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Second-grade Ninja Turtles drawings: first taste of entrepreneurship and regulation
Tim opens by asking Joe’s first memory of causing trouble. Joe recounts selling Teenage Mutant Ninja Turtles drawings to classmates for $1–$2 until a teacher shut it down after parents noticed kids asking for extra lunch money.
- •Joe discovers classmates will pay for his drawings and starts selling them at school
- •The teacher stops the business after parents trace extra lunch money back to him
- •Joe frames it as early opportunity-spotting and entrepreneurship
- •Joe calls it his first “brush with regulation”
Growing up in suburban Georgia with entrepreneurial parents and customer-first modeling
Joe describes growing up near Atlanta in the Deep South after his New York–area parents moved to Georgia. He credits his parents’ self-employment and their example of going above and beyond for customers—like stocking shelves late at night on business trips—as formative.
- •Joe situates his upbringing geographically around Lawrenceville/Atlanta-area Georgia
- •Both parents worked for themselves, creating a household culture of trying ideas
- •Parents worked in health food distribution, serving large and independent stores
- •Joe observes customer service behaviors, including helping stock shelves late at night
Family sports and the shift to supporting intrinsic interests (violin incident → piano)
Joe describes a childhood centered on sports—especially tennis as a family activity—and parents who supported his interests. He tells the story of being pushed into violin, stopping mid-recital as a small child, and how that led his parents to support what he actually wanted, including piano (which he still plays).
- •Tennis was a family sport with competitions and coaching together
- •Joe recounts quitting a violin recital by putting the instrument down on stage
- •Parents change approach: support Joe’s intrinsic interests
- •Joe gravitates to piano and continues playing into adulthood, including jazz favorites and improvisation
Early hustles: lawn mowing and a self-funded senior T-shirt design run
Tim asks about later entrepreneurial experiences, and Joe describes neighborhood services and a high-school T-shirt venture. He uses early design software to redesign the senior shirt, produces about 300 units, and learns the reality of inventory and selling.
- •Joe starts a lawn mowing and car-washing business using door flyers
- •In high school he redesigns the senior T-shirt using Photoshop/Illustrator
- •He pays to print shirts, ends up with ~300 in inventory, then sells them
- •The design riffs on the Tide logo and he does better than break-even
- •Joe learns how digital designs become physical products and how to sell inventory
Finding RISD: Governor’s Honors, a mentor named Donna, and falling in love with creative challenge
Joe explains how art teachers pushed him toward more art training, including Atlanta College of Art classes. A summer Governor’s Honors Program experience—especially guidance from a teacher named Donna—makes art feel practical and introduces him to the Rhode Island School of Design, where he later attends a pre-college program and commits to going.
- •Joe intensifies art training through specialized classes and figure drawing
- •He is selected for Georgia’s Governor’s Honors Program and studies college-level art
- •A mentor named Donna encourages him and points him toward RISD
- •Joe creates a large painting showcased prominently at the program’s final show
- •Joe attributes his passion largely to the creative environment and peer challenge
Legendary senior prank: hacking the school intercom with a cordless phone
Joe tells an extended story of devising an original senior prank by exploiting how easily the school intercom could be accessed by dialing a code. After sneaking into the office to install a cordless phone base, he broadcasts a loud music mix schoolwide, creating chaos, dancing students, and an investigation that quickly narrows to him and his accomplices.
- •Joe becomes obsessed with outdoing a prior prank involving a plastic horse on the school roof
- •He discovers the intercom can be accessed by dialing a code on the phone system
- •Joe recruits friends (including Mark and Chelsea) to sneak in and install a cordless phone base
- •He prepares a tape mix (including Pink Floyd and Alice Cooper) and calibrates volume at home
- •The prank blasts across campus, staff can’t shut it off quickly, and the administration identifies him
Consequences, negotiations, and the prank’s afterlife: MTV reenactment and “county legends”
After being confronted by administrators and threatened with serious consequences—including scholarships—Joe and Mark accept summer chores instead of charges. The story becomes local legend, and years later Joe pitches the prank to MTV and reenacts it for a show at a rival high school after his school refuses to cooperate.
