Self Help

Burn the Boats - Matt Higgins

Author Photo

Matheus Puppe

· 38 min read

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  • The quote summarizes the experience of the Jets American football team, who were energized and unable to sleep after a coach quoted Sun Tzu’s saying about “burning the boats” to motivate them. This contributed to an important win for the team that season.

  • The author saw this philosophy of “no turning back” as guiding his own decisions and believes it has stuck with him ever since. He grew up in poverty without hope and was determined to forge his own path rather than accept the options seemingly available to kids from his neighborhood.

  • He discusses how he realized as a young teen that the traditional high school path would not work for him, so he hatched a plan to drop out at 16 and get his GED in order to fast-track to college and better opportunities. He intentionally failed classes to fully commit to this unconventional route, dealing with doubters along the way.

  • The author credits his understanding from a young age that he had to make his own way without relying on others or waiting for help. This philosophy of self-reliance has continued to guide him in business and in identifying other successful people.

  • The author recounts dropping out of high school due to feeling unchallenged and unfulfilled. They passed the GED exam and got accepted to college while working various political jobs.

  • As they started writing this book, the author reflected on whether “burning the boats” (taking dramatic action like dropping out of school) is always the right strategy or just worked for them given their privileges.

  • The book aims to share stories of entrepreneurs from all backgrounds to show that reaching your potential requires acting on your visions, no matter where you start from.

  • Core principles discussed include having a clear vision or dream as a starting point, even if others doubt it. Examples profiled had visions like changing the hair industry to celebrate Black women, creating Airbnb, and developing New York’s Hudson Yards.

  • Acting on intrinsic motivations borne from personal experiences provides the most valuable inspiration for pursuing ambitious goals, despite doubters or conventional wisdom. Having permission to see and act on one’s visions unlocks potential.

In summary, the passage reflects on the author’s unconventional education path, emphasizes acting on internal visions and instincts over external doubts, and aims to showcase diverse entrepreneurs who did so to achieve extraordinary success.

The passage discusses the importance of having a clear vision or purpose that drives one’s life and work. It provides examples of entrepreneurs who succeeded by trusting their instincts and visions, even when data or conventional wisdom suggested otherwise.

Abhi saw potential in recovering discarded apples and turning them into a business. The author questions whether the reader has similar clarity about their own vision.

Stuart Landesberg envisioned creating sustainable household products but was rejected 175 times by investors. He trusted his vision and found one investor who also believed, leading to great success with Grove Collaborative.

The author says leaders make “gut sandwich” decisions based more on intuition than data alone. Examples are given of Jobs, Lake, and Bezos envisioning new possibilities that others couldn’t see, not based on existing data but on their visions.

Jordana Kier and Alex Friedman started LOLA feminine products because they intuited women wanted clearer ingredients and options, despite data showing an entrenched market. By talking to women, they validated their instincts and built a successful business.

In summary, the passage encourages having a clear sense of purpose and trusting one’s vision, as data alone does not capture game-changing ideas that successful entrepreneurs and leaders pursued through intuition and conviction.

  • Data and research can lead people to second-guess themselves and give up before even trying something new. Don’t let numbers hold you back if your gut tells you something is right.

  • Following your instincts gives you peace of mind about decisions rather than second-guessing based on data. Winners like founders of successful companies trust their instincts.

  • Continued success requires ongoing risk-taking and successive choices, not standing still after an initial win. Examples given are Kevin O’Leary and Lori Greiner diversifying and growing their empires.

  • The author took career risks like quitting jobs, moves that paid off by opening new opportunities. Trusting instincts and taking leaps allows one to escape constraints and rise above past limitations.

  • Jason Feldman’s career path of industry jumps gave him experience and flexibility to pivot his company during COVID to rapid testing, following his entrepreneurial instincts.

  • Following opportunities builds a diverse skillset unlike those climbing the “corporate ladder.” Trusting one’s varied experiences serves well in disruptive times.

So in summary, the passage argues successful people trust their instincts over excessive reliance on data, and take career risks through continual learning that allows adaptation to changing environments.

This passage summarizes that while the author felt he had overcome childhood traumas through professional success as an executive for the New York Jets, he later faced a cancer diagnosis that unearthed lingering insecurities. Despite treatment, he returned to work quickly out of shame and fear of appearing weak. While thinking he was demonstrating toughness, he now sees it as covering up his own weaknesses. The experience showed him that inner demons can persist even when outwardly thriving, and true healing requires facing—not masking—one’s struggles.

  • The passage discusses dealing with criticism and skepticism when pursuing new ideas or visions. It cites examples like Dave Chang serving the Impossible Burger and investing in drone racing when others said the ideas wouldn’t work.

