The $0-$10K/Day Case Study: Day 127

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Day 127


It’s a strategy shift kind of day.

I’ve had a lot of things running through my mind recently and the stress has absolutely been turned up to its max levels. I’m going to do my best to explain what’s been on my mind, why it was a problem, and the shift in strategy that I’ve decided on.

The debt thought process

As you can see in my daily income/expenses summary, I have a lot of daily expenses. In fact, my expenses have been five figures per month for the past year.

The reason why is I have debt on it’s last year of maturity. I’ve been paying it off, and have technically 5 months left of those payments.

It’s a dark cloud though over my day-to-day. It creates a significant pressure to keep selling work so I can pay this debt off.

That’s thought #1.

The tax thought process

Thought #2 is about the extremely large tax bill. As I somewhat ranted on day 108 of the case study, I learned that my tax bill would be more than 55% of my total income.

I still think that’s fucking absurd. I’m putting myself through stress buckets to build a business and I’m getting penalized more aggressively for trying to go my own path than taking a damn job.

But, either way, that means I have an extremely healthy check to write the government on tax day. With COVID, it looks like that tax bill is going to be due July at the earliest. As I talked about in yesterday’s case study, pushing it back to September would be awesome.

That’s thought #2.

Buying another investment property

There’s an investment property out there that has got a piece of brain. It’s a 24 unit property in the territory of the property manager that we like very much. However, it’s expensive.

I want to buy it ASAP. The sooner we own it, the sooner we can collect rent from it.

But, here’s the thing: that is a self-imposed deadline.

To be fair, self-imposed deadlines are just how I work. This entire case study is a self-imposed deadline, and there is a literal day counter that counts downs until 30 on literally every page.

How I’m feeling

I’ve been feeling like shit. I’ve been feeling weighed down and anchored. I feel trapped, like I need to keep grinding.

I feel like I’m in a situation that is outside of my control. I feel ridiculous for letting this get to me.

I’m jumpy because I have a ton of different projects going on. I can literally feel the stress squirt into my system as I jump between projects. My phone is pinging constantly from different freelancers I’ve hired to work for me.

That cause of that thought is the fact that I cannot do all three things this quarter. I cannot pay off all my debt, buy the property, and pay off the taxes. I have the money to do two of the three.

I could theoretically just buy the property,  pay off the taxes, and keep paying a monthly figure to pay off the debt.

However, the debt is already weighing on my mind. If I pay off the taxes and buy the property, I will have no money left in the bank. That means I’d be two or three non-sold projects away from ruin.

I don’t think that solution will work. Which, leads to the strategy shift.

How the strategy shift came to be

Yesterday was another crap day, with significant stress.

I mentioned it to my fiancee, and she called my ass out.

She, correctly, pointed out that I was causing the stress myself. She pointed out that it didn’t need to be like this.

She’s right. She pushed me, and she’s right.

I’ve said it before on this case study. Warren Buffet, the greatest guy to case study of them all, has said it.

There is nothing more important than having the right partner. She’s the right partner, and the love of my life.

Thanks for kicking my ass into gear.

The strategy shift

I want that apartment building, but it should also still be available six months from now.

So, I’m going down a different path.

I’m going to pay off my debt this month and next. I’m going to lose a huge chunk of my liquidity as a result.

I’m going to pay my tax bill in June. I’m going to lose even more liquidity.

But, then I’ll be done. My expense bill will fall by 80%. I won’t be trapped anymore. And I’ll have learned a very valuable lesson about getting into debt.

It will push back buying the building  I want by ~5 months. It’ll push back buying the next one I want by another 5 months.

But, I think that’s worth a clear head.

Thanks babe.

Here’s what my new forecast plan looks like.

Blue is forecast, orange is actual.

What I did yesterday to make $10K a day at 30

The current phase of the plan

I’m in Phase #1:  The Job & Side Hustle Phase.  You can read more about the phases and my plan to get to $10K/a day at 30 here.

Wake up & sleep:

I woke up at 8:02 am after going to bed at 11:58, for a total amount of sleep of 7 hours and 43 minutes.

My recovery was very low though, with total recovery being 34%. This is a similar take away to yesterday, where I slept more than enough on the hour’s basis but my recovery was crap, largely driven by stress.

But, stress no more!


Exercise didn’t happen today. I had a strain score of 11.1 out of 21 due to a stressful day.

Once we move, I’m buying a Peloton.

Stress levels

I was at a 1/5, with 1 being the highest.

I talked about this at length above. However, I’m in a much better spot now based on the thoughts/implications discussed. Things should be good to go now


Diet was coffee, spanikopita, and some pasta for dinner.. 3/5 with 1 being the best.

My Day Job

A few calls, but nothing crazy

Investment real estate

This was disappointing.

We received this email from our property manager. This is the property manager I’ve talked about before who isn’t doing a great job.

There is a ton wrong with this email.

First, a property manager is paid quite well to handle these kinds of issues. As you readers know, my fiancee and I work a shit ton of hours. We also live a couple hours away from this property. We aren’t in the best position to solve this issue

Secondly, what is the takeaway or implication from this note? Is the property manager just informing us? Are they asking for help? Are they asking us to approve an expense? Is the entire building about to flood?

