Best Worst Possible Productions Podcasts (2025)

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4 Surprising Productivity Hacks for Women 33:18

Play Pause

11h ago33:18

33:18

Every female in our lives right now seems to be suffering from the same complaint—there’s too much to do and too little time and we’re struggling to buckle down. Most of us ladies right now are aiming for better productivity, focus, and motivation. If this sounds familiar, this episode is for you. Brierley and I are excited to share four new hacks—…

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E39: Why Learning How to Learn Is Your Only Competitive Advantage Left (And My 5-Step Framework) 34:19

2d ago34:19

34:19

Why Learning How to Learn Is Your Only Competitive Advantage Left I sat in that accelerator orientation listening to them brag about mentors who'd been teaching entrepreneurship for 15+ years. Everyone clapped. I was terrified. These were people with employee mindsets teaching the same frameworks from 2010. In an AI-first world where anyone can bui…

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Building a Strong Data Foundation in an AI World 29:22

1d ago29:22

29:22

AI is everywhere, but it can't succeed without the judgment, creativity, and collaboration of real data science. In this episode, Jess Carter sits down with Alexa Myers, senior data science manager at Resultant, for a conversation about building successful data science teams. They discuss how isolation can hinder even the most skilled data scientis…

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EP. 335 REJECT NOSTALGIA 1:35:11

1d ago1:35:11

1:35:11

SUPPORT THE LADS AND GET AD FREE + BONUS EPISODES AT WWW.PATREON.COM/WORSTPOSSIBLETIMELINE Learn more about your ad choices. Visit megaphone.fm/adchoicesBy Worst Possible Productions & Sound Talent Media

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Rant Therapy: Worst Holiday Ever 8:39

2d ago8:39

8:39

The best (and cheapest) therapy for those small things that get under your skin is sometimes a good venting session so you can get it off your chest and move on with your life! And if you’re not privy to the first-hand vent-a-thon, then being a fly on the wall listening is hopefully equally therapeutic and also maybe entertaining. Welcome to Rant T…

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E38: My Worst Hires Almost Destroyed Us (Here's What I Learned About Building Teams in 2025) 34:28

3d ago34:28

34:28

My Worst Hires Almost Destroyed Us (Here's What I Learned) After scaling from 15 people down to 4, then back to 5, I've never shared my actual hiring criteria. Today I'm telling you about the engineer who took unlimited PTO during his wedding while our engineering delivery collapsed, the sales guy who learned to sell to us, and the contractor who t…

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E37: Why I Changed My Mind About Multiple Products (And You Should Too) 25:30

7d ago25:30

25:30

Why I Changed My Mind About Multiple Products (And You Should Too) For years, I preached single product focus. "Build one thing really well," I'd tell founders. Today, I'm running SimpleDirect with four product lines and ANC with three consulting verticals. What changed? Everything. This episode breaks down why the season has shifted from single pr…

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The Rejection Sensitive Dysphoria Episode 21:46

7d ago21:46

21:46

The Rejection Sensitive Dysphoria Episode Nobody likes rejection. But for some people teasing, being left out of a social event, even receiving constructive criticism can lead to extremely negative feelings. Put another way, the punishment doesn’t fit the crime—the emotional reaction doesn’t match the perceived slight made. This is called Rejection…

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E36: The AI Exercise That Almost Destroyed Me (In the Best Way Possible) 34:54

9d ago34:54

34:54

The AI Exercise That Almost Destroyed Me (In the Best Way Possible) Last night, I asked Claude to tell me something I don't know about myself - good or bad, brutally honest. What came back almost destroyed me in the best way possible. As founders, we have blind spots we can't see. We're running the show, making decisions, often surrounded by people…

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Rant Therapy - Making A Dinner That No One Likes 6:15

9d ago6:15

6:15

The best (and cheapest) therapy for those small things that get under your skin is sometimes a good venting session so you can get it off your chest and move on with your life! And if you’re not privy to the first-hand vent-a-thon, then being a fly on the wall listening is hopefully equally therapeutic and also maybe entertaining. Welcome to Rant T…

