My Journey to $20M in assets

Chicago, Illinois

Land & New Construction

My Journey to $20M in assets

Daniel Ortiz de la Garza

Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes

Hey all,

After thinking it over I decided to create a new thread.

I am a small time passive real estate investor who has ambitions to expand greatly, first to $20M and perhaps maybe more. i guess I will give a little bit of background on my journey up to now.

I am 38 y/o, Electrical Engineer by day, Architectural enthusiast by night. I was deployed to Iraq in 2007 and through a mentor got word of a book called The Fountainhead. Incredible book that has probably changed my life more than any other book I have read (though admittedly I do not read much) As I poured over the 700+ pages I fell in love with the spirit that was protagonist Howard Roark, who defied convention to make more beautiful architecture and was loathed by society, especially the ruling class. I forgot how the book ends but one of the high points was his design of a chapel "for the worship of God and the service of Man". I had no idea what Ayn Rand was writing about was a REAL person: Frank Lloyd Wright. Fast forward a year later I am at home (Chicago) and find myself in the beautiful suburb of Oak Park. Imagine my surprise as I walk up to this structure, thank god I was "awake" enough to be able to notice this beautiful piece of Architecture:

The enigma that was Roark hopped out at me in real life in the form of his temple, in reality it was designed by Frank Lloyd Wright. This was a turning point in my life. Since then I have dedicated most of my free time to study Wrights work, developing myself as 1st an Architectural Drafter, and now as a conduit of beautiful Architecture and interior/exterior design in the spirit and style of Frank Lloyd Wright. I have moonlighted for several Architects and through hard work and good fortune stumbled on an opportunity to become an apprentice electrical engineer. 10 years later I am a senior engineer, together with my wife, have a decent portfolio of Real Estate. I always suspected that to achieve anything of great notoriety in Architecture one needed to have access to wealthy friends or develop projects oneself. Not having the latter I find myself on a journey to build a portfolio not just for wealth's sake, but to move the proverbial needle on beautiful design and provide a more pleasant built environment for all!

So that is me. Thanks for reading and I look forward to posting weekly progress on here. Cheers and hope you all have a great weekend!

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Jonathan KlemmBusiness Member

Moderator

Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes

2y

Hey @Daniel Ortiz de la Garza - Really appreciate the share. Thank you for your service, it goes without saying that you are an amazing civil servant.

Your story caught my eye...I started out studying architecture and quickly shifted to construction engineering as I was a bit more analytical than I was creative at the time. Nonetheless, I still appreciate great architecture. Love the part of your post about "worshiping God and serving men and women!"

I am down in Chicago, but out in that area often so if you ever want to talk architecture and construction let me know. Excited to see your weekly updates! Given your background I expect you to be pretty disciplined in that task.

[email protected]

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Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
2y
I am through module 1 of Kai's course and it is definitely like drinking water out of a fire hydrant. Too much to recap, but it is very skewed to the "fundamentals of having a successful overall business". Meaning how to attract the type of people you want to your STR listings and how the heck you are supposed to know if there is a market for your type of "customer" in the area you are investing. I honestly needed this awakening. Chugging along. Currently playing with the idea of buying acreage in the west burbs of Chicago and design/ building a duplex and then another and another. We'll see where it goes either way I am determined to design build something to make into a successful STR business.
oh yeah and currently taking a major L on QQQ shorts that I was probably too early into. I have 6 month calls on TLT and redfin which should do well in the apparant recession that we are running headfirst into this fall/winter.
I am out of long term stock market and my opinion is it is dangerous to be in right now unless you are going to stay in for years.
Cheers folks!
0 Reply
Richard Rao
Investor · DFW · Member since 2022 · 2 posts · 1 vote
2y
Dan, do you own any real estate as of now? what does your current financial situation look like? I see that you have a goal to own 20 million in real estate but what do you want to do with it? Live off cashflow? Sell and cash in on the equity?
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Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
2y
Quote from @Richard Rao:

Dan, do you own any real estate as of now? what does your current financial situation look like? I see that you have a goal to own 20 million in real estate but what do you want to do with it? Live off cashflow? Sell and cash in on the equity?
Hey Richard,

Welcome to the party!

