The Eight People You’ll Meet in a Real Estate Transaction

Profiling the motley crew of characters from Thesis Driven's first course: the Fundamentals of Commercial Real Estate

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On March 2-3 we’ll host Thesis Driven’s first course, "Fundamentals of Commercial Real Estate." The course will take a case-based learning approach around a fictional mixed-use project, Harbor Yards.

The course will follow the trials and tribulations of eight characters who acquire, redevelop, operate and sell Harbor Yards over a five-year period. By understanding each player’s incentives—financial and otherwise—participants will get a practical, hands-on grasp of how the commercial real estate industry works. (We think it’s particularly useful for people who recently joined real estate-adjacent companies but don’t have an industry background.)

This newsletter will introduce these eight characters, which students will come to know intimately over the two-day bootcamp:

  • Michelle - Managing Director & Partner, Elevated Properties

  • Adam - Asset Manager, Elevated Properties

  • Ian - Investor, Whitestone Capital

  • Patrick - Property Manager, JBRE

  • Ollie - Office Leasing Agent, JBRE

  • Rachel - Retail Leasing Agent, JBRE

  • Alfred - Apartment Leasing Agent, JBRE

  • Leon - Lender, Bells Margo Bank

Disclaimer: all characters, companies and events in this course are fictitious. Any similarity to actual persons or events is purely coincidental.

Fictional Photo: Harbor Yards, a mixed use project on the waterfront in Big Apple City

Welcome to Harbor Yards

Harbor Yards is currently a tired, mostly vacant, 200,000 square foot office complex on the waterfront in Big Apple City.

It used to house a combination of advertising and startup technology companies, but many of these companies moved out after the 2020 pandemic, leaving the project in financial distress. The previous owner could no longer afford to make its monthly loan payments, so Bells Margo Bank, the lender, foreclosed on the property and is now selling it.

Keen to take advantage of the situation, Elevated Properties, a commercial real estate firm focused on value-add opportunities, is buying the property with plans to convert it into a mixed-use community with office space, retail, and apartments.

Meet the Characters

Michelle - Managing Director, Elevated Properties

Michelle, 47, is the Managing Director of Elevated Properties. Harbor Yards is her vision and she will stop at nothing to bring it to life.

Michelle is a hard-charging executive with a "work hard, play hard" mentality. She’s put in 14-hour days since she graduated Harvard Business School, working at several prestigious real estate private equity firms before leaving to start Elevated with her two partners. When she’s not working, she’s usually kite surfing in Morocco or heli-skiing near her home in Park City.

Michelle’s days start at 5am with a personal training session, followed by a triple shot latte and a 30-minute commute from her uptown apartment to her new office near Harbor Bay, where she requires the entire company to be in five days a week (except Summer Fridays). She spends most evenings at dinners with investors and industry executives, or working on her newest passion project, a start-up dedicated to creating ergonomic office furniture that doubles as gym equipment.

Clockwise from top left: Michelle, Adam, Ian, and Patrick

Adam - Asset Manager, Elevated Properties

Adam, 36, is Michelle’s right-hand-man and Asset Manager at Elevated Properties. Harbor Yards is his big career opportunity, and he needs to make sure it is a massive success.

Adam would be described by his newly ex-girlfriend as someone who is anxious and insecure, and uses the fact that he went to Princeton to make others feel inferior, including her. But his mother would say he’s been highly focused and motivated since kindergarten, when he created a spreadsheet to track the number of answers his classmates got right/wrong each day.

Adam’s days start at 6am with a 1-hour planning session of his daily goals, key meetings and a critique of his performance from the day before. He then walks 30 minutes to work and listens to the Huberman Lab or How to Talk to Girls podcast (he’s really excited about the new Thesis Driven podcast too), or calls his mom. He spends his days at the office with a packed schedule of meetings and calls, eating lunch and dinner at his desk. Most nights he stays at work late to ensure he achieves the goals he set that morning, but he never misses his Thursday night networking group with five Ivy Club alumni.

Ian - Investor, Whitestone Capital

Ian, 63, is the self-made billionaire founder and principal investor of Whitestone Capital, where he invests his own money–which he made importing car stereos from Japan– into real estate projects and cleantech investments. He is Michelle’s leading LP investor in Harbor Yards.

Ian didn't go to college but his ambition and street smarts catapulted him into the ranks of the world's most successful automotive entrepreneurs. He lives between Big Apple City, Calm Beach and St. Toritz. He doesn’t own a computer, managing all his investments from his phone and through secretaries.

Ian starts his day (usually on his yacht) before dawn, meditating and reading industry reports over a cup of black coffee. His life looks to most like a neverending vacation, but he is working constantly and has blurred all lines between work and play. His evenings are often spent in quiet reflection or hosting intimate dinners with fellow visionaries, where conversations range from existential philosophy to the future of urban living.

Patrick - Property Manager, JBRE

Patrick, 51, serves as the Property Manager for Harbor Yards, overseeing its daily operations like a proud watchdog. He was previously the Assistant Property Manager at a trophy building uptown, and is now relishing his position at the helm of this innovative project.

Patrick started his career as a lighting manager for theaters and television studios, and got into property management by accident when he was brought in on a lighting assignment for a commercial office building… and never left. He loves being the "boss" of the building, but feels like he is constantly under Adam’s microscope and can’t understand why he works twice as hard as Ollie and Rachel but for half the pay.

Patrick spends his mornings making sure his two high school children are fed before they catch the bus, and then he has an hour-ish commute into Big Apple City from his Old Jersey suburb. His day is a whirlwind as soon as he walks through the door, dealing with a never ending stream of tenant requests, vendor and contractor issues, and nagging check-ins from Adam. There is no such thing as lunchtime for Patrick – he eats whenever he starts feeling light-headed. He usually leaves the building around 6: 30 for the hour-long commute home, which he usually spends talking to Adam or listening to a science fiction book on tape.

