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From launching a babysitting hustle at 16 to building two successful startups, Gen George’s journey is all about bold ideas and solving real-world problems. 🚀

In this episode, the co-founder of LMBDW (Like-Minded B*****s Drinking Wine) and founder of tamme, Skilld and OneShift joins us to share how she built and scaled multiple businesses, the lessons she learned along the way, and her insights on hiring, scaling, and the future of work.

In today’s episode, we cover:

✅ Early entrepreneurial ventures – How Jen’s childhood exposure to business shaped her mindset, from working in her parents’ factory to launching her first side hustle.

✅ From university dropout to startup founder – Why traditional education wasn’t the right path, and how her gap year led to unexpected business opportunities.

✅ Building OneShift & Skilled – The story behind launching her first marketplace startup, securing $5M in funding, and later pivoting to Skilled, a platform revolutionizing hiring for small businesses.

✅ Scaling a two-sided marketplace – Lessons on balancing supply and demand, leveraging AI for matchmaking, and overcoming hiring challenges in the service industry.

✅ Growth strategies & traction – From old-school flyer marketing to real-time ad optimization, the marketing playbook that took Skilled to 120,000 users in just six months.

✅ Startup culture & leadership – Why hiring for adaptability matters, how to foster a culture of experimentation, and the key traits she looks for in a team.

Jen also shares her thoughts on the gig economy, what it takes to scale a lean startup, and her best advice for founders navigating the early stages of business.

Resources & Links:

👋 Gen George: linkedin.com/in/gengeorge👋 Harry Uffindell: linkedin.com/in/harrisonuffindell🎧 Apple Podcasts🎧 Spotify

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