Here is a recap:

1. Currently at 1.1M in assets
2. Too much bad debt 😅 kind of a joke
3. As cliche as it may sound my goal is the process. I care deeply about good Architecture and being a developer is the best fit for me to introduce a better built environment. I will figure out what to do with it when I get to $20M, but it will probably just be finding new ways to improve built environment along with travelling more and spending more quality time with fam.

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Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
2y
Hi all, thanks for the recent likes. I have been trucking along with Kai Andrews course, through 3 modules already. I am starting to have some doubts about the feasibility of Short term rental in the Chicagoland suburbs. Anyone know of a successful BNB'er in Chicago or near suburbs?
Still, I am making it a commitment to finish the course 1 video lesson per day. Recently i met up with Jonathan K. and it made my whole month. Incredibly sweet guy, and was very interested in my story, and shared his which is super inspirational! What also inspired me was meeting an entrepreneurs that is making things happen and building wealth near me! So huge. Anyway that's it for now, back to the grind, cheers folks!
1 Reply
Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
2y
Quick update: I am 3/4 through the landhacker course and I can resoundingly say it has been worth probably 5x the value I paid for it ($2500). So many golden niggets that Kai opens up about and reappy lays down a blueprint for starting a successful STR. My goal for this is to finish the course within the next 2 months and come up with a plan and proof of concept STR somewhere within 15 minutes from my home. I feel myself seeing the c9mpounding results of drilling down on the course and real estate investing the last few months. I will try to post some entertaining updates on here and less nitty gritty like this or maybe mix them both up.
love yall!

P.s. its going to be Q4 2024 in a few days!!!! Do you feel like you are stepping up and doing what you need to do to obtain the life and results you desire?

Cheers yall
0 Reply
Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
A few things happened since I last posted, most of which I would rather not say but suffice to say I am plaving the airbnb learning on the back burner for now in favor of focusing on aqcuiring land and building a multi unit from scratch. It will be a 3 or 4 unit and planning on doing STR on one as an experiment. I will still post on here weekly but currently these are the things I am working on:

-Vetting my options for financing

-Vetting other parties and areas for best success on this dream project of mine.

I have a few ideas on the concept and will eventually reveal it here 🙂

Cheers folks keep chasing your dreams!
P.S. : ever since meeting with Jonathan from quality builders I have been buzzing with excitement, so a special shout out to him, not that he needed my endorsement but I really appreciate his help and hope to collab with him soon on something🙂
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Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
I have been less active on the investor homefront dealing with an unexpected curveball I got thrown in life.
Still have big goals for Q1 2025:

-Get Pre Qual'd for VA construction loan(may be until later in the quarter as I also have to refi out of my current VA loan to regain full entitlement.
-Find a lot and all else that comes with a new build and start building late Q2, early Q3.
I understand this is a snails pace, however I am still a W2 enployee so all this will be a 2nd job for me. Also, I have learned in all things that are expensive that a good rule of thumb is go SLOW. I always need to remind myself about that, because I also (like many millenials) have a problem remembering what my bigger picture goals are, so I tend to want to sprint so that I don't forget and hence lose myself in the flywheel that is day-to-day living. As hilarious as that sounds it is the case, and that is where this board helps so thanks all on here and BP!
Until next time: same bat time, same bat channel🤘✌️
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Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
Not much in the way of updates, except for meeting with lender in December to go through some scenarios for the multi unit ground up build.

Very excited about this.
I am also still on the fence on the design aesthetic. Ideally I want a combination of the Burnham block duplex style but cleaner, and more usonian looking. Sorry for the imvestors out there that had eyes glaze over after reading that, I will post some photos on my next post.

