Lessons In Failure And Surviving - 1.5 Years After My Landscaping and Tree Trimming Acquisition Update

July 29, 2025
by a searcher in Tampa, FL, USA
(Referencing my previous post about closing the $6.5M tree trimming and landscaping deal - https://searchfunder.com/post/finally-closed-first-deal-after-almost-3-years)
About a year ago, I shared the story of finally closing our first deal after immense persistence and 3 years of trials. That post resonated with many of you, and I appreciate the support. Today, I'm sharing the next chapter – one forged in fire, but leading to an unprecedented increase in clarity and capability and my desire to help other businesses and individuals.
What Happened Next: The Unwinnable War
Nine months after closing my first acquisition, our business faced a catastrophic, unforeseen challenge. Miami-Dade County, our largest client, began breaching 8 of their contracts worth millions of dollars with us because they had taken money out of our pool of funds and used it for special projects, causing our funds to run out 6 months early in our contracts. This deliberate misallocation of tens of millions of dollars by the county eliminated 80% of our revenue overnight. This was a client the company had for 30 years, with no other problems like this before. This is something we couldn’t have foreseen.
Yes, we could have fought them legally on this… But since they are a government entity they essentially have unlimited funds - while we did not.
I knew when I bought the company that the 85% reliance at that point on one client was a major issue… We were working to get out of that over time. But we didn’t end up having enough time to fix.
We - my management team and employees and I - fought tirelessly and were able to keep the company alive for 7 months while most companies would have failed within weeks. This was a feat of operational ingenuity and sheer will. But the blow from the county was fatal. And it ultimately led us to perform an Assignment for the Benefit of Creditors (ABC), and now the company is going through liquidation.
Vulnerabilities Exposed: A Few Lessons Forged in the Crucible
While the county's actions were the ultimate cause, this crisis served as a powerful learning and skill building exercise, exposing critical internal vulnerabilities within the inherited system. I did extensive due diligence before and during the closing process, but I did not see the following issues during due diligence. I only began seeing them when the crisis with the county got bad and the cracks in the foundation of the business grew.
Cultural Decay - The Other Main Issue I Found Out About After The Crisis Began
Unchecked Cultural Dependency: The existing 'Culture of Dependent Technicians' was inadvertently allowed to persist and even grow, where tactical firefighting by leadership enabled dependency and undermined strategic roles.
Tolerance of Organizational Poisons: Passive aggression, secretive behavior, siloing information, blame-shifting, and ambiguity were tolerated for too long and even allowed and encouraged by the prior owner… Which I didn’t know before I bought the company. This meant I inherited a culture built for failure when a crisis happened.
Gaps in Strategic Oversight: Critical changes were not enforced enough after the initial integration phase, and scope/accountability in key client contracts were not meticulously defined. This exposed vulnerabilities in strategic control and resource management, emphasizing the need for precise operational playbooks.
IMPORTANT LESSON - This underscored the critical need for the deep cultural due diligence now codified in my Protocol.
Other Major Problems And Mistakes I Made
I made critical errors in judging character and extending trust too readily, a lesson now codified in my 'Peril of Hope' doctrine.
Not doing more to get rid of/change the prior culture faster.
Tolerating too much.
Doing too much tactical firefighting - this became a daily thing for all of us after the crisis with the county began and helped us survive, but at huge cost physically and mentally.
And other critical lessons now addressed by my Protocol.
In short, while as the leader I made many mistakes… Nothing my team or I could have done would have saved us from what the county did and I’m proud of everything we did to save the business. Plus, it did lead to something great. Enormous and rapid gains of knowledge, experience, insight, and capabilities for the future.
The Transformation: The Phoenix Protocol & The Anti-Fragile Man
This collapse and the profound personal suffering that came from this became my workshop. It forced me to systematically analyze every lesson and forge The Phoenix Protocol – my proprietary, comprehensive operating system for transforming chaos into strategic advantage and building anti-fragile success.
In just 22 days, I completed all 4 phases of this Protocol, creating a 1,200-1,600 page library of wisdom and over 160 unique references. This unprecedented journey transformed me and made me fundamentally better, stronger, and more skilled.
Who I Am Now & What I Bring (Your Strategic Investment):
I can now prevent catastrophic failures, optimize operational performance, and build truly anti-fragile teams and cultures that don't just survive disruption—they grow stronger from it. This capability was forged through the M&A process, the after-integration, the cultural and operational improvements we made while I owned the company, and the knowledge, skills, and experience I gained running a $4.5 million company and then helping it navigate the turnaround and ABC process.
Master Systems Architect: I create order from immense chaos, designing robust, scalable systems and competitive moats (like the Rockefeller Method).
Anti-Fragile Operator: I consistently operate from a baseline of unshakeable peace and clarity (my 'Elixir of Life'), ensuring every decision is strategic and effective. My focus - even when dealing with extreme chaos and crisis - can help eliminate inefficiencies and unlock new opportunities.
Leader of Leaders: I lead with 'Armored Humanity,' demanding excellence and accountability, and empowering A-players (the Bezos Method) to drive outcomes.
Battle-Tested Acquirer: I bring direct experience leading $10 million in acquisitions and divestitures, including a $6.5M business and land acquisition and a $3.5M sale-leaseback. My 'Anti-Fragile Investor's Playbook' ensures meticulous vetting and deal structuring.
Transformed a $3.7M liability into a potential $7.7M counter-offensive claim, resulting in an $11.4M positive swing through forensic data analysis and architecting the ABC strategy.
Expert in Human Systems: The 'Ph.D.-level understanding of operational resilience and team psychology under pressure that I now have allows me to diagnose and correct organizational poisons.
What I'm Looking For: Architecting the Next Ascent
I'm now actively seeking CEO, COO, or high-level strategic/consulting roles within $5 million to $50 million companies in the Greater Tampa Area or Remote, particularly those backed by private equity firms or search funds. I am looking for an opportunity to apply this system to build something truly extraordinary and enduring. I would also love to advise and help other Searchers as well on how to better structure deals, value opportunities, spot weak points and red flags, and help guide you on your journey to acquiring your business.
If you're a leader focused on building for robust, sustainable growth, or navigating complex transformations, I'd welcome a brief, focused conversation.
Thank you and I hope this helps others avoid the pain I have gone through.