  • It argues that as creators pursuing progress, we have to ignore negativity and pursue our ambitions regardless of what others say. There will always be “destroyers” trying to tear down whatever rises. However, critics can provide useful feedback to refine thinking.

  • The key is having faith in yourself and the vision, even without guarantees of success. Creators are destined to win in the end through progress, though it’s not easy to overcome naysayers. View critics as a test of resolve and source of data on potential rejection, rather than personal attacks.

  • If one can defend an idea’s merits when questioned, it has merit. Critics prove there is always an audience for new ideas by showing resistance that must be overcome. The passage encourages steeling oneself against doubts to pursue unlimited future success.

  • Phá—or the possibility of increased reward—is a driving factor in risk-taking behavior. People are more willing to take risks if they see an opportunity to gain an advantage by moving first before others recognize the potential.

  • Haters criticize others because they are unhappy with themselves. While criticism can sting, it often comes from a place of darkness within the hater rather than reflecting real issues with the target.

  • Common motivations for those who try to derail or criticize others include: lack of full context/understanding, envy of others’ success, discomfort with change, and fear that others’ boldness will expose their own weaknesses.

  • People may criticize due to missing key information and perspective. They also may act out of envy if reminded of their own unfulfilled ambitions. Others resist change because it is uncomfortable or threatens the status quo they prefer. Finally, some aim to preemptively cut down those who shine too brightly and make them feel inadequate by comparison.

  • In risk-taking and pursuing new ideas, one has to accept that not everyone will understand due to these human tendencies, and the vision may be misunderstood initially but let history be the judge over the long run. Moving boldly ahead despite critics is often needed to drive progress.

  • The passages describe examples of people trying to tear others down and criticize their goals and dreams. This can create hostile environments where mediocrity is the norm.

  • However, how we handle criticism is what really matters. One key is using positive self-talk, even referring to oneself in the third person (e.g. “Matt, you belong here”). Research shows this can minimize stress and boost confidence. Writing about your values also helps.

  • It’s important to surround oneself with supportive people in the early stages of new ventures, as criticism can zap momentum. Even small support from others can hugely lift performance.

  • One shouldn’t feel held back by past flaws or struggles - those can become strengths with the right reframing. The story of Rex Ryan is given, where publicly revealing videos caused shame but he reframed it positively. One’s deepest flaws can be turned into astonishing triumphs.

  • Great leaders need to show their humanity and have a sense of humor. Rex Ryan talks about owning his flaws and mistakes instead of hiding them.

  • Dave Chang was open about struggling with bipolar disorder, which helped others by showing mental health issues are common and success is possible despite struggles.

  • Isaac Wright went to jail for trespassing while photographing from heights but his art gained fame after, raising $6.8M for charity. His tough experiences fueled his success by expanding his thinking on what’s possible.

  • The author shares his difficult background with students to inspire them, showing past struggles don’t define future success which is possible through grit and perseverance.

  • Successful people absorb wins into their identity but reflect on losses to learn from mistakes without letting failures stunt their growth. Michael Rubin and Dave Chang discuss not hiding from failures but using them as learning experiences to improve and achieve bigger wins.

  • The article discusses process failure in four stages: acknowledging the failure, separating your identity from the failure, learning from what caused the failure, and committing to do better next time.

  • It also discusses overcoming loss aversion by focusing more on potential gains than avoiding losses. High achievers are able to take risks and learn from failures.

  • A key lesson is promoting empathy, both for yourself and others. The author discusses how personal struggles shaped his views on fostering an understanding culture at work. People need space to bring their whole selves without fear.

  • Other ideas discussed include confronting your mortality to overcome fear and live purposefully. The present is all we have, so we shouldn’t waste our one life. Accepting an inevitable end can paradoxically make us bolder.

The overall message is about normalizing failure, focusing on growth opportunities it provides, having empathy and understanding towards yourself and others, and using awareness of mortality to confront fears and take bold risks and leaps forward in life.

The passage discusses Jesse Derris, a talented young public relations professional, and his decision to leave his successful career at a big PR firm to start his own agency. His mentor convinced him it was the right career move by emphasizing that depending on others for his success meant there was more risk and less control over his own fate.

Jesse was afraid to make the leap, but his girlfriend supported him. He left with $2 million in funding and started Derris & Company. It was a big success, growing to 80 employees and becoming a top agency. Several of its clients became billion dollar companies. Derris was eventually acquired by a large PR firm, making Jesse a millionaire many times over due to taking the risk.

The passage argues it’s riskier not to take chances and pursue your dreams. Waiting for perfect conditions means obligations grow and it’s harder to leave a stable career. Following conventional wisdom of staying put limits your potential. The story of marketing firm Gin Lane burning its boats and transitioning to create its own brands rather than just develop campaigns for others is presented as another example of breaking the mold and going against conventional wisdom to find new challenges and meaning in work.