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E35: When to Stop Consulting and Build a Product: The $200M Basecamp Question 22:41

10d ago22:41

22:41

When to Stop Consulting and Build a Product - The $200M Basecamp Question The question I get most since publishing "The Anti-Unicorn": "George, I've built a successful consulting business. When do I stop consulting and actually build a product?" After three years building consulting revenue while almost killing SimpleDirect twice, I have some hard-…

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EP. 334 RAISON CANES D'ETRE 1:18:18

10d ago1:18:18

1:18:18

SUPPORT THE LADS AND GET AD FREE + BONUS EPISODES AT WWW.PATREON.COM/WORSTPOSSIBLETIMELINE Learn more about your ad choices. Visit megaphone.fm/adchoicesBy Worst Possible Productions & Sound Talent Media

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E34: Three Expensive Lessons About Money That Changed How I Think About Wealth 33:47

14d ago33:47

33:47

Three Expensive Lessons About Money That Changed How I Think About Wealth I just finished Morgan Housel's "The Art of Spending Money" and it completely changed how I think about wealth. Five years ago when I was broke, his first book "The Psychology of Money" transformed how I thought about earning. Now with two profitable companies, I realized I h…

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Using Cooking as Therapy to Improve Mental Health 55:30

14d ago55:30

55:30

Using Cooking as Therapy to Improve Mental Health The concept of experiential therapy isn’t new: there’s art therapy, equine therapy, play therapy. But one form you might not be familiar with is cooking therapy. Research tells us that cooking and baking are favorite hobbies of Americans—above reading, time spent with pets, video games, or outdoor a…

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E33: Why Everyone's Chasing the Wrong Thing (And It's Making Them Replaceable) 31:10

16d ago31:10

31:10

Why Everyone's Chasing the Wrong Thing (And It's Making Them Replaceable) I walked away from a $3-5 million partnership deal two months ago. Not because the numbers were bad, but because something in my gut said "this feels like work." Most founders would call me crazy, but here's what I've learned: the moment you start optimizing for external vali…

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REPLAY: Driving ROI through Collaborative Organizational Change Management 30:34

15d ago30:34

30:34

Organizations are racing toward digital and AI transformation, but the same problem keeps showing up: people aren't ready. In this replay episode, Jess Carter revisits her conversation with Allison Grayson, Senior Director of Organizational Change Management at Resultant. They explore the fundamentals that ensure change is well implemented in an or…

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Rant Therapy: Left-Lane Drivers 5:30

16d ago5:30

5:30

The best (and cheapest) therapy for those small things that get under your skin is sometimes a good venting session so you can get it off your chest and move on with your life! And if you’re not privy to the first-hand vent-a-thon, then being a fly on the wall listening is hopefully equally therapeutic and also maybe entertaining. Welcome to Rant T…

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E32: Why I Wrote a 350-Page Free Ebook Against Everything Silicon Valley Teaches 40:49

17d ago40:49

40:49

Why I wrote a 350-page free ebook that goes against everything Silicon Valley teaches about startups. The consulting-first model that works for the 99.95% of founders who will never raise VC - and why the traditional advice is poisoning young entrepreneurs. The brutal reality nobody talks about: Only 0.05% of startups ever raise VC funding (5 out o…

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EP. 333 VEGETATION DIETY 1:28:28

20d ago1:28:28

1:28:28

AD FREE AND BONUS EPISODES AT WWW.PATREON.COM/WORSTPOSSIBLETIMELINE Learn more about your ad choices. Visit megaphone.fm/adchoicesBy Worst Possible Productions & Sound Talent Media

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E31: 3 Thoughts That Changed How I Run My Companies 24:29

21d ago24:29

24:29

Three interconnected insights that fundamentally changed how I run SimpleDirect and ANC. Why finding balance beats going to extremes, measuring the right things determines your destination, and building systems creates compound leverage. Thought #1: Why LinkedIn makes me cringe (and why I was wrong too): LinkedIn is 50% performance theater - fake v…

