Notes - Sweaty Startup

April 29, 2025

Introduction

Entrepreneurship is presented as the premier, and arguably sole, path to significant wealth, as "trading your time for money won’t work" for achieving true financial freedom. While the author previously encouraged everyone to start a business, he now issues a "stern warning": most people "simply don’t have what it takes". His fear is that his work might persuade individuals into ventures they cannot handle, leading to failure, divorce, ill health, and lack of freedom and hope.

Business ownership is acknowledged as "brutal and stressful," demanding a unique skill set that most people neither possess nor can cultivate. The average person is described as unhealthy, broke, and having poor relationships, often unable to manage even a $500 surprise expense. Such individuals, who struggle with personal life management, are ill-equipped to manage an organization with employees, customers, logistics, and inherent problems. This perspective is rarely found in other entrepreneurship books. For most, a better quality of life is achieved by working for a good boss at a good company with good pay and minimal stress, as most dislike chaotic environments, sales, and financial risk. However, for those who feel determined, the book offers guidance.

The author recounts his experience as a junior at Cornell University in 2011, where classmates pursued grand, revolutionary ideas requiring millions in funding. In contrast, his idea was "boring, old-fashioned"—a student pickup and storage service. He aimed to store students' belongings over the summer and return them in August, simply by "do[ing] things a little better than the competition". His professors and peers dismissed it as unscalable and non-innovative, noting existing competition. Yet, he observed a similar local company generating over $600,000 in revenue annually with 30% margins (around $200,000 in profit) despite being inefficient (using clipboards, no same-day appointments, poor marketing, terrible website). Crucially, $200,000 in profit was nearly three times what he could make from a typical post-college job.

The "cold hard truth" for the author is that entrepreneurship is not about "trying to change the world with the next scalable idea". Instead, it's about "starting small, looking for a way to make good money doing something simple, and copying proven strategies that work". His first company, Storage Squad, was a small idea in a crowded market. He started by distributing flyers, securing a few paying customers, and reinvesting that profit, purchasing his first asset—a $1,500 cargo van—and utilizing existing resources.

His approach was "simple and unsophisticated": he wasn't focused on educating a customer base, following a passion, seeking funding, building a network, competing with leading computer scientists, or proving a concept. His sole attachment was to adding value and quickly exchanging it for money. He studied competitors to understand their operations, pricing, and value delivery, deciding if he could outperform them. His decisions were logical, not emotional, competing against outdated methods (fax machines, clipboards, paper ledgers) by being "a little faster and smarter". Storage Squad was profitable from day one, unlike his classmates' complex ideas, none of which generated revenue.

The author emphasizes his own ordinariness—average test scores, no coding skills, no entrepreneurial family background. He states that neither he nor his partners are "brilliant or special" and assures the reader that they don't need to be either. This alternative, simple business method works, and he is "living proof". Storage Squad's early profits allowed him and his partner to build their first self-storage facility, which they sold in January 2021 for $1.75 million, debt-free.

Currently, the author owns 50% of a company managing sixty-eight self-storage facilities (over two million square feet, $150 million market value) and acquired another company for $52 million in April 2024. At thirty-five, he lives in Athens, Georgia, with his family. He is also involved in several other "boring businesses" (recruiting, real estate services, marketing, web development, insurance) that generate multiple seven figures in personal cash flow annually, with his net worth around $50 million. He openly discusses net worth, despite its fluidity due to assets tied up in illiquid investments, asserting that it can be discussed without arrogance when framed appropriately.

The author has no day-to-day job in his companies; he is not a bottleneck, and small problems don't reach him. His time is spent making "key decisions on the big stuff," such as property acquisition hurdles, market expansion, and hiring/compensation strategies. He works hard when opportunities arise, for example, building a recruiting team in South Africa, but some months he works little, traveling or playing golf. He shares this information not to brag, but to establish credibility as a source of advice, urging readers to critically evaluate his guidance based on their own circumstances. He highlights that business is dynamic, with countless paths to success, and his journey is not a universal template.

The book is structured into three sections: "Opportunity" (identifying profitable ventures), "Skills" (developing entrepreneurial capabilities), and "People" (building a strong team). These three factors are crucial for achieving "the ultimate form of success and wealth: Freedom". Freedom is defined as "to do whatever you want to do, whenever you want to do it," acknowledging that many currently lack this. The author's goal is to help readers achieve this change. Part I focuses on recognizing valuable opportunities often overlooked as "too hard and too boring," identifying what businesses to avoid, and re-evaluating everyday businesses. It also covers assessing personal skills and choosing a starting point. Part II delves into the necessary skills and mindset for company building, including managing fear and stress. Part III discusses the importance of people, from finding high-performers to delegating tasks, which is the "path to freedom". With freedom, one can enjoy success or continue building with new skills, networks, and capital.

The author emphasizes that his advice is his opinion, shaped by personal experience, failures, successes, and continuous adaptation. He encourages readers to form their own opinions through "deep introspection," rather than blindly following the crowd. Successful individuals, he notes, are constantly "figuring it out as they go," making data-driven, unbiased decisions, and holding "strong opinions that are loosely held" to maintain flexibility. Business strategy is not absolute; no single principle applies universally. Therefore, he cautions against blindly trusting anyone, including himself, especially those claiming 100% certainty, as business is full of surprises.

Entrepreneurship is portrayed as inherently difficult, stressful, and not glamorous. The pressure is intense, with employees relying on you for rent, entitled customers, challenging negotiations, costly mistakes, and constant problems requiring your intervention. There is little external praise for successes; employees won't thank you for paychecks, and customers won't thank you for fulfilling promises. Success brings significant stress, challenge, and responsibility, including a duty to guide employees. Despite the difficulty, for many entrepreneurs, it is the only path they desire.

Part I: Opportunity

Chapter 1: Leverage

The author illustrates the concept of leverage through a friend's experience. This friend was a highly accomplished individual—valedictorian, Columbia graduate, near-perfect LSAT score, and Harvard Law graduate at twenty-six. He quickly rose at Williams & Connolly, a prestigious litigation firm, earning over $1 million annually by age thirty and on track for partnership. His life, from an outside perspective, seemed like a great success, involving extensive travel and courtroom work.

However, when his wife became pregnant, he was assigned a high-profile case that would make him miss the birth of his first child. His boss, a partner at the firm, dismissed his plea, stating that such sacrifices were traditional for attorneys seeking partnership and part of the price for a seven-figure salary. His boss epitomized what the friend did not want to become: fifty years old, divorced, unhealthy, with no relationship with his children, working seventy-hour weeks, rich but lacking time to enjoy it, and having "zero control over his life". This partner was beholden to clients and senior partners. Realizing this, the friend quit immediately and changed careers, acknowledging that his decade of sacrifice and top-tier achievement had led him to "win the game" of society, but it wasn't a game "worth winning at all".

The author warns against societal glamorization of careers like law, medicine, or Big 4 accounting. He advises looking at the lives of those who have "won" these games—often working sixty hours a week, overweight, divorced, and stressed. He compares these careers to "hot-dog-eating contests" where skill in one area only rewards you with more of the same, not a better life. Status, he argues, often inversely correlates with quality of life. Similarly, most startups fail to deliver significant wealth, demanding sacrifices of time, health, and relationships for little financial return.

The author defines winning as achieving consistent monthly income that allows you to "do what you want to do when you want to do it". This requires choosing a career with a "high return-on-time," meaning that current work yields long-term payment even when the work slows or stops, leading to freedom. Without this freedom, a great life is virtually impossible. He describes a state of "zero leverage" where one is easily replaceable, owns no income-generating assets, lacks options, and is controlled by others. Conversely, "high leverage" means being hard to replace, owning assets/shares, having many options, and being indispensable, allowing you to "call the shots". Leverage, the author concludes, is "the key to life".

The Three Keys to Leverage

Leverage is defined as anything that maximizes your advantage, like a pulley system making heavy lifting easier. In business, this translates to productivity: one person working one hour achieves one hour of work, but with forty employees, forty hours of work can be done in one hour. Most people have limited leverage, trading their time directly for money, like earning $15 per hour. Those with significant leverage can earn $300 per hour, for example. "Extreme leverage" involves multiple passive income streams, such as stock dividends or real estate managed by others, making one insulated from decisions by bosses or partners and diversified from risk.

The author emphasizes looking for truly wealthy individuals in your own town—those who "do what they want to do when they want to do it," like playing golf on Mondays or going fishing on Wednesdays. He distinguishes this from internet billionaires or those chained to high-paying corporate jobs. These local, truly wealthy entrepreneurs possess "real leverage".

He provides examples:

The lawyer friend, despite earning $1 million annually, lacked leverage because he had no control over his time, couldn't work remotely, required permission for vacations, and was expected to miss significant family events like his child's birth. His boss and clients held the leverage. In contrast, many of the author's entrepreneur friends work less than forty hours a week (often as little as ten), earn millions, don't do manual labor, and can travel spontaneously. Their secret, the author reiterates, is leverage.

