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.

Episode 332: From Slangin’ Windows To Building Chicago 6 Flats in 10 Year with Joey Halperin 10/31/2024

Episode 331: These Neighborhoods Have the Most Potential for Chicago Investors 10/29/2024

Episode 330: Condo Conversions, Building Violations, and How to Stay Compliant with the New CTA with James Erwin 10/24/2024

Episode 329: From W2 To Investor Overnight… See How This Played Out For Sean Douglas 10/17/2024

Episode 329: From W2 To Investor Overnight… See How This Played Out For Sean Douglas Sean Douglas of the Axon Group discusses his adventurous start to his real estate journey! Sean began his investment career when he inherited his grandparent’s home, which after numerous setbacks, he eventually flipped! He breaks down how he jumped into the deep end by doing construction himself. After having a contractor steal $7000 from him, Sean recaps the long days of work that it took to get his flip project to the finish line. Sean also shares details on his 4-unit house hack and considerations when investing in “picky” towns and villages. Throughout the show, Sean demonstrates how his perseverance and discipline have allowed him to get past difficult situations and become a stronger investor and person! 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: Email the Show: Guest: Sean Douglas, Link: Link: Link: Link: Link: Guest Questions 02:19 Housing Provider Tip - Be aware of permit and inspection requirements from municipalities! 04:48 Intro to our guest, Sean Douglas! 09:06 Sean’s start in investing. 11:54 Inheriting your grandparent’s home. 15:03 Leveraging BiggerPockets to find resources! 21:22 Early (goofy) mistakes and learning construction. 28:29 Disposition of crazy flip project! 32:56 Life post flip project. 40:04 Sean’s 4-unit house hack adventure. 49:17 From real estate inspector to broker. 58:23 What is your competitive advantage? 58:53 One piece of advice for new investors. 59:14 What do you do for fun? 59:22 Good book, podcast, or self development activity that you would recommend? 60:15 Local Network Recommendation? 60:56 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2024. /episode/index/show/straightupchicagoinvestor/id/33488037

Episode 328: What to Focus on When Negotiating A Multifamily Transaction 10/15/2024

Episode 327: Logan & Humboldt Property Owners’ Rights Taken By The New NW Preservation Ordinance with Luke Blahnik 10/10/2024

Episode 327: Logan & Humboldt Property Owners’ Rights Taken By The New NW Preservation Ordinance with Luke Blahnik Luke Blahnik returns to educate us on the new Northwest Side Preservation Ordinance. Luke jumps right in by explaining the ins and outs of the expansion of the Predominance of the Block (606) District under this new ordinance. He breaks down the increased fees to demolish a multi-unit building, limitations on building single family homes, and requirements for selling a tenant-occupied building in the area. Luke, Mark, and Tom discuss how the Ordinance will not be able to accomplish the goal of preserving affordable housing and instead could have negative impacts to landlords and tenants. A main takeaway from today’s show is to stay involved in housing provider communities and make your voice heard to stop policies that do not help landlords, tenants, and/or the City of Chicago as whole. If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! ============= 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: Email the Show: Guest: Luke Blahnik, Link: Link: Link: Link: Guest Questions 03:13 Housing Provider Tip - Stay involved in your community so your voice is heard. 04:53 Intro to our guest, Luke Blahnik! 05:27 The “Northwest Preservation Ordinance” Explained. 19:32 Exemptions for the Ordinance. 19:10 Benefits of raising capital and passive investments! 22:40 Groups most impacted by the Ordinance. 36:28 What’s next following the implementation of the Ordinance? 39:49 What is your competitive advantage? 40:24 One piece of advice for new investors. 40:42 What do you do for fun? 41:18 Good book, podcast, or self development activity that you would recommend? 41:46 Local Network Recommendation? 42:31 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2024. /episode/index/show/straightupchicagoinvestor/id/33391572

Episode 326: How This Chicago Investor Grew 10x in Just 3 Years with RJ de Leon 10/03/2024

Episode 326: How This Chicago Investor Grew 10x in Just 3 Years with RJ de Leon RJ de Leon returns to the show to tell us about his most recent investments and how he’s managing his portfolio remotely as he and his family spend most of the year traveling! RJ starts by discussing how he and his wife Nicky set up their investments and businesses to be able to manage them remotely and travel the country for months at a time! He gives tips for aspiring entrepreneurs that are planning to embark on a new journey. RJ explains all the benefits and considerations of passive investments and gets granular on analyzing investments. He also provides insights on capital raising and alternative investments beyond real estate that can allow you to work smarter, not harder. Throughout the show, RJ emphasizes the power of networking and being a “go-giver” to create your own luck! If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! ============= 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: Email the Show: Guest: RJ de Leon, Link: Link: Link: Link: Link: Link: Guest Questions 04:08 Intro to our guest, RJ de Leon! 08:24 Getting into Capital Raising. 17:06 Preparation tips for embarking on a new journey! 19:10 Benefits of raising capital and passive investments! 25:51 The Power of Networking. 28:13 Analyzing a passive investment. 32:27 Accepting capital from investors. 38:18 RJ’s next trip and getting educated on alternative investments. 44:44 What is your competitive advantage? 45:13 One piece of advice for new investors. 46:21 What do you do for fun? 47:09 Good book, podcast, or self development activity that you would recommend? 47:54 Local Network Recommendation? 48:44 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2024. /episode/index/show/straightupchicagoinvestor/id/33297122

