Ep 687. Successful but Broke? The Raw Truth Behind a 7-Figure Business

Caleb speaks with serial entrepreneur Dwayne Kerrigan, who shares insights from his 40-year career across 31 different businesses. The conversation focuses on the psychological shift from forced discipline to authentic commitment, emphasizing how personal purpose pulls an individual toward success more effectively than constant internal pressure. Kerrigan explains the importance of changing one's "primary question" to foster joy and appreciation rather than judgment or a rigid need to be right. He also provides strategic business advice on navigating economic cycles, suggesting that maintaining high cash reserves during "summer" periods allows for massive growth during "winter" recessions. Throughout the podcast, Kerrigan stresses that radical self-awareness and humility are the most critical tools for any leader seeking long-term fulfillment. Key Takeaways: Focus on finding a purpose that pulls you forward with momentum rather than relying solely on discipline to push yourself through tasks. Pay attention to physiological triggers like defensiveness to recognize when you are resisting a truth about yourself that someone else is reflecting. Improve your daily experience by intentionally shifting your primary internal question to one that focuses on appreciation and joy. Actively seek out mentors and strive to be the least knowledgeable person in a room to accelerate your personal and professional growth. Establish strong organizational structures and financial reserves during prosperous times to ensure your stability when the economic season inevitably shifts to a downturn. Connect with Auman Landscape 📺 YouTube https://www.youtube.com/@AumanLandscape 🌐 All Links https://linktr.ee/AumanLandscape 📸 Instagram https://www.instagram.com/aumanlandscapellc/ 👷 👷‍♂️ 👷‍♀️ The Hardsacpe Academy https://www.thehardscapeacademy.com/  👫 👩‍❤️‍👨 Together In The Trades https://www.togetherinthetrades.com/  Episode Sponsors 📸 CompanyCam – Get 50% off for 2 months https://companycam.com/auman 💰 Cycle CPA – Save $200 https://cyclecpa.com Use code: AUMAN 🛠 LMN Software – Save on onboarding https://golmn.com Use code: AUMAN 🚜⚙️🛠️ Steelwrist https://linktr.ee/AumanLandscape 🛠 Leanscaperhttps://leanscaper.com/ 🚜 Equip https://www.equipexposition.com/Use code: AUMAN 💰 John Pajakhttps://leanscaper.com/ 🧠 🎯 💡 FRWRD Coachinghttps://www.frwrdcoaching.com/      

Caleb interviews Brian Brown, owner of Estate Landscape and Tree in the Lake Tahoe region. Brown details his professional journey, explaining how he transitioned from an employee to the owner of a high-end firm through a strategic buyout. He emphasizes the importance of utilizing business management systems like LMN and the Leandcaper operating system to maintain profitability within a strictly regulated 24-week construction season. The discussion highlights the value of peer groups, mentorship, and leadership development for entrepreneurs seeking financial freedom and a better family lifestyle. Brown also recounts a dramatic story regarding an encounter with a Mexican cartel during a previous business venture. Key Takeaways: Implement business systems and software in gradual "baby steps" to avoid becoming overwhelmed while building a more efficient operation. Transition from employee to owner by proposing a strategic buyout plan that demonstrates clear value and creates a win-win scenario for the current founder. Define an Ideal Customer Profile to align your branding and services with the specific high-end or niche market you intend to dominate. Join a peer group or hire a business coach to gain objective perspectives from other leaders and ensure you aren't operating in isolation. Commit to constant evolution and the next "expedition" to prevent your business from stagnating once you reach an initial level of success. Connect with Auman Landscape 📺 YouTube https://www.youtube.com/@AumanLandscape 🌐 All Links https://linktr.ee/AumanLandscape 📸 Instagram https://www.instagram.com/aumanlandscapellc/ Episode Sponsors 📸 CompanyCam – Get 50% off for 2 months https://companycam.com/auman 💰 Cycle CPA – Save $200 https://cyclecpa.com Use code: AUMAN 🛠 LMN Software – Save on onboarding https://golmn.com Use code: AUMAN

