Best Straight Up Chicago Investor Podcasts (2025)

1
Episode 377: This is How Grit Can Take You Further in Chicago Real Estate with Daniel Baker 55:27

2d ago55:27

55:27

Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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…

1
Elon Musk meets with Pres. Trump in Oval Office, reflects on DOGE legacy, on last day as Special Government Employee 50:48

4h ago50:48

50:48

Elon Musk, Former head of Department of Government Efficiency (DOGE) joins the President Trump in the White House Oval Office on his final day as a government employee; President Trump accuses China of violating a trade agreement from a few weeks ago that led to the lowering of high tariffs on both sides while negotiations continued on a longer-ter…

1
White House criticizes 'activist judges' after federal trade court decision to strike most of Pres. Trump's tariffs as unlawful; federal appeals court reinstates tariffs, for now 53:42

1d ago53:42

53:42

White House is calling on the Supreme Court to intervene after a federal trade court struck down many of President Donald Trump's tariffs because the president exceeded his legal authority when he put them in place. Press Secretary Karoline Leavitt say, "America cannot function if President Trump, or any other president for that matter, has their s…

1
President Trump rejects TACO (Trump Always Chickens Out) meme on his tariff strategy, saying, 'It's called negotiation' 55:01

2d ago55:01

55:01

President Donald Trump responds to a nickname some on Wall Street have given him to describe his tariff policy that includes the word 'chicken'; President is asked about Elon Musk saying he disappointed with the amount of spending in the budget reconciliation 'one big beautiful bill' passed by the House; Transportation Secretary Sean Duffy calls fo…

1
King Charles III opens Canada's parliament, saying 'the True North is indeed strong and free', amid Pres. Trump threats of annexation 50:32

3d ago50:32

50:32

Great Britain's King Charles III opens the Canadian parliament in Ottawa by declaring, "As the anthem reminds us, the True North is indeed strong and free." Associated Press calls it "a speech widely viewed as a show of support in the face of annexation threats by U.S. President Donald Trump"; on Wall Streets, stocks climb after President Trump say…

1
Episode 376: Buy Before You Sell; How To Write Offers Non-Contingent on The Sale of Your Existing Property 10:20

4d ago10:20

10:20

Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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…

1
Weekend Edition: Trump Administration changes to public health, Energy Initiatives and the "Big, Beautiful Bill" and Immigration Enforcement 30:26

6d ago30:26

30:26

In this weekend's episode, three segments from this past week's Washington Journal. First, a conversation with Dr. Georges Benjamin of the American Public Health Association. We'll talk about changes the Trump administration is making to public health, under the leadership of HHS Secretary Robert F. Kennedy Jr. Then, Congressional Republicans and P…

1
Federal judge blocks Trump Admin. ban on Harvard enrolling international students; Pres. Trump threatens high tariffs on European Union & Apple's iPhones 43:25

7d ago43:25

43:25

A federal judge puts on hold the Trump Administration order to Harvard not to accept any international students after the school refused to turn over information about those students' political activities; President Donald Trump threatens to impose a 50% tariff on the European Union and a 25% tariff on smartphones from Apple and Samsung not made in…

1
House passes 'One Big Beautiful Bill" by one vote; bipartisan condemnation of deadly shooting of two Israeli Embassy staffers in DC 53:29

8d ago53:29

53:29

House Republicans pass the budget reconciliation 'one big beautiful' tax cut and spending cut bill by one vote after an all-night debate and daybreak vote; FBI is investigating as an 'act of terror' the shooting death of two Israeli Embassy aides outside the Capital Jewish Museum in Washington, DC by a man who shouted "free, free Palestine"; Make A…

1
Episode 375: Learn How To Build A Chicago Portfolio Without Quitting the W2 with Nate Fernandez 52:05

9d ago52:05

52:05

Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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…

1
Speaker Johnson says 'plan is to move forward' on vote on budget reconciliation bill after White House meeting with Freedom Caucus 52:45

9d ago52:45

52:45

House Rules Committee meets all night and then all day on the Republican tax cut and spending cut package called Budget Reconciliation or "One Big Beautiful Bill", but negotiations continue among Republicans to reach the near-unanimity that will be need to pass it through the House without any Democratic votes; Education Secretary Linda McMahon tes…

