Welcome to the Bag Season Podcast 🎙️
Wins. Losses. Lessons. Real Business.
Welcome to the Bag Season Podcast, where we have honest conversations about what it really takes to build, scale, and survive in business. This isn’t just highlight reels and success stories—we dig into the wins, the losses, the mistakes, and the lessons learned along the way.
From startups and blue-collar businesses to real estate, clean energy, tech, and entrepreneurship, Bag Season explores what happens behind the scenes when people are chasing growth, opportunity, and generational wealth.
If you’re building something—or thinking about it—this podcast is for you.
What We Talk About
- 💼 Business wins and business failures
- 📈 Scaling companies and managing growth pains
- 💸 Money, margins, and cash-flow realities
- 🧠 Leadership, mindset, and decision-making
- 🛠️ Blue-collar, service, and trade-based businesses
- ⚡ Energy, HVAC, construction, real estate, and emerging sectors
- 🧾 Lessons learned the hard way—so you don’t have to
No fluff. No fake gurus. Just real conversations from people who’ve been in the trenches.
Meet the Hosts
🎤 Brynn Cooksey — “The Air Doctor”
Brynn Cooksey, known throughout the trades and energy-efficiency world as The Air Doctor, is an HVAC contractor, building science expert, educator, and entrepreneur. As the owner of multiple businesses and training platforms, Brynn brings real-world experience from scaling companies, training thousands of technicians, and navigating the highs and lows of entrepreneurship.
Brynn’s perspective is rooted in:
- Blue-collar business ownership
- Workforce development and training
- Energy efficiency and building science
- Leadership, community impact, and long-term wealth building
He’s not just talking theory—he’s lived it.
🎤 Dan Ringo — “Airman Dan”
Dan Ringo brings a sharp business mindset and a no-nonsense approach to strategy, execution, and growth. His professional journey has earned him several on-air nicknames, each revealing a different dimension of his expertise:
- “Airman Dan”
Dan discusses military experiences and how they’ve shaped his personal and professional journey. - The Boardroom Engineer”
A reflection of Dan’s rare combination of skilled-trades depth and executive leadership. He understands business from the boiler room to the boardroom and breaks down complex systems with precision. - “Rubberband Dan”
Symbolizing resilience and reinvention. Dan has stretched, snapped back, rebuilt, and leveled up across multiple careers—and brings that same bounce-back philosophy to entrepreneurs facing real-world challenges. - “The Executionist”
Strategy means nothing without action. Dan is the voice that pushes conversations from “big ideas” to “real deliverables,” ensuring listeners get practical, applicable insight.
Dan’s voice on the podcast centers around:
- Business fundamentals and strategy
- Risk, reward, and calculated decisions
- Market realities across industries
- Keeping conversations grounded and actionable
Together, Brynn and Dan balance vision with execution—and they’re not afraid to challenge each other.
Why “Bag Season”?
Because every season in business is different.
- Sometimes you’re stacking wins.
- Sometimes you’re taking losses.
- Sometimes you’re rebuilding, retooling, or starting over.
Bag Season is about recognizing where you are, learning from every phase, and staying in the game long enough to win.
Tune In
New episodes feature candid discussions, guest interviews, and real stories from business owners, operators, and leaders across industries.
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