The Deal Factory

What does it take to build one of the most influential companies in the landscape industry? According to Yellowstone Landscape CEO Tim Portland, it's about a lot more than acquisitions.In this episode of The Deal Factory, Jeff Harkness sits down with Tim to unpack Yellowstone's remarkable growth journey, the leadership philosophy behind its success, and why organic growth may be the greatest competitive advantage of all.From building high-performing teams and scaling sales to navigating private equity partnerships and making smarter acquisitions, Tim shares the lessons learned from more than a decade of building an industry powerhouse.In this episode:The strategy behind Yellowstone's growthWhy organic growth is harder than acquisitionsLessons from 35 acquisitions and 500+ evaluationsBuilding leaders and creating accountability at scaleWhy cash flow matters more than EBITDA alone

What happens when the business you fought to build nearly breaks you and then becomes the vehicle for your next chapter?In this episode of The Deal Factory, Jeff Harkness sits down with entrepreneur David Koehn to unpack a journey that started with $12,000 borrowed from his father, a lawnmower, and a Ford Explorer — and ultimately led to building and selling Koehn Outdoors. David shares the mistakes that nearly put the company under, the strategic shift that transformed the business, and why building a team capable of operating without him became one of the most valuable things he ever did.David and Jeff also go inside the sale to Bland Landscaping, including why trust mattered more than simply finding the highest bidder, what surprised David during post-close integration, and why owners should expect change after a transaction. Now entering what he calls the “3.0 version” of his life, David is using those lessons to mentor and coach other entrepreneurs navigating growth, leadership, and eventual exits.Key Discussion PointsWhy David left his hometown at 21 with no real plan beyond creating a different lifeBorrowing $12,000 from his father — and the condition that forced him to go all-in on entrepreneurshipGrowing from residential lawn care into commercial landscaping and HOA workWhy chasing revenue and large installation projects nearly drove the company into bankruptcyThe decision to abandon construction work and become intensely focused on recurring maintenanceHow consultants, better systems, budgeting, and peer relationships helped transform the businessWhy hiring business development talent earlier could have accelerated David’s growthHow stepping away from operations proved David had built a company that could function without himWhy David chose a trusted strategic partner instead of running a broad auction for the highest bidderThe realities of post-sale integration: systems, safety, compensation, communication, and cultural changeWhy owners should never believe that “nothing will change” after a transactionHow David transitioned from owner-operator to investor, advisor, and CEO coachWhy mentors can dramatically change the trajectory of an entrepreneur’s lifeDavid’s advice to aspiring entrepreneurs: action wins

The skills that build a company are not always the skills required to scale one.In this episode of The Deal Factory, Jeff Harkness sits down with his own CEO coach, Chuck Gulledge, for a candid conversation about what happens to a leader as the business grows around them.After beginning his career as a CPA with Arthur Andersen, working in the capital markets, and spending years studying companies and their leaders, Chuck made a major career pivot at age 50 to become a certified executive coach. Thirteen years later, he works with CEOs and leadership teams across the country, helping them navigate strategy, execution, people, succession, and what he calls the “inner game” of leadership.Jeff and Chuck break down the difference between a consultant and a true coach, why CEOs must move beyond the “Superman” phase of entrepreneurship, and how identifying constraints, finding your highest and best use, and building operating systems can transform a growing organization.They also explore Momentum Hub, Chuck’s approach to turning strategy into execution, why AI will enhance leadership without replacing the human side of coaching, and what happens as entrepreneurs evolve from doing everything themselves to multiplying leaders.For founders and CEOs scaling businesses in the trades and service industries, this conversation asks an important question:Are you still the leader your next stage of growth requires?Key Discussion PointsChuck’s journey from CPA and capital markets executive to CEO coachWhy he left his established career at age 50 to pursue coachingThe difference between a CEO coach and a consultantWhy coachability matters more than simply hiring a coachThe loneliness that comes with leading and scaling a companyFinding your highest and best use as a CEOWhy leadership and the “inner game” become more important as companies scaleTurning strategy into execution through Momentum HubWhy strategic plans need to become living operating systemsPeople, strategy, and execution as fundamental building blocksIdentifying and attacking the top constraints inside a businessWhy bad meetings quietly destroy organizational productivity“Where do we play?” versus the more important question: “Where do we not play?”How CEOs unintentionally create cultural problems by tolerating the wrong behaviorsWhy customer experience and winning can strengthen company cultureThe evolution from founder “Superman” to building and multiplying leadersFamily-business succession and why the next generation has to earn leadershipWhy AI can improve business systems but cannot replace human connectionWhy self-doubt does not disappear when a CEO becomes successfulWhy Chuck believes every CEO should have a coachChapters:0:00 Intro0:39 Intro: Meet Chuck Gulledge2:17 How Does Someone Become a CEO Coach?3:40 Arthur Andersen, Capital Markets & Learning Leadership4:40 Discovering Executive Coaching5:40 Making a Major Career Pivot at 507:25 Why Entrepreneurship Can Be Lonely8:40 CEO Coach vs. Consultant10:45 Why Leadership Is the Real Work12:25 Finding Your Highest and Best Use14:50 What Makes a CEO Coachable?17:05 The Inner Game & Building Better Leaders18:30 Momentum Hub: Turning Strategy Into Execution21:30 Will AI Replace CEO Coaches?25:30 The Fundamentals of Scaling Leadership27:40 Finding and Attacking Business Constraints28:45 How Bad Meetings Waste a Company’s Time30:30 Strategy: Where Should You NOT Play?31:55 What Are You Tolerating Inside Your Business?32:35 Culture, Customers & Building a Winning Team35:15 How CEOs Change as Companies Scale36:25 From Superman to Multiplying Leaders38:45 Family Business Succession & Leadership Transitions43:10 When Should a CEO Hire a Coach?44:00 Why Every Leader Needs Coaching45:50 Every CEO Has a Journey47:10 The Inner Game at the Highest Level48:20 The Priority Paradox & CEO Accountability49:00 How to Connect With Chuck49:45 Closing Thoughts