The three keys to acquiring leverage are:

  1. Network: It's less about who you know and more about "who knows you". Building a network involves connecting with people who can work for you, make decisions, help, partner, buy from, invest with, and advise you. Eventually, a strong network means you can pay people to run your companies, attract investors, recruit talent, and be considered for opportunities. Success in business is rarely achieved alone.
  2. Skills: This refers to your ability to "make things happen". Building businesses and accumulating income-generating assets demands hard decisions, a specific mindset, and proficiency in various areas: sales, leadership, hiring, management, delegation, and decision-making. These skills are not innate but acquired through practice, much like building muscle in a gym rather than just reading about it. The author emphasizes that reading the book alone won't help unless you "put some of this stuff into action".
  3. Capital: Having personal financial security makes building a business "ten times easier". It allows stress-free payroll, investment in equipment and marketing, and growth without added personal stress. Sufficient cash flow enables hiring, investing, and, crucially, taking risks. Wealthy entrepreneurs can move faster, invest in growth, and hire ahead of revenue, outperforming undercapitalized bootstrappers who cannot afford mistakes.

The author describes business as a "chicken-and-egg problem" in these three areas, as it's advantageous to have them, but they are built through practice and company-building. Successful entrepreneurs achieve leverage by slowly and steadily acquiring network, skills, and capital, starting from a disadvantage and progressively building their advantage. It's a ladder that takes time and effort, with no skipped steps.

The No-Asshole Rule

When one has little leverage, they are often forced to "bend over backward for customers," tolerate disrespectful partners, and accept unfavorable investment terms. However, as experience and wealth grow, this shifts, allowing you to "stop doing business with assholes". Leverage grants the freedom to remove yourself from undesirable situations, firing bad customers, breaking up with bad partners, and buying out bad investors. This allows you to build a "tribe" of people who genuinely want to collaborate and improve with you.

Initially, with no leverage, you are a commodity. But as you gain skill and experience, the balance of power shifts, enabling you to negotiate more for yourself. Eventually, you might find that the other party becomes the commodity. This transformation leads to an "easier" business life, more money, and more exciting opportunities, creating a continuous "snowball" effect of increasing leverage and wealth.

The author's own journey exemplifies this. For over ten years, he endured a "slow, tedious grind". In the early days of Storage Squad and his self-storage business, he frequently dealt with abusive customers because he desperately needed their money. Similarly, in real estate, he accepted money from "anybody and everybody," agreeing to their terms because he needed their capital more than they needed him. Today, his multiple companies generate over $500,000 in monthly personal income, and he possesses a unique skill set that makes people need him more.

He shares specific examples of exercising this leverage:

Operating from a position of leverage is described as a "cheat code to a happy life". It grants options, personal capital, the ability to pay bills, and the freedom to prioritize mental well-being over unwanted obligations. When you have leverage, you are not forced to endure difficult individuals, and "when you never have to do what another grown human tells you to do if you don’t want, that’s when life gets fun".

Return on Time

When evaluating any opportunity, the author suggests asking two fundamental questions:

  1. "What is the return, in dollars, for an hour of my time today, a year from now, and ten years from now?"
  2. "If I stop working, do I stop getting paid or will I keep getting paid?"

These questions, he argues, provide all necessary information about one's choices. He offers comparisons:

If your goal is wealth and freedom, you must consider if your current career path allows for passive income in the future. If not, it's time to reevaluate. The amount of money earned is not correlated with hard work, but with "how hard you are to replace and thus how much leverage you have". Being easily replaceable means low leverage and capped earning potential, while being "impossible to replace" means high leverage and unlimited potential. The objective is to start businesses and reach a point where others need you more than you need them. This is not an overnight process.

The author explains that future passive income, even if it seems far-fetched, creates leverage. For example, $50,000 per month from three controlled sources, while spending $20,000 per month, provides immense leverage, ensuring no one can control your life. Unfortunately, many high-status professions offer "zero leverage"; doctors, unless they invest saved capital, cannot stop working and continue to get paid. Most W-2 jobs involve a perpetual trade of time for money. Exceptions like wealth management, insurance, and sales can create future passive income.

The first practical goal for someone seeking leverage is to start small: aim for $2,000 per month from something owned (side hustle, small business, real estate). Then, grow this to $5,000, then $10,000, then $20,000, at which point you gain the leverage to leave an undesirable job.

It’s Time to Redefine Success

The author challenges the reader to redefine success and true wealth. He provides an exercise: first, describe your current life—where you live, how much you work, your typical Monday morning, your week, and how you spend your time. Then, imagine your "perfect week" if money were no object and you didn't need to work, answering the same questions. This process is about "Build[ing] your ideal life".

True wealth, the author asserts, is not just about money, but about "freedom. True wealth is being able to do what you want, when you want, without being chained to a desk or beholden to someone else’s schedule". He notes that 99% of people spend their careers doing disliked tasks to support a lifestyle only enjoyed in evenings, weekends, and limited vacation days. They are subject to others' control over their time.

He argues that someone earning $1 million annually but working seventy hours a week is not wealthy, while someone earning $150,000 annually but working five hours a week, mountain biking in Colorado, and fishing in Florida Keys is "very wealthy". True wealth is a "function of time and money".

The second part of the exercise involves calculating the monthly after-tax income needed for your ideal lifestyle, including all expenses like mortgage, food, vehicles, healthcare, travel, and hobbies. The author's own goal at twenty-five was $20,000 per month, working five hours a week, which he achieved by thirty (equivalent to $30,000 today). His ideal lifestyle was simple: a nice house for five kids, good schools, reliable cars, dining out, some travel, a country club membership, and golf. He didn't need lavish luxuries like a private jet or a huge house. He believes the amount needed for true wealth and leverage is "far lower than what you imagine". Freedom, he concludes, is about leverage and time, allowing for physical health, being a great spouse/parent, and spending time with loved ones.

He uses a poker analogy: your "chips" are your time, a finite resource. The "million-dollar question" is how to invest this time to maximize the odds of making the money needed for your desired life five years from now. For him, the answer was not a W-2 job or a venture-backed startup, as regular jobs wouldn't achieve his goal, and most startups fail after consuming significant time. He didn't aim for a billion-dollar company or status, just $30,000 per month without being chained to a desk. His singular focus led him to pursue a "sweaty startup"—a "boring business" where he picked up and delivered boxes for money.

Chapter 2: Business Is a Race

The author and his business partner, Dan Hagberg, started Storage Squad in fall 2011 during their senior year at Cornell. They observed their Ivy League friends securing high-paying jobs in investment banking, hedge funds, and consulting, starting at $80,000 to $120,000 annually. This created a "serious opportunity cost" for the time they spent building their business. Eight months in, the author felt anxious and unsure about entrepreneurship, especially as others questioned his unconventional path. To hedge, he simultaneously pursued corporate job opportunities, receiving an $80,000 offer from Coca-Cola in 2012, while Storage Squad had only $5,000 in total revenue.

His father, surprised and apprehensive, questioned his choice to use an Ivy League degree to "drive a moving truck," urging him to "make it count". Facing similar offers, the author and Dan set a decisive goal: either "fail spectacularly or make something happen". They aimed to avoid a slow failure after burning five valuable years. They embraced discomfort and prioritized speed.

Their ambitious plan involved launching Storage Squad at three other major universities (Illinois, Indiana, Iowa) by convincing friends and family members (Dan's cousin, author's best friend, Dan's best friend) to operate local branches under a profit-sharing model. They used more student loan money to buy three additional cargo vans. Their singular goal was to acquire over 250 customers that spring as a "proof of concept". Failure to reach 250 customers meant shutting down the business and getting jobs.

This period was intensely uncomfortable, marked by uncertainty about employee compensation, warehouse storage, and funding for supplies. All this occurred during their senior year finals week and while they were finishing their Division I track careers, with the author simultaneously training for the Olympic trials and pursuing his future wife. By May, the author had passed his finals, graduated with a 3.4 GPA, won a decathlon conference championship, placed eleventh at the USA championships, and solidified his relationship. Storage Squad hit 253 customers, leading them to commit to entrepreneurship.

The author states that his entire entrepreneurial career has been a "race" ever since, and the reader's should be too. Time is an invaluable and irreplaceable asset, making it crucial to get a business off the ground quickly to learn, improve skills, and determine its viability. The initial years were financially modest: less than $15 per hour ($30,000 total) in the first year, and about $25 per hour ($50,000 pretax profit) in the second—far less than his friends' corporate salaries, but more stressful. He made many mistakes but persisted with a positive attitude, eventually out-earning his friends and building the self-storage facility that generated his wealth. His consistency, confidence, and speed created momentum. The common mistake, he notes, is moving too slowly to maintain comfort, which often leads to giving up.

