Making Career Moves in Real Estate: The Things I Learned Transitioning from a Hedge Fund to a Real Estate Investment Firm

Jan 31, 2015 | Career

The blog has always been a mix of personal insights and guest posts from guys I think are smart and doing interesting things. Guest posts are great because they provide a perspective that I can’t. For instance, I get a ton of career-related questions, and while I can provide general advice, I haven’t looked for a job in 5+ years! I tap my network to identify friends who can share anecdotes that resonate with people and fill that void.

I’m really excited to share today’s guest post from Kevin Vaughan because it perfectly addresses so many of the questions I get on a regular basis. Kevin reached out to me back in September 2014. He wrote a succinct email about his background, passion for real estate, and requesting “15 minutes” to talk. He also offered to share his notes from a conference he was planning to attend; two lessons he’ll address below.

We went back and forth a few times and scheduled a time to meet for coffee. Over that next week I had 2 friends who I trust and respect reach out saying they spoke with Kevin and recommended that he and I connect (not knowing Kevin and I had already connected). We hadn’t even met yet, and I knew he was doing something right. After we met for coffee in early October he followed up with a thank you email, and over the following weeks kept me updated on his job search and not surprisingly, let me know he landed a job with a best-in-class shop. Kevin did such a textbook job networking that I asked him to put together a post detailing what he learned and advice he has for others looking to begin career in real estate.

This is a bit longer than the usual post, but for anyone looking for a job in real estate or looking to advance in their career, it’s a must-read.

Enter Kevin:

Advice must always be taken with a grain of salt, as each individual’s career journey is framed by his life experiences, by his network, by his innate talents, and by his personality. An important factor in my search was the framing of the advice I received from others, taking into account the above factors when analyzing the advice I was presented. I encourage the readers of this post to do the same, to find the parts that resonate with their personal path, to challenge those that don’t, to process these words knowing that someone wrote them with his own goals, beliefs, and experiences in real estate.

For my first 2.5 years out of college, I worked in the fundamental equity investment arm of a hedge fund based in New York. I had always held an interest in the real estate world and the built environment, having studied Architectural History and Theory, and was lucky enough to begin working for the real estate vertical of the fund in a REIT analyst/trader capacity. The experience was invaluable to my real estate and finance education, and I respected and admired the friends I worked with, but I had the unwavering desire to be closer to single assets. We were looking at portfolio valuations of real estate operating companies, and we rarely studied single assets. When I began networking and interviewing for roles at real estate PE shops, developers, and in the real estate arms of banks, most of the professionals I ran into didn’t view what I did as truly being part of the real estate market. While frustrated at first, I now tend to agree. I wasn’t in the real estate world in its true form, and I had to prove to people I could add value to their team despite my lack of single asset experience. I’ll be the first to admit – my transition was not smooth, was not quick, and was not without moments of failure and pessimism. After a few hard months of networking and interviewing, I was able to earn a spot in the real estate investment arm of a global hotel owner, investor, and operator. Below I provide a few bullets to break down the more salient aspects of my recent job search experience. I hope a point or two here may help those of you on the brink of landing a great opportunity in the real estate world.

Build Momentum

Upon deciding to shift gears into any career, it is pivotal that you have tangible goals and real checkpoints to assess progress along the way. Looking for a new job, as they say, is often a full time job in and of itself. Make this potential dual work period as short as possible by being vigilant in your studies and preparation from the onset – going half-hearted towards a goal can lead to a long, arduous process. Rather, put in a few hours each and every day to network, study, and build skills, and you will find that, with some initial patience, doors will open in waves. The real estate world is hiring; put yourself in a position to take advantage of it today.

I’m a big believer in the psychological powers of momentum and inertia. When people in the routine of doing certain tasks each day, it is hard to break that routine. Make it easy for yourself and feed off your own momentum with a checklist of things to do every single day of your job search. Email one real estate contact a day, follow up with one person that you haven’t spoken to recently, read three real estate articles, work on one type of model, etc. Identify the skills and knowledge you need to perform in your ideal role and shape a checklist accordingly.


Successful networking during the job search is the result of two factors: engaging and following up. You have to hustle, you have to go to events, you have to scour your current network of family, friends and coworkers for contacts in the real estate world. That’s the easy part. The hard part is getting contacts to help you out. They are busy people. They might be powerful people. They might barely know you. This is when you have to be truly engaging and specific regarding your purpose for engaging. Believe me, I was far from engaging to many of my initial contacts and there are certainly those with whom I could have done a much better job. I like to think I improved as time passed. But if you are thoughtful and engaging in your initial outreach, you will have a far easier time getting to the point of helpful conversations and action. To this end, you need to know your audience. Have a good article to send to your target person, relevant to his or her business, and have an opinion on it. Ask for 15 minutes on the phone (enough that you are serious, but not too long so as to take valuable time) to speak about the real estate world, what you’d like to do, and how that person might help. Most successful people love helping others, and know that they wouldn’t be where they are without a few lucky contacts along the way. If they have a disinterested attitude, it’s more probable that you just aren’t striking the right chord (and blaming them for being disinterested is futile, anyway). I found that keeping a list of interesting articles was pivotal to my success here. Every day, I would try to find two or three really good articles, file them, and create a one-sentence summary for each. That way, whenever I wanted to reach out to someone new, I could pull up my file and almost always find a pertinent article to cite in conversation.

