The Better Contractor Podcast

In Episode 91 of The Better Contractor, Alex sits down with Brent Oberlink and Aney Bailor to answer a question many long-time listeners and younger followers have: Who is the couple behind Lanracorp?

Building a successful company while maintaining a strong marriage is no easy task. Brent and Aney share their journey from the early days of long-distance dating, law school, MBA school, and midnight drives to building Lanracorp into a thriving enterprise. They break down what it really takes to work alongside your spouse, manage disagreements, navigate sacrifices, and align your core values across both personal life and business operations.

In this episode, we cover:

• How Lanracorp started and evolved over the years
• Navigating long-distance relationships while launching a business
• Quality time vs. intentionality in marriage and entrepreneurship
• How Brent and Aney divide roles based on their unique strengths
• Handling personal vs. business disagreements
• Translating personal core values into company culture
• The real impact entrepreneurship has on a marriage

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Avery and Owen are brothers who played football together at McKendree before turning a college side hustle into VIP Outdoors, a real lawn care and hardscaping company built around a model most people in the industry have never tried.

Instead of billing customers differently every month based on what's actually happening outside (mowing in the summer, leaf cleanup in the fall, snow removal in the winter), VIP Outdoors charges one flat rate, every single month, all year long. Mowing, landscaping, snow removal, all of it, wrapped into one predictable payment so customers never have to think about it. No surprise bills, no seasonal price swings, just one number they can count on twelve months a year.

In this episode of The Better Contractor, Brent sits down with Avery and Owen to talk about what it actually took to go from printing flyers in college to running a legitimate, scaling business, including the story of how one of their own customers, David St. John, became a mentor and eventually a co-owner.

In this episode:

• How two brothers went from playing football together at McKendree to starting a company together
• The moment they realized VIP Outdoors could be a real business, not just beer money
• How a customer became a mentor, then a business partner
• Why they built a flat rate, year round subscription model covering mowing, landscaping, and snow removal, and how customers actually reacted
• What building a business with your brother really costs you
• Balancing marriage, a new baby, and a growing company
• Why they want to build something bigger than themselves
• Their 5, 10, and 20 year goals for VIP Outdoors, and how big they actually want it to get

If you're a contractor thinking about recurring revenue, scaling past being "just a lawn guy," or building a business with family, this one's for you.

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Tommy took the traditional path to college and built a six-figure career in pharmacy—but along the way, he realized his real passion was building THE Landscaping Company, a high-end, full-service landscaping business that has already grown to nine employees. Now, he’s preparing to leave pharmacy behind and go all-in on taking his company to the next level. Tommy and Brent dive into what it takes to make that jump, covering sales, marketing, business growth, leadership, and the lessons Brent has learned from building his own company. Tommy also shares how much he’s grown personally throughout college and how that growth has prepared him for this next chapter as an entrepreneur. With plans to expand further into tree work and begin learning the ROW industry, Tommy is just getting started.

Follow Brent: @brentoberlink
Follow Tommy: @fivetooltommy

In episode 88 of The Better Contractor podcast, Alex, the host, asks entrepreneur Brent Oberlink how business owners can successfully delegate tasks to step back from daily operations while scaling their company. Drawing from personal experience with Lanracorp, Brent shares how outsourcing accounting and appointing a general foreman early on freed up valuable time to focus on the company's big-picture vision. The episode emphasizes that effective delegation requires high hiring standards, documenting natural processes into explicit job descriptions, and utilizing modern technology to automate redundant tasks. Key strategic hires, such as an executive assistant and a general manager, have allowed the speaker to confidently hand over responsibilities without micromanaging. 

Hiring the right people can grow your business, while the wrong hire can cost you time, money, and momentum. In this episode of The Better Contractor Podcast, Brent answers questions from our Facebook community about hiring, interviewing, determining pay, and knowing when it's time to let an employee go. Whether you're building your first crew or leading an established company, you'll walk away with practical advice you can apply immediately. Thanks to Forestry Rentals for sponsoring this episode, and don't forget to subscribe and join The Better Contractor Facebook Group to be part of future Q&A episodes.