1
President Trump meets with House GOP on budget reconciliation bill, but SALT Caucus & Freedom Caucus still holding firm in their demands 54:26

10d ago54:26

54:26

President Donald Trump meets with House Republicans on the Budget Reconciliation bill, urging those opposed to accept what is being offered and not to push for additional spending cuts or more state & local tax deduction, but it is uncertain whether he convinced enough for the bill to pass this week; Rep. LaMonica McIver (D-NJ) says felony charges …

1
House GOP leaders want Trump to dissuade hard-liners on deeper Medicaid cuts 40:42

11d ago40:42

40:42

-House Speaker Mike Johnson says the Republicans federal budget resolution still has QUOTE a lot of hurdles left following its passage out of the House Budget Committee late last night…Fox News Digital reporter Liz Elkind reported that Speaker Johnson said on a conference call this morning…. That members are facing the “most important 48 hours ahea…

1
Weekend Edition: Supreme Court Case on Birthright Citizenship. Russia-Ukraine Peace Talks, and Prescription Drug Prices 31:12

13d ago31:12

31:12

In this weekend's episode, three segments from this past week's Washington Journal. First, Wall Street Journal Supreme Court correspondent Jess Bravin breaks down the Supreme Court case heard this week on Trump administration's effort to end birthright citizenship. Then, a conversation with Maria Snegovaya of the Center for Strategic & Internationa…

1
House Republican tax cut & spending cut Budget Reconciliation fails in committee after a handful of Republicans vote 'no' 49:21

14d ago49:21

49:21

House Budget Committee votes down the Republican tax cut, spending cut, border and defense Budget Reconciliation, the one they call the One Big Beautiful Bill, after four Republicans join Democrats in voting no; President Donald Trump finishes up his Middle East trip at a business breakfast in the United Arab Emirates, saying UAE could buy advanced…

1
Supreme Court hears case on birthright citizenship and nationwide court injunctions 53:46

15d ago53:46

53:46

Supreme Court hears a case on the 14th Amendment's birthright citizenship clause, and President Trump Executive Order to redefine it to not include children born in the U.S. to undocumented immigrants, but much of the argument concerns whether nationwide court injunctions should be allowed; We hear some of the Justices' questioning and get analysis…

1
Episode 374: Taking On Opportunity In Chicago’s Toughest Neighborhoods with Corey Oliver 1:06:33

16d ago1:06:33

1:06:33

Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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…

1
Health Secretary Robert F. Kennedy, Jr. tells Congress people should not take his medical advice on vaccines 54:59

16d ago54:59

54:59

Health & Human Services Secretary Robert F. Kennedy, Jr. is questioned about vaccines at two congressional committee hearings. One Senator accuses him of lying to the committee during his confirmation about his plans for programs that promote vaccinations. House Speaker Mike Johnson (R-LA) is confident that a deal can be reached with holdout House …

1
House committees mark up Republican tax, Medicaid & SNAP changes in budget reconciliation 55:02

17d ago55:02

55:02

Biggest parts of the House Republicans' and President Trump's "One Big Beautiful Bill" get marked up in committees, but some Republicans are not satisfied with the proposals on tax cuts and Medicaid cuts, and it could put the bill in jeopardy. We will hear from Members and talk with Washington Post Congressional reporter Jacob Bogage. (1) President…

1
Episode 373: A New Option to Fund Renovations For Chicago 2-4 Properties 10:09

18d ago10:09

10:09

Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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…

1
President Trump defends accepting luxury jet from Qatar as he travels to the Middle East, and signs Executive Order aimed at lowering prescription drug prices 34:39

18d ago34:39

34:39

President Donald Trump defends his decision to accept a luxury jet from the Qatari royal family that he plans to use as Air Force One, as he travels to the Middle East. President signs an Executive Order that aims to cut prescription drug costs. House Republicans release more of their tax plan that calls for extending the 2017 tax cuts and tighteni…

1
Weekend Edition: Manufacturing in the U.S., Dept. of Education resumes collection on defaulted student loans, and Air Traffic Control Systems 36:17

