Operators

“We know how to run ads. This is a playbook.” 
How should you market a new DTC brand in its first six weeks? 
Matt Bertulli (Founder, Pela Case & Lomi), Cody Plofker (Advisor & fmr. CEO, Jones Road Beauty), and Curtis Christopherson (Chief Growth Officer, Ammortal) hold the Winks marketing plan up against the results since launch. 
They built the brand for moms, yet men keep showing up to buy. Meta CPMs hit $800 until a free account fix and a smaller budget turned them around. Now creators and credible doctors have to bring CAC down to $100 before they scale. 
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“It’s about closing the imagination gap, not what it can do.” 
Jessica Schinazi (CEO, Away) joins Matt Bertulli (Founder, Pela Case & Lomi) and Curtis Matsko (CEO, Portland Leather Goods) to break down how she took the reins of a decade-old DTC pioneer and opened it to new channels in 18 months. 
Away builds luggage to last 7 to 10 years, which Jessica calls a horrible business model. She chases new buyers: Up to 9% of her Amazon category and a $400 suitcase sold out on TikTok Shop. Now she has to bring each customer home before a day-one startup steals them. 
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“You can have anything you want, but you can’t have it all at once.” 
Should you raise money when your only problem is working capital? 
Help an Operator Out (HAOO) is a series where real business owners join the podcast with live questions. In this episode, TJ Bongiorno (Founder, The Outgoing Co) brings two questions: when to raise capital and how to price the round. As a solo founder, he 4X’d the business to nearly $4M in a year. 
Nearly 90% of TJ’s revenue comes from powder, yet his cans perform 100X better on TikTok Shop. The hosts push him to choose which product leads his pitch. Matt makes the case for a price where investors win easily. Caught between seed funds and VCs, TJ needs a deal the right investors will take. 
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“They’re the most capable ever, but not trained on your business.”
What pillars should every AI-first brand build, and which one comes first? 
Matt Bertulli (Founder, Pela Case & Lomi) and Cody Plofker (Advisor & fmr. CEO, Jones Road Beauty) open up the playbook behind Winks, a brand where AI does the grunt work and humans make the calls. Piece by piece, they break down the four components that make that split work. 
1. Company brain: Context, memory, skills 
2. Operating system (OS): Human interface 
3. Software and tools: Existing tech, SaaS 
4. Agents: Researcher, writer, analyst, etc. 
The era of “prompt engineering” is over. Company context lets agents upload ads and match landing pages without being told twice. Yet AI tools still misread research, which leaves one question: How much can you trust them? 
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“You’re never gonna make a big impact on Black Friday.”
Should you worry if frequent promotions will hurt your brand equity?
Sean Frank (CEO, Ridge), Matt Bertulli (CEO, Pela Case and Lomi), and Mike Beckham (CEO, Simple Modern) break down how Ridge manufactures demand instead of waiting for it. A slow summer becomes an 8-figure-plus sales season, anchored by a Lamborghini sweepstakes with Tony Hawk. 
Sean walks through how the campaign evolved from a $100K MVP into a five year, celebrity backed giveaway with a grand prize built in. He explains why a 45-day window beats trying to own a single day like Black Friday. The hosts continue to cover why a wider product catalog creates more natural sales peaks throughout the year. 
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