The $0-$10K/Day Case Study: Day 179

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Day 179


I have a very detailed, month-by-month financial model that predicts out our money. It forecasts how much we make on a monthly basis for the next ~10 years, how much we spend, how much we have left over, how much we invest in real estate, etc.

I live and die by this model. I spent significant time each day in it.

Overall, the model is close. The numbers are close.

We need almost exactly $70,000 more than what we have today to close on our real estate investment deal at the end of the year. That’s a lot of cash. We will make about $70,000, but will spend about ~$20,000 on fixed expenses like rent and car payments and all of that fun jazz.

So, I really just need to find a way to make ~$20,000 on the side over the next 4 months to close. Of course, that will leave us with essentially nothing so that isn’t the greatest to say the least! Optimally I make a lot more than that.

But, I’m stressed as hell.

If I look at the model, it’s existed now for 17 months. That means there has been 17 months where I’ve projected an income.

I’ve exceeded that projection 17 out of 17 times. In aggregate, I’ve exceeded my projected income for the past 17 months by more than $100K.

So, I should be “confident” that I will hit the numbers I hit in order to close on the property we want. In practice, I should be extremely confident of that fact actually.

I’m still nervous about it. I’m stressed about it. I have a number to hit and that’s stressful. That’s difficult, that’s intimidating. I don’t really like this feeling.

I feel like my back is against the wall. I feel like I need to break out all the stops to try and make this work. I feel like I need to push and pry and shove to get things going in the right direction.

My hope is I feel better once this deal closes. In reality, I know myself well enough to know that I might not feel that way. I’ll probably feel like things are tight and that I need to work more to accumulate more cash.

Honestly, taking a break would be nice. But, we literally cannot afford to have me take a break. So, I’m not going to.

Back to the drawing board.

Yesterday there were 1,518 days until I turn 30 and need to make $10K a day passively. Here’s how I spent it in pursuit of that goal

The current phase of the plan

I’m in Phase #3:  The Business Phase.  You can read more about the phases and my plan to get to $10K/a day at 30 here.

I still consult, and I still have a job. I’m looking forward to removing both of those ASAP.

Wake up & sleep:

I fixed Whoop here so I’m starting to get some sleep data again. I’ll have the data to report out tomorrow.


I did some arms, abs, and pushups yesterday. It wasn’t much, but it was something and I’ll count it as that.

Stress levels

Call it 2/5 on the stress, with 5 being the highest.

I’m getting stressed again just looking at these numbers. Again, we’re ahead of schedule. There’s no reason not to be extremely comfortable with how things are.

I’m still nervous and stressed about it. I don’t particularly love this sensation.


Vegan stuff, including lots of dairy-free ice cream. The Vegan part is good, the ice cream part is bad. I want to get abs!

My Day Job

I had a couple calls yesterday.

Honestly, they aren’t using me and my skillset right so that’s a huge pain in the butt. It’s

Investment real estate

Limited action over here on our part, which is how it should be. This should be “mailbox money” where we don’t do anything but cash shows up each month in our bank account.

Tomorrow we find out what the scoop is with our roof.

CCIO: My business

TBD on this now!

Side Consulting

Still not a ton. I think I could and maybe should be doing more work here.

Data Project

Not much.

Sourcing new work

I pitched on a dozen or more pieces of work to try and get something to land. I’m optimistic that something interesting will come down the pipeline here.

$10K/day website

Daily post. I also added a ton of other pieces of content I’ve written elsewhere online to $10K to help consolidate and grow things here.

$10K is a long, slow grind. I know this website will take ~3-5 years to really, truly grow. I’m writing this sentence right now knowing that no one will read it for years.

But, that doesn’t mean I shouldn’t be writing this sentence. I should be, because the investment of time today will pay off in dividends down the line.


Time with the baby and fiancee.


The biggest thing going on here is our overall finances. We are looking to “level up” into a new world of advisors who are going to assist us with the next progression.

To that end, we’ve started finding and interviewing total accounting and legal pros who are going to bring things up to the next level for us. We spent time yesterday doing this with accoutants.

I’ve worked with an accountant in the past to do my taxes, and he was fine. I’m sure he did my taxes correctly.

However, we’re not looking for someone to just do things “correctly.” We are looking for a true partner and thought leader who can give us advice about the things we should be thinking about and doing. For example, should we do a cost segregation study on our properties? Should we not? Why?

What are the unknown unknowns we should be thinking about?

So, we talked with a couple of different accountants who specialize in high net worth clients in Chicago. Just getting them on the phone was a challenge as I needed to position us as young and very likely to reach that high net worth barrier that it’s worth their time to invest in us upfront. I’ve done this before with bankers and others, and it’s extremely valuable.

Once we got them on the phone, some were interesting, some weren’t.

We really liked the guy we spoke to yesterday though.

What he did, that others didn’t, was ask questions.

He started off the call by asking maybe 20+ questions in a row. They weren’t random questions as well; they were clear and absolutely leading to something.

Then, he told us what he would recommend we do and how to do it.

That’s the kind of shit we want to see. Someone who invests the time upfront to learn, then starts providing advice.

We love to see it. We hired him

Time to level up our accounting game.

Rescue Time Daily Screenshot

What I made today

Current Income  Streams

  • Job:  $170
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $235

Planned income streams

  • My Business (CCIO)
  • Content sites
  • Acquired businesses

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


Life Expenses: $89.73

  • Rent, utilities, Internet: $63.33
  • Phone Bill: $1.57
  • Heath Insurance: $8.90
  • Ladder Life Insurance: $0.83
  • TrueBill for Budget tracking: $0.10
  • Car: $15

My Startup’s Expenses: $0.16

  • Bluehost Domain name: $0.16

Health Expenses: $4.20

  • Peloton: $3.20
  • Whoop fitness tracker: $1.00

Productivity Expenses: $2.25

  • SuperHuman to save time on email: $1.00
  • Rescue Time to keep me honest on my productivity: $0.20
  • Fantastical as my main calendar: $0.20
  • Evernote to track everything: $0.27
  • Grammarly to keep my emails looking okay: $0.38
  • BackBlaze to keep my files backed up: $0.20

Consulting Business Expenses: $4.80

  • Quickbooks to track expenses: $0.40
  • Google Business Email Account: $0.40
  • Fiverr for virtual support: $0
  • Hiscox business insurance: $4

$10K a day: $1.59

  • Kinsta for hosting: $1.00
  • Bluehost for domain names: $0.03
  • WP Rocket for speed: $0.14
  • Link Whisper for SEO: $0.14
  • Elementor for site design: $0.14
  • Astra for theme: $0.14

Real Estate Investing: $0.52

  • Legal Zoom Registered Agent (all LLC’s): $0.52

Today’s Income (pre-tax)

Topline of $235 spent $103, which means….

Made $123 (pre-tax)

My plan for tomorrow

Tomorrow is Wednesday, and I have to:

  • Quick call with a client
  • Make a post on $10K
  • Pitch on new work
  • Do a quick write up for the potential new job I’m talking too

1,517 days until I turn $30. I’m making $10K a day passively by then

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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