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Noah Kahan’s TikTok verse that turned into sold-out stadiums
Sam tells the underdog story of singer-songwriter Noah Kahan, who felt stuck during the pandemic and started posting unfinished music on TikTok. A single 20-second verse unexpectedly went viral, pushing him to finish the song and ultimately leading to major sold-out shows.
- •Sam describes Noah Kahan’s early career as modest success with uncertainty about making it
- •During the pandemic, Noah returns home, feels depressed, and experiments with posting on TikTok
- •A quickly written verse for “Stick Season” gets little traction at first, then explodes overnight
- •The viral moment motivates him to complete the song and release it
- •Within a few years he’s selling out major venues and bringing his parents on stage
Being “one hit away”: why creators shouldn’t delete too early
Shaan reflects on the “one hit away” dynamic in content and the arts, where past failures can be misleading and breakout success can arrive suddenly. He shares how close he came to deleting a Twitter thread that became his biggest viral moment.
- •Shaan argues content is an exception where a single breakout can change everything
- •Earlier work can produce “false negatives,” so lack of initial traction doesn’t prove it’s bad
- •He connects the idea to a prior example of a last-ditch product attempt taking off
- •Sam notes the implication: you need to take lots of shots to get a hit
- •Shaan recounts nearly deleting a long thread that later reached massive readership and changed his social graph
Shaan’s “amateur singing talent” obsession (and why it works)
The hosts riff on how compelling raw, unpolished talent can be compared to polished celebrity performances. Shaan explains why he’s drawn to clips of unexpected singers and early-stage ability.
- •Shaan describes loving moments where someone unexpectedly reveals strong singing ability
- •He contrasts polished famous performances with raw, surprising amateur clips
- •The segment ties back to the appeal of watching progress in public
- •The conversation sets up other discovery stories in music
Ed Sheeran’s early bad singing and the break that changed everything
Shaan shares an Ed Sheeran clip to emphasize that skill comes from practice, not being “born talented.” He then tells the story of Sheeran’s Los Angeles hustle and how Jamie Foxx’s circle helped propel him forward after an open-mic discovery.
- •A clip illustrates Ed Sheeran sounding terrible at a young age and emphasizing practice
- •Shaan recounts Sheeran traveling to LA to break into the scene
- •Jamie Foxx’s business manager spots Sheeran at an open mic and brings him onto Foxx’s radio show
- •Sheeran says he’s not signed and is homeless; Foxx offers him a place to stay
- •A high-pressure club performance wins over a skeptical crowd and becomes a proof point that he can connect
Eric the Eel: the Olympics wildcard swimmer who just tried to finish
Shaan tells the story of Eric from Equatorial Guinea, a wildcard entrant in the 2000 Olympics who had minimal training resources. The drama peaks when his competitors false start, leaving him alone in the pool, struggling to complete 100 meters as the crowd rallies behind him.
- •Shaan explains the wildcard pathway that lets some countries send an entrant
- •Eric gets eight months to prepare despite having little experience and no coach
- •Training constraints include limited access to a small hotel pool and improvised practice in open water
- •At the event, other athletes and coaches help him with last-minute basics like goggles and technique
- •He finishes to a roaring crowd and later becomes a national coach, embodying the Olympic spirit
CarEdge: father-son YouTube credibility turned into a car-buying business
Sam explains how a former car-dealership manager and his son started by posting negotiation and dealership-insider videos on YouTube. That audience became the foundation for CarEdge, a suite of tools and services that help buyers negotiate or have the team broker a car purchase.
- •The business begins as a son interviewing his dealership-expert father on YouTube
- •They grow quickly with a simple, “janky” filming style that audiences liked
- •CarEdge offers different products: information tools for negotiating and a paid service to buy the car for you
- •Sam describes typical car broker economics and how CarEdge modernizes the model with a startup-style site
- •Sam shares that the founders disclosed the business is doing roughly $10M/year revenue and has a large YouTube audience
Why wholesome family business dynamics can be a brand advantage
The hosts discuss why the father-son dynamic helps CarEdge’s brand feel trustworthy and likable. They broaden the discussion to other parent-child business partnerships and debate the risks and rewards of mixing business with friends and family.
- •Shaan notes the site’s wholesome imagery reinforces the father-son brand identity
- •They compare parent-child partnerships to other examples they’ve encountered on the podcast
- •Sam highlights how rare-but-powerful the right parent-child collaboration can be
- •Shaan argues working with family and friends can be a ‘cheat code’ when it works
- •They touch on the downside: when it goes wrong, it can be deeply painful
Mohawk Chevrolet’s TikTok ‘Office-style’ series and the power of having nothing to lose
Sam shares a standout example of a local dealership creating a narrative TikTok series with a 23-year-old social media hire at the center. Shaan reacts with amazement at the production and argues that low-stakes environments enable creative risks that big corporate brands can’t take.