Act Now and Ask Questions Later

The author advises that if you are not yet wealthy, your first business (or fifth or tenth) should be profitable within the first six months. If not, or if the model lacks profitability potential, "go do something else" due to the high opportunity cost of time. Successful individuals act with urgency, embracing an "aim, fire, aim, fire, fire, fire, and ask questions later" approach rather than excessive planning. "Perfect has been and always will be the enemy of progress".

He contrasts this with a Cornell friend who constantly planned, researched, and studied entrepreneurship, reading books, taking classes, listening to podcasts, and analyzing biographies. This friend would spend months on an idea, talking to customers and building plans, only to abandon it. Despite building websites, creating MVPs, winning pitch competitions, and even getting close to raising money, he would always find flaws and get "cold feet," never pulling the trigger. This "analysis paralysis" is common among aspiring entrepreneurs, rooted in the belief that an idea or plan must be perfect for success.

The "cold hard truth" is that "Execution is a thousand times more important than your idea". Winners excel at the "boring stuff": hiring, delegation, selling, logistics, and communication. Business is a race with small opportunity windows that close quickly; hesitation means missing out.

He gives an example of a resourceful UGA student interested in starting a recruiting firm for the construction industry. The author advised her to "get after it" by cold-calling five owners. A year later, she was generating $30,000 per month in revenue with an assistant, primarily doing the work herself. Her success wasn't due to a revolutionary idea but from "get[ting] her hands dirty".

Phenomenally successful people demonstrate a "bias toward action". They identify opportunities, move quickly, and trust their intuition. They start with low-risk decisions, improving their decision-making skills over time, which builds momentum. A disclaimer: this doesn't mean acting recklessly. Preparation should align with risk; for a large investment, do your homework, but for low-risk endeavors like power washing, "get off the couch and go!". Early mistakes are less impactful. Real entrepreneurs act on ideas immediately, seek payment, and get "sweaty". They fail quickly and adapt. The author implemented his Storage Squad idea "insanely quickly," generating $5,000 cash within two weeks. He reiterates that "Analysis paralysis is a horrible disease".

Stop Worrying What Other People Think

The author observes that many "below-average people" achieve phenomenal wealth simply because they are not insecure. They possess confidence, move forward despite others' opinions, are unafraid of failure, and don't dwell on what others might think. Developing "thick skin" is challenging but essential. It requires taking risks, putting yourself out there, and enduring uncomfortable situations, including negative reactions, jealousy, and attempts to tear you down, which are "just a fact of life" when you do things differently, especially when you succeed. The key is to practice letting it go, recovering quickly, and moving on.

He recounts a personal experience: being bullied in elementary and high school, and later, during Storage Squad's early days, overhearing his track teammates at Cornell mocking him and his business, predicting his failure. Despite feeling "hurtful" and "total shit," he silently left, changed elsewhere, and continued with his business. He learned to let the pain subside and stay the course. He explains that if you pursue something unique or take risks, people will notice and judge, especially when you make mistakes. However, "winners aren’t afraid to do a few cringe things now and then," including taking on low-status work; this is the "price you pay for success".

Momentum

The author illustrates the accelerating nature of opportunities with his experience acquiring Somewhere.com. In October 2023, Marshall Haas, the majority owner of Somewhere.com (where the author held a 12.75% minority stake), received an offer to sell 51% of the company at a $47 million valuation. Somewhere.com, a recruiting company, provided "exceptional value" by enabling overseas hiring at 80% less than U.S. wages. The author had invested in April 2022 when the company was small (less than $2 million annual revenue), but by October 2023, it had grown to over 150 employees and $700,000 in monthly profit, tripling in size in twelve months.

Despite the opportunity to sell half his stake for $3 million cash, and the prospect of being forced to sell if Marshall accepted the offer, the author, believing the company could become a $500 million public entity, shocked Marshall by saying, "I don’t want to sell any of my shares, and I would like to be the one to buy the company from you at that price". This initiated the largest deal of his life. Over the next three months, he negotiated to acquire Marshall's stake, recruited and hired a new CEO before closing (to avoid productivity dips), and raised $20 million to fund the deal.

The process was hard and stressful. He worked with a law firm to draft agreements, and due to increasing profits, the valuation was renegotiated to $52 million. He secured an 18% seller note from Marshall for $9.36 million and raised $20.8 million from thirty-eight investors (average check $547,368) in a private equity tranche. This gave him 70% voting shares and full control.

The author highlights this as a demonstration that "Business is all about momentum". His journey progressed from earning $15 per hour moving boxes in his first year, to building a $2.9 million storage facility worth over $10 million in his fifth year, to acquiring $50 million in self-storage and raising $17 million in his tenth year. By his eleventh year, he co-founded RE Cost Seg, a large real estate services firm, and in his twelfth year, he negotiated the $52 million company purchase, raising $20 million and hiring an executive team in forty-one days. He wouldn't have believed his future success if told in 2012, and anticipates even greater opportunities ahead.

The core message is that "If you play this game well, the opportunities come at you faster and get larger in scale". They become more exciting and stressful, with higher stakes, but also more enjoyable. He assures the reader, "You can handle it". He explains that leverage, skills, and network grow over time: after one year, you're better situated; after two, more leverage; after three, new skills; and after four, your network expands, making the "sky’s the limit". Success hinges on "getting in the game and moving quickly. Taking chances. Getting uncomfortable. And seizing opportunities when they present themselves, whether you are ready for them or not".

Start Now

The author identifies a common mistake: new entrepreneurs spend too much time planning for a massive company, dreaming of large deals, and developing advanced business and marketing plans before taking action. He calls this "bullshit". Your primary job, he asserts, is "to collect the money. Period".

His assignment to the reader is practical: "Go out and figure out how to make $500 this weekend" by collecting a deposit, selling a service, or getting cash. He urges them to "Go get sweaty". His rule is that unless you are already wealthy, your first business must generate money immediately, meaning you must "ask for money immediately". If people refuse, it indicates a flawed idea—either there's no problem being solved, or customers don't trust you.

The advice is to start small and boring—mowing grass, moving, or cleaning. The immediate objective is to "make it a full-speed race to make $500 in profit". From that starting point, consistent effort over five years will lead to growing opportunities.

Chapter 3: Not All Businesses Are Created Equal

The author begins with an "inconvenient truth": "Being an entrepreneur is not about you". The market is indifferent to your desires, passions, or what you enjoy or excel at. A "selfish" approach to entrepreneurship, driven by personal fulfillment, leads to poor decisions, clouded judgment, and chasing the wrong things, as one tries to force the world to conform to their preferences rather than accepting reality.

True entrepreneurship, he asserts, is based on "logic and truth". Successful entrepreneurs accept that there are inherently "good businesses and bad businesses". He shares his own experience with both:

Analyzing the two, he concludes that self-storage is "hands down" a fundamentally better business. It required "way less energy and stress and generated way more profit and value"—roughly 10% of the stress for ten times more money per hour invested. While starting it required convincing banks for seven-figure loans and investors for over $400,000, along with the risk of building from the ground up, his five years in the "hard business" of Storage Squad had honed the necessary skills, network, and capital to seize this "good business" opportunity. He emphasizes that one often must start with a "hard business" to acquire the foundational elements before advancing to a "better business".

The Not-Feasible Business

The author immediately dismisses an entire category of businesses, especially for inexperienced and undercapitalized founders, based on three criteria:

  1. Requires venture capital: These businesses are dependent on external funding, which is hard to secure without experience.
  2. New idea, no existing model: Ventures that have "never been done before" are inherently difficult due to a lack of established paths. The author prefers proven models that he can study.
  3. Manufacturing and selling a physical product: This typically involves "insanely capital intensive" processes and is "very difficult to bootstrap" into profitability.

For most people, the odds of success in these areas are "way too low". New ideas often don't exist for a reason—they are too hard. The author stresses that the goal is to maximize chances of earning $30,000 per month with freedom, advising against new ideas or products until this financial baseline is achieved.

How Fun Is This Business?

The author advises a counterintuitive approach to business selection: if your answer to "How fun is this business?" is "very fun," then "forget it". He suggests being an "opportunist," because "The less fun a business is, the more money there is to be made". The ultimate goal is to manage employees and run the business, not to personally perform "fun" tasks. He states that he doesn't care if a business involves "picking up garbage or painting houses in hundred-degree heat"—the "harder the better".

The idea of opening a restaurant, for example, might seem fun, but their profit margins are slim, and up to 90% fail. The same applies to "passion projects": if many people are passionate about a field, it means more "dreamers" are in the competition pool. These passionate individuals are willing to operate unfeasible businesses, even losing money, because they are driven by emotion rather than logic. He warns against competing with people who "think with their hearts".

Industries like gaming, health, and sports are often highly competitive with low profitability for most participants due to a "supply-and-demand equation": a high supply of entrepreneurs makes it harder to find overwhelming demand. While some individuals with specific competitive advantages (e.g., experience managing restaurants or a vast network in sports) might succeed in these "fun" categories, others without such advantages should ignore them.