Stay well!!
1 Reply
Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
Hope everyone is having a great holiday season. I am very committed to investing in a multi family building this coming year.
I also feel the need for a mastermind group and will be doing a google search for one around me for multi long/ mid and short term investing.

Cheers, just wanted to put an update on here!
0 Reply
Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
Huge update!!!!
after alot of procrastinating (like since I started this thread) I was pushed to write a business plan for my dreams in RE and Architdcture. Huge shout to Tony Glenn Marine Real Estate investor for pushing me to do this on his youtube channel.
so my $20M goal will be reach by 2032!!! Sounds like a long time but it really isn't. This is being very conservative with all the numbers, if anyone is interested in specifics I can provide in a pm.
Super excited, as now I have a target AND a plan for my goal.
lets ****ing go.
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Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
Well its been 2 months since an update. I have a few options in play right now for my goal of adding another property to my portfolio this year, it seems like the Chicago market is yelling at us to invest into single family homes in B+ areas. Just my observation anyway, I do want to design/ build something at some point but land prices are pretty rich right now. The formula that is sticking out as a potential to me is what I have been doing quietly the last 6 years: buying a cosmetic SFH fixer in B areas with 3% down, live in and renovate, long term rent and repeat. Anyone else seeing success with a different strategy around the Chi?
0 Reply
James Phillips
Developer · Eugene, OR · Member since 2016 · 54 posts · 30 votes
1y
Hey Dan,

I've loosely followed your journey on here--thanks for continuing to share. I have a similar passion for Wright, Rand, and for architecture. I'm coming at it from the finance side; I'm currently wrapping up my graduate degree in finance.

I think your general ethos aligns with the ideas outlined in ULI's incredible book for developers; I definitely recommend: https://a.co/d/2g0bxnx

Have you thought about investing out of state? I'm in the small Eugene market, which in terms of industry and jobs offers no real reason to be here. Population and job growth just isn't ideal. As a result, I'm thinking about investing in higher growth areas in the Midwest. There are a lot of places that stand to grow significantly over the next couple of decades but that are still affordable enough for learning/growing stage investors. Moreover, many municipalities are adopting new middle housing codes, so if you pick up properties at affordable rates that have big lots, then after a few years of appreciation you'd be in a good position to redevelop them.

Hope you're well, stay in touch!

2 Reply
Jarret Jarvis
Real Estate Agent · Chicago · Member since 2021 · 168 posts · 62 votes
1y
Hey Dan,

Thank you for sharing your journey—what an inspiring story! It’s incredible how literature and architecture can have such a powerful impact on someone’s life and direction. I love how you’ve integrated the lessons from The Fountainhead and Frank Lloyd Wright into your personal and professional journey, especially as you pursue both beautiful design and a growing real estate portfolio.

Your ambition to scale up to $20M and beyond is exciting, and I’m sure with your drive, experience, and passion for architecture, you’re on the right path. I look forward to seeing your progress and hearing more about how you continue to balance these ambitions with the pursuit of creating impactful spaces.

Thanks for sharing, and best of luck as you continue on this incredible journey!

Cheers,
Jarret
1 Reply
Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
Quote from @James Phillips:

Hey Dan,

I've loosely followed your journey on here--thanks for continuing to share. I have a similar passion for Wright, Rand, and for architecture. I'm coming at it from the finance side; I'm currently wrapping up my graduate degree in finance.

I think your general ethos aligns with the ideas outlined in ULI's incredible book for developers; I definitely recommend: https://a.co/d/2g0bxnx

Have you thought about investing out of state? I'm in the small Eugene market, which in terms of industry and jobs offers no real reason to be here. Population and job growth just isn't ideal. As a result, I'm thinking about investing in higher growth areas in the Midwest. There are a lot of places that stand to grow significantly over the next couple of decades but that are still affordable enough for learning/growing stage investors. Moreover, many municipalities are adopting new middle housing codes, so if you pick up properties at affordable rates that have big lots, then after a few years of appreciation you'd be in a good position to redevelop them.

