He Slept With Cockroaches... Now He Makes $40 Million/Yr | Edwin Arroyave

Edwin described himself as a nine-figure CEO whose businesses have generated more than $600 million over roughly 25 years. The conversation revisited his path from extreme childhood poverty and a first call-center job to building large home-security and solar businesses.

The interview was conducted by the School of Hard Knocks team, including James and co-founders Jack and Josh, at Edwin’s home in California. They noted that they had first interviewed him in 2023, nearly two years earlier.

The School of Hard Knocks audience had grown sharply since the earlier interview. The conversation referenced growth from roughly 500,000 followers to 5 million on one audience measure and about 12 million across social platforms.

Edwin was born in Bogotá, Colombia, and immigrated to the United States with his parents when he was six. His family came seeking the American dream but later lost virtually everything.

By age 15, Edwin said he had effectively become the head of his household. His mother struggled to pay rent, the family sometimes ran out of food stamps before month-end, he shared a tiny windowless bedroom with his siblings, and roaches woke him during the night.

He said the immediate driver behind his early ambition was not comfort but the desire to escape severe hardship. He described the avoidance of pain as the force that pushed him to attempt things that felt beyond his confidence or perceived worth.

At around 12, Edwin had already fixed on earning $100,000 a year by age 21. He spent hours alone imagining that future even though he had no idea how he would achieve it.

His financial ambitions were tied strongly to promises he wanted to fulfill for his parents. Money represented the ability to change their circumstances rather than merely a numerical goal.

Edwin said his mother was central to the faith and confidence he developed as a child. She prayed over him every morning and night, repeatedly told him he was born to do something great, and told him future success would give him a platform to speak about his faith.

His father had been incarcerated, and Edwin promised him that once he got out, he would never need to work again. Edwin specifically wanted to keep him from returning to the industry that had led to his imprisonment.

He separately promised his mother that he would eventually buy her a dream house. Those promises became part of the “why” that he says pushed him past his own perceived limitations.

Edwin took a call-center job at 15 despite being intensely shy and timid. Sales was an uncomfortable fit for his personality, but his family’s financial situation made avoiding the challenge less important than earning money.

Getting that first job was itself difficult because Edwin became extremely nervous during interviews. He said he attended about 16 interviews, would sweat heavily from anxiety, and repeatedly failed to get hired.

A school friend eventually directed him to a call center that supposedly hired almost anyone, but Edwin was initially rejected there too. During the interview he became so nervous that the interviewer gave him paper towels for his sweating.

After that rejection, Edwin went into a restroom, washed his face and prayed for an opportunity to help his family. He said he promised God that if he received a chance, he would work harder than anyone and continue praising God.

Immediately afterward, a man at the company encountered Edwin, learned he had been rejected, and took him to HR with instructions to hire him. Edwin said that same man later helped him start his security company approximately six years later, making the encounter one of the formative events in his life.

The experience produced Edwin’s belief that people sometimes need one person willing to give them a genuine chance. He argues that a useful mentor is someone who teaches patiently, understands the business and has a vested interest in the learner’s success.

Edwin still experiences the physical effects of nervousness despite his later success and public profile. He said he can sweat heavily, stutter and become extremely anxious, and once escaped a red-carpet situation by going to the restroom before the sweating became visible.

His preference for black clothing during interviews and public appearances is partly connected to that anxiety. He said he avoids white shirts because he still worries that nervous sweating could become visible.

Edwin says preparation, rather than natural ease, became the foundation of his confidence. His story is explicitly not that he transformed into someone naturally comfortable “winging it”; he built systems that allowed him to perform despite that weakness.

He turned his $100,000-by-21 dream into intermediate targets rather than treating it as one distant goal. He reasoned that he first needed to become a manager by 18 and expected that position to produce roughly $60,000 a year.

Edwin became the youngest manager in the call center’s history at 18 and was earning about $60,000 annually. Reaching that target made the previously distant $100,000 goal feel plausible to him.

