Brutally Honest Advice to My Younger Poorer Self Ep 629



In a candid discussion on entrepreneurship, the speakers, including the host of "the game" podcast and their guest, delve into the raw realities of building a business. They emphasize that the uncertainty of success is what makes entrepreneurship worthwhile, advocating for a relentless work ethic and the willingness to embrace the long haul over immediate rewards. The host, who is also the founder of, shares personal insights on the importance of prioritizing and mastering a few skills due to the finite nature of time. They argue against the culture of instant gratification, highlighting the value of building a solid foundation and reputation over time. The conversation also touches on the psychological aspects of entrepreneurship, such as dealing with envy and hate, and the importance of surrounding oneself with genuine supporters. The speakers conclude by discussing the power of providing value without expectation and the transformative impact of internalizing and acting on one's own advice.

Summary Notes

Embracing Uncertainty in Entrepreneurship

  • Uncertainty is an inherent aspect of entrepreneurship.
  • Entrepreneurship requires a tolerance for not knowing if efforts will yield success.
  • The fear of wasted effort should be reframed as a learning experience.

"The fact that you don't know if it's going to work is exactly what makes it worth doing. It's why entrepreneurship isn't for the faint of heart. You have to embrace uncertainty."

This quote emphasizes that the unpredictable nature of entrepreneurship is what makes it challenging and worthwhile. The speaker suggests that embracing this uncertainty is essential for any entrepreneur.

The Value of Documenting the Entrepreneurial Journey

  • Documenting the journey can provide insights and inspiration for others.
  • The speaker regrets that prominent entrepreneurs like Jeff Bezos, Elon Musk, and Warren Buffett did not document their journeys.
  • The speaker is committed to sharing their own journey to help others.

"I always wish Bezos, Musk, and Buffett had documented their journey, so I'm doing it for the rest of us."

The speaker expresses a wish that influential entrepreneurs had shared their experiences in a documented form and declares an intention to provide this type of insight for the benefit of others.

Persistence and Delayed Gratification

  • Continual effort without immediate reward can lead to success.
  • The speaker advises their younger self on the importance of hard work and persistence.

"You can beat 99% of people simply by continuing to work without needing your immediate reward."

This quote suggests that the ability to work consistently without the need for immediate gratification is a significant competitive advantage.

The Realities of Hard Work

  • Hard work involves stress, doubt, and incomplete tasks.
  • The perception of what constitutes hard work evolves with experience.
  • The process of working hard teaches you your true capabilities.

"But that's what hard feels like. The other great reason for working harder is that the harder you work, the more you realize what you used to think was hard."

The speaker reflects on the nature of hard work and how one's understanding of it changes with experience, indicating that pushing past previous limits reveals greater potential.

Work Ethic and Time: The Dangerous Combo

  • A strong work ethic combined with time is extremely powerful.
  • Realizing the effort required to excel forces prioritization.
  • Greatness requires intense focus and cannot be achieved in many areas simultaneously.

"The most dangerous money making combo in the world, it's work ethic and time."

This quote highlights that the combination of a strong work ethic and the passage of time can lead to significant financial success.

The Importance of Volume of Work

  • Large quantities of work can lead to better outcomes than focusing on perfection from the start.
  • The speaker prefers to invest more time in initial drafts to reduce the need for extensive edits.
  • Confronting the sheer amount of work required can be intimidating.

"I think one of my favorite parables about work is that there was an art class. They split the class into two groups..."

This anecdote illustrates the speaker's point about the value of producing a large volume of work, as it can lead to better quality through practice and iteration.

The Shift from Employment to Entrepreneurship

  • Working for oneself differs from a traditional job because income is tied directly to output.
  • Entrepreneurs must be comfortable with working without immediate financial reward.
  • Delaying gratification can lead to larger outcomes.

"When you start working for yourself, you're not getting paid to be there. You're only getting paid on what you do."

The speaker contrasts the experience of traditional employment with entrepreneurship, emphasizing the direct link between work and financial reward in the latter.

The Entrepreneurial Path and Its Challenges

  • Entrepreneurship is characterized by uncertainty, sleepless nights, and financial worries.
  • The true reward comes from becoming the person you aim to be through your efforts.
  • Rushing and impatience can lead to poor decisions and prevent success.

"Sitting in uncertainty is the feeling of entrepreneurship. You're not doing it wrong. Like, that's what it feels like."

This quote reassures aspiring entrepreneurs that the difficulties they face are normal and part of the entrepreneurial experience.

Building a Reputation Over Time

  • Long-term reputation building is crucial for entrepreneurial success.
  • Speed is often wrongly rewarded in our culture, leading to a focus on quick results.
  • True value creation takes time and is not guaranteed, easy, or fast.

"From a brand foundation perspective, it's, how can I build a reputation over a long period of time..."

This quote discusses the importance of building a long-term reputation rather than seeking immediate transactional success, highlighting the time and effort required to establish a strong brand.

Foundations of Business

  • Discusses the importance of having a strong foundation for creating a successful business, especially for those starting out.
  • Highlights how leverage and foundation can accelerate business growth.
  • Emphasizes the importance of preparing and sharpening one's "axe" in the business world.