  • Emmett and his co-founders Nick and Suze launched Pattern as a company to own and run their own brands in the home goods space.

  • Their first brand was Equal Parts cookware, designed to help people enjoy cooking more. They then launched other brands like Open Spaces (home storage) and acquired existing brands like GIR (kitchen tools) and Letterfolk (home decor).

  • Building brands from scratch was harder than expected with challenges in product development and supply chains. They realized taking over existing brands may have been a better approach.

  • Armed with this knowledge, they raised $6M in funding to acquire more established brands doing $2-10M in annual sales, rather than starting completely from scratch.

  • Launching Pattern was not as easy as planned, but through learning and adapting their model, Emmett is proud of what they’ve built and feels they are listening and evolving based on what’s working rather than sticking rigidly to their original plans.

This passage discusses how proprietary insights can lead to breakthrough business opportunities, even if others don’t initially see the potential. Some key points:

  • Sarah Cooper may one day leverage her skills in a new TV show, showing how skills gained from past experiences can be useful later on in new ways.

  • The Magic Spoon founders pivoted from crickets to cereal based on their own instincts, despite experts saying the cereal aisle was stagnant. This paid off with significant success and funding.

  • Joseph Bayen started companies like Lenny Credit and Grow Credit based on his insight that underserved groups struggle to build credit scores, despite initial challenges finding partners. This led to over $100 million in funding.

  • Michelle Cordeiro Grant recognized women felt underserved by lingerie retailers and started Lively focused on community, selling it for $100 million despite early skepticism about her approach.

  • Marc Lore identified the untapped potential of online diaper sales based on his own search patterns and knowledge, building and selling it for over $500 million, showing proprietary insights don’t require unique inventions.

The key message is opportunities are only opportunities until others see them - one should act on their own instincts and proprietary insights rather than waiting for validation, as that’s when the biggest success stories are created. Gained skills and experiences are also valuable assets that can be leveraged in new ways later.

This passage discusses committing fully to pursuing one’s dreams and goals without fallback plans. Some key points:

  • Having backup plans or only partially committing reduces motivation and the likelihood of success. It’s better to go “all in” on one goal rather than hedging with alternatives.

  • Fantasies and ideas that keep you up at night should be taken seriously as signals to pursue new opportunities. Don’t dismiss internal urges to change paths.

  • The author quit his stable, long-term job without a concrete new plan but saw it as necessary to fully commit to exploring new opportunities. This paid off when he was offered an interesting new role.

  • Going all in doesn’t mean taking reckless risks without protections, but it does mean directing full energy to one goal rather than diversifying too much across multiple plans.

  • Uncertainty is uncomfortable but pursuing dreams fully despite doubts is important. Having conviction in an idea outweighs the need for too much diversification of efforts.

So in summary, the passage advocates committing single-mindedly to goals and dreams, without backup plans, in order to increase motivation and the chances of success versus a half-hearted approach.

  • The passage discusses an entrepreneur named Per who raised $75 million on his own less than a month after ending a SPAC partnership with the author.

  • The author acknowledges this partnership did not work out, but says taking risks is important even if they don’t always pay off. The risks never taken are the ones that will surely lead nowhere.

  • The experience of failure will lead to something greater next time if the lessons are learned.

  • Success is not guaranteed and with every pursuit something will be lost or sacrificed. But the possible rewards make it worth it.

  • Focus more on your “why” or motivation than the exact “how”. View each challenge as part of a larger journey and don’t define yourself by any single outcome.

In summary, the author reflects on a business partnership that failed but sees the value in taking risks despite unknown outcomes. Failure in this case provides an opportunity for growth towards future success.

  • The author wanted to teach a course at Harvard Business School on the direct-to-consumer (DTC) space, having extensive experience investing in and working with DTC companies.

  • After months of conversations, he was allowed to propose a course for a intensive short term. He proposed a topic on the contemporary and underexplored DTC space, where he was an undisputed expert.

  • The planned four day course had almost two dozen DTC founders coming to speak with students. The author spent huge amounts of time preparing for each session.

  • The course included candid discussions with founders like Lori Greiner and Gary Vaynerchuk. It aimed to give students an immersive experience of the DTC industry.

  • The course was extremely popular and successful. It provided insights students would not otherwise get. The author is now a co-teacher of the annual course at HBS.

  • The author embraced his anxiety over teaching and gave his full effort despite fears. This allowed the course to be meaningful and impactful for students.

  • The passage discusses how holding onto ideas too long without properly assessing their feasibility can lead entrepreneurs astray.

  • The author launched an idea for an app called Leap Seats that would allow fans to move to better seats in stadiums if empty seats opened up. He recruited an experienced CEO but failed to consider if it was really a standalone business idea or just a feature.