He credits consistent performance on unglamorous work with helping him overtake colleagues he regarded as more talented. He showed up every day, attended role-playing sessions and leadership-development classes that top salespeople sometimes skipped, and concentrated on the activity and attitude he could control.

The call center provided approximately an hour of leadership-development training each day before employees went on the phones. Edwin worked there from about 15 to 21 and later said that education, apart from his faith, was one of the biggest foundations of his success.

A major breakthrough came when Edwin asked the company’s top salesperson to record his pitch on a Radio Shack recorder. Edwin transcribed it, memorized it word for word, repeatedly studied it and copied the salesperson’s tonality and delivery.

He deliberately modeled the best salesperson rather than trying to invent his own approach immediately. Edwin compared the strategy to Kobe Bryant studying Michael Jordan: copy the best closely enough to develop the underlying skill.

As he began sounding and behaving like the top performer, Edwin said his own belief rose dramatically. He eventually became one of the company’s strongest performers and later the manager.

He also became the right-hand person to the vice president of sales. Being close to someone operating at a higher level expanded what Edwin considered possible for himself.

Edwin’s broader theory is that accomplishment changes identity by giving the mind evidence that a larger result is possible. He says big dreams matter, but hitting smaller targets along the way progressively raises self-belief.

He repeatedly argued that people will not consistently outperform what they believe they deserve. In his language, a person cannot “out-earn” their self-worth for long, making identity-building as important as technical skill.

His recommended way to build self-belief is to enter situations that demand more than a person currently thinks they are capable of and then succeed inside them. He sees each successful exposure as evidence that updates the person’s identity.

Edwin believes self-trust is also built by keeping promises made to oneself. He argued that repeatedly breaking private commitments teaches the subconscious not to believe future declarations, while accumulating small wins creates confidence.

He therefore added an important qualification to deliberately creating pressure: pressure works best when a person has already built a record of following through. Simply taking large risks without disciplined follow-through is not the strategy he was advocating.

He framed purpose as something that must continually be renewed after major goals are achieved. Without a new game or challenge, he believes successful people become comfortable and stop progressing.

For Edwin, the “why” matters more initially than the what, when, where or how. His first major why was his parents; later motivations included the lifestyle he imagined and larger spiritual or leadership goals.

His early material dreams included owning a home in the Hollywood Hills and a house on the beach. He said he eventually came to live much of the lifestyle he had imagined while poor.

The income opportunity Edwin chose after the call center was door-to-door home-security sales. He did not want to knock doors, but he believed the opportunity could generate the money required to fulfill his larger goals.

Edwin left a job paying roughly $70,000 a year to pursue the home-security opportunity, although he initially tried to keep both jobs. He worked the call center roughly 7 a.m. to 3 p.m. and his own business from about 4 p.m. to 10 p.m.

For his first 10 days selling security door to door, Edwin made no sales. He remained in the opportunity partly because his brother-in-law was closing about two sales per day, proving to him that the model could work.

He concluded that retaining the call-center income was reducing his urgency. He was still making about $1,500 a week there, which allowed him to approach his new business without fully mastering it.

Edwin eventually resigned completely from the call center—his version of “burning the boats.” Once the safety net disappeared, he said his urgency changed immediately.

After going all-in, he learned the sales presentation and objections essentially verbatim in a day. He also learned the paperwork and operational details until the process became reflexive rather than something he had to consciously think through.

His first day after that preparation produced five sales and about $1,500 in income. He had effectively earned in one day what he previously earned in a week while working roughly 70 hours.

That first strong week produced approximately 12 sales and around $7,000. The result radically expanded what Edwin believed the opportunity could become.

Edwin admits that early arrogance contributed to his initial door-to-door failure. Because he had been successful at the call center, he assumed he would automatically succeed in the new environment and initially failed to study the material seriously.

His lesson was that previous success does not substitute for mastering a new craft. Once he knew the presentation, rebuttals and process reflexively, his performance changed.

