The Ultimate Landscape CEO - Jeffrey Scott

In this episode, Jeffrey Scott steps away from traditional business strategy to explore a more intentional and sustainable approach to personal goal setting for the new year. Rather than relying on reactive New Year’s resolutions, Jeffrey explains why they often fail and introduces a simple but powerful framework built around four core questions: Who do you want to be? What do you want to do? Where do you want to go? And what do you want to have? Drawing from personal experiences, travel aspirations, family life, health goals, and leadership growth, he shares how aligning personal goals with purpose creates clarity, focus, and long-term momentum. Jeffrey also emphasizes the importance of pacing, prioritization, accountability partners, and borrowing proven business tools like quarterly goals and OKRs to support personal development in 2026 and beyond.

Takeaways:

Personal goal setting vs. New Year’s resolutions
The “Be, Do, Go, Have” goal framework
Aligning personal purpose with professional growth
Simplifying goals to avoid overwhelm
Using quarterly prioritization for personal goals
The role of environment, travel, and exposure in growth
Accountability partners and shared goal setting
Removing negative influences to sustain progress

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In this episode, Dan Simpson, Manager of Product Marketing at Fleetio, joins Jeffrey Scott to break down why fleet and equipment management is one of the most overlooked — yet most volatile — cost centers in landscaping and contracting businesses. Dan shares insights from his hands-on background in construction and years working directly with fleets, explaining how better visibility, preventative maintenance, inspections, fuel tracking, and data-driven decisions can dramatically reduce breakdowns, control costs, and protect margins. The conversation dives into why landscaping companies are also “in the fleet business,” how software and data turn gut-feel decisions into confident ones, and where AI and automation are heading in fleet management.

Takeaways:

Fleet management as a hidden profit lever
Preventative maintenance vs. reactive repairs
Inspections and communication from the field
Fuel cost visibility and control
Total cost of ownership for vehicles and equipment
Reducing downtime and breakdown volatility
Tracking tools, assets, and accountability
Using data to make smarter equipment decisions
Integrations with accounting and ops software
The future of AI and automation in fleet operations

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In this episode, Jeffrey Scott addresses the critical relationship between budgeting and business strategy for landscape company CEOs planning for 2026. He identifies a fundamental problem: too many companies treat budgeting as a checkbox exercise rather than a confirmation of their strategic direction. Drawing from his consulting experience with landscape businesses, he walks through ten common disconnects between budgets and operational reality—from unclear owner objectives to poor equipment management and weak cash flow planning. His core message is that effective budgeting requires intentional decision-making about what kind of company you’re building, whether that’s a lifestyle business, a growth company, or a sellable asset, and every financial decision should reinforce that goal.

Takeaways:

Strategy-Budget Alignment: Budgets should confirm your business strategy, not exist as separate exercises disconnected from how you actually run the company
Revenue as Capacity-Driven: Revenue planning must be based on actual labor capacity and billable hours, not aspirational goals or ego-driven milestones
Detailed Gross Profit Analysis: Break down gross profit margins by division and service type rather than using global averages to uncover hidden opportunities and blind spots
Subcontractor Markup Strategy: Different subcontractors require different markups based on management intensity and how integrated their work is into your final product
Owner Compensation Planning: Treat owner compensation as a planned business cost with market-based pay plus return on capital, not as whatever’s leftover
Cash Flow as Separate Strategy: Develop a dedicated cash management strategy including better contract terms, collections processes, and vendor negotiations to ensure the business can sustain itself

The post Aligning Budgets with Business Strategy: 10 Key Insights with Jeffrey Scott appeared first on Jeffrey Scott.

This is a replay of a previous episode featuring Wade and Dustin Vugteveen, owners of DeHamer Landscaping, a $10M+ landscaping firm based in Grandville, Michigan.

They do a mix of snow, maintenance, landscape and irrigation.

We discuss their history of startups, first with a baseball training business and then in retail.

We discuss how hard it was for them early on, and how difficult it is to grow a business as an entrepreneur.

These two have taken a series of risks over and over again, which has allowed them to scale their business quickly. Business is more of a “calling” for them as a people-first company.

You will enjoy stories and their ride.

Apply for our Leaders Edge Peer Group Here.

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Join Jeffrey Scott for an insightful conversation with two leaders from Aspire: Mark Tipton, co-founder and former CEO, and Eli Zevin, the current General Manager. Mark shares his 12-year journey building Aspire from a skunkworks project into the leading landscape business management software, while Eli discusses his transition from Service Titan and his vision for Aspire’s AI-powered future. This episode explores leadership transitions, scaling software companies, company culture, implementation challenges, and the revolutionary role of artificial intelligence in transforming the landscape industry.

Takeaways:

Mark Tipton reflects on his 12-year journey with Aspire.
Eli Zevin emphasizes the importance of client success.
The legacy of Kevin Kehoe has shaped Aspire’s culture.
Leadership requires navigating obstacles and challenges.
Core values are critical for business success.
AI technology will revolutionize the landscape industry.
Simplicity in implementation leads to better outcomes.
Customer success management is essential for growth.
Mergers and acquisitions are becoming more common in the industry.
Aspire is well-positioned to leverage new technologies.

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