  • As digital ticketing became more common, the author realized Leap Seats would be better as a feature than its own app/business. He ended up shutting it down to avoid prolonging an unviable idea.

  • This experience taught the author about the fine line between confidence and delusion in entrepreneurship. It’s important to be self-aware of limitations and constantly evaluate ideas based on market realities. Admitting when an idea won’t work is better than persisting delusionally.

So in summary, the passage cautions entrepreneurs against getting too attached to ideas and stresses the importance of realistic assessment to recognize when it’s time to pivot or shut something down before wasting more resources.

  • When anxiety moves from being optimal and driving you to succeed, to “derailing anxiety” that can sabotage your dreams and performance.

  • The author struggled with anxiety, insomnia, and obsessive worrying his whole life. Sometimes it helped but sometimes it paralyzed him and put his success at risk.

  • He experienced acute anxiety before his first appearance on Shark Tank, worrying he would embarrass himself in front of millions. Despite preparing physically and mentally, he had a sleepless night in his hotel room before the show.

  • On the show, he froze at first but took a deep breath and decided to trust himself. He ended up competing with Kevin O’Leary for a deal and securing it, proving he belonged there.

  • The author recommends finding studies to reassure yourself when anxious, meditating daily to boost resilience and focus, acknowledging negative thoughts but not dwelling on them, and doing relaxing activities like exercise to manage anxiety levels. The goal is to prevent anxiety from reaching debilitating levels like he experienced before Shark Tank.

Here are the key points from the passage:

  • The long term success comes from starting small habits consistently over time, rather than big changes. Focus on daily routines like meditation, exercise, work hours, etc.

  • Not everything needs to be a strict routine. Flexibility is also important for creativity. Find the right balance that works for you.

  • Don’t be too hard on yourself for not achieving perfection. Keep trying and forgiving yourself as you work on developing better habits.

  • The main message is that small, consistent actions done regularly over the long run are more effective than irregular bursts of big changes or striving for perfection immediately. Persistence and forgiveness are important principles.

  • The passage talks about embracing crises as opportunities rather than just dealing with them. It discusses how focusing on the positive during crises can build long-term resilience.

  • It emphasizes showing up and persisting during difficult times. Examples given are how Rudy Giuliani visibly led New York City after 9/11 and how &pizza’s CEO Michael Lastoria strongly supported employees through the Covid pandemic.

  • Facing crises head on and working backward from the worst case scenario is presented as an effective crisis management approach. This allows you to limit choices, focus on priorities, and take bold action like &pizza did with raising wages.

  • The ability to iterate and pivot strategically even in the absence of an immediate crisis is recommended. This harnessing of clarity without needing total devastation around you.

So in summary, the passage promotes positively reframing crises as opportunities, showing up and persisting through challenges, considering worst cases to focus responses, and proactively adopting crisis-driven mindsets for improved long-term resilience and viability. Leading examples discussed are Rudy Giuliani after 9/11 and &pizza’s Covid employee support.

The passage provides guidance on how to respond effectively to crises and challenges in business. It emphasizes thinking creatively about new opportunities that may arise, rather than just trying to mitigate losses or get back to the previous status quo.

When facing difficulties, it’s important to ask yourself how you would start the business from scratch today. This helps avoid being stuck in the past and opens the mind to new possibilities. Christina Tosi of Milk Bar is given as an example - when her stores closed due to COVID, she innovated new revenue streams like online baking shows and expanded distribution, growing the business beyond what it was before.

In a crisis, leaders should focus on decisively moving to survive longer-term rather than just hoping for short-term improvements. They should pivot the business model to meet current customer needs rather than sticking to outdated approaches. Leaders need to take action, communicate positively, and empower fast decisions without excessive approvals holding them back.

The story of the International Champions Cup soccer tournament reinvention is also provided as an example of successfully pivoting a struggling business to leverage existing relationships into new opportunities when the original model wasn’t working. In crises, being willing to completely reinvent and retreat from failing approaches can unlock major success. Overall, the passage encourages creative thinking of new possibilities in hard times.

  • The author experienced personal struggles with COVID-19 early on, spending almost a month in isolation while infected. But he saw it as an opportunity rather than a disaster, gaining time to write a book.

  • True leadership is acknowledging disasters while still finding your best path forward, not assuming the road is “doomed no matter how hard we try.” You can always change course tomorrow.

  • It’s important not to waste opportunities, even fleeting ideas or instincts, as they are a scarce resource. You may regret not acting if an opportunity passes by due to indecision.

  • Whether events turn out “good” or “bad” is hard to say - crises can unlock potential. The author provides examples of people who thrived after overcoming difficulties and mistakes in their past.

  • Adaptability and resilience are important qualities for making the most of what life presents, even if it initially seems like a disaster or setback. Opportunities can arise from unexpected places.

