앤드루 윌킨슨
Co-founder of Tiny; bootstrapped MetaLab, then bought and held small internet businesses
653 records in all
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21 basic records of 141
Episodes are real events from public sources, summarised by us.
Andrew struggled with a messy inbox despite having talented human assistants. He used a tool called Lindy to build an AI automation that triages 80% of his emails and handles logistics like calendar entries and background checks.
LessonCustom AI workflows can outperform human assistants in consistency and speed for specific administrative processes.
Andrew observed many designers spending years at big companies or doing local low-paid work, only to end up drained and starting from zero. He argued that the internet allows anyone with skills to build a high-end agency brand overnight without traditional gatekeepers.
LessonYou don't need permission or a long pedigree to target big clients; you just need a website that showcases expert-level work.
During a ketamine session, Andrew recalled a suppressed memory of bullying his younger brother. This led him to call his brother immediately after the session to apologize for a 30-year-old incident he had been carrying as guilt.
LessonConfronting and resolving long-held guilt can clear mental space and improve personal relationships.
After surviving the recession, Wilkinson became obsessed with financial safety. He started banking cash, learned accounting, and eventually bought or started thirteen more businesses over the next decade.
LessonA near-failure can be a powerful teacher that forces a founder to build a much more robust and diversified business model.
After feeling overwhelmed by the operational details of managing forty companies, Wilkinson stepped down as CEO of Tiny. He promoted Jordan Taub, an experienced operator, to handle the day-to-day management while he focused on vision and acquisitions.
LessonStepping back from roles you hate can revitalize your passion and increase the company's dealflow and opportunities.
Andrew Wilkinson partnered with Ryan Norbauer to build high-end keyboards. He paired Ryan with Caleb Bernabe to handle execution, allowing Ryan to focus entirely on product craftsmanship.
LessonA founder's productivity increases when they are freed from tasks they dislike and paired with a compatible operator.
Andrew worked with a therapist to build the courage to stop being constantly available to energy vampires. He felt heartless at first, but slowly ghosting them caused those draining relationships to fade away.
LessonSetting boundaries might feel cruel initially, but it is necessary to regain mental energy and focus.
Andrew struggled with intense physical anxiety during public speaking despite being confident in small groups. He used beta blockers to dampen his heart rate during speeches, which eventually rewired his brain to stay calm without them.
LessonPhysical symptoms of fear can be managed to allow for the practice of high-stakes skills.
Andrew became a co-owner of a concrete business in British Columbia after his partners found an unsexy, AI-resistant opportunity. The new operators learned the business through manual labor and then systematized the operations.
LessonSuccess in traditional industries comes from combining hard manual learning with modern systematization.
Andrew noticed that billion-dollar valuations were becoming common and that many startups were burning cash without clear paths to profit. He compared the environment to the 1999 dot-com bubble, noting rising rents and high programmer salaries in San Francisco.
LessonMarket euphoria often signals an unsustainable correction, so founders should focus on business fundamentals.
Andrew partnered with a college student to start a simple pressure washing business in Victoria. Despite being a 'boring' industry, it generated over $20,000 in revenue in its first month without any outside funding.
LessonSimple, unsexy businesses that solve obvious needs can be more immediately profitable than complex startups.
After failing at 60% of his ventures, Andrew stopped building from scratch and started buying simple, profitable businesses like Dribbble and AeroPress. He applied his past lessons as filters to build a holding company with over forty companies and hundreds of millions in revenue.
LessonYou don't need a brilliant new idea to succeed; finding and slightly improving existing profitable businesses is a viable path to wealth.
Worried about his children, Andrew consulted a divorced friend who explained that two happy parents living separately is far better than two miserable parents fighting in the same house. This perspective helped him overcome the guilt of splitting up.
LessonChildren are more burdened by a parent's unlived, miserable life than by the logistical changes of a divorce.
After selling Pixel Union for $7 million and seeing it struggle under new management, Andrew bought it back in 2019. He committed $25 million to expand its role in the Shopify ecosystem.
LessonSometimes the best investment is fixing a past mistake by reclaiming a business you understand.
Andrew identified a need for a small business social media agency but waited years for the right partners. He eventually met two impressive students at a university talk and launched 'download' with them.
LessonWait for the right co-founder who has the taste and hunger to operate the business full-time.
Andrew joined a structured peer group through EO where members shared personal and business challenges confidentially. He found the format so effective for navigating life's ups and downs that he eventually started five different forums.
LessonA structured, confidential peer group provides a necessary support system for founders to learn from their mistakes.
When hiring a CEO for AeroPress, Andrew used a recruiter who found Gerard Meyer. Meyer was significantly more experienced than any candidate Andrew had found on his own and was not previously on his radar.
LessonRecruiters provide access to elite talent that founders often miss when searching solo.
Andrew and his partner Zoe used to walk the same route every day with their dog. To expand their sense of time, they started using the AllTrails app to find and visit dozens of new parks in their own neighborhood.
LessonSmall changes in daily habits can significantly increase your sense of novelty and life satisfaction.
Andrew started inviting large groups of his children's friends over to recreate a 'pack' environment. He found that when kids are in a group, they occupy themselves for hours without needing parental intervention.
LessonCreating social groups for children reduces the need for constant parental entertainment.
Andrew studied In-N-Out Burger's history of slow growth, high employee pay, and private ownership. He decided to model his business after their approach of maintaining quality over 67 years without ever taking outside money.
LessonA company can be worth hundreds of millions of dollars while remaining private and sticking to its original values.
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