The $0-$10K/Day Case Study: Day 178

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Day 178


It’s been a few days. I’m sorry about that; my objective is to update this website every day.

There are two big things going on that are top of mind for us this weekend: a place for us, and a job for me. I’ll try to describe them both in good detail to explain how we’re thinking about these both.

The place for us

We may own 13 apartment units with 49 more on the way, but we rent ourselves. The rental is honestly pretty shitty. It’s $2,200 a month, but it’s old, dirty, has a ton of bugs and landlords who smoke. There are a lot of negatives about the place.

With all of that in mind, coupled with our love for real estate, we are always looking at the market for real estate in the area.

In our area, there are two things we could conceivably do. The first is buy a house. That’s the American dream, but it’s also not the greatest investment of all time. The second is better: we buy a 3 or 4 unit building, live in one unit, and rent the others out.

We found a really good 3 unit building, in a great area, with two units rented and the third vacant for us to live in. It’s a beautiful building (just look at this thing!) and we went to look at it this weekend.

The two rental units in it rent for $4,100 and $3,200 respectively for a total rental income of $7,300 a month or nearly $88,000 per year.

However, the damn monthly payment is going to be ~$14,000. So, we’re out of pocket $7,000 a month, and that’s assuming full occupancy. You might argue that’s not bad because we’re paying $2,200 a month for rent now and by owning a place, we’ll get equity build up and the homeowner’s tax benefit.

But, there’s a bigger problem that you might have guessed based off that monthly payment.

This building is for sale for $2.6M.

Said differently, we would have to pay ~$550,000 for 20% downpayment and closing costs for the luxury of paying $7,000 a month in the mortgage.

Fuck. That.

If we take the same $550,000 and bought a ~$2.5m investment property out of state at an 8% cap rate, we’d expect an NOI of $200K per year and a total cashflow of ~$50K per year.

So, we’re not going to be buying anything for a long time. It’s the rental life for us.

The job for me

I’ve been talking with a VC firm about a job for a couple days now and have spent ~4 hours total on the phone with them. We have a pretty good rapport, so I think it could be an interesting fit. It will probably take another ~4-6 weeks to resolve though.

I’d like the job, but no biggie if I don’t get it.

In one scenario, I get the job and work there for a year and make a good amount of money but slow down on the consulting. Then, I go and start CCIO.

In another, I don’t get the job, I quit my current job, keep consulting at the same rate, and start CCIO.

At the end of the next 12 months, the end result is the exact same:

  • I make the same amount of money, just the mix changes between from this new job or from consulting
  • I still end up working on my business

So, we’ll see what happens. For now, I think still an interesting conversation to continue having.

Yesterday there were 1,519 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:

Been in touch with Whoop support; I’ll follow up here


I did a 60min Club Bangers workout on the Peloton and loved it! I’m now pretty consistently finishing in the top 3-5% of each class that I take, which is super fantastic.

My fiancee and I also went for a four mile run together this weekend, which was also a total blast and good to get out there together.

Stress levels

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


Lots of vegan stuff still.

My Day Job

This is essentially a non-thing right now.

Investment real estate

I exchanged some emails with a guy on BiggerPockets who reached out about the property. It sounds like he might actually give us an offer, which would be super interesting to see and get!

CCIO: My business

TBD on this now!

Side Consulting

Not much actually

Data Project

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

Company analysis


Sourcing new work

I’ve lightly tried to get more work here, but nothing has landed. I should start getting more aggressive here today.

$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

It’s been a few days so no up to date screenshot here

What I made today

Current Income  Streams

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

Total:  $585

Planned income streams

  • My Business (CCIO)
  • Content sites
  • 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 $585 spent $103, which means….

Made $482 (pre-tax)

My plan for tomorrow

Tomorrow is Tuesday, and I have to:

  • Try to land a new client or two
  • Make a post on $10K
  • Do a quick research project for the potential company I might work with

1,518 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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