Sales made Simple for Outdoor Living Pros, Landscapers and Hardscapers (formerly Outerspaces)

Hosted by Joshua Gillow

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346

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Nov 2026

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About the show

This podcast is dedicated to helping overwhelmed outdoor living professionals, landscapers and Hardscapers just like you increase your closing rate to over 75% without doubling your workload so you can build a seven-figure business that doesn't need you.

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60 recent

November 11, 2026Episode 17931 min

Stop Panicking When Customers Push Back on Payment and Start Protecting Your Business w/ attorney, Brett Riegel

Schedule a Meeting with Joshua TODAY! What do you do when a customer suddenly refuses to pay, demands extra work, or claims the finished project isn't what they expected? Do you give in to keep the peace, or do you know how to protect your business? Customer disputes are part of running a contracting business, but how you respond can make the difference between resolving an issue and turning it into an expensive mess. Without clear contracts, documented expectations, and a plan for handling disagreements, contractors can end up giving away money, doing unpaid work, or putting themselves in a difficult legal position. In this episode, Joshua Gillow sits down with attorney Brett Riegel to walk through real-world situations contractors face, from customers withholding final payments to changing their minds about approved designs. Brett shares why staying calm, understanding your contract, and getting legal guidance early can help you make better decisions and avoid unnecessary conflict. In this episode, you'll learn how to: Handle customer disputes without making the situation worse: Discover why your first move should be to stay calm, clarify exactly what the customer wants, and review what your contract actually requires. You'll also learn how to recognize when a reasonable compromise makes sense and when a customer is asking for something beyond the original agreement. Protect your cash flow when customers delay payment: Learn how to communicate when a customer misses a scheduled payment, document the issue, and understand when you may need to formally address a breach of contract. Brett also explains why contractors need clear payment schedules and shouldn't continue carrying the financial burden of a project when customers aren't holding up their end of the agreement. Avoid expensive legal problems before they start: Understand why detailed proposals, approved designs, written change orders, and updated contracts can prevent misunderstandings. You'll also hear when to contact an attorney, what some initial legal consultations may cost, and how tools like mediation clauses can help resolve disputes before they turn into lawsuits. Press play to learn how to protect your contracting business, handle difficult customers with confidence, and put the right legal safeguards in place before a project goes sideways. Ready to get your copy of The CORE 10 ? Check it out HERE ! Connect with Joshua at: The Website The Facebook Group Sales Master Classes How to work with Joshua - https://yes.express/apply/ Tune into this podcast where a seasoned craftsman shares expert communication skills, strategies for overcoming stress and overwhelm, and insights on building a profitable business in landscaping and hardscaping, with tips on how to sell, close more deals, and achieve financial freedom to retire early as a successful business owner in the design/build and outdoor living industry. Music from #Uppbeat: https://uppbeat.io/t/abbynoise/puncher License code: AWUDIYK15E3NWYPK

November 4, 2026Episode 17823 min

Stop Comparing Your Business to Other Contractors Because You're Only Seeing Half the Story w/ Alex Bulow from Inca Stone