"The reason I like service businesses for people who are starting out is that you don't have to do either of those things. But if you had one or two or both of those things, then you can create something bigger, faster on a longer time horizon."

The quote explains why service businesses are recommended for beginners, as they require less foundational work, but also acknowledges that having leverage or a foundation can lead to greater success over time.

Time Horizon and Measuring Success

  • Stresses the need to adjust one's measuring stick when shifting from employee to entrepreneur.
  • Differentiates the paths to reaching various financial milestones and the associated effort.
  • Compares the effort required in different business ventures and their potential returns.

"Your measuring stick has to change when you get into a different game. Sometimes the fastest way to get to a million dollars a year isn't the fastest way to get to $10 million a year."

This quote emphasizes the need for entrepreneurs to adjust their expectations and metrics for success when transitioning from traditional employment to entrepreneurship.

The Entrepreneurial Mindset

  • Entrepreneurship requires embracing uncertainty and the possibility of efforts not leading to success.
  • Discusses how perceived wasted effort can actually contribute to personal growth and prevent burnout.

"What makes entrepreneurship isn't the work itself. It's actually just not knowing if the work will work."

The speaker is highlighting the essence of entrepreneurship, which lies in the uncertainty of outcomes despite the effort invested.

Skills as Income Insurance

  • Advocates for investing in personal skills as a form of income insurance.
  • Skills are considered a reliable asset for generating income, regardless of the currency in use.

"I consider skills income insurance. You just know that you will be able to make money."

The speaker is suggesting that developing skills is a way to ensure one's ability to make money, likening it to an insurance policy against income loss.

Work-Life Balance and Retirement

  • Critiques the modern concept of weekends and advocates for finding work that doesn't necessitate a break.
  • Proposes a long-term perspective on work-life balance and the idea of seasons of work.
  • Argues against traditional retirement, suggesting that continuous work contributes to longevity and purpose.

"What you really need is work that you don't need a weekend from. And instead of thinking about work life balances, like a seven day work week, think about work life balances on a seven year time horizon."

This quote challenges the conventional view of work-life balance and weekends, promoting the idea of finding fulfilling work that aligns with a longer-term vision of life.

Productivity and Weekends

  • Contrasts the traditional use of weekends with the potential for progress if used productively.
  • Explains the potential setbacks from not working on weekends, especially in a business context.
  • Suggests that foregoing weekends can significantly accelerate the achievement of goals.

"You'd be amazed at how much faster you can get to your goals when you don't go back. It's 104 days a year."

The speaker is highlighting the potential gains in productivity and progress towards goals by utilizing weekends effectively, instead of adhering to the norm of taking them off.

Success and Competition

  • Success is framed as the best form of revenge against naysayers and competitors.
  • Describes how expanding one's success diminishes the relevance of detractors.
  • Reflects on the experience of outcompeting others and the lack of satisfaction in their defeat.

"Success is the only revenge. As you expand, they shrink into irrelevance. As you get louder, no one can hear them."

This quote encapsulates the idea that personal success is the most effective way to overshadow critics and competitors, rendering their opinions insignificant.

Competition and Focus

  • Competition can lead to a vicious cycle of erratic behavior and distraction from core goals.
  • A significant financial loss was experienced by the speaker due to being influenced by competition.
  • Winners concentrate on their own goals, while losers concentrate on what the winners are doing.
  • Competitors who focus on copying others miss out on serving their customers effectively.
  • Copying is a form of flattery and indicates that you are leading in your field.
  • There is an abundance of opportunities, and focusing on competition limits the potential to seize them.
  • Adversity and competition can forge a stronger, more capable individual.

The biggest mistake of my career I made because of a competitor. That mistake cost me somewhere in the neighborhood of $25 million, actual money.

The speaker highlights the severe consequences of allowing competition to dictate one's actions, emphasizing the importance of maintaining focus on one's own goals.

Winners focus on winning. Losers focus on winners.

This quote underscores the necessity of concentrating on personal success rather than being preoccupied with competitors.

If you feel like you are the output of your life, at the end of your life, who you are is the thing that is the thing that you became, then competition is good for you.

The speaker reflects on the positive aspects of competition in personal growth and the cultivation of resilience.

Personal Development and Relationships

  • The speaker emphasizes the value of friendships that offer genuine support and encouragement.
  • It's rare to find people who both root for you and make you better, making such friends extremely valuable.
  • The journey of entrepreneurship often begins with support from others who perceive it as a step back, leading to a temporary increase in their relative standing.
  • Success can alienate you from your peers as it highlights their unfulfilled potential and missed opportunities.
  • Fear of hypothetical punishment can prevent people from taking necessary actions to achieve their goals.

My two simple lenses for friendship. Number one, do they genuinely root for you when you win? Number two, do they make you better?

The speaker outlines two critical criteria for identifying true friends, emphasizing the importance of support and personal improvement.

The rare people in your life who root for you to hit your goals are more valuable than the goals themselves.

This quote highlights the profound value of having supportive individuals in one's life, suggesting that their support is more significant than achieving the goals themselves.

