Long Position

Most people think a mortgage is just a rate and an approval, but Aaron Marsh, Founder of Marsh Lending, shows how financing can become a core part of a wealth strategy. We talk about how growing up in a real estate family shaped Aaron’s approach, why he built a firm around relationships instead of one-off transactions, and how he uses lending structures to support a client’s long term goals rather than just the next closing.

Aaron walks through how he thinks about risk, liquidity, and using debt thoughtfully so investors are prepared for market shifts. We also explore his “five mile famous” philosophy and what taking a true long position looks like for both business owners and real estate investors.

In this episode, you will hear:

• Treating lending as a strategy and partnership instead of a one-off transaction
• How DSCR loans work and why they appeal to real estate investors
• Creative options for entrepreneurs and “HENRY” borrowers who do not fit traditional bank criteria
• Using debt thoughtfully to balance growth, risk, and liquidity through different market conditions
• Why real estate remains a powerful wealth-building tool for business owners and investors
• The “five mile famous” approach and what taking a long position means for both investing and business building

Resources from this Episode

Instagram: marshlending

amycalandrino.com

creorlando.com

thecalandrinofoundation.org

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Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com. Let them know we sent you.

Built to last companies rarely happen by accident. We talk with Phil Calandrino, Founder & Attorney at Forward Law Firm and Amy’s husband, about what nearly three decades of advising business owners has taught him about turning a business into lasting wealth.

Phil explains why execution usually matters more than having a brand-new idea, how process and delegation separate an owner with “a good job” from someone who owns a truly valuable company, and why planning your exit from day one changes how you build.

We explore the shift from reacting to crises to protecting what you have created, the legal and structural blind spots owners often miss, and when to start thinking beyond the operating company to family wealth. Phil and Amy also share how they are raising their own kids to think about money, risk, and opportunity, and what today’s founders should do if they want their work to still matter decades from now.

In this episode, you will hear:

• What separates durable companies from those that burn out
• Execution and process mattering more than a brand-new idea
• Moving from owning a job to owning a valuable, sellable company
• Delegation, the “monkeys on your back” metaphor, and the five levels of delegation
• Shifting from only growth to also protecting what you have built
• Turning business income into family wealth and planning an exit from day one
• Preparing the next generation to think about money, risk, and opportunity

Resources from this Episode

IG: philcalandrino

amycalandrino.com

creorlando.com

thecalandrinofoundation.org

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review,” then a quick line with your favorite part of the episode. It only takes a second, and it helps spread the word about the podcast.

Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com. Let them know we sent you.

What if the arts are about far more than entertainment? Theresa Smith-Levin, Founder and Executive Director of Central Florida Vocal Arts, sees the arts as a powerful way to build connection, confidence, and community. We explore how her organization has expanded access to arts education and performance opportunities while growing into a lasting community presence. Theresa shares lessons on leading with clear values, building authentic relationships, and continuing forward even when the path feels daunting.

We also discuss the challenges of balancing leadership, motherhood, passion, and burnout and why communities benefit from investing in arts and culture. We close by considering what it means to make choices that reflect who we are and the future we want to build.

In this episode, you will hear:

• Building community through the arts
• Leading with clear values and authentic relationships
• Balancing passion, leadership, motherhood, and burnout
• The role of arts education in confidence, courage, and belonging
• Investing in arts and culture to strengthen communities
• Making long-term choices that align with your values

Resources from this Episode

amycalandrino.com

creorlando.com

thecalandrinofoundation.org

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review,” then a quick line with your favorite part of the episode. It only takes a second, and it helps spread the word about the podcast.

Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com. Let them know we sent you.

In this episode, we introduce you to Christi Ashby, founder and publisher of Orange Appeal, and her perspective on local media, leadership, and Orlando’s growth. We hear how a childhood love of magazines led to a women-focused publication launched in 2008 as the economy collapsed and how small businesses and nonprofits helped keep the magazine alive.

Christi shares how she earns reader trust, chooses stories that highlight real women, and balances staying in her lane with evolving as the community changes. She and Amy talk about cash flow, patience with big organizations, and why relationships matter more than quick wins. Christi also reveals the story behind Orange Appeal’s new Orlando International Airport store and what it means for local makers.

Listeners learn how long-term thinking, generosity, and consistency can steadily build a brand and strengthen a city.

In this episode, you will hear:

• Launching and surviving as a media brand during the 2008 financial crisis
• How trust, consistency, and relationships shape local storytelling and advertising
• Highlighting women, nonprofits, and small businesses before they are widely recognized
• Lessons on cash flow, patience with large organizations, and long-term thinking in business
• Views on leadership, motivation, and building community through everyday kindness

Resources from this Episode

amycalandrino.com

creorlando.com

thecalandrinofoundation.org

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review,” then a quick line with your favorite part of the episode. It only takes a second, and it helps spread the word about the podcast.

Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com. Let them know we sent you.

Longtime investors do not win because they find magical properties; they win because they choose the right people, think clearly, and stay patient through every cycle. We talk with Joel Kraut, Founder of BRRRR Loans and author of 7 Steps to Financial Freedom, about why real estate is more about partners, discipline, and emotional resilience than cap rates and quick flips.

Joel shares hard lessons from losing millions during the 2008 crash, what he changed in his approach, and why peace of mind now ranks higher than luxury or speed. We explore how to build a portfolio that can survive downturns, why many investors underestimate reserves and overestimate their risk tolerance, and how clear financial goals and simple daily habits compound over years.

Listeners hear real-world advice on choosing partners, thinking long term in any market, and building a life they actually want, not one they are just trying to survive.

In this episode, you will hear:

• Why real estate success starts with people and partnerships, not properties
• Thinking in decades instead of deals and building real financial foundations
• Choosing calmer, simpler investments over high-stress “perfect” returns
• The role of patience, discipline, and clear 12‑month financial goals
• How mentorship, continuous learning, and giving back shape long careers
• Building a life you actually enjoy instead of a business you are just surviving

Resources from this Episode

amycalandrino.com

creorlando.com

thecalandrinofoundation.org

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review,” then a quick line with your favorite part of the episode. It only takes a second, and it helps spread the word about the podcast.

Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com. Let them know we sent you.

Success under pressure is never accidental. It is built through preparation, integrity, and a commitment to doing the right thing when the stakes are highest. In this episode, we sit down with Mark O'Mara, Founder and Lead Attorney of O'Mara Law Group, to explore how more than four decades in the legal profession have shaped his approach to leadership, decision-making, and long-term success.

Mark reflects on his journey from prosecutor to nationally recognized trial attorney, sharing how listening, empathy, and careful preparation have guided him through some of the country's most scrutinized legal cases. He discusses what it takes to stay focused when emotions are running high, why reputation is earned through consistency rather than talent alone, and how integrity influences every professional decision.

Mark shares lessons from navigating intense public attention, explains why strong leadership requires letting go of control, and offers practical advice for professionals looking to grow beyond technical expertise.

We also explore the role of commercial real estate in long-term wealth creation, balancing business growth with investing, and why meaningful success comes from showing up every day, doing the work, and thinking beyond the next opportunity.

In this episode, you will hear:

• Leadership under pressure
• Decision making when the stakes are highest
• Building trust and credibility over decades
• Growing a professional services firm
• Long-term wealth creation through business ownership and commercial real estate
• Staying calm when everyone else is emotional

Resources from this Episode

https://www.omaralawgroup.com/+

amycalandrino.com

creorlando.com

thecalandrinofoundation.org

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review,” then a quick line with your favorite part of the episode. It only takes a second, and it helps spread the word about the podcast.

Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com. Let them know we sent you.

Building a successful business takes more than ambition. It requires long-term thinking, trusted relationships, and strategic decisions that create lasting value. We have a conversation with Dan Hilken, Regional Market President at Seacoast Bank, to discuss the lessons he's learned from working with small and medium-sized businesses through decades of economic cycles.

Dan shares why resilient business owners invest in experienced advisors, prioritize thoughtful planning, and focus on sustainable growth instead of short-term gains. We also explore how commercial real estate can become a powerful wealth-building tool, when owning property may make more sense than leasing, and why finding the right balance of leverage creates flexibility and long-term opportunity.

The conversation also examines the value of relationship banking, highlighting why trust, integrity, and ongoing strategic conversations are often more valuable than transactional thinking. Looking ahead, we discuss why Orlando continues to be a strong market for entrepreneurs and business growth, along with advice for building a business that can adapt through changing markets while creating lasting success.

In this episode, you will hear:

• What decades of working with SMBs teaches you
• Commercial real estate as a wealth strategy
• Relationship banking vs transactional banking
• Building institutions that last
• Orlando, opportunity & the future of SMBs

Resources from this Episode

amycalandrino.com

creorlando.com

thecalandrinofoundation.org

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review,” then a quick line with your favorite part of the episode. It only takes a second, and it helps spread the word about the podcast.

Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com. Let them know we sent you.

