Real Estate for Real Life

Wilson Group
  • 5.0 (11)
  • Entrepreneurship

REFRL podcast highlights business-savvy individuals, operational systems, entrepreneurs, and life moments that real estate professionals encounter daily. This podcast is for general informational purposes only. The views, thoughts, and opinions of the guest represent those of the guest and not  Keller Williams Realty, LLC and its affiliates, and should not be construed as financial, economic, legal, tax, or other advice. This podcast is provided without any warranty or guarantee of its accuracy, completeness, timeliness, or results from using the information.

  1. Sep 1

    Episode 22 • From Selling a Business to Building a New One: The Money, Mindset & Risks Behind Entrepreneurship with Mark Condon

    What happens when you sell a business, suddenly have to figure out what to do with the money, and realize you don't actually understand your own finances? For Mark Condon, that moment completely changed the trajectory of his career. After running his own business from ages 21–32, Mark transitioned into financial services in 2017. Today, he's a financial planner helping individuals, families, and business owners navigate cash flow management, investment management, life and disability insurance, tax planning, retirement planning, and employee retirement plans. But that's only half of his entrepreneurial story. In 2022, Mark launched iPupPee, a physical product company created to strengthen the connection between dogs and their human owners. The idea grew out of Mark's experience hosting Boston's Best, where he interviewed Massachusetts entrepreneurs and business owners—including our very own Ryan Wilson. In this episode of Real Estate for Real Life, Ryan Wilson sits down with Mark to talk about what it really takes to build a business, manage money, take calculated risks, and turn an idea into something real. In This Episode, We Talk About: • The realities of entrepreneurship and business ownership • What Mark learned from running his first business • How selling a business led him into financial planning • The financial mistakes entrepreneurs and business owners commonly make • Why cash flow management matters more than revenue • Investing, tax planning, insurance, and building long-term wealth • How entrepreneurs can balance business growth and personal financial security • What it takes to turn an idea into a physical product • The story behind iPupPee and how Mark brought the concept to life • Taking risks, changing careers, and starting over • The relationship between money, mindset, and entrepreneurship Whether you're a real estate agent, entrepreneur, small business owner, investor, financial planner, aspiring business owner, or simply someone who wants to become better with money, this conversation is packed with lessons you can apply to your own life and business.  ABOUT REAL ESTATE FOR REAL LIFE Real Estate for Real Life goes beyond buying and selling real estate. Hosted by Ryan Wilson and Courtney Gauchman, the podcast brings entrepreneurs, business owners, industry experts, and leaders from outside of real estate to the table to uncover the strategies, failures, mindset shifts, and lessons that can help all of us build better businesses and better lives. Because the best business lessons don't always come from your own industry. CONNECT WITH MARK CONDON Website: vertexplanning.wpengine.com & ipuppee.com Instagram: @markcondon13 LinkedIn: Mark Condon https://www.wilsongroupre.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ @wilsongroup⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Produced by: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Taylor Bono⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Andy DeMattio⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ For inquiries or interest in becoming a guest on Real Estate For Real Life, email: Andy@WilsonGroupRE.com.

  2. Aug 24

    Episode 21 • The Hiring Mistakes That Can Cost Your Business Everything with Jen Scully & Meg O'Leary

    What if your biggest business liability isn’t your competition, your marketing, or your sales—it’s the way you manage your people? In this episode of Real Estate for Real Life, Courtney Gauchman and Ryan Wilson sit down with Jen Scully and Meg O’Leary, founders of Scully & O’Leary LLC, to unpack the side of entrepreneurship that most business owners don’t think about until there’s a problem: employment law, hiring, workplace conflict, employee benefits, and leadership. But this conversation goes far beyond legal advice. Jen and Meg built their firm together in 2024 after successful careers in government and employment law. Now, as business partners and best friends, they’re helping employers and employees navigate some of the most complicated moments in the workplace—all while building a business of their own. We talk about: → The biggest mistakes business owners make when hiring and firing → What entrepreneurs should know about the Massachusetts Wage Act → Why documenting workplace decisions matters more than you think →The risks surrounding Paid Family and Medical Leave → What business owners need to understand about AI and legal advice → Why educating your audience can be more powerful than simply selling your services → The reality of building a business with your best friend → How to know when you need an attorney BEFORE you have a problem → And the lessons Jen and Meg have learned about entrepreneurship, leadership, and building a business from the ground up This episode is a must-listen for entrepreneurs, business owners, leaders, and anyone responsible for hiring or managing a team. Because building a great business isn’t just about getting more clients. It’s about knowing how to protect the business and the people inside it. 🎙️ Real Estate for Real Life explores the real stories, strategies, and lessons behind building businesses, leading teams, and creating a life you actually want. Connect with Jen & Meg: Website: scullyandoleary.com Email: jen@scullyandoleary.com | meg@scullyandoleary.com Instagram: @scullyandoleary https://www.wilsongroupre.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ @wilsongroup⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Produced by: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Taylor Bono⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Andy DeMattio⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ For inquiries or interest in becoming a guest on Real Estate For Real Life, email: Andy@WilsonGroupRE.com.