How Much Status Is Associated with Your Business Idea?

The author advocates for choosing a business with "low status"—one that is "not sexy, exciting, or even a little bit interesting". He emphasizes that what others think of you or your business idea should not matter. He offers a comparison of business ideas based on perceived status:

He suggests a "status test": tell your grandmother (or any older adult) your idea. If they exclaim, "Wow, that is such a good idea!", it means it's likely a "terrible idea"—highly competitive, and no one has successfully won that game before. If they say, "Oh, good for you," it signals a "boring" business that has been done before, thus indicating "much higher" odds of success. The rationale is that low-status businesses attract less competition, as "dreamers will steer clear". He criticizes the "new-idea lens" popularized by shows like Shark Tank, which can make people "delusional". If a business idea hasn't succeeded before, it's often because it's too difficult to make money doing it, so why would you choose to play that game?.

Competition, Profitability, Odds of Success

To further analyze a business model, the author proposes three questions:

  1. "How strong is the competition?"
  2. "What are the profit margins, industry-wide, in a given business?"
  3. "What percentage of people who try to start a business in this field end up succeeding?"

He suggests a "math" equation:

He notes that this assessment is "region dependent," as operator quality can vary by city. Further examples of good and bad businesses include:

The Blue Ocean Strategy

The author addresses the popular "blue ocean strategy," which suggests success comes from creating new markets without competition through innovation. He, however, prefers to start a business in a "red ocean"—an existing industry with competition. His rationale is that a red ocean allows him to study the market, select opportunities, assess existing methods, identify competitive advantages, and learn from competitors.

He acknowledges the common objection: that entrepreneurship should be cutting-edge, and red oceans involve fierce, "shark-eat-shark" competition. He argues this is "more wrong". Many existing companies are "horrifically bad" at basic tasks like answering the phone or fulfilling promises. He notes that many still use fax machines and lack websites but still earn millions. He challenges readers to call home service companies to confirm this: typically, only one in five will answer, and one in twenty will have immediate availability. There's a "massive shortage" of these "old-school businesses" due to weak competition and owners resistant to change. Therefore, he advises pursuing an existing market to ensure demand and profitability.

The Path of Least Resistance

The author criticizes entrepreneurs who are "gluttons for punishment," drawn to the idea of doing hard things and romanticizing entrepreneurship as a struggle against all odds, like a "gladiator" or "Rudy" story. He calls this "bullshit". Business, he states, is a series of games, and "some games are easier to win than others". He uses a basketball analogy: if $30,000 per month is on the line, would you play against LeBron James or a fifth-grade girl? He'd pick the fifth-grade girl every time. This isn't a competition to prove who can do the hardest thing; "The degree of difficulty doesn’t count". In business, "you can get paid really well for doing easy things over and over again, but you can also get paid zero for doing certain hard things really well". It's not an "ultra-endurance workout".

Starting the "next Tesla or Facebook" is likened to playing against LeBron James, while starting a self-storage company is like playing against the fifth-grade girl. The recommended strategy is to "Copy what is working" and emulate what "normal people have succeeded at". Find a niche with "relatively weak" competition, where "average people succeed more often than not"—where six or seven out of ten businesses are profitable, even if the founders aren't exceptionally smart.

He argues against those who believe stronger competition implies greater potential reward, emphasizing that they overlook the odds of success. He illustrates this with a choice: a 70% chance at $30,000 per month profit versus a 0.5% chance of a $50 million exit. He considers the 70% chance "a better deal to take. By far". While he once admired tech titans like Musk, Zuck, Gates, and Jobs, he now realizes that "incredibly rich folks without college degrees who don’t know how to 'reply all' to an email" simply picked the right game with the best odds. This advice, he notes, applies to traditional careers as well.

Think Like an Entrepreneur

The author challenges readers to shift their mindset by observing local businesses. He suggests walking through a downtown area and asking seven questions about every business encountered:

  1. "How does this business make money?"
  2. "Roughly how much money do they make per day, week, and month?"
  3. "How many employees do they have, and what do these employees cost the business each month?"
  4. "How much did it cost to start this business? What’s the minimum amount of money you would need to make it happen?"
  5. "How much rent do they pay for this location, or how much was it to buy this building?"
  6. "How much profit might this business generate for the owner each year?"
  7. "How much headache does the owner deal with, and what is their day-to-day schedule like?"

This requires estimating daily or weekly revenue and expenses. The premise is that if a business has been operating for a while, it is profitable and providing value. Following this, he asks three additional questions:

  1. "How would I run this business more efficiently if I were the owner?"
  2. "How would I create more revenue or reduce costs?"
  3. "What could I do to make this business just a little bit better? What technology could I use, or how could I find a better way to do things?"

This exercise, termed "business curiosity," helps discover "infinite number of opportunities" and discern "good businesses" (profitable, easy to operate, sustainable, simple, leading to good quality of life for owners) from "bad businesses" (painful, low margin, high turnover, complex). It aids in recognizing patterns and identifying suitable opportunities. He recommends discussing these observations with trusted friends to gain new perspectives. This analytical approach is fundamental to how entrepreneurs think.

A common question is why focus on in-person businesses rather than online ones. The author explains that online businesses attract fierce competition, as everyone desires the ability to work from anywhere and achieve unlimited scale. This means global competition, where someone in Asia with 80% lower living costs can directly compete. In contrast, a "real-world business" allows you to choose your market, analyze local conditions, and benefits from geographic barriers to entry. He laments that "Not enough entrepreneurs are willing to look up from their computer screens at the world around them," urging them to "Close your computer and open your eyes!".

Chapter 4: Idea Generation 101

This chapter provides a tactical approach to identifying and evaluating business ideas. To build a successful company, one needs either a market with immense demand or a "competitive advantage," with the author preferring both. A competitive advantage means positioning your service to make customers choose you, by being either cheaper, faster, or better than alternatives.

The goal is to find market gaps where you can excel in at least two of these areas, as it's rarely possible to win in all three. For example, offering the lowest price on the quickest timeline might compromise quality, while great service at a low price might mean longer wait times. The author notes that customers are often willing to pay more for fast, high-quality work. This is the only tactical chapter in the book, requiring "homework" to build and evaluate a list of business ideas, aiming for low-risk, bootstrappable options.

Your Situation and Your Personal Requirements

Before generating ideas, the author stresses the importance of assessing one's personal situation and financial needs. This involves nuanced questions:

These questions help assess your position to "attack" a problem and identify opportunities, keeping competitive advantages in mind.

Build Your List of Ten Potential Businesses

The author recommends using his online list of over two hundred "sweaty startup" ideas (sweatystartup.com/ideas), which align with low-risk, non-fun, in-demand criteria, and combining them with personal ideas. He categorizes opportunities into three levels:

After building a list of ten businesses across these levels, the next step is to narrow them down.

The Ten-Minute Drill

The author describes a "ten-minute drill" to quickly assess a business idea. When a friend wanted to start a house painting company, the author suggested they could quickly determine its viability in their town. He used his iPhone to search "house painting" on Google Maps, then called the top results. One company answered on the second ring, offering to visit and start work immediately; others were similarly eager and competitive on price. One even gave a quote over the phone after looking at his house on Google Maps. In less than ten minutes, they concluded that the house painting market in their town was "saturated" with hungry operators competing heavily on price, making it a "bad opportunity". His friend had spent weeks researching supplies, equipment, and even bought a web domain, but a quick call revealed the market reality.

The lesson is crucial: "Pick up the phone and call your potential competitors". Many fail to do this before investing significant time and money. The author instructs readers to perform this drill for each of their ten business ideas—Google the service, call companies, and gauge their busyness and eagerness to secure business. Based on intuition, eliminate six ideas that are either unrealistic or too competitive.

Narrow It Down

Having narrowed the list to four businesses, the next step is to act as an actual customer and get "actual quotes". This involves creating a spreadsheet tab for each remaining business, listing ten main competitors, and assessing each based on Price, Speed, and Quality.

By recording these data points in a matrix (including columns for Google Reviews, Answer Phone, Good Website, Google Ads), you build a matrix to assess supply and demand and identify market openings. For example, his lawn care company analysis showed a saturated market with $37 per man-hour costs and next-day availability. In contrast, his tree removal analysis showed $400+ per man-hour, two-week availability, and no ad spend (indicating busyness), revealing a clear opportunity despite the high starting cost and danger. This exercise helps develop an instinct for viable businesses, allowing one to quickly calculate rates and profit margins.

Part II: The Skills

Chapter 5: Become an Expert Operator

The author recounts a talk where he asked entrepreneurs about the "hardest business in the world" to run and scale, with the common answer being "Restaurant!". While agreeing that restaurants are brutally hard, he notes countless successful examples, including Texas Roadhouse, which grew from a single Indiana restaurant in 1993 to 627 locations, 91,000 employees, $4.7 billion in revenue, and $730 million in profit in 2023. He describes it as an "operational marvel," handling huge crowds and revenue with immense efficiency.

