Top 4 Real Estate Career Paths to Drive Your Financial Future

When I first started to analyze the real estate market in my hometown of Boston through the eyes of a future investor, nothing seemed to make sense. Upmarket homes sold for what seemed like exorbitant sums, whereas average quality housing stock often lingered unwanted on the market for months until a week or so after the sellers conceded to a too-deep price cut. Fixer-uppers flew off the shelves, but often for pennies. Of course, I never realized their potential when those fixer-uppers made their brilliant new debut after being turned into mansions in a few months’ time.

At the time, I didn’t fully appreciate that high selling prices were a result of money invested in improvements and effort spent on negotiations and favorable appraisals. Nor did I ever think that I could be one to benefit from pouring more gas into such a hot market. Since then, I’ve dabbled in several real estate career paths. 

From creating property valuation software—don’t try that at home—to shopping for undervalued homes in developing neighborhood markets and evaluating REITs as investment opportunities, there’s always been a lot to learn and a lot of opportunities to make more money by having an edge in knowledge. Most of all, I learned that picking the right role in real estate isn’t easy, and it helps to have some guidance along the way. To get you started, I’m going to share some of that choice guidance with you so that you’ll be the master of your financial future. 

Understanding Real Estate Career Paths

While there are a plethora of different real estate career paths, some are more lucrative than others. Plus, not every role is ideal for every personality or skill set. Being an appraiser, mortgage underwriter, or home inspector probably isn’t a good fit for someone with an entrepreneurial bent or desire to become an investor. 

Overall, investors and entrepreneurs stand to make the most money with a career in real estate, though you’ll need a bit more capital to start. And, most of the time you’ll need to be willing to risk your capital to make money, so it isn’t for everyone. If the idea of being an independent investor or business owner appeals to you, there are a handful of careers to consider, including:

  • Wholesaler
  • House-Flipper
  • Landlord
  • Franchisee

Let’s look at each of these real estate career paths in detail so that you’ll get a better idea of their daily responsibilities and challenges.


If the idea of being a middleman appeals to you, real estate wholesaling might be a good career path. Wholesalers put undervalued or decrepit properties under contract, then sell them to a buyer who’s also looking for a bargain. 

Typically, wholesalers buy distressed homes from auctions, foreclosures, or individuals that need cash quickly. In practice, the way this works is that you’ll sign a contract to purchase a home in the next month. That gives you 30 days to find a buyer for the house. The most common type of buyer will be a real estate investor or house flipper of some kind. 

Wholesalers wear a lot of different hats, including:

  • Negotiating rates with buyers and sellers
  • Conducting market research to identify lucrative areas with a lot of prospects
  • Scanning for properties that are being sold cheaply
  • Valuing properties 
  • Coordinating with developers, landlords, and other buyers

Having a strong network of investors to pitch to is critical for wholesalers, and the entire profession lives and dies on social skills—not to mention driving a hard bargain. Developing a pitchbook and cultivating a good reputation with investors will be a constant and high-value process. In contrast to other real estate career paths, wholesales rarely need to coordinate with contractors or real estate agents, and their interaction with sellers may be quite minimal too. 

Wholesaling is a good starting point for people seeking a career in real estate because it doesn’t require much capital to start. After all, you’ll never actually have legal control of the properties that you put under contract, because you’ll never be closing the deal yourself. Thus, much of the risk of real estate investing falls on buyers rather than the wholesaler. On the other hand, your burden as a wholesaler will be to pitch opportunities to buyers such that you can get them to pay more than the price you put the home under contract for. 

Given that the buyers you’ll be pitching properties to are keenly attuned to the value of real estate, finding a margin can be difficult. Wholesalers may not make that much on any individual transaction, which means that you’ll need to close a lot of deals to pay the bills. Some wholesalers churn through several contracts a month—but that’s only possible in markets that are overflowing with prospects. Still, wholesaling is a great opportunity to learn about multiple roles within the real estate industry at the same time, and there aren’t any credentials that you need to get started. 


In general, house flippers plan to buy homes for below the average market price, invest a small amount to improve the value of the property, and then resell it at a markup that’s hopefully larger than the amount of money they invested. House flipping tends to have a negative connotation, and you might think that it’s a path to quick riches.

As it turns out, it takes a tremendous amount of time, effort, and skill to successfully identify and rehabilitate undervalued or bargain bin properties. As a house flipper, you’ll develop skills like:

  • Identifying profitable opportunities
  • Renovating the parts of a home that add the most value to its future sale price
  • Coordinating with buyers and sellers 
  • Communicating with home inspectors, real estate lawyers, and contractors

Some people dislike flippers because they have a reputation for making shoddy improvements to their properties which make them look more expensive but are actually poor-quality. If you choose to buy and resell homes for a living, that part will be up to you. The more you invest in a home, the higher the asking price it will command, but the larger the up-front costs will be for you. And, there’s always a small chance that you’ll increase the value of a home beyond the price that the local market can reasonably support.

