Best Straight Up Chicago Investor Podcasts (2024)

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Episode 289: VA Loans, ADUs, and Turning a Funeral Home Into an Airbnb with Andrew Dorazio 1:02:11

1d ago1:02:11

1:02:11

Andrew Dorazion is a former Army officer and accomplished real estate broker, investor, and property manager! Andrew jumps right in with a cool story involving a funeral home turned short term rental! He shares tips on finding partners and structuring partnerships to help scale more quickly. Andrew drops valuable nuggets on pumping a building’s NOI…

1
Episode 288: This Is Where Interest Rates Are Going Next... 14:55

12h ago14:55

14:55

Where Are Interest Rates Heading and What's Happening in The Capital Markets? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman, Renovo Financial Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House: Flint Stone Media Copyright …

1
Episode 287: Why Your Customer Experience is Falling Short with Joey Coleman 1:08:10

5d ago1:08:10

1:08:10

Joey Coleman is a best selling author and founder of a branding firm that specializes in helping businesses retain customers and employees! Joey jumps right in by explaining the difference between customer service and customer experience. He explains the best ways to handle routine tenant check ins and disagreements with tenants all through the len…

1
Episode 286: The Chicago Investor’s Guide to Public Relations with Sabrina Wottreng 58:32

12d ago58:32

58:32

Sabrina Wottreng is a Chicago-based Publicist and a “Friend of the Pod.” Sabrina’s company specializes in the real estate sector and has helped many Chicago-area real estate teams with their public relations (PR) and communications strategies. Sabrina explains how she got started in PR and her introduction into commercial real estate. She dives int…

1
Episode 285: Diving into DSCR with Eric Workman of Renovo Financial 14:36

14d ago14:36

14:36

By Mark Ainley and Tom Shallcross

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Episode 284: Triumphs and Troubles From a Decade of Experience on Chicago’s Southeast Side with Jared Kott 1:01:56

19d ago1:01:56

1:01:56

Jared Kott returns to share the ups and downs of his real estate journey that started just over 10 years ago when he left the corporate world! Jared gets right into it by talking about the challenges of operating in C/D class neighborhoods! He shares the cold hard truth of dealing with a slip-and-fall incident at one of his properties where he was …

1
Episode 283: Container Homes: Innovative and Affordable Housing with Rory Rubin 49:25

27d ago49:25

49:25

Rory Rubin, founder of S.I. Container Builds, joins us to explain how her company’s Container Homes is a high-quality solution to current housing affordability and inventory issues! Rory starts by explaining her background in social work and the process of starting up S.I. Container Builds! She breaks down specs and pricing of container homes illus…

1
Episode 282: Decoding the Final Walkthrough: A Comprehensive Guide for Buyers and Sellers 13:36

30d ago13:36

13:36

What should I expect on the final walk through from both the buyer and seller side? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chance Badertscher, Lavelle Law Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House: Flint Stone Media Cop…

1
Episode 281: One of the First Investors to Leverage The New 5% Down Lending Product on a Successful Househack With Brendon Heneks and Sarita Scherpereel 51:50

1M ago51:50

51:50

Brendon starts by sharing his buy box and how he was ready to pounce when he found the right property. Brendon and Sarita share great insights on how to jump at opportunities when the competition is fearful. Brendon explains worrisome moments and lessons learned during the purchase of his househack both before and after closing. Brendon breaks down…

1
Episode 280: Investing in Premier Chicago Neighborhoods as a Busy Professional with David Shifrin and Rob Sikkel 52:22

1M ago52:22

52:22

David Shifrin, the doctor of Motor Row, returns with his real estate agent Rob Sikkel to discuss how he’s grown his portfolio with quality multifamily properties over the last 2 years! David starts by explaining his investing strategy and how he’s acquired 5 multifamily buildings since his last appearance on SUCI! David and Rob dive into the detail…

1
Episode 279: Best Practices For Tenant Move-Outs 14:35

1M ago14:35

14:35

By Mark Ainley and Tom Shallcross

1
Episode 278: BiggerPockets Host David Greene Gets Real On Overcoming Recent REI Adversity 1:07:37

2M ago1:07:37

1:07:37

BiggerPockets Host, Author, and Real Estate Expert, David Greene returns to Straight Up Chicago Investor and holds nothing back as he explains how he dealt with fraud in his real estate portfolio. David explains why real estate is not an end-all solution to your financse and discusses the importances of reserves and playing defense, as outlined in …