The key distinction between a struggling mom-and-pop restaurant and a multi-billion dollar chain, both doing the same fundamental business, is "the execution". Success is not determined by the idea but by "The decisions. The hiring and management. The way business is done on a day-to-day basis".

Every Business Is the Same

Many people start businesses based on enjoying a specific activity, such as web development or cooking. However, successful entrepreneurs think differently: "Every single business, when operated at a high level, is fundamentally the same". The owner or CEO of a well-run company is not performing the core service (e.g., flipping burgers, designing websites, operating a chainsaw) but is instead "operating the company".

While initial passion is fine, as a business grows, the manager or owner must perform the same fundamental tasks: selling customers and employees on the vision, solving problems, having uncomfortable conversations about money, hiring, firing, managing, delegating, outperforming competitors, and remaining composed amidst constant problems. Great operators, not necessarily great practitioners of the craft, build the most successful businesses. He contrasts two car repair shops: one run by a competent operator who is an average mechanic, and another by a phenomenal mechanic who is an incompetent operator. The competent operator will thrive, while the passionate mechanic will struggle because they lack the ability to manage, sell, organize, market, and hire.

The author advises focusing on learning to operate, rather than being fixated on a specific business idea. He acknowledges that these operational tasks are "not fun," but excelling at them is what distinguishes successful entrepreneurs from failures. Hard things are crucial for success; an easy life leads to no growth, no additional success, no freedom, and no security. Uncomfortable situations are essential for forging great business operators. Stress is relative, and exposure to discomfort builds the ability to make "cool, calm, effective decisions" amidst uncertainty. He encourages readers to embrace discomfort to open up their world.

Build a Franken Business

The author expresses frustration with college entrepreneurship pitch competitions, where students (with little experience) often propose radically new business models, believing they need to "reinvent the wheel" and "disrupt" industries. He questions why they would completely change existing, profitable industries rather than simply improving existing methods. He argues that "All that matters is making money and building a sustainable company," not conceptual disruption.

He clarifies that he is not against innovation but views it as an evolution of "straight up copying what is working". His own innovation involves combining and adapting successful elements from other businesses, competitors, or different industries—creating a "franken business" from "the best bits and pieces". He reiterates that success comes from building a "boring business based on a proven business model" that leads to wealth, health, and freedom, without extra points for choosing a harder path.

He exemplifies this with Storage Squad: they faced fifteen existing student storage companies. They studied competitors like "Big Red" (which was archaic but profitable) and "Guys and Dollies" (which innovated with free boxes and a small charge for in-room pickup, speeding operations). They also learned from a Boston company that used "hot spots" for box collection. Storage Squad adopted and improved these ideas, for instance, by shrinking the pickup window at hot spots to an exact time, allowing them to load a 24-foot truck with 40+ customers' items in an hour, billing over $10,000. They also implemented "truck swaps" for efficiency.

He admits "Very little about our company was new or unique. Actually, almost everything we did was something we stole from a competitor that had already proved it could work". Their efficiency allowed them to be more profitable, even with similar or lower pricing. Only after establishing a working system did they introduce their own innovations, such as being the first to use Google Sheets for live mobile scheduling, enabling last-minute customer bookings that competitors couldn't handle. The business model wasn't groundbreaking, but by combining proven strategies, they became the biggest and best in the country. The author's advice: don't reinvent the wheel; copy what works, keep it simple, and focus on fundamental execution to carve out your market share.

The Startup, Sacrifice, and Delayed Gratification

Successful entrepreneurs are adept at "delaying gratification," understanding that immediate gratification is impossible. They commit to work today for rewards in the weeks, months, or years ahead, accepting that it requires "sacrifice, boring work, and good decisions compounded for a long time". If it were easy, everyone would be successful.

The author challenges the common misconception, fueled by social media, of achieving perfect work-life balance immediately with a "passive business" that generates high income from minimal work. He bluntly states, "The inconvenient truth is that this is not possible". Starting a business, especially a side gig while holding a full-time job, is "really hard". Entrepreneurs cannot quit their main income until their business model is proven. This necessitates sacrifices: missing dinners, weekends, vacations, and leisure activities. These sacrifices are made in the present for the ability to enjoy more freedom in the future.

He ties this to ambition: the desire to achieve what few others can, to become wealthy, and to take risks on uncertain ventures. Initially, entrepreneurs must trade their time for money, working for $50 to $100 per hour. Once they achieve a comfortable income (e.g., $5,000 per month from twenty hours of work per week), they can quit their jobs and intensify their efforts. This initial "sweaty" work must come from evenings, mornings, vacation days, and weekends. If one is unwilling to make these sacrifices, they "should forget about entrepreneurship".

He notes the naivete of many first-time entrepreneurs who, lacking money, skills, or network, expect to build a million-dollar business overnight. This often leads to repeated failures and eventually returning to a traditional job. He advises starting by trading free time for money, building a foundation slowly, which is less risky, offers significant learning, and results in less costly mistakes.

Entrepreneurship is compared to rolling a snowball down a mountain: the initial accumulation of the snowball is the hardest part, taking time, but once it gains momentum, things become much easier. The key is combining "patience and momentum". He stresses a "long game" perspective, as time tends to "amplify good decisions and good businesses". Success is likely for those who stick with it and do things well for ten years in a game where most persistent players win.

Chapter 6: Sales Is the Foundation of Every Business

The author recalls a pivotal conversation with his mentor, Dan Cohen, who asked if he liked sales. Despite his true feelings, the author knew he was expected to express enthusiasm for it. He admitted he "hated sales," preferring operations, strategy, and vision. Cohen's blunt response was a "bomb": "If you don’t like sales, I suggest you give up now and go get a regular job. You’re wasting your time". Cohen explained that "Life as an entrepreneur is sales," encompassing selling employees on trusting you, partners on collaborating, investors on funding, and even vendors on selling to you.

This revelation shattered the author's prior image of entrepreneurship as strategic planning or problem-solving without direct selling. He felt dejected for weeks but then experienced a paradigm shift, realizing a "secret that only wealthy people understood": "To succeed in this world, you must have the cooperation of other people". This applies to all aspects of life—relationships, friendships, family, and wealth creation—all require interaction and cooperation.

A critical truth is that "You can’t make anyone do anything. People only do things they want to do". Therefore, entrepreneurs must align incentives to create "win-win relationships," ensuring that anyone interacting with them is "better off because of it". The author asserts that "Every single person in this world is selfish," including himself, constantly seeking ways to improve their own lives—whether finding joy in friends, adventure in a spouse, good opportunities in an employer, or increased money with a business partner. People buy services or hire others to solve their problems, which is where a "sweaty startup" fits in.

The "cold hard truth" for sales is "it isn’t about you". No one cares about your wants or problems; they only care about their own. Entrepreneurs, like everyone, can be self-centered and delusional, starting businesses based on personal interests or status concerns, and ignoring conflicting information. However, to succeed in sales and life, one must be "unselfish and focus your energy on other people".

The four fundamental truths of life are presented:

  1. You can’t do it alone.
  2. You can’t make people do anything.
  3. Everyone in this world is selfish.
  4. It isn’t about you.

To achieve desired outcomes, the answer is "Sales". This means selling yourself and your ideas, convincing others that their lives will improve by trusting, working for, or buying from you. It involves understanding their perspective and making it "all about them," thereby selling them on you. The author views his mentor's sales advice as transformative, leading him to successfully "sell" his wife on marriage, his business partner on collaboration, employees on joining, and investors on trusting him. He realized he was "selling 24/7". Ultimately, to build wealth, one must become adept at sales, not for personal gain, but by demonstrating how you benefit others.

The Seven Habits of Highly Effective Salespeople

The author admits he was initially terrible at sales—scared, lacking confidence, uncomfortable asking for money, and uncharismatic. Today, he is a "phenomenal salesperson" due to practice. He asserts that no one is a "natural-born salesperson," but it's a skill acquired through "practice and work". Confidence is paramount; overcoming fear leads to greater success, wealth, happiness, and positive impact. Sales, he notes, is a "self-fulfilling prophecy": believing you are good will lead to improvement.

