311 episodes
Straight Up Chicago Investor Straight Up Chicago Investor
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5.0 • 258 Ratings
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Are you a real estate investor in Chicago or someone looking to invest in the Chicagoland Market? If so, this podcast is for you! We break down the neighborhoods, different sides of the city, and surrounding suburbs so you can understand the uniqueness of investing in Chicago real estate.
The hosts and guests are Chicago investors and Property Managers who are making it happen in and around the Windy City. We share information, winning strategies, obstacles, success stories, and most importantly, lessons learned. If you are looking for ground level information and want to learn what has worked and not worked in Chicago, you are in the right place.
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Managing and Operating 100+ Units at 25 Years Old with James Thompson
James Thompson is broker and property manager with vast experience acquiring, renovating, and managing apartment buildings all at the young age of 25 years old!
James shares the early grind required to get off the ground in the commercial real estate game! He discusses the biggest lessons learned from renovating and managing 100+ apartments. James gives the scoop on investing in student housing and also provides some good REI horror stories. James closes with great advice for newer investors and a positive outlook on Chicago!
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: James Thompson, Triton Realty Group
Link: SUCI Ep 22 - Matt Fritzshall (Network Referral)
Link: Morning Brew Daily (Podcast Recommendation)
Link: Jay Parsons (Rental Housing Economist)
Link: Jay Martin - Article on Rent Control Drawbacks
Guest Questions
03:30 Housing Provider Tip - Be aware of required inspections when replacing hot water heaters!
05:36 Intro to our guest, James Thompson!
09:37 The grind of starting in commercial real estate.
17:22 Biggest lessons learned from construction and management of buildings!
22:50 The 101 on student housing.
26:32 Growing the management company and horror stories!
35:15 Advice for new and aspiring investors.
37:07 James’ outlook on Chicago.
43:55 What is your competitive advantage?
44:27 One piece of advice for new investors.
44:57 What do you do for fun?
45:08 Good book, podcast, or self development activity that you would recommend?
45:37 Local Network Recommendation?
46:16 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. -
Guidelines Investors Can Utilize To Estimate Rehab Costs
What Are Some High-Level Guidelines Chicago Investors Can Leverage to Estimate Rehab Costs?
Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: StraightUpChicagoInvestor@gmail.com
Guests: Jonathan Klemm, Quality Builders
Link: Episode 76: Big Business Processes Make a Powerful Small Business with Jonathan Klemm
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2024. -
How To Build a Community of Experts and Influencers with Tony Arce
Tony Arce and his Team at The Face of Community & Business provide a media platform for leaders in business to connect, teach, and grow together.
Tony starts by sharing how he discovered his passion for media and creating human-to-human connections not only in his personal life but in business. He explains how this passion sparked the idea of creating The Face of Community & Business (TFOCB); a media platform that allows for the creation of professional communities across different businesses. Tony discusses the importance of building a brand and influence to set your business up for success. Throughout the episode, Tony shares great insights on being a connector and creating business communities.
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: Tony Arce, The Face of Community & Business
Link: TFOCB's Instagram
Link: Never Split the Difference (Book Recommendation)
Link: LaQuan Henley (Network Referral)
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Guest Questions
02:31 Housing Tip Limit your vacancy by pricing your units appropriately to end this leasing season!
04:35 Intro to our guest, Tony Arce!
11:32 The Creation of TFOCB.
19:38 Common mistakes when building a business and a brand!
25:07 Creating a platform for content creators and influencers.
33:05 The Importance of Events for Building a Community.
45:53 What’s next for Tony?
50:21 What is your competitive advantage?
50:48 One piece of advice for new investors.
51:36 What do you do for fun?
52:18 Good book, podcast, or self development activity that you would recommend?
53:06 Local Network Recommendation?
53:49 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. -
D1 Athlete’s Journey: From Immigrant to Finance Mentor with Alex Filin
Alex Filin is a seasoned Loan Office, Coach, and Investor with over $385 Million in funded loans!
Alex shares his upbringing as an immigrant in America, experiences that cultivated grit, and his journey to becoming a D1 football player! He discusses his successful career shift to mortgage lending where he closed $95 million in funded loans in the first 5 years. Alex emphasizes the importance of having mentors, being coachable, and surrounding yourself with people you want to be like. Alex closes with empowering words on “getting into the game” now and having integrity in business and in 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
Guests: Alex Filin, Vybe Mortgage
Link: Alex's Instagram
Link: Growth Only Coaching
Link: SUCI Ep 205 - Nick Chaplain (Life Insurance)
Link: Horacio Tristan (Network Referral)
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Guest Questions
02:33 Housing Provider Tip - Prevent wire fraud by calling the title company to confirm wire instructions.
04:51 Intro to our guest, Alex Filin!
18:48 Alex’s career shift to mortgage lending!
22:18 Tips to get started in real estate.
28:20 How to be coachable.
34:04 Alex’s start to investing!
44:27 Alex’s 10 year forecast in real estate.
47:57 What is your competitive advantage?
48:57 One piece of advice for new investors.
49:49 What do you do for fun?
50:48 Good book, podcast, or self development activity that you would recommend?
51:38 Local Network Recommendation?
52:07 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 2024. -
Steps For Investors To Take During the Tax Off-Season
What Steps Should Investors Take During the Tax-Offseason to Minimize Tax Liability?
Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: StraightUpChicagoInvestor@gmail.com
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 2024. -
Drugs, Death, and Big Mistakes Never Spoken Of With Mark Ainley
The tables turn this week as Mark Ainley gets interviewed by Tom Shallcross, returning the favor from Episode 235 (episode link in show notes)!
Tom starts by asking Mark about his childhood and upbringing; spoiler alert - there is mention of Mark’s frosted-tips phase while vacationing in Mexico!! Mark breaks down his start in real estate, the genesis of GC Realty & Development, and the early REI ventures that he and his business partner Bryan took on. He discusses his experience with repositioning office buildings and industrial investments displaying the range of his investing journey. Mark closes with tremendous insights on his most recent project involving rehabbing of a residential property and partnering up with a younger investor. This episode is full of golden nuggets and funny stories that you won’t 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!
Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: StraightUpChicagoInvestor@gmail.com
Guests: Mark Ainley, GC Realty & Development
Link: Mark's Instagram
Link: SUCI Ep 235 - Tom Shallcross
Link: John Warren's Meetup
Link: NBOA - 2024 Summer Soiree
Link: Bibek Das (Network Referral)
Link: The Psychology of Money (Book Recommendation)
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Guest Questions
04:15 Intro to our special guest, Mark Ainley!
15:04 The Genesis of GC Realty!
19:50 GC Realty’s shift to property management.
21:55 Navigating the Housing Crash.
39:23 Shift to industrial investments.
48:00 Jumping back into rehabbing properties!
61:11 What is your competitive advantage?
61:38 One piece of advice for new investors.
62:08 What do you do for fun?
63:05 Good book, podcast, or self development activity that you would recommend?
64:04 Local Network Recommendation?
64:46 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 2024.
Customer Reviews
Awesome Local Chicago Podcast
We needed a local podcast that gives us local Chicagoan’s a glimpse. On how other local Chicagoan’s are navigating the Chicago real estate investment market.
Great Podcast
Love the very tactical and insightful discussion topics and guests they bring on.
The Best
This podcast provides a truly unbelievable amount of value, resources, and knowledge to anyone interested in investing in Chicago RE. This is an Ivy League education for free right here. Mark and Tom are extremely experienced and the fact that they're putting this out there for listeners to take advantage of is seriously incredible. Thank you guys so much. Can’t tell you how much I’ve learned and how much I enjoy the podcast.