Straight Up Chicago Investor

Latest Episodes:

Episode 254: Becoming a Straight Up Chicago Investor With Life Lessons From the Military with Edgar Barbosa Nov 02, 2023

Show notes

Edgar Barbosa is an investor and realtor with a focus on helping clients get into REI to start their wealth building journey!

It's clear the Military is not for the weak, and Edgar speaks to the lessons learned during his time served along with how he applies those teachings to his current lifestyle and investments. He dives into his first househack in Cicero including how he decided on the investment type, price point, and location. The power of the VA loan is brought up and Edgar discusses his plan to strategically continue leveraging that benefit. Edgar discusses his second investment which was a condo in Fulton Market and gives his perspective on investing in an A+ location. A repeated theme of this episode is the importance of building good habits, being disciplined, and doing right by others to obtain success in real estate and life as a whole!

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: Edgar Barbosa, RE Investors Brokerage

Link: SUCI Ep 245 - JD Modrak

Link: Discipline is Destiny (Book Recommendation)

Link: Edgar's Instagram

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Guest Questions

02:50 Housing Provider Tip: Check appliances for roaches and other pests!

04:15 Intro to our guest, Edgar Barbosa!

07:43 Joining the military and lessons learned!

15:13 Life after the military and starting in real estate.

18:26 Edgar's first househack!

21:02 The Power of the VA Loan.

25:14 Edgar's second deal.

29:59 Renting to family and friends.

31:29 Fulton Market condo as an investment.

35:57 Edgar's search for a SFH rehab project.

38:52 Getting a Real Estate license.

42:16 What is Edgar's competitive advantage?

42:47 One piece of advice for new investors.

43:09 What do you do for fun?

43:18 Good book, podcast, or self development activity that you would recommend?

43:57 Local Network Recommendation?

44:25 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 253: Purchasing 1,000 Chicagoland Properties Through Extensive Marketing with Jeff Nydegger Oct 26, 2023

Show notes

Jeff Nydegger has over 17 years of real estate experience including over 1,000 homes bought and repositioned in Chicagoland!

Jeff jumps right in by sharing how skill sets built in the Military have served him in his REI ventures. He dives deep into his rough start in real estate including the mental resilience and grit it took to overcome the adversity! Jeff breaks down how Short Sales became a big part of his business during the last RE crash and shares some crazy short sale stories. To conclude our show, Jeff gets granular on the marketing efforts of a professional real estate investor to find deal flow in a low inventory market.

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: Jeff Nydegger, Kendall Partners and JeffBuysYourHouse.com (a division of Kendall Partners)

Link: The 7 Habits of Highly Effective People (Book Recommendation)

Link: Mastering the Rockefeller Habits (Book Recommendation)

Link: Eric Workman (Network Referral)

Link: SUCI Ep 79 - Gary Davidson (Network Referral)

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Guest Questions

01:44 Housing Provider Tip: Network with wholesalers to maximize opportunities for deals!

02:54 Intro to our guest, Jeff Nydegger!

06:20 Skills from the Military translating to Real Estate!

08:18 Getting Jeff's real estate business off the ground.

17:46 Continuing the grind after a rough start.

27:38 Crazy Short Sale stories!

31:08 Pivoting to continue business growth.

41:24 Marketing and creating deal flow!

59:20 Jeff's outlook on his business and on the Chicago market!

60:27 What is Jeff's competitive advantage?

60:51 One piece of advice for new investors.

61:54 What do you do for fun?

62:18 Good book, podcast, or self development activity that you would recommend?

62:54 Local Network Recommendation?

64:24 How can the listeners learn more about you and provide value to you

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Production House: Flint Stone Media

Episode 252: Conventional Financing vs DSCR Loans Oct 24, 2023

Show notes

What are the pros/cons between conventional financing and DSCR loans?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Eric Workman, Renovo Financial

Link: Episode 19: Top 10 Mistakes We See From Chicago Investors - with Eric Workman of Renovo Financial (Part 2)

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Production House: Flint Stone Media

Episode 251: Powerful Networking and Property Management Insights with Bob Hansen Oct 19, 2023

Show notes

Bob is a successful realtor and investor with a focus on House Hacking to help her clients build investment portfolios!