1
Episode 277: The Chicago Investor Playbook Against Pests with Janelle Iaccino 1:01:21

2M ago1:01:21

1:01:21

Janelle Iaccinio is Rose Pest Solutions’ Marketing Director and Chicago’s “Bug Girl”! Janelle starts with the history of Rose Pest Solutions which dates back to the Abraham Lincoln era! She dives deep on rats, roaches, and bedbugs including common causes and practices to control them. Janelle mixes in a couple pest horror stories and debunks pest m…

1
Episode 276: The Best Ways to Protect Your Largest Asset 13:13

2M ago13:13

13:13

By Mark Ainley and Tom Shallcross

1
Episode 275: Keys to Off-Market Real Estate Acquisitions at Scale with Chicago’s Mike Kehoe 47:46

2M ago47:46

47:46

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 s…

1
Episode 274: Leveraging AI to Optimize Real Estate Underwriting with Chicago’s Marc Rutzen 54:05

2M ago54:05

54:05

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 do…

1
Episode 273: How To Leverage an Escalation Clause to Win Deals 12:16

2M ago12:16

12:16

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.…

1
Episode 272: Procuring Over 700 Off-Market Properties with Ben Allgeyer 53:08

3M ago53:08

53:08

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 partnershi…

1
Episode 271: Exploring Some of Chicago’s Premier Neighborhoods with Vik Wadhwa 47:59

3M ago47:59

47:59

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 investmen…

1
Episode 270: It's 2024 And Your Chicago Property is Being Reassessed Again! 17:10

3M ago17:10

17:10

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 Copyri…

1
Episode 269: Tax Auctions, Break-Ins, and More with Daniel Kaufman 54:34

3M ago54:34

54:34

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…

1
Episode 268: Five Bold Predictions For Chicago Real Estate in 2024 with Jake Fugman and Mike Scanlon 1:09:14

3M ago1:09:14

1:09:14

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…

1
Episode 267: The Ins-And-Outs of Cost Segregation 17:01

3M ago17:01

17:01

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.…

1
Episode 266: Reviewing The “Bring Chicago Home” Tax and Its Implications to Housing Providers with Mike Glasser 53:19

3M ago53:19

53:19

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 impac…

1
Episode 265: An In-Depth Inspection of Chicago Buildings with George Meegan and Dean Cushing 1:04:24

4M ago1:04:24

1:04:24

George Meegan and Dean Cushing join us to share insights from several decades of experience in the building systems and inspection industry! The duo jumps right in by discussing their start in the inspection industry and giving us some inspection horror stories. George and Dean get granular on common issues with major building systems including plu…

1
Episode 264: Unlocking Zoning Secrets: Your Guide to Chicago Zoning, ADUs, and Other Essential Information 14:34

4M ago14:34

14:34

Where can I go to find all information around zoning, ADU, lot sizes and lot lines, and other essential information? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Samuel Pavlovcik, Pavlovcik Architecture Inc Link: Zoning Cheat Sheet ----------------- Production House: Flint Stone…

1
Episode 263: Buying Chicago Lots For $1 and Other Successful Strategies with Tanisha Blakemore 41:04

4M ago41:04

41:04

Tanisha kicks things off by discussing her first deal back in 2005; a 2-unit in Auburn Gresham that she purchased with 0% down! She talks about learning to be a housing provider during a time when resources were much more scarce than today. Tanisha has a couple real estate horror stories including another fire story and the US Marshals arriving at …

1
Episode 262: From FBI Agent to Hundreds of Doors In Chicago with James Williams 1:08:42

4M ago1:08:42

1:08:42

James Williams is a real estate investor, attorney, and former FBI agent who embarked on his real estate journey in the early 90s! James starts by discussing how he chose a career path which includes a period of working in the FBI, all while having real estate investing on the back of his mind. He discusses his first real estate purchase, a graysto…

1
Episode 261: Accelerate Your Expenses and Other Accounting Tips To Leverage Before 12/31 16:09

4M ago16:09

16:09

What questions should I ask my tax professional before the end of the year? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Aaron Zimmerman, Lipschultz Levin & Gray Link: Episode 52: Saving Thousands of Dollars With the Appropriate Tax Strategy and Deductions ----------------- Prod…

