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AI & I

Dan Shipper

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Learn how the smartest people in the world are using AI to think, create, and relate. Each week I interview founders, filmmakers, writers, investors, and others about how they use AI tools like ChatGPT, Claude, and Midjourney in their work and in their lives. We screen-share through their historical chats and then experiment with AI live on the show. Join us to discover how AI is changing how we think about our world—and ourselves. For more essays, interviews, and experiments at the forefron ...
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Here’s a scary fact about adulthood. We stop asking questions. We lose the playful curiosity and creativity that we had as children. And it’s a shame. Questions are gateways to our deepest desires, insecurities and dreams. Reflecting on a deep question takes us one step closer to a life well-lived. Each week, we’ll ponder and debate one of life’s thorniest questions. We’ll explore ambition, careers, money, relationships, productivity and psychology — all in the pursuit of living an Examined ...
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Making Media

Colossus | Investing & Business Podcasts

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How to build a media business by two outsiders learning the craft. Matt Reustle and Dom Cooke have decades of experience in investing but almost none in the media industry. In each episode, they talk to great media operators, document their own media building efforts, and dissect their favorite business content. Join these two content junkies in their fight to save long-form media against the attention span crisis. Join the resistance. Learn more and stay up to date at www.joincolossus.com. ...
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This episode is sponsored by Command Bar, an embedded AI copilot designed to improve user experience on your web or mobile site. Find them here: https://www.commandbar.com/copilot/ Dwarkesh Patel is on a quest to know everything. He’s using LLMs to enhance how he reads, learns, thinks, and conducts interviews. Dwarkesh is a podcaster who’s intervie…
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I just turned 45 years old, which means I've lived 60.3% of my actuarial lifespan. I have way less hair, but at least I've held on to my six pack. I left Wall Street so that I could have time freedom, raise my kids and surf every day, and I learned a few lessons along the way. I’ll share 45 of them on workaholism, borderline alcoholism, how to cope…
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Our guest today is Matthew Sherry, co-founder and CEO of Platform Media. Founded in 2021, the business is home to some of the UK’s biggest podcasts and was acquired earlier this year for an eight-figure sum. The business was founded to solve the two biggest problems in podcasting: distribution and monetization. Through a savvy social strategy and b…
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Steph Smith is the ultimate internet explorer. I spent an hour talking to her about the future of creating on the internet in the age of AI. She’s our first-ever repeat guest, and if you watch the episode you’ll see why: It’s a curious, fun, experimental romp through the best of the digital world. We try out four underrated AI products, go through …
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Imagine you’re about to have your first kid. But your career is muddling along and you don’t have a dependable source of income. You need a plan to grow your wealth. Quickly. And it happens to be the start the pandemic where ALL crypto projects are going gangbusters. Writer and serial entrepreneur Nat Eliason saw an opportunity to get rich and hatc…
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This week on Bet the Process, Matthew Trenhaile (@Matthew_Trench on X) joins to take the record for longest BTP episode yet. Matthew is a betting expert and former bookmaker who shares his opinions on a wide range of topics, including market making, the US presidential election, risk management by very successful bettors, and much more.…
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Dr. Bradley Love is building a tool that can predict the future. Dr. Bradley Love is transforming neuroscience research with AI. He's the creator of BrainGPT, a large language model that can predict the results of neuroscience studies—before they’re conducted. And it performs better than human experts. We spent 90 minutes exploring how AI is reshap…
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There’s a simple playbook for happiness. One we’ve been taught since we were kids. Study hard, get a good job, climb the ladder, make a bunch of money and then you’ll be happy. So why do so many of us feel unfulfilled, lost and rudderless? This week we speak with Stephanie Harrison, an expert on the psychology of happiness and the author of New Hap…
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IQ gets all the attention. It’s the raw brain power that wows us. But EQ, or emotional intelligence, might be even more powerful. It provides the finesse to interact with peers, confidence to pitch new investors and charisma to recruit top talent. IQ is something we’re born with. But what about EQ? In this episode, we’ll discuss seven ways to devel…
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Claire Vo built ChatPRD—an on-demand chief product officer powered by AI. It’s now used by over 10,000 product managers and is pulling in six figures in revenue. The best part? Claire has a demanding day job as the CPO at LaunchDarkly. So she built all of ChatPRD herself—over the weekend—with AI. I sat down with Claire to talk about how ChatPRD wor…
