In this episode, the guys break down the real strategy behind landing recurring and annual contracts, the type of deals that can add hundreds of thousands of dollars in predictable revenue to a mobile catering business.

Justin walks through the story of Goodhart Coffee’s first recurring contract, how informal repeat bookings turn into long-term deals, and the surprising truth about why some companies hire carts weekly for years. They also cover how to price these contracts, how to handle messy payment terms, and why pre-event communication workflows are the secret weapon for keeping clients coming back.

If you’ve ever wondered how to go from one-off gigs to steady, reliable contracts that pay year-round, this is the playbook.

➡️ Join our Mobile Catering Accelerator (free): https://www.skool.com/mobile-catering-accelerator/about
➡️ Claim our guide to the software stack you need as a mobile caterer: https://www.flashquotes.com

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⏱️ Timestamps

00:00 Welcome back + FlashQuotes community updates
00:30 Why recurring contracts matter for mobile caterers
01:45 How Justin landed his first long-term contract in 2020
02:40 The $400K contract Goodhart lost — and what it teaches about risk
04:07 How repeat, informal bookings turn into annual contracts
04:23 Pricing, payment terms, and surviving net-60 corporate cycles
06:05 When to suggest a contract vs. when clients bring it up
07:00 Which companies are most likely to offer annual deals (tech, national brands, corporate offices)
07:49 How to identify your best recurring contract opportunities in your CRM
08:20 Why tastings matter — and when to comp them for big deals
09:38 What percentage of Goodhart’s revenue comes from repeat clients (and how to estimate yours)
11:46 Using client data to drive rebookings and retention
12:24 Email blasts, slow-season strategy, and rebooking campaigns
13:32 How to track your top clients and repeat patterns in FlashQuotes reports
14:45 Building predictable follow-up workflows (3-, 6-, and 12-month pings)
16:05 New FlashQuotes automated pre-event and post-event workflows (and why they reduce client anxiety)
17:00 Why client reassurance is a retention superpower (7-day and 24-hour confirmations)
19:23 Pre-built workflows coming soon — and why they’ll be a game changer
20:05 When (and when not) to offer tastings for weddings and corporate deals
22:57 Booking comped services for high-value corporate prospects
23:32 Handling eight-hour events and long shifts with a single barista
— refills, breaks, and managing fatigue the smart way
24:00 Final takeaways on recurring revenue and long-term client relationships

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🔑 Key Points

• Recurring contracts usually start as informal repeat bookings
• Big companies will pay a premium for consistency, reliability, and professionalism
• Payment terms get worse as contracts get bigger — plan accordingly
• Tastings are worth it when lifetime value is high
• Email blasts + smart follow-up = predictable rebooking
• FlashQuotes workflows are becoming the retention “cheat code” for mobile caterers
• The easiest recurring revenue starts with the clients you already served