From Corporate Burnout to 8 Figures: The Story Behind Little Trouble episode artwork

EPISODE · Aug 22, 2025 · 48 MIN

From Corporate Burnout to 8 Figures: The Story Behind Little Trouble

from The DTC Insider · host Brian Roisentul

In this episode of The DTC Insider podcast, Brian Roisentul chats with Dinah Chapman, founder of Little Trouble, a fast-growing kidswear brand that’s on track to hit 8 figures. Dinah shares how she built the company from her garage while juggling motherhood and a demanding corporate job, why she resisted shortcuts in customer service, and how she turned customer feedback into a growth engine.Here's a glimpse of what you'll learn:Moving abroad while running a U.S.-based businessStarting Little Trouble as a side hustle during corporate burnoutKnowing when a side hustle becomes a full-time businessStanding out in a crowded kids apparel marketChallenges across growth stages: 0–1M, 1–5M, and beyondOperating with a tiny team while scaling bigThe critical role of customer service and human connectionThe pitfalls of over-obsessing about attribution vs. focusing on fundamentalsLeveraging customer insights and zero-party data for growthWhat’s next: brand collaborations, wholesale, and product diversificationFind more episodes on ⁠⁠⁠⁠our website⁠⁠⁠⁠.--This episode is brought to you by ⁠⁠⁠⁠BSR Digital⁠⁠⁠⁠.⁠⁠⁠⁠BSR Digital⁠⁠⁠⁠ helps e-commerce brands that want to scale their business to the next level through paid ads & email marketing.To learn more about BSR Digital, ⁠⁠⁠⁠visit their website⁠⁠⁠⁠ or book a call ⁠⁠⁠⁠here⁠⁠⁠⁠.

In this episode of The DTC Insider podcast, Brian Roisentul chats with Dinah Chapman, founder of Little Trouble, a fast-growing kidswear brand that’s on track to hit 8 figures. Dinah shares how she built the company from her garage while juggling motherhood and a demanding corporate job, why she resisted shortcuts in customer service, and how she turned customer feedback into a growth engine.Here's a glimpse of what you'll learn:Moving abroad while running a U.S.-based businessStarting Little Trouble as a side hustle during corporate burnoutKnowing when a side hustle becomes a full-time businessStanding out in a crowded kids apparel marketChallenges across growth stages: 0–1M, 1–5M, and beyondOperating with a tiny team while scaling bigThe critical role of customer service and human connectionThe pitfalls of over-obsessing about attribution vs. focusing on fundamentalsLeveraging customer insights and zero-party data for growthWhat’s next: brand collaborations, wholesale, and product diversificationFind more episodes on ⁠⁠⁠⁠our website⁠⁠⁠⁠.--This episode is brought to you by ⁠⁠⁠⁠BSR Digital⁠⁠⁠⁠.⁠⁠⁠⁠BSR Digital⁠⁠⁠⁠ helps e-commerce brands that want to scale their business to the next level through paid ads & email marketing.To learn more about BSR Digital, ⁠⁠⁠⁠visit their website⁠⁠⁠⁠ or book a call ⁠⁠⁠⁠here⁠⁠⁠⁠.

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From Corporate Burnout to 8 Figures: The Story Behind Little Trouble

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This episode was published on August 22, 2025.

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In this episode of The DTC Insider podcast, Brian Roisentul chats with Dinah Chapman, founder of Little Trouble, a fast-growing kidswear brand that’s on track to hit 8 figures. Dinah shares how she built the company from her garage while juggling...

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