Bob kicks things off by talking about the power of networking and gives tips on developing networking skills. He discusses his vast experience working with property managers and housing providers along with insights on improving management efficiencies. Bob shares how his company Second Nature is helping property owners reduce their HVAC maintenance and expenses by facilitating air filter replacements! Throughout the show, Bob emphasizes the importance of networking and treating others right as keys to success in real estate and life!

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: Bob Hansen, Second Nature

Link: Leadership Strategy and Tactics: Field Manual: Willink, Jocko

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Guest Questions

03:02 Housing Provider Tip: Write Leases to place responsibility of Furnace Filter Replacement on your Tenants!

04:30 Intro to our guest, Bob Hansen!

10:59 Cultivating ability to network and its importance!

13:41 Networking tips for newbies and introverts.

15:52 Working for Home Partners of America.

26:05 Bob's transition into the Air Filter industry!

30:36 Bob's Air Filter program explained.

38:19 Other benefits of the Air Filter program.

43:05 New Initiatives and Products coming from Second Nature!

44:15 What is Bob's competitive advantage?

44:49 One piece of advice for new investors.

45:28 What do you do for fun?

46:41 Good book, podcast, or self development activity that you would recommend?

47:17 Local Network Recommendation?

48:00 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 250: Unlocking Success by Establishing a Strong Focus in Chicago Real Estate with Jonathan Klemm Oct 12, 2023

Show notes

Chicago General Contractor and return guest Jonathan Klemm provides insight on successes and improvements made to his Business and Investments since his last appearance!

Jonathan kicks things off with tremendous insights on Chicago construction including permits, renovations, new construction, and lessons learned. He discusses his recent acquisitions and shares how he sourced and stabilized those assets. He then jumps into turning down opportunities to focus on more important aspects of his business; learning to say "no" to opportunities can be extremely powerful! Jonathan emphasizes the importance of taking action, cultivating strong focus, and transparency to take your business to the next level!

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

Guests: Jonathan Klemm, Quality Builders

Link: Quality Builders' Instagram

Link: Tom Moore (Zoning Attorney Referral)

Link: The Power of Now (Book Recommendation)

Link: Think Like a Monk (Book Recommendation)

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Guest Questions

02:18 Housing Provider Tip: Be aware of wiring best practices and scams!

04:37 Intro to our guest, Jonathan Klemm!

06:52 Jonathan's messy flip project.

09:01 When are building permits required?

14:29 Dealing with Asbestos.

19:14 Getting into ground up construction!

24:38 Jonathan's 1031 exchange and establishing a focus.

29:10 Getting into a 19-unit building.

32:03 Transitioning into a 26-unit building!

35:20 Focusing on Quality Builders (Jonathan's business)!

44:50 5-Year outlook on Quality Builders and the City of Chicago!

48:18 What is Jonathan's competitive advantage?

48:58 One piece of advice for new investors.

49:58 What do you do for fun?

50:35 Good book, podcast, or self development activity that you would recommend?

51:21 Local Network Recommendation?

51:51 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 249: Fannie Mae's Departure From Needing 25% Down on 2-4 Units Oct 10, 2023

Show notes

What are the new changes to owner-occupied conventional lending and how can Chicago investors take advantage of them?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Chris Puleo, Puleo Group

Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo

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Production House: Flint Stone Media

Episode 248: Early Investing Pitfalls and Tremendous Lessons Learned in Chicago's South Suburbs with Alex Fenske Oct 05, 2023

Show notes

Alex shares how he got interested in real estate investing and bought into "guru" advice which did NOT serve him well! He dives deep into the compounding mistakes he made as a new investor including lack of focus and education and working with an inexperienced team. Alex discusses raising and losing private capital which lead to intense stress, difficult conversations, and severed relationships with friends and family. The silver lining is that Alex provides great lessons learned, advice, and closes with how he's rebounded and built a nice investment portfolio! His story is proof of the importance of getting educated and building a team to minimize risk in REI!