  3. Aug 10

    Episode 20 • Build It to Sell It: What Makes a Business Truly Valuable with Matt Naimoli

    What actually makes a business valuable? For many entrepreneurs, the goal is simply to grow revenue, build a great team, and create a successful company. But what happens when you decide it’s time to sell? On this episode of Real Estate for Real Life, Ryan Wilson and Courtney Gauchman sit down with entrepreneur and M&A advisor Matt Naimoli of Legacy Advisors to talk about the lessons he learned from building, scaling, and ultimately selling his own business and how those experiences shaped the work he does today helping other business owners navigate acquisitions and exits. Matt shares what he learned from growing G&N Insurance into a nationally recognized company, the challenges of transitioning from founder to employee after an acquisition, and why systems, culture, leadership, branding, and recurring revenue can have a major impact on what a business is actually worth. The conversation also explores the surprising similarities between selling a business and selling a luxury home, from positioning and presentation to buyer psychology, negotiation, and creating competition. Ryan and Courtney also dig into Matt’s experience with EOS, building a personal brand, using creative marketing to stand out in a traditionally “boring” industry, and what entrepreneurs should be thinking about long before they ever decide to sell. Whether you own a business, are thinking about starting one, or simply want to understand what separates a good business from a truly valuable one, this episode is packed with practical lessons you can apply to your own entrepreneurial journey. In this episode, we discuss: • What makes a business valuable beyond revenue • Building a company with an eventual exit in mind • What happens to an entrepreneur's identity after an acquisition • How systems and EOS can help a business scale • The surprising connection between luxury real estate and M&A • Common mistakes business owners make before an exit • Lessons from Matt's journey as an entrepreneur and advisor Connect with: Matt Naimoli Website: www.legacy-advisors.com LinkedIn: linkedin.com/in/mattnaimoli Instagram: @mnaimoli Subscribe for more conversations with entrepreneurs, business leaders, and experts from outside the real estate industry and the lessons their experiences can teach all of us. https://www.wilsongroupre.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ @wilsongroup⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Produced by: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Taylor Bono⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Andy DeMattio⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ For inquiries or interest in becoming a guest on Real Estate For Real Life, email: Andy@WilsonGroupRE.com.

  4. Jul 28

    Episode 19 • The Airplane Ride That Changed Everything | How Lauren Sherlock Built Big Little Pies Lauren Sherlock w/ Co-Host Pam Foley

    Can one airplane ride change your life? ✈️🥧 For Lauren Sherlock, the answer is yes. After years in consulting, Lauren found herself burned out and questioning her career. Then, during a work flight, she watched a pie-making video that sparked an idea she couldn't ignore. Less than a year later, she left corporate America and launched Big Little Pies, despite having zero experience in the food industry or entrepreneurship. In this episode of Real Estate for Real Life, hosts Courtney Gauchman and Pam Foley explore Lauren's incredible journey from corporate consultant to small business owner. They dive into entrepreneurship, branding, taking calculated risks, and why some of the best business ideas come from the most unexpected moments. If you've ever dreamed of starting a business, changing careers, or building something that aligns with your passion, this episode is for you. You'll learn: ✔️ How Lauren knew it was time to leave her corporate career ✔️ The unexpected story behind Big Little Pies ✔️ What it's really like starting a business from scratch ✔️ Branding lessons every entrepreneur can use ✔️ How to navigate uncertainty while growing a small business ✔️ Why community can make all the difference when launching a new venture About Lauren Sherlock Lauren Sherlock is the founder and owner of Big Little Pies, a Boston-based bakery specializing in handcrafted mini pies. Before launching her business in 2024, Lauren worked in healthcare and nonprofit consulting. Her entrepreneurial journey began with an unexpected moment during a work trip and has grown into a thriving business built on creativity, resilience, and a willingness to take a leap of faith. Connect with Lauren 🌐 https://www.biglittlepie.com 📸 Instagram: @biglittle.pies https://www.wilsongroupre.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ @wilsongroup⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Produced by: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Taylor Bono⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Andy DeMattio⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ For inquiries or interest in becoming a guest on Real Estate For Real Life, email: Andy@WilsonGroupRE.com.

