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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What happens when your husband's hobby turns into a full-blown business empire? Meet Jess Loseke, CEO of Midwest Barrel Company, who took a leap into the bourbon barrel industry and never looked back.
In this episode, Jess gets real about the gritty side of entrepreneurship—from navigating cash flow chaos in an inventory-heavy business to working shoulder-to-shoulder with her spouse (and staying married through it). We talk leadership, scaling, e-commerce, and why relocating to Kentucky was the bold move that changed everything.
If you’re building a business from scratch, wrestling with growth, or just curious about how to turn a niche idea into a powerhouse brand, this episode is your shot of straight bourbon wisdom—no chaser.
🔥 Key Topics:
- Entrepreneurship without a safety net
- Cash flow management in inventory-based businesses
- E-commerce and email marketing strategies
- Leadership dynamics with your spouse
- Risk-taking and relocating for growth
- Building culture while scaling
- Expanding into international markets
- Sustainability and future plans
🔑 SEO Keywords:
Midwest Barrel Company, bourbon industry, e-commerce, entrepreneurship, business scaling, leadership, cash flow challenges, partnerships, business growth, Kentucky bourbon barrels, sustainability in business, working with your spouse
💬 Sound Bites:
- “Working with your spouse is not for everyone.”
- “I want to quit sometimes, but I don’t.”
- “It was a calculated risk—but the right one.”
📌 Chapters:
00:00 – Podcasting Adventures and Networking
00:44 – The Journey of Midwest Barrel Company
08:23 – Overcoming Personal Challenges
17:20 – Navigating Business Decisions and Partnerships
22:43 – Cash Flow Management and Economic Challenges
26:55 – Transitioning to a New Facility
29:14 – Navigating Leadership Dynamics
34:36 – Scaling Strategies and Market Expansion
40:41 – Overcoming Entrepreneurial Challenges
46:13 – Taking Risks and Future Vision
💥 Want a free merch or brand audit? Just ask. No pressure, just people helping people.
👉 Perch-Merch.com
👉 OhHelloAgency.co
🔗 Connect with Us:
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