- •A rubber-duck prank video becomes the spark for a multi-episode comedic series
- •The series uses interviews, cutaways, and improvisation to build recurring characters and plots
- •Major brands comment on the videos, and viewers ask for more episodes like a real show
- •Sam references an interview describing how they find ‘gold’ through unscripted filming
- •Shaan notes a small dealership can experiment freely because it has little reputation risk compared to a corporate brand
Pokémon Sleep: gamifying wellness into a $100M+ revenue app
Shaan introduces Pokémon Sleep, a sleep-tracking app that turns bedtime into a game where sleep quality leads to catching Pokémon. He cites user reactions and explains how in-app purchases drive revenue, framing it as a rare example of health tracking made genuinely fun.
- •The app tracks sleep by having users place their phone near them while they sleep
- •Better or different sleep patterns translate into catching Pokémon and progress in the game
- •Shaan says the app has done over $100M in revenue and describes it as especially big in Japan
- •He reads user anecdotes describing the app helping them maintain a consistent bedtime despite imperfect accuracy
- •The monetization is explained as in-app purchases and bundles
A bigger idea: social, game-like health tracking (steps as Mario Kart)
Building on Pokémon Sleep, Shaan argues most health tracking is overly quantitative and not fun. He proposes a more social, competitive framing for step tracking that turns daily movement into a playful race among friends.
- •Shaan critiques typical step tracking as repetitive and mostly ‘me versus me’
- •He proposes a daily race concept where friends’ progress is visible in real time
- •He describes the motivational effect of being passed and trying to catch up
- •He suggests customization and playful visuals as a layer on top of the same data
- •The broader theme: ‘fun variants’ can drive behavior change better than pure metrics
Competitions that work: energy-burn challenges and ‘Sober October’-style motivation
Sam shares an experience competing with friends using a fitness wearable, turning a month into a contest for who burned the most energy. They agree that simple competition mechanics reliably motivate behavior, even if they can feel exhausting.
- •Sam describes a January competition with friends tracked by a wearable to measure exertion
- •The contest mindset creates urgency to move more to keep up with others
- •They connect the idea to Joe Rogan’s friend-group challenge concept
- •They note social proof and public sharing of step counts increases compliance
- •The segment reinforces the value of friendly rivalry for habit formation
Nick Gray’s ‘Done’ system: ultra-simple accountability in a WhatsApp group
Shaan recounts a conversation with Nick Gray about keeping momentum from the hosts’ previous challenge by using a minimalist accountability loop. The core mechanism is a WhatsApp group where participants can only post one word—“done”—and nudges are sent when someone falls off.
- •Nick Gray praises the earlier ‘My First Muscle’ challenge as fun and sticky with friends
- •The ‘Done’ format restricts chat to one word to keep it simple and repeatable
- •Seeing others post ‘done’ creates pressure and motivation to complete the daily action
- •Shaan describes follow-up nudges when someone hasn’t posted for several days
- •They discuss restarting the challenge with clearer timing so listeners can prepare
Conference lessons: ‘the best advice is free’ and doing a 360 review of life
Shaan shares notes from Andrew Wilkinson’s event, arguing great advice tends to be either extremely simple or shared freely by people who don’t need to monetize it. He also describes insights from Patrick Campbell about avoiding major moves after a sale and using structured introspection like a life ‘360’ and personal scorecards.
- •Shaan describes Andrew Wilkinson’s ‘Interesting People’ event and the value of hearing real feedback loops from listeners
- •He argues the best advice is free because it’s either simple common sense or given freely by very successful people
- •He recounts Patrick Campbell’s view: avoid major purchases or moves for a period after selling a company
- •Shaan describes a ‘life 360’ process involving interviews and deep questioning to clarify values and patterns
- •Patrick’s scorecard buckets include wins, accepted weaknesses, areas to improve, and ‘losses I will no longer live with’
Public speaking whiplash: Shaan’s failed talk, then a breakout-session win
Shaan analyzes why one of his talks flopped—he tried an unprepared story and delivered a downer topic at the wrong time of day. He contrasts that with a successful breakout session where he shifted the room’s energy, made it interactive, and focused on state change before information.
- •Shaan describes attempting a story-driven opening with minimal preparation and feeling it fall flat
- •He explains how focusing on failures created a negative ‘state change’ for a tired audience
- •He reflects on the risk of trying to be different: it’s great when it works, but ‘weird’ when it doesn’t
- •For the breakout, he rearranges the room into a circle to change dynamics and increase participation
- •He uses crowd work and a quick physical reset to boost energy, emphasizing that good decisions come from good energy
Publisher timestamps
- 0:00The Jewish Ed Sheeran
- 10:22The actual Ed Sheeran
- 15:00Eric the Eel
- 20:00How CarEdge is quietly crushing it
- 29:21How a car dealership is pulling millions of views on TikTok
- 33:07$100M+ Pokemon sleep tracking app
- 35:55Nick Gray's new thing
- 39:37“The best advice is free by definition”
- 43:29Take a 360 review of your life
- 50:16Shaan bombs a talk at a conference (lessons learned)
