In one of the most inspiring and down-to-earth episodes of The Prospecting Show, Dr. Connor Robertson sits down with Jeff Fenster, the founder of Everbowl and serial entrepreneur known for his people-first philosophy. Together, they explore one of the most overlooked assets in business: trust.
Dr. Robertson opens with a simple truth — “You can’t fake trust. It’s built one conversation at a time.” Jeff nods, adding that in business, trust compounds faster than capital. “You can raise money, buy ads, and hire teams,” he says, “but without trust, you’ll always have to push instead of pull.”
Their discussion goes deep into what it really means to build authentic relationships, maintain integrity under pressure, and create lasting business success rooted in character, not gimmicks.
The Foundation: Why Trust Outlasts Everything
Jeff shares that his entire career has been built on relationships, not transactions. “People do business with people they like and believe in,” he says. “If you can consistently show up with integrity, you’ll never run out of opportunities.”
Dr. Robertson agrees, explaining that while most founders obsess over tactics, the best ones focus on character. “Trust isn’t built in boardrooms — it’s built in moments when no one’s watching,” he says.
They both emphasize that trust is not a marketing campaign. It’s a behavior pattern. “If your brand says one thing but your actions say another, people will feel it instantly,” Jeff adds.
Dr. Robertson connects this to leadership and culture. “Your team mirrors your example,” he says. “If they see consistency in how you lead, they’ll replicate it in how they serve customers.”
Jeff notes that trust isn’t something you demand — it’s something you earn. “Every interaction is a deposit or withdrawal in your trust account,” he says. “Leaders who understand that rarely go bankrupt.”
The Power of Authenticity
Jeff explains that authenticity has become the new competitive advantage in an era of hyper-connectivity. “People have radar for fake,” he says. “They don’t want perfect — they want real.”
Dr. Robertson agrees and reflects that authenticity also creates resilience. “When your public image matches your private reality, you have nothing to hide,” he says. “That’s freedom.”
Jeff shares that he’s built his brand by being unapologetically himself — approachable, honest, and human. “If you’re not authentic, you’ll attract the wrong customers and repel the right ones,” he says.
Dr. Robertson points out that social media has blurred the line between personal and professional presence. “It’s not about building a persona,” he says. “It’s about being consistent across platforms, conversations, and actions.”
They both agree that authenticity requires vulnerability. “When you share failures as openly as successes,” Jeff says, “you build connection. People don’t relate to perfection; they relate to progress.”
Building Teams That Trust Each Other
Dr. Robertson transitions the discussion to leadership, asking Jeff how trust translates within organizations. “Trust is oxygen,” Jeff says. “Without it, teams suffocate.”
He explains that trust starts with clarity. “If your team doesn’t know your expectations or purpose, they’ll fill the gap with fear,” he says. “Transparency beats talent every time.”
Dr. Robertson agrees that alignment is the foundation of culture. “When everyone understands the why, they’ll figure out the how,” he says.
Jeff adds that leaders must be consistent. “The moment you break your word, you break momentum,” he says. “Your team will forgive mistakes, but they won’t forgive dishonesty.”
Dr. Robertson connects this to accountability. “Trust doesn’t mean avoiding hard conversations,” he says. “It means delivering truth with respect.”
They both share examples of businesses that scaled because of strong internal trust — teams that communicated clearly, made quick decisions, and supported each other through uncertainty.
Jeff sums it up perfectly: “You don’t build culture in the good times. You build it in how you respond to the bad ones.”
The Customer Perspective
Trust extends far beyond teams — it defines how customers experience your brand. Jeff explains that every touchpoint is an opportunity to either earn or erode trust. “If you say you care, prove it with action,” he says. “Trust is built by consistency, not slogans.”
Dr. Robertson agrees, noting that in a crowded marketplace, reputation is the only true moat. “Price and product can be copied,” he says. “Trust cannot.”
Jeff shares that at Everbowl, customer feedback isn’t treated as criticism but as collaboration. “We tell our customers, ‘You’re part of our growth,’” he says. “That transparency builds loyalty.”
Dr. Robertson relates this to small businesses and startups. “Even with limited resources, you can build infinite goodwill,” he says. “Trust costs nothing but pays everything.”
They both emphasize that trust-driven companies don’t have to compete on marketing volume. “When people trust you,” Jeff says, “they become your marketers.”
Scaling Trust in a Digital World
Dr. Robertson asks how entrepreneurs can maintain trust at scale, especially when they grow beyond personal relationships. Jeff responds, “You scale trust by scaling systems that mirror your values.”
He explains that this means documenting culture, hiring by character, and creating feedback loops. “Values aren’t posters on the wall,” he says. “They’re policies in motion.”
Dr. Robertson notes that automation and technology often create distance. “But they don’t have to,” he says. “When used right, they amplify humanity — they help you show up faster, clearer, and more consistently.”
Jeff agrees, sharing how he uses automation to deliver better customer experiences without losing authenticity. “If tech helps you keep promises, it builds trust,” he says. “If it replaces empathy, it destroys it.”
Dr. Robertson adds that the future of business will belong to founders who merge efficiency with empathy. “Trust and technology aren’t opposites,” he says. “They’re the next evolution of leadership.”
Reputation as a Business Asset
Both Dr. Robertson and Jeff agree that trust isn’t intangible — it’s a measurable asset. “Your reputation is a form of equity,” Jeff says. “It compounds over time and protects you when things go wrong.”
Dr. Robertson points out that a strong reputation creates optionality. “When people trust you, doors open,” he says. “You’ll never have to chase opportunity again.”
They discuss how every entrepreneur should treat their reputation like their balance sheet — something to invest in and protect. “You can’t pivot your way out of dishonesty,” Jeff says. “Integrity is non-negotiable.”
Dr. Robertson connects this to his broader philosophy: “In the long run, trust is the ultimate ROI. You might make quick money through hype, but you build real wealth through credibility.”
The Trust Flywheel
Jeff introduces what he calls the “Trust Flywheel” — a cycle of transparency, delivery, and consistency. “When you communicate honestly, deliver what you promise, and repeat that over time, trust compounds exponentially,” he says.
Dr. Robertson notes that this compounding effect mirrors business growth itself. “It’s the same principle as compound interest,” he says. “The earlier and more consistently you invest in trust, the bigger your long-term return.”
They both agree that while marketing gets you attention, trust gets you longevity. “Anyone can sell once,” Jeff says. “Trust lets you sell forever.”
Dr. Robertson sums it up powerfully: “Trust turns customers into advocates, employees into ambassadors, and leaders into legends.”
Lessons for Entrepreneurs
As they wrap up, Dr. Robertson and Jeff share actionable lessons for founders and leaders:
• Lead with honesty, even when it costs you short-term gain.
• Make promises you can keep — and keep every promise you make.
• Hire for integrity over skill; skills can be taught, character cannot.
• Build systems that reflect your values, not just your goals.
• Protect your reputation like an asset — it’s your most valuable currency.
Dr. Robertson reflects that trust, not tactics, is what defines sustainable success. “You can always rebuild systems,” he says. “But once you lose trust, the foundation cracks.”
Jeff concludes with a challenge: “Don’t chase success. Build trust so strong that success has no choice but to find you.”
Their conversation leaves listeners with a timeless reminder — in business and in life, the highest form of strategy is sincerity.
Listen and Learn More
Listen to the full episode here: Building Trust in Business with Jeff Fenster