  • Michael Milken transformed his life after serving time in prison for securities violations. He became a philanthropist focused on health care issues. He donated $80 million which led to George Washington University renaming its public health school after him.

  • Milken’s experience shows that people can change for the better after facing adversity. While his original actions were wrong, he used his situation to become a positive force through his philanthropic work.

  • Crises and difficult situations often force us to take bold action in order to survive or overcome challenges. This pushes us outside our comfort zone in a way that normal times do not.

  • Without a crisis pushing us, it can be easy to maintain the status quo and do nothing even when change may be beneficial. Having many options can also paradoxically lead to paralysis rather than action.

  • However, crises present opportunities if we face them head on rather than avoiding the problems. Even negative experiences can be leveraged into new successes if we push ourselves outside our normal boundaries. Running toward threats rather than away from them is important for growth.

So in summary, the key lesson is that adversity and crisis, while difficult, can ultimately lead to positive change and new opportunities for growth if faced proactively rather than avoided. People are capable of transformation even after serious mistakes.

  • The author argues that recognizing patterns is important for success, both from observing trends over time as a reporter and spotting issues in past business deals that lead to mistakes.

  • Two major external obstacles discussed are choosing the wrong business partners and bad investors. For partners, the author advises retaining control, only partnering out of necessity, and watching for signs of misaligned visions or effort levels.

  • For investors, the key is finding those who will not harm the business. The failed juicer startup Juicero is used as an example of investors forcing out the visionary founder, which compromised the company’s direction and long-term goals in favor of short-term discipline.

  • In both partnerships and investments, the author’s message is to carefully evaluate alignment, commitment levels, and motivations upfront to avoid situations where external stakeholders get in the way of the business vision due to mismatched expectations or power dynamics. Due diligence on “partners” is emphasized.

  • Doug, the founder of Juicero, believes the company made some critical mistakes and was ahead of its time. The investors decided to stop funding the company, but Doug felt there was still potential in the business.

  • Relying too heavily on investors can limit a founder’s ability to freely execute their vision. It’s important not to give stakeholders too much power unless it’s truly necessary.

  • Startups often need investors for funding, as running out of money will end the business. Doug’s previous company had promising ideas but raised hundreds of millions and still failed due to lack of profits and not having enough money to survive in the long run.

  • Founders often believe their ideas will succeed sooner than the market is actually ready. Joe Park from Kozmo knew e-commerce was the future but delivery was still new. The same happened with Doug’s restaurant reservation company RESY - the initial vision was ahead of its time.

  • It’s difficult to predict the timeline of success. What seems like hesitation could actually be very early. Founders need to structure their businesses to have enough time and runway to succeed rather than reacting to impatience.

  • Startups can be compared to similar companies, and the failure of one can negatively impact others seen as comparable, even if the businesses are different. It’s important for early companies to define their uniqueness.

  • Founders often want to control everything themselves due to competence, but this can lead to micromanaging, failing to delegate, and taking on too many responsibilities as CEO. Hiring and empowering the right people is crucial to scaling.

  • The NFL culture places a high value on head coaches having innate leadership skills, so there is little on-the-job training for new coaches. As a result, many are fired within 3 years as they struggle to evolve into the complete head coach role.

  • Mike Tannenbaum and Rex Ryan say new coaches need to evolve into the job and not be afraid to hire talented assistants. Rex was unusual in not being threatened by hiring people better than him. Many coaches make the ego-driven mistake of only hiring people less capable than themselves.

  • In business, leaders need to render themselves obsolete in virtually all roles and ensure the company can still function if they’re absent. This requires hiring people better than you and trusting/empowering your team to shine.

  • Nicholas Horbaczewski of Drone Racing League provides an example, reluctantly hiring a president who supercharged the company’s growth by bringing new strengths. One person can’t do it all alone.

  • The key lessons are to not be afraid to hire people more talented than you, empower your team, and recognize your own limitations so the business doesn’t rely solely on you. Evolving into a complete leader requires delegating responsibility.

  • Sometimes entrepreneurs get too attached to their ideas and businesses and refuse to admit failure, chasing them long after it’s clear they’re not working.

  • Determining signs that it may be time to move on include no profits after 3+ years, not having users/revenue/traction despite time and investment, or needing to constantly raise more funding through late funding rounds.

  • The sunk cost fallacy causes people to keep investing in failed endeavors just because they’ve already spent money on them. You have to recognize when the market isn’t interested.

  • It may also be the case that the business idea is good but the founder is not the right leader for it. There needs to be strong alignment between the founder’s passions and the business.

  • Some founders aren’t ready to lead yet and need more growth and experience before taking on a leadership role with a company. A strong founder can overcome weaknesses in an idea but not vice versa.

