Long Position

Hosted by Amy Calandrino

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146

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Oct 2026

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About the show

Long Position is a podcast about the decisions that actually build wealth, businesses, and communities. Hosted by Amy Calandrino, a commercial real estate advisor with nearly 20 years of experience working with entrepreneurs, investors, and families, the show explores what it looks like to think strategically, build intentionally, and play the long game in commercial real estate, business growth, and life. Each episode features candid conversations with the people doing exactly that: business owners scaling responsibly, developers shaping neighborhoods, family enterprises navigating succession, investors building lasting portfolios, operators rooting themselves in communities, and the advisors, architects, bankers, attorneys, and economic development leaders who help make it all work. These are not hustle stories. They are stories about ownership, legacy, patience, and the kind of thinking that compounds over time. Whether you are a founder evaluating your first building purchase, a family navigating a generational transition, an investor looking for smarter perspective, or simply someone who believes that long-term thinking is a competitive advantage, Long Position was made for you. Because the most important decisions rarely reward urgency. They reward clarity.

Listen to episodes

60 recent

October 21, 202642 min

The Long Game of Purpose-Driven Leadership with John Rivers

What if the next chapter of success is measured by what a community can grow? In this episode, we talk with John Rivers, founder of 4Roots Farm and 42 Acres and chairman of 4 Rivers, about turning business experience into service. Rivers reflects on leaving daily leadership at 4 Rivers, recognizing where his strengths fit, and trusting others to lead. He traces 4Roots’ roots to local food insecurity, then describes a wider concern: soil health, long food supply routes, waste, and the ties between food and public health. At 42 Acres, his teams are developing enzyme-based methods to shorten food-waste processing and convert certain plastics into a soil additive. Rivers sees technology as a partner to nature, and lasting change as work that starts locally, one school or neighborhood at a time. Listeners will hear how self-awareness, trust, patience, and service shape leadership, and why food, farming, and health belong together. In this episode, you will hear: John’s’ transition from CEO to chairman at 4 Rivers 4Roots Farm’s work on food insecurity and agricultural education The connection between soil health, food quality, and human health 42 Acres’ enzyme-based approaches to food waste and plastic Technology’s role in supporting farming and soil recovery Purpose-driven leadership, community service, and long-term thinking 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.

October 7, 202645 min

Strategic Real Estate Financing with Aaron Marsh

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 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.

September 23, 202645 min

Built to Last: What Decades in Business Teaches You About Wealth With Phil Calandrino

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.

September 9, 202638 min

The ROI of Investing in Creativity with Theresa Smith-Levin

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.

August 26, 202634 min

Building a Brand That Builds a Community With Christi Ashby

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.

August 12, 202649 min

How Great Investors Survive Every Market Cycle With Joel Kraut

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.

July 29, 202644 min

Navigate High-Stakes Situations While Building Lasting Success With Mark O’Mara

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.

July 15, 202633 min

Banking Relationships, Commercial Real Estate, and Smarter Decision Making with Dan Hilken

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.

July 1, 202649 min

Brand, Trust, and Leadership in a Noisy Market with Courtney Ettus

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.

June 17, 202636 min

Discipline Through Cycles, Contrarian Investing, and Building Enduring Value with Andy Weiner

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.