Dan Nelson is a real estate agent and investor with over 2 decades of experience flipping properties and buying rentals!

Dan jumps right in by explaining his start in real estate and how success in poker helped fund his real estate business! He breaks down his first few flip projects including lessons learned and great tips on vetting contractors. Dan talks through the challenges of getting off the ground as a new real estate agent and provides advice for rookie agents. He gets granular on investment performance expectations across various Chicago neighborhoods including areas he is extra bullish on. Throughout the episode, Dan hammers home the importance of taking a 10,000-foot view letting time be your biggest asset when it comes to succeeding in real estate investing!

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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Guest: Dan Nelson, Dan Loves Houses

Link: Dan's Instagram

Link: Dan's Compass Page

Link: The War of Art (Book Recommendation)

Guest Questions:

02:03 Housing Provider Tip - Protect yourself against rental listing scams.

04:20 Intro to our guest, Dan Nelson!

13:02 How to find and vet contractors.

14:24 Dan's geographic area of focus!

18:01 Getting off the ground as a new real estate agent.

20:23 Chicago neighborhood expectations for investors!

30:25 Providing value as a real estate agent.

34:25 Common mistakes investors make when analyzing buildings.

41:33 Dan's outlook on Chicago!

44:23 What is your competitive advantage?

45:33 One piece of advice for new investors.

46:14 What do you do for fun?

46:25 Good book, podcast, or self development activity that you would recommend?

46:50 Local Network Recommendation?

47:14 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.

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!

=============

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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Guest: 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.