Immediately after making roughly $7,000 that week, Edwin visited an open house connected to his goal of buying his mother a home. He converted the dream into a concrete target of purchasing the house within 90 days.

He bought a minivan before he had enough salespeople to fill it. Edwin saw the purchase as action taken ahead of certainty: because he now owned the van, he created pressure on himself to recruit a team.

He used similar “touch the dream” tactics personally, such as staying briefly in expensive hotels before he could afford his eventual homes. Exposure to those environments made his desired lifestyle more concrete and, in his view, gave him another reason to work.

At 21, he also remembers feeling intimidated entering a Mercedes dealership because he feared he did not belong. Successfully entering environments that had previously intimidated him gradually weakened that belief.

Edwin believes strategic rewards can increase motivation rather than merely consume money. He would work hard and then give himself a limited taste of the lifestyle he wanted so the reward reinforced why he was working.

The interviewers summarized part of the entrepreneurial lesson as “sell it first and then figure it out.” Their argument was that securing a real customer creates urgency and forces execution that endless preparation often avoids.

Edwin agreed that obsessing over “how” can kill action, calling the how “the killer of all dreams.” His sequence is to become clear about the why, find an appropriate opportunity and then solve the details through action.

He reduced his early success formula to two practical requirements: an opportunity capable of producing the desired income and a person who has already succeeded and has a vested interest in helping you. He regarded finding the second person as the harder part.

Once those two conditions exist, Edwin believes consistency, discipline, work ethic and time become the primary variables the individual controls. He stressed that successful people also make wrong decisions; their advantage is continuing until they solve them rather than quitting after the first failure.

Edwin strongly associates uncertainty with faith. He said that continually choosing only outcomes one knows will succeed removes the circumstances in which he personally feels most dependent on God.

His recurring formulation was that larger dreams inevitably create larger problems. Rather than interpreting difficulty as evidence that the dream is wrong, he views challenge as part of the mechanism through which growth occurs.

He described people as consisting of spirit, soul and body, with the soul encompassing mind, emotions and will. Within his religious framework, he believes negative thinking and uncontrolled emotion are attacks on that inner domain and need to be deliberately managed.

Edwin said people tend to overthink negative possibilities far more than positive ones. His preferred response is to redirect attention toward purpose, faith and what can actually be controlled.

His sales philosophy centers heavily on certainty. He believes the more certain person tends to influence the less certain person, making the salesperson’s internal conviction a critical part of persuasion.

Edwin asserted that persuasion is predominantly nonverbal, describing it as roughly 45% tonality, 45% body language and 10% the actual words. The practical lesson he drew was that the seller’s emotional state—confidence or fear—gets communicated to the prospect.

He therefore does not view memorization as making a salesperson robotic. His process is to write the presentation, memorize it, internalize it and finally personalize it until the material becomes natural enough that attention can shift to the customer, body language and delivery.

Edwin said even his approximately 45-minute stage presentations are extensively memorized. Preparation allows him to improvise around a known structure rather than depend on spontaneous performance.

He contrasted his own approach with his wife, whom he described as naturally good at winging things. Edwin said he has never had that gift and needed preparation to reach a similar level of confidence.

The home-security business ultimately expanded far beyond its initial operation. Edwin described going from one state to more than 36 states, from about 20 installers to more than 200, and from roughly 15 sales representatives toward approximately 500.

He said he did not know in advance how any of those jumps would happen. His strategy was to focus on his strengths, act before every resource was available and recruit people whose abilities covered areas where he lacked expertise.

Edwin identifies selling, influence, recruiting, simplifying complex material, training and leadership as his primary business strengths. He said his own difficulty understanding complicated material forced him to simplify it, which later made him good at teaching others.

Neither of Edwin’s parents was an entrepreneur. His entrepreneurial skills were developed through work, mentors, repeated sales practice and the environments he entered rather than inherited business experience.