Schedule a Meeting with Joshua TODAY! Do you ever look at another contractor's trucks, equipment, projects, or business growth and wonder why you aren't further along? What if you're comparing your behind-the-scenes reality to someone else's highlight reel? It's easy to look at what other contractors have and feel like you're falling behind. But you rarely know the full story behind their success, including their financial situation, struggles, sacrifices, or the opportunities they've been given. In this episode, Joshua Gillow sits down with Alex Bulow of Inca Stone to discuss why comparing yourself to others can steal your joy, distract you from your own progress, and keep you from appreciating how far you've come. They also explore how focusing on small, consistent improvements can help you grow your business while creating a more meaningful life outside of work. In this episode, you'll learn how to: Stop measuring your success against other contractors: Understand why every business has a different story, starting point, financial situation, and set of challenges. Learn why comparing yourself to someone else's results can create unnecessary frustration and take your focus away from your own progress. Use small improvements to create lasting growth: Discover the power of getting just a little bit better every day. Joshua shares his 2-millimeter philosophy and explains how small, consistent steps can add up to major improvements in your business, skills, and personal life over time. Develop a growth mindset and redefine success: Learn how adding one simple word, "yet," can change the way you approach challenges. You'll also hear why growth isn't always about more revenue, bigger jobs, or additional equipment. Sometimes real success means having more time for your family, serving others, and building a life you actually enjoy. Press play to discover how shifting your focus from comparing yourself to others to becoming better than you were yesterday can help you grow your business, find more fulfillment, and build a life that matters. Ready to get your copy of The CORE 10 ? Check it out HERE ! Connect with Joshua at: The Website The Facebook Group Sales Master Classes How to work with Joshua - https://yes.express/apply/ Tune into this podcast where a seasoned craftsman shares expert communication skills, strategies for overcoming stress and overwhelm, and insights on building a profitable business in landscaping and hardscaping, with tips on how to sell, close more deals, and achieve financial freedom to retire early as a successful business owner in the design/build and outdoor living industry. Music from #Uppbeat: https://uppbeat.io/t/abbynoise/puncher License code: AWUDIYK15E3NWYPK

October 28, 2026Episode 17721 min

Scared to Show Your Employees the Numbers? You Might Be Holding Back Your Best Team Members w/ Alex Bulow from Inca Stone

Schedule a Meeting with Joshua TODAY! What if being more transparent about your company’s finances could help your team make better decisions, take more ownership, and improve profitability? Many contractors keep financial information to themselves because they worry about how employees might react or what they might do with the numbers. But what happens when your team understands the financial health of the business and how their work impacts the bottom line? In this episode, Joshua Gillo talks with Alex Bulow of Inca Stone about how open-book management has helped his team understand job costs, navigate financial challenges, and work together toward shared goals. In this episode, you’ll discover how to: Build a team that thinks like owners: Learn how sharing the right financial information can encourage employees to take more responsibility, contribute ideas, and care about the company’s success. Use your numbers to make better decisions: Understand how job costing, profit margins, and accurate financial records can help you evaluate performance and identify opportunities to improve. Introduce financial transparency without creating confusion: Discover why educating your team is just as important as sharing the numbers, and how you can start small before opening up more of your books. Press play to hear how Alex uses open-book management to build trust, improve accountability, and help his team make decisions that support a healthier, more profitable contracting business. Ready to get your copy of The CORE 10 ? Check it out HERE ! Connect with Joshua at: The Website The Facebook Group Sales Master Classes How to work with Joshua - https://yes.express/apply/ Tune into this podcast where a seasoned craftsman shares expert communication skills, strategies for overcoming stress and overwhelm, and insights on building a profitable business in landscaping and hardscaping, with tips on how to sell, close more deals, and achieve financial freedom to retire early as a successful business owner in the design/build and outdoor living industry. Music from #Uppbeat: https://uppbeat.io/t/abbynoise/puncher License code: AWUDIYK15E3NWYPK

October 21, 2026Episode 17648 min

I’d Rather Fail 1,000 Times Than Live With the Regret of Never Trying

Schedule a Meeting with Joshua TODAY! What does it take to keep moving forward when your business is struggling, your plans fall apart, and everything seems to be working against you? In this episode, Joshua Gillow sits down with Justin Louder, owner of Louder Family Hardscapes in Asheville, North Carolina, to discuss his incredible journey from addiction and homelessness to running his own hardscaping business. After experiencing business failures, financial setbacks, and the devastating loss of thousands of dollars in equipment, Justin learned that failure doesn't have to be the end of your story. Through faith, perseverance, and a commitment to personal growth, Justin discovered how to turn setbacks into lessons, stay focused on what truly matters, and keep pursuing his vision even when the odds seem stacked against him. In this episode, you'll discover how to: Turn failure into fuel for growth. Learn how to reframe mistakes and setbacks as opportunities to improve your skills, strengthen your character, and become a better business owner instead of letting them convince you to quit. Build a stronger business without sacrificing what matters most. Discover why focusing exclusively on money, equipment, and growth targets can leave you feeling unfulfilled, and how reconnecting with your purpose, your faith, and your family can help you regain perspective. Develop the perseverance to pursue your vision. Understand how daily habits, a willingness to embrace discomfort, a strong support network, and the courage to take calculated risks can help you move forward when business and life get tough. Justin's story is a powerful reminder that you don't have to have everything figured out to get started. You just need the willingness to learn, the courage to keep taking the next step, and the determination to refuse to let setbacks define your future. Press play now to discover how to turn your toughest setbacks into stepping stones and build the contracting business and life you've always envisioned. Ready to get your copy of The CORE 10 ? Check it out HERE ! Connect with Joshua at: The Website The Facebook Group Sales Master Classes How to work with Joshua - https://yes.express/apply/ Tune into this podcast where a seasoned craftsman shares expert communication skills, strategies for overcoming stress and overwhelm, and insights on building a profitable business in landscaping and hardscaping, with tips on how to sell, close more deals, and achieve financial freedom to retire early as a successful business owner in the design/build and outdoor living industry. Music from #Uppbeat: https://uppbeat.io/t/abbynoise/puncher License code: AWUDIYK15E3NWYPK