Crystal Knafel started her landscaping business with a shovel, a wheelbarrow, and a willingness to outwork just about anyone. Today, she and business partner Krista Bontrager are building something much bigger.In this episode of The Deal Factory, Jeff Harkness sits down with Crystal and Krista to discuss their evolution from a founder-led operation into a $5M+ multi-location business pursuing growth through acquisitions. They share how their visionary-integrator partnership works, what they learned acquiring Lawn & Turf, and why culture became one of their biggest post-close challenges.The conversation covers M&A, integration, leadership, organic growth, technology, talent, and their long-term vision of building a $100M+ landscaping platform.Landscaping Services Indiana | Design & Lawn Care Experts | Dynamic LandscapingKey Discussion PointsCrystal's journey from a shovel and wheelbarrow to business ownerHow Krista became the integrator to Crystal's visionaryUsing EOS and mentorship to create structure for growthWhy they chose Lawn & Turf as an acquisition targetDiscovering culture problems after the deal closedRebuilding the team and integrating the acquisitionMoving from pure grit to intentional growth strategyWhy alignment is critical in a business partnershipDelegating responsibilities as the company scalesBuilding a stronger organic sales engineUsing Aspire, Weathermatic and AI in the businessRecruiting and retaining the right peopleWhy Crystal wants to build the platform—not sell to oneThe five-year vision for a $100M+ landscaping companyChapters: 0:00 Intro 0:26 Meet Crystal and Krista 2:03 How Crystal Started the Business 5:29 Krista Joins the Business 8:43 Visionary vs. Integrator 10:50 Where the Business Is Today 13:01 Acquiring Lawn & Turf 15:48 The Reality of Post-Close Integration 18:22 Rebuilding Culture & Leadership 21:00 Women in the Green Industry 24:00 Learning to Delegate 28:15 How Their Partnership Works 31:20 Handling Disagreements & Staying Aligned 36:50 The Next Critical Hire 38:12 Technology & Operational Infrastructure 41:20 Robotics & AI 43:00 Solving the Labor Challenge 46:34 Building the Platform 48:35 Mentors, Belief & Thinking Bigger 52:18 The $100M Vision 55:35 Closing Thoughts

Private equity has never been more misunderstood.In this episode of The Deal Factory, Jeff Harkness sits down with longtime friend and Plexus Capital Partner Brad Pence for one of the most practical conversations yet on how institutional investors actually evaluate businesses. From defining the lower middle market to explaining fund structures, leadership, AI, operations, and value creation, Brad provides an inside look at what separates companies that attract premium valuations from those that struggle to transact.The conversation goes well beyond deal multiples. Brad shares how great investors think about people, leadership, operational excellence, technology adoption, capital deployment, liquidity, continuation vehicles, and why the best private equity firms are focused on building stronger businesses—not simply buying EBITDA.Whether you're a founder considering institutional capital, an executive leading a PE-backed company, or simply trying to understand how today's investment market works, this episode offers a masterclass on what creates long-term enterprise value.Key Discussion PointsBrad Pence's journey from college graduate to Partner at Plexus CapitalDefining the lower middle market vs. the middle marketWhat institutional investors actually evaluate before investingWhy leadership is the single biggest investment decisionBuilding trust between founders and private equity partnersCurrent state of lower middle market deal activityReturn expectations, fund structures and investor disciplineContinuation vehicles explained simplyHow AI is improving business development and operational efficiencyWhy data systems and financial visibility drive enterprise valueThe operational playbook behind successful platform companiesOrganic growth vs. acquisition integrationDebunking common myths about private equityAlternative capital options through structured debt and minority investmentsBalancing career, family and high performanceChapters:0:00 Intro1:10 Meet Brad Pence & Plexus Capital7:30 From Analyst to Private Equity Partner17:30 What Is the Lower Middle Market?20:15 Current State of Private Equity24:30 Capital Deployment & Investor Expectations30:00 Fund Life Cycles & Liquidity33:00 Continuation Vehicles Explained35:45 AI's Real Impact on Private Equity41:20 Leadership Is Everything48:40 The Plexus Operating Playbook52:10 Building Companies That Scale56:45 Private Equity Myths Debunked1:00:30 Structured Capital Without Giving Up Control1:04:30 Brad's Leadership Habits & Closing Thoughts