Podcast Summary: Restaurant Unstoppable with Eric Cacciatore

Episode 1243 — Elizabeth Tilton, Founder & CEO of Oyster Sunday and OS BENEFiTS

Date: January 8, 2026

Overview:

This episode dives into the entrepreneurial journey of Elizabeth Tilton, founder and CEO of Oyster Sunday and OS Benefits, as she shares essential strategies and lessons for independent restaurateurs. Elizabeth discusses her unique trajectory from aspiring doctor to hospitality innovator, the importance of adaptability, the evolution of strategic outsourcing and fractional executives in the restaurant industry, and her groundbreaking work making health insurance accessible for hospitality workers. The conversation offers actionable insights on leadership, technology, business models, and the power of community.

Key Discussion Points & Insights

1. Personal Mantras, Career Origins, and Overcoming Fear

• Opening Mantras:

  • "Seek, Trust, Deserve It" — A guiding principle of partnership and integrity (Elizabeth, 04:30).
  • "What would you do if you knew you could not fail?" — The power of removing fear from the equation and embracing self-awareness (Elizabeth, 04:54).

• Fear of Failure:

  • “Fear is the number one thing that holds us back.” (Eric, 05:11)

• Switch from Medicine to Hospitality:

  • Early love for cooking; dinner parties in high school, pre-med in college, but dyslexia and a catering side business inspired a leap into food.
  • “Do I really want this?” — The courage required to deviate from expectations (Elizabeth, 10:08).
  • “I do think [dyslexia] has become a superpower over the long run.” (Elizabeth, 12:36)

2. Career Evolution & Building Oyster Sunday

• Quick Career Timeline (13:45–15:04):

  • Head chocolatier → pastry cook → PR/branding at Momofuku → brand lead at WMP (industrial design) → advisory boards → launching Oyster Sunday and OS Benefits.
  • Willingness to jump into the unknown, learn on the job:
    "I didn't know what I was doing. I was learning... but that doesn't scare me." (Elizabeth, 15:56)

• Momofuku Influence:

  • Oversaw multiple units, learned large-scale operations and the need for interdisciplinary support systems (Elizabeth, 18:20).

• Oyster Sunday’s Mission (18:26):

  • "A strategic partner—your corporate office for independent restaurants," covering finance, marketing, branding, operations, HR, plus data & technology (Elizabeth, 18:38).
  • Fractional executive services: filling organizational gaps, scaling support, and bridging strategic knowledge to independents.

3. Modern Restaurant Operations & The Power of Fractional Executives

• The Emerging Model:

  • Outsource what can be handled better by specialists—fractional CFOs, CMOs, etc.
    “I believe fractional executives are what keeps independents competitive.” (Eric, 19:51)

• Oyster Sunday’s Services:

  • Retainer and project-based across key departments ("from wine labels to NOMA projects"), specifically NOT in food production or bookkeeping (Elizabeth, 20:25).

• Building the Team:

  • Started as a solopreneur, scaled by leveraging networks and independent contractors, hiring for strengths, and remaining remote and cloud-based (Elizabeth, 34:26–36:13).

4. Finance & Raising Capital: Modern Best Practices

• Financial Advisory:

  • Deep focus on forecasting, financial review, efficiency, and strategic planning—helping operators ask for enough capital and plan tech investments (Elizabeth, 39:34).
  • "Success is relative. What does it mean to you?" — Align growth planning with the operator’s lifestyle and vision (Elizabeth, 46:45).

• Partner/Ownership Models:

  • Profit sharing, rev sharing, bonus structures, and equity models praised for creating generational wealth and retention.
  • “The best business models are going to be those with lots of partners.” (Eric, 49:58)

5. Technology, Data, and the Future of Operations

• Choosing Your Tech Stack:

  • Build tech in phases—don’t over-invest too soon; keep data organized for eventual upgrades.
  • Recommendations:
    • POS: Toast (industry standard), but SpotOn and up-and-comers like Ponzo are emerging (Elizabeth, 59:51).
    • Inventory/Analytics: Restaurant365, MarginEdge, Ingestion, Opus for training.
    • Marketing/Loyalty: Blackbird, Loyalist, Biki for customer segmentation.
  • Data cleanliness is vital—tech is only as good as the data you feed it (Elizabeth, 58:05).

