The $0-$10K/Day Case Study: Update 199

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Day 199


What an interesting past ~48 hours.

The market-dominating news has been all about who is dominating the markets: Redditors with Robinhood accounts who’ve propped up stocks like Gamestop and AMC at the expense of hedge funds like Melvin Capital.

There’s all sorts of interesting implications and plenty of people are drawing sides: Mark Cuban, for example, tweeted how he thought the Hedge Funds have been front-running the market for years and are getting what they deserve as a result.

That argument, for lack of a better word, skews towards your thoughts on income inequality/the rich and I’m not the one to comment on that sort of implication. You can also guess, since this entire site is a case study about me working to become rich, how I feel about that.

Instead, I wanted to write a brief take that I haven’t seen anyone else write. So, worth it to discuss.

Here’s the take.

Without a doubt, the Redditors have won. They’ve caused billions in losses. It’s a classic case of many without power beat the few with power due to the sheer volume of the many.

Every uprising in history follows this exact pattern. The french revolution, for example, is a a proxy where the many beat the few due to power in numbers.

But, look at history. The few with power always right the ship.

I would bet everything I have on the hedge funds getting back into control. I know a ton of people who work in hedge funds. I almost worked at Citadel back in the day (they’re linked with Melvin). The candid reality is that the people at hedge funds are smarter and have significantly better resources than someone with a Robinhood account.

Reddit & Robinhood users won this battle, but they will crushed in the war. Just as history shows us how the ‘many’ always get beaten back by the few.

What are the implications? Well, if you own Gamestop, sell that shit. You made money, and a lot of it. But, it’s not going to last. Take your winnings and run.

Yesterday there were 1,369 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 re-write this article since my phases are different.

Wake up & sleep

On the Oura, I got a 71 sleep score with total sleep time of 6 hours and 13 minutes, resting heart rate of 54 BPM. Asleep 11:02-7:06am. The sleep wasn’t great because our little guy decided to cry between 1:50-3am and we weren’t able to get him back down asleep.


Very nominal exercise here, and will probably stay that way for a while. I saw a doctor yesterday and I’ve hurt my foot so cannot put a ton of pressure on it for the foreseeable future. As you can imagine, that limits my exercise potential!

Oura had an activity score of 84 with 424 active calorie burn.

Stress levels

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

Pretty low stress day because I’m not working for clients. I’m working for myself to start my business.


Yesterday was OK. I had Indian food for lunch and dinner. Overall OK.

Investment real estate

There’s a townhome that could potentially be rented. We think we have the cash to do this deal, but it’s going to be close. We might put an offer in tomorrow.

I emailed our accountant to see if he can chat to help estimate our tax bill. If the bill is larger than expected, the deal will be tight. If smaller, then we can absolutely make this deal work. It will be a slam dunker.

CCIO: My business

I am extremely confident in this business. The interviews were a huge success.


Today was three different interviews with my freelance competition and one interview with a customer of my company competition.

I think this business is going to really work. The reason why is one of the freelancers I spoke too has been in the industry for 22 years. She gave me a ton of information that basically confirmed my hypothesis about the industry are correct. In fact, she confirmed for me that business could really work.

She’s make >$200K a year doing the exact same thing I want to do as a freelancer. With a systemized business and process built around it, I bet I can do the same.

Goal is to get to 100 customers by my birthday on 10/28.

Content website business

I’ve slowed down here. I have a dozen sites out there just aging and get older and older. I’ll try to have their content ranking eventually, but for now, let’s just let these sites sit.

Acquisition Entrepreneurship

Nothing. Years down the road.

Side Consulting

Two projects at the moment.

Market Analysis

Lots of research here on specific industries. Goal is to understand if this industry is growing. Based on all indicators, it is. Think the client is going to be interested here.

Project support

So I took a quick thing, probably 10-20 hours a week, helping to support another consultant. It’s probably a few grand of revenue per week so worth it to help finance things.

Sourcing new work


$10K/day website

Daily post.


Spent time playing with the little guy and my mom came over.


Went to see the doctor so lost a few hours in the morning.

Rescue Time Daily Screenshot

What I made yesterday

Current Income  Streams

  • Consulting work: $731.80

Total:  $731.80

Planned income streams

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

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


Life Expenses: $80.73

  • Rent, utilities, Internet: $63.33
  • Phone Bill (iPhone): $1.57
  • Ladder Life Insurance: $0.83
  • Car (2018 Audi Q5): $15

CCIO’s Expenses: $2.53

  • G Suite accounts (2x; one for cold outreach, one for everything else): $0.40
  • Lemlist for cold outreach: $1.97
  • Bluehost domain name: $0.16

Health Expenses: $3.20

  • Peloton: $3.20

Productivity Expenses: $2.05

  • SuperHuman (to save time on email): $1.00
  • Rescue Time (to keep me honest on my productivity): $0.20
  • Evernote (to track everything): $0.27
  • Grammarly (to keep my emails looking okay0: $0.38
  • BackBlaze (to keep my files backed up): $0.20

Consulting Business Expenses: $6.10

  • Quickbooks (to track expenses): $0.40
  • G Suite email (for email): $0.20
  • Hiscox business insurance (for liability): $4
  • Gusto (to pay myself): $1.50

Content Business: $6.13

  • 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: $1.97

$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)

I made $731.80 and spent $102.85 with a bottom line of:

$628.95 daily earnings (pre-tax)

My plan for tomorrow

Tomorrow is Thursday and I have to make client update decks for the market research project (we’re meeting on Friday). Probably limited CCIO work today

1,368 days until I turn $30. I’m making $10K a day 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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