Mar 2, 2020 · 1h 32m · how-i-built-this
Video Artist: Casey Neistat
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of How I Built This, digital creator Casey Neistat reflects on his journey from a high school dropout and teenage father to a pioneering filmmaker, viral YouTube icon, and tech entrepreneur. Through candid conversation with Guy Raz, Casey unpacks the pivotal risks, DIY ethics, and relentless hustle that built his personal media empire.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 24.4% of the talking time here. How this is scored →
Guy as informed peer 0.8 Guest teaching 0.9 Guest disagreement 0.7 Guy pushing back 0.6
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:24:00 Calling BS on statistical limitations
Neistat forcefully rejects Raz's deterministic framing that teenage parents or high school dropouts are statistically bound to fail, calling absolute BS on letting societal statistics dictate personal limits.
Hardest push from Guy ▶ 15:40 Pressing on grim teenage parent statisticsRaz refuses to let Neistat gloss over the severe risk of his early circumstances, directly challenging him with the reality that the odds of his life completely falling apart were overwhelmingly high.
Biggest teaching moment ▶ 36:08 Schooled on youthful arrogance over fearWhen Raz assumes Neistat must have felt like an insecure amateur directing Bill Clinton, Neistat firmly educates him on the delusional, supreme arrogance that fueled their early career.
Guy holds their own ▶ 1:13:30 Synthesizing audience monetization with Glossier precedentRaz demonstrates deep domain expertise across entrepreneurial business models by drawing a sharp direct comparison between Neistat leveraging his vlog following and Emily Weiss launching Glossier.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Guy Raz Announces Upcoming Live Tour Dates | 0 | 0 | 0 | 0 | Guy Raz delivers standard promotional announcements for live tour dates and introduces the episode's subject, Casey Neistat. Because this is an intro and monologue segment, host and dynamic scores remain at baseline. | |
| Childhood Hardships and Troublemaking in Groton | 0 | 0 | 1 | 0 | Raz asks open, empathetic questions regarding Neistat's troubled childhood in Groton. Neistat openly shares details about his family's financial distress and his disruptive behavior. | |
| Family Fracture and Running Away at Fifteen | 0 | 0 | 0 | 0 | Raz guides the narrative as Neistat recounts leaving home at 15 following his parents' divorce and moving to Virginia. The exchange is purely biographical and collaborative. | |
| Facing Teen Parenthood and Returning North | 1 | 2 | 2 | 2 | Raz pushes on the objective danger and grim statistics of being a 17-year-old high school dropout father. Neistat acknowledges the statistical truth but reframes how he experienced the situation as having nowhere to go but up. | |
| Life in the Trailer Park Raising Baby Owen | 1 | 1 | 0 | 0 | Neistat describes trailer park living with baby Owen and discovering video editing on his brother Van's iMac. Raz asks about the iMac model colors, which Neistat gently clarifies. | |
| Maxing Credit Cards and Launching Trailer Park Productions | 0 | 2 | 2 | 1 | When Raz characterizes Neistat's early recordings as basic family home archives, Neistat firmly rejects that label, emphasizing that he treated them as serious movies and forced friends to watch them. | |
| Parting Ways with Robin and Moving to New York | 0 | 0 | 0 | 0 | Neistat outlines his decision to split with Robin and relocate to New York City with two duffel bags, taking on artist assistant work. | |
| Experiencing September 11 Near Ground Zero | 0 | 0 | 0 | 0 | Neistat shares a harrowing, vivid firsthand account of biking away from the World Trade Center on September 11, which solidified his resolve to stay in New York. | |
| Directing President Bill Clinton and Gaining Arrogant Confidence | 0 | 2 | 2 | 1 | Raz suggests the brothers must have been terrified of being exposed as amateurs while directing Bill Clinton. Neistat immediately denies ever having that thought, attributing their mindset to youthful arrogance. | |
| Mid-Show Break: Coming Up on How I Built This | 0 | 0 | 0 | 0 | Standard mid-show NPR break and intro to Neistat's first viral campaign protesting Apple's iPod non-replaceable batteries. | |
