When and How to Hire Assistant(s)

[Nick Gray]

Hi, I'm a 26-year old real estate investor/agent from New Hampshire who has acquired 30 apartment units across 6 properties over the past ~18 months. To date, I have self-managed my properties while also managing a few properties of others, working as an investor's agent, looking for more deals for myself, and going on active duty orders with the NH Air National Guard every couple months for a couple weeks at a time. My short term goal is to keep expanding my personal real estate portfolio, meanwhile my mid to long term goal is to build a full service real estate company with real estate syndication, brokerage, and property management under one roof. 

I have been successful in taking on multiple roles to get my real estate business off the ground, but I think that I am at or near the tipping point at which I need the help of one or more assistants. Much of my daily time and energy is spent on tasks that are not commensurate with my skill level: apartment leasing, repair scheduling, tenant relations, accounts payable, packing mailers, supervising renovation work, brokerage showings, brokerage marketing brochures, etc. I know that at some point I need to hire help for these tasks such that I can focus on raising capital, vetting new deals, networking, and education, etc. 

My question is regarding when and how I should make one or more hires. I am hoping that someone who is farther along the business growth curve can explain how they went about scaling their help with their real estate holdings. Perhaps you can recommend particular hiring moves at a particular number of units or gross rental income. 

For example, at how many units or dollars of gross income, can a self-managing real estate business justify a full-time office employee/assistant? What tasks should you have that first hire work on? What kind of person should that hire be? Likewise, when should a second and third employee be added? How would you then divide responsibilities between multiple workers? What is the appropriate compensation package for this kind of hire?

My focus right now is on an office assistant because I anticipate that person could help me with property management, brokerage, and investor direct mail marketing. I'm fairly confident that I can now give an assistant 40 hrs/week of work between those different roles, assuming the person who I hire can handle all those different functions. Placing a full-time employee on payroll does give me some heartburn though, so I want to be sure before I pull the trigger. 

A little farther on the horizon, I anticipate that I will need a handyman on the payroll such that I can address small repairs in a timely manner without lots of scheduling hassle. Right now, I can find contractors to renovate entire apartments, but I can't find someone who wants to fix a door hinge. At how many units or dollars of gross income can a real estate business support a part-time and then a full-time handyman? What minimum skills should that handyman have and what tasks should I continue to pay for on a 1099 basis? How much should a salaried handyman be paid? 

I would appreciate any suggestions on what hiring moves I should make now and in the future as I continue to grow. To give a sense of what money I now have available for payroll, counting only my apartment income, my current gross revenue is ~$42K/month and my net cash flow is ~$14K/month. Thank you in advance for all of your help.