

Straight Up Chicago Investor
Straight Up Chicago Investor
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 and not worked in Chicago, you are in the right place.
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 and not worked in Chicago, you are in the right place.
Episodes
Mentioned books

Feb 8, 2024 • 48min
Episode 275: Keys to Off-Market Real Estate Acquisitions at Scale with Chicago's Mike Kehoe
Mike Kehoe is an experienced investor and entrepreneur who has created and sold multiple technology companies! He joins us to explain how his latest company is thriving in off-market real estate acquisitions and dispositions. Mike explains how he chose a real estate market to focus on and the grind of driving for dollars to find opportunities! He shares great tips on how to engage potential sellers of off-market real estate including the strategies his team has had the most success with. He discusses the importance of core values and building a quality team that aligns with those values. Mike closes with motivating words on cultivating a growth mindset to become the best version of yourself! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Mike Kehoe, VentureStack | Email Mike (Mike@Venture-Stack.com) Link: Mike Kehoe's LinkedIn Link: Tenant Radon Protection Act 2024 Link: SUCI Ep 253 - Jeff Nydegger Link: SUCI Ep 86 - Fernando Angelucci Link: Traction (Book Recommendation) ----------------- Guest Questions 02:51 Housing Provider Tip - Ensure you're up to date on the new Security Deposit laws. 04:00 Intro to our guest, Mike Kehoe! 08:28 Picking a market to invest in. 11:42 Driving for Dollars! 13:23 Engaging Sellers! 19:31 Growing a quality team. 27:24 Common mistakes when scaling and establishing core values. 32:20 Bottlenecks in Mike's business. 39:35 Mike's focus on personal growth! 43:25 What is Mike's competitive advantage? 43:44 One piece of advice for new investors. 43:54 What do you do for fun? 44:04 Good book, podcast, or self development activity that you would recommend? 44:37 Local Network Recommendation? 45:04 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Feb 1, 2024 • 54min
Episode 274: Leveraging AI to Optimize Real Estate Underwriting with Chicago's Marc Rutzen
Marc Rutzen is an experienced investor with over 12 years of real estate and technology experience. He joins the guys to explain the power of knowing your rental comps and how HelloData can help accelerate that knowledge. Marc discusses his start in market analysis along with the creation of his analytics startup which he sold in 2019. He breaks down the creation and value proposition of HelloData. He explains how HelloData is able to efficiently gather and scrub data to quantify the value of real estate. To close the show, Marc provides us his outlook on technology in general and the Chicago real estate market! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Marc Rutzen, HelloData Link: SUCI Ep 68 - Lee Kiser Link: The Lean Startup (Book Recommendation) Link: TLDR in Tech Newsletter ----------------- Guest Questions 02:36 Housing Provider Tip - Ensure you're up to date on the new Security Deposit laws. 04:21 Intro to our guest, Marc Rutzen. 07:53 Marc's start in market analysis. 17:10 Horror stories of starting and selling a business! 19:37 The creation of HelloData! 23:49 HelloData's targeted end clients. 29:18 HelloData's value proposition to investors. 39:33 Marc's outlook on technology! 45:05 Marc's outlook on the Chicago Real Estate Market! 46:32 What is Marc's competitive advantage? 47:07 One piece of advice for new investors. 47:47 What do you do for fun? 48:17 Good book, podcast, or self development activity that you would recommend? 49:22 Local Network Recommendation? 50:05 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Jan 30, 2024 • 12min
Episode 273: How To Leverage an Escalation Clause to Win Deals
What is an escalation clause and how can investors utilize it? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Sarita Scherpereel, Sarita Sells ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Jan 25, 2024 • 53min
Episode 272: Procuring Over 700 Off-Market Properties with Ben Allgeyer