As a result, my response was this:

We are extremely frustrated with this manager. Right now, we have 3 of 7 units occupied with paying tenants. Two tenants aren’t paying, and two units are vacant.

We have called or emailed the property managers weekly for months now to try and get them to hurry up. Every time we talk with them now, they talk about evictions that aren’t allowed so they cannot force the two non-paying tenants to start paying. They also talk about how COVID is preventing them from renting the two vacant units.

That’s fair, but it’s also a bullshit excuse. The reason why is the property managers have been running this building since early January. Thye would not be stymied by COVID preventing leasing up the units or evicting past tenants if they had gotten the building rented in the first three months.

So, I spoke with them on the phone. I can’t unload on them, because they’ll shut down. Instead, I floated a balloon and asked how we could cancel service. They didn’t even seem to care.

We also can’t fire them, because the area doesn’t have any other good backup property managers

A few lessons here for us on real estate investing:

  • Interview, vet, and then interview again property managers before you buy property
  • Only buy in areas that have multiple, good back-up options

Here’s another big takeaway too: succeeding in business is about good customer service.  A new upstart property management company in that area can absolutely put our current company out of business in 30 seconds or less by delivering good customer service.

Absolutely nuts.

We’re talking with the team on Friday. I hope to see progress by then!

My Actual Business

I read a good article from Backlinko where Brian Dean mentioned his team uses this web app Notion to do a lot of work.

It looks nifty as hell, and is only $8/month per user.

I folded that into my plan for my business. I anticipate hiring 1, and then scaling to 9, different employees or contractors in the first year. As a result, I’ll need a tool like this for record-keeping, task management, and communication.

Side Consulting

I have a few projects going on now.

Business plan

I did roughly 30 minutes on this and will do more today.

Private Equity

So I heard back from them and they aren’t happy with the direction of my report. This was a substantial addition to my stress levels yesterday. They think my market report doesn’t accurately capture the market, which is the first I’ve ever heard that in my career.

The root of the problem is two-fold:

  1. This is an extremely niche market with ~1-3 companies in it. Correspondingly, there isn’t a lot of great data out there
  2. The private equity company already owns one of the companies in the market but asked me to build a market  report anyways to understand the market

With it being niche, I’m basing a lot of this on only one or two sources. With them already owning the company, and the company wanting to look as good as possible, they are arguing every point I raise.

I don’t blame them after all. If a consultant was saying they can only do  $1M in revenue and they believe they can do $1.5M, of course they’ll argue! However, this doesn’t happen when the private equity firm doesn’t already own the company.

I  did a few hours of work here to help address their concerns. I also want this to be the last bit of work we do/don’t want any more follow-ups. So, I ended my note by saying that I have other work and clients and  I’m pushing there to finish up before the baby comes, so I don’t have a ton of capacity. The hope is that punctuates why I cannot continue to help.

Financial modeling

Nothing here


Nothing here

Real Estate

An old real estate client reached out and hired me for an hour phone call for advice.

Sourcing new work

I got pinged about a possible consulting gig that is right up my ally: a market scan. I’m talking with them tomorrow.

$10K/day website

Published the post


My fiancee kicked my butt today.


Planning the move!

Rescue Time Daily Screenshot

This  excludes a few hours I spent on the phone today

What I made today

Job: $170

Rental Income (13 units): $33

UpWork: $75

Consulting: $394

My Actual Business: $0

Affiliate: Not doing yet

WordPress Maintenance Site: Not doing yet

Dividend Income: Not doing yet

Micro-SAAS’s: Not doing yet, 

Hotels: Not doing yet

Total: $672

Today’s pro-rated amount of monthly & yearly expenses

Expenses: $250

Once I pay off my debt, I’ll break out expenses into a line by line as well.

Today’s Income (pre-tax)

Made  $422

My plan for tomorrow

Tomorrow I need to:

  • Sell that pitch  for the new private equity project
  • Wrap up the modeling work
  • Crush the business plan work
  • Lots of day job work


Let’s get after it today. I’m feeling fricken awesome now and way better now that there’s a plan forward out of the debt and I’ve given myself permission to be okay with not buying that  24 unit this quarter.

There are a  couple of things I learned today about investment property, but the thing that’s always on my mind is how amazing my fiancee is.

What I did yesterday to make $10K a day at 30

The current phase of the plan

Wake up & sleep:


Stress levels


My Day Job

Investment real estate

My Actual Business

Side Consulting

$10K/day website


Rescue Time Daily Screenshot

Today’s pro-rated amount of monthly & yearly expenses

Today’s Income (pre-tax)

My plan for tomorrow

Dean Woods

Dean Woods

Dean’s goal is to create $10,000/day in passive income through entrepreneurship. Too many people write “success porn” that skates over the struggles many face in entrepreneurship. His goal is to create something real that highlights the lack of sleep, disappointment from family, and setbacks you really face in entrepreneurship. The hope is that $10K a day swill inspire someone else out there to make their entrepreneurship dreams happen. Dean Woods is side hustling and working a full time job to kickstart his entrepreneurial path. Prior to this life, Dean was a management consultant. Dean graduated with honors from The Wharton School.

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