21d ago36:17

36:17

In this weekend's episode, three segments from this past week's Washington Journal. First, a conversation with author Rachel Slade about her book "Making it America" about the history – and future - of manufacturing in the United States. Then, the Department of Education resumed collection on defaulted student loans this week. We speak with Rick Se…

1
Another air traffic controller outage at Newark Airport; Pres. Trump on China & tariffs; Librarian of Congress fired 47:15

21d ago47:15

47:15

FAA says air traffic controllers lost contact again for short time with flightsgoing in and out of Newark Airport; President Donald Trump suggests a new tariff level for China as Treasury Secretary Scott Bessent and USTR Jamieson Greer are about to meet Chinese officials for trade talks; White House says the Librarian of Congress Carla Hayden was f…

1
Cardinal born in Chicago elected first Pope ever from U.S.; Pres. Trump & UK Prime Minister Starmer announce trade deal 53:11

22d ago53:11

53:11

U.S.-born Cardinal Robert Prevost is elected Pope at the Conclave at The Vatican, the first American to lead the Roman Catholic Church, taking name Pope Leo XIV; President Donald Trump and British PM Keir Starmer announce a trade deal; House passes bill to rename the Gulf of Mexico the “Gulf of America”, to write into law the President's executive …

1
Episode 372: Having Limited Capital and Scaling In Chicago Big Time with Kevin Schnell 54:20

23d ago54:20

54:20

Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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…

1
Federal Reserve Chair Powell cites tariff uncertainty in holding interest rates steady 52:59

23d ago52:59

52:59

The Federal Reserve holds interest rates steady. Chair Jerome Powell says there still is too much uncertainty in how Trump Administration policies, especially tariffs, will affect the economy, inflation and job growth; Treasury Secretary Scott Bessent testifies before a House committee about his meeting this weekend with Chinese officials on tariff…

1
Prime Minister Carney tells President Trump Canada 'won't be for sale, ever ' at White House meeting on trade & tariffs 56:43

24d ago56:43

56:43

Canadian Prime Minister Mark Carney meets U.S. President Donald Trump in the White House Oval Office, for what the president calls a "very friendly conversation"; President asked if there is anything the prime minister can say that would make him lift tariffs on Canada, replies "no"; Prime Minister asked about the president wanting to make Canada t…

1
Treasury Secretary Bessent encourages investors to buy into the President's economic plan of trade deals, tax cuts & deregulation 52:00

25d ago52:00

52:00

Treasury Secretary Scott Bessent urges global business leaders at a conference in California to have faith in President Donald Trump's three-part economic plan: tariffs to lead to better trade deals, tax cuts and deregulation; President Trump is asked about his weekend posts to impose a 100% tariffs on movies made in other countries and to reopen t…

1
Weekend Edition: President Trump's First 100 Days in Office, Political Polarization, and a new Harvard Youth Poll 38:03

28d ago38:03

38:03

In this weekend's episode, three segments from this past week's Washington Journal. First, President Trump marked his 100th day in office earlier this week – but ever wonder where that benchmark came from? We'll find out with presidential historian Lindsay Chervinsky. Then, Cook Political Report's David Wasserman discusses his analysis of the elect…

1
April jobs report, Pres. Trump sends Congress budget with spending cuts, Canadian PM preview DC meeting on tariffs 49:10

28d ago49:10

49:10

April jobs report; USA Today's Bart Jansen on President's FY'26 budget proposal with spending cuts (5); President Trump calls for the defunding of PBS and NPR; Reuters' David Ljunggren on Canadian Prime Minister's Mark Carney's preview of next week's meeting with President Trump to discuss trade and tariffs. (32) Learn more about your ad choices. V…

1
Nat'l Security Adviser Waltz to be nominated as U.S. Amb to UN; Sec of State Rubio to take second job as interim NSA 53:47

29d ago53:47

53:47

President Donald announces National Security Adviser Mike Waltz will leave that position and be nominated as U.S. Ambassador to the United Nations and Secretary of State Marco Rubio will take on the second job of National Security Adviser; General Motors estimates tariffs will cause a $5 billion loss in profits; President Trump speaks at a National…

