Feel like I'm losing my mind. Seasoned, organized investors. HELP

28 Replies

Hey everyone,

I am just completely unorganized. My situation is stressful but I realize I am creating that stress mainly. I work 65+ hour weeks running a kitchen, so that is already stressful. I realized that I am looking at REI as my "out" from the food industry and this incredibly stressful job managing kitchens. Maybe that isn't healthy but I don't know how to reroute that thought process now.

I started with $20k on 11/2017 and as of 12/20/18 had accomplished one flip and obtained five rental properties (1 Quadplex, 3 Duplexes, 1 SFH). Much further along than I planned to be at this point already, but I have this voice just saying "we need to find more asap. We need to grow as quickly as possible." On top of that, I am just, as already stated, completely unorganized. I have an ok organization system as far as filing goes... but that's it. I have no decent method for tracking my communications with agents, the multiple analyses I may perform on different properties. It will be a sort of "Shoot... did I need to get back in touch with any of these people?" "Did I ever finish that analysis of that property? What conclusion did I come to?" Just incredibly scattered and that is causing a lot of stress.

Do any of you have some really successful, useful methods you use to organize communications, communication streams, thoughts, analyses, etc. to get everything straight and help keep your head MUCH less cluttered and unmanageable?  Anymore, when I sit down at my desk and computer before I even do anything, I am so overwhelmed because I have no idea where I even left off. Maybe I am looking in too many places for deals right now too.  But also when an agent presents me with a deal that could have some potential, I just feel overwhelmed even by that and kind of fall off the radar, whereas this time last year I was GO GO GO and chomping at the bit. Now I am chomping but then when the door opens I cower away from it.  Don't know.  Just wasn't sure if anyone else had run into any of this themselves.  I'm clearly overwhelming myself... just trying to figure out how best to organize my thoughts and such so my head can be more clear I guess.

Sorry for the rambling nature of this. Just trying to get my thoughts out so maybe I can grab some advice, especially on the organization piece.  

Thank you!

@Brian H. from one disorganized person to another, I know a guy (ie CEO) who simply uses a yellow pad to write everything down in one place (ie an "external hard-drive") on a variety of subjects/topics/brainstorm/etc. Have you thought about using a yellow pad or notebook and simply writing everything down in one place? There may be other fancier digital ways but at least you can comb through the yellow pad/notebook and find everything (notes, conversations, etc)? By example, when you have a new deal, flip the yellow pad to a new page and write the property address at the top then use that page to write all your notes, listing agent, contact info, if you complete the analysis write it down and put a check mark by it, etc. Once in escrow, write In escrow, etc. Got another deal? Flip the page and start writing. Conceptually this will give you one central place to write/source all of your info-whatever you do just don't lose your yellow pad/notebook 😉  

I make folders in my email and name them for each property and file all correspondence in the appropriate folder.  

If you are often working in front of your computer, you can do the same with each property you look at, start with a standard check list and then add comments below that and write 'done' next to each item on the check list as you complete it.  Again name the file based on the address of the property.

On the other hand, if you work better away from your computer, do the same thing in a notebook.  Divide the notebook into sections for each property allowing you to work on multiple ones at the same time.  You will still need to file your emails, but it will make it easier if you have them in individual folders.  Should your agent send you an email about 2 properties, forward it to yourself and put the original in one folder and the forwarded message in the other property's folder.

Most importantly, take a deep breath and a few hours to get organized.  Organizing can create a bigger mess at first, but in the end it is worth it.

@Brian H. I really like @Brian Gerlach 's answer.  I used to use a composition but like this one https://smile.amazon.com/Mead-Composition-Notebook-College-Sheets/dp/B000GP16R0/ref=sr_1_36?keywords=notebook+bound&qid=1554470789&s=gateway&sr=8-36 from Amazon.  That way you don't "lose" anything.

This is a great start and doesn't have to ever end, but you'll find it is best for some uses and not for others.  You'll need multiple systems and it takes time to get them into place.  Here are the systems I use:

Podio for keeping track of seller leads.  You can use it for many other things to and have it remind you to follow up on things.  You can take notes, add to notes, go back and read the progression of notes, etc.

Dropbox.  I have so much stuff in dropbox.  Every unit has a folder.  I keep leases, property docs, all sort of things nicely organized here and can get to it from anywhere.  I do keep notes in here but it is not best for that.  Dropbox has a great scan feature (I used to use a different app for that), that allows you to immediately scan and upload docs.

Evernote.  I use this to keep track of various notes.  It has a different use than Podio, which is more of a CRM database.  This is just notes.  But each note for me is like a never ending sheet of paper that I can just keep adding to as needed., as opposed to a physical notebook that would get messy after awhile.  Organize the notes and notebook to fit your needs.

Vumber.  This isn't really for notes, but does help me keep organized.  It is a paid service, you can have multiple numbers and use different numbers for different purposes.  Rentals, Leads, whatever.  Plus you can text using those numbers.  I have a couple of special numbers for rentals and I know if I have a communication on that number that it is about certain rentals.  I can go back and read the trail of texts and remember where I was.  You can have some numbers forwarded to your real phone and others go right to voicemail.  You can also use Google Voice (which I do) but you can only use it with one number for outgoing calls on your phone.

