All-In PodcastJake Paul & The Chainsmokers: Turning Fame into Funds, Jake Enters Politics? & Venture Bubble Signs
All-In Podcast
Jake Paul Introduced As Provocateur 0:01
The piece opens with clips framing Jake Paul as brash, self-absorbed, and yet remarkably successful, someone who treats attention itself as a currency. He describes his two life goals as becoming a boxing world champion and selling a company for a billion dollars, and insists he never followed social media trends but set them himself.
From Vine To Vine's Collapse 1:30
Jake explains he grew up always gaining followers, doing content before it was fashionable, driven by a love of creativity rather than chasing virality. When Vine's top twenty creators, including him, demanded a million dollars each per year in exchange for staying on the platform, Vine refused, the creators left for Facebook, YouTube, and Snapchat, and within two months Vine shut down. He also reflects on livestreaming culture, coining the term "YouTuber disease" for creators who say outrageous things purely to chase views, and argues platforms like YouTube can't police this alone since rivals like Twitch, Kick, and TikTok would simply absorb the audience instead.
Boxing, MVP, And Investing 8:00
He recounts starting boxing on a dare against two UK brothers, training hard for three months, and knocking them out in Manchester, which pushed him into professional boxing and building MVP, now managing 400 fighters and merging with PFL to challenge the UFC, which he criticizes for paying fighters only about fifteen percent of revenue compared to fifty percent in other leagues. He also describes angel investing since age eighteen, backing OpenAI, SpaceX, and Cognition, helping shape OpenAI's Sora app, and raising a hundred million dollar fund he wants judged against firms like Sequoia rather than dismissed as celebrity money, while warning that chasing attention can breed dishonesty in media and content.
Future Plans And Politics 16:31
Looking ahead, Jake describes his ventures as a self-reinforcing cycle of fighting, investing, and content creation, plus a foundation running forty free youth boxing gyms. Asked where he sees himself at forty, he answers politics, arguing future leaders will need an organic online following, citing Trump and Nick Fuentes as examples of this shift.
How The Chainsmokers Formed 21:30
The two musicians explain how they met through a mutual friend. One of them had already started a group called The Chainsmokers with someone else, but that partnership fell apart, leaving him looking for a third member around 2011 or 2012. The other was finishing his studies at Syracuse University and writing music on the side. They met, hit it off instantly, and decided to form a group together, not realizing at the time it would become the most important decision of their lives. Fourteen years later they remain best friends and close collaborators, both in music and in other ventures.
Chasing Sound While Fans Want Nostalgia 23:30
You hear them describe the tension between wanting to experiment and fans wanting the old hits. They admit that seeing a critic on Twitter accuse them of writing the same song over and over pushes them to try new things, though they say that criticism does not really shape their direction. They follow their own creative instincts instead of sticking to one genre. They also notice a strong current of nostalgia in music right now, pointing back to January 2016 as a breakout year for them, and wonder how to balance what feels exciting to create with what fans associate with that earlier sound.
Building An Audience Before Streaming 25:01
Starting out in 2012, before streaming existed in its current form, they built momentum through remixes and a blog-tracking site called Hype Machine, which ranked artists by blog mentions and likes. One of them dug into the site's backend, found the bloggers behind each post, and sent them funny, personal emails instead of generic pitches, which college-age bloggers responded to. Within their first year they went from unknown to having about 30 songs topping that chart. They note that today's music industry is flooded, with 300,000 songs uploaded to Spotify daily, making the old blog-based playbook obsolete and leaving artists facing a much more fragmented, AI-shaped landscape.
From Live Shows To Venture Investing 29:30
Live performance remains a major income source, especially since they started as DJs, which makes touring more economically efficient than for a full band. Their entry into venture capital grew out of their tech-friendly instincts, including early use of a conferencing tool called Tilt for tour data, and their appeal to brands as successful artists. What drew them in was not passive income but the chance to build real relationships with founders and add value, investing in areas like cybersecurity, AI, infrastructure, and health tech through their firm Good Games Ventures, where they take early-stage, non-lead positions and see themselves as a supporting player rather than the headline investor.
Fame As Leverage And Liability 37:01
They describe using their name and network to open doors for founders, from making warm introductions to helping with branding, since technology today is easier to copy and harder to defend. At the same time they acknowledge skepticism from institutional investors who admire their work but hesitate to back a fund tied to their celebrity, fearing headlines if something goes wrong. Their response is to let returns speak for themselves over time, since investors have short memories for controversy but long memories for performance, and turning any asset, whether fame or expertise, into real results is what ultimately earns credibility.
Investing Beyond the Hype 40:30
There is enormous liquidity flowing into everything right now, and the hard part of being a good investor is backing ideas, founders, and companies that feel real and substantial rather than chasing the promotional side of venture capital. It is easy to invest in companies you think will rise in value without having any long-term vision for them. Real conviction looks like the early bets on Airbnb or Uber, which were not obvious choices at the time.
How Uber and Robinhood Got Rejected 41:30
Travis was introduced to 21 angel investors and nineteen turned him down, leaving only three, including First Round Capital. The ones who passed said the taxi business was too dirty and risky, worried that someone could get hit by a car and the firm would be liable, and they only wanted software, not operations. Robinhood faced similar mockery during its Series A, even from people working there before they left. One investor admits his own hesitation on Robinhood came from ego and his earlier Facebook experience with growth mechanics he disagreed with, calling it a billion-dollar mistake he still regrets. He also mentions holding Uber and Robinhood stock for over a decade without selling, buying more Robinhood shares at nine dollars, and notes that founders like Vlad keep launching new products, since real execution cannot be faked. He adds that many top investors, like Mike Moritz, a former journalist, or John Doerr, who sold Intel chips, had no prior expertise in the fields they later dominated, showing curiosity and critical thinking matter more than credentials.
Picking VC Funds to Back 45:00
When choosing which venture funds to invest in, the speaker weighs deal flow, decision-making skill, and then the harder question of when to double down, distribute profits, or sell. Nearing its seventh year, the fund has just seen its first real liquidity event, from a company called Underdog Fantasy, calling it a great feeling to finally return cash to investors after building about seventy five percent of the model. He credits Brian Singerman's two-hour talk on the importance of following on, and praises Founders Fund's approach of forcing a fund to put twenty five percent of capital into one conviction bet per fund. The group discusses building a growth fund and using SPVs to let family offices and early investors buy liquidity in late-stage deals like Zipline, Fast, and Atoms, while also buying into a five to six hundred million dollar round, similar to how Sequoia and Founders Fund both buy and sell in companies like Stripe or SpaceX.
Redefining a Billion Dollar Company 50:00
The scale of companies now is striking, since a billion dollars used to sound like an absurd, meaningless number and now refers to actual revenue. The speaker says he now defines a billion-dollar company by revenue rather than valuation, citing one portfolio company at seven hundred million in revenue as just three hundred million away from that mark. The conversation turns to secondary sales and how later-round investors sometimes pay two or three times the earlier valuation with little change in underlying performance, which is flagged as classic bubble behavior and a signal to take some money off the table. The episode ends with lighthearted banter about tequila, a dance floor performance, and closing remarks about turning fame and attention into sustained hard work over many years.
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