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Episode 260: Chicago Investors Cannot Have a Worse Day Than This, With Roman Viere 1:15:21

5M ago1:15:21

1:15:21

Roman Viere owns and operates over 1000 rentals in Chicago with the bulk of those in the Austin neighborhood. In this episode, he gives a detailed breakdown on a terrifying explosion that occurred at his 35-unit apartment building in Austin. He discusses all things from the day of the incident including arriving at the scene, speaking with the auth…

1
Episode 259: Time For Serious Chicago Investors with Sal Becovic 1:00:38

5M ago1:00:38

1:00:38

Sal Becovic returns to the show to discuss how he has continued to grow his portfolio despite the challenging market! Sal jumps right in by sharing his philosophy on acquisitions and being “rate agnostic”. He gives an extremely bullish outlook on Chicago leaving us feeling great about this special city. Sal discusses the ins and outs of his latest …

1
Episode 258: Maximize Your Savings: Unveiling the Tax Advantages of Solar Panels and Electric Vehicles 16:37

5M ago16:37

16:37

What are the tax benefits of solar panels and electric vehicles? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Michael Procaccio, Pro Financial Services Group Inc Link: Build Your Team | Straight Up Chicago Investor Podcast Link: Episode 198: 2023 Tax Strategies for Chicagoland R…

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Episode 257: The Playbook For Short-Term Rentals in Chicago with Ditron Corker 58:05

5M ago58:05

58:05

Ditron is a seasoned Short-Term Rental (STR) Investor who is teaching others how to get started and maximize profitability with STRs. Ditron shares how he got started in real estate and utilized the house hacking and rent-by-the-room strategy. He shares tremendous nuggets on finding good STR markets and typical expenses associated with setting up a…

1
Episode 256: Home Inspection Insights For Chicago Investors With Andrew Fox 52:35

5M ago52:35

52:35

Andrew kicks things off by discussing necessary skills to succeed as an entrepreneur in Real Estate. He talks about the value of a building inspection even if the property will be rehabbed. Andrew clears the air on the need for auxiliary inspections such as radon, asbestos, and sewer scopes. Andrew drops golden nuggets on questions that investors s…

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Episode 255: Exploring Lending Options for Self-Employed Individuals with Eric Workman 14:53

5M ago14:53

14:53

What are my lending options if I do not have a W2? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman, Renovo Financial Link: Episode 19: Top 10 Mistakes We See From Chicago Investors - with Eric Workman of Renovo Financial (Part 2) ----------------- Production House: Fli…

1
Episode 254: Becoming a Straight Up Chicago Investor With Life Lessons From the Military with Edgar Barbosa 47:43

6M ago47:43

47:43

Edgar Barbosa is an investor and realtor with a focus on helping clients get into REI to start their wealth building journey! It’s clear the Military is not for the weak, and Edgar speaks to the lessons learned during his time served along with how he applies those teachings to his current lifestyle and investments. He dives into his first househac…

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Episode 253: Purchasing 1,000 Chicagoland Properties Through Extensive Marketing with Jeff Nydegger 1:07:24

6M ago1:07:24

1:07:24

Jeff Nydegger has over 17 years of real estate experience including over 1,000 homes bought and repositioned in Chicagoland! Jeff jumps right in by sharing how skill sets built in the Military have served him in his REI ventures. He dives deep into his rough start in real estate including the mental resilience and grit it took to overcome the adver…

1
Episode 252: Conventional Financing vs DSCR Loans 8:30

6M ago8:30

8:30

What are the pros/cons between conventional financing and DSCR loans? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman, Renovo Financial Link: Episode 19: Top 10 Mistakes We See From Chicago Investors - with Eric Workman of Renovo Financial (Part 2) ----------------- Pr…

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Episode 251: Powerful Networking and Property Management Insights with Bob Hansen 51:19

6M ago51:19

51:19

Bob is a successful realtor and investor with a focus on House Hacking to help her clients build investment portfolios! Bob kicks things off by talking about the power of networking and gives tips on developing networking skills. He discusses his vast experience working with property managers and housing providers along with insights on improving m…

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This Week in PM 4: Is It the Right Time You Sell Your Property Management Company? 54:46