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From playing online poker to pay for college, to starting a gardening lifestyle business that turned into a $40 million empire, Kevin Espiritu’s journey is jaw-dropping. He provides a candid look at his obsessive personality trait that fueled his success, and discusses his changing relationship with money as his business scaled. We cover following …
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Author Geraldine DeRuiter reached the dizzying heights of publishing her first book, then experienced the more muted satisfaction of her second. She’s grappled with the realization that external achievements can't resolve core belief of not being "good enough." We contemplate the limitations of external accomplishments in solving our deepest insecu…
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An interview with best-selling sci-fi novelist Robin Sloan One of my favorite fiction writers, New York Times best-selling author Robin Sloan, just wrote the first novel I’ve seen that’s inspired by LLMs. The book is called Moonbound, and Robin originally wanted to write it with language models. He tried doing this in 2016 with a rudimentary model …
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We use it to find bestselling author Steven Berlin Johnson’s next project. I sat down with bestselling author Steven Johnson to see if we could come up with a concept for his next project—using AI. The results were amazing. We loaded 200,000 words of NASA transcripts and all of Steven’s reading notes since 1999 into NotebookLM, Google’s personalize…
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When I was 22 years old, I worked 100 hours a week as an investment banker on Wall Street. I daydreamed about the day when I could retire, move to the beach and surf every day. When the board meeting would become the board meeting. That day came at age 35. I didn't retire or hit my "number." But I had enough to make a bold pivot and say, "Okay, now…
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This week on Bet the Process, Preston Johnson joins to talk Crawley Town F.C. and their recent success, including player development, playing style, and his experiences with online criticism. Jeff and Rufus also touch on a somber topic regarding Grayson Murray, and share some personal thoughts.By Bet The Process
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Do you feel like AI is a solution in search of a problem? I used to feel the same way. ChatGPT was basically a glorified search engine for me. I'd ask it things like "how do I make the fluffiest pancakes?" But after talking to AI expert Dan Shipper, I realized I was just scratching the surface. Dan showed me how to use AI to negotiate with vendors,…
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Learn how the smartest people in the world are using AI to think, create, and relate. Each week I interview founders, filmmakers, writers, investors, and others about how they use AI tools like ChatGPT, Claude, and Midjourney in their work and in their lives. We screen-share through their historical chats and then experiment with AI live on the sho…
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Death is scary. We don't want to think about the infinite unknown. And being a speck not more than star dust. But what if contemplating death is the way you live a fuller, more purposeful and happy life? [Episode 50] Maura is the founder of Hello Mortal a platform dedicated to familiarizing us with the great unknown.Learn more about Maura: • Maura'…
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This week on Bet the Process, The Shipper (@ShipTheJustice on X/Twitter) joins to discuss his criticisms of the previous Kirk Evans episode, describe what a “roark” is, and dive into what motivates him with sports betting. Rufus also shares his story of betting on Xander Schauffele in the PGA Championship.…
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2015. German Chancellor Angela Merkel was the Person of the Year, Instagram Stories didn’t exist and Uptown Funk was the most popular song in the country. And I left Wall Street with a newborn daughter and no real plan. In the past 9 years, I’ve learned about money, envy, simplicity and relationships. And I want to share all of it with you. [Episod…
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Our guest today is Dan Shipper, the co-founder and CEO of Every. Every started at the beginning of the pandemic as a bundle of business newsletters written by different authors. While writing is still at the heart of the business, the model has shifted focus to a daily newsletter that is an essay on technology, productivity, or AI. Dan and his team…
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New York Times journalist Kevin Roose has 18 new friends—none of whom are human. Kevin formed a collection of “friends”—AI personas with distinct personalities and backstories—using apps like Kindroid and Nomi. Among these were fitness guru Jared, San Francisco-based therapist Peter, and pragmatic trial lawyer Anna. He talked to them every day for …
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Imagine being unable to afford a cup of coffee in your 20s. Then being able to afford the entire coffee shop in your 30s. Some “money issues” may arise — particularly for the next generation. Michael Perry had a big exit to Shopify but describes his struggles with self-hatred, not showing up well as a dad and helping his kids become resilient and k…
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5% of Americans are in open relationships. I used to think that this world was for hot 20-somethings frolicking around house parties. Whether it’s open marriages, swinging or polyamory — the taboo is lifting and trend is definitely coming to a gentrified neighborhood near you. What’s most fascinating? For these relationships to succeed, you need a …
