The $0-$10K/Day Case Study: Day 115

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Day 115


If you’ve read the overview of the case study, then you might have noticed something peculiar.

I believe, strongly, that the way to reach $10,000 dollars a day of passive income by 30 is to leverage a variety of income streams to get there. Real estate is a big part of how my fiancee and I plan to get there. Another huge component, actually the largest, is income from a business.

We’ve started on the real estate investing and own 13 units, but I haven’t gotten started on the actual business yet. That probably seems weird.

A large reason for that is because I’m not ready: I need to balance the day job and side consulting in order to make more money and pay off my debt.

But another reason is that running a consulting business is teaching me such a wide range of skills that I wouldn’t have learned otherwise.

For example, I never would have learned how to sell something on the phone with a potential customer. I also wouldn’t have learned how to treat people right, especially during this pandemic.

That sounds like an edge case: why does learning how to treat people right during a pandemic help you as an entrepreneur?

The reason why is this time has taught me how to make customers feel like they matter to you, and that they are part of your family. That is a skill that truly matters for entrepreneurship.

It’s become a running joke: we’ve all heard from every company we’ve ever given our email too during this COVID crisis.

Check out this one I got from my internet provider: AT&T.


This is fucking horrible.

Read it. It is all “me” focused.

We’re here to help.  It just repeats “we” and “our.”

AT&T, I hate to break it to you, but no one gives a shit about how “you” are thinking about this.

There’s actually research that says the use of first-person pronouns “I”, “we”, “our” in emails pisses the recipient off because the email is all about the sender.

To stand out, be the company that cares about their customers more than themselves

During this time, I didn’t take the AT&T track. I did something different, and it made a world of difference.

For example, I had a client this past week (the financial modeling project) who is an active doctor working in a hospital right now. In my view, his time is WAY more valuable than mine right now. He’s literally treating COVID.

I made that exceptionally clear to him. He initially offered to try to speak here and there during his hospital shifts. I told him to call me when most convenient for him. So, we spoke late at night after his shifts, or early in the morning.

It’s a small difference, but it made a world of difference to him. He was very appreciative, and the next time he needs a consultant, I’d bet anything he hires me. I made it clear I care more about him than me.

Here’s another example. I work with an online platform that helps drive consulting work in my direction. I have a few contacts there that help send my name to clients.

I reached out to all of those contacts. I didn’t lead with the work. I asked them how they were doing. I asked where they were riding out the pandemic (they’re all over the country now). Then, I checked back in: “How are things in Connecticut? How are things in California?”

I didn’t talk about me. I asked about them.

Today, one of my contacts reached back out. She has more work, and she’s sending it my way.

Would she have sent that work my way if I hadn’t reached out to check in during COVID? Maybe.

But it took me only ~10 minutes to do these check-ins that turned “maybe” into a “hell yes.” It was worth the ROI of time to reach out.

Here’s the key piece though: you need to be genuine

Yes, reaching out to my contacts and clients benefits me. But the only reason there is a benefit is that I genuinely care about these people and want them to be okay. If I reached out, like AT&T, and it was all about me, then it’s not AT&T.

You might say: “well, Dean, sure you can call your clients. But AT&T can’t call everyone. I have a business with 10,000 clients, I can’t call them all.”

That’s true.

But, you can send an email.

Here’s how AT&T should have sent that email:

“Dear (NAME),

During this time, millions of Americans are home more than they expected. You need WiFi more than ever to work from home, for your children to attend “Zoom School” or to log on to your state’s website to apply for unemployment. You need access to streaming services to watch movies with your significant others or help with entertain your children.

You need AT&T more than ever right now. The team here is working around the clock to make sure the service continues to keep working to support you. If you have an interruption in service or are struggling to pay your bills, then click this link to let us know. We’re on it.”

Much better, right? It’s about the customer.

Success in business is about listening to the customer, delivering what the customer wants, then provided the best in class customer service.

It’s getting me more clients during COVID. You can do it too.

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

The current phase of the plan

I’m in Phase #1:  The Job & Side Hustle Phase.  You can read more about the phases and my plan to get to $10K/a day at 30 here.

Wake up & sleep:

I slept well, 7 hours and 52 minutes, waking up at 6:59 and going to bed at 10:36.

Whooop had me at 79% recovered, and I believed it. I was feeling energized and was cranking through work in the morning/


Pretty shitty here. I didn’t do much but definitely should have.


Diet was okay. I had curry for both breakfast and dinner. Honestly, hard to beat from a tasty perspective.

