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Tom Raleigh, Founding Attorney of Halsted Law Group, returns after being on Episode 40 to talk evictions!
Tom jumps right in by breaking down the eviction process and the timelines in 2025. He gives great tips on getting ahead of the process and emphasizes the importance of staying on top of tenants and not waiting too long to file the eviction case. Tom hits us with rapid fire eviction stats including neighborhoods and even streets where his office has had the most eviction filings. He closes with top insights on complying with Fair Housing and tenant screening to avoid eviction court altogether!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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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: [email protected]
Guest: Tom Raleigh, Halsted Law Group
Link: Tom Raleigh's LinkedIn
Link: Meditations (Book Recommendation)
Link: Shawn Ryan Show (Podcast Recommendation)
Guest Questions02:27 Housing Provider Tip - Dial in your tenant screening process to prevent issues!
04:17 Intro to our guest, Tom Raleigh!
5:01 The Eviction Process in 2025.
12:48 How can landlords get ahead in the eviction process?
21:56 Rapid fire stats on Tom’s eviction filings!
30:40 Housing Section of the CARES Act.
39.28 10 Day Notice for Cause.
47:36 Tips for Landlords to avoid Fair Housing violations.
55:41 What is your competitive advantage?
56:15 One piece of advice for new investors.
56:32 What do you do for fun?
56:58 Good book, podcast, or self development activity that you would recommend?
57:38 Local Network Recommendation?
58:38 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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What can I do to maximize my tax returns?
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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: [email protected]
Guest: Michael Procaccio, Pro Financial Services Group Inc.
Link: Build Your Team | Straight Up Chicago Investor Podcast
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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Saknas det avsnitt?
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Tom and Mark interview some of Chicago’s Real Estate Heavy Hitters during Kiser Group’s 20 Year Anniversary Celebration! Conversations range from condo deconversions, the attorney review side of a commercial deal, and the origins and evolution of Kiser Group. This show is full of wisdom from Kiser Group’s top brokers and business partners so prepare to learn from some of the best folks in the industry!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Lee Kiser and Guests, Kiser Group
Link: SUCI Ep 239 - Reducing Assessed Value with Fritz Kaegi and Stacie Young
Guest Questions
02:57 Housing Provider Tip - People like doing business with people that they like so treat people well!
04:48 Jake Parker’s insights on condo deconversions and more!
10:09 Andy Friedman reflecting on 7 years at Kiser Group!
19:15 Scott Weinstein: Advice from a Commercial Real Estate Attorney.
26:04 Corey Oliver on acquiring and stabilizing multifamily buildings.
37:03 Top tier commercial lending tips with Matt Bower!
44:48 Dominating in Chicago’s Southside with Aaron Sklar!
57:02 CIC’s latest loan options with Stacie Young!
62:20 Kiser Group’s Origins with Estella and Lee Kiser!
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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Frank Montro, the King of Chicagoland, returns to share how he and his real estate team have remained top producers during recent years of high interest rates and prices.
Frank explains how he coaches buyers to understand monthly payments as opposed to being scared off by rates and pricing. He discusses the keys to getting off the ground as a new broker and/or investor including tips on networking and cold calling. Frank gives brutally honest advice on the work ethic required to succeed and warns “order-taking” agents of the challenges they will face in this market. In this show, Frank empowers you to “put your nose to the grindstone” to stay ahead of your competition!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Frank Montro, Frank Montro Homes
Link: SUCI Ep 64 - Frank Montro
Link: Exactly What To Say (Book Recommendation)
Link: Martin Lorenzen (Lender Referral)
Guest Questions
02:45 Housing Provider Tip - Notify your insurance broker of slip and fall incidents to ensure you’re covered!
04:49 Intro to our guest, Frank Montro!
17:24 Surviving as a new broker in today’s market.
23:54 Keys to lead generation and deal flow!
40:16 Committing to real estate while having work-life balance.
64:36 What is your competitive advantage?
64:55 One piece of advice for new investors.
65:24 What do you do for fun?