| Media Frenzy, Commercial Directing, and Chinatown Studio | 2 | 0 | 0 | 0 | Raz showcases familiarity with Andy and Kate Spade, whom he previously interviewed on the show. Neistat details transitioning from artist assistant to full-time commercial directing. | |
| Securing Patronage Financing from Tom Scott | 2 | 2 | 1 | 0 | Raz recognizes Tom Scott as the founder of Nantucket Nectars. When Raz suggests Neistat offered to make videos for Scott, Neistat clarifies they only promised to make videos in general under general patronage. | |
| Packaging The Neistat Brothers as Proto-Vlogging | 1 | 2 | 2 | 0 | When Raz attempts to jump ahead to the HBO sale and asks about early online viewership, Neistat corrects him, noting that online distribution barely existed and that Raz is getting ahead in the timeline. | |
| Selling The Neistat Brothers to HBO for Two Million Dollars | 0 | 1 | 0 | 2 | Raz presses Neistat on why the brotherly creative partnership dissolved immediately after securing the massive $2 million HBO deal. Neistat reflects on how sudden success magnifies partnership friction. | |
| Starting Solo: Casey Neistat LLC and YouTube Launch | 1 | 0 | 0 | 0 | Neistat details starting over solo under Casey Neistat LLC and posting his viral bike lanes video. Raz observes that the ticketing NYPD officer was surprisingly courteous on camera. | |
| Monetizing Commercials to Reinvest in Passion Projects | 2 | 0 | 0 | 0 | Raz and Neistat discuss the business engine of using commercial directing fees to finance passion videos, touching on the inception of Nike's FuelBand campaign. | |
| Make It Count Phenomenon and Industry Acclaim | 1 | 0 | 0 | 0 | Neistat describes the grueling 10-day trip around the world for Make It Count and its massive cultural and career impact. Raz provides accurate background context on view counts. | |
| Public Persona, Multi-Faceted Identity, and Online Criticism | 0 | 1 | 1 | 2 | Raz asks whether the sunglasses-wearing online persona makes people perceive him as an aggressive 'bro'. Neistat explains that each video merely highlights a different facet of his personality. | |
| Pitching Beme and Raising Angel Funding at MIT | 3 | 0 | 0 | 0 | Raz connects Neistat's app venture to Emily Weiss's launch of Glossier from her blog audience, demonstrating strong business synthesis. Neistat explains how MIT Media Lab led to Beme and daily vlogging. | |
| Leveraging Imposter Syndrome and Synergies of Daily Content | 1 | 1 | 0 | 1 | Raz defends Neistat against critics who claimed the daily vlog was purely marketing, framing it as valid strategy. Neistat candidly discusses imposter syndrome and relying on his co-founder Matt Hackett. | |
| Launching Beme, Battling Competition, and Founder Anxiety | 1 | 2 | 0 | 2 | Raz asks why Neistat sold Beme to CNN for $25 million rather than holding out to scale it to a billion. Neistat explains his limits as an executive and compares himself to the pusher on a bobsled team. | |
| CNN Shuts Down Beme and Casey Secures His Family's Future | 1 | 3 | 4 | 3 | Raz repeatedly emphasizes that statistical odds were heavily against a 17-year-old father achieving this level of success. Neistat passionately pushes back and 'calls BS' on living by negative statistics or educational limitations. | |
| Acknowledging Privilege, Luck, and Repaying the Debt | 1 | 2 | 1 | 0 | When Raz asks him to weigh hard work versus luck, Neistat emphatically credits 99% luck and societal privilege, framing hard work simply as cashing in a winning lottery ticket. | |
| How You Built That: Pat Early and the Dripsy Sink Strainer | 1 | 0 | 0 | 0 | In the 'How You Built That' segment, Raz interviews inventor Pat Early about creating the Dripsy anti-clog sink strainer on his homestead. |
Statements from this episode (40)
Childhood friends' parents explicitly called Casey Neistat a 'loser'
“The thing that stands out the most now, when I look back on it, are the parents of my friends. I remember them, you know, calling me a loser, like literally using that word.”
Casey Neistat left his parents' home at 15 and never returned
“I was 15 years old. It was a Tuesday night. And a school night, and it was cold, and, ah, I left. I walked, I took a backpack, and I left my parents' house, and never went back.”