1
Episode 371: How To Break into Chicago Real Estate Investing in Your 20s with Michael Kaplan 54:20

30d ago54:20

54:20

Michael Kaplan is a real estate broker and investor who has grinded to become a top broker at 24 years of age! Michael starts by explaining how he realized that college was not for him and pivoted to an entrepreneurial route in real estate! He explains the mindset required to start real estate investing and how he was able to acquire a 4-unit prope…

1
U.S. economy shrinks in first quarter; President Trump blames former President Biden; Sen. Schumer (D-NY) blames tariffs 54:44

1M ago54:44

54:44

Commerce Depart says the United States economy as measured by the Gross Domestic Product (GDP) shrank in the first quarter of the year by 0.3%, first time in three years. There was a surge in imports as companies tried to stock up before the President Donald Trump's high tariffs take effect. We get reaction from President Trump at a Cabinet meeting…

1
President Trump holds Michigan rally marking his first 100 days in office 54:05

1M ago54:05

54:05

President Donald Trump marks his First 100 days in office with a trip to Michigan; White House Press Secretary Karoline Leavitt and Treasury Sec Scott Bessent talk to reporters about the economy and trade; White House is very critical of Amazon after reports the company may list the cost of tariffs next to products sold online. Amazon says it was n…

1
Episode 370: How The Current 2025 Lending Market Differs From Previous Year 12:00

1M ago12:00

12:00

What's Different in Today's Lending Environment and How do Chicago Investors Capitalize? ============= 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: [email protected] Guest: Eric Workman…

1
White House touts border security as first of week-long First 100 Days successes 50:04

1M ago50:04

50:04

White House focuses on border security at start of week marking President Trump's first 100 days in office; Congress is back in session after a two-week recess, with committees writing their portions of the budget reconciliation bill; House votes on a bill requiring websites remove 'revenge porn'; DC Mayor Bowser announces deal to build a new stadi…

1
Weekend Edition: President Trump's Presidential Campaign, U.S. Fertility Rates, Reducing Political Polarization 35:46

1M ago35:46

35:46

In this weekend's episode, three segments from this past week's Washington Journal. First, author and filmmaker Chris Whipple discusses his book "Uncharted: How Trump Beat Biden, Harris, and the Odds in the Wildest Campaign in History." Then, University of Pennsylvania Economics professor Jesús Fernández-Villaverde -- discusses declining fertility …

1
Milwaukee judge arrested, charged with helping undocumented immigrant evade arrest by federal immigration authorities 46:22

1M ago46:22

46:22

The FBI arrests a judge in Milwaukee, accusing her of helping an Undocumented immigrant evade immigration authorities. She faces two felony counts. We will hear from Attorney General Pam Bondi and Milwaukee Mayor Cavalier Johnson. President Donald Trump and First Lady Melania Trump fly to Italy for the funeral of Pope Francis. Reports that China ha…

1
President Trump says he is 'putting a lot of pressure' on Russia after massive air strike on Kyiv 54:26

1M ago54:26

54:26

President Trump criticizes Russian President Putin for launching a deadly air attack on Ukraine, writing on Truth Social, "Vladimir, STOP!” and “I am not happy with the Russian strikes on Kyiv", but the President while meeting the visiting Norwegian Prime Minister at the White House, expresses confidence that a long-sought peace agreement can be re…

1
Episode 369: This Is How You Get Freedom of Time As a Chicago Investor with Erik Swanson 54:49

1M ago54:49

54:49

Erik Swanson, owner of Fernweh Property Group, explains how he’s developed a track record with investors that has allowed him to build a Tap Room business and an impressive real estate portfolio! Erik starts with very cool stories about his days in the music industry including working alongside some legendary bands! He dives into his first couple r…

1
Treasury Secretary says there is an opportunity for a 'big deal' between the U.S. and China to 'rebalance' on trade 56:43

1M ago56:43

56:43

Treasury Secretary Scott Bessent says there is an opportunity for a "big deal" between the U.S. and China to "rebalance" on trade and make China less dependent on manufacturing exports; Treasury Secretary also calling for the International Monetary Fund to focus on its core missions of economic stability and development and less on things like clim…

