Straight Up Chicago Investor

Straight Up Chicago Investor

Business EN ↓ 468 episodes

Are you a real estate investor in Chicago or someone looking to invest in the Chicagoland Market? If so, this podcast is for you! We break down the neighborhoods, different sides of the city, and surrounding suburbs so you can understand the uniqueness of investing in Chicago real estate. The hosts and guests are Chicago investors and Property Managers who are making it happen in and around the Windy City. We share information, winning strategies, obstacles, success stories, and most importantly, lessons learned. If you are looking for ground level information and want to learn what has worked...

Author

Straight Up Chicago Investor

Category

Business

Latest episode

Jul 9, 2026

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Episodes

Episode 93: Straight-Up Tuesday Tip 13 - Sharad Mehta Answers "How do I leverage processes and automation to scale my REI business?" 05.10.2021

How do I leverage processes and automation to scale my REI business? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Sharad Mehta of REsimpli ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Episode 92: From Student/Tenant to 1,200 Units in Hyde Park 30.09.2021

What's your unit goal? Is it 20...maybe 50? Well today's guest explains how his company amassed 1200 units solely in Hyde Park, (not including their north side portfolio). Nick Hollenkamp drops street-level advice on the different corridors of Hyde Park along with his ten year forecast for the neighborhood.  Nick provides great soundbits on why you should never fully give up on a deal, which pocke...

Episode 91: It's Your Team That Will Make You Millions in Chicago - Brian Lignelli Knows From Experience 23.09.2021

You cannot grow without adequate funding. When it comes to private funds, there are so many questions asked as a new investor. Brian Lignelli takes the time today to talk about how his company, Continuum Capital Funding can put it's partners in a position to scale and grow as well as how to prepare to work with them. He also hits on some of the various neighborhood associations he's a part of and...

Episode 90: Straight-Up Tuesday Tip 12 - Eric Workman Answers "What factors go into determining commercial financing?" 21.09.2021

What factors go into determining commercial financing? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman of Renovo Financial ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Episode 89: My Tenants Stole My Car; The Chicago House Hack from Hell with Joey Pochinskas 16.09.2021

In episode 85, David Geen said househacking is the Stephen Curry cheat code of real estate. Many folks agree and have leveraged this strategy to kick off successful REI careers. However, there are real risks that arise the moment you become a housing provider.  Today's guest, Joey Poshinskas, is an extremely resilient househacker who persevered through numerous obstacles to stabilize his building....

Episode 88: You Can't Get Any More Chicago Than This - First-Generation American Sal Becovic and his 2,000 Rogers Park Units 09.09.2021

Like many families in Chicago, Sal's family came from the old world and settled in a turbulent part of the city at a turbulent time. As he's now standing on the shoulders of what his parents initially organized, he's building it farther than ever expected. Sal's story is amazing, his advice is timely, and his passion is contagious. Listen to today's episode with Sal Becovic. Connect with Mark and...

Episode 87: Straight Up Tuesday Tip 11 - Eric Workman Answers "What steps can I take to maximize my appraisal?" 07.09.2021

What steps can I take to maximize my appraisal? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman of Renovo Financial ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Episode 86: Self Storage - No Toilets or Tenants - with Chicag Expert Fernando Angelucci 02.09.2021

Fernando Angelucci has spent the last decade becoming one of the largest wholesalers in the Chicagoland area. Fernando successfully scaled his wholesaling business to a goliath and used the same skill sets and systems to establish and grow his self storage portfolio. In today's episode, Fernando breaks down why he prefers self storage over multifamily investing, what you should be looking for in a...

Episode 85: Bigger Pockets Host and Expert Investor David Greene Visits Straight Up Chicago Investor 26.08.2021

Nationally-recognized real estate rockstar David Greene of Bigger Pockets and Keller Williams holds nothing back! David provides his thoughts on the BRRRR strategy and dissuades the myths around equity as a cushion. David also covers the buyer/investor relationship, houssehacking as a cheat code, and why you need to start pushing over dominos to build your empire. Please enjoy today's episode and...

Episode 84: Straight Up Tuesday Tip 10 - John Warren Answers "How can I put my best foot forward when making offers and how can I show experienced agents that I am serious?" 24.08.2021

How can I put my best foot forward when making offers and how can I show experienced agents that I am serious? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: John Warren of Second City Real Estate ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Episode 83: How to Acquire, Fund, and Develop Distressed Properties in Chicago 19.08.2021

Malcolm Gladwell popularized the idea that it takes 10,000 hours to master something. Well, if that's the case, Mike Olszewski has likely mastered his craft several times over. To date, he has sold over 17,500 REO properties, developed properties and has even begun his own private lending business. Today, you get to learn the process of acquiring, rehabbing and selling REO properties from a master...

Episode 82: Flipping Houses in Chicago's Northwest Side 12.08.2021

Knowing a couple neighborhoods intimately is better than a hundred superficially. That's exactly what the Property People did in Chicago's northwest neighborhood. It's how they know how deep they can dig a basement out and how much value they'll add. What certain features are expected and what can they pass on? Greg and Jenny are a rockstar duo that have grown tremendously and have even more ambit...

