The $0-$10K/Day Case Study: Day 184

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Day 184


It feels like I’m living on a razor’s edge. If I can “thread the needle” for the next ~6 months, probably 12, then it is mathematically inevitably I’ll get to $10K a day at 30.

But threading that needle is like walking on a tightrope high above the city. If something goes wrong, I could slip and fall and be left with nothing.

For example, we have that 49 unit deal that we really want to do and are currently under contract on. However, this deal is going to wipe us out entirely with literally nothing left from a finances perspective. That’s scary, because I need to make ~$50k over the next three months for us just to have enough to close the fucking thing.

Then, we’ll have nothing left. If we need to replace a roof, we can’t afford it. If we need cash for a personal emergency, we don’t have it. It’s really tight.

I am working a full-time job, but they are annoyed with me and want to meet on Friday. To be fair, I’m annoyed with them as yet another important member of the team up and left. I can’t really blame them. But, we need the money over the next few months.

I’m also investing (some, not much) into new business lines with my websites. That’s exciting, but it won’t show a return for at least a year, if not more. It’s an objectively stupid investment.

Finally, I need to get started with my business CCIO as soon as possible. Doing that would mean sacrificing time from other stuff, which isn’t great either.

In short, there are a lot of balls in the area, a lot of investments going on, and those investments are wiping us dry.

If all goes well, a year from now we could have real estate, a business, and a website business all generating us money. Or, we could be fucked and in such a big hole.

It’s so fucking precarious. This could go either way. I need to land a big project, or two, to help make this not go into the shitter.

I’m on edge, and probably will be for the next year.

Yesterday there were 1,509 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 7 hours and 5 minutes from 10:12om to 6:32am for a total recovery score of 52%. The sleep about was decent, but the recovery wasn’t, which means I’m stressed. Got to love it. Not surprised in the slightest.


Again, I had no workout at all. Didn’t even stretch or do abs or anything! My total day strain was lower here at 8.4.

Stress levels

Stress was probably a 2/5, with 1 being the highest. Consistently on edge here.

We have a little baby at home after all. That’s the epitome of stress for most people. He doesn’t love sleeping.


I had oatmeal for breakfast, coffee, and then chicken curry for dinner. Overall wasn’t bad, but it also wasn’t vegan.

Not great.

My Day Job

So yesterday I talked about how the talent is quitting the company left and right. I’m probably following as soon as there is some sort of backup plan in place.

However, I think they are annoyed with me or something. We have a “review conversation” on Friday, so we’ll see what happens with this job. I’m about sick of it. The leadership is a bunch of amateurs, and their pride is wounded since the talent is leaving. I feel like the conversation on Friday could be tough as a result.

Investment real estate

So I’ve talked in the past about how we’ve tried in sell our 7 unit property. We ended up pulling it off the market because we weren’t getting offers we loved.

Well, we just got an offer yesterday even though the property is off the market. It’s from this guy on BiggerPockets I found and kept close. He came in way low, and wrote a paper on why. He’s thinking about this a bit too academic, so we’re going to pass.

CCIO: My business

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

Content website business

I found a great freelancer who built me a website for $30. It was cheap because it was only an hour or two of his time because I gave him very instructions on what I was looking for.

This new website will now largely sit with limited content added for the next year or so to help “age” thee site.

Then, I’ll get after it!

Side Consulting

Same old same old.

Data Project

Couple emails here. They want to meet on Friday as well and don’t seem super thrilled either.

Are all of my clients/jobs mad at me?


Presentation Project

I built an outline here and had a call. Tomorrow is going to be really big.

Sourcing new work

I followed up with the big $75K pitch and they seemed pretty happy with how things are progressing. I’m working on a proposal for them now

$10K/day website

Daily post, and a post about how to actually make ten million dollars.


Family time, especially dinner together



Rescue Time Daily Screenshot

Day 184 Rescue Time
Standard day, full of a shit ton of work.

What I made today

Current Income  Streams

  • Job:  $170
  • Consulting for data project: $40
  • Presentation project: $400
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $675

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 $675 spent $103, which means….

Made $572 (pre-tax)

My plan for tomorrow

Tomorrow is Thursday, and I have to:

  • Crank on some presentation stuff for that client
  • Two pitch calls for new work
  • Several meetings for the day job
  • Work for day job
  • Website content business work (if possible)

1,508 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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