The $0-$10K/Day Case Study: Update 198

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Day 198


Things are good.

Yesterday was a laid back day and a learning day. I think the business I’m starting, CCIO, is going to be super straightforward and profitable. However, that doesn’t mean I can’t learn a ton.

I started off yesterday with conducting expert interviews in order to learn more about my competition. I found a bunch of people on UpWork and am paying them for an hour to talk about their business and how they get customers.

They’re literally giving me their playbook for ~$30 an hour.

I’ve done these interviews a ton for consulting clients, both at BCG and my own consulting clients. The trick to these interviews is to be flexible.

For example, I ask a question like: “What does 5 star service look like in this industry?”

That’s broad and allows the interviewee to take the answer where they want too. It’s imperative to know what the interviewee thinks is important. An example of a not-broad question that doesn’t get you this nuance would be something like “How many times do you email your client each week?”

By asking these broad questions, I’m literally learning from years of experience. Overall, it will cost me ~$400.

Worth it 1000X over.


Yesterday there were 1,370 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 83 sleep score with total sleep time of 7 hours and 49 minutes, resting heart rate of 59 BPM. Asleep 11:36-8:15am.


20 minutes on the Peloton yesterday doing a ride with Alex. Overall activity goal on Oura of 419 calories burned (not counted the ~400 on the Peloton)

Stress levels

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

Not much need for stress. Super confident in where we are going here.


Yesterday was OK. I had vegan curry for lunch and dinner. That healthier diet is probably why the sleep was better.

Investment real estate

Nothing here. Waiting on the agent to get back to us regarding the possible property rental tenants.

CCIO: My business

God, I am loving this business.


I talked about this above.

Most interesting insight is about payment. My business is B2B, and I assumed my customer would hire my company (despite the high expected price) due to the value.

However, I found out that a fair amount of my B2b customers pass along the fee to their customers as an “admin fee.”

That was super interesting…lets me charge more!

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

Slowed way down.

Market Analysis

Quick call yesterday with this client to align on what is in and out of scope for a specific market we’re looking at. I’ll do more here tomorrow.

Sourcing new work

Turned down another project yesterday.

$10K/day website

Daily post.


I was primary baby caregiver for the day.



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 Wednesday and I have a couple interviews scheduled. Let’s get after it

1,369 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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