Best Straight Up Chicago Investor Podcasts (2024)

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Episode 310: Guidelines Investors Can Utilize To Estimate Rehab Costs 12:51

1h ago12:51

12:51

What Are Some High-Level Guidelines Chicago Investors Can Leverage to Estimate Rehab Costs? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Jonathan Klemm, Quality Builders Link: Episode 76: Big Business Processes Make a Powerful Small Business with Jonathan Klemm ----------------…

1
Unexpected Encounters 51:18

44m ago51:18

51:18

Join Jamie and Terrence for a special episode where they read listener stories and go to Reddit for some wild encounters. In the first segment, Jamie reads stories submitted by listeners, recounting tales of shocking discoveries during showings, an agent’s determination to do a showing despite being terribly hungover and experiencing an untimely pe…

1
Episode 309: How To Build a Community of Experts and Influencers with Tony Arce 56:55

2h ago56:55

56:55

Tony Arce and his Team at The Face of Community & Business provide a media platform for leaders in business to connect, teach, and grow together. Tony starts by sharing how he discovered his passion for media and creating human-to-human connections not only in his personal life but in business. He explains how this passion sparked the idea of creat…

1
Episode 308: D1 Athlete’s Journey: From Immigrant to Finance Mentor with Alex Filin 56:09

2d ago56:09

56:09

Alex Filin is a seasoned Loan Office, Coach, and Investor with over $385 Million in funded loans! Alex shares his upbringing as an immigrant in America, experiences that cultivated grit, and his journey to becoming a D1 football player! He discusses his successful career shift to mortgage lending where he closed $95 million in funded loans in the f…

1
Episode 307: Steps For Investors To Take During the Tax Off-Season 13:56

4d ago13:56

13:56

What Steps Should Investors Take During the Tax-Offseason to Minimize Tax Liability? 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 ----------------- Production House: …

1
Walkthrough Woes Ft Ted Kuhlmann 59:09

18d ago59:09

59:09

Ted Kuhlmann, an experienced real estate agent of 20+ years, shares his entertaining and crazy real estate stories and discusses the importance of work-life balance, especially after recently having a child. This episode is filled with engaging stories, advice for new real estate agents, and the usual fun banter among the hosts, Jamie and Terrence.…

1
Episode 306: Drugs, Death, and Big Mistakes Never Spoken Of with Mark Ainley 1:07:08

9d ago1:07:08

1:07:08

The tables turn this week as Mark Ainley gets interviewed by Tom Shallcross, returning the favor from Episode 235 (episode link in show notes)! Tom starts by asking Mark about his childhood and upbringing; spoiler alert - there is mention of Mark’s frosted-tips phase while vacationing in Mexico!! Mark breaks down his start in real estate, the genes…

1
Episode 305: Three Chicago Pockets No One is Talking About With Sarita Scherpereel and Megan Osberger 46:17

16d ago46:17

46:17

Sarita Scherpereel and Megan Osberger join us to discuss three overlooked neighborhoods and why they anticipate tremendous growth in those areas! Sarita and Megan start by discussing how a new Metra stop in the Andersonville and Edgewater neighborhoods is going to take that area to the next level! They break down the new CTA green line stop at Dame…

1
Episode 304: What Are the Different Items Holding Up Closings in 2024? 13:12

18d ago13:12

13:12

How are local Chicago real estate transactions different than they were a year ago? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Bibek Das, Das Law ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.…

1
Closings and Cocaine Ft Hayley Westhoff 49:28

22d ago49:28

49:28

In this episode, Jamie and Terrence welcome Hayley Westhoff to the show. They share hilarious and shocking real estate stories, from discovering surprises during showings to the pitfalls of dealing with difficult clients. Listeners are in for an informative yet entertaining discussion on the challenges and joys of the real estate industry. Plus, Ha…

1
Episode 303: How Two Teachers Found Financial Independence Through Real Estate with Blaine and Lily Kosek 1:10:40

1M ago1:10:40

1:10:40

Want to hear an inspirational story about two teachers leaving their W2 and amassing over 20 rental units over a few short years? If so, then this show is for you! Blaine and Lily talk about their decision to leave their jobs as educators to become full-time real estate agents and investors! They discuss specific suburb markets that they target alo…

1
Episode 302: Strategies for Acquiring Off Market Real Estate with Dain Laverty 59:52

1M ago59:52

59:52

Dain Laverty is a Managing Partner of Property Pals; a company that specializes in acquiring off market real estate through a variety of methods! Dain shares his start in real estate including his first deal on Chicago’s south side sourced from Craigslist! He discusses finding his business partner and how he identified their complementary skill set…

