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My First MillionHow To Make $25 Million With A Niche Hobbyist Magazine (#419)
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Flying Magazine: turning a niche aviation audience into real estate pre-sales
Shaan describes how Flying Magazine, a legacy aviation publication bought for a high-seven-figure price, has readers who include wealthy private-plane owners. He explains how the brand is being used for “content to commerce,” including a residential aviation community concept that has generated significant pre-sales based on his estimate.
- •Shaan outlines Flying Magazine’s appeal to aviation enthusiasts, including affluent hobbyists with private planes
- •He shares a purchase-price range discussion and notes a source indicating a high-seven-figure deal
- •Shaan describes an aviation housing community concept where residents can live around a runway and keep planes nearby
- •He estimates the project has at least $25M in pre-sales (and says it could be higher), while noting he doesn’t know exact numbers
- •They frame this as a powerful example of using media trust to sell high-ticket products (content to commerce)
Craig Fuller’s FreightWaves background and why the numbers matter
Shaan gives context on the buyer behind Flying Magazine by discussing FreightWaves, a freight-shipping data and SaaS business. The hosts react to FreightWaves publishing unusual financial details and discuss what the disclosed metrics imply about the business.
- •Shaan explains FreightWaves as a price/data business for shipping with a SaaS product called Sonar
- •They discuss FreightWaves releasing a public-style report despite not being a public company
- •Shaan extrapolates reported quarterly revenue to an annualized figure and estimates profitability ranges
- •Sam adds that the business is growing quickly, citing ~70% growth
- •They note the company’s cash position as a sign of financial strength
Country-club-for-planes: how the aviation community concept works
Sam and Shaan clarify the physical model of the aviation community: a neighborhood organized around a landing strip, analogous to homes around a golf course. They discuss why Flying Magazine’s audience is uniquely suited for this product and why the bet felt bold but ultimately worked.
- •Sam describes it as a country club with a runway instead of a golf course
- •They explain the customer appeal: convenient “hub” living for private-plane owners
- •Shaan emphasizes the advantage of having a high-income niche audience
- •Sam shares he’d known about the plan for over a year and initially doubted its feasibility
- •They highlight how pre-selling lots/homes de-risks the development concept
Content-to-commerce playbook (and what a media brand can sell)
The hosts broaden the Flying Magazine story into a general strategy: use content to build trust, then sell products or experiences aligned with the audience. They compare “lame” and “baller” versions of content-to-commerce and debate what their own brand could have done.
- •Shaan points to content-to-commerce as a repeatable model and references watch-media shifting into commerce
- •Sam contrasts selling small consumer items versus selling high-ticket products like real estate
- •They revisit an old conversation about moving beyond ads into community-based real estate concepts
- •Shaan argues people pay to live among like-minded people, not strangers
- •Sam reflects on how increased experience changed his view of what their media “pull” could enable
Risk appetite and execution styles: why Shaan runs toward the scary ideas
Shaan and Sam compare their personalities around uncertainty, risk, and execution. Shaan describes being drawn to ideas that feel intimidating and half-figured-out, while Sam prefers higher certainty before committing and then executing with focus.
- •Shaan says he’s attracted to high-thrill business ideas even when he doesn’t know exactly how to do them
- •Sam explains he wants more certainty that the “puzzle pieces” fit before acting
- •They describe a complementary dynamic: Shaan explores; Sam locks in once convinced
- •Sam says Shaan gets bored once the puzzle is solved
- •They relate the discussion to how founders decide which big bets to pursue
A practical test for media influence: can you get people to show up?
Sam uses a Vancouver meetup example to describe what “pull” looks like in media: getting people to leave their homes and show up somewhere. Shaan connects this to setting better goals for audience building and measuring genuine engagement rather than reach.
- •Sam describes a low-key meetup and how even imperfect organization can still attract paying attendees
- •He argues the real signal is whether people will travel or take action when you ask
- •Shaan discusses his interest in going “harder” on creating content across formats
- •They estimate how many people might show up if Shaan posted a same-day coffee-shop invite
- •They frame action-based engagement as more meaningful than raw follower counts
Finding the real metric that matters (and calling out vanity metrics)
Shaan argues that platforms push large but misleading numbers, so creators and businesses need a truer metric for engagement. Sam shares how The Hustle used replies as a high-signal indicator of reader attention and loyalty.
- •Shaan contrasts reach/vanity metrics with measures that indicate real engagement and affinity
- •He references the “1,000 true fans” idea as a way to think about sustainable creator economics
- •Sam explains The Hustle’s tactic of prompting replies (including deliberate typos and specific questions)
- •They discuss sending stickers and receiving an unexpectedly huge wave of replies
- •Shaan asks what metrics best indicate product love in different types of businesses
How growth can be faked: Substack popups, podcast downloads, and inflated claims
Shaan critiques mechanics that manufacture subscriber growth without genuine intent, using Substack’s recommendation flow as an example. He extends the critique to podcast metrics, arguing that “downloads” and “subscribers” can overstate real listening and that some public claims seem implausible.
