Real Estate for Real Life

What happens when two entrepreneurs take their expertise in mental health, coaching, and performance and turn it into a business designed to help young men thrive?

In this episode of Real Estate for Real Life, Ryan Wilson and Patrick Hopkins sit down with ⁠Jotham Busfield,⁠ LICSW, and ⁠Jon Cunha⁠, LMHC, co-owners of ⁠Riser+Tread⁠, to talk about entrepreneurship, mental health, resilience, performance, and building a business with a deeper purpose.

Jotham's entrepreneurial journey began after an unexpected career pivot from architecture to clinical social work. After starting his first business in 2013, he eventually partnered with Jon to launch Riser+Tread in 2019. Today, they have built innovative programs that support young men through therapy and coaching, including their ADHD in 8, Sports Performance + Recovery, and Golf programs.

We dig into the thinking behind their business model, what they've learned from building a company together, and how their work with youth and male clients has shaped the way they think about resilience, performance, and personal growth.

In this episode, we talk about:

• Making a major career pivot and finding a new purpose

• Building and scaling a service-based business

• What makes a strong business partnership

• The connection between mental health and high performance• Resilience and why it matters in business and life

• Supporting young men through therapy and coaching

• The business model behind Riser+Tread

• What entrepreneurs can learn from the world of mental health and performance

Whether you're an entrepreneur, business owner, parent, coach, or simply interested in becoming a better version of yourself, this conversation offers a different perspective on what it means to build something meaningful.

CONNECT WITH Jon & Jotham from Riser & Tread

Learn more about ⁠Riser+Tread⁠

Instagram: ⁠https://www.instagram.com/riserandtread/⁠

LinkedIn: ⁠https://www.linkedin.com/company/riser-and-tread-llc⁠

Facebook: ⁠https://www.facebook.com/riserandtread/⁠

⁠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: ⁠[email protected]⁠.

A beautiful cake gets people talking. What turns that attention into a thriving business?

On this episode of Real Estate for Real Life, hosts ⁠Courtney Gauchman⁠ and guest host ⁠Rachael Smith⁠ sit down with ⁠Michelle Scurio⁠, owner and cake artist behind Cake Monstah, to explore her journey from a high school DECA project to building a luxury cake business.

From sculpted edible art to nationwide wedding cake tasting boxes, Michelle brings a creative perspective to entrepreneurship and the work of turning a personal passion into an experience clients remember.

We explore:

• Building a distinctive brand in a competitive industry

• Balancing creative ambition with profitability

• Creating meaningful client experiences during life’s biggest celebrations

• Finding opportunities to innovate and grow

• The lessons that come with turning your craft into your career

Whether you’re growing a business, pursuing a creative passion, or rethinking your customer experience, this conversation offers inspiration and practical questions to bring back to your own work.

Meet the entrepreneur behind the cakes and discover what goes into building a business people celebrate.

Subscribe to Real Estate for Real Life for more conversations with entrepreneurs and leaders across industries.

Connect with Michelle/Cake Monstah:

Website: ⁠Cakemonstah.com⁠

Instagram: ⁠@cake.monstah⁠

Email: ⁠[email protected]⁠

⁠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: ⁠[email protected]⁠.

What does it take to become the #1 mortgage originator in the United States?

In this episode of Real Estate for Real Life, Ryan Wilson and Courtney Gauchman sit down with Shant Banosian, President of Rate, to unpack the mindset, systems, and leadership principles behind one of the most successful careers in the mortgage industry.

After originally planning to attend law school, Shant discovered a passion for helping people navigate one of the biggest financial decisions of their lives, a journey that has since led him to help more than 40,000 families secure over $10 billion in home loans.

Together, they discuss:

• How Shant built and scaled one of the highest-performing teams in the country

• The habits and systems behind sustained success

• Leadership lessons from growing a world-class business

• Why "who you work with" matters more than ever in today's housing market

• The real cost of waiting to buy a home

• Advice for first-time homebuyers, entrepreneurs, and business leaders alike

Whether you're a Realtor, lender, entrepreneur, or simply someone looking to level up your career, this conversation is packed with practical insights on leadership, execution, and building a business that lasts.

Connect with Shant:

Website: ShantBanosian.com

Instagram: @ShantBanosian

LinkedIn: linkedin.com/in/shantbanosian

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: [email protected].

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: [email protected].

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: [email protected] | [email protected] 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: [email protected].

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: [email protected].

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: [email protected].

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:  [email protected]

_

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: [email protected].

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: [email protected].

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: [email protected].