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

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⏱️ 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

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🔑 Key Points

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  Why vending by the cup keeps you stuck

  
  


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  The exact moment Jenna knew she could go full time

  
  


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  How to systemize before you scale

  
  


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  A practical delegation exercise you can try today

  
  


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  Why stepping back might be the key to growth