So, one of the biggest challenges of flipping is finding a healthy profit margin after deducting the transaction costs and refurbishing fees. But, liquidity is also a major concern. You’ll be taking on a significant liability every time you buy a home to flip, as your properties don’t generate any cash flow so long as they’re empty and in poor condition. And if your investments into a fixer-upper don’t sweeten the pot enough to attract prospective buyers, you might need to call the contractors again. 

Getting started as a flipper can be difficult. Growing your capital enough to purchase and refurbish one beaten-down home is much easier than it is with two or three. As the price of renovations rises, it can get harder and harder to stay liquid in advance of a sale. And some of the most profitable units to flip are going to be the ones that require the most extensive renovations. If you run out of cash because of a hiccup in your deal flow, you may be out of luck. 

Whether you buy a home from a foreclosure auction or by hunting down leads yourself, another big part of your job will be finding potentially profitable opportunities in the geographical market of your choice. Typically, running your business will run a lot smoother if you can make the time to visit prospects in person and get a feeling for the home as well as the neighborhood that it’s in. 


Landlords make their careers by operating rental units and leasing them out to members of the public. In some cases, landlords can also be veritable real estate investors in their own right, but their primary focus is to retain the value of and generate cash flows from their holdings. 

As a landlord, your challenges will be different than with other real estate career paths. Specifically, you’ll need to:

  • Price rental units according to what the market can support
  • Set and enforce leasing policies that protect your investments
  • Screen potential tenants to reduce risks
  • Develop and maintain relationships with renters
  • Coordinate with maintenance staff or contractors to address tenants’ issues 

The important thing to remember about being a landlord is that you’ll need to be good with people, and not just your tenants. 

If you choose to use a management company to handle maintenance or a contractor to make improvements to your properties, you’ll be their manager in a sense. When tenants reach out to you about their fizzled lightbulb or flooding toilet, it’ll be up to you to triage their concerns and direct the appropriate resources to them in a timely fashion. Keeping track of these costs is an ongoing issue, and building a strong working relationship with the people you hire will go a long way towards keeping things running smoothly. 

Your relationships with your renters are also a major element of being a landlord. You’ll need to develop a keen sense of people’s trustworthiness and ability to pay the rent that’s specified in their lease. And sometimes, you’ll have to make hard choices about which tenants are more trouble than they are worth. In the worst case, you’ll need to pursue legal actions like eviction to stem your losses, and it isn’t something that anyone will enjoy doing.

Overall, being a landlord is among the most stable and least demanding of the real estate career paths. Once you have your investments leased out and being reliably managed, your concerns will be about maintaining cash flow, managing your tax burden by claiming depreciation on your properties, and paying down debt. The more properties you own, the more time you’ll need to spend on each of these activities. 

As you gradually become less leveraged over time, you’ll have the chance but not the obligation to identify new investment opportunities. That might be purchasing a new property altogether, or it could be something more mundane like investing in improvements to your current holdings.    

HomeVestors® Franchisee

Being an independently owned and operated franchisee with HomeVestors® is one of the lower-friction real estate career paths; it’s perfect for beginners as well as seasoned real estate investors. As a HomeVestors franchisee, you’ll get the leverage you need to purchase distressed homes. Then, you’ll invest in making quality repairs, and when completed, you’ll have the opportunity to sell them at their newly augmented market value. 

Franchisees get the advantage of having access to:

  • Quality leads
  • Expert investor guidance
  • Training materials
  • Marketing resources
  • Ongoing marketing campaigns
  • Real estate valuation software
  • Significant lending resources

If you choose to be a HomeVestors® franchisee, you’ll use these resources to grow your business more rapidly than you could otherwise. Similarly, you’ll get insider experience by being in contact with a huge number of experienced investors in all corners of the real estate market. 

The workflow of a franchisee doesn’t cleanly fit into the other categories of real estate careers that I’ve discussed already. Unlike for non-franchised real estate investors, getting a stream of leads is easy through the We Buy Ugly Houses® national marketing campaign which benefits all franchisees. With the quality leads in hand, thanks to the ValueChekTM property valuation software, you’ll have a standardized measurement to use for all of your prospects, which will give you more bargaining power while also honing your intuition. 

Likewise, making large deals with a limited amount of starting capital is possible with the help of leverage available to franchisees. And throughout the process, investing mentors will be at your service, ready to advise you on important deal-flow details or market intelligence. In total, franchisees have the tools that they need to succeed, and there’s no other program quite like HomeVestors.

If being a HomeVestors franchisee sounds like it might be an interesting path to start or supercharge your real estate investing career, you should know that it’s fully within your reach today. A full-time franchise costs only $80,000, and all franchisees get an initial week-long training session to get them up to speed. If you’d prefer a part-time commitment, you can get an associate franchise for $32,000. As long as you’re intending to operate in one of the 47 states where franchises are offered, you’ll be off to a running start in your new real estate career path. 

If you’re ready to take the next step, request information about becoming a franchisee today.

Each franchise office is independently owned and operated.

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