66:08 Good book, podcast, or self development activity that you would recommend?
66:42 Local Network Recommendation?
67:20 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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What Can I Write Off as a Chicago Househacker?
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Michael Procaccio, Pro Financial Services Group Inc.
Link: Build Your Team | Straight Up Chicago Investor Podcast
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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Jake Fugman and Mike Scanlon of The Axon Group return to discuss Chicago’s REI market performance, predictions, and exciting developments!
Jake and Mike kick things off by assessing their 2024 predictions regarding mortgage rates, appreciation, and cap rates! They then break down the impacts of the Northwest Side Housing Preservation on landlords in the area and provide noteworthy predictions for 2025. These predictions include what the new presidential administration will mean for the downtown market, househacker purchasing power with 5% down, the 1901 project, the path of progress, and much more!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Jake Fugman & Mike Scanlon, The Axon Group
Link: The Axon Group Instagram
Link: SUCI Ep 268 - 2024 Predictions with Jake and Mike
Link: SUCI Ep 327 - Luke Blahnik on NW Preservation Ordinance
Link: REI Diamonds Podcast
Link: ADPI Podcast
Link: Kevin Kaspers (Lender Referral)
Link: Cost Seg Kev
Guest Questions
02:25 Housing Provider Tip - Consult with your attorney and insurance agent on handling slip and fall incidents.
03:17 Intro to our guests, Jake Fugman and Mike Scanlon!
7:59 House Hackers unlocking huge leveraged returns with 5% down!
16:13 What did cap rates do in 2024?
20:22 Prediction 1: The return of 100% bonus depreciation.
24:37 Impacts of the Northwest Side Housing Preservation Ordinance.
38:00 Will downtown Chicago make a comeback?
49:24 Investing in 2-4 unit new construction buildings.
54:37 The 1901 Project!
63:04 What is your competitive advantage?
65:33 One piece of advice for new investors.
67:28 What do you do for fun?
68:25 Good book, podcast, or self development activity that you would recommend?
70:26 Local Network Recommendation?
71:17 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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Mike Bednarz, an accomplished real estate investor and HVAC business owner, joins us to share his inspiring trajectory of growing a real estate portfolio and overcoming a scary accident!
Mike explains how he lived frugally to save a down payment and buy his first multifamily investment property in Edison Park. He discusses the discipline he used to acquire his second property and how he found a niche in mixed-use properties with leasing up local retail spaces. Mike shares a life changing incident where he fell off a ladder while working for his HVAC company that resulted in life threatening injuries. He breaks down his recovery despite doctors doubting that it was possible and bouncing back stronger than ever. This is the definition of an inspirational conversation around discipline and grit that you will not want to miss!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Mike Bednarz, Housing Opportunity Development Corporation (HODC)
Link: Eat That Frog (Book Recommendation)
Link: How Not To Die
Guest Questions
05:09 Housing Provider Tip - Understand the Illinois Landlord Retaliation Act!
06:51 Intro to our guest, Mike Bednarz!
15:40 Jumping into a 6-unit after a house hack!
21:32 Finding a niche in mixed-use buildings.
23:36 Mike’s scary accident.
31:58 Mike’s history of discipline.
35:47 What’s next for Mike and the meaning of purpose!
43:35 What is your competitive advantage?
44:57 One piece of advice for new investors.
45:37 What do you do for fun?
46:20 Good book, podcast, or self development activity that you would recommend?
47:42 Local Network Recommendation?
48:46 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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What are the current political issues Chicago investors need to be aware of and how can the NBOA help?
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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: [email protected]
Guest: Mike Glasser, NBOA
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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Richard Koenig is HODC’s Executive Director and has led the development of over 600 units of affordable housing!
Richard starts with how he found his “Why” and discovering that he wanted to dedicate his career to helping solve the lack of affordable housing. He gets granular on the financing and approval process on these types of developments. Richard compares market rate housing to affordable housing including cost to build and tenant screening. He shares advice on how smaller investors can help contribute to the affordable housing issue and make a positive impact in their community!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Richard Koenig, Housing Opportunity Development Corporation (HODC)
Link: SUCI Ep 283 - S.I. Container Builds
Link: Homelessness is a Housing Problem (Book Recommendation)
Guest Questions
01:48 Housing Provider Tip - The legal way around HOA rules about lease terms!
