The $0-$10K/Day Case Study: Day 188

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Day 188


Yesterday might have been a breakthrough for me.

I didn’t make a million dollars, win the lottery, or suddenly get everything in my hopes and dreams.

But, I did sell.

If you read the past few days of the case study, you’ll see that I’ve been pushing a lot of pitches recently to try and land more work.

Well, yesterday more work landed. And it landed in a really big way.

I’ve sold 5 projects now that are north of $30K total fee. One was cancelled during COVID. One happened about ~9 months ago, and another is the data project currently ongoing that sold ~6 weeks ago.

I sold the other two yesterday.

It was a good fucking day. Turns out writing really good and long proposals will move the needle.

At a high level, I now have three projects about to start now that will run for the next ~60 days. They are:

  • Data project: $35,000 remaining
  • Project Support: $37,500 remaining
  • Market Analysis: $45,000 remaining

All in, that’s $117,500 over the next 60 days. This should be more than enough to ensure that we can close on our real estate acquisition in December for the 49 units.

It’s not all gravy. Each one of these projects is, at minimum, 30 hours a week. I’m going to work 90 hours a week for the next two months. To put that into context: that means I will wake up to start working at 6am every day and will work straight until 10pm every night, without a break. Saturday and Sunday will be lighter with only 5 hours of work each day, each.

That’s not good for my health (physical and mental). It’s not good for my family or my relationship with my family. It’s not good for my little two month old baby, who needs me around.

I also will end up paying ~$60,000 in taxes on this money due to self-employed tax and a few other lovely peculars in the tax system.

But, I really need to do this. I have an opportunity now, if I put myself through absolute fucking shit, to make more than double the average American yearly salary….in only two months.

I’d be crazy not to do that.

The trick is I’m going to put that money into cashflowing assets that will pay us moderately passive income, instead of blowing it on a flashy car and needing to grind again to get through.

$10K a day by 30. $10K a day by 30 is the north star.

Yesterday there were 1,503 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 5 hours and 38 minutes from 10:06 am to 5:44am, with two baby feeding breaks at night, for a total recovery score of 50%. I was dog tired all day long, but energized once I heard about these jobs selling.


No major exercise, but I’ve started building in some daily stretching to start to feel better. I thinked that helped me feel better, but overall strain was still high at 17.3 on the Whoop.

Stress levels

Stress was probably 3/5: I’m feeling good.


Diet was pretty good actually. Oatmeal for breakfast, vegan curry for lunch, and then faro for dinner.

My Day Job

Well, this is now an interesting conversation. I’m making a shit ton of money over the next two months on these consulting engagements so I don’t really need the income from this job. I also really don’t need this company putting time on my calendar when I’m already expecting to be working 6am-10pm.

Even if it’s only 5 hours a week, which isn’t, that’s an added hour that pushes back things on my day to day. For example, if I have two more hours of work for the day job one day, I’m now working to midnight instead of 10pm.

I don’t have time for this. As a result, my best guess is that I quit here within the next two weeks or so. Let’s see!

Investment real estate

Nothing. Keep the cashflow coming.

CCIO: My business

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

Content website business

Nothing, just some text messages with my brother who is likely going to be involved with some writing for the content business.

Acquisition Entrepreneurship

I got another Axial deal sent my way in electronics recycling. That is actually something that seems more aligned with macro-trends (e.g: lots more tech “stuff”) but I don’t have the cash for a few years on this!

Side Consulting

Lots of stuff

Data Project

We had a couple of calls here. The client is interested in introducing some new Excel models into our day-to-day, so my job is going to build out a model(s) that allow us to do some nifty analytics. Overall, I think it’s going in the right direction here but I’m behind on what I should be done with at this point.

Presentation Project

Couple calls and some updates, but things should be good heree.e

Market Research

Nothing, waiting for a kickoff call.

Market Analysis

Scheduling a kickoff call

Project Support

Scheduling a kick off call

Sourcing new work

Please god, no more.

$10K/day website

Daily post


Dinner with my fiancee



Rescue Time Daily Screenshot

Day 1Day 188 Rescue Time
It felt way longer than this. I think that’s because I don’t have any breaks and I’m cranking 100% of the time. I might try to introduce a break tomorrow.

What I made today

Current Income  Streams

  • Job:  $170
  • Presentation project: $400
  • Data Project: $500
  • Market Research: $220
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $1,355

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

Content Business: $10.79

  • 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

$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 $1,355 spent $114, which means….

Made $1,241 (pre-tax)

My plan for tomorrow

Tomorrow is Wednesday and I have:

  • A couple follow up items to schedule kick off calls for new projects
  • Some follow up work on my data project (Excel)
  • Probably some writing myself on the content sites now that I have some time
  • an interview with the VC firm I mentioned the other day

1,502 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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