Straight Up Chicago Investor

Latest Episodes:

Episode 144: Straight Up Tues Tip 30 - Perry Farella Provides Numbers on a Recent Purchase and Rehab Projects He Financed May 31, 2022

Show notes

Perry Farella provides tangible numbers on a recent purchase and rehab project he financed.

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Perry Farella of Prime Lending

Link: ttps://perryfarella.com/blog/

Link: https://www.straightupchicagoinvestor.com/podcast/episode-67-chicagoland-rehab-financing-without-using-hard-money-or-203k-loans

-----------------

Production House: Flint Stone Media

Episode 143: Ins and Outs to Navigating Chicago Short-Term Rentals with Jessica Ryan May 26, 2022

Show notes

Have you also been considering short-term rentals to increase your NOI?! Jessica Ryan joins us to share valuable knowledge on considerations when planning your short-term rental!

Jessica starts off by explaining the main points of the Chicago Shared-Housing Ordinance and how to get a license for a short-term rental. She touches on notice requirements to other tenants, percentage of short-term rental rentals allowed within a building, and other limitations to consider when planning a short-term rental. Jessica closes by sharing some of the more interesting/goofy short-term rental stories that she has seen in her legal practice. Listen to this one closely so that you plan your short-term rental correctly and don't need Jessica to represent you in court!

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: Jessica Ryan from KSN Law

Link: Network Recommendation (Tim Jacobs)

Sponsors: Prime Lending and Appeal.tax

-----------------

Guest Questions

02:28 House Provider Tip: Look out for leaks when turning on your water spigots this spring!

04:20 Intro to our guest, Jessica Ryan!

05:20 How did short-term rentals start in Chicago?

07:59 What are some of the requirements of the short-term rental ordinance?

14:23 How do you start the process to obtain a short-term rental license?

15:58 Are there any legal notices required to other long-term tenants when adding a short-term rental to a building?

20:40 What are some of the main points that cause application denials?

24:25 How many short-term rental units are allowed in multi-family buildings?

28:13 What are the requirements for individual room rentals?

30:40 What rights does a long-term landlord have on a tenant running an authorized short-term rental in their unit?

33:13 Any funny/interesting short-term rental stories?

37:15 Does Jessica foresee modifications to the Ordinance in the near future?

Wrap Up Questions

40:20 What is Jessica's competitive advantage?

40:53 What is the one piece of advice for new investors looking to buy their first property in Chicago?

41:29 What do you do for fun?

42:31 Good book, podcast, or self development activity that you would recommend?

43:28 Local Network Recommendation?

44:17 How can the listeners learn more about you and provide value to you?

That's our show! Thanks for listening!

-----------------

Production House: Flint Stone Media

Episode 142: Generating Infinite ROI From Chicagoland Senior Living Investing with Brandon Schwab May 19, 2022

Show notes

Wondering how you can invest in a niche asset class to reduce your competition? Brandon Schwab talks about how he is revolutionizing the Chicagoland Senior Living space and making it a very profitable investment.

Brandon starts off by talking about his motivation to improve the Senior Living experience and the pitfalls he faced when starting out. He dives deep into the acquisition, rehab, and management of these Senior Living homes. He comments on the nuances of zoning, permitting, and appraisals on this asset class. on the volatility in the market and looks back on how the pandemic shaped what is happening today. Chris also gives an impactful outlook on Senior Housing as an investment including how the pandemic changed the industry and has uncovered the need for high quality Senior Housing providers!

If you enjoyed listening to today's episode, please leave us a 5 star review and share us with a friend!

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Brandon Schwab from Shepherd Premier Senior Living

Link: Book Recommendation

Link: Podcast Recommendation

Link: SUCI Merch Store

Sponsors: Prime Lending and Appeal.tax

-----------------

Guest Questions

03:30 House Provider Tip: Be aware of the Chicago Heat Ordinance that is still applicable even as the weather heats up!

04:50 Intro to our guest, Brandon Schwab!

06:50 What is a high-level overview of Brandon's Senior Living Homes business?

08:17 How did Brandon come up with his business idea?

12:49 What would be the first steps to start investing in Assisted Living Homes?

17:33 What are some of the pitfalls when getting started?

21:30 What do the rehabs of these Assisted Living homes consist of?

25:28 What does the on-going management look like?

27:57 How are these properties appraised?

33:12 What is Brandon's outlook on the Assisted Living Homes industry?

35:55 What are the Zoning and Permitting requirements for these types of properties?

37:19 Does the Village or Town that the property is in impact the requirements?

38:15 What are the financing/funding options for these properties?

Wrap Up Questions

40:57 How has Brandon overcome challenges in this niche space?

42:13 What is the one piece of advice for new investors looking to buy their first property in Chicago?

43:40 What do you do for fun?

44:18 Good book, podcast, or self-development activity that you would recommend?

45:59 Local Network Recommendation?

46:45 How can the listeners learn more about you and provide value to you?