03:47 Intro to our guest, Richard Koenig!
08:15 Financing and tax credits for affordable housing development.
14:32 Guidelines for affordable housing designation.
19:08 Dealing with affordable housing critics.
25:31 The economics of building affordable housing.
31:05 Tenant screening process!
38:53 Contributing to affordable housing as a smaller investor.
44:58 Top challenges for developers.
48:27 Opportunities for improvements to bring more development.
51:39 What is your competitive advantage?
51:55 One piece of advice for new investors.
52:18 What do you do for fun?
52:40 Good book, podcast, or self development activity that you would recommend?
53:09 Local Network Recommendation?
54:07 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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Mike Tenerelli not only has a background in Reality TV, but also in construction, management, and sales which have propelled his explosive growth in real estate!
Mike discusses his journey from flipping homes to helping others find the right property. He breaks down analyzing remote markets to find lucrative deals, growing a brokerage business, and adapting to the new NAR rules around buyer’s broker compensation. Mike shares tremendous insights on investment opportunities in prime western burbs and lessons learned from flipping gone wrong!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Mike Tenerelli, Exit Real Estate Partners
Link: Mike's Instagram
Link: One Rental at a Time (YouTube Channel)
Link: Lending One (Lender Referral)
Guest Questions
02:27 Housing Provider Tip - Plan accordingly when giving Section 8 tenants notice to vacate!
04:24 Intro to our guest, Mike Tenerelli!
09:18 Becoming a full time investor after 2 flips!
11:42 Learning the Milwaukee market.
20:54 Growing a brokerage business.
24:38 Dealing with new NAR compensation rules.
33:10 The 101 on the Western Burbs!
38:01 Consequences of Flipping Gone Wrong!
42:02 What is your competitive advantage?
42:40 One piece of advice for new investors.
43:28 What do you do for fun?
43:46 Good book, podcast, or self development activity that you would recommend?
44:07 Local Network Recommendation?
44:46 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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When Does a 5 Day Notice Become a 30 Day Notice?
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Mark Ainley, Straight Up Chicago Investor Podcast
Link: Enforcing the CARES Act 30-Day Eviction Notice Requirement
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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Sam Patterson is a successful Commercial Real Estate Broker, Investor, and Restaurant Owner with vast experience in renovation and property management!
Sam opens with his experience in commercial real estate receiverships and his start in investing! He touches on structuring and leveraging partnerships to scale a real estate portfolio. Sam discusses ins and outs of DeKalb including the housing stock and the investment opportunities. In sharing his project experiences, Sam speaks to seller financing, TIF funds, and various other concepts to add to your real estate toolbox!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Sam Patterson, RVG Commercial Real Estate Services | Email Sam ([email protected])
Link: Sheela Prahlad (Lender Referral)
Link: Rob Zahm (Roofer Referral)
Guest Questions
03:39 Housing Provider Tip - Take precautionary measures to deal with Chicago’s frigid temperatures!
05:40 Intro to our guest, Sam Patterson!
08:41 Crazy receivership stories and becoming an investor!
19:48 Why invest in West Chicago?
23:01 Structuring a partnership.
29:57 DeKalb’s housing stock and investment expectations.
38:38 How TIF funds work!
41:13 Surprises on a large commercial property renovation!
44:16 An overview of Sycamore.
50:24 Refinance terms on a commercial loan.
53:17 What’s next in Sam’s investment journey?
58:24 What is your competitive advantage?
59:19 One piece of advice for new investors.
60:11 What do you do for fun?
60:49 Good book, podcast, or self development activity that you would recommend?
61:32 Local Network Recommendation?
62:11 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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Josh Bandoch is the Head of Policy at the Illinois Policy Institute where he works to spread awareness on improving housing policies to promote affordability and social mobility.