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This week on Bet the Process, Kirk Goldsberry joins to discuss his career trajectory from geography to sports analytics, the importance of visualization in bridging the gap between data collection and explaining findings, and how NBA officiating has changed. Jeff and Rufus also chat about the NFL draft and criticism of their previous episode with C…
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Nick Dobos, maker of the #1 programming GPT, on prompt-gramming with AI You can go from having an idea to deploying a live website in minutes. All you have to do is prompt Grimoire, the number-one custom GPT for programming, with an image or even a single word about your idea. As you watch the LLM process your request, Grimoire works with a web hos…
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My wife and I did a guided psychedelic journey together. It was fully-assisted and we put on sleeping masks and went inward. It showed me so much about my emotional distancing, inner critic, people pleasing tendencies and why deep inside I’m nothing but a squishy loveball. [Episode 46] —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep…
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This week, we bring you two titans of the podcasting world, Tim Ferriss and our very own Colossus chairman, Patrick O’Shaughnessy. We’re biased, but I think these two are two of the best interviewers in the world, and they recorded this conversation on Invest Like the Best for the 10th anniversary of Tim’s podcast. Matt and I thought you, our preci…
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The future of AI technology isn’t just faster or more powerful—it’s empathetic. My guest for this episode, Alan Cowen, is leading the charge with the first-ever emotionally intelligent AI. Alan is the co-founder and CEO of Hume, an AI research laboratory developing models trained to identify and measure expressions of emotion from voice inflections…
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The traditional way of getting a great job is being turned upside down. Social media, personal brands and a digital portfolio of work now play a key role in landing your dream job. Today’s guest has harnessed both paths. He’s a Columbia MBA grad starting a new division within RobinHood. He’s also the world’s greatest LinkedIn shitposter. You’ll lea…
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Learn how to use philosophy to run your business more effectively Reid Hoffman thinks a masters in philosophy will help you run your business better than an MBA. Reid is the cofounder of LinkedIn, a partner at venture capital firm Greylock Partners, the host of the Masters of Scale podcast, and a prolific author. But before he did any of these thin…
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The Internet has created a gold mine of opportunity. You can use it to find your next job. Or business idea. The crazy part is that people are telling you — through Google searches, Reddit Posts and social media — what they actually care about. And you can use that information to come up become an idea machine. [Episode 44] Steph Smith is a growth …
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Our guest today is sports media veteran Mike Stricoff. Mike spent a decade producing live sports talk on national TV, first working at MLBN before moving to Fox Sports, where he helped launch Undisputed. Mike worked on that show alongside Skip Bayless, Shannon Sharpe, and others as the main line producer. In 2017, he left national TV for tech, goin…
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Seth-Stephens Davidowitz wrote a book in 30 days—and he did it with ChatGPT. Seth is a data scientist, economist, and author who challenged himself to write a book—Who Makes the NBA?—in less than 1 month after realizing how fast he could work by using ChatGPT plugin Advanced Data Analysis. But along the way he discovered something else: Writing wit…
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This week on Bet the Process, Rufus flies solo and interviews Will Haskett, a golf broadcaster and author, about some of his favorite calls, quantifying golfer’s nerves, the biggest insight he’s learned from the PGA tour, and the upcoming Masters. Sponsored by Splash Sports www.splashsports.comBy Bet The Process
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I’ve been told I look Brazilian, Greek and Hawaiian. I relished it because I didn’t want to be called Asian. Especially not in 80s and 90s, where the stereotypes of docile nerds (who like math and kung fu) reigned supreme. Now at age 44, not only are Asian men having a “moment” — I’ve gone inwards to reevaluate my identity, heritage and how this ha…
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Going to therapy usually evokes laying on a couch and talking endlessly about your childhood. But what if all the stress and healing are located in your body and could be felt and accessed through your inner monologue. That’s the approach of Internal Family Systems (“IFS”) which helps you tap into your various “parts,” like your Inner Critic, Perfe…
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Nicholas Thorne is building Squarespace for the AI age. It’s called Audos, and it’s an AI chatbot to help any entrepreneur go from idea to: - Pitch deck - Working website - Custom GPT - User interviews with real customers All in just a few minutes. And he did it using ChatGPTapp. It’s AI all the way down—and it’s one of the most impressive AI busin…
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