Secondly, follow up! Send an email the day after conversations, thanking your contact for his time. Ask him for a few contacts that he recommends based on your aspirations. The goal here is not to ask every contact if he or she is hiring, or knows anyone that is. The goal is, rather, to connect, impress, and keep your name on all radar systems. That way, when each of your contacts is asked to recommend someone for an analyst or associate role, your name is on the short list. To people with whom you have a strong connection, send an email every few weeks keeping them informed of your progress. Keep your name in front of everyone. Patience, something I have had to work on, is key here. You may get antsy after a few months of networking with no actionable conversations or offers, but, if you connect and impress, you will find that things will start to fall your way. For me, it took about four to five months of hard networking, studying, conversations and follow-up conversations with dozens of great people before I started landing final round interviews and offers. All of a sudden, I found things started moving in waves. This is the lag effect of networking – the opportunities might not be available when you first reach out, but if you make a strong impression, you will benefit in the future when there are openings available. The real estate world is small; if you impress people, your name will be mentioned for opportunities in due time. The process is a fine mix of hustle and patience.


Within your networking, I recommend speaking to people from an array of real estate sub-sectors and roles. Everyone you talk to has a unique perspective, and an opinion on how to be successful. The advice you get will be a product of the real estate vertical in which your contact works, the types of assets he deals with, whether he is on the principal or service side, his education, his office location, etc. In NYC, many employers want to see analysts and associates for both buy and sell-side roles come from banking or lending platforms. HR at these firms won’t even let your resume through otherwise, and that’s ok. Smaller developers might not want that institutional type of employee—they might want someone with a project management or construction background, or just a go-getter that is smart and has opinions on the real estate world. Some investors will only invest after doing the most complex of multi-scenario sensitive modeling, while others eschew that type of complexity in favor of back-of-the-envelope type analysis, paired with construction or operational expertise. Know what kind of person you are talking to, and take advice accordingly. Identify what kind of life you want live, the real estate people you most admire that live those lives, and make sure to pick their brains once a month. They will be your jungle guides on your job search.

Show, Don’t Tell

Ok, so you have identified the people you want to reach out to, the type of life you may want to live in the future, and you are now omniscient regarding real estate current events. You know that you will be a stud analyst for any firm if given the opportunity. Now you need a way to convince your network and target companies of your skills. Why should they hire you? You are fluent regarding markets, deals, valuation, and the like, but you need to be able to show people you are competent. Real estate valuation is not very complex. But most employers like to think it’s a lot harder than it is, and don’t like taking hiring risks. This is probably the most important piece of advice here. You have to be able to show your competence, not just speak to it. You simply have to be able to model basic real estate transactions for the vast majority of real estate investment and development jobs, and you need to be able to field questions regarding those models. and’s products regarding real estate finance and valuation skills cover what you need for most jobs. Often times, analyst or associate roles will have modeling tests for you. I recommend beating your prospective employer to the punch—have three basic models you have built (e.g. an office, apartment, and lodging model) and stay fluent on how you built it and what it’s telling you about the hypothetical asset’s investment potential. Print these models and take them with you to interviews. Make your prospective employer comfortable with your skills, so that she can check the proverbial box and you can move the interview towards discussion that favors you and your strategic selling points.

In addition to modeling, many younger associates at real estate firms will help put together investment memos and presentations to clients or an investment committee. This requires writing and presentation skills. I had to do very little writing and presenting in my former job, so I didn’t have that to speak to in my interviews. Instead, I drafted a writing sample and presented its arguments in my interviews. My sample was a four-page recap and analysis of a conference I had attended, wherein I detailed the pivotal discussions of the conference, offered rebuttals of my own, and laid out an argument for the direction of the real estate market. In interviews, when the person would ask of my writing skills, I would take out a clean, stapled copy of my memo, ask my interviewer to read it when she had time, and discuss the main features of the piece. The reaction was always positive. Outside of interview purposes, having an updated hard copy of your thoughts on the real estate market on paper is always a strong move. It shows you are organized, driven, and analytical. It not only serves as a great prop for interviews, but also serves as an excellent document attachment on networking emails to prove your legitimacy to new contacts.

Know the Firm

One complaint I had in talking to many older contacts is that a typical interviewee knows very little about the firm at which he is interviewing. People often prepare for interviews on a macro level, rather than focusing on the firm’s strategy, assets, people, and how they can fit into a role. By the end of every interview, the employer should be able to answer the simple but pivotal question: how is this person going to help make money for my firm? This part of preparation doesn’t take long. Do an hour of research on the firm’s recent transactions and current investments/developments. If it’s a public company, read the transcript from the latest quarterly earnings conference call. Have an opinion on how these things compare to actions taken by other real estate firms, and have a question or two regarding firm direction.  Impressing here is merely a matter of doing your homework.

Goal Setting

From the onset of your search, it is important to identify your long-term career and life goals and seek firms and roles accordingly. This is not to say that you need to identify a distinct path for yourself. In fact, I think doing so is quite dangerous. It is difficult, nearly impossible, for anyone in her twenties to know exactly the type of role she will want five, ten, twenty years down the road, because our perspectives change. Instead of focusing on a certain singular role you see yourself having in twenty years, focus on gaining the fundamental skills and network to be able to pursue an array of roles within the field. Your perspective WILL change, but the fundamentals that will make you successful will not. Make sure you’re prepared for that change of perspective, and arm yourself with the tools to succeed.

Here is a checklist of action items from my job search:

  1. Create a momentum checklist for each day or week and perform daily knowledge and skill-building tasks.
  2. When networking, engage with relevant articles or opinions and follow up. Stay on the radar for any opening that comes across any contact’s desk.
  3. Learn how to construct basic models. Have hard copies of two or three models of different building types on you at all times and bring copies to interviews and informal meetings.
  4. Put your thoughts on the real estate market onto paper, and have hard data to support your thesis. Bring hard copies to interviews.
  5. Find a few jungle guide whose careers you respect and make time to catch up consistently.
  6. Arm yourself with the fundamental tools and attitude to succeed in any role, knowing that your perspective will change.

I’d love to hear your thoughts and experiences starting off in the real estate world. I can be reached at [email protected]