From: myfirstmillionpod
The speaker emphasizes the importance of “the hustle” as a driving force throughout his career, particularly in navigating and overcoming personal and professional challenges [00:48:00]. He shares his story to illustrate how this commitment to hard work has shaped his life.
Early Life Challenges and the Birth of “Hustle”
The speaker’s understanding of “hustle” began when he found something worth striving for [01:18:00]. His high school goal was to maintain a D+ C- average, the bare minimum to graduate [01:38:00]. He ultimately dropped out at 15 [02:07:00]. This decision was not glorified but a result of difficult circumstances: he had run away from home, his girlfriend was pregnant, and they were living in a trailer park [02:29:00]. Had he the option, he would have finished school [02:35:00].
He then spent three and a half to four years working 45 to 60 hours a week doing something he “hated” [02:56:00]. This period, which he calls a “phase of Arrested Development,” was the most instrumental part of his life [03:09:00]. During this time (ages 16-20), he worked as a dishwasher in a restaurant, facing tough bosses, having a baby at home, living in a trailer park, and barely making ends meet [03:31:00]. Despite the adversity, he became the “best dishwasher that restaurant ever had” [04:12:00]. This was his first realization that the more effort he poured into a job, the more he got back [04:19:00]. He eventually received two promotions, becoming a line cook before leaving for New York City [04:40:00]. This experience taught him the “most fair transaction ever: you put a lot in and you get more out” [05:00:00].
Navigating New York City and Early Career Struggles
Moving to New York City, the speaker had only $800 to his name, no high school diploma, and limited kitchen work experience [05:57:00]. He describes the reality of the “hustle in New York City” as “absolutely miserable” [06:12:00]. His living situation was difficult: sleeping on an upright futon in a tiny bedroom with his 2-year-old, and sharing a hallway bathroom with various residents, which kept him “humble in the most literal way possible” [06:17:00], [06:27:00].
He worked as a bike messenger, a job that barely paid, with his phone bill often exceeding his income [07:01:00], [07:23:00]. His first “real job” in NYC came from collecting police barricades for an artist named Tom Sachs, who paid 10 an hour [08:22:00], was also “super super challenging” [08:17:00]. However, it was here that he observed the intense desire and “hustle” of New Yorkers, realizing that to survive in the city, one must constantly chase their ambitions [08:34:00], [09:00:00].
The Pitfall of “Success” and Rediscovering the Hustle
After achieving significant success, including producing a feature film that won an Independent Spirit Award [21:56:00] and having an HBO show premiere for over $2 million [20:42:00], the speaker describes taking a step back and chilling out [21:10:00], believing he had “made it” [20:50:00]. This period, from 2008 to 2010, became the “most depressing time” in his life [21:31:00]. He made nothing and did nothing, feeling miserable despite his outward achievements [21:35:00], [22:12:00].
This “biggest failure” was “celebrating success” and losing touch with his passion and the “hustle” that defined him [31:36:00], [32:06:00]. He learned that with every success, there should come a “bigger, more ambitious goal” [31:49:00].
This realization led him to pivot and focus on YouTube, which he saw as the “most pure form of hustle” [22:48:00]. It allowed him to work on his craft without external pressures or the politics of traditional media [22:57:00]. This renewed commitment to YouTube, based purely on hustle, led to a career that was “his” [23:44:00].
Career Crossroads and Entrepreneurial Setbacks
In 2013, despite his YouTube success, he faced a major crossroads when invited to MIT for a fellowship [23:51:00]. This meant shutting down his company, moving to Cambridge, and leaving his new and pregnant wife, representing a “gigantic risk” [24:25:00]. He chose to take the risk, reset, and chase what excited him [24:42:00].
This experience led him to start a tech company called “Beam,” a departure from his media career, purely focused on technology [25:10:00]. After a year and a half, Beam was running out of money and not growing fast enough to secure more funding [26:05:00]. Instead of panicking, he made the unconventional decision to take the entire team on vacation to the Dominican Republic [26:31:00]. This seemingly “crazy and stupid” move led to the understanding that their most valuable asset was their team and their shared enthusiasm, which helped them re-evaluate their company’s value proposition [26:45:00]. This renewed spirit ultimately led to the company’s sale to CNN [27:17:00].
Sustaining the Hustle Amidst New Challenges
After the sale to CNN, the speaker finds himself at the “bottom of a mountain that’s probably bigger than any other Mountain I’ve ever looked up at” [27:27:00]. Despite having tremendous resources, a strong team, and public scrutiny, he admits he doesn’t “entirely know how to do it” [27:58:00]. However, he remains confident that the “number one most important ingredient” is “the hustle” [28:01:00].
Personal Sacrifices and Time Management
When asked about balancing his demanding career with family life, the speaker attributes his drive to having a child, stating, “I can do this because I have a kid” [29:09:00]. His family provides the essential reason for his actions [29:19:00].
His pragmatic approach to time management involves strict scheduling: leaving for work after his daughter leaves for school (10 AM), being home before 6 PM, and then working from 8 PM until midnight and from 4 AM until 7 AM [29:46:00]. He achieves this demanding schedule by prioritizing work and family, abstaining from partying, drinking, or socializing, and getting minimal sleep (3-5 hours on most nights, with an 8-hour catch-up periodically) [30:01:00], [30:20:00].
His most cherished content involves his family, serving as a “little portrait of my life” that he can always look back on [30:50:00].