these approaches show that trust, alignment, and believers can create unstoppable momentum when combined the right way.

Three young professionals collaborating outdoors at a cafe, working together on a laptop.

Third Broken Rule: Winning is everything

In many arenas of business, winning is considered paramount. But these three entrepreneurs are redefining what it means to win—and what the usual business model is supposed to look like. Floersch prioritized the victory of a positive fan experience over his team’s performance on the field. “Rather than focus first on the competition…my team and I decided to focus on something different—our brand, the culture we wanted to create, and our community.”

Ponan proved that building inclusivity and brand boldness mattered more than chasing conventional mass appeal wins at launch. By making sure her foods were top-14 allergen-free, and putting bar codes on her products that provide ingredient information to the customer, she ensured product safety. She also chose bold product branding to set her products apart from others in the industry. “Our branding isn’t muted, clinical, or apologetic like many ‘free-from’ products. We’re bold, colourful, fun, and unashamedly inclusive.”

At Glīd, Damoa focused on designing smarter systems using AI orchestration rather than raw horsepower benchmarks that others saw as wins. He explains, “Yes: we chose intelligence over horsepower. The industry thought we’d be judged by torque, payload, and raw steel. Instead, we built EZRA-1SIX, our AI orchestration system. That decision transformed Glīders from vehicles into the nervous system of a universal logistics platform.”

Some rules are meant to be broken

If there is one common thread that unites these founders—and some of our other featured founders—, it’s fearlessness. Ponan reinforces this point when she says, “There were moments where I thought, ‘Who am I to do this? Am I smart enough? What if I do something wrong?’ But the flip side was that I had very little to lose.” 

This doesn’t mean the lesson is to always be chasing unicorns and rainbows. Rather than one huge win, their success is built of many small victories compounded over and over. As Floersch puts it, “The best advice I’ve received is to focus on hitting singles over and over again.” Rules are important, but knowing which ones can be broken can be even more valuable.

Rules are important, but knowing which ones can be broken can be even more valuable.

Key Takeaways


• Startups often succeed by challenging conventional business rules.
• Julianne Ponan built Creative Nature by ignoring data that said allergen-free foods were too niche.
• Customer empathy and lived experience can reveal markets before the data catches up.
• Evan Floersch bet on pickleball becoming a professional sport despite weak market signals.
• Kevin Damoa secured industry partnerships before seeking investors for Glīd.
• Trust and alignment can unlock capital more effectively than chasing money first.
• Strategic partnerships with celebrities and industry leaders gave Floersch’s team cultural reach.
• These founders redefined “winning” by prioritizing brand, inclusivity, and smarter systems over traditional metrics.
• Bold branding and inclusivity gave Creative Nature an edge in a conservative industry.
• Success is built through small, repeated wins rather than one big break.

John Boitnott
John Boitnott

John is a tech writer and journalist with  more than 20 years experience who contributes to several respected online publications, including BusinessInsider, Inc., and Entrepreneur. In addition to journalism, writing about social good companies and in-depth research, he is also active in his community and enjoys metaphysical book-reading groups, as well as hiking on the amazing trails of the San Francisco Bay Area.

John graduated with a degree in Communications at UC Santa Barbara and soon afterward began his journalism career. He worked in TV news from 1994 to 2009, and served as web editor and writer at KNTV, San Francisco’s NBC affiliate. He also wrote for KGO, KRON and KPIX in San Francisco, and worked as a radio anchor, assignment desk manager, reporter, editor and producer at KEYT in Santa Barbara for ten years. After stints with agencies and startups, John has returned to working with various newsrooms across the country.

John currently writes pieces on productivity, career advice, tech trends, AI, marketing, social media, as well as companies that help underserved communities around the world. Several Fortune 500 companies utilize his writing skills for their blogs and other online content.

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