Walking off a cliff? Hola, from Chicago!

[Jovim Ventura]

Hello,

I'm a 34 year old Filipino American Chicago Entrepreneur. I stress this because many Filipinos are risk adverse. Filipino parents: "Go to school, find a good job, work 16 hours a day, retire at 65." I suscribe to calculated risk taking and finding opportunities. So my curiousty led me to building wealth > Entrepreneurship > Real Estate > Bigger Pockets.

Loving the vibe/culture here on BiggerPockets. I've been trolling and soaking up all the information on here and I must say this is a very serious community. I've read many books, but the massive value packaged into my cell phone is extremely powerful. Im in the car typing this as my wife is Christmas shopping on North and Clybourn (I do mine on Amazon). Parking here is rough and Chicagoans can be a little mean Christmas Shopping.

Little background on me. I quit my day job in 2007 and started my own business (printing). Through the most challenging 3 years of my life (I wanted to quit 3 times), I finally got my business to run and grow. This year, I just built another business to pay off my wife's college loans (got married last year!) and it has been a much easier process the 2nd time around. We were aggressive and are close to paying off her $110k+ loans in a little over a year. (You smarter people probably would have taken that money and used it to buy rentals to pay off the loans... but that's why I'm here).

Now that the loans are going to evaporate soon, we are planning for the next step which is building "passive" viehcles and tax shelters through real estate and dividends. The former being our first priority in the next 4 years. I am a huge advocate for cashflow and having it pay for expenses + a responsibly fun life (we love to experience new things). Kids may be a few years away too, but we want to set up a strong foundation before we get "caught up in life".

I am happy to be part of this community because when I first started my business I didn't have any mentors, just a tireless work ethic and a huge desire to NOT fail (and prove to my Filipino parents I wasn't crazy leaving my stable day job). I believe mistakes are part of learning, but with an experienced person, I could have saved 3 years of expirements. That's why I'm here. My 2nd business was easier because I didn't make the same mistakes. Now that Im a little older... and only a tad bit wiser, I know it's smarter to find a vet(s) to learn from. I admire a lot of people on this forum.

I know this is long, but real estate is an itch I have been meaning to scratch and usually when I have a constant itch for more than a year (Ive had it for 9 years), I have to do something about it. The benefits and wealth building potential are just too great. I like reading numbers, I like making deals, I am an operational nut, but I know my weaknesses and I need a swift kick in the butt to start. I'm not a handy man other than the basic Ikea dresser assembly. Don't tell my wife because she still believes Im this generation's Bob Villa.

My 4 year plan for us was to purchase cashflowing properties using "Turnkey" partners to offset our first future home and all living expenses. I know, I hate the term too, I learned you make money when you buy (equity) but it looks like this is the best fit for how our lives are operating now. Only thing is, It's all on Section 8 neighborhoods in Chicago and I've heard some challenges about turnover. Naturally, higher return, higher risk.

I'm naturally a curious person and a sponge for information, so do you suggest going into the root and basics of real estate instead of doing the Turnkey route? Learn every process from analyzing a good deal, bidding, building a team, surveying, negotiating, closing, fixing, selling, etc?

Are we going in the right direction? Is there a better way? Am I walking towards the edge of a cliff? Anyone care to hold our hands and lead us in a better direction? I like to add value to people's lives as well, so hopefully any guidance can be a mutually beneficial experience. I place a a ton of value on great information. Maybe split profits on a deal or two? Maybe some lawn signs, banners, business cards, brochure printing for your real estate business?

Thanks in advance Bigger Pockets family! Looking forward to one day being of value for the next generation of investors as well.

Jovim