He outlines seven habits:

  1. Realize Not Everyone Wants to Buy What You’re Selling: You cannot trick anyone. The sales process involves vetting both sides—determining if you're a good fit for them and if they're a good fit for you. Looking for red flags and disqualifying problematic individuals builds trust and makes you appear less desperate and more professional. Gimmicks and manipulation are ineffective in modern business. Do not be pushy or desperate. He recalls a jeweler using old-school, manipulative tactics to sell an engagement ring, which made him leave immediately.
  2. Get Comfortable Being Uncomfortable: Great salespeople earn significant income because they tolerate rejection. Sales is a "numbers game," requiring consistent effort despite frequent "no's". The author has been hung up on, laughed at by investors, and told he'd fail. He emphasizes getting used to rejection and dedicating time to sales daily, like brushing teeth, even when dreading it. His real estate journey began with pervasive rejection from over a hundred investors and ten banks, but he eventually found success through persistence. Over time, confidence grows, and the fear of rejection lessens.
  3. Prove That You Are an Expert: This doesn't mean bragging, but speaking the other person's language and building trust by discussing the risks, difficulties, and problems inherent in any deal. While most salespeople focus on upside, this approach (talking about why business is hard) makes buyers less suspicious. Examples include a self-storage buyer discussing management software details, an investor discussing economic risks, a web developer discussing security pitfalls, and a recruiter discussing hiring managers' blind spots. This demonstrates expertise and positions you as a valuable asset.
  4. Manage Expectations: Stress, according to the author, results from "unmet expectations". While some initial courageous promises are part of business, day-to-day operations should focus on managing expectations. He contrasts two general contractor friends: John, who is excellent at managing expectations by always quoting longer timelines and higher budgets than ideal, is less stressed and earns more. Bill, who overpromises to secure sales, constantly faces stress from unhappy clients and subcontractors. The author states that "One difficult conversation at the beginning of a relationship will save you five even more difficult conversations at the end". Initial pushback from a client signals a potentially problematic relationship later.
  5. Add Value First: A mentor, a wealth manager, provided the author with a ninety-minute financial consultation, offering highly valuable strategies without charge. The mentor's philosophy was to "add[ing] as much value as possible with no expectation in return," trusting that clients would then choose to work with him. The author adopted this, prioritizing adding value and building trust over immediate payment. This principle applies broadly: a CPA friend offers free resources and consultations, and his brother (lawn care) writes how-to articles to attract clients. The process is: Add value -> build trust -> get sales.
  6. Make Scarcity Work for You: After proving expertise, managing expectations, and adding value, the author advises "gently push[ing] your customers away". Instead of a hard sell, discuss reasons why you might not be a good fit, such as being more expensive due to quality focus, being very busy, or only accepting specific customer types. This is not false scarcity if your business is genuinely in high demand and focused on specific clients. Even if you desperately need work, act as if you're busy, as this attitude gains leverage over time. He warns against the mindset of winning every sale, stating that closing 70% of leads means pricing is too low. Losing jobs is beneficial, allowing you to find customers who value your offering and treat you with respect. Avoid "bad customers" who cause headaches and lose money, and be willing to "fire them right away".
  7. Let the Other Party Sell Themselves: At the end of a sales call, the author recommends asking an open-ended question that prompts the other party to explain why you are a good fit for them, such as, "What makes you think I could be a good fit here?" for a tough project, or "Why are you interested in investing in this project?" for an investor. Then, remain silent. This often leads the potential customer to "sell themselves," counteracting their own concerns and reinforcing their desire to work with you. This approach, surprising to prospects, builds trust by demonstrating that you understand the difficulties and are in demand.

Change the Dynamic

The author explains how he applies these sales strategies to secure investor capital for his real estate deals, having raised over $50 million. His aim is not just to close a deal but to build trust and ensure a good partnership. He begins by proving his expertise and operational superiority in storage. Then, he "turn[s] it around" by openly discussing risks, such as real estate cycles, interest rates, and external factors that affect property values and debt. He outlines his plan to navigate difficult environments, showing his selectivity in choosing partners and properties. This process establishes him as an expert, manages expectations, vets potential partners, and creates scarcity.

He employs a "bomb" question: a hypothetical scenario where an investor's $100,000 investment faces rising interest rates, slowed rentals, missed projections, and a real estate recession, potentially resulting in subpar returns and being stuck in an illiquid investment for ten years. After presenting this grim scenario, he falls silent. Surprisingly, most prospects then begin to "sell themselves" on the investment, counteracting his warnings with their own reasons for its value. This shifts the dynamic, making them the salesperson. Investors appreciate his honesty and awareness of risks, trusting him to protect their downside. He uses a similar technique when interviewing management candidates, outlining the demanding nature of the work (e.g., sixty-hour weeks, startup mentality, rapid change) before asking why they are still interested. Strong candidates become more excited, while unsuitable ones reveal themselves.

The author challenges the reader to frame their own sales pitch using this structure, identifying how to prove expertise, list potential risks, vet prospects, add value, manage expectations, and create scarcity to prompt prospects to sell themselves. He adds two crucial notes: first, to record sales interactions for analysis, like athletes review game tape, as this is a key way to improve over time. Second, always "ask for the business" directly at the end of the process; do not be passive when it's time to close the deal.

Marketing

After securing initial sales and gaining confidence, the challenge becomes finding more customers beyond one's immediate network. The author advocates for "guerrilla marketing" over traditional methods like paid ads, branding, or commercials, which are usually out of reach for new entrepreneurs. The "cold hard truth" for early-stage businesses is that "you must do the things that do not scale".

He explains that his company did not spend money on mainstream marketing until 2017, six years in, when they were generating over $2 million in annual revenue. Before that, they relied on scrappy, unscalable methods:

Other examples of guerrilla marketing:

The author emphasizes that conventional marketing wisdom is often irrelevant for small businesses. What truly works is "Figuring out where your customers are and getting in front of them in unscalable, common, sweaty ways". He could easily get in front of his target customers (college students) on campus. Most people, he notes, are unwilling to do this hard work because they fear rejection, preferring to spend money on online ads instead of engaging in direct, uncomfortable methods like managing door-to-door teams or using sidewalk chalk. However, he asserts that if you are willing to do what competitors are not, you can "grow your business beyond your wildest dreams".

Chapter 7: Life Is Short

The author acknowledges that individuals start life with different advantages regarding money and network—some are born into entrepreneurial families with established businesses, gaining exposure to operations, hiring, and investing from a young age. This provides a "huge advantage" and a safety net. He believes an entrepreneurial mindset is arguably even more crucial than starting capital. His own children, he notes, are ten times more likely to become entrepreneurs due to their household's culture.

However, one resource is distributed equally: "Time". Every human, regardless of success or disadvantage, has precisely twenty-four hours in a292].

The Scarcity Mindset

The author generally operates with an "abundance mindset" in most areas of life, believing that opportunities for others also create opportunities for him, and that others' success promotes his own. He believes in sharing freely to foster synergies and that there is an "infinite amount of money" to be made. However, he holds a different perspective on time, adopting an "extreme scarcity mindset".

He questions why people guard their money but freely give away their time. For example, few would give a neighbor $100 for beer, but many will politely listen for thirty minutes to someone they don't care about, effectively losing 35% of their family time that day. He advises adjusting one's mindset about time: days and weeks pass quickly, and without deliberate action, ten years can fly by, leaving one stuck in a dead-end job with unmotivated people, missing opportunities to take risks. Losing $250,000 on a failed business stings, but money can be earned back; time cannot. He emphasizes being "very thoughtful" about how time is invested.

Work on the Right Things

The author observes that most entrepreneurs fail to truly "own a company" and instead "end up owning a job". They are perpetually busy servicing customers, putting out fires, and trading their time for money. This isn't due to a lack of intelligence or hard work, nor typically the wrong business model. Rather, "They simply do not work on the right things". They prioritize urgent, immediate tasks over "important for the long-term growth of99, 300]. The author argues that many pizza restaurant owners don't personally make pizzas or intervene constantly, as a manager could handle staff for less pay. His friend's stress stems from focusing on "urgent and important things" instead of "important things that aren’t urgent".

The Four Quadrants of Time Management

The author introduces a matrix for time management, categorizing activities by importance and urgency:

He provides an example of a poop-scooping business owner whose clunky website form was losing potential customers. By spending thirty hours revamping the form with clear text and a "get a quote" button, customer leads doubled overnight, and the company doubled in size within two years. This seemingly small decision was part of the 20% effort that generated 80% of his growth.

This principle also applies to customer relationships: 20% of customers will cause 80% of headaches, and a different 20% will generate 80% of profit. Recognizing this distinction is key to building a great business [314. Mark which activities are potential 20% high-leverage activities. 3. Categorize each activity by quadrant (important/urgent, urgent/not important, not important/not urgent) and consider if any can be eliminated. 4. Adjust your schedule to prioritize the 20% and Quadrant 2 activities.

The author performs this exercise annually, acknowledging that in the "weeds" of business, it's easy to overlook important tasks and defer hard decisions. He insists on accountability for this analysis, as "What gets measured is more likely to improve".

Do Things Today That Will Reward You Seventy Years Down the Road

The author compares entrepreneurship to an "adult marshmallow test," where most people lack wealth because they are unwilling to exchange "short-term loss for long-term gain". They prioritize immediate gratification over decisions that would yield results five to ten years in the future. The media often misrepresents entrepreneurship as a "get-rich-quick scheme," celebrating rare unicorn stories of rapid success, but in reality, it's the, connect with capital, buy his first apartment building at thirty, and build his firm over twelve years.