  5. Jul 17

    Episode 18 • How Cause Marketing Builds Better Businesses (And Changes Lives) | with Arianna & Ryan Wilson, Alex's Team Foundation

    On this episode of Real Estate for Real Life, Courtney Gauchman sits down with Arianna Wilson, Executive Director of Alex's Team Foundation, alongside Ryan Wilson, President of the Foundation, for a conversation about purpose, leadership, and the power of cause marketing. After losing her twin sister, Alex, to leukemia at just 16 years old, Arianna's family founded Alex's Team Foundation to honor Alex's life by funding groundbreaking pediatric cancer research, supporting healthcare professionals, and creating meaningful programs for children and families facing cancer. Today, Arianna has helped transform that personal mission into a growing nonprofit through strategic partnerships, community engagement, and corporate philanthropy. But this episode isn't just about nonprofit work. It's about why businesses that align with a meaningful cause build stronger brands, create deeper customer relationships, and inspire employees and communities in ways traditional marketing simply can't. Whether you're a business owner, entrepreneur, nonprofit leader, or simply someone looking to make a greater impact, this conversation offers practical insights into how purpose and business can work together to create something much bigger than profit alone. In this episode, we discuss: How Alex's Team Foundation was created from unimaginable loss Turning personal purpose into organizational impact What cause marketing really is, and why it works How businesses can partner with nonprofits authentically Building strategic partnerships that benefit everyone Creating a culture of giving within your company Why community engagement is good for both business and society Ways individuals and companies can make a meaningful difference If you enjoyed this episode, be sure to subscribe to Real Estate for Real Life, where we bring together entrepreneurs, business leaders, and innovators from every industry to uncover lessons that help us grow both professionally and personally. About Arianna Wilson Arianna Wilson is the Executive Director of Alex's Team Foundation, a nonprofit dedicated to fighting childhood cancer through pediatric oncology research, nursing support, patient and family programs, and strategic community partnerships. Through her leadership, she has expanded the Foundation's reach by building meaningful relationships with corporations, community leaders, and supporters who share a commitment to making a lasting impact. Learn More Alex's Team Foundation: www.alexs-team.org Spirit Ball: www.atfspiritball.com Instagram: @Alexsteamfoundation  Connect with Arianna Wilson to get involved: Instagram: @amiliotis08 Email:  arianna@alexs-team.org _ https://www.wilsongroupre.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ @wilsongroup⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Produced by: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Taylor Bono⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Andy DeMattio⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ For inquiries or interest in becoming a guest on Real Estate For Real Life, email: Andy@WilsonGroupRE.com.

  6. Jul 6

    Episode 17 • How Top Businesses Scale Without the Founder Doing Everything with Johnny Ibrahim

    What does it really take to scale a business without becoming the bottleneck? In this episode of Real Estate for Real Life, Courtney Gauchman and Ryan Wilson sit down with Johnny Ibrahim, Head of Business Development for Shant Banosian's industry-leading mortgage team at Rate, to unpack the systems, relationships, and leadership strategies that have helped build one of the nation's highest-producing lending teams. Johnny shares his journey from sales assistant to leading an entire business development division, revealing why the best entrepreneurs stop trying to do everything themselves and instead build teams that allow everyone to operate in their zone of genius. Together, they discuss: • Why business is built on relationships—not sales • The follow-up systems that keep you top of mind (and dramatically increase referrals) • How to create value that clients and partners actually remember • Why every growing business eventually needs a business development role • Using CRMs, routines, and AI to stay organized and maximize productivity • The leadership lessons behind scaling without losing culture• Building trust through education instead of selling • The role social media plays in staying relevant and strengthening relationships • How great leaders empower their teams instead of trying to control everything Whether you're an entrepreneur, business owner, real estate professional, or anyone looking to build a business that lasts, this conversation is packed with practical strategies you can implement immediately. If you've ever wondered how top-performing businesses continue to grow year after year while maintaining exceptional relationships, this episode is your blueprint. 🎙️ Real Estate for Real Life is the podcast where business leaders from every industry share the lessons, systems, and mindset that help entrepreneurs build stronger businesses and better lives. Connect with Johnny Ibrahim Website: shantgr.com Instagram: @johnnyibs @shantbanosian  Facebook: https://www.facebook.com/johnibs https://www.wilsongroupre.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ @wilsongroup⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Produced by: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Taylor Bono⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Andy DeMattio⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ For inquiries or interest in becoming a guest on Real Estate For Real Life, email: Andy@WilsonGroupRE.com.