1
Episode 301: How to Maximize Showing Value by Professionally Decluttering With Karen Welch 10:27

1M ago10:27

10:27

What is the easiest way to declutter a home to maximize it's showing value? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Karen Welch, Moovers Chicago Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House: Flint Stone Media Copyright of S…

1
Investment Properties Ft Mark Ainley and Tom Shallcross of The Straight Up Chicago Investor Podcast 1:02:54

1M ago1:02:54

1:02:54

In this episode of RealTea Chicago, Jamie and Terrence interview Mark Ainley and Tom Shallcross of The Straight Up Chicago Investor podcast. They discuss a variety of intriguing and ridiculous stories related to Chicago real estate, flipping properties, and property management. From sharing details about break-ins and evictions to recounting wild t…

1
Episode 300: 300th Episode Celebration - Answers To Burning REI Questions Amongst Chicago Investors with Mark and Tom 52:19

1M ago52:19

52:19

Straight Up Chicago Investor Podcast celebrates its 300th Episode! To celebrate the huge milestone, Mark and Tom answer questions from guests on all things Chicago REI! If you enjoy all the value the SUCI podcast brings, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChi…

1
Episode 299: The Top 25 Lists to Find Motivated Sellers with DealMachine’s David Lecko 42:36

2M ago42:36

42:36

David Lecko is an investor and CEO of DealMachine; a software that helps investors streamline the process of off-market property lead generation! David starts by discussing the genesis of DealMachine He does a deep dive on the 25 motivated seller lists that can be found on DealMachine or other applications. He emphasizes the importance of being per…

1
Urban Legend Ft Crystal Tran 53:02

2M ago53:02

53:02

In this enthralling episode of RealTea Chicago, we dive deep with Crystal Tran, a seasoned real estate professional, as she shares her wealth of stories from the trenches of Chicago real estate. From navigating the complexities of divorcing sellers to her personal journey of growth within the industry, Crystal offers a rare glimpse into the emotion…

1
Episode 298: How To Fund Renovations with Larry Baszynski and Scott Hodgden 53:36

2M ago53:36

53:36

Larry Baszynski and Scott Hodgden of Finance of America Commercial are seasoned lenders who have helped their investor clients build tremendous real estate portfolios and wealth. Larry and Scott discuss the products that their company offers including Fix and Flip loans, Construction Loans, and Long-Term loans for stabilized properties. They share …

1
Episode 297: How to Pay Less in Taxes Via Tangible Property Regulations with Brenten Blakeman 16:21

2M ago16:21

16:21

What are tangible property regulations and how can investors leverage this IRS code to pay less in taxes? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Brenten Blakeman, Tangible Property Tax Methods Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- P…

1
Episode 296: How to Crush RE Investments on Chicago’s South Side with Moses Hall 49:17

2M ago49:17

49:17

Moses Hall is a top producing commercial real estate broker and leads a brokerage that serves investors, landlords, and tenants. Moses discusses his start in real estate, taking the plunge to start his own business, and the challenges that came with that. He dives into his geographical areas of focus in Chicago and his investment strategy. Moses sh…

1
Homewrecker Ft. Jen Connor 56:34

2M ago56:34

56:34

Get ready for a rollercoaster ride of laughter and relatable woes as Jen Connor, actress, comedian, and lifelong tenant, spills the tea on her outrageous encounters with nightmare roommates and a landlord who's like a permanent resident of 'Neglectville'. 🏠☕ Tune in as we unpack the highs, lows, and downright absurdities of city living with someone…

1
Episode 295: The Ultimate HACK to Long-Term Wealth with Brian Tibbs 1:05:20

2M ago1:05:20

1:05:20

Brian Tibbs is an investor and best-selling author who teaches others how to thrive financially! Brian starts by sharing how he hit the ground running by house hacking multiple properties and scaling up to 10-units before the age of 30! He explains how he saved money for down payments and the setbacks he experienced during his early REI days. Brian…

1
Episode 294: Creating a Successful Operating Agreement with Chance Badertscher 11:48

2M ago11:48

11:48

What items need to be covered in a successful operating agreement? 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 Copyright of Straigh…

1
Episode 293: Help! Firefighters, City Inspectors, and Police Officers Are All at My Building With Anthony Rodriguez From Drexel Properties 53:47

3M ago53:47

53:47

Anthony Rodriguez is an experienced Chicago Property Manager who manages over 300 units for Drexel Properties! Anthony starts by discussing his previous experience in other industries and how those skills have translated into his real estate career. Then, Tom and Anthony retell the story of how their team managed a boiler explosion in a multifamily…

1
Don't Forget Your Keys! 44:16

3M ago44:16

44:16

Guest Patrick Shipp, of The Olive Well Real Estate Group, dives into the trials and tribulations of the crazy things that can happen when you’ve been in real estate for 11 years! Connect with Patrick: @ChiRealtorPat Subscribe: YouTube Submit your own Story: Anonymous Submission Form In this episode: 0:00 – Intro 1:56- Learn about our Guest, Patrick…