- •Shaan describes a Substack flow that can cause users to subscribe to multiple newsletters with minimal intent
- •He compares this to aggressive app growth tactics that pre-check contact lists and encourage accidental sharing
- •They discuss how podcast measurement makes it hard to know whether people actually listened
- •Shaan claims some reported podcast audience numbers don’t match observable signals like rankings and reviews
- •He explains how releasing many episodes can inflate monthly download totals even with a small subscriber base
Parcast: bootstrapped scripted true-crime at scale and a Spotify exit debate
Sam brings up Parcast, a true-crime-focused podcast network built with scripted, voice-acted shows produced at high volume. The hosts discuss the reported acquisition price and earn-out uncertainty, plus why true crime dominates charts.
- •Sam describes Parcast’s focus on true crime and its scripted production model
- •He claims the company was bootstrapped and scaled by producing a very large volume of episodes
- •They discuss Sam’s understanding of the Spotify acquisition value versus Shaan’s article citing a lower confirmed figure
- •Sam mentions an earn-out/retention component and notes Parcast’s Wikipedia reads unusually self-congratulatory
- •They remark on true crime’s popularity and share specific show preferences within the genre
Crumbl Cookies: weekly drops, app-driven distribution, and franchise economics
Sam revisits Shaan’s earlier mention of Crumbl Cookies and shares how large the business appears to have become, driven by weekly menu “drops” and strong social distribution. Shaan discusses both the brilliance and potential fatigue risks of the drop-based model while Sam argues a huge plateau is still valuable.
- •Sam describes Crumbl’s weekly cookie-drop cadence and the app spikes it creates
- •He shares claimed scale indicators: store count growth pace, app review volume, and social followings
- •Sam cites franchise-related numbers, including startup cost and store-level revenue/profit examples he’s seen
- •Shaan compares drop dynamics to other trend waves and warns about consumer fatigue when scarcity fades
- •They discuss how founders’ prior product/viral experience may explain execution strength
A producer’s missed signal: the ‘cringe LinkedIn’ founder story
A third speaker tells a personal story about seeing the Crumbl founder post “cringe” motivational content on LinkedIn before the company’s rise. Shaan and Sam riff on how preconceived assumptions about “cringe” versus sales ability can be wrong.
- •A speaker recounts accepting a LinkedIn connection and seeing repetitive hype-style posts
- •They realize the poster was the Crumbl founder, now positioned for enormous wealth if growth continues
- •Shaan admits the story challenges his assumption that overly cringe behavior predicts failure
- •Sam jokes about founder archetypes and the ability to sell
- •They close the anecdote with the regret lesson of not taking early outreach seriously
Super Bowl to AI: play-calling algorithms, AI refs, and whether accuracy ruins sports drama
Shaan suggests NFL offensive play-calling is an ‘AI problem’ that could be improved by models optimizing expected value from game situations. The conversation expands into AI officiating and judging across sports, with Sam arguing that human imperfection creates drama and entertainment value.
- •Shaan connects standout Super Bowl plays to the idea of AI-assisted play selection under time pressure
- •He predicts systems could ingest situational data to recommend optimal plays, similar to a much better ‘Madden suggestion’
- •They discuss AI refereeing, with an example of tennis line calls as ‘unarguable’ due to tracking
- •Sam argues removing human refs/judges could make sports less entertaining because controversy fuels discussion
- •They debate AI judging in fighting and Sam says he mainly wants official scores revealed between rounds
Underutilized assets as a business framework—and skepticism about grand predictions
Shaan introduces a framework from a tweet: big companies can be built by increasing utilization of idle assets, citing examples like spare rooms and unused car time. They brainstorm candidate assets and debate the practicality of turning specialist talent into liquid, mission-based work, with Sam pushing back on broad ‘future of work’ claims.
- •Shaan frames marketplaces as engines for unlocking underutilized assets, and asks for compelling examples
- •Sam gives an example of a virtual-assistant company positioned around a specific labor pool niche
- •They discuss why some underutilized-asset ideas fail due to operations, safety, quality, or thin economics (including home cooking)
- •Shaan lists examples from the thread: cars (especially with self-driving), structured data, solar energy, and daytime reuse of nightclubs
- •They debate specialist talent and a ‘mission-based’ future of work; Sam argues many people prefer stable routines and dislikes sweeping ‘future of’ narratives
