25 Years Of Founder WISDOM In 55 Minutes (ft. Jason Fried)

Sam and Jason play Would You Rather… (00:00:00)

• The author prefers a guaranteed 7.5% annual return with no effort over the risk of starting a business or actively investing in the stock market.
• Despite the author's preference for a guaranteed return, 40% of their followers chose the riskier option of starting a business with a $10,000 investment.
• The author believes most people overestimate their ability to beat the market and achieve exceptional returns in the long term.
• Hedge fund offices are often quiet and filled with individuals focused on complex software, unlike the chaotic scenes portrayed in movies like "Wolf of Wall Street."
• Retail investors with limited resources cannot expect to outperform hedge funds and other well-resourced market participants.
• The author expresses disappointment in a company's underperformance despite having 1500 employees and significant assets.
• The author compares the situation to gambling in Las Vegas, where short-term success can lead to a false sense of confidence and eventual losses in the long run.
• The author emphasizes the importance of locking in gains and not expecting short-term market performance to continue indefinitely.

Loosening the grip on the stick (00:05:15)

• Loosening control in business and personal relationships can lead to better outcomes by allowing others to contribute and reducing fatigue.
• Copywriting skills are essential for business success, and a comprehensive document aggregating tips, techniques, and resources on copywriting is recommended.
• Arguing less and listening more can lead to more satisfying interactions, and it's important to stay open to different viewpoints.
• Seeing the Earth from space can provide a life-changing perspective and help people realize the insignificance of many conflicts.

The pale blue dot (00:12:35)

• Carl Sagan's "Pale Blue Dot" passage is described as one of the most beautiful passages about looking back at Earth from space.
• It highlights the insignificance of our worries and concerns compared to the vastness of the universe.
• The passage serves as a reminder that while our daily struggles are real, they may not hold much significance in the grand scheme of things.
• It encourages a perspective of caring by not caring, finding a balance between caring about our immediate concerns while recognizing their relative insignificance.

Why does the businessworld deserve our best lessons? (00:14:03)

• The business world pays for advice from experts in various fields, such as Navy SEALs and sports coaches.
• This is because businesses are insecure and believe that these experts have valuable knowledge to offer.
• Capitalism is here to stay, and business building is the most practical way to manifest a dream or vision.
• Business can be seen as a spiritual journey of turning dreams into reality.
• Sometimes, organizations outside of business seek advice from business leaders, such as Jack Welch's book "Six Sigma."
• It is unclear whether the flow of wisdom is a one-way street from other fields to business or if there is a two-way exchange.

Early days vs. vs. middle days vs later days (00:18:30)

• The early days of a company are exciting due to the unknown possibilities and the burst of new attention.
• Around 15 years in, companies face challenges as they evaluate their future direction and growth potential. Founders may experience an existential crisis during this middle stage, questioning the company's purpose and direction.
• As companies reach a certain size, founders may feel useless or unsure of their role, despite the importance of focus.
• Companies and personal life go through cycles of quiet time and intense activity. Founders may feel depressed during successful periods due to a lack of action.
• After building an organization, founders may feel less valuable as the company can operate without them to some extent.
• Founders transition from the creation phase to the maintenance phase, dealing with internal politics, personalities, hiring, and cultural changes.
• The founder's job is to inject risk into the business, while others manage risk.

A founder's job is to inject risk (00:24:47)

• Taking calculated risks can bring excitement and prevent boredom in business.
• Founders have more freedom to take risks compared to hired executives.
• Building multiple products simultaneously and experimenting with new ideas can create a healthy imbalance.
• Creating fun side projects can provide a dopamine rush and excitement.
• Turning humorous ideas into real problem-solving products can be fulfilling.
• Finding joy in the process of turning ideas into reality is a rewarding experience.
• Witnessing customers genuinely enjoying a product or service is an invigorating and rewarding feeling.

“Cool wears off but useful never does” (00:29:36)

• Useful things are more valuable than cool things.
• Making something useful is one of the most beautiful things one can do for humanity.
• It's important to have fun and not take things too seriously.
• There should be a balance between hard and easy things in life.
• Accomplishing something by oneself can be very rewarding.
• Constraints can lead to creativity and innovation.
• Limitations can force one to think outside the box and come up with new solutions.
• Constraints can help one focus on what's truly important.
• Failure is a natural part of the creative process.
• It's important to learn from one's mistakes and move on.
• Fear of failure can hold one back from achieving their goals.
• Money should not be the primary motivation for starting a business.
• Focus on creating something valuable and useful, and the money will follow.
• Money can't buy happiness or fulfillment.
• Find something you're passionate about and make it your work.
• When you love what you do, it doesn't feel like work.
• Passion can sustain one through the challenges of entrepreneurship.
• The people one surrounds oneself with can have a significant impact on one's success.
• Choose friends and colleagues who are supportive, positive, and inspiring.
• Good people can help one achieve their goals and make the journey more enjoyable.
• Entrepreneurship is a marathon, not a sprint.
• There will be ups and downs along the way, but it's important to keep going.
• Persistence and determination are essential for success.