6M ago54:46

54:46

In this episode, Jock McNeill, VP of Acquisitions at Pure Property Management, joins us to discuss his company’s journey in acquiring several of the notable property management companies that you may have heard about while participating in the annual NARPM conference. We also cover what Pure looks for and the process they follow when acquiring all …

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Episode 250: Unlocking Success by Establishing a Strong Focus in Chicago Real Estate with Jonathan Klemm 55:18

6M ago55:18

55:18

Chicago General Contractor and return guest Jonathan Klemm provides insight on successes and improvements made to his Business and Investments since his last appearance! Jonathan kicks things off with tremendous insights on Chicago construction including permits, renovations, new construction, and lessons learned. He discusses his recent acquisitio…

1
Episode 249: Fannie Mae's Departure From Needing 25% Down on 2-4 Units 12:19

6M ago12:19

12:19

What are the new changes to owner-occupied conventional lending and how can Chicago investors take advantage of them? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chris Puleo, Puleo Group Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Pul…

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Episode 248: Early Investing Pitfalls and Tremendous Lessons Learned in Chicago’s South Suburbs with Alex Fenske 1:01:30

6M ago1:01:30

1:01:30

Alex shares how he got interested in real estate investing and bought into “guru” advice which did NOT serve him well! He dives deep into the compounding mistakes he made as a new investor including lack of focus and education and working with an inexperienced team. Alex discusses raising and losing private capital which lead to intense stress, dif…

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Episode 247: Strategic House Hacking in Chicago’s West Town Neighborhood with Sarita Scherpereel 58:19

7M ago58:19

58:19

Sarita Scherpereel is a successful realtor and investor with a focus on House Hacking to help her clients build investment portfolios! Sarita jumps right in by sharing how she got started in real estate, built her business, and chose House Hacking as an area of focus. She shares tremendous value on how to analyze House Hacks and debunks several myt…

1
Episode 246: How to Get Reimbursed For Damages From Recent Chicago Flooding 10:45

7M ago10:45

10:45

How can I get reimbursed for damages that occurred to my property from the recent Chicago floods? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Jason Wagner, Greystone Realty Link: DisasterAssistance.gov Link: Disaster Loan Assistance Link: SUCI Episode 224: Expert Insights On C…

1
Episode 245: Insights to Successful Short-Term Rental Investments with JD Modrak 55:28

7M ago55:28

55:28

JD shares his real estate beginnings, including his purchase of a multi-family building with a VA loan. He dives into Short-Term Rentals (STRs) including income, expenses, and how those compare to traditional rentals. JD gets granular on STR pricing, occupancy, turn-over costs, and optimizing profitability. He drops golden nuggets on common mistake…

1
Episode 244: Real Estate Tax Advantages, Short Term Rentals, and Branding, With Ryan Bakke 57:46

7M ago57:46

57:46

Ryan Bakke is a CPA, real estate investor, and coach who is helping others build wealth via real estate and tax strategy! Ryan starts by explaining the value a Tax Strategist brings and common mistakes on tax returns. He dives into the power of short-term rentals (STRs), their tax advantages, and how to underwrite STR investments. Ryan shares his p…

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Episode 243: A New Chicago Lending Option to Assist With Rehab Funding 14:30

7M ago14:30

14:30

What is this new lending option that could finance my rehab funds? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Perry Farella, First Community Mortgage ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.…

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Episode 242: From Rookie Status to Seasoned House Hacker, Flipper, and BRRRR Conductor on Chicago’s Northwest Side with Manny Escarpita 46:43

7M ago46:43

46:43

Manny Escarpita is a young Chicago Real Estate Investor and Licensed General Contractor who has built up an impressive real estate portfolio since starting in 2019! Manny leads by explaining the hungry mindset he cultivated when starting in real estate and the lessons learned on his first deal. After discussing his first couple house hacks, he brea…

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Episode 241: Game-Changing Appraisal Insights with Steve Zidek 56:02

8M ago56:02

56:02

Steve Zidek has nearly two decades of real estate experience as a broker and appraiser! Steve kicks off with how he got into the appraising business and breaks down the appraisal process! He gets granular on adjustments that may or may not be considered and speaks to the “art” components of an appraisal. Steve discusses how income factors into resi…

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