- •Administrators threaten to report the incident to scholarship/college destinations
- •Joe and Mark agree to manual labor and graduation-related tasks instead of charges
- •A school police officer privately praises it as the best prank he’s seen
- •Joe later contacts an MTV producer and gets the story accepted for reenactment
- •Original school refuses; reenactment happens at a rival school and airs on MTV
High school NBA job: ball boy for the Atlanta Hawks and the Michael Jordan incident
Joe explains his high school job as a ball boy for the Atlanta Hawks, describing the role’s hierarchy and responsibilities. He recounts a high-pressure moment working the Bulls bench when a bumped elbow spills Gatorade into Michael Jordan’s lap, forcing Joe to clean it up mid-timeout while Phil Jackson is yelling.
- •Joe gets the Hawks ball boy job by sending a letter after reading a newspaper article
- •He describes ball boy duties from mopping sweat to assisting trainers and setting up locker rooms
- •He notes the shock of early exposure to professional locker rooms
- •He recounts spilling Gatorade on Michael Jordan due to Dennis Rodman bumping him
- •Joe reflects on learning to function in uncomfortable, high-stress situations
RISD crucible: Gareth Jones’ chess-set project and making 16 full-size chairs by asking for help
Joe describes a notorious RISD 3D design assignment: building a chess set by replicating an artist/designer’s works at scale. He chooses Gerrit Rietveld and decides—despite the professor’s doubt—to create full-size functional chairs, learning woodworking from scratch, securing school funding for materials by proposing benches for a dorm quad, and finally revealing 16 chairs at critique.
- •A professor warns half the class will fail due to the chess-set project’s difficulty
- •Joe chooses Gerrit Rietveld and proposes making full-size chairs instead of 12-inch models
- •He has no prior woodworking experience and learns by consulting the furniture department and upperclassmen
- •Joe pitches dorm leadership to fund materials in exchange for installing benches in the quad
- •The reveal at critique leads the professor to admit Joe proved him wrong, shifting Joe’s sense of what’s possible
Building community like a startup: restarting RISD’s basketball team and creating a campus event
Joe recounts learning RISD had no basketball team and deciding to start one, navigating student government recognition, finding gym space, and scheduling games. He frames it as a startup-like experience—team formation, funding, branding, and marketing—and notes the games became one of the few moments the whole campus gathered together.
- •Joe starts RISD’s first basketball team in decades by recruiting players and getting recognition
- •He secures practice space by renting a private high school gym
- •He cold-calls other schools to schedule games and gets hung up on repeatedly
- •RISD’s first game (vs. Clark University JV) ends in a heavy loss but a milestone win culturally
- •Joe emphasizes the team’s deeper purpose: bringing together students, faculty, and the wider community
- •He shares RISD’s humorous sports naming tradition, including the basketball team name
CritBuns: from “charcoal bun prints” to prototypes, manufacturing scramble, and first company
Joe explains how long critiques ruined students’ pants with charcoal and paint residue, inspiring a portable seat cushion concept called CritBuns. Years later he prototypes it, wins RISD’s design diploma competition, and pulls off a last-minute manufacturing feat to deliver 600 cushions before graduation—then launches CritBuns as his first company and learns sales through rejection and persistence.