  • Entrepreneurs are advised to honestly assess whether they are truly the best person to execute the vision and drive the business through challenges, and consider if they need to find a different idea or develop more first before pursuing the current one.

  • Self-awareness and the ability to admit when you’re wrong is critical for leadership success. Good leaders act quickly when changes are needed and course-correct without embarrassment.

  • The story is shared of ramen company immi, which had a terrible initial product but the founders were self-aware and improved it based on feedback. Their transparency built trust and attracted investors.

  • Hidden issues will eventually be revealed, so leaders should proactively find flaws and fix problems. “Missing conversations” should be had to openly discuss concerns rather than make assumptions. Good leaders eagerly plug holes to improve.

  • If a leader seems threatened by discovery or isn’t fully transparent, that’s a red flag even if the specific issues aren’t known. Investors want openness and willingness to do hard work.

  • A industrial psychologist is brought in to evaluate major deals. Their reports often highlight flaws like over-reliance on intelligence without emotional skills, deference to authority without confidence, poor political savvy, not distributing credit, and evading questions. Self-awareness and willingness to improve are key.

  • People often don’t take advantage of the assets and opportunities they have in the present to prepare for the future. Football players, for example, can leverage their current fame and status to make connections and set themselves up for life after retirement.

  • It’s important to use every advantage you currently possess, rather than waiting until some future point. Current relevance and name recognition are valuable assets that decrease over time.

  • A football star named Byron Jones is given as an example of someone who planned ahead. Even before being drafted, he focused on skills needed for the NFL Combine. He holds the world record for longest standing long jump.

  • The author advised Byron on ways to leverage his current fame and platform, like social media campaigns, to become an even bigger star and gain deal flow as an investor. Byron wants to be a serious investor post-retirement.

  • Everyone has some unique asset - a quality, circumstance, or story - that can help them achieve their dreams. It’s important to recognize those advantages and use them proactively rather than waiting for the future.

  • We should look for our unique assets and advantages rather than focusing on perceived weaknesses after being laid off from a job. Everyone has skills, knowledge or connections that could be leveraged in new opportunities.

  • Examples of leverageable assets include special talents, access to particular networks or industries, lived experiences that provide unique perspectives. These are often overlooked but can be highly valuable.

  • When acquiring or investing in companies, look for their core leverageable assets that could be extended or amplified, like brand recognition, experience scaling similar brands, customer goodwill etc. This provides a strategic advantage.

  • Rather than incremental small steps, we should aim for big leaps that don’t require unnecessary experience or credential building. Conventional wisdom often advises patience and paying dues, but waiting prolongs progress unnecessarily.

  • If we truly have the skills and conviction for a role or opportunity, we shouldn’t disqualify ourselves just because we lack conventional experience. Others will often back ambitious ideas before experience is fully in place.

  • Incrementalism may feel safer but leads to slower progress over time. Taking calculated risks on big leaps can accelerate career trajectories and open up greater potential. We should challenge risk-averse mindsets.

Here are the key points from the passage:

  • Francesca Gino from HBS argues that following your passion instead of a typical career path leads to faster learning and more success. However, many MBA graduates go to consulting firms thinking it will lead to ventures of their own, but the timing never seems right.

  • The author urges people to escape corporate hierarchies when possible, as traditional business models try to organize and control people. Places like law firms and consulting firms keep you in bands and slowly move you up, limiting growth. It can be soul-crushing.

  • When you move to a new organization, you get a fresh start and can rise up ranks faster than waiting in a hierarchy. You should only stay at a job if you truly love it.

  • The author recognizes that escaping traditional paths can be harder for some due to factors like race and gender. Tracey Thompson, a Black woman, feels she carries more responsibility to represent her race and gender well. Society has stacked the deck unfairly against some.

  • Tracey’s goal of leveling the playing field by backing diverse founders and increasing diversity on boards and in leadership is inspiring to the author. Diversity can feed success if barriers are recognized and addressed.

  • Jesse Palmer was the first professional athlete to appear on The Bachelor in 2004 and found early success in television.

  • He has had a successful career hosting various food and cooking shows on networks like Food Network as well as working as a correspondent for Good Morning America.

  • Though he still had opportunities to play football, Jesse saw potential in media and made the decision to pursue a career in television instead of continuing as a backup quarterback.

  • It was difficult to walk away from football but he took opportunities in television when they arose. Jesse is now the host of The Bachelor and The Bachelorette franchises.

  • The passage reflects on Jesse’s career path from professional athlete to television host and how he embraced opportunities in new fields even if they weren’t expected paths for a former NFL player. He was open to different experiences that ultimately led him to find success and fulfillment in television.

  • The passage discusses three key traits that are important for problem solving and getting a full perspective on a situation: defiance, detail, and finish.