That's our show! Thanks for listening!

-----------------

Production House: Flint Stone Media

Episode 141: Straight Up Tues Tip 29 - Noah Birk and Aaron Sklar Sit Down to Explain How Investors New To The Multifamily Space Can Catch A Broker's Eye May 17, 2022

Show notes

As an investor, how do I get the attention of the most successful brokers in the Chicagoland area?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Noah Birk & Aaron Sklar of Kiser Group

Link: Episode 23 of Straight Up Chicago Investor

-----------------

Production House: Flint Stone Media

Episode 140: Providing Necessary Education for Chicago Investors with CIC's Jessica Sivels May 12, 2022

Show notes

Interested in sharpening your education to propel your Chicago Real Estate Investments? Jessica Sivels explains the variety of resources that Community Investment Corporation (CIC) is providing.

Jessica provides a brief summary of CIC's extensive experience and explains how CIC can be a value add to investors given their knowledge of Chicago. She dives deep into CIC's vast educational resources and how landlords can benefit greatly by investing in their education. Fair housing, property management, mixed-use buildings, and lending are among the few topics discussed on this value-loaded episode!

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: Jessica Sivels, Community Investment Corporation (CIC)

Link: Jessica Sivels - Director of Education & Community Engagement - Community Investment Corporation | LinkedIn

Link: Jessica's Facebook

Link: The One Thing (Book Recommendation)

Sponsors: Kiser Group, and Appeal.tax

-----------------

Guest Questions

02:44 House Provider Tip: Be aware of power outages during this Spring season!

05:10 Intro to our guest, Jessica Sivels!

06:54 Who is CIC and how does Jessica fit into the corporation?

08:07 When did CIC start offering its educational resources?

10:09 Why did Jessica get involved with CIC?

12:57 What is the spectrum of CIC's educational resources and what are the topics with the most need for education?

18:33 What are the opportunities coming up in the mixed-use space?

21:55 Is CIC going to start in-person classes?

29:05 Are there new CIC education topics or tools on the horizon?

34:35 What are some lending advantages that CIC offers?

Wrap Up Questions

41:17 What is Jessica's competitive advantage?

41:52 One piece of advice for new investors.

42:50 What do you do for fun?

43:12 Good book, podcast, or self development activity that you would recommend?

43:35 Local Network Recommendation?

44:28 How can the listeners learn more about you and provide value to you?

That's our show! Thanks for listening!

-----------------

Production House: Flint Stone Media

Episode 139: Leveraging Technology to Efficiently Manage your Chicago Property Portfolio with Kerri Davis May 05, 2022

Show notes

Looking for a user-friendly, innovative property management software? Today's guest Kerri Davis dives deep into how her software Fortress can help you take your investment management to the next level.

Kerri jumps right in by explaining the shortcomings of other management softwares and how Fortress addresses those concerns. She talks about when it makes sense for an investor to transition to management software and describes the typical workflow within the Fortress interface. Kerri proudly elaborates on the innovative features of her platform, its user-friendliness, and transparency to help you accurately gauge the performance of your properties!

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: Kerri Davis, Fortress Technology Solutions

Link: Kerri Davis' LinkedIn

Link: Start With Why (Book Recommendation)

Link: Sabrina Wottreng (Network Recommendation)

Sponsors: Kiser Group, and ClickInvest

-----------------

Guest Questions

03:57 House Provider Tip: Consider artificial grass, mulch, or rocks instead of natural grass to reduce maintenance on your properties!

06:29 Intro to our guest, Kerri Davis!

07:45 How did Kerri get into real estate?

08:45 What did Kerri's first property management role involve?

10:06 What were the pitfalls of older property management softwares and how are new softwares addressing those concerns?

13:42 What were some of the main pain points that led Kerri to develop her software, Fortress PropTech?

16:40 At what point or unit count does it make sense for a landlord to switch over to a property management software?

21:57 Kerri describes the typical workflow when using her software.

25:50 How does a platform like Fortress help build and strengthen the relationship between landlords and tenants?

28:09 What does the future development of Fortress look like?

32:17 Can a CRM be integrated into Fortress?

34:08 What pricing can users expect for the software and what factors impact pricing?

Wrap Up Questions

36:17 What is Kerri's and Fortress' competitive advantage?

37:35 One piece of advice for new investors.

38:39 What do you do for fun?

39:18 Good book, podcast, or self development activity that you would recommend?

40:13 Local Network Recommendation?

40:55 How can the listeners learn more about you and provide value to you?

That's our show! Thanks for listening!

-----------------

Production House: Flint Stone Media

Episode 138: Straight Up Tues Tip 28 - Mike Scanlon Talks Through How He Sourced An Off Market Househack Deal May 03, 2022

Show notes

Mike Scanlon walks us through the numbers, rationale, and challenges of a recent househack in Elgin.

