7 of the Worst Run Companies in America 8-16-25 - Becker Private Equity & Business Podcast

Summary3 min read

Becker Private Equity & Business Podcast Host: Scott Becker
Episode: 7 of the Worst Run Companies in America
Date: August 16, 2025

Episode Overview

In this episode, Scott Becker discusses the topic of "the worst run companies in America," drawing on a list generated by artificial intelligence tools (Grok and ChatGPT). Scott makes it clear that these evaluations are not his personal opinions but are compiled from AI-based research. The episode reviews seven companies reportedly struggling with leadership, financial, and operational challenges, according to AI sources.

Key Discussion Points & Insights

AI-Generated Rankings: A Caveat

Host’s Disclaimer: Scott emphasizes from the outset that the list is directly from an AI search and not his subjective view.
- Quote: "These are not my thoughts. These come from artificial intelligence, so don't shoot the messenger." (00:17)
AI’s basis appears to include recent news, stock performance, and leadership perceptions.

The 7 “Worst-Run” Companies According to AI

1. Boeing

Top of the List: AI cites safety and quality issues, continued financial performance problems, and high-profile leadership struggles.
Quote: “Boeing topped the list for safety and quality issues, financial performance issues, leadership issues and a lot more.” (00:41)

2. Tesla

Fluctuating Performance: Although recovery is noted in the current year, Tesla frequently appeared in lists of poorly run companies due to past volatility.
Quote: “Tesla ranked up there in a lot of these things, although it’s recovering significantly this year.” (00:55)

3. Intel

Ongoing Struggles: Intel has faced difficulty for several years, though it's currently attempting to turn things around.
Quote: “Intel, which has been on the ropes for a few years, also featured prominently in the worst run companies, though again trying to improve.” (00:59)

4. Centene

Recent Decline: Despite prior rapid growth as a major Medicaid managed care provider, Centene has had a notably poor track record over the past year.
Quote: “Centene’s having a horrible, horrible track record the last 52 weeks, but until then it had grown like crazy as the leading Medicaid managed care company in the country.” (01:11)

5. Deckers Outdoors

Brand Struggles: Owner of popular footwear and apparel brands like HOKA, Deckers is struggling notably despite strong brand recognition.
Quote: “Deckers is the owner of HOKA and a lot of other big brands notwithstanding how much... we’re those brands. They are struggling tremendously, so they come up in that.” (01:28)

6. Walgreens

Consistent Underperformance: Walgreens has experienced prolonged struggle, though the situation may be improving as private equity takes a bigger role.
Quote: “Walgreens has been struggling tremendously. It’s taken a little bit better now as private equity starts to buy it...” (01:37)

7. CVS Health (CVS, Aetna)

Major Setbacks: CVS struggles both on the retail pharmacy front and in its health insurance (Aetna) and pharmacy benefit management (PBM) businesses.
Quote: “CVS again, another company that has been having a horrible time as of late. It’s got the big, big pharmacy chain, retail side, it’s got the big payer in Aetna. Then it’s got the pbm, but again comes down and it is listed as one of the worst run companies.” (01:45)

Memorable Moments & Tone

Scott’s humorous defensiveness is a recurring theme as he distances himself from the AI list:
- Quote: “I don’t mean to be such a wuss by just constantly clarifying not my list, but that’s the deal.” (02:01)

Timestamps for Important Segments

[00:00] – Host’s introduction and AI disclaimer
[00:41] – Boeing tops the AI-generated list
[00:55] – Tesla's fluctuating performance
[00:59] – Intel’s efforts to recover
[01:11] – Centene’s downturn after expansion
[01:28] – Deckers Outdoors’ ongoing struggles
[01:37] – Walgreens: private equity involvement and ongoing issues
[01:45] – CVS/Aetna/PBM: comprehensive business struggles
[02:01] – Host’s closing comments and disclaimer

Summary

Scott Becker navigates the delicate subject of poorly managed companies in America, relying on AI to avoid personal bias. The episode offers insights into why these seven companies are currently perceived as struggling, with specific mention of safety, leadership, financial, and brand issues. Throughout, Becker injects humor and caution, reminding listeners that he's simply reporting AI findings, making the episode both informative and lightly self-deprecating in tone.

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Transcript1 lines

[00:00]
A
This is Scott Becker with the Becker Private Equity. In the Becker Business podcast, today's discussion is seven of the worst run companies in America. So here's the deal and here's the caveat. This list comes out of me doing this search. It was either in Grok or ChatGPT. What are 7 or what are several of the worst run companies in America? These are not my thoughts. These come from artificial intelligence, so don't shoot the messenger. But here's the story and what we got out of AI as seven of the worst run companies in America. And again, this is not my opinion, but a lot of this has to do. What's going on, their stock, the thoughts about their leadership and a lot more. I'm going to give you the 7. In one of these AI searches, Boeing topped the list for safety and quality issues, financial performance issues, leadership issues and a lot more. Six of the others that came up as some of the worst run companies in America. And again, bear with me, Tesla ranked up there in a lot of these things, although it's recovering significantly this year. Intel, which has been on the ropes for a few years, also featured prominently in the worst run companies, though again trying to improve. Centene comes up prominently in the list of worst run companies. Again, Centene's having a horrible, horrible track record the last 52 weeks, but until then it had grown like crazy as the leading Medicaid managed care company in the country. Next is Deckers Outdoors. Deckers is the owner of HOKA and a lot of other big brands notwithstanding how much a lot of us, we're those brands. They are struggling tremendously, so they come up in that. Next is Walgreens again. Walgreens has been struggling tremendously. It's taken a little bit better now as private equity starts to buy it, but Walgreens has been struggling tremendously. Next is cvs, Aetna, CVS again, another company that is, that has been having a horrible time as of late. It's got the big, big pharmacy chain retail side, it's got the big payer in Aetna. Then it's got the pbm, but again comes down and it is listed as one of the worst run companies. So I thought that was interesting to watch. Those are seven of the worst run companies in America. Again, not my thoughts. Those are the thoughts that come out of the AI tool that I plugged that request into. Thank you for listening to the Becker Business podcast, the Becker Private equity podcast. And I don't mean to be such a wuss by just constantly clarifying not my list, but that's the deal. We hope you find it interesting. Thank you for listening.