My Real Estate Journey: Reflections on 7 Years of Hard Work, Triumphs, Challenges and the Future

I got my California real estate license in January 2014. Over the next seven years, I experienced the highest highs and the lowest lows. I learned that hard work always pays off (even if not at first), relationships are paramount and that in order to be successful, I had to make real estate fun—for myself and my clients.

It is with much honor and privilege that I’m sharing my path with others who are considering a career in residential real estate. Real estate is not without its challenges, but it has been an extremely rewarding and fulfilling career path for me, one that I hope to continue for at least another seven years.  

In my late 30s I was lost and, frankly, a little frightened by my (limited) career options. I considered many different paths and decided to research residential real estate. I began by simply taking agents to coffee and picking their brains on the industry. I asked them questions about working with buyers and sellers, tough transactions, how to build a client base and gathered as many tips as possible. I also started interviewing different brokerages, eventually choosing Sotheby’s International Realty.

Ari Wintraub real estate.jpg

For me, choosing a brokerage came down to three things: Do I fit in here? Will they be able to help me reach my goals? And do I get along with the manager and my potential mentor? I quickly realized that my decision needed to be less about the actual brokerage and more about who I would be training with.

Beginning on day one, and every subsequent day in 2014, I spent as much time as humanly possible with my mentor and in the office, gathering as much information as I could from other successful agents—as much by watching and listening as talking. I was the first person to arrive at the office and the last to leave. I did anything and everything to put myself in the mix, to learn about the business.

Saturdays were reserved for open houses—I would sit any open house I could get my hands on. The day started at 7am, putting open signs out, and ended with gathering signs in my trunk as the sun was setting. I did grunt work for senior agents. I listened, I took notes, I tried every tool and strategy doled out by my manager at sales meetings. I also made it my mission to meet the unofficial quota of handing out a minimum of three business cards every day. If this sounds like a lot of work, you’re right, it was. And still is. But it’s worth it, because I love what I do.

My year one net commissions totaled $51,023. A solid start, considering other beginning agents around me shared that their first year nets were in the ballpark of $0 - $3,000 (for one small lease deal). 

Here’s a breakdown of my year-one deals to give you an idea of the range of sources from which a client can originate:

  1. A “gimme-client” from my mentor

  2. Investor I met at an outdoor music venue

  3. Seller I door knocked

  4. Buyer I got from sitting another agent's open house 

  5. Flipper client a senior agent didn’t have time for 

  6. Same new investor client who purchased a second property

  7. Friend who called me to find them a rental, but I proved they were better off buying

By year two, I’d gotten the train rolling and certainly with more confidence now that I had some solid deals under my belt. I was able to shed my part-time catering and assistant gigs and focus on real estate full time. I was still dedicated to putting in serious hours at the office, more than anyone else employed or licensed there.  

By the end of 2015, I completed nine sales, seven leases, and one referral fee, with a total of $11,500,000 in sales volume. My net commissions were $120,893. This is when I knew I had chosen the right second career.

The first two years in real estate were really about learning how to transact. I learned the ins and outs of contracts, negotiation skills and how to put deals together that were advantageous for both sides. My early success was 50% learning the hard skills, and 50% “handing out business cards,” as I like to say, or making connections. 

The subsequent years became all about how I was going to distinguish myself from the thousands of other agents in L.A. I had no family or large network of friends in the area, I am from Canada, so any potential clients would be based on newly formed relationships.

Ari Wintraub Sotheby's Realty.jpg

For me, it’s been about networking, getting to know as many people as possible and welcoming them into my sphere. I love social events and was able to grow my sphere through casual gatherings, happy hours, mixers and hosting networking events. My goal was to be the glue that brought people together.

In 2016, I broke into the eight-digit sales price market. This was a two-year process of low balling on houses for a high-net-worth contact of mine. Finally something stuck. This made my year and more than doubled my income from the previous year, totaling $375K in net commissions. 

My biggest takeaway from that transaction was to never cease sending a prospect market info, opportunities and check ins. Always strive to keep yourself top of mind to your sphere. Don’t be discouraged if it seems like they never respond, because when they do, it could be for a $10M sale.

In year three, I was also finally able to buy my first property. I purchased a turn-of-the-century craftsman that I gutted. Two days after moving in I turned 40 and threw a huge party with food trucks and DJs, and invited anyone and everyone I knew—about 100 people—and not only was it a prime networking opportunity, but it was also arguably the best night of my life. 

Purchasing the property was a major turning point for me. Not only was I good at helping clients purchase and sell real estate, I now owned property and would soon begin to leverage that asset.

Make no mistake, the early years were a grind. Consistent no’s. Constant losses. Endless work—as one might expect in a sales job. But the writing was on the wall, I finally had a career I could depend on. Then 2017 hit. My goal was to double my income, but instead it was reduced to half. Luckily I rebounded in 2018 and 2019 was the best year yet. 

In 2018 I bought my first multifamily investment property. I gutted three of the four units and learned a ton about real estate investments in the process. This became a new area of expertise and an additional service I was able to offer my clients. Through the years, I’ve also learned the importance of consistently being able to offer value to your clients, through new skills, knowledge and connections.

This brings me to now, the first quarter of 2021. So far, so good. I have three developer-focused listings and despite the economic unknowns, am excited about the year as a whole.

My year-eight goals include:

  • Hiring a full-time assistant 

  • Welcoming my first dedicated and highly-qualified team member

  • Welcoming a second team member by year’s end

  • Completing one syndicated real estate investment where I buy on behalf of others to operate and generate cash flow for passive investors 

  • Transacting at least $40M in total sales volume 

After seven years in real estate, I am definitely more weathered, but am also exponentially wiser, eternally optimistic, now wear an investor’s hat, and am continuously seeking ways to expand my income streams. Commissions are not my only goal, but remain a constant focus. 

And as I started this post with appreciation, so too shall I end it with equal parts gratitude and humility—for both my hard work over the years and the myriad opportunities. Here’s wishing us all luck and good fortune—newbies, oldies and all of us precious ones in between. 

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