Episode 325: How Much Does it Cost to Construct an ADU in Chicago? 10/01/2024

Episode 324: How to Combat Squatters and Title Deed Fraud with George McCleary 09/26/2024

PW Cabinetry Grand Opening 09/23/2024

Episode 323: Leveraging a W2 to Grow a Chicago Portfolio and Brokerage with Horacio Tristan 09/19/2024

Episode 323: Leveraging a W2 to Grow a Chicago Portfolio and Brokerage with Horacio Tristan Horacio Tristan is a born and raised Chicagoan and full-time government employee who has built an impressive real estate portfolio and brokerage business! Horacio starts by discussing his upbringing and his first few real estate deals on Chicago’s South Side. He explains how he built and maintained his real estate brokerage business during the housing crash. Horacio shares his geographic areas of focus and numbers-driven investment strategy. He discusses being an efficient real estate broker and how that has allowed him to succeed in brokerage while having a W2 job. In classic SUCI fashion, Horacio closes with a bullish 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! ============= 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: Email the Show: Guest: Horacio Tristan, Link: Link: Link: Link: Guest Questions 03:00 Housing Provider Tip - Be aware of the Chicago Heat Ordinance as a Housing Provider. 04:10 Intro to our guest, Horacio Tristan! 08:40 Horacio’s first few deals. 17:28 Navigating the Housing Crash. 28:40 Dealing with a distressed condo building. 31:47 Horacio’s investing strategy today! 38:00 Being a successful broker with a W2 job. 40:30 What’s next for Horacio? 44:58 The future of Chicago! 46:45 What is your competitive advantage? 47:25 One piece of advice for new investors. 47:50 What do you do for fun? 48:06 Good book, podcast, or self development activity that you would recommend? 48:30 Local Network Recommendation? 48:37 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2024. /episode/index/show/straightupchicagoinvestor/id/33106892

Episode 322: FHA Financing vs 5% Down; Pros and Cons For Each Option With Perry Farella 09/17/2024

Episode 321: Flipping, Short-Term Rentals, & Helping Veterans Secure Housing with Kirby Atwell 09/12/2024

Episode 321: Flipping, Short-Term Rentals, & Helping Veterans Secure Housing with Kirby Atwell Kirby Atwell is a former US Army Officer turned real estate investor and podcast host with a focus on short-term rentals! Kirby starts with his experience in the military and jumping into real estate shortly after reading “Rich Dad, Poor Dad”! With over 100 renovated properties under his belt, he shares great insights on small and large flips including pros and cons of both options. Kirby discusses the midwest markets that he focuses on to maximize cash flow and how experimenting with a basement short-term rental led him to change his focus to STRs! He sprinkles in some STR horror stories and closes with a bullish take on owning vacation rentals in Michigan City. If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! ============= 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: Email the Show: Guest: Kirby Atwell, Link: Link: Link: Guest Questions 01:40 Housing Provider Tip - Take the CIC property management class! 03:56 Intro to our guest, Kirby Atwell! 11:04 Kirby’s first couple properties! 15:27 Kirby’s return to Chicago after the military! 19:22 Comparing small vs large flips. 26:12 Getting aggressive on acquisition. 32:34 Building a cash flow for financial freedom! 38:09 Experimenting with Short Term Rentals. 45:52 STR horror stories! 50:40 Deal flow in Michigan City. 56:28 Starting a podcast. 59:00 What is your competitive advantage? 60:07 One piece of advice for new investors. 61:06 What do you do for fun? 62:40 Good book, podcast, or self development activity that you would recommend? 63:40 Local Network Recommendation? 64:31 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2024. /episode/index/show/straightupchicagoinvestor/id/33010987

