Operators

“A great offer makes the customer feel stupid for saying no.” 
How do you know your offer is wrong before the market tells you? 
Jordan Menard (Co-Founder, Instant Hydration) and Lina Fahizul (Chief Ovary Officer, Freelance) join this episode to put Winks’ pricing, promotion, and pitch on trial. The payoff is a 10-element offer playbook any DTC brand can steal. 
1. Not just price or discounts 
2. Fits how the product is used 
3. One customer + one problem 
4. Adds value before discounts 
5. Tackles your top objections 
6. Gives a reason to buy “now” 
7. Priced right for your market 
8. Your most-valuable customer 
9. Built for orders 2, 3, 4, etc. 
10. Profitable unit economonics 
It starts from a simple claim: Your discount gives away margin once. Jordan catches the founders without an answer for the CAC they can afford. Lina shows why making moms feel bad wins the click and loses the customer. Today's “winning” offer could lose money for months. 
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“Better is probably the worst word you could use in marketing.” 
How can a DTC brand stand out in a category full of identical promises? 
Matt Orlić (Co-Founder, Qure Skincare) joins Mike Beckham (CEO, Simple Modern) and Matt Bertulli (Founder, Pela Case & Lomi) to break down why brand positioning beats a better product. Each story shows how a brand can win a crowded category without inventing anything new. 
Qure’s water filters beat Jolie’s on technology and patents, yet Orlić can’t out-position them. Mike explains how Yeti took Thermos’s 1800s vacuum insulation and sold it for cold drinks. Once a position works, competitors move in, and the founders debate how to hold it. 
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“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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