The $0-$10K/Day Case Study: Update 196

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Update 196


It’s been a long time since I last wrote here. A really long time.

Today is November 30th and my last post was October 11th. So, call it a little under two months.

There will be a ton of updates across all different dimensions below, but it’s safe to say that this ~50 day period was the most impactful period I’ve had in my professional and personal career.

I’ve been busy as shit. Let me talk about being busy and the concept of hard work for a second.

One thing I feel pretty strongly about is that people mistakenly use the phrase “hard work.” It’s a phrase that gets thrown around a lot. Think about it: how many people say they don’t do “hard work.”

The problem is, “hard work” isn’t a fixed definition. Your definition of hard work could be very different than someone else’s. For example: someone who did “hard work” at a 9-5 is very different than someone who works in M&A at Goldman and works 9am-4am every single day.

The Goldman person clearly is working harder. However, if the 9-5 person doesn’t realize that there is another level of work (e.g: the “Goldman” level), the 9-5 person will struggle to reach their goals.

Personally, I’m sick of seeing people who work 9-5 complaining that they “work so hard” and should be entitled to the same level of financial rewards of someone who actually works hard. I think it’s frankly ridiculous.

That’s why I think we need to quantify what hard work is. Saying “85 hours a week” doesn’t really drive the point home because most people aren’t familiar with exactly the number of hours they work each week.

Instead, I say something along the lines of: “I woke up at 5am to get a head start on work and finished at 10pm.” That, my friends, is a 17 hour work day. Have 5 of those in a row and you are at 85 hours a week.

Tell me again, Mr/Mrs. 9-5, on how you work “so hard” when there are people out there working 5am-10pm?

This case study is raw. It’s emotional. It’s authentic. And it shows what it actually fucking takes to achieve your goals.

Yesterday there were 1,428 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

This will be fixed ASAP. The phases are totally different now.

Wake up & sleep:

I’ve been averaging not a lot of sleep recently. You could probably guess that based on soapbox speech up there regarding hard work.

My Whoop has shown sleep has hovered in the roughly 5 hour range per night. However, it feels like a lot less because I’m getting up a few times a night for the 5-month-old baby, making the 5 hours of sleep not very restful.


This is embarrassing because it’s been crap. I’m a big believer in the concept that you need to do everything right to succeed, and I haven’t been doing this section right. I haven’t exercised in months.

So, I will slowly start getting back on the exercise bike. I will also block out time on my calendar (just five-minute breaks here and there) where I will sit down and do some actual pushups and sit-ups.

Stress levels

Stress was probably 1/5, with 1 being the highest. This has been constant now for a few months.

I’ve been feeling not great, and have broken down and cried at least once. This isn’t easy. I chose it, and I want it, but it’s not easy.


This has been about average. Nothing crazy, nothing bad.

Investment real estate

So we backed out of the big deal we wanted to do. In the interim, we found another property and negotiated on it, but couldn’t come to terms on it.

Right now, we’re going to hold until we find something we like.

CCIO: My business

I’ve done a little prep work here, but again, not much. I’m mostly getting ready for a big push in 2021!

I need to get this business to ~$50K a month by the end of 2021. I think that’s super doable.

Content website business

This has been a fun project.

I have a full-time team of 12 right now that are working with me to get words written, edited, and published onto websites. I’ll write more about it eventually, but the strategy is to build up ~50 websites that just have a fuck ton of content in order to drive traffic. That traffic would then be monetized with ads.

The rule of thumb, if a website is more than a year old, is that a site with one million published words will receive roughly 100,000 monthly organic visitors.

We have ~800,000 words published thus far in the first two months of getting the team together. Now that we are up and running, our run-rate is ~800,000 words a month. If we hold true to benchmarks, about a year from now, we’ll have ~9M published words online, or roughly 9 sites that each receive 100K visitors a month.

1,000 visitors are worth $12. So, if we’re getting 900K visitors, the sites are making $10,800 and are worth ~30X that, or $324K.

This is a long play, and as you can see, is a very expensive play.

Worth it, if it pays off.

Acquisition Entrepreneurship

Nothing. Years down the road.

Side Consulting

This is where the majority of my work has been. As you’ll see down below in the numbers, I’ve been fortunate to make ~$120K the past two months on consulting work.

It’s my best two months to date.

Data Project

This has been the “worst” project. I’m working for another consultant and consultants are horrible people to work with. I’m losing track of just the overall shittiness here regarding how things are coming along.

Fortunately, this project is just about done.

Market Analysis

This was/is fun. I have a little more to go, but this involves doing market analysis to see if it makes sense for one company to buy other companies.

This work is exciting, and it’s also very fulfilling. There is always a tangible answer “yes buy the company” or “no, don’t buy the company.”

Project Support

Another good protection. I’ve been helping the leadership of a well-known company rethink its entire strategy. The output of this work should come public over the next year or so.

Sourcing new work

I haven’t really been sourcing new work since I cannot manage more work right now!

$10K/day website

Literally nothing. I’m sorry


My beautiful fiancee and I got married and I wouldn’t want it any other way! She’s the love of my life and the most amazing thing in the world.



Rescue Time Daily Screenshot

It’s been a while. I’ll start adding these in now that I’m back to working daily.

What I made today

Unlike normal, I’ll try to have this section encompass everything for the past two or so months.

Current Income  Streams

  • Consulting work: $116,608

Total:  $116,608

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)

This section is a bit weird since I’m sharing the topline of the last two months. I’ll get this back to normal shortly.

My plan for tomorrow

Tomorrow is Monday and I have some time back since things are lighter

1,427 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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