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Mike Scanlon from The Axon Group (EXP Realty)

-----------------

Production House: Flint Stone Media

Episode 137: Revitalizing Chicago's Bronzeville Neighborhood via a $4 Billion Dollar Development with Morgan Malone Apr 28, 2022

Show notes

Ever wonder what goes into planning a multi-billion dollar equitable development and how those principles can be applied to your investing? Morgan Malone joins us to break down how this can be accomplished while maintaining the character of a neighborhood.

Morgan provides a history of the Bronzeville Lakefront Planned Development and a behind-the-scenes look into overcoming challenges associated with planning such a large-scale development. Morgan explains the multiple parties involved in such a large development and how she successfully works across multiple stakeholders, and ensures the community needs are being met. Morgan provides a strong, fact-based stance on the quality of the Bronzeville neighborhood and speaks to the challenge of planning equitable development while preserving the community's character and history. She closes with jewels of wisdom on building relationships within your community rather than solely focusing on the transactional elements of investing!

If you enjoyed listening to today's episode, please leave us a 5-star review and share us with a friend!

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Morgan Malone of Farpoint Development

Link: Farpoint Team

Link: Morgan's LinkedIn

Link: Bronzeville Lakefront Project (City Page)

Link: Disco Demolition Night (Podcast Recommendation)

Sponsors: Kiser Group, and Appeal.tax

-----------------

Guest Questions

05:06 House Provider Tip: Optimize floor plans when possible particularly if gut-rehabbing units!

07:10 Intro to our guest, Morgan Malone!

08:30 What is Morgan's background?

09:42 What is the background on the Bronzeville Lakefront Development project (former site of Michael Reese Hospital and Medical Center)?

13:43 What are the challenges of formulating and working with a team on large development projects?

16:13 How much direction did the City provide during the RFP process for the Bronzeville Lakefront project?

18:52 Was there any push back from the community on this planned development?

29:00 How did Morgan's team market such a large scale project to the community?

38:42 How would Morgan respond to someone questioning the quality of the Bronzeville neighborhood?

41:10 What have been the biggest unforeseen obstacles on this Bronzeville Lakefront project?

Wrap Up Questions

54:55 What is Morgan's competitive advantage?

55:34 What is the one piece of advice for new investors looking to buy their first property in Chicago?

56:29 What do you do for fun?

57:00 Good book, podcast, or self development activity that you would recommend?

57:46 Local Network Recommendation?

58:25 How can the listeners learn more about you and provide value to you?

That's our show! Thanks for listening!

-----------------

Production House: Flint Stone Media

Episode 136: From Failed Chicago Flip to a $90M in Multifamily Portfolio with John Casmon Apr 21, 2022

Show notes

Return guest (Episode 15) John Casmon drops in to share golden nuggets on how he separates himself from the competition in this tight market!

John starts off by reminding us of his humble real estate beginnings which came via a house hack in the North Center neighborhood of Chicago. He explains how his flipping experience helped propel his growth despite facing adversity. John provides tips on how investors can create opportunities and separate themselves from their competition in this highly competitive environment. Mr. Casmon shares practical advice on deal screening, approaching investors for syndication deals, and finding a mentor/coach!

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: John Casmon, Casmon Capital

Link: Capital Impact Club (Coaching)

Link: Multifamily Insights Podcast

Sponsors: Kiser Group, and Appeal.tax

-----------------

Guest Questions

03:09 House Provider Tip: Watch out for fraudulent rental applications!

05:44 Intro to our guest, John Casmon!

07:14 How does a newer investor get involved in multi-family real estate?

11:22 Why did John decide to get into flipping properties?

17:41 What experience did John gain flipping properties?

23:33 What motivated John to keep going after his struggles with flipping?

30:14 How can investors create deal opportunities in this limited supply market?

34:22 How can investors balance valuing properties based on current value compared to future value?

37:33 How do John and his team screen deals?

39:18 What is the difference between syndicating and joint-venturing a real estate deal?

42:31 What is it like to approach investors with a deal?

47:15 What's the best way to get connected with a mentor/coach?

49:39 What made John start his podcast and how has it helped his growth?

Wrap Up Questions

52:40 What is John's competitive advantage?

52:57 What is the one piece of advice for new investors looking to buy their first property in Chicago?

53:49 What do you do for fun?

54:02 Good book, podcast, or self development activity that you would recommend?

55:12 Local Network Recommendation?

55:50 How can the listeners learn more about you and provide value to you?

That's our show! Thanks for listening!

-----------------

Production House: Flint Stone Media

Episode 135: Straight Up Tuesday Tip 27 - Jake Parker and Andy Friedman Answer "What is a Condo Deconversion and How Can Investors Benefit From Purchasing a Deconversion Opportunity?" Apr 19, 2022

Show notes

What is a condo deconversion and how can investors benefit from purchasing a deconversion opportunity?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Jake Parker & Andy Friedman from Kiser Group

-----------------

Production House: Flint Stone Media