On The Delo EP171 – Entrepreneurship, Startups, and Serving Main Street: Building a Brand That Cares Entrepreneurship, Startups, and Serving Main Street: Building a Brand That Cares

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ON THE DELO: Arizona Restaurant & Hospitality Stories

David "The DELO" DeLorenzo

186 episodes

5 days ago

Step inside ON THE DELO Podcast: Arizona Restaurant & Hospitality Stories. Hosted by David “DeLo” DeLorenzo—entrepreneur, insurance expert, and connector of people—this show dives deep into conversations with chefs, restaurateurs, brewers, and creators shaping the industry. Beyond business, DeLo explores health, mindset and community, exploring what it really takes to thrive in hospitality and in life. This podcast is here to help you get connected, stay protected, and keep growing. Subscribe now and join a community where hospitality, health, and hustle come together.

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On The Delo EP171 – Entrepreneurship, Startups, and Serving Main Street: Building a Brand That Cares Entrepreneurship, Startups, and Serving Main Street: Building a Brand That Cares

ON THE DELO: Arizona Restaurant & Hospitality Stories

33 minutes 22 seconds

3 months ago

On The Delo EP171 – Entrepreneurship, Startups, and Serving Main Street: Building a Brand That Cares Entrepreneurship, Startups, and Serving Main Street: Building a Brand That Cares

Step into Episode 171 of ‘On the Delo’ as David DeLorenzo welcomes Bobby, CEO and co-founder of Rainbow Insurance, for a refreshingly honest exploration of what it takes to reinvent an industry from the inside out. Bobby shares his journey from launching startups in Boston to building niche-driven, tech-enabled insurance solutions in San Francisco, with candid insights about entrepreneurship, leadership, and why people are always the real differentiator.

Get the inside story on how Rainbow found its name, why Main Street businesses matter, and what “admitted” vs “non-admitted” products really mean for hospitality owners. From memorable startup moments to practical risk management tips, this conversation is packed with real stories and hard-won lessons. If you’re a business owner, agency leader, or hospitality operator who wants to thrive in unpredictable times, you’ll find actionable takeaways and a reminder that insurance is always about people first.

Chapter Guide (Timestamps):

(0:00 – 1:00) Family Beginnings & Episode WelcomeBobby and Delo swap stories about kids and business, introducing Episode 171 and today’s guest, Bobby, Rainbow Insurance CEO.

(1:01 – 2:30) Founding Rainbow: From Naming to Why It StuckDiscover how a spur-of-the-moment idea became a vibrant brand—and why a memorable, positive name can open unexpected doors.

(2:31 – 4:30) Entrepreneurial Roots and the Accidental Startup PathBobby shares his first exposure to entrepreneurship, the twists and turns of early ventures, and how he “fell into” building companies after the 2008 financial crisis.

(4:31 – 7:00) Moving to Insurance: Calling, Community, and Industry LessonsWhy insurance, why hospitality, and why niche? Learn how Bobby found his calling in insurance by valuing people and community over hype and scale.

(7:01 – 9:59) Main Street & Hospitality: The Power of Focused ImpactHear why hospitality was chosen over trendier sectors and how food, family, and local economies inspired a program built for restaurants and community resilience.

(10:00 – 12:56) Building the MGA: Team, Technology, and Invested GrowthGo behind the scenes on starting a tech-forward MGA, assembling the right team, and raising the bar for underwriting and customer service excellence.

(12:57 – 16:27) Insurance 101: Admitted, Non-Admitted, and Market DynamicsExpert explanations and market realities—what every operator and agent should know about product types, risk zones, rates, and regulatory nuance.

(16:28 – 19:30) Claims, Catastrophes, and Real-World RiskTrue stories from the front lines: what’s driving most claims for restaurants, why weather matters more than ever, and how responsiveness changes everything in recovery.

(19:31 – 24:23) Lessons for Owners: Risk Prevention and Hiring for ExcellenceBobby’s biggest advice for hospitality owners: be present, hire quality people, and run a great business—because leadership affects everything, including your bottom line.

(24:24 – 29:47) Beauty, Wellness, and the New Insurance NicheExplore Rainbow’s expansion into health and wellness insurance, and how Bobby manages high energy and personal wellness while growing a company and raising two kids.

(29:48 – 30:56) Daily Choices, Healthy Habits, and Airport TemptationsPractical tips for staying on track with wellness—whether at the office, on the road, or navigating the temptation of airport fast food.

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