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

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 business

• Starting Little Trouble as a side hustle during corporate burnout

• Knowing when a side hustle becomes a full-time business

• Standing out in a crowded kids apparel market

• Challenges across growth stages: $0-$1M, $1-$5M, and beyond

• Operating with a tiny team while scaling big

• The critical role of customer service and human connection

• The pitfalls of over-obsessing about attribution vs. focusing on fundamentals

• Leveraging customer insights and zero-party data for growth

• What’s next: brand collaborations, wholesale, and product diversification
  

Resources mentioned in this episode:

• BSR Digital

• Subscribe to The DTC Insider weekly newsletter

• Brian Roisentul on LinkedIn

• Dinah Chapman on LinkedIn

• Little Trouble's website

  
  

Sponsor for this episode:

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.