The $0-$10K/Day Case Study: Day 185

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Day 185


In yesterday’s post, I talked about how I feel like I’m on a razor’s edge in order to pull off the ideal Q4 of 2020.

The ideal Q4 for us is the successful acquisition of the 49 units we have under contract. It’s extremely exciting because it means a principal paydown of ~$5,000 per month and a cashflow of ~$5,000 per month too. You can’t really beat those numbers.

However, it will require just about 100% of our cash we have today (~3 months out) and then another ~$70K in order to pull this deal off. That stress was the focus of yesterday. I needed to find a way to plug a $70K gap.

Well, I might actually have done that. I have 3 long term projects all in the hopper right now, any of which would be enough to plug the gap. I just need to land one of them and we should be golden. For that reason, I spent a lot of time yesterday writing proposals. Normally, my proposals are pretty short but that’s “good enough” to land the project. This time, it needs to be better than “good enough.”

Either way though, safety in numbers. I’m feeling more confident today that we’ll have enough to close this deal in December of 2020.

So, let’s look ahead to December of 2021.

In December of 2021, I project our average monthly income to be north of $50,000 per month.

We should have $15,000 post-tax from both of our jobs and $6,000 from our real estate at that time. That leaves a gap of at least $29K that needs to be made up.

I could try to do consulting and absolutely kill myself to do that. However, consulting has historically been ~$20K a month the last few months. It will, somewhat, plug the gap but not all the way.

This is why I need to launch a business, CCIO, so I can have a scalable way to get to that point. I’m fixating on this because it’s the only way to make these numbers work.

If you notice, I’m focusing on how to reach revenue goals more than a year out from today. That’s why I’ll hit them.

Yesterday there were 1,508 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 slept 6 hours and 23 minutes from 10:23m to 6:27am for a total recovery score of 92%. I don’t know why the recovery score was so good, but I feel pretty great about it being as high as it is.


Again, I had no workout at all. Day strain was still pretty high though at 15.7 for some reason.

I might be missing the pattern in this whoop data, but it certainly doesn’t make intuitive sense to me that the data is saying high strain without a workout.

Stress levels

Stress was probably a 2/5, with 1 being the highest. It was a really busy day with an absolute ton of work


I had oatmeal for breakfast, coffee, chicken over rice for lunch, and then Wingstop for dinner.

That was really bad

My Day Job

I did a few things here to make it seem like I was doing work. Total, it took maybe ~15min.

It was annoying though to have to pretend to do work here.

Investment real estate

My fiancee is, very kindly, taking over a lot of the heavy lifting here. She is now coordinating with property managers, managing numbers, and the like. It’s extremely appreciated because man am I busy! I really don’t have the time to manage this.

CCIO: My business

TBD on this for now. It’s coming in Q1 of 2021

Content website business

Nothing here.

Side Consulting

Talk about a shitload of pitches.

Data Project

I didn’t do anything here.

Presentation Project

I had two calls with the client, and then a fair amount of work on actually making the presentations.

Sourcing new work

So I had ~4 pitch calls here.

I now have three pitches out for projects worth >$50K. I need one of these to land, and I think that’s likely


$10K/day website

Daily post


Family time watching the NFL season kickoff together!



Rescue Time Daily Screenshot

Day 185 Rescue Time
The day actually was a lot worse but looks okay because my phone calls aren’t logged heree.

What I made today

Current Income  Streams

  • Job:  $170
  • Presentation project: $400
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $635

Planned income streams

  • My Business (CCIO)
  • Ads on $10K
  • Content sites
  • Acquired businesses
  • Coaching

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


Life Expenses: $89.73

  • Rent, utilities, Internet: $63.33
  • Phone Bill: $1.57
  • Health 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 $635 spent $103, which means….

Made $532 (pre-tax)

My plan for tomorrow

Tomorrow is Friday, and I have to:

  • Two calls for work
  • Three calls for one for my data client
  • Two pitches to write and submit
  • Powerpoint work

1,507 days until I turn $30. I’m making $10K a day passively by then

Dean Woods

Dean Woods

Dean has started multiple businesses, with two successes to date. Outside of starting businesses, Dean & his wife buy multifamily real estate and will soon start buying businesses. This case study is meant to cover the daily struggles it actually takes to be an entrepreneur & serve as a giant middle finger to the 'gurus' in rented Lamborghinis. Dean is an Alum of Boston Consulting Group and The Wharton School. He and his wife live in Chicago with their children

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