However, it was only okay because I was well-rested. Otherwise, this would have killed my energy level.

My Day Job

Probably 5 or 6 video chats.

I’m doing a couple projects at the office now. I’m only working ~2 hours a day here though right now, which is honestly great because it helps save up free time for consulting work.

However, it makes me nervous that I could be axed.

On one hand, it would save a lot of free time for me to try and do more consulting work.

On the other, it’s a guaranteed $170/day and I don’t know if I can give that up just yet when I’m still in debt. Once the debt is gone, I don’t give a shit.

Healthcare while freelance consulting is also a consideration. However, my day job has absolute shit healthcare and I’m already paying $300 a month for better insurance. Buying the same health insurance on the market is also $300, so it doesn’t move the needle.

Investment real estate

Busy day here on both the 6 unit and the 7 unit. I spoke with both property managers today.

6 Unit

The six-unit is the one we just bought and has a good property manager. We just heard from her yesterday.

There are two vacant units, and she already had one full unit rehabbed (new paint, new floors, build out a closet because there weren’t closets). That cost $1,700 to do.

There’s one other piece. This property is a former motel, so the units are ~450 SF and don’t have ovens. We plan to add ovens to help raise the rent. The plan was to add little electric ovens. However, the property manager found out the building wasn’t wired for the correct wattage to put electric ranges into the building. Adding in that wattage would be expensive as shit.

However, the building does have a gas line in the basement. As a result, we could just extend those gas lines and put in gas ranges.

That’s interesting but risky. Here’s why: the building is in a cold area of the country. As a result, gas prices rise a ton in the winter and our utility expense will kill our cashflow.

I asked the property manager to get a quote for submetering. This means a little instrument on the gas line that measures the exact amount of gas each tenant uses, so the tenant can pay for their own gas use. This protects our cashflow and keeps tenants happy. If we don’t submeter and try to charge tenants an equal amount off the gas bill, then tenants get pissed. “Sally in unit #12 uses more  gas than mee, why  am I getting billed the same as her?”

We’re getting a quote on that today. It should be ~$350 for the gas oven, and then ~$500 per unit for the gas line.

All in, we’re spending ~$2,500 per unit on this rehab. The units pre-rehab rented for $450. Post-rehab, we should get $550. In other words, we’ll make an extra $1,200 per year on an upfront $2,500 investment for a 48% ROI in year #1.

We’ll also get highe quality tenants who are more likely to pay on time.

We’ll take it.

7 Unit

They finally got the two vacant units on the market (5 months later). I’m optimistic these units will be rented before next’s month’s rent is due.

Side Consulting

I have a few projects going on now.

Business plan

I heard from this client and we’re speaking on the phone tomorrow.

Private Equity

I heard back from these guys. It wasn’t great: they heard from someone that my logic might be wrong and they have asked me to fix accordingly. I’m in a holding pattern until this is resolved, but not a good sign. Also, the first time I’ve ever had a client question my work.

Financial modeling

Well, as one cannabis financial model project finished, another arises. I’m not building another model for a cannabis client. This one is a week-long and the one I referenced the other day.

Sourcing new work

I had a call with another PE client. They are pre-interviewing because their need shows up quickly and they don’t have time to interview then.

The client and I had a similar emphasis on the importance of communication so he said I got the job, whenever it may arise.

$10K/day website

I spent ~30 minutes to publish yesterday’s post. My redesign is getting closer, so I’m very excited about that!

I also published a few old pieces, especially about learning from others, why newspaper comment sections are great, and how to build a reading tracker in Google Sheets.


Lots of fiancee time


Nothing Misc today!

Rescue Time Daily Screenshot

A much better day with 10 hours of work and productivity about 75.

What I made today

Job: $170

Rental Income: $33

UpWork: $0

Consulting: $225

My business: $0

Affiliate: Not doing yet

WordPress Maintenance Site: Not doing yet

Dividend Income: Not doing yet

Micro-SAAS’s: Not doing yet, 

Hotels: Not doing yet

Dividend Income: Not doing yet

Total: $428

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

Expenses: $250

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

Today’s Income (pre-tax)

Made  $178

My plan for tomorrow

Tomorrow is Friday and I’m going to:

  • Follow up work for business plan client
  • Maybe finish a piece I’ve been working on for $10K
  • Make my fiancee cookies

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. His goal is to create something real that highlights the lack of sleep, disappointment from family, and setbacks you really face in entrepreneurship.

To read more about how this case study is set up, check out the ground rules here.

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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