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Episode 292: Why Investors Need to Know a Good Public Adjuster with Dorian Bezanis 59:16

3M ago59:16

59:16

Chicago Native Dorian Bezanis is the president of ALPHA Adjusting and has nearly four decades of investing experience in Chicago’s Northside! Dorian jumps right in by discussing the investing portfolio he’s built in Edgewater and Rogers Park over the last 37 years. He explains the role of a public adjuster, the immense value they bring to investors…

1
Episode 291: What Every Investor Needs To Know About the Rehab Draw Process 22:15

3M ago22:15

22:15

How does the draw process work when taking on a construction loan? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman, Renovo Financial Link: Workman Lending Team - Renovo Financial - Real Estate Investment Loans ----------------- Production House: Flint Stone Media Copyr…

1
Episode 290: Want To Make It 20+ years in Chicago REI? Learn How With Neena Vlamis 50:53

3M ago50:53

50:53

Neena Vlamis is the President and Owner of A and N Mortgage. Born and raised in Chicago, she discusses building her mortgage company along with developing an impressive real estate investment portfolio in Chicago. Neena starts by explaining how she scaled her mortgage company, building a culture, and behind the scenes challenges. She provides insig…

1
This one's a Design Doozie 45:48

3M ago45:48

45:48

SUBMIT YOUR STORIES ANONYMOUSLY HERE! This Episode’s Design Doozies are brought to you by Melinda Cabanilla. Melinda is the principal designer and founder of Flat Pack Kitchen Design. She holds a masters in Interior Design from the Boston Architectural, college. Her studio is based out of Chicago Illinois and her work consists of new construction d…

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

3M 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

3M 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

4M 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
Terrence tries Empathy 44:43

4M ago44:43

44:43

Jamie and Terrence go down the rabbit hole telling their own crazy stories starting with a game of 2 truths and a lie. Have a wild, crazy, or interesting story of your own? SUBMIT YOUR ANONYMOUS STORIES HERE! Jamie's 2 truths and a lie: I've walked in on a live stream of the building's lobby in someone's unit. I've taken a potential client to their…

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

4M 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

4M ago14:36

14:36

By Mark Ainley and Tom Shallcross

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

4M 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
Change Your Locks and Your Toilet Seats 1:01:45

4M ago1:01:45

1:01:45

Hosts Jamie and Terrence interview Chicago and Western suburb expert agent Ayushi Kukreja. Jamie and Ayushi worked together for several years at Berkshire Hathaway before each going their own directions, Jamie to Compass and Ayushi to @properties. Ayushi’s 2 truths and a lie - She walked into the wrong unit and cleaned up a strangers house for an o…

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

4M 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

4M 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

5M 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
Plugged Pipes and Professional Tenants 1:15:45

5M ago1:15:45

1:15:45

Hosts Jamie and Terrence interview Melissa Tannehill, a fantastic real estate attorney who owns her own firm and represents clients in real estate transactions, business planning, and estate planning. Melissa shares some personal stories of ghosts in her own home and provides some insight on the ongoing tenant landlord feud. Melissa’s 2 truths and …

1
Cockroaches, Corpses, and Cuckoos 50:30

5M ago50:30

50:30

Hosts Jamie and Terrence interview guest Jackie Kelly, a Chicago and Charleston Realtor, resulting in some wild stories on this episode. Jackie recounts her experiences with snakes, eccentric sellers, and Chicago night life. Jackie's 2 truths and a lie: She has picked up clients in traffic before, she has fallen through a floor during a show, and s…

1
Bugs, Birds, and Big Chugs 41:31

5M ago41:31

41:31

Welcome to RealTea Chicago, the podcast where we share the most interesting stories we can find in Chicago Real Estate. In this episode we get to know our hosts, Jamie Book and Terrence Terrell, 2 real estate professionals, as they share some of their personal real estate stories. Find Jamie on Instagram - @justbookjamie Jamie's 2 truths and a lie …

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

5M 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

5M ago14:35

14:35

By Mark Ainley and Tom Shallcross

1
Welcome to RealTea Chicago 0:33

5M ago0:33

0:33

Welcome to the RealTea Chicago Podcast. We are two real estate professionals sharing the most interesting stories we can find in Chicago real estate. Jamie has lived in Chicago for over 7 years and has been a real estate agent, investor, rehabber, and airbnb host since 2018. Terrence is a Chicago native with 8 years of real estate investing and mor…

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

5M 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

5M 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

5M 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

5M 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…

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Straight Up Chicago Investor Podcasts

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