From $15 Online Community to a Sold-Out Retreat and 80-Person Summit in One Quarter

When Ashley and I started working together, she wanted to rebrand her online community. What happened next surprised both of us. In one quarter, she sold out a business retreat, relaunched her mastermind, signed two 1:1 coaching clients in 48 hours, and hosted a free summit with 80+ people where attendees were offering to sponsor her next event — live, in the Zoom chat. In this interview, we walk through exactly how she did it: the bold asks, the pricing shifts, the content strategy, and the moment she realized she’d been a sales expert all along without knowing it. If you’ve been undercharging, underselling, and wondering why it’s not clicking — this one is for you. Follow Ashley on Instagram:   / yourworkwifeashley   Sell Like You Story Template: https://theworkinggalco.myflodesk.com... Bold AF Summit: https://www.yourworkwifeashley.com/bo... Learn more about The Sell Well Services: https://thesellwell.com/ Calculate How Much Money Your Instagram Can Bring You: https://thesellwell.com/calculator 0:00 The Art of Building Multiple Businesses 5:29 Relaunching the Work Life Mastermind 7:23 The Pricing Strategy That Changed Everything 10:14 Finding Your Mirror in Business 14:14 The Catalyst for Boldness 15:50 Grieving the Previous Version of Your Business 33:03 Selling Out a Retreat in Ten Days 44:35 Advice for Aspiring Bold Founders