Gmail.  You probably already use this.  Google has an unparalleled search feature and is great to go back and find a certain email.  Plus you can categorize things into "folders."

There are all sorts of to-do and task websites and apps, too, that will help keep you on track.

And the good old composition book.  But make sure you eventually you'll want to get any information you really don't want to ever lose into one of these other systems.

I'm probably leaving a couple of things off here, but hey, I'm disorganized too!

@Brian H. ,

I tend to be fairly organized.  Here's what I do:

  • I have a spreadsheet that lists financial summaries (revenue, expenses, taxes, ROI, etc) for each owned property and any we're evaluating. It takes 10-20 mins to enter the info for a new property, and we'll go back and refine the numbers as necessary, such as if the rehab budget/cost basis changes from our first estimate. If there's a number I'm not sure about, I highlight it yellow and come back to it later. Using this method, I can very easily see how the potential property stacks up against what we have.
  • To manage email, I use different email aliases for each property, for example [email protected]<domain>.com, which then goes directly to my main email client.  It's easily searchable inside the email client.  Once I needed more aliases than my email provider allows on a single account, I created another account and configured it to forward all email to my main account, which gave me 10 more aliases to use.  Another tip is to always add the property address or some other identifier in the Subject so you can search/filter on it.
  • To manage comms, if you find that your properties/tenants have a lot of 'stuff' going on at any one time, you just need a summary table or Action Tracker.  This could be a single spreadsheet/table that lists one property per row, then whatever columns you need: Owner Action, Tenant Action, Comms needed, or whatever else you need.  Update it daily, weekly, or as required.
  • To track monthly income & expenses for tax purposes, I use one spreadsheet per property per year.
  • If you're comfortable using cloud products, you could store these various docs there and have access from anywhere (e.g. OneDrive, Google Docs, or similar).  If you go with cloud storage, make sure you understand the security risks.
Originally posted by @Mark Fries :

@Brian H.

Quit the 65 hour kitchen job, go ALL-IN. Problem solved.

That's the dream, man. That's what this is all for.  But the issue with that, at this point, is there are two kids in the picture. My SO and I are also steamrolling our debt. We are putting almost $1800 towards our debt each month, but I REALLY want to be fully debt-free (not including business debt) before I think of leaving this job.  She is almost completely debt-free and then we will tackle all I have left, which is a measly $40k in student debt.  If it were just me, I would stop today and attack this head-on.  I have the drive and determination and I can live off much less but the kids change all that.  One is starting to drive as well. Soooo... haha  Plus, I need to build up my business' working capital a good bit more before I just jump in.  My current five rentals cashflow about $2000 per month, after all is said and done.  They killed the 1% rule. Came in almost 3%. Got REALLY lucky. Older couple just done with renting and trying to get rid of the properties quickly.  Was out bid by a bigger investor who flew in from DC but they liked me more and how I was doing things, so ended up selling to me anyways, which was mind-blowing.  

But anyways, I'd love to stop and jump all-in. I just don't have the resources at this time, is what it comes down to. Which is frustrating because I also need more capital to really jump into a lot of these awesome deals I keep finding and can't quite make happen. Meh.  

Originally posted by @Joe Villeneuve :

You need a partner.

I have a couple people with some expendable cash that would maybe be interested in making some money with me but they are also incredibly busy and work out of town (both on oil rigs), so lining up our times are incredibly difficult.  Otherwise, not sure how I go about finding a partner.

Originally posted by @Brian H. :
Originally posted by @Joe Villeneuve:

You need a partner.

I have a couple people with some expendable cash that would maybe be interested in making some money with me but they are also incredibly busy and work out of town (both on oil rigs), so lining up our times are incredibly difficult.  Otherwise, not sure how I go about finding a partner.

 You just found your partners.  Now just find the time to get together to talk.  This is the 21st century, and we are on a 24 hour clock.  Setting up meeting time with people can be hard, but if that's all that's holding you back,...(I'm biting my tongue right now_...

@Brian H.

I hope this doesn't sound negative or offensive because you seem like an extremely hard working guy who is also very intelligent... But you seem to have an answer or an excuse for all the feedback... Almost like you are dragging an anchor for no real reason other than just to drag it... You need to cut the rope on that anchor and work on freeing your mind, changing your thought processes....

@Joe Villeneuve

I hear ya.  Yes.  I will reach back out to them and see about getting more organized and on top of that piece of this.

@Mark Fries

No, you are right. My girlfriend even points out how negative I have become over the last maybe 4 - 5 months.  Granted, the heavy mental stress of running the kitchen (kitchen employees are a strange, rare, exhausting breed) really wears me down... but I was ok this time last year and cranking forward.  I have been doing yoga maybe 4 nights a week and trying to meditate more because (surprise!) it helps.  It's just the whole fitting-everything-into-my-day piece.  But that there is another excuse! haha  I am a hard worker... have my dual degree in math and stats, minor in finance... so I have the head for this stuff and the drive, as you said.  Just need to cut that anchor... 

