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Nathan Chan15 August 2022

Nathan Chan: The Founders Blueprint

5Frameworks
11Insights

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Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 1

Hot Take21:30

Entrepreneurship's Highs Are High—and Its Lows Are Low

Nathan rejects the idea that entrepreneurship is uniformly fun. He describes it as difficult and punishing at times, but also uniquely rewarding because founders create things, shape their own work, and make an impact.

  • Enjoyable work does not mean easy work
  • Entrepreneurs will face repeated setbacks
  • Creation and ownership supply much of the reward
  • Nathan's trademark crisis once made him fear bankruptcy

the highs are high and the lows are low and it is tough

Nathan Chan · 22:00

it is the most rewarding incredible experience that i wish everyone to experience in their life

Nathan Chan · 22:00
#entrepreneurship#risk#meaning

Story· 8

Story02:00

Nathan Chan Drifted Through School and Work Before Finding Direction

Nathan describes moving through school, university, and an IT support job without much ambition or excitement. Personal growth work helped him decide he wanted a life he could be proud of and work he genuinely enjoyed.

  • He rarely tried at school and did not achieve strong grades
  • His degree and corporate IT role felt more accidental than chosen
  • Personal growth began before Foundr
  • Direction developed gradually rather than through one sudden mindset shift

throughout life i just kind of drifted

Nathan Chan · 03:00

i wanted to become a person that had a life that i was proud of

Nathan Chan · 03:30
#personal growth#career#purpose
Story08:30

How Men's Work Helped Nathan Clarify His Identity

After reading The Way of the Superior Man, Nathan explored workshops and retreats focused on men's work. He found them confronting but says they gradually gave him more clarity about who he was, who he wanted to be, and where he wanted to go.

  • The book helped him examine purpose and his understanding of male identity
  • He had felt more like a boy than a developed man
  • Workshops were challenging and confronting
  • The benefit was gradual clarity rather than an immediate transformation

it just gave me more clarity around who i am who i want to be and where i want to go in life

Nathan Chan · 10:30
#identity#masculinity#self-development
Story11:30

An Eight-Week Europe Trip Exposed the Cost of the Wrong Career

A long Europe trip gave Nathan a sharp contrast with his IT support job. The dread of returning became the signal that he needed to change direction, prompting further study and a determined attempt to move into marketing.

  • The trip took place in his early twenties with his best friend
  • Returning to work produced an excruciating feeling of dread
  • He did not condemn IT support generally; it simply was not right for him
  • He responded by studying for a master's degree in marketing

there was this extreme dread that i didn't want to go back

Nathan Chan · 12:00

that's when i knew i had to make a change

Nathan Chan · 12:30
#career change#travel#marketing
Story14:00

Repeated Job Rejections Led to the Project That Became Foundr

Nathan invested heavily in a marketing degree but still could not secure internal or external marketing roles. Feedback that he needed a website or project to demonstrate his passion pushed him toward online marketing and a digital magazine side project.

  • Three internal marketing applications failed
  • External marketing interviews also produced no offer
  • One interviewer suggested creating a website or project as evidence
  • The side project combined his technology skills with marketing

it'd be really cool if you had some sort of website or project that you could show how passionate you are about marketing

Nathan Chan · 14:30
#job rejection#portfolio#side project
Story15:00

Foundr Began as a $2,000 Digital Magazine Experiment

Nathan bought digital-magazine software on a credit card while earning about $50,000. The concept shifted from horse racing to entrepreneurship, and interviews with online-business builders convinced him the information deserved a wider audience.

  • The software cost $2,000 on a credit card
  • The first concept was a horse-racing magazine with his housemate
  • When the housemate could not continue, Nathan chose entrepreneurship
  • The magazine launched on March 5, 2013 and made five dollars

i put 2 000 on my credit card and bought the software

Nathan Chan · 15:00

i started interviewing people and that's when i realized i need to share this with the world like this information is gold

Nathan Chan · 16:00
#foundr#side hustle#origin story
Story18:30

A Trademark Lawsuit Forced the Foundr Rebrand

A major US business magazine sued Nathan's young publication for trademark infringement. Help from a former Intrepid colleague enabled a practical resolution: change the name to Foundr, whose unusual spelling later became a distinctive brand asset.

  • The legal threat arrived when the side project was still small
  • An ex-lawyer at Nathan's employer helped him work through it
  • The resolution was a name change rather than abandoning the publication
  • The missing e made the new brand distinctive

was sued for trademark infringement by one of the biggest business magazines in the states

Nathan Chan · 18:30

we just changed the name to founder and that's why it's founded without the e

Nathan Chan · 19:00
#trademark#branding#resilience
Story29:00

Foundr's First Team Was Contractors and Family Favors

Nathan needed specialist help from the first magazine issue because he was not a designer. He combined a paid designer and writers with proofreading from his mother and technical help from his father, then hired his first full-time content employee around early 2015.

  • A designer contributed from issue one
  • Nathan's mother copy-edited and proofread
  • His father helped with technical work
  • Contractors preceded the first full-time hire

i started working with the designer from issue number one and that was critical

Nathan Chan · 29:00

i was calling in all favors

Nathan Chan · 29:30
#hiring#contractors#team building
Story27:30

What Jeff Bezos Wanted After Achieving Extraordinary Wealth

Nathan recounts Scooter Braun asking Jeff Bezos what more he could want when he already had immense monetary success. The reported answer—continued evolution—challenged the common belief that one future financial milestone will make everything complete.

  • Scooter Braun shared the exchange with Nathan's community
  • The question focused on what remains after extreme financial success
  • Bezos reportedly prioritized evolution
  • Nathan connects the story to curiosity and lifelong development

i just want to evolve

Nathan Chan · 28:00

he just wants to learn he just wants to develop he just wants to be curious

Nathan Chan · 28:30
#learning#wealth#growth

Takeaway· 2

Takeaway20:00

Joy and an Audience Commitment Kept Foundr Publishing

Nathan's first interview left him energized despite his nerves and made the work feel deeply right. Subscriptions then added external accountability: readers were owed another edition, so he kept showing up even before the magazine made meaningful money.

  • The first interview was with Lynn from Outsourcing Angel
  • The experience produced unusual energy and conviction
  • Subscribers created a recurring obligation
  • Enjoyment and accountability mattered more than early revenue

after that interview even though i was so nervous i felt so invigorated

Nathan Chan · 20:00

people were subscribed to the magazine and they were owed another magazine edition next month

Nathan Chan · 20:30
#motivation#accountability#consistency
Takeaway31:00

Having the CEO Title Is Not the Same as Doing the CEO Job

Nathan says his development into a true chief executive came well after adopting the title. As Foundr matured, he had to learn accountability, inspiration, and how to lead experienced leaders across a C-suite.

  • Early-stage founders may hold a title without performing a mature CEO role
  • Holding people accountable required development
  • Leading leaders differs from creating a product
  • Experienced executives increased the demands on Nathan's leadership

i have the title ceo but i'm not actually you're not you're not actually really the ceo

Nathan Chan · 31:00

how do you hold people to account

Nathan Chan · 31:30
#ceo#leadership#scaling