The $0-$10K/Day Case Study: Day 88

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Day 88 of the $0-$10K/day case study


What I did today

Yesterday was an interesting day.

I had slept a ton (which you’ll see below) and was generally productive, although I’d always love to be more productive in general.

But, it  wasn’t until night that things got weird. I just couldn’t fall asleep. My brain was up and just didn’t want to stop. I was thinking and thinking and thinking.

Most (all) of my thoughts were about all of the cool stuff I want to do with my businesses to get to $10K/day at  30. I couldn’t stop thinking about it, which meant I couldn’t get my brain to slow down.

Here’s the world I was thinking about:

I use all of this year and next to figure out how to get my Affiliate sites up, running and effectively making $2,000/month. The playbook to do that should be relatively simple, it’s just a function of doing all of the grunt work to get it there.

I’ll have 4 sites that are generating income by the end of 2020, with two of them generating more than $500, one generating ~$200, and one generating $50. This is based off when I’m planning to launch those sites and how much content I’m planning to have on those.

I’ll also be starting to introduce virtual assistants who will help me with a lot of the grunt work of these sites that suck up a ton of my time. I’d love a team of a few writers, an editor, and a post formatter, and a few Quara/Forum/Blog commenters. My role will be to oversee the entire process, assign keywords, and manage the SEO. I’ll have a couple tools to help me (Surfer SEO, Ahrefs, Pitchbox). I’ll also have a technical guy on staff who can help me fix the any technical issues with my sites.

I’ll have ~55 eBooks published on Kindle, which should be another  $1,000/month. I’ll do keyword research and then send those to my writers. Once they’re done, I’ll format those up and add them to KDP. I’ll have a guy manage my Amazon advertising to make sure I’m selling these books at a profit.

I’ll be using the income that comes in these sources, consulting, and my job (if I have a job!) to buy more real estate. My goal is to end 2020  with 60 units. That should provide roughly $6,000/month in pure cashflow.

If all of these come to pass the way  I’m hoping, it should be:

  • ~$5,000/month from job (maybe-dependant on if I  get laid off)
  • ~$2,000/month from websites
  • ~$1,000/month from eBooks
  • ~$6,000/month from real estate

That gets me anywhere from $9,000-$14,000/month, and that’s before the consulting that drives the majority of my income.

That amount of money in will free up my time pretty substantially by allowing me to “double down” in investing. I’ll spend 2021  building up more affiliate websites, more ebooks, and more real estate. I’ll also introduce Youtube to the game plan to start growing and building cashflow YouTube channels. Consulting, when not in COVID world, should continue to bring in ~$10K/month as well.

In 2022, I’ll continue to blow out on all of the above, which should be pretty automated at this point.

But, what I’ll do now is start to buy assets. I’ll look to buy established web business, websites, and primarily SAAS products that are for sale in the ~$50,000-$100,000 range. Those should have an ROI  return of >30% and be well-worth the investment. At that point, I’ll start onboarding a Social Media Manager to handle growth. I know exactly who I’m going to hire for this.

I’d also love to buy and grow a few other business types at this point, like subscription boxes and physical products through different Shopify storefronts.

I’d also need to hire a bookkeeper to keep all these numbers sane for me!

Witha ll of this, it’s leading to a world where 2022 ends with:

  • ~$30,000/month from Affiliate websites
  • ~$10,000/month from eBooks
  • ~$10,000/month from YouTube
  • ~$30,000/month from real estate
  • ~$20,000/month from purchased SAAS businesses

That is, by my math, $100,000/month before counting for consulting income.

Isn’t that exciting?

I couldn’t sleep thinking about that.


It wasn’t the excitement that had me thinking about that. It was the fact there are literally thousands of hours of work per year necessary to get to that point. I’m behind where I need to be to get to that point. Very behind, actually.

I need to work more. Work harder. And not stop.


Wake up & sleep:

So I didn’t sleep well last night into this morning (remember I write these in the morning following). So, the crappy sleep of tonight will show up on tomorrow’s case study.

For this case study, I got 9 hours and 1 minute of sleep, going to bed at 9:17 and waking up at 6:59 am.  But, it wasn’t super restful and my data says I only got 50% of the way to recovery.


No exercise here today, just walks around the apartment to stay moving during COVID.


Relatively good. I have a bunch of vegan chili that I made.

My Day Job

A couple meetings via Zoom, but that’s about it.

I’m somewhat expecting the amount of work the day job has declines over the next few months as people begin to feel like there is no point to work since they’re locked in.

Investment real estate

Just standard scrolls here today; no purchases or action.

I looked at some really nice buildings that were in the $6-$8M range in prime locations, like Chicago and NYC.


I read a lot on Reddit  Self Publish to understand how people who are making big money on Kindle are doing it. It was helpful!

Amazon Affiliate Websites

I published ~4,000 words of content, below the 5,000-word target. Today needs to be a touch more to catch up!


I had a pitch call that went really well, but I don’t think it’s a good project. In fact, I think it’s set up to fail and the price (~$2,000) isn’t worth it for a crappy review on my Catalant page.


Fiancee time!

What I made today

Job: $170

Rental Income: $33

UpWork: $22.50

KDP: $0

Consulting: $0

Medium: $1

Amazon Affiliate sites (2 sites): $0

Youtube: $0

Total: $226.50

Today’s pro-rated amount of monthly expenses

Expenses: $250

Once I  pay off my debt, I’ll break out expenses into a line by line as well.

Today’s Income

Lost $13.50

My plan for tomorrow

I need to generate 5,000  words of content, write more on one of my eBooks, then add a bunch of my existing eBooks into new and better categories.

About the Author & The $0-$10K/Day Case Study

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

The hope is that this series of posts will inspire someone else out there to make their entrepreneurship dreams happen.

Dean Woods is currently an executive by day and a bootstrapped micro-startup CEO by night. Prior to working in startups, Dean was a management consultant. Dean graduated with honors from The Wharton School.

What I did yesterday to make $10K a day at 30

The current phase of the plan

Wake up & sleep:


Stress levels


My Day Job

Investment real estate

My Actual Business

Side Consulting

$10K/day website


Rescue Time Daily Screenshot

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

Today’s Income (pre-tax)

My plan for tomorrow

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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