Ep. 22 The Stern Truth: Business Therapy Thursday with Jessica Lowen

THE STERN TRUTH: Business Unfiltered

THE STERN TRUTH: Business Unfiltered
Ep. 22 The Stern Truth: Business Therapy Thursday with Jessica Lowen
Jul 03, 2025 Season 1 Episode 22
Marshall Stern

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It’s another Business Therapy Thursday Session! In this powerful episode, I sit down with Jessica Lowen, founder of TM Events and Promotions, for an unfiltered deep dive into a familiar challenge small business owners face. That critical time when you make the leap from solo entrepreneur to employer.

As a small business owner running her event planning and staffing agency single-handedly for eight years, Jessica is at a critical crossroads. She knows she needs to hire support staff. She's drowning in administrative tasks, feeling overwhelmed, but the fear of hiring her first employee is paralyzing her growth.

I walk Jessica through what the familiar "Energy Audit". Regular listeners of the Stern Truth will be familiar with it but what we do is identify which activities drain you versus energize you as an entrepreneur. 

What Jessica and I uncovered during our session is that a whopping 50% of her workday goes to tasks like bookkeeping, invoicing, hiring, and social media management. These are ALL things that could, and should, be delegated to an assistant.

We explore the loneliness of being a one-person show, along with the control issues that plague small business owners. Jessica and I explore the importance of trusting yourself, and why it’s just as important as trusting others when building your team.

This episode is raw, honest, and deeply relatable for any founder who's ever felt scared to take that next step. I hope this episode makes any other small business owners looking to scale beyond yourself feel seen, heard, and less alone.

 

I’m excited to bring back the ONtreprenur Bonfire Series. It’s a ZERO cost series starting in August running for 4 weeks. Email me to get your spot before they’re gone - Marshall@marshallstern.net.

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I encourage you to reach out with feedback, topic suggestions, and share your own entrepreneurial challenges.

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