• Cautions on Tech Consolidation:

  • “How do we get to the point where two companies control all reservations?” (Eric, 78:32)

6. Human Resources: Compliance, Culture, and Recruiting Talent

• HR Platforms:
  • Gusto, Paylocity, Paycom, ADP, and integrated POS payroll like Toast Payroll (Elizabeth, 70:46–71:25).
  • Emphasis on cultural, not just legal, employee handbooks—“What does it mean to be us?” (Elizabeth, 72:15).

7. OS Benefits: Revolutionizing Health Insurance for Hospitality

• Genesis & Motivation:

  • “If we can’t offer health insurance, how do we expect to compete for talent?” (Eric, 94:29)
  • Elizabeth’s struggle to find affordable, accessible health insurance for hospitality workers led her to spend years building OS Benefits.

• How It Works:

  • OS Benefits is a health-tech association plan — combining broker, benefits administration, and payment processing.
  • Any business (as few as two employees) participates, leveraging group buying power to reduce cost and improve access (Elizabeth, 87:53).
  • Fully digital, six-step onboarding, instant access to provider networks and plan details.
  • Includes 30+ wellness benefits (childcare, women’s health, continuing ed, etc.).

• Impact Stories:

  • “If I didn’t have this, what would have happened? … It would have put me in medical debt.” (Elizabeth sharing a client story, 88:27).

• Long-Term Vision:

  • Commitment to serving small business, not chasing scale for its own sake:
    "Innovation happens in small and independent business." (Elizabeth, 95:57)

Notable Quotes & Memorable Moments

• "I always lead with a sense of optimism ... assuming the best intention for our relationship." — Elizabeth (06:53)
• "Every single independent business in hospitality has an exceptional team. There could be gaps. We support your weaknesses." — Elizabeth (19:01)
• "People will value why over what. Particularly as Gen Z comes up—empathy is everything." — Elizabeth (29:27)
• "Fractional executives combined with rapidly evolving technology... that's the secret sauce." — Eric (41:46)
• "If you're going to give up $20,000, you're going to take it seriously." — Eric (53:24, on Uptown Hospitality’s path-to-ownership model)
• "Care is an issue of access, but also of recruitment and retention." — Elizabeth (94:27)
• "Because I think innovation happens in small and independent business." — Elizabeth (95:57, on her commitment to independents)
• "Hospitality is literally who we are as a species." — Eric (30:16)

Timestamps for Key Segments

• Opening & Mantras: 03:43–06:53
• Career Journey & Dyslexia: 07:08–13:00
• Momofuku/Brand-Building Lessons: 13:45–19:51
• Launching Oyster Sunday: 18:26–19:51
• Finance & Raising Capital: 39:34–47:11
• Ownership/Partnership Models: 49:36–54:40
• Tech & Operations Stack: 56:05–66:19
• HR, Culture, and Talent: 70:46–72:35
• Reservations & Marketing Tech: 77:49–81:18
• OS Benefits Deep Dive: 83:40–95:19

Resources, Books & Companies Mentioned

• Books:

  • Unreasonable Hospitality by Will Guidara
  • The Speed of Trust by Stephen M.R. Covey
  • Power and Progress by Daron Acemoglu & Simon Johnson
  • Why Nations Fail by Daron Acemoglu & James A. Robinson

• Tech & Service Companies:
  Toast, SpotOn, Ponzo, Ingestion, Restaurant365, Opus, Blackbird, Loyalist, Biki, Gusto, ADP, MarginEdge

• People & Organizations:
  Uptown Hospitality, Max Goldberg (Nashville), Southern Smoke Foundation (Chris Shepherd), May May (Irene Lee), WMP (Josh Williams, Eric Prom), Empath (Elizabeth Meltz), Slang AI (Alex), OpenTable, Resy

Final Thoughts & Contact Info

• Elizabeth’s Commitment:
  Refuses to pivot focus to large chains—her mission is supporting small business and empowering hospitality professionals through community, scalable support, and better health coverage.

• Contact:

  • Websites: oystersunday.com, osbenefits.co
  • Email: elizabeth@oystersunday.com

• Community Q&A:
  Elizabeth will join the Restaurant Unstoppable Network on Feb 25, 2026, for an open discussion about reimagining healthcare.

“We are dealers of food. Food is life. We have a lot of influence — we can go further together.”
— Eric, 98:54

For additional show notes and action resources, visit RestaurantUnstoppable.com.