Between Two Chairs - Demystifying Commercial Real Estate

Between Two Chairs - Demystifying Commercial Real Estate

di Fernando Arencibia, Jr. and Jennifer Wollmann
Imprenditoria
Stagione 4
What's A Buy Box and How to Build One Before You Buy Commercial Real Estate
In this episode of Between Two Chairs: Demystifying Commercial Real Estate, we break down one of the most important steps for any real estate investor: defining your “buy box.” Instead of chasing anything that looks like a “good deal,” we explain how investors can create a clear investment framework based on goals, asset class, location, price range, property quality, management expectations, and desired returns. The conversation explores why a buy box helps investors move from vague interest to focused decision-making. We discuss how an investor’s “why,” risk tolerance, available time, market knowledge, and personal experience should shape the types of properties they pursue. Topics Covered · How to define a commercial real estate buy box · The difference between chasing deals and following an investment philosophy · How asset class affects management intensity and risk · Why location analysis goes beyond liking a market · The role of demographics, zoning, and economic drivers · How to evaluate price beyond the purchase number · Why flexibility matters in real estate investing · How operational experience can create value · Lessons from Airbnb, multifamily, industrial, self-storage, hotels, land, and retail · How brokers can help investors clarify what they actually want to buy Successful investing starts before the search begins. By defining a buy box, investors can narrow their focus, learn their market, evaluate opportunities more objectively, and act with confidence when the right deal appears. The best buy box is not just about numbers; it should also reflect lifestyle goals, management capacity, risk tolerance, and the investor’s own strengths. Whether someone is buying a long-term rental, a short-term rental, an industrial box, a self-storage facility, or a small hotel, the key is to know how the property makes money, what could go wrong, what alternatives exist, and how the investor’s own experience can improve performance. If you are interested in investing in real estate and want help defining your buy box, reach out to Fernando and Jennifer to talk through the questions they use when evaluating their own investment criteria.
S4 · E171
23 lug 2026
35:45
Tax Strategies and Retirement Planning for Real Estate Agents: Interview with Chris Sierra CPA
A good friend of ours called one day and said, "You have to do a podcast episode on how to retire from real estate so agents and brokers don't have to work until their 90's -- unless they are able and want to." Gus Fonte an industrial broker and investor that we interviewed, knows the value of investing in what he knows and will be able to retire whenever he wants. We decided to interview Chris Sierra, CPA,to have him highlight the main steps to take at different stages of your real estate career. To set yourself up for a successful retirement as a real estate agenthere are some of his basic tips: structure your business properly, organize your finances, and invest consistently for the long term. To find out exactly how to do each of those steps, and what other ones to take at different stages of your career, pull up a chair and join us!
S4 · E170
16 lug 2026
1:01:07
Office-to-Residential Conversions and Adaptive Reuse in South Florida
From office space to living space, the conversation over converting unused office space has been a topic of conversation since COVID. In this episode, we look at office to residential conversions in South Florida via two distinct projects: The Hazel in Doral and The Hyve at Dadeland. The conversation highlights how highest and best use, land size, zoning changes, construction costs, floor plate challenges, parking, walkability, transit access, and surrounding amenities all influence whether an office building is preserved, converted, or torn down. Overall, the episode frames these projects as major bets on South Florida’s evolving real estate market, especially as developers look for ways to turn aging office properties into housing while better connecting them to the communities around them.
S4 · E169
9 lug 2026
22:57
When Should You Do A Phase I or II Environmental Assessment? Interview with Nicholas Moran
As part of a commercial real estate sale, you will most likely do a Phase I and maybe even a Phase II Environmental Assessment. In this episode, Nicholas Moran of Moran Rocks goes through the steps required to protect the buyer from environmental issues that may arise or already be present due to previous owner or tenant activities. Before you put in a offer, make sure the due diligence period will allow for the turnaround time for these important inspections. What is a reliance letter? How long does it take to complete a Phase II? What should you look for when walking a site? This discussion with Nicholas and his experience as a previous regulator, geologist and environmental consultant, provides our listeners with unique insights from both sides of the regulatory aisle.
S4 · E168
2 lug 2026
43:22
What Does The Current Economy Mean For The Miami Commercial Real Estate Market?
The beginning of the year predictions that interest rates would drop, has not happened and the current inflation rate actually indicates that there will probably be a rate increase before the year end. The war with Iran and the mid-term elections all add continued uncertainty in the market. That being said, retail vacancies are still low, shopping centers are in high demand with investors, Class A office space in many Miami markets is being absorbed, and immigration to Florida, while slower than it was, is still a positive. There is pressure on industrial and multi-family rental rates, but there investors are still bullish on the area, building housing under the Live Local Act or converting office to residential. In summary, Miami fundamentals are strong and capital is still flowing into CRE.
