Better Bad Ideas with Sean O'Brien

By 7EQUISBusiness News News Commentary Politics

Better Bad Ideas with Sean O'Brien episodes

November 04 Will UPS Try to Replace Us If We Strike? | Better Bad Ideas | Ep. 93
Special thanks to our Launch Sponsor, Keches Law Group! Visit https://www.KechesLaw.com for your legal needs.
This episode is also brought to you by LaborFirst, the leader in healthcare
navigation and advocacy for plan sponsors, union members, and retirees. Visit https://laborfirst.com/ for more information.
New episodes of Better Bad Ideas drop every Wednesday! Subscribe and hit the bell to be notified when they go live! Also available where ever you download podcasts!
Chapters
08:48 | Harassment and Technology
12:22 | Mass Write-Ups of UPS Warehouses in 2026
14:24 | Teamsters Organizing Delta Flight Attendants
17:28 | Changing 9.5 Penalty Pay
21:46 | UPS Utilizing Alternative Subsidiaries During A Strike to Weaken Leverage
23:31 | Establishing Delivery Cut-Off-Time
26:38 | Teamsters Fighting Amazon’s Contractor Model to Protect Drivers
28:53 | The Voice of Teamsters
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33 min
October 28 UPS Workers Deserve Family Time | Better Bad Ideas | Ep. 92
Special thanks to our Launch Sponsor, Keches Law Group! Visit https://www.KechesLaw.com for your legal needs.
This episode is also brought to you by LaborFirst, the leader in healthcare
navigation and advocacy for plan sponsors, union members, and retirees. Visit https://laborfirst.com/ for more information.
New episodes of Better Bad Ideas drop every Wednesday! Subscribe and hit the bell to be notified when they go live! Also available where ever you download podcasts!
Chapters
00:00:00 | Threat from Technology on White-Collar Jobs00:10:15 | What’s the plan in 2028 to make sure 40-hour Teamster jobs keep up with inflation and remain middle-class jobs?00:12:46 | Should the Next UPS Contract Prioritize Quality of Life, With More Time Off and Better Work-Life Balance?00:15:38 | Why Does So Much Teamster Attention Go to UPS and Amazon When Construction, Pipeline, and Other Trades Are Facing Major Issues Too?00:19:11 | What is the Teamsters’ Plan to Organize the Nonunion Fuel-Hauling Industry Nationwide Before More Union Jobs Are Lost?00:23:32 | Can We Increase Steward Coverage Inside Every Building So Members Feel Supported Enforcing the Contract?00:26:39 | What Sets Your Bipartisan Approach to Labor Apart From Other Union Leaders?00:28:46 | Why Does the Union Sometimes Feel Divided Between Drivers and Warehouse Workers Instead of United as One Membership?00:30:31 | How Can Worldport Mechanics Get Their Own Contract Language to Address Forced Overtime and Scheduling Issues?00:32:45 | Could Worldport Members Who Waited Decades for Full-Time Work Fight for Peer 80/85 Retirement in the Next Contract?
Better Bad Ideas
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36 min
October 21 When UPS Valued a Package More Than a Life | Better Bad Ideas | Ep. 91
Special thanks to our Launch Sponsor, Keches Law Group! Visit https://www.KechesLaw.com for your legal needs.

This episode is also brought to you by LaborFirst, the leader in healthcare
navigation and advocacy for plan sponsors, union members, and retirees. Visit https://laborfirst.com/ for more information.

New episodes of Better Bad Ideas drop every Wednesday! Subscribe and hit the bell to be notified when they go live! Also available where ever you download podcasts!

Chapters
00:00:00 | Surveillance and Technology
00:16:18 | Only Answering Easy Questions
00:19:53 | Why Haven’t Top Teamsters Leaders Done More to Support the Henry Ford Strike?
00:22:09 | If UPS Teamsters Cross the Picket Line in 2028, What Happens After the Contract is Settled?
00:24:20 | What are the Priorities for the 2028 TForce Freight Contract?
00:27:46 | Increasing Teamsters Pensions to Keep Up with Rising Living Costs
00:30:31 | Adding Contract Language Requiring Operations to Stop After a Workplace Death or Serious Fatal Incident
00:33:32 | Can We Cap Forced Overtime for Feeder Drivers to Improve Work-Life Balance?
00:35:04 | Can Sean Visit Specific Centers to See First-Hand What is Happening?
00:35:28 | What Will Teamsters Do in 2028 to Strengthen Pensions and Retirement Benefits?
00:38:21 | Should the Union Protect Drivers Who Underperform Based on Company Tracking?
00:39:26 | Should the 2028 Contract Prioritize Grievance Enforcement and Quality of Life Over Another Historic Wage Increase?
00:42:28 | Why Does the Central Region Have Lower Pension Benefits Than Other Regions?
00:43:41 | Where Can Members See How the Union is Spending Dues?

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48 min
October 14 Why UPS Not Paying For Employee's Socks Is A Symptom Of A Bigger Problem | Better Bad Ideas | Ep. 90
Special thanks to our Launch Sponsor, Keches Law Group! Visit https://www.KechesLaw.com for your legal needs.

