The Side Hustle Show

Cheyenne Bullock, the innovative founder of Domestic Daydreams, transformed vintage public-domain radio shows into a unique subscription service that combines audio cleaning routines with nostalgic entertainment. She shares how her $25/month membership attracts over 500 members by leveraging Instagram for marketing and organic growth. Cheyenne discusses vital strategies like high-volume content posting, effective email follow-ups, and simplifying membership offerings to boost retention. Her heartfelt customer stories highlight the positive impact on families, showcasing the emotional connection built through her creative business.

Nathan Barry, a serial entrepreneur and founder of ConvertKit, shares his journey from flipping burgers to generating $2.5M monthly in software revenue. He introduces his 'Ladders of Wealth Creation' framework, highlighting the pivotal four ladders that build skills for wealth. The conversation covers adding new income streams, project pricing strategies, and the importance of service-based businesses in professional growth. Barry discusses his focus on productization and shares marketing strategies that boosted ConvertKit's revenue, offering valuable insights for aspiring creators.

Summer Rae, the founder of Soma Lumen and aura photography entrepreneur, shares her journey of generating $70,000 in just six months while juggling a full-time job. She discusses how strategic partnerships and event participation, like festivals, drove customer flow, enabling her to sell sessions at $44 each. Summer also reveals her innovative aura-capture technology and emphasizes creating emotional connections through her work. She highlights the importance of starting imperfectly and iterating for success in any side hustle.

Jeff Rose, a financial entrepreneur and creator of Good Financial Sense, shares how he's raked in over $1,000 daily by posting viral content on Facebook. He explains the ins and outs of Facebook's monetization program and the surprising types of posts that gain traction—think finance charts and humorous memes. Jeff reveals his strategies for sourcing viral content, including using Twitter and Threads for inspiration, and how he efficiently schedules posts to save time. With tips on dealing with toxic comments and boosting posts, Jeff's insights could have you cashing in on your own Facebook side hustle.

Unlocking the secrets of effective marketing! Discover innovative strategies like leveraging social media algorithms to build your email list, employing quizzes for personalized product recommendations, and automating email growth with clever tools. Learn how to boost your local visibility through timely Google reviews and optimize outreach with direct mail and referrals. Explore unique ideas, from using niche Reddit forums for traffic to repurposing content using AI for maximum engagement. These tips are gold for any side hustler!

Holly Finnefrock, founder of a high-ticket dropshipping business, shares her journey to $500K in sales in just six months. She reveals how competitor analysis helped her choose the pond and water feature niche. Holly discusses the benefits of high-ticket items and her relationship-building strategies with suppliers. From crafting Google Ads focused on bottom-of-funnel buyers to handling different customer types, she outlines her path to success. Tune in for insights on niche validation, supplier negotiations, and scaling a dropshipping business.

Jennifer Marx, the founder of JenniferMaker.com, transformed her DIY blog from a humble hobby into a six-figure powerhouse. She shares her journey from earning just $33 in her first month to generating $100k monthly. Discover how she leveraged Pinterest for traffic, built a massive email list of 375,000, and created a diverse revenue stream through courses and products. Jennifer emphasizes the power of community engagement and the importance of finding fresh content ideas. Tune in for her top tips on promoting content and overcoming early struggles!

Anthony Kolodziej, the mastermind behind H&H Vending, scaled his business to over $50k per month in just 16 months. He shares his unique 'parking lot test' for scouting locations and emphasizes that raw dollar profit trumps percentage margins. Learn how to compete with large vendors through better tech and service, and discover strategies for hiring and trimming routes to boost profitability. Anthony also discusses the importance of patience in selecting locations and treating machines as valuable assets.

Samantha Hamilton, founder of Dottie for Running, turned a homemade Disney-inspired tutu into a thriving running skirt business, ultimately selling it for $120,000. She shares how she navigated production challenges, built a loyal community through social media and ambassadorship, and effectively managed demand spikes. Samantha discusses the transition from Etsy to Shopify for scalability and her crucial decision to sell for family reasons. Her advice? Start small and believe in your vision!

In this engaging discussion, Gloria Riley, creator of YellowLlamaCo, shares her journey transforming a hobby into a thriving business designing planners for Sims enthusiasts. She recounts her shift from low sales to viral success on TikTok, driven by a creative physical planner. Gloria unveils strategies for pricing, marketing, and developing digital products, including her flagship Notion template, SimGuardian. She emphasizes the importance of community engagement and the balance between content creation and business growth.