Reach Out Via Text!

In this episode, Jeremiah Jennings dives into one of the most overlooked transitions in business: stepping out of the field and into the role of an owner. He unpacks the emotional weight that comes with leaving behind the hands-on work you love, and why that shift can feel more like grief than growth. Jeremiah shares personal experiences—from early days working alongside friends to losing a key team member due to miscommunication—and highlights the hidden tension that builds when leadership roles aren’t clearly communicated.

The episode breaks down the real responsibilities of running a growing company, from sales and financial management to team leadership and personal development, emphasizing that this “invisible work” is often misunderstood by crews. He also provides practical strategies to close the perception gap with your team through transparency, communication, and appreciation.

Ultimately, this conversation is a real, honest look at what it takes to grow a business the right way—without losing your team, your identity, or your passion for the craft

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Reach Out Via Text!

In this episode, Jeremiah Jennings breaks down one of the most critical (and often overlooked) systems in a landscape business—accurate estimating. He dives deep into why most contractors are unknowingly losing money, not because they aren’t winning jobs, but because they don’t truly know their numbers. Jeremiah walks through the power of production rates, how to actually build them in the field, and why templates are the key to speed and consistency in your estimating process. He also opens up about real mistakes he’s made—jobs that doubled in labor time—and how those lessons shaped his current systems. To wrap it up, he shifts to the front end of the business, highlighting how poor lead intake and slow response times are costing companies thousands in missed opportunities. This episode is a practical, no-fluff guide to tightening your systems, protecting your margins, and scaling with confidence.

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Reach Out Via Text!

Are you using AI or different technologies in your business in 2026? If not, what are you waiting for? The next 2-5 years are going to change the world in every aspect with the development of technology. Will you adapt and bring it into your operations or just watch everyone else and fall behind?

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Reach Out Via Text!

In this episode, Jeremiah comes to you live from Raleigh, North Carolina, while on a John Deere facility tour, but quickly pivots into a real and vulnerable conversation about something many business owners face, team burnout. He opens up about challenges within his own company, specifically around uncommunicated expectations, lack of clarity, and how leadership gaps can unintentionally create strain on a small team.

Jeremiah breaks down the realities of running a small business, where everyone wears multiple hats, and explains how the very traits that make small teams great, grit, loyalty, and flexibility, can also put them at risk. He shares practical signs to watch for when burnout is creeping in and emphasizes the importance of proactive communication before it’s too late.

Throughout the episode, he takes ownership as a leader, outlining specific changes he’s making, including more intentional conversations, clearer vision casting, and celebrating wins more consistently. This is a raw, honest look at leadership responsibility, culture, and protecting your people—not just your production.

If you’re growing a team or in the trenches of business ownership, this episode is a direct challenge to lead better, communicate more, and protect what matters most—your people.

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Reach Out Via Text!

In this episode, Jeremiah dives into a real-time breakdown of a large commercial landscaping project his company is currently executing, sharing lessons learned under pressure. He unpacks how the commercial construction world actually works—from understanding the role of a general contractor to navigating bidding, scope writing, and relationship-building that can win jobs even without being the lowest bid. Jeremiah also gets honest about the financial realities, including cash flow challenges, net payment terms, and the importance of having reserves or credit in place. Throughout the episode, he highlights critical operational insights like handling change orders, managing deadlines, and avoiding costly mistakes on-site. If you’re looking to break into commercial work or scale your landscaping business, this episode delivers practical, hard-earned advice you can apply immediately.

Cultivated Podcast- https://podcasts.apple.com/us/podcast/cultivated/id1871971706

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Reach Out Via Text!

In this episode of the Growing Green Podcast, Jeremiah sits down with Pat Murray of Local Roots to unpack a powerful and raw conversation around leadership, burnout, and building a sustainable business. Pat shares the behind-the-scenes reality of scaling a $10M landscaping company, including the intentional shift toward recurring maintenance revenue and the operational complexity that comes with growth. The conversation takes a deeper turn as Pat opens up about hitting a breaking point, navigating burnout, and ultimately stepping away for a sabbatical to recover and reset. Together, they discuss the importance of defined roles, asking for help, and building a business that doesn’t rely solely on you. They close with practical strategies for setting boundaries, avoiding chronic stress, and leading effectively through the demands of a growing company.

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Reach Out Via Text!

Derek Clelan went from filing bankruptcy at 24 to building one of the fastest-growing landscape design firms in the country — and he did it in just three years. In this conversation recorded live at LeanScapers in Cape Coral, Jeremiah sits down with Derek to unpack the origin story of Your Haven Design, how they completed 1,500 designs for over 400 contractors across the US, UK, and Canada in a single year, and why design isn't just a deliverable — it's a sales tool, an estimating tool, and a feedback loop all in one. They dig into Your Haven's membership model, how AI is creeping into the design workflow (without replacing the humans doing the actual work), and the bold plan to build a full Design Academy that trains and employs the next generation of landscape designers. If you're a contractor on the fence about adding design to your process, this one will settle it.

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Reach Out Via Text!

What happens when a college kid with zero landscaping experience, a co-signed truck, and 30 days to make his first payment decides to bet on himself? You get one of the most honest, hard-won stories in the green industry.

In this episode, recorded live at the Landscaper Revenue Intensive in Cape Coral, Florida, host Jeremiah Jennings sits down with Jeremy Talboy of North Georgia Landscape Management for a raw, no-highlights-reel conversation about what it actually takes to build a landscaping company from scratch.

Jeremy T. opens up about scaling from $1M to $5M in under two years — only to accumulate staggering debt, lose operational control, and nearly watch it all fall apart. He shares how he hit the brakes, installed real systems, plugged the holes, and clawed his way back to sustainable growth approaching $8.5M.

In this episode:

• Why starting during a recession was actually a hidden advantage
• The moment a co-signed truck made entrepreneurship feel real
• How rapid growth without systems nearly destroyed the business
• Building commercial maintenance from zero — and losing money to win market share
• The power of communication with lenders, clients, and your team when things go sideways
• Why documenting the lows matters just as much as celebrating the wins

Whether you're just starting out or you're stuck in the messy middle, this one will remind you: you're not alone and the path forward is always through, never around.

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Support the show

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• Email-ggreenlandscapes@gmail.com
• Growing Green Website- https://www.growinggreenlandscapes.com/