Side Hustle School

Tara, a listener who asked about selling locally on Nextdoor. The conversation covers when neighborhood apps work best, practical tips like clear photos and detailed listings, and how Nextdoor compares to Craigslist and Marketplace. Short, actionable advice for hyper-local pickup sales.

A DIY training tool idea grows from backyard tinkering into a production-ready fitness product. The creator uses Kickstarter to validate demand and secures major funding. He navigates factory sourcing, travel to inspect samples, and scales to steady monthly sales. Lessons focus on prototyping, manufacturing vigilance, and fulfillment challenges.

Kristen Barry Massoris, a graphic designer who built Miss Design Barry into a seven-figure custom wedding-illustration brand. She shares how she launched on Etsy, raised prices and moved to a direct site, and used niching and coaching to reach high-value clients. She also discusses scaling beyond Etsy, building new product lines, and partnering with charity.

Elsa, an Etsy seller from Seattle, calls in seeking a Shopify transition. The conversation covers why Shopify offers flexibility while Etsy provides built-in traffic. Tips include keeping Etsy open during the switch, learning Shopify hands-on, and avoiding dependence on others for simple site changes.

Alonzo, a listener from Pensacola, calls in seeking the best tools to write a nonfiction book. They discuss why outlining first helps, how Scrivener organizes sections and manuscripts, and other options like Google Docs, Notion, Ulysses, or even longhand. There is also a reminder to limit distractions from social media while writing.

Jodi Carlson, creator of Leader Connecting Leaders who makes resources for Girl Scout troop leaders. She turned a hobby into income by selling printable badge programs. The conversation covers how she found buyers, built an email list and social channels, added direct sales to her site, and the moment a bulk purchase pushed monthly revenue past $1,000.

A laid-off government worker turns a free clothes dryer into a repeatable reselling system. The story follows discovering Craigslist, quick listing tactics, and cleaning and photo tricks that speed sales. Strategies for scaling from small flips to five-figure months and beyond are highlighted.

A Q&A about turning legal fine print into a paying side project. Discussion covers why people ignore T&C and how companies craft them. Ideas include designing reusable T&C templates, pricing and marketing that product, and whether brands would pay for simplified clauses. Alternatives explore educating consumers and focusing on clear customer demand.

In this engaging discussion, Jay Perkins, the founder of Kettlebell Kings and a lifestyle fitness blogger, shares his rollercoaster journey in e-commerce. He reveals the challenges of launching his import business while balancing rideshare work and software gigs. When a significant shipment went awry, resulting in a $25,000 loss, Jay had to navigate customer refunds and re-establish trust. He emphasizes vital lessons on quality control, supplier relations, and the importance of resilience in overcoming entrepreneurial setbacks.

In this session, Kate Westervelt, founder and former CEO of MomBox, shares her journey from overwhelmed new mom to e-commerce innovator. She reveals how a labor recovery kit transformed into a comprehensive 12-month subscription service for postpartum support. Kate discusses expanding product offerings, including a breastfeeding support box, and emphasizes the importance of sourcing from female and BIPOC-founded companies. She also reflects on her company's recent acquisition and shares invaluable advice for aspiring entrepreneurs.