October 14, 2026Episode 17530 min

Why Working Until You Can't Anymore Is a Terrible Retirement Strategy for Contractors w/ Financial Wealth Advisor, Jonathan Carpenter

Schedule a Meeting with Joshua TODAY! What if you spend decades building a successful contracting business only to realize you never made a plan for what comes next? As a landscaper, hardscaper, or outdoor living pro, it's easy to get caught in survival mode. You're focused on keeping projects moving, paying bills, supporting your family, and making sure the business survives another season. But without a financial roadmap, you may end up working longer than you want, missing precious time with your family, or reaching retirement without the resources to support the life you imagined. In this episode, Joshua Gillow sits down with financial planner Jonathan Carpenter to explore how contractors can turn retirement from a vague hope into a practical plan. They discuss defining what you want your future to look like, understanding what it will cost, preparing for unexpected obstacles, and making informed financial decisions along the way. You don't need to have every answer today or assume you'll need millions sitting in the bank. You need a starting point, a clear direction, and a plan you can adjust as life changes. In this episode, you will: Discover how a financial roadmap can help you move beyond survival mode and create more confidence about your future. Learn how to connect your retirement goals, family priorities, and financial decisions so you can make intentional choices today. Understand why planning for unexpected events and reviewing your strategy over time can help protect your family and preserve your future options. Press play to learn how to build a financial roadmap that helps you spend less time worrying about your future and gives you more freedom to choose how you live, work, and spend time with the people who matter most. Ready to get your copy of The CORE 10 ? Check it out HERE ! Connect with Joshua at: The Website The Facebook Group Sales Master Classes How to work with Joshua - https://yes.express/apply/ Tune into this podcast where a seasoned craftsman shares expert communication skills, strategies for overcoming stress and overwhelm, and insights on building a profitable business in landscaping and hardscaping, with tips on how to sell, close more deals, and achieve financial freedom to retire early as a successful business owner in the design/build and outdoor living industry. Music from #Uppbeat: https://uppbeat.io/t/abbynoise/puncher License code: AWUDIYK15E3NWYPK

October 7, 2026Episode 17428 min

Stop Waiting for the Next Big Job to Start Building Your Financial Future w/ Wealth Advisor Jonathan Carpenter