  7. Jun 29

    Episode 16 • What Every Entrepreneur Can Learn from the Hospitality Industry with Jason Pound

    What if your biggest business opportunity was hiding in a place everyone else overlooked? In this episode of Real Estate for Real Life, host Ryan Wilson is joined by special guest co-host Jimmy Chao for a conversation with entrepreneur Jason Pound, founder of Finesse Hospitality Services. Jason shares how he built a thriving business by elevating one of the most overlooked parts of the guest experience—and why entrepreneurs who obsess over the little things often create the biggest competitive advantage. From identifying untapped opportunities to building a company rooted in exceptional customer service, Jason explains how a hospitality-first mindset can transform any business. Whether you're in real estate, hospitality, or another industry entirely, this episode is packed with practical lessons on entrepreneurship, leadership, and creating experiences that people remember. In this episode, you'll learn: How to spot business opportunities that others miss Why customer experience is your greatest competitive advantage The difference between providing a service and creating an experience Lessons on scaling a service-based business without sacrificing quality How hospitality principles can elevate your business—no matter your industry If you're an entrepreneur, business owner, or someone looking to stand out in a crowded market, this conversation will challenge the way you think about growth, service, and innovation. Subscribe to Real Estate for Real Life for conversations with entrepreneurs, business leaders, and industry experts sharing the lessons that apply far beyond real estate. Connect with Jason Pound Website: fhsboston.com  Instagram: @fhsboston LinkedIn: Jason Pound LinkedIn https://www.wilsongroupre.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ @wilsongroup⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Produced by: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Taylor Bono⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Andy DeMattio⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ For inquiries or interest in becoming a guest on Real Estate For Real Life, email: Andy@WilsonGroupRE.com.

  8. Jun 19

    Episode 15 • No Call Goes Unreturned: How Scott Kriss Built a National Real Estate Law Firm

    What does it take to grow a business from a small startup into a nationally recognized company, without losing the personal service that made it successful in the first place? In this episode of Real Estate for Real Life, Ryan Wilson and Courtney Gauchman sit down with attorney and entrepreneur Scott Kriss, founder of Kriss Law/Atlantic & Affiliates, to discuss the lessons he's learned building one of the most respected names in the real estate legal industry. Scott shares how he launched his own firm less than a year into his legal career, the risks he took early on, and the systems, standards, and leadership principles that helped fuel decades of growth. He also dives into the importance of communication, creating a service-first culture, and what real estate professionals can learn from the closing table. Whether you're a business owner, real estate professional, or entrepreneur looking to scale, this conversation is packed with practical insights on growth, leadership, client experience, and building a reputation that lasts. In This Episode: ✔️ The biggest lessons from scaling a service-based business ✔️ How acquisitions have fueled growth ✔️ The philosophy of "no call goes unreturned" ✔️ What top real estate agents do differently ✔️ Common mistakes that create issues during closings ✔️ Leadership lessons from decades in business Connect with Scott Kriss: Website: www.krisslawatlantic.com Instagram: @krisslawatlantic LinkedIn: https://www.linkedin.com/company/kriss-law-atlantic-closing-escrow Facebook: www.facebook.com/krisslawatlanticclosings/ https://www.wilsongroupre.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ @wilsongroup⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Produced by: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Taylor Bono⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Andy DeMattio⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ For inquiries or interest in becoming a guest on Real Estate For Real Life, email: Andy@WilsonGroupRE.com.

See All (23)

Ratings & Reviews

5
out of 5
11 Ratings

About

REFRL podcast highlights business-savvy individuals, operational systems, entrepreneurs, and life moments that real estate professionals encounter daily. This podcast is for general informational purposes only. The views, thoughts, and opinions of the guest represent those of the guest and not  Keller Williams Realty, LLC and its affiliates, and should not be construed as financial, economic, legal, tax, or other advice. This podcast is provided without any warranty or guarantee of its accuracy, completeness, timeliness, or results from using the information.

Information