This illustrates a "multigenerational game" of wealth building. Immigrant ancestors work hard for their children's opportunities; those children take professional or blue-collar jobs, creating stability for their own children, who then leverage that safety net to become entrepreneurs and accumulate greater wealth. The lesson is to "Play the long game". Building wealth is a process requiring years of "suffering" through "hard and boring things" for significant results. While others seek immediate enjoyment, successful individuals make decisions to maximize future enjoyment. Consistently improving over years prepares you to capitalize on larger, more profitable opportunities.

Entrepreneurship can feel like slow progress for weeks, months, or years, but then "in a matter of weeks, it can all come together," with rapid growth and momentum. There are "sprints" when opportunities arise, requiring intense, short-term effort, but these are followed by a return to the "monotonous grind" of doing the right things consistently.

He compares the entrepreneur to a lion in the Sahara: mostly "lying on a rock," grinding through boring tasks, but occasionally sprinting to chase a "gazelle"—a significant opportunity—to "kill it, and bring it back for everyone to eat". These "hunting" days are rare; the majority of time is spent enduring the "boring stuff" to ensure the company survives for when opportunities appear.

Chapter 8: Get Your Shit Together

The author recounts a chaotic period at Storage Squad in Boston during the spring 2013 season. Their guerrilla marketing efforts using sidewalk chalk and flyers had worked to work from 4 AM to 8 AM before loading trucks. Upon sending the initial schedule to 700 customers, he immediately received over 200 change requests. The biggest problem was staffing: he needed ten full-time employees for September 1-3, but only had eight on the first day.

The author, his partner, and his partner's brother personally drove trucks and made deliveries alone. The author describes a brutal day, driving a box truck, answering calls, and hand-delivering boxes up multiple flights of stairs, enduring physical pain, chafing, bleeding, and a fever. After three days without sleep, he continued scheduling and loading trucks. His team was exhausted, tips were low due to poor scheduling, and some employees quit. He recalls the dedicated employees who persisted.

On the third day, an employee called to report hitting a parked BMW with a box truck, totaling it. This was on top of previous incidents: one employee put gasoline in a diesel engine ($5,000+ repair, no insurance) and another hit an overhang, ripping the truck's top off (also uninsured). The BMW claim was on his personal insurance because they hadn't secured business coverage yet. While processing this, his partner called to report another employee had quit, abandoning a full truck with boxes for twenty-five customers, two hours behind schedule.

Overwhelmed, ignoring constant customer calls, the author experienced a full-blown anxiety attack, weeping and feeling "out of control". He called his mom, wanting to return home, and described "harder man with a new perspective".

He notes that every business or hobby is initially fun due to rapid progress and early successes, but then comes the "grueling work". Success is difficult, otherwise, the world would be full of happy, rich business owners. Stress, fear, and discomfort are unavoidable parts of business and life. The world is indifferent to feelings, and bad things happen even to great operators. Entrepreneurship involves gambling, requiring comfort with risk. The "cold hard truth" is a "direct correlation between the stress you have endured in your professional life and the amount of money you earn today". Stress is normal and makes you stronger; the only way to succeed is to push through and accept it. The author thrives under pressure and encourages readers to embrace the challenge.

Lose the Victim Mentality

The author argues that media, especially social media, fosters a victim mentality by portraying the world as constantly worsening, with pervasive suffering, danger, injustice, pollution, and lack of opportunity. He insists, "None of that is trueIt isn’t their fault... It is hard out there! The world is a bad place... Our careers are an uphill battle, and entrepreneurship is impossible".

The "cold hard truth" is: "You are not a victim". Your current situation—your relationships, income, health, assets, and network—is a "direct result of your decisions and your actions in the past". He emphasizes that "It isn’t anyone else’s fault" and successful people "take ownership in every situation". Cultivating resilience and they should have bought an operational one. While Storage Squad was successful, they recognized its limitations in market size, stress levels, and revenue potential for a large, scalable business. Despite learning invaluable lessons in operations, management, and delegation, they had not yet mastered uncomfortable conversations.

He initially calculated a $1.9 million construction budget for the facility and prepared a 120-page package. The first ten banks rejected them, but the eleventh, Tompkins Trust Company, lent $1.5 million. He then approached over a hundred potential investors, with ninety-five turning him down. Five said yes, including his father and real estate agent Steve. Steve's check arrived just in time to make a $100,000 payment to their earthwork contractor, days before the author's wedding in June 2016.

By January 2017, they faced a "big problem": they were over budget by more than 25% ($500,000). Winter concrete pouring required expensive heating, and a delay in ordering steel cost $50,000 they received their certificate of occupancy, and students immediately began moving in. The development ultimately cost $2.4 million, leaving the author feeling "like a broken man". Five years later, he and his partner bought out their investors at an $8 million valuation. He later learned his father had taken out a mortgage on his childhood home for the initial $125,000 investment—information he's glad he didn't have at the time. His father's investment, bought out for $520,000 in 2022, became a significant part of his net worth.

The "cold hard truth" is: "One difficult conversation at the beginning of an endeavor or relationship will save you ten hard conversations later" and reduce stress. Many avoid telling others unpleasant truths, leading to impossible deadlines and future difficulties. Customers can be demanding and unrealistic, and business owners often make matters worse by agreeing to unreasonable demands or pretending things are fine. Entrepreneurs must have the "courage to stand up for yourself and keep this from happening" and " the worst result of this scenario? What happens next?" This involves following the worst-case to its logical conclusion. His answers include having skills, knowing bankruptcy isn't permanent in America, having a loving and supportive family, parents' spare bedrooms, not going hungry, ability to get a W-2 job ($200,000+), and bootstrapping a new business, emerging stronger.

He reflects that if he had done this exercise during his Boston anxiety attack, the worst-case scenario would have involved unhappy customers, $100,000 in refunds, delayed deliveries, negative reviews, and potential business shutdown, or needing to find a less stressful business or a job. However, he would still be himself, not bankrupt, not unemployable, not in jail, and his family would still love him and have a place for him.

Fear is real, and identities are tied to businesses and careers, making failure feel shameful. However, most situations are far less dire. He gives an example of being stressed about a difficult conversation with a friend-employee who wasn't performing.

Be Resourceful

The author asserts that in entrepreneurship, there are "no answers," only "options". Every decision presents multiple paths, leading to various outcomes, many beyond one's control; luck plays a significant role, as does decision-making. Ultimately, success boils down to "resourcefulness".

He contrasts this with the high school perception of life as a textbook, where every problem has a right or wrong answer. Business, like life, is "emotional and dynamic". You don't need to get every decision right; getting the "big stuff right" allows for error in half your decisions and still winning. The key is to "put yourself out there and practice".

Part III People

Chapter 9: The Attributes of Winners

The author emphasizes that people are the ultimate form of leverage in entrepreneurship. He shares his personal experience of transforming his real estate company from one where he was the bottleneck, making every decision and handling every detail, to one where a team managed a $9 million deal without his direct involvement. This shift was possible due to good people in the right seats with the right processes.

The author states that his companies employ over 300 people and generate more than $30 million in annual revenue, and he has raised capital from over 250 individuals. He has convinced over 30 people in management roles to leave their jobs to work with him. He prides himself on retaining key employees for many years by setting them up for success, managing expectations, being honest, respectful, and not being greedy.

He acknowledges that dealing with people is hard, unpredictable, and emotional, and it doesn't come naturally to everyone. However, he asserts that if one can "unlock and master the art of dealing with people," they will be able to build companies and become wealthy.

The author outlines five types of people you want on your team, emphasizing that a company is only as strong as its hires:

  1. People with an Abundance Mindset People with an abundance mindset believe that others' success contributes to their own, rather than seeing success as a zero-sum game. They are eager to help others and celebrate success. The author stresses running away from people with a scarcity mindset, who believe that if someone else makes a dollar, it's a dollar they can't make themselves.
  2. People with a Sense of Urgency These individuals act quickly, defaulting to action and understanding that business is a race. They are willing to move fast even with incomplete systems or uncertain plans, which is a must-have trait for early-stage companies, as speed is a small business's only advantage against larger competitors. This trait cannot be taught.
  3. People Who Are Not Afraid to Stand Up to You and Call You Out Leaders should surround themselves with smart people who think critically and are willing to disagree. While this can be difficult and ego-challenging for a leader, it is invaluable. The author gives an example of how his VP of Finance, Kevin, saved them from making risky real estate deals by challenging his optimistic views.
  4. People Who Make Good Decisions The author admits he often overestimated people's decision-making abilities early in his career and tolerated low performance for too long. While not everyone in a company needs to be a decision-maker, it's crucial to find good decision-makers for management and higher-skilled roles by observing their decisions and reasoning.
  5. People Who Aren't Afraid to Get Their Hands Dirty and Do the Work These are the people who will "grind and do the work necessary with a positive attitude". The author warns against "messengers" who merely pass information without solving problems or taking action, common in middle management in large organizations. He emphasizes that leaders must be willing to get their own hands dirty, which encourages their team to do the same.

