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.
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Booking probability
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80/100
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Episode #144
Built to Last: What Decades in Business Teaches You About Wealth With Phil Calandrino
Sep 23, 202645 min
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.
Building a Brand That Builds a Community With Christi Ashby
Aug 26, 202634 min
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.
How Great Investors Survive Every Market Cycle With Joel Kraut
Aug 12, 202649 min
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.
Navigate High-Stakes Situations While Building Lasting Success With Mark O’Mara
Jul 29, 202644 min
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.
Banking Relationships, Commercial Real Estate, and Smarter Decision Making with Dan Hilken
Jul 15, 202634 min
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.
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