Ben Allgeyer has flipped over 200 properties and wholesaled over 500 properties! Ben talks about his brief stint in corporate America before leaving to pursue a career in Real Estate. He discusses the early days of making cold calls and door knocking for lead generation. Ben dives into building a team and vetting candidates for potential partnerships. He touches on his team's disposition strategy and the importance of protecting relationships with partners. Throughout the show, Ben emphasizes how critical it is to put in the work and master your craft to obtain success in real estate and in any other business! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Ben Allgeyer, Elite Ventures | Ben's Instagram (@BenAllgeyer) Link: Mindvalley Link: Tim Herriage (@TimHerriage on Instagram) ----------------- Guest Questions 03:23 Housing Provider Tip - Ensure you are using the new Chicago lease! 03:49 Intro to our guest, Ben Allgeyer! 12:43 Ben's jump into real estate! 17:20 How to find leads. 22:15 Ben's deals gone wrong! 25:18 Hiring to build a team. 30:17 Top lists for landing leads! 32:41 Ben's disposition strategy. 36:11 Vetting potential partnerships! 39:17 Capital partners to grow a business. 43:00 How to find businesses to purchase. 46:02 Ben's lead generation course! 47:58 What is Ben's competitive advantage? 48:32 One piece of advice for new investors. 49:03 What do you do for fun? 49:21 Good book, podcast, or self development activity that you would recommend? 50:06 Local Network Recommendation? 50:38 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Jan 18, 2024 • 48min
Episode 271: Exploring Some of Chicago's Premier Neighborhoods with Vik Wadhwa
Vik Wadhwa is a top producing real estate broker with a focus on architecture and modern design in Chicago's Premier Neighborhoods! Vik shares his start in real estate back in 2006 and how he's been able to grow his business to become a top producing broker. Vik gets granular on Lincoln Park; defining the boundaries, desirable blocks, and investment opportunities in the neighborhood. He provides insight on West Town including the differences between the different pockets of sub-neighborhoods. The West Loop and reassessed property tax bills are also discussed. In this episode, Vik demonstrates his deep knowledge of the neighborhoods he works and emphasizes the importance of knowing your craft to be successful! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Vik Wadhwa, Modern Homes Chicago Link: Katmerka Ramic (Network Referral) Link: Eric Flanagan (Network Referral) Link: Atomic Habits (Book Recommendation) ----------------- Guest Questions 02:36 Housing Provider Tip - Ensure that communication with tenants is kept professional! 04:10 Intro to our guest, Vik Wadhwa! 07:44 Changing to Real Estate as a Career Path! 11:44 The 101 of Lincoln Park! 19:37 Getting listings in Lincoln Park and other higher price point areas. 21:26 Breaking down West Town! 24:47 Pricing across West Town. 28:00 The Rise of the West Loop! 30:33 Opportunities west of the United Center. 35:55 Forecasting Reassessed Property Values and Tax Bill. 38:05 The Real Estate Brokerage Industry and Potential Changes! 40:58 Vik's outlook on Chicago! 43:14 What is Vik's competitive advantage? 43:44 One piece of advice for new investors. 44:10 What do you do for fun? 44:31 Good book, podcast, or self development activity that you would recommend? 44:55 Local Network Recommendation? 45:26 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Jan 16, 2024 • 17min
Episode 270: It's 2024 And Your Chicago Property is Being Reassessed Again!
What do investors need to be aware of with the 2024 property tax reassessments? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Andrea Raila, Raila & Associates Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Jan 11, 2024 • 55min
Episode 269: Tax Auctions, Break-Ins, and More with Daniel Kaufman
Daniel Kaufman is an attorney with over a decade of vast experience representing real estate developers with transactions, as well as litigation, with a lot of practice involving the foreclosure auction! Daniel is also an investor who purchases at the tax auction for himself, using the assistance of another attorney who specializes in that specific legal work. Daniel kicks things off by discussing his start in real estate where he served as attorney on tax auction properties! He shares a great story on his first deal which was a 3-flat in the United Center neighborhood. He dives deep on working with the City during renovations and tells us about his current single family home deconversion. Daniel drops great nuggets on sourcing deals and grinding to learn your market to give you a competitive edge! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Daniel Kaufman, D. Kaufman Law Link: Outliers (Book Recommendation) Link: The Compound (Podcast Recommendation) Link: James Sheehan (Network Referral) ----------------- Guest Questions 03:31 Housing Provider Tip: Routinely check your vacant properties even if vacancy is temporary. 04:19 Intro to our guest, Daniel Kaufman! 07:11 Starting off in real estate with tax auction properties! 11:05 Bank-owned properties and Daniel's United Center 3-flat story! 19:07 Tax auction properties. 23:28 Daniel's next project in the United Center neighborhood! 25:50 Obtaining plans and permits and working with the City. 31:27 Sourcing deals. 35:02 Daniel's SFH deconversion! 41:49 Daniel's outlook on Chicago Real Estate. 47:27 What is Daniel's competitive advantage? 47:51 One piece of advice for new investors. 48:29 What do you do for fun? 48:50 Good book, podcast, or self development activity that you would recommend? 51:09 Local Network Recommendation? 51:26 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Jan 4, 2024 • 1h 9min
