Advertise on podcast: Better Bad Ideas with Sean O'Brien
Rating
4.5from
This podcast has
88 episodes
Language
EnglishPublisher
7EQUISExplicit
No
Date created
2024/12/20
Latest episode
2026/09/30
Average duration
46 min.
Release period
7 days
Description
Sean M. O'Brien sits down with the realest personalities on earth. First episode drops January 15th, 2025 and every Wednesday after that. Follow @betterbadideas
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Check latest episodes from Better Bad Ideas with Sean O'Brien podcast
UPS Makes BILLIONS & Teamsters Demand Their Fair Share | Better Bad Ideas | Ep. 88
2026/09/30
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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Inside UPS: Split Shifts, Harassment, & the Fight for Better Conditions | Better Bad Ideas | Ep. 87
2026/09/23
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?
Better Bad Ideas
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UPS CEO Called Buyouts and Layoffs "Bumps In The Road" | Better Bad Ideas | Ep. 86
2026/09/16
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
Better Bad Ideas
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Strike Fund Ready: Preparing UPS Members for the Fight Ahead | Better Bad Ideas | Ep. 85
2026/09/09
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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"It's Disrespectful and Disgusting" – Sean O'Brien on UPS Management | Better Bad Ideas | Ep. 84
2026/09/02
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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The Last-Mile Problem: How Amazon and FedEx Use Contractors to Dodge Responsibility
2026/08/26
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
Better Bad Ideas
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UPS Leadership is Destroying the Package Delivery Business | Better Bad Ideas | Ep. 82
2026/08/19
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
01:17 | New Term
01:58 | UPS
04:13 | Carol Tomé
08:16 | Corewell Nurses
09:26 | Viewer Question 1
11:43 | Viewer Question 2
13:20 | Viewer Question 3
15:14 | Viewer Question 4
18:57 | Viewer Question 5
23:02 | Viewer Question 6
23:59 | Viewer Question 7
27:32 | Viewer Question 8
29:51 | Viewer Question 9
31:59 | Viewer Question 10
32:55 | Viewer Question 11
33:28 | Viewer Question 12
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UPS vs. Teamsters: Why Contract Enforcement Matters | Better Bad Ideas | Ep. 81
2026/08/12
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
Better Bad Ideas
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The Truth About UPS’s “Partnership” with Teamsters
2026/08/05
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 | UPS Stock Trending Down - Carol Tomé
05:06 | Roadie Is A Scheme
07:45 | Direction UPS Is Going In
09:10 | 2028 Plan - Fight For The Right To Strike
14:18 | Question: Caucuses?
18:36 | Question: 40 Hours, 4 Days?
22:11 | Question: Which Politicians Deserve Support?
23:36 | Question: Pension And Life Insurance?
26:01 | Question: AI In The Workplace?
28:13 | Question: Super Seniority?
29:23 | Question: UPS Contract Negotiations?
33:41 | Question: Part Time Pension?
36:19 | Question: Build More Power Before The Negotiation?
Better Bad Ideas
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The UPS Contract is Coming: Are We Ready? | Better Bad Ideas w/Sean O'Brien | Ep. 79
2026/07/29
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
1:20 Striking UPS
6:20 Everything is Politicized
10:30 Collaboration Will Help Working Middle Class
19:30 Question 1
20:53 Question 2
23:03 Question 3
24:49 Question 4
27:29 Question 5
29:45 Question 6
32:48 Question 7
36:20 Question 8
38:41 Question 9
39:25 Question 10
40:52 Question 11
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Why This CEO Embraced the Teamsters Union | Better Bad Ideas w/Sean O'Brien | Ep. 78
2026/07/22
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
00:40 | Benefits Of Partnering With Union
02:25 | What Is Armstrong Ambulance?
04:40 | Getting Into Being An Emt
07:15 | PTSD In The Field
17:00 | Training To Deal With Horrific Scenes
26:15 | Navigating The Politics Of Your Organization
33:45 | Sean’s Healthcare Company Vs Competitors
36:20 | Costs Of Running A Bus
41:15 | Being Politically Connected In This Business
43:54 | Giving Your Heart And Soul Into The Community
47:21 | Specific Contract Language
52:36 | EMT Response Time
55:19 | Is The Mayor Anti-Union?
1:05:34 | Next Moves As A CEO
1:10:00 | Day To Day Responsibilities
1:14:44 | If You Could Have Lunch Or Dinner With Anyone, Who Would It Be?