Caleb and Brittany discuss the realities of running a seven-figure landscaping business while navigating major personal milestones and family responsibilities. The couple reflects on a recent trip to Las Vegas for a major construction trade show, using the experience as a backdrop to talk about the challenges of professional growth, entrepreneurship, and maintaining a strong family life. A significant part of the conversation focuses on their decision to homeschool their children while still maintaining high standards inside their growing business. They also share how their current success didn't happen overnight. Caleb and Brittany explain how years of financial discipline and commitment to the Dave Ramsey plan helped them recover from a past bankruptcy and build a more stable financial future. Throughout the episode, they emphasize the importance of community, shared goals between spouses, and having a clear purpose behind major life decisions. The conversation offers practical insight for entrepreneurs trying to balance business growth, family priorities, and financial responsibility. Key Topics in This Episode • Managing a seven-figure landscaping business • Balancing entrepreneurship and family life • Homeschooling while running a company • Building a strong support network with industry peers • Recovering from bankruptcy through financial discipline • Following the Dave Ramsey plan to eliminate debt • Using vision boards and goal-setting to guide the future • Identifying your "why" before making major life decisions Connect with Auman Landscape 📺 YouTube https://www.youtube.com/@AumanLandscape 🌐 All Links https://linktr.ee/AumanLandscape 📸 Instagram https://www.instagram.com/aumanlandscapellc/ Episode Sponsors 📸 CompanyCam – Get 50% off for 2 months https://companycam.com/auman 💰 Cycle CPA – Save $200 https://cyclecpa.com Use code: AUMAN 🛠 LMN Software – Save on onboarding https://golmn.com Use code: AUMAN

Caleb and Brittany are podcasting from Las Vegas during the ConExpo construction trade show. They discusses their business operations, including the launch of a new coaching group and Brittany's upcoming presentation on business growth. A significant portion of the conversation focuses on financial maturity, where they credit budgeting software and CFO services for transforming their company from a struggling venture into a profitable seven-figure business. They reflect on the necessity of professionalizing operations and moving away from "management by chaos" to achieve long-term stability. The episode serves as both a travel log of their time in Nevada and an educational resource for contractors seeking to improve their administrative systems.   Key Takeaways: Avoid the temptation to fill your schedule with "junk work" during slow periods and instead remain selective to ensure you are available for high-quality projects that fit your ideal business profile. Utilize professional budgeting and management software to clearly see your numbers and ensure that every job you take is generating a real profit. Shift from reactive to proactive financial management by working with a CFO who can help you plan for future growth rather than just looking at past performance. Develop the confidence to charge higher prices by respecting the value of your work and understanding the actual overhead costs required to run a sustainable business. Practice long-term financial foresight by incrementally budgeting for future major expenses, such as new equipment or facilities, well before you actually need to make the purchase. Episode Sponsors CompanyCam – Get 50% off for 2 months https://companycam.com/auman Cycle CPA – Save $200 https://cyclecpa.com (Use code: AUMAN) LMN Software – Save on onboarding https://golmn.com (Use code: AUMAN) Connect with Auman Landscape YouTube: @AumanLandscape Instagram: @aumanlandscapellc All Links: Linktree  

Caleb and Brittany record this episode live from CONEXPO 2026 in Las Vegas, discussing how their landscaping business evolved from small beginnings into a highly mechanized, technology-driven operation. Caleb explains how growing a company forced him to overcome his natural introversion and develop the confidence to price work correctly. The conversation dives into the importance of self-confidence, fast decision-making, and investing in modern equipment—like GPS grading and specialized attachments—to dramatically increase production. They also discuss the psychology of entrepreneurship, why hesitation can stall growth, and how successful contractors learn to execute once they have enough information. Throughout the episode, Caleb and Brittany credit mentors and industry experts who helped shape their business systems and thinking. Key Topics in This Episode Mechanization: Running a landscaping business in a highly mechanized era. The Founder's Journey: Overcoming introversion as a business owner. The Bottom Line: Building confidence in pricing and value. Cutting-Edge Tech: GPS grading and modern excavation technology. Execution: Making faster business decisions and avoiding "analysis paralysis." Community: Learning from mentors in the green industry. Systematization: Building systems instead of relying on brute-force labor. Episode Sponsors CompanyCam – Get 50% off for 2 months https://companycam.com/auman Cycle CPA – Save $200 https://cyclecpa.com (Use code: AUMAN) LMN Software – Save on onboarding https://golmn.com (Use code: AUMAN) Connect with Auman Landscape YouTube: @AumanLandscape Instagram: @aumanlandscapellc All Links: Linktree

