Strategies to streamline a quickly growing portfolio

[David B.]

Hello Everyone! 

I have officially been investing in real estate for the last year, and in that time I went from owning one condo to now owning 5 duplexes. I am also about to close on a portfolio of three more duplexes, making my total 8. For the most part, all of these have been done by using the BRRRR method. Lastly, I am also flipping houses (4 this year)

I feel generally good about the portfolio being built -- virtually every property cashflows at least 15% COC (some much higher) and have much higher IRR'S. A couple of them only break even after the refi, but my plan is to hold until I can get a better rate (which I don't think will be hard given that I'm currently at 8.5 mostly) and then refinance all of them as a portfolio that cash flows very nicely.

The flips I am averaging about 40 - 50% returns. Which I'm thrilled about. I had a couple contractor issues early on, but things are currently getting smoother. 

As you can imagine, my workload has increased as well as my monthly payments to the bank. I have plenty of reserves for a rainy day (I'm not worried about default), but I do find myself stressed with managing the payments and also the flips as it relates to tracking expenses and reimbursements for the hard money. 

For context, I am not someone who traditionally organizes well. I'm highly ADHD, and while I'm always tracking the numbers, it's not unpredictable that I could lose something in the details. What I am is goal driven, smart, singularly focused, and a great communicator of my vision. But I could use some back up... 

I'm wondering who and what I could employ to help streamline my systems as this business grows. I have considered hiring a bookie to track all transactions as well as an admin assistant to split up the workload. In the future, I imagine taking property management in house as well. I currently have one managing the properties but i have to say... not impressed. I had to call them out on almost 4000k dollars that they had neglected to pay me over the last six months. Seems they had an "accounting" error. 

Then of course, there's the idea that I could also be sourcing deals on my own with a team that was calling on our behalf. That seems a little far fetched at the moment but the wheels are turning for the future. 

So to summarize, as I continue to Flip and Brrrr, what could I be doing to grow a team and organize this... thing... that i'm building? When would you hire someone, and in what order would you begin hiring? I can tell you that the bookie feels like the most important element to start. But I'm not sure where to get one or what that should reasonably cost. 

Honestly, even if you don't have a team but you've built something similar to this.... how did you organize everything? What sort of strategies did you employ as you grew? My greatest fear is somehow screwing something up that would stop me from paying the monthly debt service on my portfolio. This its slightly irrational, as the numbers support debt service. But still - as the number of mortgages grow so does the fear that SOMETHING could happen. I'm sure some of you can relate. 

Im a rookie so I'm sorry if this feels amateur. But would really appreciate any insight other investors have garnered as they built their portfolios. I can tell you that my goal is to own 50 residential properties. Whether it takes 5 to 10 years, that feels like a really powerful but achievable number to me. 

Thanks for reading. Best, 

DC