Episode 268: Five Bold Predictions For Chicago Real Estate in 2024 with Jake Fugman and Mike Scanlon
Jake Fugman and Mike Scanlon, leaders of The Axon Group, return to provide Five Bold Predictions on the 2024 Real Estate Market! We kick things off with a hot topic; what will interest rates do in 2024?! Jake and Mike weigh in on the asset class and neighborhoods positioned for big time growth in 2024. For turn-key, low maintenance investments, the group discusses areas with great opportunities for condo investments. Lastly, Jake and Mike discuss where cap rates are headed and sectors of commercial real estate that may be in trouble. As usual, Jake and Mike bring tremendous value and insights to give Chicago Investors a competitive edge! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Jake Fugman & Mike Scanlon of The Axon Group Link: SUCI Episode 200: Which Chicago Neighborhoods are Hot and Which are Not? Link: Episode 138: Straight Up Tues Tip 28 - Mike Scanlon Talks Through How He Sourced an Off Market Househack Deal Link: The Bank On Yourself Revolution (Book Recommendation) Link: Crushing It in Apartments and Commercial Real Estate (Book Recommendation) Link: Aparicio Law (Attorney Recommendation) ----------------- Guest Questions 02:33 Housing Provider Tip: Provide tenants with a credit reporting service to help them build their credit. 03:22 Intro to our guests, Jake Fugman and Mike Scanlon. 07:03 Bold Prediction #1: Interest Rates in 2024! 15:09 Bold Prediction #2: Asset class to appreciate at least 10% in value! 21:25 Bold Prediction #3: Neighborhoods positioned to boom in value! 28:07 Bold Prediction #4: Future of downtown condo prices! 37:18 Bold Prediction #5: Where are multifamily cap rates heading? 51:46 Jake's and Mike's motivation to be thought-leaders in Chicago REI! 55:37 What is Jake's and Mike's competitive advantage? 57:23 One piece of advice for new investors. 59:10 What do you do for fun? 62:20 Good book, podcast, or self development activity that you would recommend? 63:51 Local Network Recommendation? 65:28 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Jan 2, 2024 • 17min
Episode 267: The Ins-And-Outs of Cost Segregation
What do investors need to know regarding cost segregation? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Brenten Blakeman, Tanigble Property Tax Methods Link: Build Your Team ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Dec 28, 2023 • 53min
Episode 266: Reviewing The "Bring Chicago Home" Tax and Its Implications to Housing Providers with Mike Glasser
We welcome Mike Glasser back to inform us on the "Mansion" Tax and other Housing Provider legislative topics! Mike dives right in by explaining the proposed "Bring Chicago Home" Ordinance (a.k.a. "Mansion" Tax) and its impact on Chicago's economy. He explains the intent of the proposed ordinance and reasoning for why it will end up negatively impacting not only the "rich", but also Housing Providers, Tenants, and normal Property Owners. Housing Providers will need to increase revenue which primarily comes through rental income to offset increased operating costs that they cannot control. As usual, Mike brings tremendous value and advocacy for Chicago Housing Providers on today's show. If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Mike Glasser, Neighborhood Building Owners Alliance (NBOA) Link: NBOA Affiliates Page Link: Michael Zink (Network Referral) ----------------- Guest Questions 02:35 Housing Provider Tip: Be prepared with a checklist when starting ownership or management of a new property. 05:00 Intro to our guest, Mike Glasser. 10:23 Mansion Tax and other upcoming challenges for Housing Providers. 32:20 What can Housing Providers do to prevent the Mansion Tax? 34:34 Evanston's Landlord and Tenant Ordinance. 41:14 Mike's advice on how to get involved in Housing Provider Advocacy! 45:21 What is Mike's competitive advantage? 46:09 One piece of advice for new investors. 47:27 What do you do for fun? 47:44 Good book, podcast, or self development activity that you would recommend? 48:40 Local Network Recommendation? 49:41 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.