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

Guests: Alex Fenske, KW Chicago Southland Homes

Link: Atomic Habits (Book Recommendation)

Link: Gary Davidson (SUCI Ep 79)

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Guest Questions

02:52 Housing Provider Tip: Be cautious of potential damage caused by hydro-jetting sewer lines?

05:00 Intro to our guest, Alex Fenske!

08:02 Alex's real estate journey since starting in 2000.

20:25 Early acquisitions pre-crash!

26:55 Mindset to continue after early failures.

33:25 Rebounding from failures and getting licensed!

42:34 Alex's current investment areas of focus.

51:40 5-Year outlook on the south suburbs.

53:08 What is Alex's competitive advantage?

54:10 One piece of advice for new investors.

56:12 What do you do for fun?

56:42 Good book, podcast, or self development activity that you would recommend?

57:14 Local Network Recommendation?

58:34 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 247: Strategic House Hacking in Chicago's West Town Neighborhood with Sarita Scherpereel Sep 28, 2023

Show notes

Sarita Scherpereel is a successful realtor and investor with a focus on House Hacking to help her clients build investment portfolios!

Sarita jumps right in by sharing how she got started in real estate, built her business, and chose House Hacking as an area of focus. She shares tremendous value on how to analyze House Hacks and debunks several myths commonly associated with this strategy. Sarita discusses acquisitions utilizing multiple strategies including short-term, mid-term, and long-term rentals; all within the same property! Throughout the show, Sarita emphasizes the importance of surrounding yourself with a great team to do the first deal right and set yourself up for growth!

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

Guests: Sarita Scherpereel, Kale Realty

Link: Sarita's Instagram

Link: SUCI Ep 238 - Mike Facchini

Link: First Ascent Climbing & Fitness

Link: The Power of Now (Book Recommendation)

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Guest Questions

04:56 Housing Provider Tip: Keep up with HVAC system servicing as preventative maintenance!

07:13 Intro to our guest, Sarita Scherpereel!

08:38 Sarita's start in real estate.

16:13 Choosing House Hacking as a niche!

23:57 Best activities for new Realtors to build their business!

28:33 Debunking the myths of House Hacking!

33:10 Mid-Term Rentals and Furnished Finder!

40:38 House Hacking in West Town.

45:28 Outlook on West Town.

48:25 What is Sarita's competitive advantage?

49:41 One piece of advice for new investors.

50:08 What do you do for fun?

50:55 Good book, podcast, or self development activity that you would recommend?

52:41 Local Network Recommendation?

54:09 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 246: How to Get Reimbursed For Damages From Recent Chicago Flooding Sep 26, 2023

Show notes

How can I get reimbursed for damages that occurred to my property from the recent Chicago floods?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guests: Jason Wagner, Greystone Realty

Link: DisasterAssistance.gov

Link: Disaster Loan Assistance

Link: SUCI Episode 224: Expert Insights On Chicago's Northwest Side with Jason Wagner

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Production House: Flint Stone Media

Episode 245: Insights to Successful Short-Term Rental Investments with JD Modrak Sep 21, 2023

Show notes

JD shares his real estate beginnings, including his purchase of a multi-family building with a VA loan. He dives into Short-Term Rentals (STRs) including income, expenses, and how those compare to traditional rentals. JD gets granular on STR pricing, occupancy, turn-over costs, and optimizing profitability. He drops golden nuggets on common mistakes investors make in STR investing and how you can avoid those! This show is packed with jewels of wisdom for anyone interested in STR investing!

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

Guests: JD Modrak, Kasa

Link: Andrew Dorazio (Network Referral)

Link: Our Team | BCG Real Estate Group

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Guest Questions

02:09 Housing Provider Tip: Have an HVAC contractor for emergency repairs during extreme weather!

04:22 Intro to our guest, JD Modrak!

05:22 JD's start with Short-Term Rentals (STRs)!

08:21 STR Expenses and Net Income.