  • Defiance means stubbornly insisting on your vision and refusing to be swayed from it, as long as you know you are right. It also means advocating for your position and not remaining silent if others are making wrong decisions.

  • Detail means recognizing that small incremental efforts can make a disproportionate difference. Getting details right is a proxy for competence, and mistakes in small details may indicate mistakes in bigger issues.

  • Finish means applying maximum effort all the way to and through the completion of a goal. It is important to avoid getting tired or sluggish near the end and instead do your best work right up to the finish line.

  • These traits can help understand situations fully, get different viewpoints, and solve problems effectively. The passage advocates adopting these characteristics to analyze information and make good decisions.

  • Sean is the CEO of an insurtech startup called Kin that is reinventing the home insurance industry by going direct-to-consumer and removing middlemen.

  • Sean has a calm demeanor that helps him make rational decisions even in stressful situations. He is able to regulate his emotions and not panic, which gives investors confidence in him.

  • Storytelling and communication skills are critical for any company to explain their vision and mission to various audiences like investors, employees and customers. While these skills are important for consumer-facing companies, they are also important for B2B companies as buying decisions are ultimately made by individuals.

  • Kin struggled with communicating their innovative approach to the insurance industry. The author brought in communications expert Tom Carroll to help rebrand Kin and better convey their message to the market.

  • Effective communication can help close the gap between when a company has a vision and when the market understands and buys into that vision. It is an important tool for companies that may be ahead of their time.

  • Cathie Wood, founder of ARK Invest, believes innovation is often underestimated. She had a price target for Tesla that was ultimately wrong but Tesla still greatly exceeded expectations.

  • Wood explains that markets can be inefficient and those assessing innovative companies may not have direct experience with the innovations. Her office aims to be the antidote to this by employing young analysts excited to explore emerging technologies.

  • People initially doubted visions like Tesla’s but visionaries need good communicators to help translate their vision and bring it to life for others. Over time, views tend to catch up as understanding increases.

  • No individual can do everything alone. Leaders need a strong team to help execute across key competencies like investment management, legal, negotiating deals, and managing the diligence process. Great teams allow leaders to focus on their strengths.

  • It’s important to recognize one’s own gifts and fit within a team, as well as when someone may be hindering an organization’s potential success through difficult behavior. Issues typically stem from someone at the top limiting others. The summary then discusses common types of difficult personalities that can damage organizations: Withholders, Hijackers, Victims, Martyrs, and Gaslighters.

  • Leaders should avoid dealing with difficult people when possible and recognize problematic behaviors directed at others will eventually be directed at oneself. If difficult traits are present from the start of a relationship, it’s best to end it quickly before problems worsen.

  • The author argues that victims see crises and setbacks as validating their belief that the world is out to get them and they cannot succeed. They fail because their mindset is self-fulfilling.

  • The author took a positive mindset after getting cancer at 32. Rather than feeling sorry for himself, he was thankful it was a treatable cancer and saw his situation as making him exceptional.

  • The author discusses different negative leadership archetypes like victims, martyrs and gaslighters. Victims blame external forces for their failures. Martyrs take on too much work to confirm their narrative of being overburdened. Gaslighters try to rewrite reality and deflect blame.

  • The best leaders empower others and unlock their potential. They hire people better than themselves to help the organization succeed. Their own success comes from enabling others’ success. This allows the whole market and company to expand.

  • The author provides an example of how he helped an entrepreneur named Aidan Kehoe find success in cybersecurity by identifying needs and empowering others through his network and mentorship.

  • Ransomware incidents against small businesses were skyrocketing in the years before SKOUT was founded. Aidan saw an opportunity to help these smaller companies that couldn’t afford expensive cybersecurity solutions and were being ignored by bigger criminal networks.

  • With backing from the Pascucci family, Aidan launched SKOUT as a cybersecurity company focused on helping small businesses. Despite lacking formal training, he was able to connect with small business owners and become a trusted resource for them.

  • Building the business was very cash-intensive in the early years. Aidan convinced the author and Stephen to buy the company from him to provide deeper pockets and patience for losses during the ramp-up phase.

  • Executive coaching from Dr. Finfer helped uncover issues at SKOUT but also showed Aidan’s commitment to growth. Sharing the brutally honest coaching report with his team demonstrated vulnerability but also a desire for improvement.

  • After hitting challenges with investors and his daughter’s health issues, Aidan considered quitting but instead took a break and rebuilt his executive team. This helped turn the company around.

  • SKOUT was acquired at a large valuation only a few years later, providing a successful outcome and financial security for Aidan and the team. The author finds helping others unlock their potential, as with Aidan, to be very rewarding.

The passage discusses examples of people who burned their boats and manifested bold dreams in unexpected ways.

