Side Hustle School

Chris Guillebeau / Onward Project
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4 snips
Jan 23, 2026 • 10min

Ep. 3310 - Failure Friday: “We were incredibly disappointed…”

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.
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4 snips
Jan 22, 2026 • 7min

Ep. 3309 - TBT: “MomBox” Expands to Popular Subscription Box Service

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.
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Jan 21, 2026 • 4min

Ep. 3308 - Q&A: “What are the ethics of paid referrals to therapists?”

A listener digs into the ethics of earning commissions by referring their YouTube followers to therapists. They explore the necessary legalities and disclosure practices involved in such partnerships. The discussion highlights the importance of transparency with both viewers and therapists to prevent conflicts of interest. Suggestions include collaborating with established therapy platforms for smoother logistics. Practical tips on how to pitch partnership opportunities are also provided, making it a rich resource for aspiring side hustlers.
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Jan 20, 2026 • 5min

Ep. 3307 - Q&A: “Should I charge a flat fee or percentage?”

Bettina Smelser, a savvy reseller from Gettysburg, Pennsylvania, shares her insights on selling items through Facebook Marketplace with her teenage son. She seeks advice on whether to charge a flat fee or a percentage for consignment sales. The discussion highlights the benefits of charging a percentage to align incentives and ensure profitability. Chris also emphasizes the importance of setting a minimum fee and managing client expectations to exceed seller's hopes. Tune in for practical tips to kickstart your own consignment venture!
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6 snips
Jan 19, 2026 • 8min

Ep. 3306 - First $1,000: “The pre-launch brought in $1,000 on day one…”

Join Becky Hoy, the founder of BraveCrate and a military spouse, as she shares her inspiring journey of launching a deployment countdown subscription box. She discusses how she earned $1,000 on launch day through effective pre-launch marketing and building a supportive community. Becky highlights her strategies of engaging military spouses via social media, forming partnerships, and using a lead magnet to grow her email list. Her insights on validating business ideas before investing are invaluable for aspiring entrepreneurs!
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Jan 18, 2026 • 7min

Ep. 3305 - STORY: Engineer Makes $80,000/Year Handing Out Free Maps

A former sound engineer turns his passion into profit by creating local maps for hotel guests. These colorful guides feature advertisements from local businesses, generating around $80,000 a year. The model not only helps travelers but also boosts hotels and local merchants, creating a win-win situation. Plans for franchising the map business are in the works, allowing for broader expansion. This story highlights the creativity and financial potential of turning a simple idea into a thriving side hustle.
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6 snips
Jan 17, 2026 • 5min

Ep. 3304 - Q&A: “Is it better to have more projects or a single focus?”

Laura, a curious listener diving into the world of side hustles, asks about balancing multiple projects versus focusing on one. Chris shares insights on experimenting with several ideas before committing to a main hustle and a secondary fun project. He discusses the merits of diversification for income streams while also highlighting the power of focused effort in achieving goals. The conversation balances practical advice with encouraging listeners to find their personal approach to side hustling.
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5 snips
Jan 16, 2026 • 6min

Ep. 3303 - STORY: Food Tour Guide Chomps Down on $100,000 Profit

A former marketer pivoted from private cooking lessons to launching a successful food tour company. She started with a modest $3,000 and quickly gained traction, earning $200,000 in a year with $100,000 profit. Her innovative approach included forming partnerships and rapidly scaling her business by hiring additional guides. With newfound freedom and flexibility, she expanded her offerings to include cocktail tours, enhancing her side hustle while enjoying the perks of travel and financial independence.
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Jan 15, 2026 • 7min

3302 - TBT: Mystery Trip Biz Doubles Down on Thrills

Dave Green, the creative mastermind behind Mystery Trip, shares how he transformed a casual friends' gathering into a thriving event planning business. He discusses the shift to virtual experiences during the pandemic, including trivia and scavenger hunts, and previews the innovative hybrid game 'Minute to Win It'. Dave reflects on his remarkable projects, like recreating the 'We Are The World' music video, and emphasizes the importance of embracing change in business. With in-person events returning, he looks forward to a balanced future of hybrid offerings.
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Jan 14, 2026 • 5min

Ep. 3301 - Q&A: “How do songs get licensed for background music?”

An independent musician shares struggles with dismal Spotify royalties. The discussion shifts to the potentially lucrative world of background music licensing. Insights reveal how agencies can enhance earnings by matching tracks to corporate needs. The podcast highlights the value of creating instrumental pieces specifically designed for background play. Additionally, there's advice on maintaining a presence on streaming platforms to optimize reach. A blend of creativity and strategy is suggested for aspiring musicians!

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