The $0-$10K/Day Case Study: Day 177

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When I worked at BCG, I worked for one of the top companies in the world. Thousands of people apply for a handful of spots each year. You graduate college and start working directly for CEOs. You make six figures easily, and the path to <$1M a year is 10 years and very straightforward.

It’s about the best start you could have to a career. I left to go join a startup in the hopes of starting my own one day.

Here’s a secret though: I would have sucked as an entrepreneur if  I started a company directly out of BCG.

Said plainly, I didn’t know what I didn’t know.

I had no clue how to sell something. I had no clue how to automate an outbound campaign. I had no clue how to build conversion metrics. I didn’t know what truly shitty leadership looked like so I could make sure to never be that kind of leader myself.

Fast forward a year, and it’s now time for me to leave this job. The plan has always been now to go work at launching my own company.

But, here’s the interesting thing: a job landed in my inbox. It’s for a venture capital firm specializing in real estate. Not only will regular readers know that real estate is very important to my fiancee and I, but, it’s also inspiring thoughts similar to my leave from BCG. Namely, I don’t know what I don’t know.

Is it worth me taking another job for another year?

The best-case scenario is that I take it for a year, learn a shit ton, make a decent salary, continue consulting on the side, and then leave to start my business.

The worst-case scenario is that I take it for a few months, absolutely hate it and don’t learn anything, quit, and then go start my business.

Either way, I still start the business within a year from today. I possibly start the business with another year of added knowledge.

I’m actually strongly considering it, and spend some time on the phone with recruiters yesterday.

Yesterday there were 1,524 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:

Average sleep. Whoop sucks


I did a 30-minute ‘Club Bangers’ Peloton ride and crushed it. I think I finished in the top ~3% of riders, with roughly ~30,000 riders on the bike. It was a hell of a lot of fun!

Stress levels

Call it 4/5 on the stress, with 5 being the highest.


Vegan stuff, including noodles with tofu.

My Day Job

Didn’t really do much. Whoops!

Investment real estate

Nothing here really.

CCIO: My business

TBD on this now!

Side Consulting

Not much actually

Huge data project

I did some powerpoint work and some Excel work, nothing crazy.

Company analysis

I had a past client reach out and ask me to do some analysis on a few companies and get it back to him within a few hours. It was a ton of fun, because the goal was to highlight companies that are misvalued by the stock market.

There are a lot of them!

Quick and easy $400

Sourcing new work

Emailed my contact to see if any work landed. Sounds like nothing yet

$10K/day website

Daily post


Time with the baby and fiancee.


Calls with recruiters and talks with fiancee about this new potential job.

Rescue Time Daily Screenshot

What I made today

Current Income  Streams

  • Job:  $170
  • Consulting Project: $350
  • Company analysis: $400
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $985

Planned income streams

  • My Business (CCIO)
  • WordPress Maintenance Site
  • Content sites
  • Micro-SAAS’s
  • Acquired businesses

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


Life Expenses: $89.73

  • Rent, utilities, Internet: $63.33
  • Phone Bill: $1.57
  • Heath 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

$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 $985 spent $103, which means….

Made $882 (pre-tax)

My plan for tomorrow

Tomorrow is Thursday, and I have to:

  • Follow up meeting with the big client of mine
  • Do some checks to a model to figure out why it’s not working all of the sudden
  • Follow up with the recruiter regarding the job

1,523 days until I turn $30. I’m making $10K a day passively by then

Dean Woods

Dean Woods

Dean’s goal is to create $10,000/day in passive income through entrepreneurship. Too many people write “success porn” that skates over the struggles many face in entrepreneurship. His goal is to create something real that highlights the lack of sleep, disappointment from family, and setbacks you really face in entrepreneurship. The hope is that $10K a day swill inspire someone else out there to make their entrepreneurship dreams happen. Dean Woods is side hustling and working a full time job to kickstart his entrepreneurial path. Prior to this life, Dean was a management consultant. Dean graduated with honors from The Wharton School.

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