Perception of Hate and Envy

  • Hate and envy are seen as forms of feedback rather than personal attacks.
  • Envy is the desire for something someone else has, while jealousy is the fear of losing something you possess.
  • The speaker views hate as a source of information that can be used constructively.
  • Misunderstandings and accusations of copying can arise, but they can be resolved with evidence and a clear understanding of the facts.

Unless someone is ahead of you, take their hate as envy and then disregard.

The speaker advises disregarding negative feedback from those who are not in a position to provide constructive criticism, seeing it as envy instead.

I see hate as feedback. Nothing more, nothing less.

This quote reflects the speaker's perspective on negative criticism, considering it merely as data to be analyzed rather than an emotional burden.

Emotional States and Decision-Making

  • Sadness is linked to a perceived lack of options, causing feelings of hopelessness.
  • Anxiety arises from having many options but no clear priorities, leading to a sense of paralysis.
  • Knowledge and decision-making are the remedies for sadness and anxiety, respectively.

Sadness comes from a lack of options, which is why it feels like hopelessness. Anxiety comes from many options, but a lack of priorities, which is why it feels like paralysis.

The speaker provides insight into the emotional states of sadness and anxiety, attributing them to the availability of options and the clarity of priorities.

Looking everywhere but moving nowhere solves sadness with knowledge and anxiety with a decision.

This quote suggests practical solutions to overcome emotional challenges by acquiring knowledge and making decisive choices.

Emotional Responses to Life Situations

  • Different emotional responses are triggered by different perceptions of situations.
  • Sadness may arise from a perceived lack of options.
  • Anxiety can be caused by having too many options and not knowing which to choose.
  • Disappointment is the result of unmet expectations.
  • Adjusting expectations or reality is a way to handle disappointment.

"With sadness, you don't know to do because you don't know anything to do with anxiety, you don't know which to do. Disappointment is when an expectation was unmet."

This quote explains the different emotional reactions to situations based on our understanding and expectations. Sadness stems from not knowing what to do due to a lack of options, while anxiety comes from having too many options. Disappointment results from expectations not being met.

Coping Strategies for Disappointment

  • Stoicism offers strategies to deal with disappointment, such as imagining worse outcomes or repetitive events.
  • Adjusting expectations preemptively can help avoid disappointment.
  • Buddhist monks focus on internal changes rather than external circumstances to cope with life's challenges.

"The stoic frame for that is that you imagine all the things that could have gone worse. I mean, there's a lot of frames, but that's one of them."

This quote highlights a stoic approach to disappointment, which involves considering worse possible scenarios to mitigate the impact of the current disappointment.

Personal Development and Helping Humanity

  • Wanting to benefit humanity can lead to self-exploitation and potential disappointment.
  • Setting goals that are within one's control can lead to joy and satisfaction.
  • Aligning behavior with the type of person one aspires to be can be rewarding.
  • Self-advice can be powerful if aligned with one's knowledge of what should be done.

"You can shoot big as long as you don't make missing mean that you suck."

This quote emphasizes the importance of aiming for high goals without attaching one's self-worth to the outcome. It suggests that failure should not be equated with personal inadequacy.

Advice from Future Self

  • Consulting one's future self can provide grace and approval.
  • Esteeming the judgment of a future, hopefully improved, version of oneself can guide current decisions.
  • Seeking advice from the future self is seen as a source of valuable insight.

"And me being able to talk to my future version of myself in a dialogue format allows me to get grace from a future version of self and also get approval from a future version of self."

This quote describes a reflective practice where one engages in an internal dialogue with a future version of oneself to gain perspective and approval for current actions.

Fear of Failure and Perception

  • People are often more afraid of others' opinions about their failure than the failure itself.
  • The opinions of those who have not achieved one's desired success should not be overvalued.
  • Trying and potentially failing is preferable to not attempting at all.

"No one's afraid of failing. They're afraid of what other people will think of them when they fail."

This quote suggests that the fear of failure is less about the failure itself and more about the social perception and judgment from others.

Evaluating Advice

  • Advice should be weighed based on the advisor's experience and relevance to one's goals.
  • There are seven levels to consider when evaluating advice, from social media comments to experts who have repeatedly achieved the desired outcome.
  • Trust is more likely placed in those who have not only achieved success themselves but have helped others do the same.

"And so I have made seven levels of how I weigh advice that have served me well..."

This quote outlines a systematic approach to evaluating advice, ranging from least to most reliable sources based on the advisor's experience and success in helping others achieve similar goals.

Providing Value and Building Relationships

  • Offering value without expecting immediate returns can lead to opportunities.
  • Starting by providing services for free allows for skill improvement, testimonials, and potential paid work.
  • Persistence and providing value to many can eventually lead to significant income and job offers.
  • The Free Training Project is an example of starting a service by asking for charitable donations instead of direct payment.

"But what happens is a lot of people will shortchange that. And so I get dms every day of people saying, hey, I want to give you value in exchange for. And it's just, stop, don't tell me what value you want to give me and what you want to trade that value for."

This quote discourages the practice of offering value with immediate expectations of return. Instead, it advocates for genuinely providing value to others, which can lead to opportunities organically.

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