W2 to Freelancer

Written by Tyler Kastelberg

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Happy Sunday!

While you’re reading this, I’m frantically packing for our first family vacation with a toddler. My wife and I are at an impasse about whether or not we should haul our son’s car seat through the airport for the off chance that we can get an open seat for him to strap into … you can probably guess where I stand in this debate.

This week, I’m going to share some wisdom from one of our busiest freelancers, Asheeh Patel, about making the switch from a W2 commercial real estate job to full-time freelancing. If you prefer to skip the summary and read the full interview, you can do that here

First – if you’re new here, subscribe to this newsletter. I send one weekly email on Sundays with content relevant to CRE.

Who is Asheesh?

As I hinted above, Asheesh is one of the busiest freelancers at Bullpen. So much so, that he was able to leave his full-time, W2 job to pursue freelancing full-time.

Asheesh graduated with a degree in Economics from UCLA and, like many of us, didn’t consider real estate as a career option until an internship in the field, where he managed property in Beverly Hills. 

From there, he moved to an Irvine-based multifamily and hospitality investment firm where he worked on acquisitions and asset management before eventually heading to the University of Southern California for an MBA. While a dual full-time employee and MBA student, Asheesh decided to leave his full-time job to freelance.

Why become a freelancer?

According to Asheesh, the benefits he’s experienced as a commercial real estate freelancer are highly impactful to his career. Some of the benefits he highlighted include the following. 

1. Flexibility. Asheesh started freelancing shortly before leaving a full-time role, while continuing his part-time MBA program. Because client needs vary from part-time to full-time, freelancing can fit a wider range of life and career situations than a traditional W2.

2. Focus. Freelancing also provides an opportunity to niche into a particular focus area that you may not be able to touch in a traditional commercial real estate role. For Asheesh, his role in asset management was great but didn’t leave much room to be proactive, hunt for deals, and learn beyond his core job function.

Asheesh says he knows many early to mid-career real estate professionals often choose employment based on the reputation of the employer, often leaving them with less interesting work that may not be in their ideal job function. In his own words, “the positive of freelancing is that it gives the person a passion project. If the goal is to own a multifamily shop but you’re working in financial services, freelancing gives that ability to go seek out your passion or long-term goal area and work more creatively in it.” 

Bullpen’s freelancing role took Asheesh from being a more reactive asset manager to a more proactive acquisitions associate, responsible for underwriting transactions but also sourcing his own deals. “It’s a credit to my client, I’ve had the opportunity to build relationships with brokers and keep track of a deal pipeline.”

Prospective freelancers take note – Freelancing gives you a chance to build unique skills that you may not otherwise be able to do at a big company. 


That’s all for this week. I’ll be back next Sunday with an interview with one of our freelance affordable housing experts. It’s full of interesting info, including how to identify top markets and the difference in market-rate and affordable underwriting.

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