Neistat: Restaurants will always hire kids under the table for dishwashing
“Anywhere there's restaurants, there's a, somebody willing to hire a kid for eight or 10 bucks under the table to wash dishes, and I knew that would happen, and that's exactly what we did.”
Neistat earned $8 an hour as a teen father without family support
“My parents didn't, you know, step in with money or anything, not that they had anything to step in with. You know, Robin didn't really have any parents, so we didn't have anyone to turn to. We were all on our own. And, you know, I was making eight dollars an h…”
Neistat bought a $12,000 trailer with an $800 down payment as a teen
“The trailer, I think, was 12,000 dollars, and I put, I think, eight or 900 dollars down, and then got a mortgage for the rest that my grandmother co-signed for, and then we had to rent a little piece of land that we parked it on, and we lived there”
Neistat: Apple iMac was the first consumer computer for video editing
“He bought an iMac computer, which was the first kind of the first consumer market computer that you could edit video on.”
Neistat financed his first editing Mac with two $400-limit credit cards
“I applied for a credit card so I could buy that machine, and I was only able to get a credit card with a 400 dollar limit. So I got another credit card that also had a 400 dollar limit up to 800 bucks for keeping track And that, in combination with my tax retu…”
Neistat's first editing computer had a 10GB drive holding 12 minutes
“Yeah, it was shooting to tape, and moreover, the machine only had a 10 gigabyte hard drive, which held about 12 minutes of video, so I would edit one video at a time, and I remember I would back up my footage to VHS tapes, because VHS tapes were pretty cheap.”
Neistat moved to NYC on a $1,500 loan to sleep on a couch
“She put up the, like, 1500 dollars for three months to be on this couch, and it was a, like, a 250 square foot studio apartment in the East Village that had been Walls had been put up to make it a two bedroom.”
Neistat: Gained early NYC stability moving into an SRO unit
“And one of those people was, you know, like a friend of a friend, and he had lived in this, something called an SRO, a single room occupancy. And it's where you sort of, you get a room, but you don't get a bathroom or a kitchen. And it wasn't much of an apartm…”
The Neistat brothers charged $5,000 for their first birthday video gig
“We were like, did we charge him a hundred dollars, or 500 dollars, and ultimately we landed on 5000 dollars. Like, we're going to swing the fences here.”
Neistat's first paid filmmaking gig featured former President Bill Clinton
“And that was the first real paid gig we ever had.”
Neistat: Apple refused to replace iPod batteries under official 2003 policy
“The other end of the phone explained to me that Apple as a policy does not replace the batteries in their iPods”
Neistat's 2003 'iPod's Dirty Secret' video crashed its host site within 24 hours
“Within 24 hours, it was everywhere to the point where the site was crashing but it did millions and millions of views in the days when to go viral required actually emailing somebody the video.”
Neistat Quit His Job After Securing a $10,000 Commercial Directing Deal
“What it literally was a candy bar company wanted to test their candy bar Marketing in a very tiny market, and they had 10,000 dollars as an all-in budget, and the minute they greenlit that, and we got the money I quit my job.”
Casey Neistat: Tom Scott agreed to finance Neistat brothers' studio overhead
“And we shook hands, and he agreed to finance us, and we walked out of there. It was the hugest deal we could have ever imagined.”
Neistat used his first studio funding for overhead, not new gear
“We didn't spend it on gear. I don't know that we would have known what to buy. We're still using iMovie”
Casey Neistat: The Neistat Brothers was a YouTube vlog before vlogging existed
“I mean, it was effectively a YouTube vlog. It was a YouTube vlog before the words YouTube vlog existed. It was sort of accessing someone's life in a way that I don't think people had seen before.”
Neistat's HBO series was shot on a $200 camera and cut in iMovie
“We shot this video on a 200 dollar camera we bought at Walmart. We edited this in iMovie”
Neistat: HBO Programming Head Left Days After Acquiring Series
“The head of programming at HBO left the company in the days after she bought our show.”
Neistat: Creative Partnerships Are Harder to Navigate After Achieving Success
“When you have a partner, you have someone to blame all of the failures on, and someone to attribute all of the successes to. And when you are, when you combine that understanding with having nothing, it works, because you're in this together. But when you comb…”
Neistat: Maintained years-long friendship with NYPD officer who ticketed him
“I maintained a friendship with that officer for years after that. Years. He loved the video.”