Skyline took roughly 17 years to reach $40 million in annual sales, while Edwin’s later solar business reached approximately $40 million in its first year. He rejected the idea that the solar result was truly a one-year success, arguing that it rested on the capabilities developed during the previous 17 years.

His explanation for apparently rapid later success is accumulated business “muscle.” Years of recruiting, selling, training, leadership and surviving setbacks allowed him to solve harder problems faster when entering solar.

Edwin estimated that over approximately 25 years in business he had experienced around five major setbacks severe enough to feel like potential knockouts. Each recovery, he said, made the next crisis easier to withstand.

He considers resilience one of the most important qualities for sustaining a business over decades. His view is that business does not become easier as a person succeeds; the problems become harder while the operator becomes more capable.

The move into solar became practical only after Skyline had developed enough scale and executive talent. Edwin was already paying high-level executives and realized their expertise could support another company rather than being limited to home security.

Solar also resembled the security business operationally enough to reuse much of the existing playbook. The product changed, but recruiting, selling, managing field teams and supporting installation had useful similarities.

Recruiting is one of the central skills Edwin believes founders must master. Top performers have options, so a company must be able to persuade strong people that joining its mission is worthwhile.

The interview referenced a conversation with Steven Bartlett in which Bartlett reportedly said he spends roughly 30–35 hours per week recruiting and searching for talent. The example was used to reinforce how much CEO leverage comes from bringing in exceptional people.

Edwin’s own CEO role has shifted from personally executing the work to identifying the part of the organization that most needs attention. He enters a struggling area, diagnoses the problem, builds a solution and then tries to get back out so another leader can run it.

During Skyline’s earlier years, Edwin spent roughly a decade much closer to frontline sales. He knocked doors, trained representatives, recruited people and led the sales organization directly.

His management rule is to “inspect what you expect.” If a department is underperforming, he believes the CEO should inspect it directly, identify the underlying cause and build a process that prevents the same failure from recurring.

A major step in Skyline’s transition from a small company to a larger organization came in 2009 when Edwin hired a CFO for approximately $150,000 a year. At the time, he compared the expense mentally with buying a Ferrari, but later called the CFO one of his best investments.

That hiring decision was part of a much larger reinvestment in infrastructure. Edwin said the office operation expanded from roughly eight employees to around 50 and that he invested approximately $700,000–$800,000 in the company during that phase.

He said he made roughly $1 million that year and reinvested around $700,000–$800,000 rather than treating the entire amount as personal income. He retained roughly $200,000–$300,000 as personal reserves so his basic obligations could still be covered if the expansion failed.

The large reinvestment deliberately increased pressure on Edwin to grow revenue. Once he was carrying a much larger payroll and executive infrastructure, he became more aggressive about recruiting, training and expanding the sales force.

Edwin distinguishes between the correct sequencing for an unproven startup and for a proven growth business. Early on, he accepts “sell and figure it out”; once demand is proven, he believes operations and infrastructure often need to be built ahead of further sales growth.

He warned that scaling sales faster than fulfillment capacity can destroy an otherwise successful company. A business can generate demand it cannot service, damage its reputation and ultimately collapse from growth itself.

Real estate became another important part of Edwin’s wealth strategy almost accidentally. As he upgraded from one dream home to another, he often kept the previous homes rather than selling them and converted them into rentals.

Edwin said he has never personally lost money on a house. He described real estate as the asset class that had been consistently successful for him and as a useful destination for cash generated by operating businesses.

His stated preference is to use strong business cash flow to accumulate assets rather than allow success to become an excuse to stop working. He warned that sitting on a large pile of cash can reduce urgency and eventually lead to consuming the money instead of compounding it.

Edwin’s leadership philosophy is that a leader’s dream must become large enough to contain the ambitions of other people. The organization becomes more powerful when employees can achieve their own major goals inside the leader’s larger vision.

He describes both his solar and home-security companies as personal-development companies that happen to sell solar or security. The commercial product is secondary in his leadership philosophy to developing the people selling and operating it.

