27. What 300 Events Taught Jenna Jackley (Bloom Coffee)

In this episode, we sit down with Jenna Jackley, founder of Bloom Coffee in Nashville, to unpack how she grew from a garage-built cart to running 300+ events a year. You’ll learn how she made the leap from side hustle to full-time, the mistakes she made in her first year, and the sticky note exercise that transformed her business. Jenna shares exactly when she knew it was time to hire, how she transitioned away from vending to prepaid events, and the systems that helped her finally delegate and scale. Whether you’re just starting out or looking to get out of the “hands dirty” phase, this episode will show you how to build a cart business that can run without you. 👉 Want our FREE step-by-step playbook for streamlining your bookings? Grab our free guide here: flashquotes.com/software-tools ➡️ Join our Mobile Catering Accelerator: https://www.skool.com/mobile-catering-accelerator/about 📸 Instagram: @FlashquotesHQ 🐦 Twitter: @FlashquotesHQ ⸻ ⏱️ Timestamps 00:00 – Welcome + Jenna’s early days with FlashQuotes 02:18 – Starting Bloom Coffee in a garage during the pandemic 03:52 – Breaking even fast and realizing this could be full-time 04:36 – The leap from side hustle to full-time business 06:07 – Surviving the “early slog” of long hours and low pay 08:55 – Why she quit vending events and focused on prepaid bookings 10:38 – Why Bloom Coffee never wanted a brick-and-mortar 11:26 – Who shouldn’t start a mobile cart business 13:42 – Building systems before the busy season snowball hits 16:12 – Thinking like a founder: how Jenna started stepping back 17:02 – Promoting from within and finding her right-hand person 19:17 – The hardest part of letting go (and how she managed it) 21:18 – The sticky note exercise that changed everything 22:41 – Testing her team by running events while she was in Paris 23:36 – How delegation unlocked new growth and freedom ⸻ 🔑 Key Points Why vending by the cup keeps you stuck The exact moment Jenna knew she could go full time How to systemize before you scale A practical delegation exercise you can try today Why stepping back might be the key to growth