1
Supreme Court hears appeal from parents objecting on religious grounds to public school curriculum with LGBTQ themes 52:45

1M ago52:45

52:45

Supreme Court hears a case on whether parents can object on freedom of religion grounds to their children having to be part of a public school curriculum that includes with LGBTQ+ characters; Education Secretary Linda McMahon responds to Harvard University's lawsuit against the Trump Administration, which has withheld billions of dollars in grants;…

1
President Trump remembers Pope Francis as a 'good man' who 'loved the world', will attend funeral with First Lady Melania Trump 47:16

1M ago47:16

47:16

President Trump and others on death of Pope Francis; Defense Secretary Pete Hegseth calls the New York Times story claiming he shared sensitive military attack information in a second unsecure chat on the Signal App 'anonymous smears'; four House Democrats travel to El Salvador to call for the release and return to the U.S. deported accused gang me…

1
Weekend Edition: Alex Isenstadt, U.S. & China Trade War, Tax Day 27:30

1M ago27:30

27:30

First: a conversation with Axios Senior Political reporter Alex Isenstadt about his new book "Revenge: The Inside Story of Trump’s Return to Power." Then we speak with Lingling Wei, chief China correspondent for the Wall Street Journal -- about the brewing trade war between the U.S. and China and the impact of retaliatory tariffs. Plus: with TAX DA…

1
Sen. Van Hollen, back in U.S., gives update on meeting deported Kilmar Abrego Garcia in El Salvador prison 50:21

1M ago50:21

50:21

Sen. Chris Van Hollen (D-MD) returns to the U.S. after meeting Kilmar Abrego Garcia in a El Salvadorian prison, as President Trump again calls Garcia a violent gang member who deserved to be deported; Dr. Mehmet Oz is sworn in as CMS Administrator, pledging to deliver great care to the American people, but warning that involves facing some truths, …

1
Mass shooting at FSU; Pres. Trump meets Italian PM Meloni at White House on tariffs; Pres. Trump not saying if he will try to remove Fed Chair 55:13

1M ago55:13

55:13

Mass shooting at Florida State University in Tallahassee; President Donald Trump meets Italian PM Georgia Meloni at the White House to discuss trade and tariffs;President Trump is asked about his social media post that Federal Reserve chairman Jerome Powell's "termination cannot come fast enough", after the Fed Chair said that larger than expected …

1
Episode 368: Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Live Event) 40:42

1M ago40:42

40:42

Tom and Mark interview Joe Smazal of Interra Realty and Ann Reilly of Westward360 during NSBC’s Live Event! Conversations range from leasing trends to handling evictions and the state of the multifamily market in 2025. This show is full of valuable insights from two heavy hitters in the Chicago Multifamily Real Estate market! If you enjoy today’s e…

1
Fed Chair Powell says larger than expected tariffs will lead to higher inflation & slower growth; DOJ sues Maine over transgender athlete policy 51:52

1M ago51:52

51:52

Federal Reserve Chair Jerome Powell says President Donald Trump's tariff increases are larger "significantly larger than anticipated" and "same is likely to be true of the economic effects, which will include higher inflation and slower growth"; Gov. Gavin Newsom (D-CA) announces the first lawsuit against the Trump Administration over tariffs, chal…

1
Harvard Univ. has $2B in grants frozen after not complying with Trump Admin. demands, President says school should lose tax-exempt status 48:56

2M ago48:56

48:56

President Trump suggests Harvard Univ lose its tax-exempt status after the school refuses to comply with Administration's demands, as the Trump Administration freeze frozen over $2 billion in grants and contracts to Harvard; On this Tax Day, House and Senate members talk about the future of federal tax cuts and spending cuts, and IRS budget and sta…

1
Episode 367: How to Get Out In Front of Renewals With Jeff Weinberg 6:41

2M ago6:41

6:41

How do I incentivize and optimize renewals? ============= 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: [email protected] Guest: Jeff Weinberg, Drexel Properties Link: Jeff Weinberg Shar…

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