Schedule a Meeting with Joshua TODAY! Are you building a successful contracting business but still have no clear idea how that business will give you the freedom to stop working someday? Contractors are used to trading their time, skills, and physical effort for money. But building a business is supposed to create more than another job. It should ultimately give you the freedom to choose how you spend your time, where you spend it, and how much work you actually need to take on. The problem is that many contractors keep waiting for the next big project, the next profitable year, or the point when they finally have "enough" money to start investing. In this episode, Joshua Gillow talks with wealth planner Jonathan Carpenter about why waiting can be one of the most expensive decisions you make, how compound growth rewards those who start early, and how a simple automated investment strategy can turn today's business income into tomorrow's financial freedom. You will: Understand why starting with a small amount today can be more powerful than waiting until you have significantly more money to invest. Learn how contractors can find additional cash flow by understanding their business expenses, cutting what doesn't create value, and intentionally allocating money toward their future. Discover how creating a financial plan can give you the clarity and confidence to know where you're going instead of simply hoping that years of hard work will eventually be enough. Press play to learn how to turn the money you earn through your contracting business into a long-term plan for financial freedom, so you can eventually work because you want to rather than because you have to. Ready to get your copy of The CORE 10 ? Check it out HERE ! Connect with Joshua at: The Website The Facebook Group Sales Master Classes How to work with Joshua - https://yes.express/apply/ Tune into this podcast where a seasoned craftsman shares expert communication skills, strategies for overcoming stress and overwhelm, and insights on building a profitable business in landscaping and hardscaping, with tips on how to sell, close more deals, and achieve financial freedom to retire early as a successful business owner in the design/build and outdoor living industry. Music from #Uppbeat: https://uppbeat.io/t/abbynoise/puncher License code: AWUDIYK15E3NWYPK

September 30, 2026Episode 17339 min

Why Some Contractors Are Thriving in This Market While Others Are Fighting to Survive w/ Financial Expert, Greg Crabtree

Schedule a Meeting with Joshua TODAY! Are you prepared to stay profitable when the market slows down and homeowners have more contractors to choose from? When demand becomes uneven, landscapers, hardscapers, and outdoor living pros can't rely on simply being available to win work. Customers have more time to compare contractors, pricing becomes more competitive, and the businesses that fail to deliver consistently can quickly lose ground. In this episode, Joshua Gillow sits down with Greg Crabtree to break down what the numbers are showing in the contractor market and what successful businesses are doing differently. They discuss why operational excellence matters more in a slower market, how scheduling and rework impact profitability, why contractors need to defend their pricing, and how being discernibly different can help you win projects without competing solely on price. You will: Learn why showing up on time, eliminating rework, and delivering quality work can have a major impact on profitability. Understand how to protect your margins when facing inflation, tariffs, fuel costs, and other unexpected expenses. Discover how listening to customers, understanding their vision, and demonstrating your value can help you stand out from competing landscapers and outdoor living pros. Press play to learn how to build a more profitable contracting business that can withstand market uncertainty, protect your pricing, and win customers through better execution and greater value. Ready to get your copy of The CORE 10 ? Check it out HERE ! Connect with Joshua at: The Website The Facebook Group Sales Master Classes How to work with Joshua - https://yes.express/apply/ Tune into this podcast where a seasoned craftsman shares expert communication skills, strategies for overcoming stress and overwhelm, and insights on building a profitable business in landscaping and hardscaping, with tips on how to sell, close more deals, and achieve financial freedom to retire early as a successful business owner in the design/build and outdoor living industry. Music from #Uppbeat: https://uppbeat.io/t/abbynoise/puncher License code: AWUDIYK15E3NWYPK

September 23, 2026Episode 1721 hr 4 min

Your Past Doesn't Get to Decide Who You Become w/ Frank Ingrassia

Schedule a Meeting with Joshua TODAY! For many landscapers, hardscapers, and outdoor living pros, business challenges can feel overwhelming. But what happens when you've already faced something far harder than a difficult season in business? In this episode, Joshua Gillow sits down with Frankie Ingrassia to unpack his journey through addiction, recovery, entrepreneurship, family, accountability, and rebuilding his life from the ground up. His story offers powerful lessons about taking responsibility, creating structure, developing grit, and using your experiences to help others. After listening, you'll discover How taking personal responsibility can become the first step toward changing your life and your business. Why structure, accountability, and surrounding yourself with the right people can help you stay on track when motivation isn't enough. How difficult experiences can build resilience, create perspective, and ultimately help you become a stronger entrepreneur, leader, and person. Press play to hear how Frankie turned some of the darkest moments of his life into a foundation for recovery, entrepreneurship, family, and meaningful impact. Ready to get your copy of The CORE 10 ? Check it out HERE ! Connect with Joshua at: The Website The Facebook Group Sales Master Classes How to work with Joshua - https://yes.express/apply/ Tune into this podcast where a seasoned craftsman shares expert communication skills, strategies for overcoming stress and overwhelm, and insights on building a profitable business in landscaping and hardscaping, with tips on how to sell, close more deals, and achieve financial freedom to retire early as a successful business owner in the design/build and outdoor living industry. Music from #Uppbeat: https://uppbeat.io/t/abbynoise/puncher License code: AWUDIYK15E3NWYPK