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Eldest Daughter Syndrome 31:48

21d ago31:48

31:48

If you’ve listened to Taylor Swift’s newest album, you may have heard her song Eldest Daughter. If not, the gist is this: she sings about the pressure to seem strong, cool, and not let people down. As eldest daughters, this resonated with Brierley and me. So we dove in: what is eldest daughter syndrome? How does it develop during childhood and how …

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E30: How to Know When to Pivot vs. Shut Down Your Startup (The 8am Text That Saved My Company) 31:48

23d ago31:48

31:48

The 8AM Text That Saved My Company: When to Pivot vs. Sunset" Episode Summary George shares the raw, unfiltered story of almost shutting down SimpleDirect Financing last week - and how an 8am customer text changed everything. This is a deep dive into the emotional rollercoaster of deciding whether to sunset or pivot a product, the difference betwee…

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Rant Therapy - I’m So Over 4 Day Weeks! 4:20

23d ago4:20

4:20

The best (and cheapest) therapy for those small things that get under your skin is sometimes a good venting session so you can get it off your chest and move on with your life! And if you’re not privy to the first-hand vent-a-thon, then being a fly on the wall listening is hopefully equally therapeutic and also maybe entertaining. Welcome to Rant T…

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E29: The AI Performance Gap Is About to Become Permanent. Here's Which Side You're On 43:48

24d ago43:48

43:48

Wall Street Journal just proved what every founder already knows: AI isn't leveling the playing field - it's making superstars 10x better while average performers fall further behind. You have 18 months before this gap becomes permanent. Story 1: AI is widening the performance gap (not closing it): Wall Street Journal research: AI makes superstars …

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EP. 332 DOUBLE FAILURE WITH SAUCE ON IT 1:08:36

28d ago1:08:36

1:08:36

SUPPORT THE LADS AND GET BONUS EPISODES AT WWW.PATREON.COM/WORSTPOSSIBLETIMELINE Learn more about your ad choices. Visit megaphone.fm/adchoicesBy Worst Possible Productions & Sound Talent Media

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E28: Infrastructure Owners Are Killing Middlemen. Here's How to Know If You're Next. 33:14

28d ago33:14

33:14

FICO changed their licensing model and two public companies lost 10-20% in a single day. ChatGPT launched shopping with Shopify. European founders are fleeing to San Francisco. These look unrelated - but they're all the same story: Infrastructure owners are systematically eliminating middlemen. Story 1: How FICO destroyed $5 billion in market cap o…

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The Body Doubling Episode 26:50

28d ago26:50

26:50

If you’ve had trouble lately focusing or being productive, this episode is for you. We’re talking about a concept called body doubling, and it’s something Carolyn and I have been employing to work through big projects, knock out mundane to-do items, or simply tackle our day job. In fact, it’s become one of the most effective solutions—and some days…

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E27: Junior Jobs Are Disappearing and Nobody's Talking About It. 38:15

30d ago38:15

38:15

Yale says AI isn't displacing jobs. Stanford says it's destroying junior roles. Here's why they're both right - and what it means if you're young, building a company, or hiring right now. The AI job displacement debate - Yale vs Stanford: Yale report (33 months of labor data): No proof AI is displacing jobs, we're very early in cycle Stanford repor…

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How Slack Builds Products People Love to Use, with Chief Product Officer Rob Seaman 35:48

29d ago35:48

35:48

Private companies can be mission-driven. And in today's market, they have to be. Rob Seaman, Chief Product Officer at Slack, joins Jess Carter to discuss how leading with purpose helps build better teams and better products. Rob shares lessons from Slack's integration with Salesforce, including the importance of staying close to customers, balancin…

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Rant Therapy: What's Next? 7:06

1M ago7:06

7:06

By Brierley Horton, MS, RD & Carolyn Williams PhD, RD

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E26: Governments Are Giving Away ChatGPT for Free (Your Startup Should Too) 33:39