- •CritBuns originates from discomfort and stained pants during long critique sessions
- •Joe develops prototypes using casting and foam processes
- •CritBuns wins RISD’s design diploma competition; he must deliver hundreds of units on a tight deadline
- •After many manufacturer rejections, he finds a toolmaker and a Connecticut producer to meet the timeline
- •Joe starts the company after graduation, receives the expensive metal mold, and creates inventory
- •He experiences early sales rejection, uses the SW2 + WC = MO framework, and lands his first small retail order
Selling the story: MoMA goal, global design fairs, Tokyo translation challenge, and TV pitching
Joe describes building sales confidence through small retail wins, then pursuing a stretch goal: getting CritBuns into the Museum of Modern Art design store, which takes two years. He shares lessons from selling in-person at design events, creating a repeatable five-step sales process, adapting the story for Tokyo when language barriers stall sales, and even pitching on a Billy Mays casting session (without making the show).
- •Joe targets the MoMA store as a pinnacle shelf and eventually receives an order after sustained effort
- •He breaks the in-person sales process into five stages, culminating in customers retelling the story
- •He learns the product is “50% foam and 50% story,” watching buyers sell it to others
- •In Tokyo he initially sells zero due to language barriers, then creates Japanese materials and gets help translating
- •He meets notable figures through the product journey, including Billy Mays in a high-pressure pitch setting
From products to platforms: sustainability concerns, Ecolect’s Web 2.0 trap, and moving to San Francisco
Joe explains why he didn’t pursue CritBuns as a massive empire: industrial design training and exposure to landfills heightened concerns about making “more stuff.” He describes building Ecolect—a search/community for sustainable materials—then reflects on Web 2.0 thinking where “revenue wasn’t cool,” leading to a free service and a labor-intensive paid ‘Green Box’ samples product. He also covers his Chronicle Books role and the leap to full-time entrepreneurship.
- •A landfill visit at RISD shapes Joe’s desire to avoid contributing to more waste
- •Joe searches for environmentally considered foam for CritBuns but can’t find viable materials
- •He co-founds Ecolect as a directory/search engine for sustainable materials sourcing
- •Ecolect adopts a free model aligned with Web 2.0 thinking; traffic mattered more than revenue
- •The paid ‘Green Box’ ships physical samples but proves laborious relative to profit
- •Joe works at Chronicle Books (a ‘glorified intern’ fellowship), then quits to focus on Ecolect and CritBuns full-time
Airbed & Breakfast is born: rent hike panic, conference lodging gap, and the first three guests
Joe describes recruiting Brian Chesky to San Francisco as a roommate, then immediately facing a rent increase and financial pressure. Seeing a design conference with sold-out hotels, Joe and Brian host attendees on airbeds with breakfast and local hospitality, solve their marketing problem via design blogs, and discover the surprising value: getting paid to make friends and create a local experience.
- •Joe recruits Brian Chesky to move to San Francisco, then they face a rent hike and lack of cash flow
- •Joe spots a design conference with sold-out hotels and proposes renting out airbeds in their living room
- •They create a simple site (airbedandbreakfast.com) and rely on design blogs for distribution
- •They select three guests who become their first hosts/guests experience and deliver hospitality details (mints, breakfast, maps)
- •Joe emphasizes the difference between hotel isolation and shared local experiences built around food, events, and friendships
From weekend experiment to marketplace: adding Nate, SXSW flop, and DNC breakthrough via press ladder
Joe explains how reactions to the original airbed weekend convinced them there might be something bigger, so they bring in their former roommate Nate as the programmer. The SXSW launch underperforms and exposes a major issue: awkward in-person cash payments and a too-narrow conference focus. They rebuild with online payments and broaden travel use, then use the 2008 Democratic National Convention in Denver as a catalyst, climbing from local bloggers to national/international media and rapidly growing listings.
- •Joe and Brian recruit Nate (a former roommate) to help build a more robust platform
- •SXSW launch results in few hosts and reservations; one reservation is their own
- •A host’s awkward chase for cash payment highlights the need for online transactions
- •They reframe the product as broader travel, add credit card payments, and identify a transaction-fee model
- •They target the Denver DNC housing crunch, pitching local bloggers first to climb to larger outlets
- •Listings in Denver grow rapidly, culminating in national coverage and international follow-on stories
