Long Position

Hosted by Amy Calandrino

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142

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Aug 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

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.

June 3, 202644 min

From Purpose to Production: Building a Career, Reputation, and Results in CRE

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.

May 20, 202642 min

Reinvention, Specialization, and Building a National CRE Brokerage With Brittany Megrath

Commercial real estate is rarely a straight line, and Brittany Megrath’s journey proves it. From professional ballet dancer and Las Vegas showgirl to founder of a national commercial real estate brokerage, Brittany built M Square Commercial by leaning into reinvention, discipline, and a willingness to specialize where others stayed broad. We explore how Brittany carved out a niche representing STNL developers and expansion tenants on ground-up retail developments across the country. What began with cold outreach during the uncertainty of COVID evolved into long-term relationships, national deal flow, and a brokerage model centered around one highly specific type of transaction. The conversation also breaks down how STNL development really works behind the scenes, from sourcing land and evaluating trade areas to navigating environmental challenges, municipal approvals, and shifting retail trends. Brittany explains why relationships remain the foundation of the business, especially in an industry where deals can take years to materialize, and local market knowledge still matters more than ever. Listeners will learn about retail development, tenant expansion strategy, and why specialization and consistency can create long-term success in commercial real estate. In this episode, you will hear: Transitioning from performing arts to commercial real estate Discipline and mindset from elite performance Building a focused brokerage niche How STNL development actually works behind the scenes National tenant expansion strategy Entrepreneurship and starting M Square Commercial 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.

May 6, 202642 min

Faith, Identity, and the Decisions That Shape Legacy with Michael Walker-Thomas

Faith, discipline, and identity are not formed in a single moment. They are built through the quiet, consistent decisions we make every day. In this conversation with Michael Walker-Thomas, educator, author, poet, and mentor, we explore how purpose is discovered and shaped over time through mindset, faith, and intentional living. Michael reflects on his journey from a young writer who used poetry for self-expression to becoming a published author and mentor. Grounded in faith, he shares how spiritual practices structure his daily life and shape his approach to both creativity and high-stakes decisions. A major focus of the discussion is the tension between authenticity and social pressure, especially for younger generations navigating constant digital influence. Drawing from his experience in education, Michael highlights the importance of imagination, mentorship, and developing confidence rooted in self-awareness rather than external validation. We also explore how to recalibrate when life feels misaligned, through reflection, prayer, and intentional habits that create clarity and direction. Listen in to learn how faith can guide decision-making, how discipline builds identity, and how the choices we make today ultimately shape the legacy we leave behind. In this episode, you will hear: The spiritual foundation behind disciplined living The tension between social validation and purpose Writing as a calling Educating young men in a distracted world Faith as a daily structure Long-term thinking in a short-term culture 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.

April 22, 202641 min

Owning Your Brand, Owning Your Career, Owning Your Life with Andy Storch

What if the biggest driver of your career growth isn’t just the work you do, but how you’re known for it? In this episode, we sit down with Andy Storch, author, speaker, and career and personal brand strategist, to unpack the powerful connection between brand ownership, career progression, and life design. We explore the idea that personal brand is not about self-promotion or social media presence alone, but about your reputation. In today’s fast-paced and competitive environment, Andy explains why simply “doing great work” is no longer enough. Visibility, relationships, and intentional positioning play a critical role in unlocking new opportunities. The conversation dives into how brand shows up both internally and externally. From how you collaborate within your organization to how you share information publicly, every interaction contributes to your overall perception. Andy emphasizes that being mindful and intentional about these moments can significantly impact your trajectory. A major focus is self-awareness as the foundation of brand clarity. By understanding your strengths, values, and what you want to be known for, you can align your actions with your long-term vision. We also discuss the importance of balancing confidence with humility, setting boundaries, and sharing your journey in a way that feels authentic rather than promotional. In this episode, you will hear: Why personal brand matters more than ever How your reputation impacts real opportunities What intentional career ownership looks like How Andy’s journey intersects with broader decisions in business, real estate, and pivot moments 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.

April 8, 202638 min

Strategy, Trust, and Brand in Commercial Real Estate with Reid Bennett

Strategy, trust, and brand are no longer separate pillars in commercial real estate, they’re deeply interconnected, and Reid Bennett has built his career at that intersection. In this conversation, we explore how he has differentiated himself in a crowded CRE landscape by combining thoughtful deal strategy with a consistent and authentic personal brand. Reid shares a key shift in mindset: success isn’t just about who you know, but who knows you. By leaning into visibility and creating content that resonates, he’s been able to build trust at scale, often before ever speaking with a client. The conversation also dives into how Reid navigates complexity in today’s market. Rather than acting as a transactional broker, he positions himself as a strategic advisor, someone who understands market nuance, crafts compelling narratives around assets, and identifies the right buyers through intentional targeting. We also touch on the importance of consistency, discipline, and ongoing professional development. From earning his CCIM designation to embracing the daily fundamentals of the business, Reid emphasizes that long-term success is built through repetition and focus. Listeners will learn how to build credibility, stand out in a competitive industry, and align strategy, trust, and brand to create lasting success in commercial real estate. In this episode, you will hear: How professionals create differentiation in a crowded CRE market Why strategy and thinking matter as much as execution How personal brand supports long-term influence and opportunity Where Reid sees the market heading and how leaders should prepare 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.