Striking balance with a business partner (00:31:07)

• Jason Fried and his business partner David Heinemeier Hansson have a harmonious working relationship.
• They don't see each other often outside of work, but they respect and admire each other.
• To ensure a successful partnership, Fried and Hansson had an open and honest conversation about their life values, sacrifices, and goals early on.
• This upfront communication helps them address any issues that arise and maintain a positive working relationship.

The value of talking about money (00:34:14)

• Jason Fried and his co-founder shared their personal finances with each other.
• They were transparent about their financial goals and made decisions based on those goals.
• Fried believes that being open about money is helpful because it provides a roadmap and something to strive for.
• Fried's parents never talked about money, which he found unhelpful.
• Fried is open about money with his own family and friends.

Navigating luxury with kids (00:37:28)

• The speaker struggles with how to talk to his kids about their family's wealth.
• His parents never discussed money or luxury with him, and he doesn't want to make the same mistake.
• He believes that some Midwestern values, such as stoicism and a lack of transparency, can be harmful.
• He wants to be more open with his family and avoid leaving them wanting more when he's gone.
• He has been overly transparent with his family about many things, which he believes lightens things up.

Midwestern values on blast (00:40:08)

• Jason Fried admires David Heinemeier Hansson's honesty about his wealth, such as driving fancy cars.
• Fried struggles with this honesty due to his Midwestern upbringing and the imagined negative messages it might send.
• He acknowledges that most people probably don't care and that it's his problem if they do.
• Fried compares this to people who openly share their political views, which he also finds uncomfortable.
• He believes that sharing one's good fortune and experiences with others is important and that hoarding wealth is wrong.
• Fried shares his approach to wealth with his son, emphasizing hard work and sharing rather than hiding their fortunate circumstances.
• He mentions his property in Wisconsin, which he has renovated and shares with friends and family.

The truth about luck (00:43:39)

• Luck plays a significant role in success, more than people are willing to admit.
• It's important to recognize that luck, such as meeting the right people or being in the right place at the right time, has a substantial impact on outcomes.
• Luck is not just about hard work and skill, but also about external factors beyond one's control.
• It's crucial to convey the significance of luck to the next generation to help them understand that success is not solely determined by effort and intelligence.
• Luck encompasses various aspects, including factors like family background, personal traits, and opportunities that arise due to timing or circumstances.
• The speaker regrets their dismissive attitude towards luck in the past, particularly during a talk at Y Combinator's Startup School.
• They acknowledge that their younger self was arrogant and dismissive of the role of luck in success.
• The speaker emphasizes the importance of self-reflection and personal growth in recognizing and understanding the significance of luck.

Staying up vs. staying off (00:46:55)

• Beware of the trap of feeling like you must know everything right now.
• The constant stream of new information, especially in fields like AI, can create a sense of urgency that is often misplaced.
• Most things don't need to be learned or acted upon immediately.
• It's okay to wait for things to settle down and gain perspective before diving in.
• Jason Fried enjoys reading biographies but finds it challenging to read long books.
• He prefers biographies that are 500 pages or less.
• He reads for an hour every night, which allows him to finish a book in a week.

New insights from old biographies (00:49:45)

• The speaker uses a spreadsheet to create timelines of key events and highlights from business biographies they read.
• They also read archived newspaper articles on newspapers.com to gain insights into past predictions and perspectives.
• The speaker emphasizes that people are often wrong in their predictions and that significant changes can occur within a relatively short time frame.
• They recommend using newspapers.com and following accounts like "pessimists archive" to gain a broader perspective on predictions and historical events.
• The speaker expresses concern about the current trend of people acting as experts and presenting their opinions with certainty, leading to overwhelming information and demands.
• They advise skepticism towards things presented as certain and caution against rushing into adopting new technologies or trends.
• Building on other people's platforms can be risky due to their potential for quick changes.
• Learning from people with different perspectives is valuable.
• The ultimate goal should be to create useful things that benefit others.