It describes how baseball player Andre Dawson became unexpectedly passionate about running a funeral home after retiring. Micah Johnson pursued art with the same dedication he had for baseball, generating over $2 million from NFT sales of his Black astronaut character.

Former CNN journalist Laurie Segall launched her own media company to have more creative control over her work. She saw how crustaceans need to shed their shell to grow, and realized she needed to leave her job to fully pursue her vision.

The passage emphasizes that burning one’s boats involves taking a risk to pursue fulfillment on one’s own terms, even if the path is unfamiliar or far-fetched. It conveys that independence and owning one’s journey are keys to manifesting dreams in a deeply rewarding way, despite the inherent fears of leaving a comfortable situation.

  • The passage discusses the concept of “lf-censoring” or holding back part of oneself out of fear or desire to defer to others. It argues that trying to “shine less” and not stand out is a form of self-censorship driven by insecurity.

  • It then contrasts this with being fully empowered to be oneself without holding back. When pursuing dreams and goals, it’s important not just to eliminate backup plans but to fully commit oneself without reservation.

  • It provides an example of a successful sunless tanning and hair removal business that was sold to an investor after growing to 10 locations over a decade. The founders felt less pressure and stress after the sale but also more freedom and clarity to pursue other ventures.

  • The key lesson is that achieving success or profit doesn’t have to mean stopping. One should always look ahead to continued growth and impact rather than seeing any achievement as an end point. The true joy is in the ongoing pursuit and progress, not any single accomplishment.

  • The passage discusses John Skipper’s experience launching his own media studio, Meadowlark Media, after retiring from his role leading ESPN.

  • Starting the business in his mid-60s gave Skipper new excitement and rewards. He has learned a lot from the experience of starting a business for the first time.

  • Meadowlark gives Skipper more freedom and flexibility to work on projects he’s passionate about and with people he respects. It’s more rewarding than running a huge corporation like ESPN.

  • Skipper says you don’t need to constantly scale up a business to have fulfilling work. His studio is much smaller than ESPN but still very rewarding.

  • At the time of writing, Meadowlark had just signed a multi-year deal with Apple to produce documentary and unscripted content for Apple TV+, indicating the business’s success and growth potential.

  • The speaker broke down after her mother passed away. On the day she got her scholarship in honor of the speaker’s mother, another scholarship recipient’s daughter hugged her and said it was okay and that she was proud of her.

  • The other scholarship recipient, Ekaterina, fled Russia to escape abuse. She came to America without English and never thought she’d go to college. When she got diagnosed with breast cancer, she got accepted to Queens College with the scholarship. She found strength from reading the speaker’s commencement speech.

  • The speaker’s mother always thought her life meant nothing. After she died, the mayor offered to honor her. The speaker asked if they could drive her casket through her beloved Queens College campus one last time, as her mother had begged to see it again before dying.

  • The scholarships now make the speaker feel like she is helping rewrite her mother’s story and legacy, which now lives on through strong women recipients instead of ending alone in her mother’s apartment.

  • Complete confidence in your plan and ability to execute is a sign of lack of self-awareness, as you will likely fail. Problems create opportunities for innovation as they force you to think more creatively.

  • There is no “final port” - no point where you can stop striving and growing. While it’s okay to recharge, staying still long-term won’t bring the same joy as pursuing new adventures and dreams. People’s greatest regret is dreams left unpursued.

  • Problems provide opportunities to demonstrate ingenuity and problem-solving skills. Put yourself in challenging situations without clear answers to surprise yourself.

  • Following insights, even when others miss them, can lead to great success like starting companies that fundamentally change industries. Turning down jobs to pursue boldest visions can change life trajectories.

  • It’s important to have a “why” - a purpose larger than oneself that provides motivation, like helping others overcome hardships. By intervening to help others rather than look away, one can alter lives and find meaning healing past traumas.

  • Speaking on important causes like helping migrants and refugees provides opportunities to rally others to significant positive impacts through fundraising and advocacy. Challenging situations can inspire thinking about supporting those fleeing even worse circumstances.

The passage contrasts a wealthy neighborhood in Central Park with Father Leonir, a priest providing aid to a fleeing family in a war zone.

At an event, the author goes off-script and shares his experience growing up poor in Queens and relying on the local Catholic food pantry.

Later, the author meets Pope Francis privately. The Pope emphasizes the importance of solidarity and compassion, reminding the author to “go to the periphery, not just of your body, but of your soul.”

While on vacation, the author hears the story of a historic boathouse that burned down. To save the boats, the owner sank one by axing its hull so the fire wouldn’t destroy everything he built.

The passage draws parallels between risking everything to save what matters most, the importance of compassion especially for the marginalized, and having courage to face difficult challenges by finding creative solutions in dire situations.

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About Matheus Puppe