It's funny. I had to stop and delete more excuses right here. Thank you for that. Hearing it from someone besides my girlfriend helped. I love her and respect her and hear her, but sometimes we need to hear it from an unattached party.

65hrs is not that much on work. It is hard work running a kitchen that I would agree.  You need to do a self-evaluation of your time logged and available hours each week.  From there you can break down areas to achieve more time.  Then you want to see what areas you can cut out.

For me.  

I cut out TV. No TV Shows( Don't even care about Game of Thrones), No sports.  Man, you have no idea how productive and how much time you will get just by cutting this thing out of your life. Why? It was simple. I wanted to achieve more and get more time. Real life success is more entertaining than TV. The TV does not pay the bills but the action in real life does. 

This may not solve your organization skills but will free up time. 

Originally posted by @Mark Fries :

@Brian H.

I hope this doesn't sound negative or offensive because you seem like an extremely hard working guy who is also very intelligent... But you seem to have an answer or an excuse for all the feedback... Almost like you are dragging an anchor for no real reason other than just to drag it... You need to cut the rope on that anchor and work on freeing your mind, changing your thought processes....

 Thanks Mark.  I can "stop biting my tongue" now.  (See my post above)

@Dennis M.

Heard that.  I will check them out.  Will make a point to better utilize my time away from the restaurant.

@Frank Wong

It's not the hours that is as much of a burden as the mental end of managing kitchen employees. I've work kitchens for years, used to push 100 hour weeks at an old job at certain times of the year.  Just can be really hard to focus and organize my thoughts after a 12 hour day dealing with the kitchen.

I will definitely do a self-evaluation of my free time. I think that would help. I can do it on my whiteboard to make it more visual for myself...  maybe even, at least for now, schedule what I do in my "free" time as well. 

Thank you guys.

@Brit F.

Thank you for the information.  I am a bit lost on the comms part.  The action tracker? I'm not really getting what you are doing there.

@Brian H. , it's just a structured To Do list...something that lists your different properties, agents, or other workstreams.  Then, then you write down the next thing you need to do, or what you're waiting on from them.  The purpose is to help consolidate your on-going property-related tasks in one view.  For example:


123 Anywhere street: Waiting on Agent to pull comps

456 nowhere, unit 110: Property manager following up on late payment.  Call back on Apr 7

789 Somewhere: Sales contract pending.  Need to locate survey.


I'm trying to think of an analogy to how you would manage a kitchen, but I've never done that :)  Do you have a method of managing kitchen operations that you can carry over to real-estate?

Buildium is worth the money. e-leases. online applications. online payments. accounting software. maintenance/work order system.

I also love google keep for to-do listing.

@Brian H.

I am just starting out and feeling a lot of the same things you are experiencing (mainly the pressure to get out of a career that robs a lot of my time I would rather spend investing). I have been listening to several podcasts lately, but one in particular has been really motivating. 

It opened my eyes to the fact that even HIGHLY successful people have doubts, negative thoughts that creep in and things they are unsure about - the difference is -they do it anyway!! These people have taken control of their thoughts and actions and push forward, in turn creating confidence in what they are doing. 

Another point I am learning: there are no "real super secret shortcuts" its hard work and consistency over time that gets the results we are after (no matter where we are starting from). To me this was good to hear because I know I can put in the work. 

I have always had this misconception I wasn't going to be able to create wealth because I came from a very blue collar upbringing. I've always thought I was missing some BIG secret. 

What I know now, is by living well below your means (paying off debt as you are), working your butt off and investing you can literally change the trajectory of your life, it may take several years, but it will happen. 

It sounds like you have a ton of hustle, maybe finding some positive influence from books or podcast can help re-frame your though process. I bet the organization will help a ton as well. 

Best of luck!! 

@Brian H. you are expecting too much from yourself in too little time. I have two thoughts for you:

#1 - getting organized is a journey into your own mind and not something an app can fix over night. Developing systems that work for you is a process that takes time, because what systems work best for you depends very much on your personal preferences. If you never had a management job, it's like me asking you to teach me in an internet post how to run a kitchen. Maybe take a look at the grandmaster Peter F. Drucker - lot's of books on the subject, but "Managing Oneself" is a great start. And "The ONE Thing" written by my boss. You will be going through loops: reading about something new, trying to implement it, decide if you like it and then - change your habits accordingly. The last item is key and as you know chnaging personal habits takes time and energy.

#2 - focus. You are being opportunistic and all over the map with your investments. My recommendation is focus on one area, on one type of building, on one price range. This will improve your acquisition process ten X. If you specialize on 1960's ranches in a certain neighborhood, you will become quickly very familiar with the typical inventory, price range and condition. You will know within 10 seconds of looking at a listing if this is a deal or not. It will also reduce the stress level, allow you to make faster decisions and decide with much more confidence. If an agent sends you a 1920 three family from another part of town, you have to study comps, both for sale and for rent, you don't understand the type of building, it's materials and issues very well and you have no time to learn all that, because the deal will be gone tomorrow. That induces a ton of stress of course. Focus and clarity reduces stress.

Good luck!