In this episode, Caleb and Britney have an honest conversation about how running a business changes you — personally and professionally. They dive into the real transformation that happens when your livelihood depends on your ability to lead, communicate, and build relationships. One of the central questions they explore: What part of running the business changed you the most? From becoming more outgoing and learning how to strike up conversations, to pushing past natural personality traits for the sake of survival and growth — this episode is about the evolution every entrepreneur goes through. They discuss: How business forces personal growth Developing confidence in sales and networking Learning to be more social when it doesn't come naturally The survival mindset in early-stage business When they realized communication was critical to success The shift from technician to relationship-builder Growth through discomfort Is becoming more outgoing something you naturally develop — or something you force yourself to do because your business depends on it? Caleb and Britney reflect on when they realized they had to step outside their comfort zones and how that decision shaped their leadership and success. If you're building a business and feeling stretched beyond your personality, this episode will remind you that growth often comes from the pressure to survive — and thrive.

In this episode, Caleb breaks down how the health of your business directly reflects your leadership, discipline, and personal development. Key topics include: Personal development as the foundation for self-realization and self-awareness Clearly defining what a "win" looks like for yourself and your company The importance of carving out time for focused, deep work Dollar-bracketing systems to ensure efficiency and accountability Building a leadership pipeline — from apprentices to managers Giving true ownership and responsibility at every level Aligning training and SOPs so they reinforce each other Setting clear plans and executing them with precision A powerful episode on leadership, structure, and building a business that runs with clarity, accountability, and purpose. Auman Landscape on YouTube CompanyCam – 50% off for 2 months Linktree/AumanLandscape @aumanlandscapellc CycleCPA.com – Use code AUMAN to save $200 LMN Software – Save on onboarding with code AUMAN

In this episode, Caleb sits down with Nick Bartolo, founder of Essential Partners, to discuss what business owners need to consider when thinking about selling their company. Nick breaks down: The decision to sell and conducting a "possible path analysis" — evaluating revenue, EBITDA, and overall business valuation. Thinking beyond the sale price — retirement planning, ensuring your investments can support your lifestyle, and avoiding poor tax advice. He also covers: Optimizing growth, margins, and return on capital Building a business that is sustainable and not dependent on the owner Understanding the broader industry landscape The importance of strong books, clean financial records, and a reliable CPA Strategic tax planning, including starting a Roth IRA This episode is packed with practical insights for any contractor or entrepreneur planning long-term growth, exit strategy, and financial freedom. Nick Bartolo – [email protected] Instagram: @nickbartolo_ep Elite Networks Auman Landscape on YouTube Primed For Growth CompanyCam – 50% off for 2 months Linktree/AumanLandscape @aumanlandscapellc CycleCPA.com – Use code AUMAN to save $200 LMN Software – Save on onboarding with code AUMAN

In this episode, Caleb talks about choosing the right equipment and building the right team. He explains how company assets — from tools, machines, and vehicles to productivity apps like CompanyCam and LMN (Landscaper Management Network), down to something as simple as a good pair of gloves — all play a critical role in operational efficiency. At the same time, he emphasizes building a team that can run the business independently — from sales and designers to laborers — and implementing systems that create a more efficient, productive, and scalable operation. Elite Networks Auman Landscape on YouTube Primed For Growth CompanyCam – 50% off for 2 months Linktree/AumanLandscape @aumanlandscapellc CycleCPA.com – Use code AUMAN to save $200 LMN Software – Save on onboarding with code AUMAN

In this episode, Caleb talks about having the bravery to stay disciplined — even in a slow economy with revenue pressure — and choosing the right clients. He emphasizes focusing on your ideal ICP, working with people who understand and value your work, and only taking on projects that are truly worth doing — purposeful and intentional, rather than driven by short-term fear. https://www.elitenetworks.us Auman Landscape on YouTube Primed For Growth www.companycam/kcpodcast Company Cam- 50% for 2 months! Linktree/AumanLandscape @aumanlandscapellc www.CycleCPA.com  Use code: Auman and save $200 when signing up. LMN Software Save on onboarding! Code: AUMAN