September 16, 2026Episode 17120 min

Building Real Trust With Your Crew Starts With YOU featuring Ryan Englin from Core Matters

Schedule a Meeting with Joshua TODAY! What if the reason your best guys are quietly checking out has nothing to do with pay, and everything to do with the fact that they don't know you care? In this episode, Joshua Gillow continues his conversation with Ryan Englin of Core Matters, picking up where they left off on using AI to build stronger teams. This time, they tackle something much harder to systemize: how leaders in the trades can actually show their teams they care, without it feeling forced, weak, or out of character. Ryan and Joshua get personal about the culture that teaches men to shove down emotion, the sobering mental health realities in construction, and the simple, low-pressure habits that build real trust on a crew. By the end of this episode, you'll learn: Why "no news is good news" is one of the most damaging beliefs a leader can carry, and what it silently tells your team. A simple onboarding tool called the "fuzzy file" that helps you learn what actually matters to your people, so a birthday card or a favorite snack can speak louder than any speech. Why asking "how did you sleep last night" in a morning huddle might be one of the most powerful leadership questions you can ask, and how sending someone home for a couple of days can save you from a much bigger cost down the road. Listen to the full episode to find out why demonstrating that you care might be the single biggest lever you have for building a team that will go to war with you. Ready to get your copy of The CORE 10 ? Check it out HERE ! Connect with Joshua at: The Website The Facebook Group Sales Master Classes How to work with Joshua - https://yes.express/apply/ Tune into this podcast where a seasoned craftsman shares expert communication skills, strategies for overcoming stress and overwhelm, and insights on building a profitable business in landscaping and hardscaping, with tips on how to sell, close more deals, and achieve financial freedom to retire early as a successful business owner in the design/build and outdoor living industry. Music from #Uppbeat: https://uppbeat.io/t/abbynoise/puncher License code: AWUDIYK15E3NWYPK

September 9, 2026Episode 17027 min

AI Won't Replace Your Hardscapers, but It Might Save Your Team w/ Ryan Englin from Core Matters

Schedule a Meeting with Joshua TODAY! What if the biggest reason you're losing good employees has nothing to do with pay, and everything to do with how you communicate? In this episode, Joshua Gillow sits down with Ryan Englin of Core Matters to talk about how AI is reshaping leadership, hiring, and communication in the trades. Ryan shares why the real problem behind most staffing struggles isn't a lack of leads or a labor shortage, but a retention problem rooted in poor communication. They dig into how AI can help owners and frontline managers slow down emotionally charged moments, have tougher conversations with more compassion, and finally solve the dreaded performance review. By the end of this episode, you'll learn: Why AI can't read your tone or body language, and how that "blind spot" can actually make it a powerful tool for responding instead of reacting when you're frustrated with a teammate. A simple, non-confrontational way to open up a tough conversation with an underperforming employee, without triggering defensiveness or a fight-or-flight response. How AI is starting to move beyond the office and into the field, giving technicians and crews real-time answers, SOPs, and the right words to say on the job site. Listen to the full episode to discover why your team already knows whether you care, and why AI might be the tool that finally helps you show it. Ready to get your copy of The CORE 10 ? Check it out HERE ! Connect with Joshua at: The Website The Facebook Group Sales Master Classes How to work with Joshua - https://yes.express/apply/ Tune into this podcast where a seasoned craftsman shares expert communication skills, strategies for overcoming stress and overwhelm, and insights on building a profitable business in landscaping and hardscaping, with tips on how to sell, close more deals, and achieve financial freedom to retire early as a successful business owner in the design/build and outdoor living industry. Music from #Uppbeat: https://uppbeat.io/t/abbynoise/puncher License code: AWUDIYK15E3NWYPK