319 - Dan Perry & Michael Serapiglia – "If You Get Lost, Enjoy the View Around You"

Some stories begin with a business plan. Others begin with a feeling — a deep, lived truth that travel isn't just about going somewhere, but about finally being somewhere without fear.  That's the story behind Toto Tours.  When founder Dan Ware launched the company in 1990, LGBTQ+ travelers faced a world far less welcoming than it is today. Travel was often an act of courage. Safety wasn't guaranteed. Connection wasn't a given. And yet Dan believed something radical: that the world belonged to everyone, and that queer people deserved to explore it without shrinking, hiding, or apologizing.  That early mission — to create safe, joyful, life-changing journeys — set the foundation for one of the longest-running LGBTQ+ tour companies in the world. Today, that legacy is being carried forward by Dan Perry and Michael Serapiglia, two leaders who bring heart, artistry, and intentional strategy to the next era of Toto Tours.  Michael's background alone is a reminder that great careers rarely follow straight lines. A Broadway dancer in productions like Annie Get Your Gun and Aida, an Emmy®-nominated makeup artist, and a lifelong student of people and culture, Michael brings a performer's attention to detail and a creative's sense of wonder to everything he touches. That energy is written all over Toto's new vision — a company designed not just to take people places, but to orchestrate experiences.  Dan, meanwhile, is rooted, thoughtful, and anchored in the operational heartbeat of the business. As co-owner and steward of the brand's legacy, his leadership ensures that the company's emotional mission is matched with real-world execution: logistics handled with precision, safety prioritized above all else, and every traveler supported as a deeply valued guest.  Together, they are scaling Toto Tours for the next generation — bringing structure to creativity, growth to mission, and clarity to chaos. That blend shows up beautifully in their napkin:  "Remember… if you get lost, enjoy the view around you."  It's playful. Light. But also quietly profound.  Because travel does involve getting lost. Entrepreneurship definitely involves getting lost. And navigating identity, belonging, and community? That's a lifelong journey with no perfect map.  What makes Toto Tours powerful — and what makes Dan and Michael's leadership so compelling — is how they embrace that "lostness" with intention. They've built a business around creating psychological safety in unfamiliar places. They design tours where vulnerability isn't a risk, but a pathway to connection. And they do it in a way that proves something important:  When your business is built on empathy and authenticity, growth becomes a natural outcome — not the goal.  In our conversation, they talked about inheriting a business that has meant something real to thousands of travelers. They shared the challenges of honoring a 35-year legacy while modernizing every aspect of the customer experience. They spoke openly about the responsibility that comes with being stewards of a community, not just operators of a company.  And what stood out most was this: Their success is rooted in the courage to stay human in an industry that often forgets to be.  Their stories ranged from navigating international travel logistics to deeply personal moments on tour — when someone feels seen for the first time, or finally gets to show up as their full self after years of holding back.  This is not a commodity business. This is not "selling vacations." This is transformational work disguised as travel.  And Dan and Michael are the right leaders at the right moment — blending heart, craft, psychological safety, and strategic growth in a way that honors the past while confidently shaping the future.    5 Key Takeaways (with Take Action steps)  1. Empathy is a business strategy, not a soft skill.  Toto Tours was built on understanding the emotional experience of the traveler. That core value is still their competitive advantage. Take Action: Identify one customer anxiety or emotional need you haven't been addressing — and build a process or moment that solves it.    2. Legacy is something you steward, not something you own.  Dan and Michael inherited a 35-year mission. Their role is not to change the soul of the company, but to carry it forward. Take Action: If you lead a team or a business, ask: What part of our legacy must remain untouched? What part needs to evolve right now?    3. Safety creates the conditions for joy.  Their tours work because people feel safe — emotionally, physically, and socially. Safety unlocks curiosity and connection. Take Action: Audit how your team experiences psychological safety. Identify one area where people still "armor up."    4. Creativity and structure don't compete — they complete each other.  Michael brings artistry. Dan brings operational consistency. Together, they create magic. Take Action: Look at your own leadership style. What's your opposite energy — and who could you partner with to balance your approach?    5. Getting lost is part of the journey — but meaning comes from how you respond.  Their napkin says it best: if you're lost, enjoy the view. Trust the moment you're in. Take Action: Ask yourself: Where do I feel lost right now? Instead of fixing it, what can I appreciate about this moment?    About the Guests  Dan Perry & Michael Serapiglia – Co-Owners, Toto Tours  Toto Tours began in 1990 when founder Dan Ware envisioned safe, joyful global travel for LGBTQ+ explorers.  The company has grown into a trusted international leader rooted in community, inclusion, and curiosity.  Today, Dan Perry and Broadway-performer-turned-Emmy-nominated-makeup-artist Michael Serapiglia carry the torch, expanding Toto's impact while honoring its spirit.  Their work blends purpose, creativity, and operational excellence — proving that meaningful business growth begins with humanity.    Links   website: www.tototours.com     CHAPTERS 00:00 Welcome + the meaning behind today's napkin 01:42 How Toto Tours began as a radical act of safety 05:20 Dan & Michael: leadership through empathy 11:10 Growing a legacy brand without losing its heart 17:45 Psychological safety as a business strategy 22:30 Michael's artistic lens: creativity in operations 28:05 Getting lost and loving the view: the napkin lesson 33:50 Advice for entrepreneurs leading through uncertainty 35:10 Final reflections + Paper Napkin Wisdom takeaway