1M ago33:39

33:39

Governments are giving away ChatGPT Plus subscriptions for free to entire populations. Private companies are bundling AI tools to close productivity gaps. If your startup isn't doing this for employees, you're already behind. Governments subsidizing AI access for citizens: UAE planning to give all citizens free ChatGPT Plus ($20/month) - tens of mi…

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E25: AI Will Copy Your MVP in Three Weeks: Why I Never Build Single Product Companies Anymore 27:39

1M ago27:39

27:39

AI will copy your MVP in three weeks (maybe less). This is why I never build single product companies anymore. Revenue diversification beats revenue projection - here's the ecosystem model that actually survives. The new brutal reality of building software: Claude 4.5 Sonnet just dropped - experienced developers rebuild 80% of products in days, not…

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Creatine: What Are the Benefits and How Much Should I Take? 34:24

1M ago34:24

34:24

Creatine is everywhere right now. While the supplement has been popular for years among gym rats, the benefits of taking creatine now far surpass gaining muscle strength—and especially for women. What are those benefits? How much creatine should you be taking? When should you take it? And will it make you gain weight? We answer all of these questio…

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E24: Why My Friends Making $500K at Google Regret Their Careers (And What I Learned About Freedom) 21:53

1M ago21:53

21:53

I have a friend who makes $500K at Google. He's worked there 15 years, made Managing Director, and he told me: "I've basically given up and I'm just collecting my paycheck." This is what happens when you trade freedom for money. The pattern I keep seeing across industries and countries: Waterloo classmate at Microsoft making $250K base - quit becau…

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Rant Therapy: Lightbulbs 5:28

1M ago5:28

5:28

The best (and cheapest) therapy for those small things that get under your skin is sometimes a good venting session so you can get it off your chest and move on with your life! And if you’re not privy to the first-hand vent-a-thon, then being a fly on the wall listening is hopefully equally therapeutic and also maybe entertaining. Welcome to Rant T…

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E23: The Startup Playbook Just Changed: Three Stories That Reveal How to Build in 2025 28:45

1M ago28:45

28:45

Three stories from this week reveal something fundamental changing about how you build businesses in 2025. The old VC playbook is dead - here's what's actually working now. Story 1: Founders walking away from traditional VC (and it's strategic, not desperate): Mercury surveyed 1,500 early-stage startups about funding in 2025 66% of founders changed…

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E22: The $60 Million GitHub Move That Just Killed Startups (And Why That's Perfect for Bootstrap Founders) 23:35

1M ago23:35

23:35

While everyone argues about which AI model is best, the smart money is building connectors that work with ALL of them. This week GitHub and Microsoft just made this approach inevitable - and if you're still building custom integrations for every AI tool, you're about to feel very stupid. What is MCP and why the scary name doesn't matter: MCP = Mode…

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Pelvic Floor Dysfunction: What Is It and Why Is Everyone Suddenly Talking About It? 31:26

1M ago31:26

31:26

Why is everyone talking about their pelvic floor lately? This really wasn’t something we ever heard discussed 10 years ago. But in reality, 1 out of 2 childbearing women experience pelvic floor dysfunction. And thanks to the interest in menopause, we’re learning that your likelihood increases as estrogen levels decrease. The hard part about pelvic …

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EP. 331 IN THE HEAT OF IT 1:08:14

1M ago1:08:14

1:08:14

FOR OVERTIME + BONUS EPISODES, SUPPORT THE LADS AT WWW.PATREON.COM/WORSTPOSSIBLETIMELINE Learn more about your ad choices. Visit megaphone.fm/adchoicesBy Worst Possible Productions & Sound Talent Media

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E21: Zero Meetings: How I Run Two Companies Without a Single Recurring Meeting 19:51

1M ago19:51

19:51

I looked at my calendar this week: zero meetings. Last week: zero meetings. Most founders think this is impossible, but here's what six years taught me - meetings don't make you productive, they make you FEEL productive. The meeting theater that's killing startups: Pre-COVID: Weekly all-hands, daily standups, planning meetings felt "professional" P…