Ollie - Office Leasing Agent, JBRE

Ollie, 37, is the charismatic "life of the party" of the Harbor Yards team and responsible for courting high profile companies to the project. Given the recent challenges in the office market, Ollie needs this exciting new project to lease so he can keep making car payments on his two Range Rovers.

Ollie started at JBRE out of college twenty years ago, when his Uncle Ralph gave him a job as the Junior Associate on his 8-person team. He had a hot start to his career when he landed a large hedge fund client for Ralph off a cold call and took home a $750,000 commission in his first year. Since then Ralph has been building his book of business with Big Apple City’s top financial services clients, doing most of his business on the golf course and the "19th hole" (he hasn’t been in the office on a Friday since 2008).

Ollie doesn’t subscribe to the notion that "the early bird gets the worm". His wife Sabrina gets the kids off to school while he answers emails in bed, and then waits for traffic to subside before starting his 45-minute commute into the city (unless he’s golfing that day). His days are filled with tenant tours, lunches with other brokers and potential clients, and usually dinners or drinks after work – sometimes for business, and other times with his University of Michigan fraternity brothers, "Go Blue". Entertaining is a big part of his job, so he’s no stranger to late nights.

Clockwise from top left: Ollie, Rachel, Alfred, and Leon

Rachel - Retail Leasing Agent, JBRE

Rachel, 29, is the strikingly attractive retail leasing agent for JBRE and forbidden love interest of Ollie. Harbor Yards is her opportunity to bring together the dream mix of trendy restaurants and luxury stores that will make Harbor Yards the place to see and be seen – both day and night.

Rachel’s career ambitions shifted from being a buyer for Neimann Marcus to a retail real estate broker two years ago when her parents told her they were taking away her credit card and making her responsible for paying her Big Apple City rent. She applied for a job in marketing at JBRE, but was convinced in her interview that brokerage might better suit her interests in luxury retail. She works with Amanda, a Senior Vice President who is twenty years Rachel’s senior and lives vicariously through her.

Rachel’s mornings are largely dictated by the night before, but she usually makes it out of bed for the 7am Barry’s Bootcamp class, followed by a $10 matcha latte on her walk home. She works from home in the morning – answering emails and taking calls from clients. Her afternoons are filled with touring clients through potential spaces and taking new business prospects out to her new favorite oyster bar. At nights she’s either networking at fundraising galas or watching Real Housewives with her new boyfriend, Trevor, an investment banker at Silverman Jachs.

Alfred - Apartment Leasing Agent, JBRE

Alfred, also 29, is part of the new residential brokerage group at JBRE, and will oversee the marketing and leasing of Harbor Yards new apartment units. Leasing Harbor Yards is "something to do" for Alfred until he figures out his next career move.

Albert’s grandfather started buying small, Class B & C multifamily buildings in Big Apple CIty fifty years ago. Albert went to work for the family business after college, first with the family’s in-house property management group and then their leasing team. He expected he’d take over the family business at some point, but then his father, who had taken over as Managing Partner, decided to sell the portfolio along with their services business, which was bought by JBRE, and moved to Mexico with his new wife. Albert was not pleased.

Albert, determined to find new ways to build his own wealth, spends his mornings listening to podcasts on crypto trading and other web3 trends. He ubers around 10am to Harbor Yards where he works out of the leasing suite and meets prospective tenants for tours (and sometimes his friends disguised as prospects to play 9 holes on the golf simulator in the amenity center). He operates relatively autonomously, rarely going into JBRE’s headquarters. Once tours are complete for the day, he’s back home ordering Postmates, watching Netflix, and reading crypto news.

Leon - Lender, Bells Margo Bank

Leon, 55, has been with Bells Margo Bank’s credit group for the last 33 years. He recently had to foreclose on Harbor Yards’ previous owners, and then was convinced by Michelle, with whom he’s had a longstanding relationship, to sell her the building and provide her a new loan to finance the mixed-use redevelopment plan. His associates were skeptical, but he believed in Michelle and was willing to put his reputation on the line for her and the project.

Leon’s days have looked the same for the last three decades since he graduated Lehigh as captain of the track team. He wakes up at 430am, heads out for a 5-mile run in his tree-lined suburban neighborhood, then hits the Starbucks drive-through with his wife – a ritual they started together after their two kids left for college two years earlier. His wife drops him off at the train station, where he commutes 45 minutes into his Uptown office in Big Apple City. He spends his days talking to Adam and other asset managers, checking in on the financial performance of his loans (more recently these are stressful conversations given the troubled state of office buildings), looking at new loan requests, and building relationships with Michelle and other real estate investors. He’s almost always on the 5:47pm train back home, answering emails and texting with his kids before getting home to make dinner together with his wife.


The Thesis Driven course will cover a detailed "day in the life" of each of these characters, using the Harbor Yards project to highlight their roles in the commercial real estate ecosystem and the relationships between them.

Course attendees will come away with a fundamental understanding of how a commercial real estate project is acquired, redeveloped, operated and sold, and at the end of the course will apply what they’ve learned to help write the business plan for a new and exciting project at Harbor Yards.

They’ll also learn to read a pro forma, building budget and lease; understand the relationship between a "GP" and "LP"; and be armed with a new vocabulary of industry lingo.

Spots are mostly filled, but we’re still accepting applications. Sign up here.

–Paul Stanton and Brad Hargreaves

Recommend Thesis Driven to the readers of Devon's wanderings

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A guest post by
Co-founder and partner at Proptech Bankers. Connecting real estate, technology and capital.
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