Brendan McElhaney, founder of Cash for Chicago Houses, is a real estate wholesaler and investor who specializes in sourcing off-market deals through direct-to-seller marketing!

Brendan explains how he started in real estate with a house hack and how that helped him leave his corporate job to pursue real estate full time! He talks about renovation mistakes and leasing insights that he learned on his first few deals. Brendan dives deep on getting a wholesaling business off the ground, establishing a team, and lessons learned from wholesales gone wrong. He shares how he is leveraging social media to provide value to others and grow his business and also provides an outlook on Chicago. Throughout the show, Brendan demonstrates that hard work and grit have been the keys to his 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: StraightUpChicagoInvestor@gmail.com

Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com

Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement

Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com

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Guests: Brendan McElhaney, Cash for Chicago Houses

Link: Brendan's Instagram

Link: Nick Jakubco (Attorney Referral)

Link: SUCI Build Your Team

Guest Questions:

03:19 Housing Provider Tip - Understand the limits on collectible security deposits.

05:09 Intro to our guest, Brendan McElhaney!

10:37 Leasing mistakes and lessons learned.

16:58 Getting a wholesaling business off the ground!

25:11 Wholesale deals gone wrong.

32:14 Building a reputation as a new wholesaler!

40:59 Establishing a wholesaling team and process.

43:34 Leveraging social media.

48:00 Brendan's outlook on his business and Chicago!

51:05 What is your competitive advantage?

52:24 One piece of advice for new investors.

53:08 What do you do for fun?

54:08 Good book, podcast, or self development activity that you would recommend?

54:42 Local Network Recommendation?

54:56 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 2026.

How do I best prepare for an upcoming appraisal?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Tom & Mark, Straight Up Chicago Investor

Email the Show: StraightUpChicagoInvestor@gmail.com

Link: Build Your Team | Straight Up Chicago Investor Podcast

Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com

Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement

Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

Ryan Bakke turns to discuss the power of smart business acquisitions and tax strategy to skyrocket returns and keep more money in your pocket!

Ryan starts by reminding us the tax benefits of short-term rentals and real estate professional status. He explains the process of buying businesses including defining a buy box, identifying opportunities, and improving operations upon acquisition. He dives deep on lessons learned from operating businesses and tips on how to improve efficiencies through off-shore staffing. The show closes with great insights on assessing return on equity and investment to ensure your capital is working as hard as possible.

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

Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com

Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement

Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com

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Guests: Ryan Bakke, Tax Strategy 365

Link: SUCI Ep 244 - Ryan Bakke

Link: Ryan's Instagram

Link: Influence (Book Recommendation)

Link: SUCI Investor Meetups Page

Guest Questions:

01:24 Housing Provider Tip - Understand the maintenance and life span of hot water heaters.

03:34 Intro to our guest, Ryan Bakke!

06:42 Leveraging short-term rentals for tax benefits.

11:26 Efficiently delegating to grow your business.

22:37 How to hire off-shore employees.

28:32 The process of buying a business.

32:03 Defining a "buy box" for a business.

39:07 Lessons learned from buying businesses.

46:08 Ryan's take on ROI and Chicago's future!

53:28 What is your competitive advantage?

53:37 One piece of advice for new investors.

53:46 What do you do for fun?

53:59 Good book, podcast, or self development activity that you would recommend?

54:17 Local Network Recommendation?

54:35 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 2026.