S4 · E167
25 giu 2026
29:49
How To Invest in Self Storage - An Interview With Lauren Rothlisberger
What do a military family, the Women's Investment Summit, and self storage have in common? Lauren Rothlisberger of Everett & Harvey and Serious Storage. In this episode Lauren shares her investment journey from residential rental properties into self storage and the nuances of being a General Partner. Her path hasn't been easy, because let's be real, real estate deals aren't easy, but it has been extremely well thought out. From the conscious tie to family with the business name to the details of scaling a business while living overseas, Lauren's background as a military wife plays a strong role in her investing and operating strategies. Three of the many takeaways include: 1) Assessing real risk vs perceived risk and backwards plan for worst case scenario 2) Always look at the repositioning options further down the road and 3) How to overcome the challenge of obtaining commercial financing when you are new to commercial real estate investing. Whether you are a current or aspiring real estate investor, this episode will provide you with insights into the self storage niche. Thank you for pulling up a chair!
S4 · E166
18 giu 2026
56:06
What Does It Take From A Logistics Perspective to Host the World Cup?
The World Cup starts today, June 11 and Miami will host our first match on June 15. Planning for this event, that will put Miami on the world stage again - we just wrapped up F-1, started as soon as Miami was awarded the 2026 World Cup four years ago. From fan transportation to and from the games and events, to the logistics of moving players, equipment, food and beverage to the stadium and events, there are a lot moving parts. Luckily for Miami, a lot of the infrastructure projects including the airports, stadiums and roadwork, had already been underway due to the growth the region experienced during COVID. I am sure there will be some challenges,
S4 · E165
11 giu 2026
22:35
Why Do So Few Commercial Real Estate Sellers Do 1031 Exchanges? A Conversation with Jon Hilley
What do Scrooge McDuck, The Square Grouper, Goldman Sachs, commercial real estate and taxes have in common? The answer is Jon Hilley, founder of 1031 Specialists. In this episode, we dive into why so few sellers do 1031 exchanges, what differentiates 1031 Specialists from other intermediaries and the Golden Strategy. Jon brings his wide range of experience, curiosity and his "Client Happiness Project" to elevate the 1031 experience. "We are in the joy business". FEA Economic Impact Studies of 1031 Exchanges
S4 · E164
4 giu 2026
49:53
Tourism, Tech & Tipping Points: What’s Fueling Miami Commercial Real Estate
What’s really driving Miami commercial real estate right now? In this episode, we break down the forces behind the market’s momentum—from record tourism and global events to tech growth, international investment, and shifting consumer demographics. Using the latest tourism trends and real-world examples, we explore how major demand drivers like Formula One, the World Cup, Art Basel, and eMerge Americas ripple through Miami’s commercial landscape. This isn’t just a hospitality story. It’s a conversation about how visitor growth fuels retail, industrial, office, mixed-use development, infrastructure, and the broader business ecosystem across South Florida. We also discuss how rising international travel patterns from regions like South America, Europe, Asia-Oceania, and Africa often become early signals for business expansion, capital inflows, and long-term investment activity. If you want to understand where the Miami commercial market may be heading next, this episode connects the dots between the numbers, the headlines, and the opportunities on the ground.
S4 · E163
28 mag 2026
24:28
Founder, Founder, Founder: Bob Gillespie on PropTech, AI, and What Actually Wins in Commercial Real Estate
In real estate it is all about location, location, location... In this episode we sit down with Bob Gillespie, Managing Partner of REACH Commercial at Second Century Ventures, to talk about what really drives success in PropTech. Bob shares his journey from computer science and startup operations to venture investing, and explains how REACH Commercial identifies technologies that can make commercial real estate faster, smarter, and more profitable. The conversation explores why commercial real estate has historically lagged in technology adoption, what makes a startup investable, and why Bob believes the founder often matters more than the initial idea. He also breaks down the biggest reasons PropTech companies fail, why traction is everything, and how associations can play a meaningful role in fostering innovation rather than just reacting to it. Bob also offers a candid perspective on AI in commercial real estate—what excites him, what makes him cautious, and why defensibility, workflow integration, and real market demand matter far more than hype. Along the way, he shares examples from companies in the REACH portfolio and gives listeners a rare inside look at how venture investors think about scale, adoption, and long-term value creation.
S4 · E162
21 mag 2026
54:13
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