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UPS vs. The Teamsters: Corporate Trickery Meets Union Power | Better Bad Ideas | Ep. 77
2026/07/15
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 | Government Oversight is OUT of Teamsters
09:49 | What Important Lessons Did Sean Learn?
11:09 | What Are the Plans for UPS Part-Timers’ Raises?
14:19 | How Do We Sustain Healthcare Costs?
16:39 | Follow The International Union!
22:52 | How Have Women Strengthened Teamsters?
26:24 | Teamsters’ Plans for the Next 5 Years
31:53 | How Politicians Get Teamsters’ Support
36:34 | Has the Labor Movement Relied Too Much on Politicians?
37:59 | Negotiating Better Protections for Union Workers from Third Parties
39:30 | Teaching Rank-and-File Members to Lead
42:05 | Outro
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Post Teamsters Election Win Q&A! | Better Bad Ideas w/Sean O'Brien | Ep. 76
2026/07/08
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 | 31st Teamsters Convention
06:05 | The Bipartisan Effort & Faster Labor Contracts Act
10:19 | Corporate America vs. Union Legislation
15:53 | Viewer Questions
18:06 | Who Has a Better Job Than Chris Hansen?
25:09 | How Should Members Prepare for Next Negotiation?
31:45 | What If Bipartisan Efforts Fail?
34:49 | How Will Future Generations Maintain the Opportunities Offered by Unions?
39:07 | FIFA Fans Drinking Boston Dry
39:57 | Changes to Give Power Back to the Members
43:30 | Outro
Better Bad Ideas
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Massachusetts State Senator Nick Collins | Better Bad Ideas w/Sean O'Brien | Ep. 75
2026/07/01
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
Better Bad Ideas
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Boston's First Black Police Commissioner - William Gross | Better Bad Ideas w/Sean O'Brien | Ep. 74
2026/06/24
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
03:10 Harry Wilson
10:26 Breaking social stereotypes
15:30 Charles Stuart
23:24 You want change, be the change
26:20 Whitey Bulger story
34:30 Leveraging Authority
37:27 Detective SGT. to first black Superintendent in Chief
47:29 Success has 1 million fathers, failure is an orphan
1:03:17 Stepping up, no Ego
1:08:10 Learn from each other
1:17:45 Toughest part about being Commissioner
1:20:45 Empathy, Sympathy, Care, Respect
1:27:00 What do you do in retirement?
1:28:45 Lunch with anybody still alive?
Better Bad Ideas
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Podcast reviews
Read Better Bad Ideas with Sean O'Brien podcast reviews
Browfixer 2026/07/29
UPS mechanics
Sean thank you for all you do but could we get more language for mechanics.
KevinLemieux 2026/02/04
Benson
Benson what a condescending blow hard just what we need another blow hard democratic lawyer fair election what a joke good luck Michigan let me know h...
mojack 00 2025/09/11
Let the guests talk
Today driving north on 23 through Chillicothe, OH, I decided to listen to your interview with Amy Acton. Could only get a half hour into it because Se...
E-frommedford 2025/05/06
A man with great American views
I am not a team so I am a simple local businessman. I’ve known Sean my whole life.
Since we were kids him and his brothers and his father always stood...
Ronny Hale 2025/04/25
Sean O’ Brien
Sean is what the IBT has needed. I look forward to Amazon joining the Teamsters.
IDontKnowWhatIveBeenTold 2025/04/11
Great Show, Great Host
Sean is stand up guy, no question about it. I really like the show content and format, genuine. After nearly 40 years of blue collar work I am more pr...
Anarchist Cat 2025/04/08
Garbage
20 year teamster here. Don’t support this fascist. First episode is with a union buster.
Boxmonkey1 2025/03/11
Scab
This guy has no business speaking about politics or social topics. As a pro right-to-work union president he’s an embarrassment to all the workers now...
SFProducer 2025/02/14
Wish I could give this show ZERO stars
O’Brien’s a sell-out and a fool. Josh Hawley?! The guy who voted against Teamster pensions? Trump and Musk are dismantling the labor movement while th...
East River Nvest 2025/01/23
Great Idea 😉
Sean M. O’Brien’s new podcast, Better Bad Ideas, is a must-listen for anyone who cares about real, unfiltered conversations. He tackles big issues wit...
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