How To Sell to 9 Figure Brands

Try Attentive: https://www.attentive.com/ Try Fuego: https://fuego.io/ Download Your Free Post Purchase Checklist: https://www.thedivenewsletter.com/post-purchase-checklist If you’ve ever wondered how to sell to rich people, enterprise accounts, or fast-growing 8 and 9-figure brands, this episode is the most tactical deep dive you’ll find anywhere. Today, the guys break down — in brutal honesty — exactly how successful founders and marketing leaders WANT to be sold to… and how most people get it embarrassingly wrong. Featuring: • Nick Shackelford — Partner at BREZ, operator behind multiple brands sprinting toward 9 figures • Bart S — Founder of Dad Gang, leading an 8-figure brand growing fast • John J Coyle — VP of Marketing at Royo Bread Co, another brand approaching 9 figures Between them, these operators have worked with dozens of top-tier brands, negotiated with SaaS companies, hired agencies, and reviewed thousands of cold pitches. This episode reveals the real buying psychology behind the curtain. --- What You’ll Learn in This Episode 1. How to Sell to 8–9 Figure Brands (Without Cringe Tactics) 2. Why Founders Buy: Maximizing vs. Optimizing Cycles 3. Cold Emails That Actually Work 4. The ONE Way Every 9-Figure Buyer Starts Their Search 5. How to Run Demos That Actually Close 6. Creative Ways SaaS Companies Close Big Accounts 7. Why Building a Personal Brand Lowers Your SaaS Bill 8. BONUS: How to Scale a $1,000/Month Mobile Pet Grooming Service  ⸻ This Episode Is For You If… • You’re an agency, SaaS founder, service provider, or consultant • You’re trying to sell bigger clients without sounding desperate • You want to understand how fast-growing brands actually think • You want to master cold outreach that doesn’t get instantly deleted • You want to create offers 8- and 9-figure operators actually buy ⸻ Timestamps 00:00 – Selling to rich people & 9-figure companies 01:30 – Maximizing vs. optimizing (and how to tell the difference) 03:20 – What commoditized offers must do differently 05:40 – How large teams think about time, workload, and demos 07:00 – Bart’s rule: “I only buy what my friends recommend” 10:00 – Cold email teardown: good vs. terrible examples 12:50 – Why founders hate vague SaaS positioning 14:50 – The dating analogy: why trust beats all outreach 17:30 – How to network with high-level operators 19:00 – Why personal brands give operational leverage 22:00 – Going upmarket: the REAL path (not what gurus tell you) 23:30 – What happens on demos that lose deals 25:40 – How founders think about switching costs 28:00 – Creative SaaS deal structures you’ve never seen 30:00 – The ONE thing bigger than any SaaS discount 32:00 – Why some brands choose one platform for everything 35:00 – Listener question: scaling a luxury pet grooming business 40:00 – Packaging convenience, service, and premium positioning 41:45 – Referral loops, add-ons, and retention mechanics