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The Value of Project Managers with Not the Worst PM's Kelly Vega 38:36

1M ago38:36

38:36

From TikTok skits to tech leadership, Kelly Vega shows why project managers are more than task trackers. As program director at VML and the creator of Not the Worst PM, Kelly has built a following by turning the chaos of project management into relatable, entertaining content. In this episode of Data-Driven Leadership, she joins Jess Carter to shar…

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Rant Therapy: Stupid F***ing Fantasy Football 5:21

1M ago5:21

5:21

The best (and cheapest) therapy for those small things that get under your skin is sometimes a good venting session so you can get it off your chest and move on with your life! And if you’re not privy to the first-hand vent-a-thon, then being a fly on the wall listening is hopefully equally therapeutic and also maybe entertaining. Welcome to Rant T…

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E20: Why I Ignored 60% of My Customers for 5 Years (Why Every Startup Should Go Global from Day One) 21:37

2M ago21:37

21:37

For 5 years building SimpleDirect, 45-50% of our blog traffic came from UK, Germany, France, and South America. I turned away all those paying customers because I thought "global" meant "complex." I was dead wrong. Every founder should build globally from day one - it's easier than perfecting a single local market. The "focus" trap that costs milli…

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E19: How I Learned to Learn (And Why It's Your Best Business Skill) 23:52

2M ago23:52

23:52

A year ago I ordered takeout daily, couldn't speak French, and avoided the gym. Today I cook my own meals, read French business newspapers, and work out every day. The secret wasn't willpower or dramatic changes - it was discovering that learning how to learn is the ultimate founder superpower. The learning misconception that kills progress: We thi…

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Hydration: Your Most Common Questions Answered 30:24

2M ago30:24

30:24

We’ve talked about hydration before. And if we had to guess, every one of us is walking around with a Stanley or Owala because you know the importance of hydration. But is there really more to know about hydration than just drink water? We’ve had listeners send us a variety of questions over the past few months: How do you stay optimally hydrated? …

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Rant Therapy: Is Your Focus Off Too? 6:04

2M ago6:04

6:04

The best (and cheapest) therapy for those small things that get under your skin is sometimes a good venting session so you can get it off your chest and move on with your life! And if you’re not privy to the first-hand vent-a-thon, then being a fly on the wall listening is hopefully equally therapeutic and also maybe entertaining. Welcome to Rant T…

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E18: Why I'm Shutting Down My 5-Year Startup (Hard-Learned Lessons for Founders) 18:05

2M ago18:05

18:05

After 5 years building SimpleDirect Financing from my university dorm to today, I'm shutting it down. This isn't about failure - it's about the brutal lessons every founder needs to learn about attachment, external dependencies, and why starting with principles beats chasing opportunities. The real cost of founder attachment: Spent 5 years attached…

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E17: Why I Stopped Checking My Metrics 20 Times a Day (And Everything Started Working) 14:12

2M ago14:12

14:12

A few years ago I checked my Y Combinator application 20+ times a day. Last month I was obsessively refreshing Twitter analytics every few hours. Then I stopped caring about numbers completely - and everything started working better. The brutal reality of metric obsession: Checked YC application status obsessively after 2021/2022 interviews - made …

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E16: Why I'm Worried About My Friends' "Successful" Acquisitions 20:58

2M ago20:58

20:58

Why undisclosed acquisition prices should worry you. A bootstrap founder's analysis of the "successful" startup exits that may not be so successful - and why starting over in your thirties isn't a winning strategy. The pattern that's making me worried: Two friends' startups acquired in past two months, five in past two years All labeled "successful…

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Is Methylene Blue a Natural Solution for ADHD? 24:26

2M ago24:26

24:26

A few months ago, Carolyn and I were sitting in a bar with a friend lamenting over our ADHD-like symptoms. Her suggested solution? Methylene blue supplements and she began to tell us how it boosted focus and attention span. Before we could say Amazon, Carolyn was adding the supplement to her shopping cart. The next day, before I purchased, I did so…