Josh starts by describing how he got into housing policy and the mission of the Illinois Policy Institute. He explains some of the prohibitive policies in Illinois that restrict development and the increase of housing supply. Josh discusses the power of ADUs to bring affordable housing supply and how other cities with less restrictions have successfully developed ADUs. He closes by explaining how Illinois can and should look at the policies in other states that have helped solve affordable housing and state debt issues. This is a great show to understand macro-level issues we deal with here in Illinois and how we can make our voice heard to help reach solutions!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Josh Bandoch, Illinois Policy Institute
Link: Josh's LinkedIn
Link: Thinking Fast and Slow (Book Recommendation)
Guest Questions
01:35 Housing Provider Tip - Keep heat on in vacant units to prevent pipe bursts and other issues during winter!
03:36 Intro to our guest, Josh Bandoch!
06:42 The Illinois Policy Institute and its mission!
13:21 Policies negatively impacting housing affordability.
24:23 Benefits of ADUs and restrictions in Illinois.
34:14 Places with the least amount of housing regulation.
38:05 Dissecting Illinois Property Taxes!
44:54 Looking outside of Chicago to solve Chicago’s problems!
47:47 What is your competitive advantage?
48:46 One piece of advice for new investors.
49:12 What do you do for fun?
49:47 Good book, podcast, or self development activity that you would recommend?
50:34 Local Network Recommendation?
51:00 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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What IL rules changes do investors need to be aware of in 2025?
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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: [email protected]
Guest: Mark Ainley, Straight Up Chicago Investor Podcast
Link: Cook County Landlords Won’t Need Sheriff to Serve 2025 Notices
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.
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Joey Turano is real estate broker and investor who has leveraged partnerships and low down payment loans to quickly build his multifamily buildings portfolio!
Joey starts by describing his “soul searching” journey in Europe and realizing that real estate would be his career path in life! He explains how he got scrapy to bring value to a Top Producing Real Estate agent and eventually joined the team to learn the ropes of real estate brokerage. Joey describes how he quickly purchased two househacks by leveraging low down payment loans and partnerships. He drops some hilarious horror stories on tenants and DIY projects and also reflects on his investment strategy and how it will be refined moving forward! This is another great show that demonstrates how taking action sooner than later is a key to success.
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Joey Turano, The Ben Lalez Team - Compass
Link: Joey's Instagram
Link: SUCI Ep 203 - Catalin Maticiuc
Link: Scott Schneiderman (Lender Referral)
Link: Extreme Ownership (Book Referral)
Guest Questions
03:31 Housing Provider Tip - Keep space heaters handy to be prepared for No Heat situations in winter!
06:16 Intro to our guest, Joey Turano!
10:33 Getting into real estate and choosing a team.
15:52 Working Zillow leads and getting into investing.
18:26 Strategies to get into REI!
21:36 Joey’s first deal.
26:51 Quickly buying deal #2.
30:20 Lessons from DIY projects and partnering with family.
35:09 Funny, horror stories!
38:20 Refining an investment strategy.
47:04 What is your competitive advantage?
47:45 One piece of advice for new investors.
48:32 What do you do for fun?
49:00 Good book, podcast, or self development activity that you would recommend?
49:32 Local Network Recommendation?
50:21 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2024.
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Boyan Salha is a seasoned General Contractor and the leader of his company Best Fit Homes. He joins us to share how he learned to source and renovate deals from working with a large investment group.
Boyan starts by explaining the investing lessons learned by working with a large investment group alongside previous guest Kirby Atwell! He breaks down how he sources and finances distressed properties. He discusses his flipping experiences and how margins have changed over the years. Boyan talks about building relationships with subcontractors and the value that a quality General Contractor brings to their client. This show is full of golden nuggets from the perspective of an investor GC!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Boyan Salha, Best Fit Homes
Link: SUCI Ep 321 - Kirby Atwell
Link: George Wyatt (Home Inspector Referral)
Link: Patrick Bet David (YouTube Channel)
Link: Atomic Habits (Book Recommendation)
Guest Questions
02:44 Housing Provider Tip - Adjust terms so rentals being marketed in the winter end during the spring/summer rental season.
