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

Hosted by Joshua Gillow

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343

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Oct 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

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

September 2, 2026Episode 16942 min

Outdoor Living Pros Don't Talk About This Part of Success Enough w/ Tanner Broughton owner of Firescapes and Founder of Hardscape Paradise

Schedule a Meeting with Joshua TODAY! What if the very thing that made you a great business owner is standing in the way of you becoming a great leader? In this episode, Joshua Gillow reconnects with Tanner Broughton of Firescapes and founder of Hardscape Paradise, for a deeper, more personal conversation than their first sit-down. They dig into the real balancing act of running a business while showing up for a marriage and young kids, the threshold moments that forced Tanner to grow, and the humbling shift every founder eventually faces: learning to let your team outshine you. Tanner also opens up about the highs and stress of launching an international event from scratch, and shares what's new for Hardscape Paradise 2027 in Cancun. You'll learn: How becoming a father reshaped Tanner's patience, empathy, and leadership, and why kids can teach business owners lessons no employee ever could. The four-tier mindset shift needed to grow from "the guy who does it all" to a leader who fans the flames of his team's talent, even when they start outperforming him. What it really took behind the scenes to launch Hardscape Paradise, from a stress-induced sick night before the first event to the early bird sign-ups already rolling in for 2027. Listen to the full episode to hear how releasing control might be the very thing that takes your business, and your life, to the next level. Are you ready to plan your own escape? Learn more and sign up at hardscapeparadise.com . 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

August 26, 2026Episode 1681 hr 9 min

Beyond the Numbers....Who Is Weston Zimmerman?

Schedule a Meeting with Joshua TODAY! You've seen Weston Zimmerman everywhere. Every hardscaping event, every social feed, every "know your numbers" conversation in the landscaping and outdoor living space. But who is the man behind Synked Up? This week, we pull the mask off. In this raw, unscripted conversation, Weston opens up about what most founders never say out loud. The addiction to solving problems, the year they almost couldn't make payroll, a customer who paid for dinner because Weston didn't have the cash, and the moment his own family's future was on the line. He talks candidly about: Why he cut his travel from 100+ nights a year on the road down to 38, and what it cost the business to do it The early days of Synked Up, when a trade show sign up saved the company from running out of cash Working through hard seasons with his dad, and how that relationship became one of the strongest in his life Why mentorship isn't optional. "There's no way Synked Up exists today without mentors." The pressure to perform a founder "persona," and how he's learning to just be radically honest instead What legacy actually means to him, for his kids, his team, and the industry he serves This isn't a numbers episode. It's a look at the real tension every entrepreneur faces, chasing a mission while protecting your family, your faith, and your own identity along the way. If you've ever wondered how someone builds a company while staying present at the dinner table, this conversation will hit home. Listen now to hear Weston get real about the cost of building Synked Up and don't miss his Contractor Summit, September 10 and 11 in Pittsburgh, where he'll unveil what's next for the industry. Grab your ticket before it sells out! https://synkedup.com/ 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

August 19, 2026Episode 16750 min

The Hidden Cost of Hyper-Focusing on Your Landscaping Business

Schedule a Meeting with Joshua TODAY! What if the patterns helping you build your business are actually holding you back in your life? For many outdoor living pros, hardscapers, and landscapers, the drive to grow a successful business can come with a hidden cost. Hyper-focusing on the business can slowly impact your family, health, relationships, and even your sense of fulfillment. In this episode, Joshua Gillow sits down with mindset coach and NLP practitioner Kyle Gillette to explore how self-awareness, limiting beliefs, and deeply ingrained patterns shape the way you lead, work, and live. Kyle shares his four-step process for creating lasting change and explains how releasing the baggage you carry can give you the clarity to create, act, and stay focused on the future you actually want. By the end of this episode, you'll learn: How to identify the mental and emotional baggage keeping you stuck and begin recognizing the patterns that may be limiting your business and personal growth. The four steps to lasting change: Release, Create, Act, and Focus, and how to apply them when you're ready to break an old pattern. How greater self-awareness can change the way you lead, helping you show up differently for your business, your team, your family, and yourself. Listen to the full episode and start identifying the patterns that are keeping you from your next level! 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

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