Neistat: 'Bike Lanes' exploded faster than iPod video due to social media maturity
“Not since the iPod movie had I seen a kind of reaction. It was everywhere, and the difference now is that social media was just really starting to pick up and I shared it as best I could, but it, Didn't need that. I don't know who picked it up, but it just exp…”
Neistat: Commercial directing revenue funded early independent YouTube videos
“Out of that, I built sort of what was my first business post Neistat Brothers, post working with my brother. And what that business was making videos on YouTube that would garner enough attention and enough interest from the industry that would then offer me j…”
Nike gave Neistat an $80,000 budget for the 'Make It Count' commercial
“Which I've never really disclosed this before, but This seems like a great place to say, Guy, I think our budget was around 80,000 dollars to make this commercial.”
Neistat: Make It Count Defined Every Commercial Job Through 2015
“Every job opportunity I had for the next several years was companies from all walks of life coming to me being like, hey, can you do for us what you did for Nike? And I mean it, and that defined my career until about 2014, 1015. It was the only, every job I ha…”
Casey Neistat isolates specific authentic personality facets for different videos
“I think that I'm just very comfortable with picking a part of me and making the video about that part of me.”
Neistat: Casey Neistat LLC generated hundreds of thousands of dollars annually
“I mean, I was making, you know, I was making hundreds of thousands of dollars a year. This was more money than I made even post HBO. It was a legitimate business.”
Neistat: MIT professor Sep Kamvar offered $100k as Beme's first investor
“He goes, I'd like to be your first investor. You can put me down for a 100,000 dollars.”
Neistat: Beme raised just under $500k in initial angel funding
“And ultimately I raised just under a half a million bucks.”
Neistat started daily vlogging solely to build an audience for Beme
“I thought, you know, I need to really go hard on YouTube to get my audience engaged so when I tell them about this product that they'll, they'll be there for me. And I came up with this idea then to make a video every day, and every day share sort of a story f…”
Daily vlogging boosted Neistat's subscriber growth to 10K-20K per night
“My YouTube channel that took me, you know, six years, seven years at the time to get from zero subscribers to 400 Thousand subscribers. All of a sudden, every night I'd wake up and there'd be 10,020 thousand new subscribers.”
Neistat: Knowing the reality of startups would have scared me off entirely
“If I knew then what I know now about what it means to start a tech company, I wouldn't have Not only not done it, I would have run as far away from that idea as I possibly could have. It was not knowing, and this has been true my entire career, you know, my en…”
Neistat: Beme's marketing and idea always outshined its actual product
“I think that the idea and the marketing were always better than the product that we were able to build.”
Neistat admits Snapchat Stories executed Beme's vision far better than Beme did
“To be honest with you, I was a huge fan of Snapchat stories, and the more I used it, the more I realized they did what I wanted to do, but they just did it way better.”
Neistat: Baseline Financial Security Ended My Motivation for Money
“The reality is the moment in my career that I got to a place where I didn't have to worry about paying for food or covering rent, I stopped really being motivated by money.”
Neistat considers himself excellent at initial project launches, not long-term execution
“I'm really good at being the second man in a bobsled team, which means I get really excited, and I can push really, really, really hard, but the second it launches out of the gates, I just sort of jump in, and I'm like, okay, what now?”
Casey Neistat: CNN shut Beme down due to lack of rapid growth
“If you look at a company like that, and this is my understanding, if you look at a company like that, they need to see real growth. They need to see a real trajectory for success, and they need to see it fast, and I think that, I don't think we were able to de…”
Neistat: Beme acquisition financially secured his family's future
“Probably. Yeah, I think that if we didn't live in New York City or Los Angeles, that, that'd probably be the case. I can tell you that in the terms that I think of, which is, can I now give my children the lifestyle that I've always wanted to give them? The an…”
Neistat: Privilege is a winning lottery ticket; hard work cashes it in
“I was born with a winning lotto ticket in my hand. All I had to do was cash it in. And that cashing it in is hard work. Like, that's what that meant. To cash it in was hard work. And I did my part. But I could have never done my part without first winning the …”