Hope you're well, stay in touch!

Hey James,

Thanks for the comment! Wow it sounds like we are kinda "brothers from another" haha.

It is extremely rare to find Millennials that are into Wright much less Rand :). Also thanks for following the journey.

Yeah the investing out of state thing seems to be a simmering trend right now. There is probably much to gain from that.

My personal take is investing is hard enough without having the added complexity of building a remote team of folks that can handle things for out of state deals. (Contractors, quarterly tenant checks, etc.) I am always open to any trend but right now I am compelled to restrain myself to the local market, my rule of thumb is 25-30 minutes drive from my home. Wildly enough, a property of mine had a furnace failure this past Friday that turned the last few days upside down. Luckily I have a local team that is incredible at responding and was able to replace the blower motor at a nominal cost. I couldn't imagine how hard this would have been to navigate if property were even 1 hour away.
1 Reply
Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
Quote from @Jarret Jarvis:

Hey Dan,

Thank you for sharing your journey—what an inspiring story! It’s incredible how literature and architecture can have such a powerful impact on someone’s life and direction. I love how you’ve integrated the lessons from The Fountainhead and Frank Lloyd Wright into your personal and professional journey, especially as you pursue both beautiful design and a growing real estate portfolio.

Your ambition to scale up to $20M and beyond is exciting, and I’m sure with your drive, experience, and passion for architecture, you’re on the right path. I look forward to seeing your progress and hearing more about how you continue to balance these ambitions with the pursuit of creating impactful spaces.

Thanks for sharing, and best of luck as you continue on this incredible journey!

Cheers,
Jarret

thanks for the comment and kind words my friend :)
0 Reply
Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
So small update on here, I managed to carve some time to begin to set things up to spring board for a deal in the next 2-3 months. I will definitely miss my target of having something before end of Q1, but I am pleased with my progress, and momentum.

I am meeting with an attorney in the next few days to discuss business structure, and other things, and after that my goal for March is to have a meeting (along with my business partner) with an awesome MLO that was recommended by the great @Jonathan Klemm .
Important thing I wanted to plug here is a free mastermind meetup I am planning for March around Naperville. This will hopefully be a monthly meeting of high vibe RE investor folks to learn from each other and have community, everyone is welcome. Drop a comment or DM if interested and I will be happy to share details.
Cheers, and lets be safe with these single digit days coming up!
1 Reply
Henry Lazerow
Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes
1y
Congrats fellow Chicago member! You sound like a very intelligent person and should do good in this. @Jonathan Klemm is a great resource! I would recommend house hacking, it’s easiest way to get started. My first deal was 5% down house hack on a 4 unit and then I used equity from that first deal to do 2 more deals once with a cash out refi and once with heloc. Currently looking for my 4th deal while also working as a realtor helping others.
2 Reply
Jonathan KlemmBusiness Member
Moderator
Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
1y
Welcome back into the BP world @Daniel Ortiz de la Garza - I still love that you are sharing your journey here very helpful for others and vulnerable of yourself.
There is still hope for a Q1 deal if you are aligned and focused....but if time doesn't permit, just keep going with the flow of life!
Regarding your mastermind idea...I strongly suggest you come to our Chicago meetup this coming Saturday...we switched up to a mastermind format, and if you like it, we could figure out a way to partner up and start a suburb version.
Here is a link to the meetup: https://www.biggerpockets.com/forums/521/topics/1230572-chic...
[email protected]
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Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
Quote from @Henry Lazerow:

Congrats fellow Chicago member! You sound like a very intelligent person and should do good in this. @Jonathan Klemm is a great resource! I would recommend house hacking, it’s easiest way to get started. My first deal was 5% down house hack on a 4 unit and then I used equity from that first deal to do 2 more deals once with a cash out refi and once with heloc. Currently looking for my 4th deal while also working as a realtor helping others.
Thanks for the encouragement! And congrats on your success as well! How long did it take for you to acquire the 3?
0 Reply
Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
Quote from @Jonathan Klemm:

Welcome back into the BP world @Daniel Ortiz de la Garza - I still love that you are sharing your journey here very helpful for others and vulnerable of yourself.
There is still hope for a Q1 deal if you are aligned and focused....but if time doesn't permit, just keep going with the flow of life!
Regarding your mastermind idea...I strongly suggest you come to our Chicago meetup this coming Saturday...we switched up to a mastermind format, and if you like it, we could figure out a way to partner up and start a suburb version.
Here is a link to the meetup: https://www.biggerpockets.com/forums/521/topics/1230572-chic...
RSVP'd thanks for the heads up🙂

1 Reply
Henry Lazerow
Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes
1y
I got the 2nd deal 4 years after first and 3rd deal 5 years after first. Was focused a lot on being a realtor have brokered 50 million now but if knew they would appreciate so much probably would have just focused on buying more myself. I find year 3+ of owning is when buildings really stabilized and rents gone up, most won’t really support a refi until 3+ years especially at today’s rates unless got a crazy deal.
1 Reply
Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
As February is winding down, I have quite a bit to be excited about.
I have made the commitment to change industries into construction from utility engineering this year. I also still have the goal of getting into 1 deal this year, with a friend and business partner.
I attended the Cashflow Breakfast Club networking event this past weekend and it was awesome. Highly recommend for anyone in the Chicagoland area, I believe there will be 11 more sessions. Panelists were seasoned pros, very helpful and I was surprised by the level of experience amongst the attendees. There were only a few that were new to the investing game. In general everyone just wants to help each other get to financial freedom through Real Estate.

Looking forward to posting progress on all fronts here.

Cheers everyone, hope yall are having a great 2025 and remember small progress is PROGRESS!
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Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
Life is coming at me real fast right now. Had a series of devastating things happen personally so I am taking the next few weeks slower.
I realized I was over stretching myself just a tad, so I am reeling things in and meditating on what matters most and doing more of that. Better days to come.
0 Reply
Jason Cheramie
New to Real Estate · United States · Member since 2025 · 11 posts · 4 votes
1y
Dan your story is truly inspiring. I am approaching 40 and just now starting to explore real estate. As a land development engineer my goal is to leverage my expertise by handling the plans and permitting for raw land development. My ideal scenario is to take a percentage stake in a project that will be sold, allowing me to generate cash flow for the next investment.

I have worked on projects ranging from small to large subdivisions as well as commercial and industrial developments. My goal is to use my experience and professional licensure to establish a strong foothold in the industry. Where there is a will there is a way so I am staying determined. Keep pushing forward! 💪
1 Reply
- Daniel Ortiz de la Garza
  OP
  Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
  1y
  Quote from @Jason Cheramie:
  
  Dan your story is truly inspiring. I am approaching 40 and just now starting to explore real estate. As a land development engineer my goal is to leverage my expertise by handling the plans and permitting for raw land development. My ideal scenario is to take a percentage stake in a project that will be sold, allowing me to generate cash flow for the next investment.
  
  I have worked on projects ranging from small to large subdivisions as well as commercial and industrial developments. My goal is to use my experience and professional licensure to establish a strong foothold in the industry. Where there is a will there is a way so I am staying determined. Keep pushing forward! 💪
  
  Hey man, sorry I just realized I missed replying to this. Thanks for the kind words and encouragement. I love to hear folks getting involved with a niche market within investing as you are in regards to land development engineering on the front end of a deal.
  Cheers🙂
  0 Reply
Daniel Ortiz de la Garza
OP
Investor · Western Suburbs, IL · Member since 2015 · 109 posts · 59 votes
1y
Aside from tragedy in the last few weeks, things are still in line to get into a deal before the end of Q2 this year. Targeting Bridgeport, Pilsen, and near North side walking distance to the L, 3-4 unit.
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