The author also lists "deal-breakers" – behaviors that are unacceptable in his company and circle:

Chapter 10: How to Find High-Performing People

The author challenges the conventional wisdom that "who you know" is key to networking, stating that it's actually about "who knows you and what you know how to do". He argues that traditional networking with a "me, me, me" attitude is ineffective because people are inherently selfish and look for win-win scenarios where they benefit.

The "inconvenient news" is that one must do the work and get good at something before their network will truly grow. This means building, becoming an expert, developing skills, making money, and learning to operate a business. By becoming someone who can help others, others are more likely to help you.

He emphasizes "Always. Be. Recruiting." (ABR) as a core principle for entrepreneurs. Great entrepreneurs are constantly hunting for talented people, observing individuals in everyday life (e.g., at family gatherings, restaurants, golf courses, or buying from vendors) and subtly selling them on opportunities.

The author proposes a "theory on recruiting":

He provides examples of recruiting talented individuals by offering them more flexibility, control, excitement, or money with less travel. He also shares a personal story of recruiting a highly motivated Walmart employee who showed urgency and initiative not typically seen in his role, by simply observing and offering him a better opportunity. He encourages entrepreneurs to look for such traits in everyday interactions (e.g., hotel counter staff, bartenders, Target employees).

Regarding friends and family, the author challenges the conventional wisdom of never hiring them. He argues that trust is built-in with family members, and you can observe their habits, thought processes, and moral compass in advance. He has hired more than ten people from his direct network, including his uncle, friends, and cousins. He states that if you are an excellent communicator and manage expectations properly, it can work well, even if it means having difficult conversations or parting ways without hard feelings. He prides himself on never having a falling-out with friends or family he has fired.

He shares an example of how he recruited a third-grade teacher, recognizing her organizational and communication skills, for an operations role in his real estate company. She was offered a higher salary and remote work, proving to be a "phenomenal asset".

The chapter concludes with an assignment: list the skills needed for your company, identify where people with those skills currently work, and then strategize how to approach and recruit them by offering what they don't have in their current roles.

Chapter 11: Hiring—The Key to Ultimate Leverage

The author admits that one of his repeated mistakes has been waiting too long to hire for critical positions. He advises hiring when you are spending too much time on tasks that could be done by others (e.g., $20-an-hour work) or when you become a bottleneck to growth.

He identifies three types of hires:

He suggests that the first hire should typically be an administrator or technician to free up the owner's time for high-level work. He illustrates this with a friend who hired a virtual administrative assistant from the Philippines for $800/month, allowing her to bill more hours as a sales consultant and work less.

The author recounts his first entrepreneurial experience at age 13, mowing lawns for his father's boss, and then hiring his first employee at 14. This early experience taught him about profitability, as he was making over $40 an hour after expenses by age 14.

A rule of thumb for hiring: you should be able to bill a customer two to three times what you pay an employee to maintain healthy margins, accounting for employment taxes, benefits, overhead, and lost time. He provides a spreadsheet at sweatystartup.com/wages for users to calculate their required charging rates.

The author shares his "big secret" for low-risk hiring: hiring overseas employees. About 80% of his 300+ employees are from Latin America, South Africa, Eastern Europe, and the Philippines, and he pays them about 80% less than U.S. employees ($800/month or less than $4.60/hour for starting wages). He argues that this is not anti-American because Americans desire low-cost goods and there aren't enough Americans willing to do certain jobs. This allows him to staff his private equity company with 45 employees for $1.3 million/year, compared to competitors spending over $4 million. He also hires high-level employees (managers, financial analysts, software engineers) from these regions for significantly less than U.S. salaries (e.g., $1,500/month for roles that would cost over $100,000 in the U.S.). He uses his own recruiting company, Somewhere.com, to find this talent.

Alignment is critical in hiring. The author asks candidates to describe their "ideal world" five years from now to understand their true motivations and ensure a good fit. He emphasizes that the company must be able to deliver what the employee wants for them to be happy and fulfilled.

Finally, the author discusses what competent people want in a work environment to reduce turnover:

  1. Structure Is Good: Contrary to popular belief, employees (even high performers) prefer structure, clear solutions, and benchmarks over ambiguity and chaos. Entrepreneurs, who thrive on uncertainty, often mistakenly assume others do too.
  2. Make Decisions and Changes Quickly: High performers become frustrated when their ideas for improvement are ignored or decisions are delayed. Not taking action when a team knows a better way leads to resentment and turnover.
  3. Surround Your A Players with A Players: Tolerating "C players" (incompetent or low-performing employees) makes "A players" miserable, as they end up picking up the slack. The author emphasizes that "Your company’s performance will fall to the level of incompetence that you tolerate," and advises firing low performers quickly to prevent high performers from leaving. He believes "people do not change" and should not be kept in roles they can't do well. A company is a "sports team," not a family, and non-producing members need to be cut. The author acknowledges that firing is difficult and emotional but necessary, advising to deliver the news directly, offer generous severance, and help them find a better fit.

He shares a story where he swallowed his pride and hired a candidate who initially declined an offer but later returned, proving to be one of their best hires, illustrating that hiring is "messy and complicated" and sometimes taking a chance on people pays off.

Chapter 12: Management and Delegation

Effective management and delegation involve empowering employees to solve problems themselves rather than taking over. The author uses the "monkey on the back" analogy: when an employee brings a problem (their "monkey"), the manager should ask "What would you do and why?" to teach critical thinking and ensure the employee leaves with their own monkey and a plan. If the manager keeps the monkey, they become the bottleneck, leading to stress and slow progress. By teaching employees to care for their own "monkeys," they become better at problem-solving, and managers learn which employees are competent decision-makers for future promotions.

The author distinguishes between two levels of delegation:

  1. Delegating Tasks: This is the first phase, where employees perform repeatable actions without making decisions. It's scary initially because the owner can do it better, and mistakes will occur, but it buys back time and is the first form of time leverage. A large, profitable business can be run with only task delegation, but the owner will eventually become a bottleneck as all decisions and problems still come to them.
  2. Delegating Decisions: This is the key to truly scaling a company beyond the founder. It involves empowering employees to quote jobs, sign contracts, make hiring decisions, negotiate, and solve problems. The author recounts a breakthrough moment when his manager solved an employee abandonment issue without his intervention, freeing him from being the bottleneck.

He introduces a delegation framework: "My job. Our job. Your job.". First, it's my job to ensure the employee can do the job efficiently and perfectly. Then, it's our job (the manager's and employee's) to work together, with coaching, hand-holding, and feedback, which can take weeks or months. Finally, when the manager is confident, it becomes your job (the employee's). Continuous monitoring and accountability are crucial to prevent employees from slipping into easier ways.

The author stresses the importance of clear and concise communication in delegation, as people have short attention spans. He advises:

He explains that getting out of the weeds (doing urgent but not important $20-an-hour work) is essential for growth. His early experience with Storage Squad forced him and his partner to delegate and focus on "big stuff" like schedules, staffing, and growth. Being stuck in the weeds prevents entrepreneurs from seeing the big picture, missing warning signs, market shifts, and competitor innovations.

The chapter concludes with a challenge to identify an urgent but not important task and delegate it to make space for higher-leverage activities, noting that the relationship with one's business and its bottlenecks will change over time.

Chapter 13: What Is This All About?

This chapter delves into the broader purpose of entrepreneurship and wealth, emphasizing that it's ultimately about freedom – the freedom to do what you want, when you want. While the book focuses on making money, the author highlights that financial success is only one part of a well-rounded and balanced life, which also includes fitness, mental health, and relationships with friends, spouse, and children.

He offers several pieces of advice beyond business:

Conclusion

The author concludes by emphasizing that nobody gave him permission to get rich or pursue his ventures in real estate and other businesses. He had no traditional qualifications or industry background, yet he built a real estate private equity firm controlling over $150 million in assets and stakes in other growing companies. He argues that aspiring entrepreneurs should not wait for traditional validation or external permission.

He dismisses common insecurities like "I’m not qualified" or "I don’t have any experience," stating that there's no textbook with all the answers in entrepreneurship; you figure things out as you go. Successful people attack problems and go after opportunities they aren't qualified for, giving themselves permission.

The author acknowledges impostor syndrome as a common feeling, even for highly successful individuals like LeBron James or Elon Musk. He describes it as an illogical "lizard brain" voice that tells you to run from danger and doubt your abilities. He notes that people generally care less about you than you think, and if they do care, it's because they have something to gain.

To overcome impostor syndrome, one must acquire the network, skills, and capital, and crucially, practice. By repeatedly putting oneself in difficult situations, one can train themselves to love the pressure and potential for failure.

The book ends with a mantra for success in "boring things":