The $0-$10K/Day Case Study: Update 194

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Update 194


It’s been a long time since I’ve updated here. I am sorry for being way behind.

Actually, with that in mind, I’ve now adjusted the case study. You might notice the cover photos no longer say “Day.” They now say “Update” because I will try to update them each day, but in reality, it’s probably going to be in vain!

A lot has happened since the last “update.” In that update, I talked about how I had finally quit my job and was excited about the implications and ramifications of being my own man.

I still am really excited about those implications and ramifications. I’m just busy as shit!

My consulting business is better than it’s ever been. Earlier this year, I wrote about how I made a ton of money in my first year consulting. Since then, I’ve sold >$150K worth of consulting work within the next ~10 weeks. I am close to selling another project that will make it even higher.

That is fantastic, and as you’ll see in the numbers, makes a huge difference.

I also firmly believe that this only happened because my “back was against the wall.” If you remember, I needed to make $70K in ~3 months in order to close our 49 unit deal. I am convinced I only sold that much work because I needed to sell that much work.

That leads to the other update: our 49 unit deal.

We did a ~14 hour day trip to drive out to our properties and take a look at them ahead of the acquisition. The goal was to be there for the inspection.

What a shit show.

We were under the impression, across all of ou research, that these properties were in good shape. Hell, one of them was built only three years ago. The property manager was doing a ton of work to keep them in good shape, and we trust the PM. She manages our six unit for us.

Unfortunately, that wasn’t the case. The properties had plumbing issues, roof issues, and mold issues. In short, it looks like a lot of lipstick was put on the properties but that they have a huge need for some serious underlying work. Our inspector quoted $200K to fix everything.

TBD on that deal for now.

Yesterday there were 1,483 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 need to adjust the phases because the phases are different now!

Wake up & sleep:

Whoop had me at 6 hours and 58 minutes of sleep, going to get bed 10:41 and waking up at 6:34 with some baby feeding time in between there.

Tota recovery was 93%. The godsend here that is helping me out is the baby is now starting to consistently sleep in 5+ hour chunks. This needs to keep up


No workouts in forever. Too busy.

Shitty excuse, but I can’t help it for now.

Stress levels

Stress was probably 2/5, with 1 being the highest. Busy day.


Diet was okay. Oatmeal for breakfast, Indian for lunch, not hungry for dinner.


Investment real estate

You saw about the real estate above. It’s a bummer.

CCIO: My business

Nothing going on here. This is going to be a huge part of 2021.

Content website business

I have a huge content writing business now. My strategy is to build a ton of websites by throwing a ton of content on them (good content, not shit content) and then monetize them with ads.

I have one website that is my primary focus right now. This website is now a month old and has 56 articles on it and nearly 100,000 words. I have another ~20 websites that are now live and will get some content on them to start aging those sides.

But, my big site is not done yet. I’m shooting for ~3M words on it, which means that I’ll have ~500K-1M visitors per month on it. At ~$12 per 1,000 visitors, that means $6-$12K a month in passive income.

I’ll write an article shortly on my content website business process, but for now, I can say I’ve hired 8 people full time around the world to run this.

Acquisition Entrepreneurship

Nothing. Years down the road.

Side Consulting

I’m slammed.

Data Project

I had a couple of calls yesterday and need to do some excel workout today.

Market Analysis

Nothing here, but this project has been going well.

Project Support

Lots of time here, and tomorrow is going to be busier.

Sourcing new work

I put together the proposal for that added project I think I’ll sell.

$10K/day website

It’s been a while here, sorry!


Family time with my fiancee at night.



Rescue Time Daily Screenshot

Update 194 Rescue Time
Started before 6am, ended at roughly 8pm. The day was longer than the 14.5 hours too because that gap at 3pm was a phone call I was on.

What I made today

Current Income  Streams

  • Market Analysis: $634
  • Data Project: $1,000
  • Project Support: $1,275
  • Real Estate Cashflow (13 multi-family units): $65
  • Content sites: $0

Total:  $2,973

Planned income streams

  • My Business (CCIO)
  • Ads on $10K
  • Acquired businesses
  • Coaching
  • Acquired hotels
  • Dividend stocks (especially muni bonds)

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


Life Expenses: $100

  • Rent, utilities, Internet: $63.33
  • Phone Bill: $1.57
  • Health Insurance (COBRA): $19
  • 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

Content Business: $119

  • Bluehost for hosting (9 domains): $0.89
  • Bluehost for domain names(9 domains): $0.27
  • Ahrefs for keyword research: $3.00
  • Surfer SEO for content: $6.63
  • Full-time employees (seven writers, one VA to post articles): $109

$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 $2,973 spent $230, which means….

Made $2,743 (pre-tax)

My plan for tomorrow

Tomorrow is Tuesday and I have:

  • 3 calls, including a big one for the market research
  • Project support work
  • Market research work
  • Content business work

1,482 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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