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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.

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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


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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

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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