This episode is also brought to you by LaborFirst, the leader in healthcare
navigation and advocacy for plan sponsors, union members, and retirees. Visit https://laborfirst.com/ for more information.

New episodes of Better Bad Ideas drop every Wednesday! Subscribe and hit the bell to be notified when they go live! Also available where ever you download podcasts!

Chapters
00:45 | Corporate AI and Automation
09:24 | Do pipeline and construction Teamsters get the same fight and attention as UPS and Amazon members?
13:08 | Full-time UPS Members Having the Same Transfer Rights as Part-Timers
16:19 | Who is Sean O'Brien looking to have as a guest on the show?
17:47 | Recognizing an earlier generation of Teamsters and labor fighters
22:13 | Organizing Private Security Companies and Switching Unions
23:00 | Workers Facing Retaliation and What They Should Do
26:51 | On-Site Gyms at UPS Facilities
29:27 | Should UPS Provide Socks for Workers?
31:35 | Sean O’Brien as the President of Teamster
33:33 | Adjusting UPS Mechanic Pay
37:11 | Progressing UPS Vacation Time for Workers
38:44 | Protecting UPS Drivers From Dangerous Staffing Practices During Extreme Summer Heat
41:56 | Holding UPS Accountable During Grievance Processes

Better Bad Ideas
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• https://open.spotify.com/show/5Br4YZ6h20M6VZGBtIsaBs?si=eaa75a585c7f4ccd
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47 min
October 07 UPS Made $100B and Part Timers Still Can't Afford Housing | Better Bad Ideas | Ep. 89
Special thanks to our Launch Sponsor, Keches Law Group! Visit https://www.KechesLaw.com for your legal needs.

This episode is also brought to you by LaborFirst, the leader in healthcare
navigation and advocacy for plan sponsors, union members, and retirees. Visit https://laborfirst.com/ for more information.

New episodes of Better Bad Ideas drop every Wednesday! Subscribe and hit the bell to be notified when they go live! Also available where ever you download podcasts!

Chapters
00:00:00 | Intro
00:01:19 | Unions’ Ability to Strike
00:13:16 | How Should Local Unions Prepare Workers for the First Contract Fight?
00:16:44 | Building Solidarity Between Part-Time and Full-Time UPS Members
00:25:14 | Should Pensions, Healthcare, and More Optional Days be Prioritized in the Next UPS Contract?
00:25:53 | Preventing Management Harassment in the Next UPS Contract
00:28:41 | Drawing the Line Between Normal Supervision and Management Harassment
00:30:51 | Making Strong Contract Demands Without Losing Public Support
00:32:30 | Starting the Process of Unionizing at Amazon
00:34:05 |The Plan to Fight for a Better Pension Benefit at TForce Freight
00:34:49 | Will the Union Address UPS Air Progression to Prevent a Pay Freeze?
00:36:36 | Addressing Lowering Pension Payouts and Raising Healthcare Costs After Retirement
00:38:42 | Teamsters Plan to Help CSX Workers Facing Cuts and Workers Left with the Extra Workload
00:40:30 | Will UPS Address Forced Overtime, Work-Life Balance, and Understaffing Without the Threat of Discipline?
00:43:37 | Teamsters Enforcing the New 7,500 UPS Jobs and How Many Have Been Filled Nationwide?
00:44:37 | Can the IBT Assign Someone to Track and Enforce UPS 22.3 Job Creation Nationwide?

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49 min
September 30 UPS Makes BILLIONS & Teamsters Demand Their Fair Share | Better Bad Ideas | Ep. 88
Special thanks to our Launch Sponsor, Keches Law Group! Visit https://www.KechesLaw.com for your legal needs.

This episode is also brought to you by LaborFirst, the leader in healthcare
navigation and advocacy for plan sponsors, union members, and retirees. Visit https://laborfirst.com/ for more information.

New episodes of Better Bad Ideas drop every Wednesday! Subscribe and hit the bell to be notified when they go live! Also available where ever you download podcasts!

Chapters
00:00:00 | Intro
00:00:39 | Teamsters Growth Strategy
00:04:23 | Faster Labor Contracts Act
00:08:59 | Will Federal Minimum Wage Differential Clauses Be Introduced Into Current and Future Contract Negotiations?
00:10:18 | How Do You Convince Someone Who Likes the Idea of a Union, But is Afraid of Retaliation?
00:12:44 | Air-Conditioned Trucks
00:16:33 | Consolidation of Pension Funds Into the WCTPTF
00:19:08 | Why Isn’t the Military in Any Unions? Are There Amish in the Union?
00:20:57 | Chances of 9.5 Violations Being Automatically Added to Weekly Paychecks in the Next Contract
00:24:23 | Tips for Keeping a Podcast for Local Levels and Younger Generations Going
00:27:44 | Big Raise Rather Than Time Off
00:29:37 | Quit Threatening to Strike and Work for Protection From Layoffs and Automation
00:31:49 | Why Do Mechanics Get Paid the Same as Drivers?
00:34:14 | Will Rank-and-File Members be Allowed to Come to the Bargaining Table for the 2028 UPS Contract?
00:35:41 | Conversations About What the UPS Will Save Over the Four-Year Progression Period

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38 min
September 23 Inside UPS: Split Shifts, Harassment, & the Fight for Better Conditions | Better Bad Ideas | Ep. 87
Special thanks to our Launch Sponsor, Keches Law Group! Visit https://www.KechesLaw.com for your legal needs.