Episode 81: Straight Up Tuesday Tip 9 - Rosario Terracciano Answers "What is ClickInvest and why should I care?" 10.08.2021

What is ClickInvest and why should I care? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Rosario Terracciano of Clickinvest ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Episode 80: Real Estate Investing 101 in Naperville with Josh Mitchell 05.08.2021

From the downtown riverwalk, to larger lots and Suburban living, Naperville is a diverse market drenched with opportunity. Today's guest, Josh Mitchell, has carved out his niche as the go to guy in the area, acting as both an investor and a broker for Re/Max in Naperville. In this episode, Josh answers some FAQs for people thinking about going down a similar career trajectory and explains the nuan...

Episode 79: "I Got A Guy" - Keys to Building a Strong Chicago Network with Gary Davidson 29.07.2021

All the nuggets you've learned from previous episodes won't add up to squat if you do not have the appropriate team in place. So how do you build that successful team? Today's guest, Gary Davidson, is not only a rock star attorney, but he is the definition of a go-giver. In today's episode you will learn how asking the question "how can I add value to person X?" can solidify your network and prope...

Episode 78: Straight Up Tuesday Tip 8 - Chance Badertscher Answers "What are the steps and my responsibilities as an investor to get from attorney review to the closing table?" 27.07.2021

What are the steps and my responsibilities as an investor to get from attorney review to the closing table? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chance Badertscher of Lavelle Law ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Episode 77: Screening, Operating, And Understanding Chicago's West Side 22.07.2021

Roman Viere manages and operates over 900 apartment units, and the majority of these units are in Austin. Austin is geographically Chicago's largest neighborhood and offers everything from a 9-hole golf course to struggling store fronts. It takes a hands-on approach to analyze, screen and operate in a neighborhood like Austin, and Roman provides tactical insights and street-level knowledge useful...

Episode 76: Big Business Processes Make a Powerful Small Business with Jonathan Klemm 15.07.2021

Like many real estate professionals, Jonathan Klemm transitioned from a W-2; what is remarkable about him is his background working with Walsh Construction, which is one of Chicago's largest construction and contraction companies. Jonathan has taken everything he learned about managing large scale projects and applied it to smaller, investor focused projects. Listen in as Jonathan explains his pro...

Episode 75: Straight Up Tuesday Tip 7 - Rosario Terracciano Answers "What are proactive steps to ensure I'm ready to pull the trigger when the right property presents itself?" 13.07.2021

What are proactive steps to ensure I'm ready to pull the trigger when the right property presents itself? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Rosario Terracciano of Clickinvest ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Episode 74: Investing for Intergenerational Wealth in Evanston with Jaimie Steinher of Essex Realty 08.07.2021

With the Lake, a world-class University, and a plethora of transportation, Evanston is an extremely attractive and diverse marketplace for many investors. Jaimie Steinher of Essex Realty exclusively covers Evanston, and provides on the ground insights to help you navigate the different pockets of the city. Jamie lays out cap rates, average rents, and tenant expectations in an episode packed with t...

Episode 73: Understanding the Cost and Maintenance of Chicago Porches with Mr. Porch 01.07.2021

For many Chicagoans, the porch has been the focal point of countless memorable times. Since Covid, the importance of "outdoor spaces" in real estate has re-emerged as a priority for plenty of homebuyers, too. But how many investors know how to evaluate the build quality of a property with a porch? And what's the process like when wanting to add a back porch to an existing property? How do you work...

Episode 72: Straight Up Tuesday Tip 6 - John Warren Answers "What are some common mistakes I can look to avoid when calculating my after repair value and proposed rents?" 29.06.2021

What are some common mistakes I can look to avoid when calculating my after repair value and proposed rents? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: John Warren of SecondCity ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Episode 71: The Illinois REALTORS' Advocacy for Housing Providers and Why Chicagoland Investors Should Care 24.06.2021

We all know about the numerous laws either being proposed or already enacted affecting housing providers and investors. Groups like the Illinois Realtors Association, the NBOA, the CAR and others are working everyday to keep laws fair and protect people. Our guest today, Gideon Blustein, is the director of member outreach for the Illinois REALTORS and talks us through some of the current issues at...

Episode 70: What's Around the Corner in the Chicago Real Estate Market with Ryan Smith 17.06.2021

Ryan Smith is not an optimist, but a realist. With a stark numbers-based opinion, Ryan provides his thoughts on Chicago's housing market, the strength and the validity of the recent appreciation, and how long it may take to get through upcoming foreclosure inventory. We've had Ryan on here before (Episode 28), but last time it was too good of a conversation so we had to bring him back. Listen in a...

Episode 69: Straight Up Tuesday Tip 5 - Rosario Terracciano Answers "How can I make my offer more attractive in this hot market?" 15.06.2021

How can I make my offer more attractive in this hot market? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Rosario Terracciano of Clickinvest ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

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