What makes a company stand out when everyone is competing for attention? Courtney Ettus is Chief Marketing Officer of REsimplifi, Inc., and a respected voice in commercial real estate, brand strategy, and leadership. In this episode, she shares why trust, consistency, and authenticity matter far more than marketing tactics in today's crowded marketplace. Drawing on a career spanning fashion, global media, technology, and commercial real estate, she explains how strong brands are built by understanding people, solving real problems, and delivering on promises over time.

The conversation examines the growing role of technology and AI in commercial real estate, including how better data can support smarter decisions without replacing human judgment. Courtney offers insights into leadership, visibility, and the importance of helping organizations clarify their core values in ways that resonate with clients and stakeholders.

Beyond business strategy, we discuss mentorship, collaboration, and the importance of creating opportunities for others, particularly women in commercial real estate. Listeners will come away with valuable lessons on brand building, trust, leadership, and how long-term success is created through credibility, community, and a genuine commitment to serving others.

In this episode, you will hear:

• How strong brands are built intentionally
• Why trust and clarity matter more than ever
• What leaders get wrong about marketing
• How storytelling influences real business outcomes
• How careers and companies are shaped by visibility, community, and strategic positioning

Resources from this Episode

amycalandrino.com

creorlando.com

thecalandrinofoundation.org

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review,” then a quick line with your favorite part of the episode. It only takes a second, and it helps spread the word about the podcast.

Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com. Let them know we sent you.

A failed family retail business, a changing industry, and a willingness to think differently became the foundation for a career built on discipline, adaptability, and long-term value creation for Andy Weiner. Andy is the Founder and CEO of RockStep Capital, and on this episode, we talked about what it takes to invest successfully through multiple market cycles while staying committed to a clear strategy.

While headlines often focus on the impact of e-commerce and shifting consumer habits, he explains why strong retailers continue to expand and why limited new construction of shopping centers has created favorable supply-and-demand dynamics for owners. He shares how RockStep identifies opportunities in what it calls "Hometown America," focusing on growing communities outside major metro areas where quality of life, population growth, and local engagement drive long-term success.

The conversation also examines the importance of underwriting discipline, conservative use of debt, and the patience required to walk away from deals that do not meet strict investment criteria. Andy discusses why complexity often creates opportunity, particularly in retail and enclosed malls, where fewer investors are willing to do the deep work required to uncover value.

Listeners will gain insights into contrarian investing, navigating uncertainty, building resilient teams, and creating enduring value through disciplined decision-making, community engagement, and a long-term perspective.

In this episode, you will hear:

• Investing through cycles, not chasing them
• Why retail is misunderstood and still full of opportunity
• The discipline required to operate over decades
• Revitalizing communities through real estate
• Building a values-driven company culture that lasts

Resources from this Episode

www.rockstep.com

Andy Weiner on LinkedIn: https://www.linkedin.com/in/andy-weiner/

amycalandrino.com

creorlando.com

thecalandrinofoundation.org

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review,” then a quick line with your favorite part of the episode. It only takes a second, and it helps spread the word about the podcast.

Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com. Let them know we sent you.

Commercial real estate is often portrayed as a business built on connections, confidence, and instant success. But for C’jon Armstead, the journey started with uncertainty, cold calls, and a willingness to show up every day, even when the results were not immediate. In this conversation, we explore how discipline, consistency, and long-term thinking helped him transition from philanthropy and sales into the fast-paced world of investment sales with CBRE Capital Markets in South Florida.

C’jon shares the reality of building a career in CRE from the ground up. He explains why consistency matters more than occasional bursts of motivation and how daily execution compounds into meaningful opportunities over time.

We also discuss the role personal branding and social media have played in accelerating trust and visibility early in his career. By publicly documenting his prospecting journey, C’jon created accountability, built authentic relationships, and differentiated himself in a crowded marketplace.

Along the way, we explore leadership, goal setting, mentorship, and the mindset required to sustain growth without losing sight of family, purpose, and personal fulfillment. You will learn about prospecting, building relationships, creating opportunities, and developing a career rooted in intentionality and persistence.

Listen in for a grounded perspective on what it really takes to build lasting success in commercial real estate.

In this episode, you will hear:

• Entering commercial real estate from a non-traditional background
• Building credibility early in a competitive industry
• The discipline behind capital markets execution
• How brand and visibility accelerate trust
• Translating purpose-driven work into performance-driven outcomes

Resources from this Episode

Instagram: @cjonarmstead

https://www.cbre.com/people/cjon-armstead

https://www.linkedin.com/in/cjonarmstead

amycalandrino.com

creorlando.com

thecalandrinofoundation.org

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review,” then a quick line with your favorite part of the episode. It only takes a second, and it helps spread the word about the podcast.

Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com. Let them know we sent you.