What should you do when you’re booked months in advance but customers keep calling? Are you experienced enough to start charging for your work? Should you lower your price to keep a longtime customer?

In Episode 86 of The Better Contractor Podcast, Brent and Alex answer three real questions submitted by members of The Better Contractor Facebook group.

They discuss when contractors should hire more employees, rent or purchase additional equipment, raise their prices, turn down unprofitable work, and walk away from customers who only care about receiving the lowest bid.

Brent also shares advice for newer contractors who are still building their skills and confidence. You do not need to know how to handle every possible project before starting a business—but you need to understand your current capabilities, price your work appropriately, manage your liability, and continue improving.

In this episode:

00:00 Introduction
00:33 What to Do When You’re Booked Months in Advance
01:23 Hiring More Employees and Adding Equipment
01:48 When It’s Time to Raise Your Prices
02:32 Using a Premium “I Don’t Want the Job” Price
03:07 Turning Demand Into Business Growth
03:44 Starting a Contracting Business With Limited Experience
04:29 Managing Risk and Liability as a New Contractor
05:18 Choosing the Right Services to Offer
06:19 Building Confidence and Charging for Your Work
06:39 How New Contractors Should Set Their Rates
07:44 Starting Small and Growing Into Better Work
08:39 How Brent Started Lanracorp
10:00 Gateway Dealer Network Sponsor Message
10:52 Should You Match a Competitor’s Lower Price?
11:37 When to Walk Away From a Longtime Customer
12:14 Why Contractors Get Stuck at Break-Even
13:17 The Problem With Low-Barrier Competition
14:13 Becoming More Specialized and Valuable
15:17 The “Low-Low-Low Bid” Process
16:04 Lowest Price vs. Best Value Customers
16:42 Why Some Customers Come Back After Choosing the Cheapest Bid
17:18 Join The Better Contractor Facebook Group

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ABOUT THE BETTER CONTRACTOR PODCAST

The Better Contractor Podcast features real conversations about growing a contracting business, developing strong leaders, hiring and retaining employees, improving company culture, managing operations, and building a business that can succeed for the long term.

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In this episode of The Better Contractor Podcast, host Brent is joined by Mike Whalen of the Beyond the Belt podcast and DBS Remodel to discuss the critical challenges of attracting, training, and retaining high-quality workers in the trades. Drawing from over 25 years of experience, Mike provides a boots-on-the-ground perspective on transitioning from a business owner to a project manager and leadership team member.

In Episode 84, Brent Oberlink breaks down the sales strategies that helped grow his business. He covers the tactics he relied on in the early days as well as the systems and processes he uses today. He shares practical lessons on building relationships, earning trust, closing more work, and why great sales involve more than just offering the lowest price. Whether you're just starting out or looking to improve your sales process, this episode is packed with actionable advice you can apply to your business.

In Episode 83, Brent Oberlink shares how he grew Lanracorp into an 8-figure company through the power of marketing. From the early days of relying on relationships and word-of-mouth to building a personal brand and embracing social media, Brent breaks down how his approach has evolved over the years. He discusses what worked when he was getting started, why marketing became a priority, and the strategies he uses today to continue growing the business. If you're a contractor or business owner looking to stand out and build a stronger brand, this episode is packed with practical insights and lessons learned.

Welcome to The Better Contractor, a podcast dedicated to helping you build a more successful and professional blue-collar business. We tackle the tough questions about modern industry challenges, from the rapid rise of controversial data centers to the essential need for professional legal and accounting protection. Our discussions dive deep into the power of social media marketing, showing you how to tell your unique story to attract the right employees and customers. Featuring insights from industry veterans and marketing experts, we provide the educational and entertaining content you need to stay ahead of the trends. Join our growing community of thousands of contractors to network, learn, and elevate your business to the next level.