Straight Up Chicago Investor

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.

Straight Up Chicago Investor is a business podcast hosted by Unknown Host, with 0 episodes on record and a Required Pod Score of 80.

Unknown Host hosts Straight Up Chicago Investor, a business show with 0 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #480

  Episode 480: Senior Housing Sector: Underwriting, Markets, and Opportunities with Mark Myers

  Sep 24, 20261h 7m

  Mark Myers of Kiser Group joins us to share insights from over three decades of experience in senior housing investments and brokerage! Mark starts with how he got involved with senior housing and the evolution of the asset class over the last 30 years! He shares the basics of senior housing underwriting and compares the operations and returns to multifamily investing. Mark gives a detailed breakdown on expenses, risks, and regulations to be considered when investing in this asset class. He closes the show with advice on getting off the ground as a new senior housing investor or broker and provides a very bullish market outlook! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= C onnect 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 ============= Guest: Mark Myers, Kiser Group Link: Crime and Punishment (Book Recommendation) Link: The SeniorCare Investor Link: NIC Website Link: ASHA Website Guest Questions: 02:08 Housing Provided Tip - Remember to follow the law and change locks after tenant turnovers! 04:01 Intro to our guest, Mark Myers! 12:15 The evolution of senior housing! 17:38 The state of the senior housing market. 20:00 Underwriting basics for senior housing. 32:23 Comparing multifamily to senior housing investments. 38:07 Rules and regulations to be aware of. 45:11 Identifying hot markets and how to get in the game! 50:18 Getting off the ground as a senior housing broker. 55:35 Mark's outlook on the senior housing market! 57:37 What's your competitive advantage? 58:42 One piece of advice for new investors. 59:26 What do you do for fun? 61:19 Good book, podcast, or self development activity that you would recommend? 62:00 Local Network Recommendation. 63:13 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

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  Episode #479

  Episode 479: Finding Cash Flow in Chicago's A Class Neighborhoods with David Shifrin

  Sep 17, 202650 min

  David Shifrin of Elite Properties Chicago returns to share how he has scaled his portfolio since his last SUCI podcast appearance in 2024! David opens up by summarizing his portfolio and how he created cash flow in premier Chicago neighborhoods! He breaks down how a 1031 exchange works and gets granular with an example that led to the acquisition of a great multifamily asset in Avondale. David shares some lessons learned from a rough rehab project and talks about strategies to raise rents and property value without having to do significant renovation. He closes with his take on current investment opportunities in West Town and a bullish outlook on Chicago 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! ============= C onnect 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 ============= Guest: David Shifrin, Elite Properties Chicago Link: SUCI Ep 280 - David Shifrin Link: David Shifrin's Bio Link: NBOA Chicago Link: Illini Inquirer Podcast Guest Questions: 02:00 Housing Provided Tip - Consider a sump pump system to protect your properties during heavy rain falls! 03:12 Intro to our guest, David Shifrin! 05:40 Finding cash flow in class A neighborhoods. 08:00 Breaking down 1031 exchanges. 11:41 David's recent Avondale multifamily deal! 15:22 Pros and cons of paying down mortgages. 25:14 David's top lessons learned from rapidly building a portfolio. 29:24 Opportunities to be had in West Town. 40:06 David's outlook on Chicago! 44:20 What's your competitive advantage? 44:34 One piece of advice for new investors. 45:00 What do you do for fun? 45:42 Good book, podcast, or self development activity that you would recommend? 46:44 Local Network Recommendation? 47:27 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

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  Episode #478

  Episode 478: The Proposed Move Act: Where Owners Can Transfer Their Existing Mortgage

  Sep 15, 202616 min

  What do investors need to know regarding the proposed legislation for both the Road To Housing and Move Act? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Chris Puleo, Puleo Group Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

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  Episode #477

  Episode 477: Building an 80-Unit Portfolio in 2 Years with Arthur Barkan

  Sep 10, 20261h 3m

  Arthur Barkan of Barkan Realty joins us to share how he rapidly scaled his multifamily portfolio to 80 units! Arthur breaks down the ins and outs of investing in North Chicago, current market deal flow, and evaluating troubling tenants and potential evictions! He also shares strategies for scaling faster, tools to improve property management operations, and lessons learned from working with villages in the northern suburbs. Arthur gets granular on financing properties, capital recycling through refinances, and evaluating cash flow vs long-term net worth. He closes with his five-year vision to continue rapidly scaling his portfolio! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= C onnect 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 ============= Guest: Arthur Barkan, Barkan Realty | Call Arthur: 224-433-4553 Link: Arthur's Instagram Link: Real Life Investing Podcast with Arthur Barkan Guest Questions: 02:43 Housing Provider Tip - Understand cost segregation implications if planning to sell a property in the near term. 03:28 Intro to our guest, Arthur Barkan! 08:40 The ins and outs of North Chicago. 17:26 Assessing a potential eviction scenario. 26:17 Deal flow in today's market. 33:12 Strategies to scale faster! 36:53 Tools to streamline property management. 44:40 Dealing with the Village of North Chicago. 51:39 5 Year Outlook on Arthur's business! 57:37 What's your competitive advantage? 57:53 One piece of advice for new investors. 58:01 What do you do for fun? 58:22 Good book, podcast, or self development activity that you would recommend? 59:15 Local Network Recommendation? 59:23 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

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  Episode #476

  Episode 476: Jake Rome on Leverage, Underwriting, and the Future of Real Estate Financing: How Backflip Is Revolutionizing Fix & Flip Lending

  Sep 3, 20261 hour

  Jake Rome, co-founder of Backflip, joins us to share the wild journey from institutional real estate private equity to building a vertically integrated lending platform for fix-and-flip investors! Jake breaks down the return-on-equity math that makes single-family flips so powerful, then digs into the leverage and risk decisions that separate successful investors from those who blow up their portfolios. He explains why Backflip decided to service and securitize its own loans, what red flags show up in underwriting (wholesaler markups, seller concessions), and how Chicago's Cook County foreclosure timeline uniquely impacts local lending. Jake also shares his outlook on where the fix-and-flip capital markets are headed, plus how he's using AI to run his own real estate portfolio. If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= C onnect 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 ============= Guest: Jake Rome, Backflip Connect with Backflip: LinkedIn | Instagram | Careers Link: Ready to fund your next deal? Apply with Backflip here . Guest Questions: 02:07 – Housing Provider Tip: What to do when a tenant stops paying rent 04:04 – Intro to our guest, Jake Rome of Backflip! 06:07 – From institutional real estate private equity to startups 13:44 – How the idea for Backflip was born 19:25 – Breaking down return on equity on a fix and flip 23:27 – Understanding leverage, risk, and how much is too much 28:09 – Building Backflip: raising capital and servicing their own loans 34:13 – Underwriting red flags: wholesaler markups & seller concessions 39:17 – Where Backflip lends, and the Cook County foreclosure timeline 44:36 – Red flags for first-time construction loan borrowers 46:39 – What lenders actually look for: credit score, experience, liquidity 51:10 – Building community: closing dinners and "Burgers and Flips" 53:19 – The future of fix-and-flip lending and securitization 56:08 – Competitive advantage & advice for new investors 57:53 – How listeners can learn more about Jake and Backflip ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

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