Business Over Cocktails - Behind the Business - Real Talk with Female Entrepreneurs
Welcome to Business Over Cocktails — the podcast where female entrepreneurs, founder stories, and soulful business growth take center stage.
Hosted by business strategist and community builder Lauren Najar, this show dives into the “why” behind the business, the real stories behind entrepreneurship, and the pivotal moments that shape women-led brands.
Expect candid interviews with creative entrepreneurs, behind-the-scenes reflections on small business growth, and bite-sized solo episodes inside The Business Chaser — where we explore authentic visibility, organic marketing, and building a business that actually feels good.
Whether you're scaling a service-based business, navigating a pivot, or craving real talk for entrepreneurs, this is your spot.
Pull up a seat. Pour your favorite drink. Let’s talk business.
Business Over Cocktails - Behind the Business - Real Talk with Female Entrepreneurs
How a Childhood Around Business Shaped Her Work w/ Jessica Wilson
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Jessica Wilson grew up surrounded by entrepreneurs, where “playing office” as a kid turned into a lifelong love for the numbers behind the scenes. In this episode, she shares how the women in her family taught her the power of bookkeeping, why financial clarity brings peace, and what it really means to hold space for business owners who feel overwhelmed by their finances. Whether you're scaling or just starting, this conversation will leave you feeling seen, steady, and ready to look at your numbers without fear.
Episode Highlights:
- Jessica’s early exposure to entrepreneurship and how it shaped her love for bookkeeping
- The generational wisdom passed down from the women in her family
- Why bookkeeping is more than numbers—it’s about trust, clarity, and peace
- Common misconceptions about bookkeepers (and why Jessica breaks the mold)
- The mindset shift every entrepreneur needs to build a healthier relationship with money
Chapters:
[00:00] Meet Jessica: The Bookkeeper Who’s Anything But Boring
[03:00] Childhood in the Office: Where It All Began
[07:30] From College to Career: Building a Purpose-Driven Business
[13:00] Shame, Money, and Why Numbers Feel So Personal
[18:45] Misconceptions About Bookkeepers (And What We Actually Do)
[25:00] Client Wins, AI Tools, and the Future of Financial Support
[36:00] Building Confidence, Finding Peace, and Empowering Others
Connect with Jessica Wilson:
Website: https://designedledgers.com/
Instagram: https://www.instagram.com/designedledgers/
Let’s Stay Connected:
→ Follow Lauren on Instagram: www.instagram.com/laurennajar
→ Learn more or work with me: www.laurennajar.com
→ Follow Business Over Cocktails on IG: www.instagram.com/businessovercocktails
→ Attend Growth & Connect retreats & events: www.instagram.com/growthandconnect
🎧 Subscribe & Review:
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