Episode 320: The Godfather of Chicago Property Management, Taft West 09/05/2024

Episode 320: The Godfather of Chicago Property Management, Taft West Taft West is the Vice President of Technical Assistance and Sustainability for the Chicago Community Loan Fund and is a renown property management instructor! Taft starts by sharing his background which includes some autopsy experience! He talks about starting in Chicago real estate, managing condominiums, and public housing in the late 1970s. Taft discusses the differences in leasing now compared to 40 years ago! He drops golden nuggets on the biggest mistakes landlords make and screen out bad tenants. Taft closes with powerful words on doing good work for your community to make a difference! Celebrate Taft: Are you one of the many owners who took one of Taft’s classes? You can express your gratitude to Taft in-person on October 17th. He is being recognized by the Law Center for Better Housing for his work educating tenants and landlords about how to work together to build community. Learn more and celebrate Taft here: ============= 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: Email the Show: Guest: Taft West & Jared Kott, Link: Link: Link: Guest Questions 01:45 Intro to our guest, Taft West and Jared Kott! 03:33 Taft’s backstory! 19:01 Taft’s transition into property management. 28:00 Leasing apartments back in the 1970s! 37:23 How Taft started working with CIC! 45:03 Biggest mistake landlords make. 54:52 Building a Community! 61:30 What is your competitive advantage? 62:50 One piece of advice for new investors. 63:46 What do you do for fun? 66:22 Good book, podcast, or self development activity that you would recommend? 67:24 Local Network Recommendation? 68:21 How can the listeners learn more about you and provide value to you ----------------- Production House: Copyright of Straight Up Chicago Investor 2024. /episode/index/show/straightupchicagoinvestor/id/32895932

Episode 319: Great Tips on How To Manage Your Contractors 09/03/2024

Episode 318: How to 4X Your Real Estate Business with Michael Valente 08/29/2024

Episode 318: How to 4X Your Real Estate Business with Michael Valente Michael Valente is the founder and CEO of Renovation Sells Franchising; general contracting experts that focus on cosmetic renovations of pre-market homes to maximize sales price! Michael shares how he left his corporate job and began working for his mentor to learn the ropes of general contracting and renovation! He talks about starting his own general contracting business and the biggest lessons learned as he grew his business. He breaks down the genesis of Renovation Sells; his general contracting company that focuses on cosmetic renovations of pre-market homes so sellers can get top dollar! Michael dives into how he franchised his business and the most critical considerations in this process. Throughout the show, Michael emphasizes the importance of networking and largely attributes that 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: Email the Show: Guest: Michael Valente, Link: Link: Guest Questions 02:12 Housing Provider Tip - Ensure your units are priced correctly to find a renter before the end of leasing season. 04:30 Intro to our guest, Michael Valente! 09:02 Getting a General Contracting business off the ground! 15:38 Leaving a mentor to start your own business. 21:11 The idea of franchising a business. 30:01 How the franchise model works. 37:44 Biggest mistakes Michael made scaling his business. 43:08 Michael’s pre-COVID Pilsen building! 46:37 Goals for the Renovation Sells franchise! 49:16 Top networking tips! 51:53 What is your competitive advantage? 52:41 One piece of advice for new investors. 53:10 What do you do for fun? 53:23 Good book, podcast, or self development activity that you would recommend? 54:32 Local Network Recommendation? 55:48 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2024. /episode/index/show/straightupchicagoinvestor/id/32776857

Episode 317: Kevin Dugan Does It From 2,000 Miles Away… What Excuse Do You Have? 08/22/2024

Episode 317: Kevin Dugan Does It From 2,000 Miles Away… What Excuse Do You Have? Kevin Dugan is the Managing Principal of Altus Investment Group. He runs multiple businesses that successfully operate in Chicago while managing them remotely from Los Angeles! Kevin starts by talking about the skills he gained working on oil rigs and as a sales engineer and how that translated to real estate! He breaks down his first flip in South Shore and the process of managing that project from Los Angeles! Kevin dives deep into the challenges of managing rentals and growing a business remotely. He emphasizes hiring good people and building a construction arm as critical pieces for a thriving REI investment company. Throughout the episode, Kevin shares his firm belief in cultivating the “Who, Not How” mentality and building a great team! 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: Email the Show: Guest: Kevin Dugan, Link: Link: Link: Guest Questions 02:37 Housing Provider Tip - Ensure your apartments are turned over to a nice condition especially on higher priced units. 04:04 Intro to our guest, Kevin Dugan! 10:04 Starting with a South Shore flip and managing it from California! 14:28 Transitioning to investments in the south suburbs. 22:04 Obtaining financing for stabilized rental properties. 27:04 The process and mindset for starting a business! 33:44 Struggles with managing rentals from out of state. 38:00 How to grow a business remotely. 47:55 One decision that Kevin would change in his trajectory. 53:54 What is your competitive advantage? 54:13 One piece of advice for new investors. 54:29 What do you do for fun? 54:43 Good book, podcast, or self development activity that you would recommend? 55:13 Local Network Recommendation? 56:04 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2024. /episode/index/show/straightupchicagoinvestor/id/32677832