The $0-$10K/Day Case Study: Day 158

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Day 158


In entrepreneurship, there’s often told advice that says you need to avoid analysis paralysis and just get out there and start. The often told example is that you can’t figure out how to make $1,000,000 as an entrepreneur if you can’t figure out how to make $1.

This is all entirely true. I firmly believe you should get out there and get started. If you don’t get started, then you won’t have any success at any point.

But, you could get taken advantage of if you don’t know what you are talking about.

Just yesterday, three different groups all tried to take advantage of me.

Group #1: The Design Agency

This is a design agency that is looking to sell me a website for $40K and a “design workshop” for $20K. Overall, I think the website at $40K is a good value and I would probably happily hire them to do so.

However, they also pitched me a “design workshop” for $20K. This workshop would be over the course of two days and would be entirely focused on figuring out who my core buyer is, how to reach them, what messaging they would resonate with, etc.

Now that is a rip-off and trying to take advantage of me. There are dozens of extremely well-regarded books on this topic, as well as hundreds of resources online. This isn’t worth it at all.

So, I told them that. They immediately realized I wouldn’t fall for it, and then walked it back. Their tone made it clear they try selling this $20K workshop to rookies to make money off of them.

Group #2: The outsourced sales agency

These guys actually reached out to me. They are a sales agency: I hire them and they handle most of the sales for me by identifying and reaching out to potential sales prospects. They then qualify that person, then send it over to me to handle the close.

They pitched me a $10,000 a month retainer and they expect 5 sales prospects per month to convert.

This is bullshit. The lead gen agencies I’ve worked with in the past charge me about $1,000 a month and get me ~30 meetings per month with qualified prospects.

Again, another rip off. But these guys are flashy and good on the phone (obviously, since they are sales guys!) so I’d bet they get rookies to buy from them.

Group #3: The realtor

This one really pissed me off.

We are about to buy 49 units from this investment group, the same group from which we bought the 6 unit. Things are with the banker right now to approve, but we should be signing this deal on Monday or Tuesday (so in a  few days).

The agent, who represents us and the sellers, did something shady. The properties are listed on Zillow and Loopnet, with Loopnet being the Zillow for larger commercial investment properties. I think the agent assumed we didn’t know about Loopnet, because he went onto Loopnet and adjusted the listing. However, that means that the property that we are about to sign on was sent as a notification to thousands of people around the country as recently updated. He probably got dozens of calls on it, and he tried to do it behind our back.

If I didn’t know about Loopnet, we wouldn’t have known this was happening. He could have solicited another offer, and then told us “sorry, someone came in with a bigger offer.”

Instead, I texted him: “Hey (realtor), we saw the change to the cap rate on LoopNet so figured would check-in. We are ready to sign a contract as soon as w get a thumbs up from the (banker); we’ree hoping to be under contract early next week.”

He texted back and I think got the message underlying my text:

  • We know you did something shady
  • If this deals falls apart, we know it’s because you knowingly made it fall apart
  • If you go forward with shadiness here, then it’s you actively choosing to cause problems

We like the realtor, so I’m optimistic me giving him a heads up we knew what was going on would keep him from pushing down this direction.

In short, you need to get started. But learn as much as possible before then

You do need to get started, optimally as soon as possible.

But, if I hadn’t studied for years before starting myself, yesterday I would have:

  • Blown $20K on something I didn’t need
  • Spent $9K a month more than I need to on sales
  • Lost out on 49 units that will cashflow ~$70K a year

You might not be ready to start your business yet. You may be waiting until you graduate, until you have money saved, until after your wedding, etc.

That doesn’t mean your time right now can or should be wasted.

Listen to podcasts every day while you exercise or commute. Get through 75 non-fiction books a year, at a minimum.

Make the time count until you are ready to start.

Yesterday there were 1,585 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 woke up at 7:26 after going to bed at 11:43,  for total sleep of 6 hours and 53 minutes and total recovery of 87%

Overall, pretty good. I felt the energy levels yesterday be really great, which was fantastic!


Limited exercise yesterday led the day strain to be lower at only 8.6.

More exercise needed

Stress levels

Stress was probably a 3/5, with 1  being the highest. Feeling good.


Coffee, protein shake, but some wings for dinner. 5/5 with 5 being the worst.

My Day Job

Honestly nothing. I’m barely doing anything right now.

Investment real estate

There were two things here.

The first was the texts about the  49 unit acquisition, which I talked about above. The other was our 7  unit that has shitty property management.

We actually called our realtor for the area to talk to her about selling it. I hate the idea of getting rid of the property, but the manager blows and getting money out would allow us to more easily buy the 49 units we really want.

The agent is looking into the numbers for us this weekend, but being able to get cash out here would be fantastic.

My Actual Business

Not much right now.

Side Consulting

On the back end of work here!


One call

Market Research & Customer  Interviews

The client was pretty happy here with some very small tweaks suggested. A little follow-up work, and I should be in line for a really nice, fat payment in a few days!

Sourcing new work

Nothing really here. I’ll need to do some of this post-baby.

$10K/day website

Published the daily post.

I also published why you shouldn’t try to make money with Kindle KDP


Walks with fiancee



Rescue Time Daily Screenshot

What I made today


Current Income  Streams

  • Job:  $170
  • Rental Income (13 rental units): $43
  • Framework: $250

Total:  $463

Planned income streams

  • 15 websites
  • My Startup
  • Local Serviced Based Business  (cleaning business)
  • Affiliate
  • WordPress Maintenance Site
  • Content sites
  • Franchises
  • Dividend Income (municipal bonds)
  • Micro-SAAS’s
  • Hotels

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: $12.00

  • Peloton: $3.20
  • Gainful Protein Powder: $1.80
  • Care/of Vitamin pack: $3.00
  • 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: $302

  • Gusto to pay myself: $1.50
  • Quickbooks to track expenses: $0.40
  • Google Business Email Account: $0.40
  • Fiverr for virtual support: $0

$10K a day: $12.42

  • 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
  • Rhino Rank for SEO: $10.83

Real Estate Investing: $0.52

  • Legal Zoom Registered Agent (all LLC’s): $0.52

Today’s Income (pre-tax)

Topline of $463, spent $119, which means….

Made $344 (pre-tax).

My plan for tomorrow

Tomorrow is Saturday, and I need to do:

  • Some small tweaks for my existing client
  • Some writing here on $10K


1,584 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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2 thoughts on “The $0-$10K/Day Case Study: Day 158”

  1. Hey Dean!
    You haven’t been posting for a month. Everything okay?


    1. Hey Thompson! Thanks for checking in 🙂

      We had our little baby show up so I’ve been offline from all work with the baby! I’m coming back to work in just a few days and will start posting again!

      Looking forward to sharing some thoughts and work together soon!

Comments are closed.


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