This episode is also brought to you by LaborFirst, the leader in healthcare
navigation and advocacy for plan sponsors, union members, and retirees. Visit https://laborfirst.com/ for more information.

New episodes of Better Bad Ideas drop every Wednesday! Subscribe and hit the bell to be notified when they go live! Also available where ever you download podcasts!

Chapters
00:35 | Political Approach
06:26 | Faster Labor Contracts Act
10:26 | Everyone included, how many Teamsters are there?
12:07 | How do unions win over workers in right-to-work states where anti-union messaging is everywhere?
12:54 | Closing the Benefits Gap Across Supplements
16:04 | Protecting Full-Timers From Forced Split Shifts
16:49 | What industries are ready for a major union push?
19:18 | Removing Article 40?
20:10 | What’s the biggest mistake workers make when they’re trying to organize for the first time?
21:02 | Creating More UPS Jobs in a Competitive Shipping Market
22:12 | Preventing Workplace Harassment and Strengthening Member Protections
25:19 | Protecting UPS Jobs From Subcontracting, AI, and Automation
25:15 | Addressing Foreign-Subsidized Competition in the U.S. Parcel Market
27:22 | Modernizing Union Technology and the Grievance Process
28:43 | Is Sean O’Brien really this jacked?

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31 min
September 16 UPS CEO Called Buyouts and Layoffs "Bumps In The Road" | Better Bad Ideas | Ep. 86
Special thanks to our Launch Sponsor, Keches Law Group! Visit https://www.KechesLaw.com for your legal needs.

This episode is also brought to you by LaborFirst, the leader in healthcare
navigation and advocacy for plan sponsors, union members, and retirees. Visit https://laborfirst.com/ for more information.

New episodes of Better Bad Ideas drop every Wednesday! Subscribe and hit the bell to be notified when they go live! Also available where ever you download podcasts!

Chapters
00:00 | Intro
00:11:07 | Tips to Remain Fit and Healthy
00:12:56 | Will Union Leaders Address 22.3s Being Kept on Indefinite Split Shifts?
00:14:46 | Can Office Workers Form a Union with Teamsters?
00:15:45 | What Will Full-Time Drivers Get in the Next Contract?
00:17:01 | Striking Over Deadlocked Grievances
00:19:45 | Is the Union Prepared to Prioritize Combating Automation Over an Increase in Wages?
00:22:12 | Different Part-Time Pensions Throughout the United States
00:24:31 | How Do We Get Members to Show Up Before There’s a Crisis
00:27:15 | Securing a Day Off for a Funeral Without Using a Call-In
00:28:36 | When Do UPS Teamsters Get Surepost and Roadie Work That Was Diverted to Outside Companies?
00:30:08 | How Do We Rebuild Union Culture For Members Who Feel More Like Coworkers Than Brothers and Sisters?
00:31:12 | Looking Into Walked Back Penalty Pay

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34 min
September 09 Strike Fund Ready: Preparing UPS Members for the Fight Ahead | Better Bad Ideas | Ep. 85
Special thanks to our Launch Sponsor, Keches Law Group! Visit https://www.KechesLaw.com for your legal needs.

This episode is also brought to you by LaborFirst, the leader in healthcare
navigation and advocacy for plan sponsors, union members, and retirees. Visit https://laborfirst.com/ for more information.

New episodes of Better Bad Ideas drop every Wednesday! Subscribe and hit the bell to be notified when they go live! Also available where ever you download podcasts!

Chapters
01:00 | Roads: Helping families who suffer from addiction and mental illness
10:21 | Keep striking in the public dialogue
12:16 | Teamsters serving members at every career stage
13:49 | Driverless Trucks
18:55 | UPS Strike Fund
21:31 | Teamster members and Amazon workers
25:15 | Teamsters prioritizing sanitation workers nation wide
29:32 | Non-union purchasedtransportation in 2028

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34 min
September 02 "It's Disrespectful and Disgusting" – Sean O'Brien on UPS Management | Better Bad Ideas | Ep. 84
Special thanks to our Launch Sponsor, Keches Law Group! Visit https://www.KechesLaw.com for your legal needs.

This episode is also brought to you by LaborFirst, the leader in healthcare
navigation and advocacy for plan sponsors, union members, and retirees. Visit https://laborfirst.com/ for more information.

New episodes of Better Bad Ideas drop every Wednesday! Subscribe and hit the bell to be notified when they go live! Also available where ever you download podcasts!

Better Bad Ideas
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26 min