05:17 Intro to our guest, Boyan Salha.
12:21 Connecting with Kirby Atwell and getting into real estate.
23:51 Starting a General Contracting business!
28:18 Financing distressed properties.
30:42 Transitioning from flips to owning rentals.
39:43 Working as a General Contractor for third parties.
42:31 Growing a team of sub-contractors and the value of a good GC!
48:58 Boyan’s investing strategy in 2024 and outlook on Chicago.
52:58 What is your competitive advantage?
53:30 One piece of advice for new investors.
54:35 What do you do for fun?
55:30 Good book, podcast, or self development activity that you would recommend?
57:08 Local Network Recommendation?
58:36 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2024.
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What do investors need to know about the new tenant credit report law?
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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: [email protected]
Guest: Mark Ainley, Straight Up Chicago Investor Podcast
Link: How 2025 Illinois Tenant Credit Report Law Impacts Landlords
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2024.
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Pete Neubig joins us to discuss how he built and sold a 7-figure property management company and started VPM Solutions; a platform designed to help property management and real estate professionals with staffing to improve efficiencies and profits!
Pete starts by explaining how he went from IT to building and selling a 7-figure property management company! He shares a brief horror story about getting sued for $1.5 million! He discusses how he started VPN Solutions on the “Who Not How” concept; Pete is leveraging remote staff to offload work to focus on higher-dollar activities. This show is packed with fantastic tips to help improve your business and grow your bottom line!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Pete Neubig, VPM Solutions
Link: NARPM Website
Link: Pete's LinkedIn
Link: Traction (Book Recommendation)
Guest Questions
03:08 Housing Provider Tip - Consider outsourcing all or select aspects of property management!
05:10 Intro to our guest, Pete Neubig!
9:27 Getting sued for $1.5 million!
11:21 Making the jump to start a business.
17:40 Finding a mentor / coach and growing a business!
27:58 Outsourcing property management!
39:04 Processes for hiring management personnel.
48:33 What is your competitive advantage?
49:05 One piece of advice for new investors.
49:15 What do you do for fun?
50:00 Good book, podcast, or self development activity that you would recommend?
50:25 Local Network Recommendation?
50:42 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2024.
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Susan Tjarksen is the Managing Director at Cushman & Wakefield and has led the development of residential and commercial across the country!
Susan discusses her time in hotel management and shares some funny/horror stories! She explains how receiverships work and how investors can capitalize on this opportunity. She breaks down the nuances of large scale developments including insane time frames on projects of this magnitude. Susan fires us up with an epic rant on why Chicago is the place to be and is set up to continue growing and thriving!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Susan Tjarksen, Cushman & Wakefield
Link: SUCI Ep 29 - Ciere Boatright
Link: SUCI Ep 68 - Lee Kiser
Link: SUCI Ep 274 - Marc Rutzen
Link: The Overstory (Book Recommendation)
Guest Questions
04:02 Housing Provider Tip - Negotiate spring season exterior projects now to get the best pricing!
05:48 Intro to our guest, Susan Tjarksen!
8:57 Horror stories from Susan’s hotel management days!
12:25 Permitting/Zoning insights for large scale developments.
15:08 The Ins and Outs of Receivership.
19:29 Establishing a real estate brokerage.
24:50 Transitioning to Cushman & Wakefield.
29:55 Considerations on large scale developments.
44:23 Reasons to be bullish on Chicago!
48:25 What is your competitive advantage?
48:53 One piece of advice for new investors.
49:20 What do you do for fun?
49:40 Good book, podcast, or self development activity that you would recommend?
50:28 Local Network Recommendation?
51:00 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2024.
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What is an enterprise zone and how can investors benefit from these areas?
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guest: Tom Shallcross, Straight Up Chicago Investor Podcast
Link: Chicago Enterprise Zone Application
Link: Chicago Enterprise Zone Program
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2024.
- Visa fler