One of his explicit organizational goals is to create an unusually large number of six-, seven- and eight-figure annual earners. He believes employees can possess the technical talent to earn large sums while still being limited by low self-worth.

Education is the central mechanism he uses to build loyalty. He argues that when leaders teach employees things they have not learned elsewhere, employees see the leader as valuable, grow personally and become less inclined to leave.

Edwin intentionally teaches employees entrepreneurship even though some people warn that doing so could create future competitors. He rejects that concern as scarcity thinking and believes a sufficiently large vision can accommodate ambitious people instead of suppressing them.

His retention philosophy is broader than compensation. He believes people remain where they feel that their work matters, that they are seen and recognized, that they belong and, especially, that they are continuing to progress.

Edwin views competition as an organizational tool because competitive people create energy, momentum and pressure on others to improve. He also treats recognition as a deliberate management function because employees want their contribution to be noticed.

He believes a leader must keep developing personally if they expect high performers to stay. If employees continue to grow while the leader becomes comfortable, they can eventually outgrow the leader and leave.

In the home-security industry around 2009–2010, Edwin watched competitors try to imitate a much larger company and scale extremely quickly. He deliberately refused to chase their growth rates and concentrated on making his own company better year over year.

Some newer competitors temporarily passed Skyline in size, but Edwin’s objective was to outlast them rather than immediately outrun them. He self-funded much of his growth, accepted slower expansion and watched several faster-growing competitors eventually go out of business.

He regarded his youth as a strategic advantage in that period. Rather than needing to win immediately, he believed he could survive longer, keep improving and allow time to eliminate weaker competitors.

Edwin tracks performance quantitatively across short and long intervals. He described monitoring results by day, week, month and quarter and comparing current performance with the same periods in the prior year.

His point is that people cannot manage a goal they are not measuring. He used salespeople who do not even know their first-quarter earnings as an example of people lacking the information necessary to manage an annual target.

Large sales teams have left Edwin’s companies during difficult periods, including situations where roughly 25% of the sales force disappeared. He said those teams eventually returned, but losing that much production at once represented a major operational blow.

His crisis response is to separate controllable problems from uncontrollable ones. He applies action to the first category and faith to the second rather than spending energy trying to control events outside his influence.

Edwin sees massive action as one of his personal responses to anxiety, frustration and overwhelm. Instead of trying to solve every problem mentally, he starts completing concrete tasks and uses each completion to create momentum.

He summarized this as answering overwhelm with “overwhelming execution.” When a situation deteriorates, he increases repetitions, creates more opportunities and relies on the law of large numbers rather than waiting passively for conditions to improve.

Repetition is fundamental to Edwin because he believes people revert to their habits when pressure arrives. Whatever has been practiced enough to become reflexive will be easier to execute when conscious thinking deteriorates under stress.

Edwin organizes life around what he calls the “five Fs”: faith, fitness, family, finance and fun. He puts them in that order, with faith first.

He places fitness before family because his definition includes both body and mind. His argument is that someone who is physically depleted or mentally unhealthy cannot consistently give their family the best version of themselves.

Fun is included deliberately rather than treated as an indulgence. Edwin said periods in which he worked without rewarding himself eventually made him bitter and less grateful.

He does not believe genuine excellence is compatible with equal “balance” across all areas of life at every moment. Becoming exceptional in one area sometimes requires temporary obsession, but he believes neglected pillars must still receive enough deliberate attention to keep progressing.

His warning is that allowing one major life pillar to collapse can eventually damage the others. The goal is not equal allocation but continual enough improvement that no important area is abandoned.

Edwin said that by 2016 his mental-development pillar had deteriorated badly. For roughly 16–17 years after the call-center period, he said he had stopped reading books, listening to developmental material and deliberately training his mindset.

During that period he began questioning whether he deserved the level of money and success he had achieved. He experienced thoughts that he was not smart enough, had simply been lucky and would eventually lose everything.

He responded by treating the mind the same way he treated physical fitness. Edwin resumed studying for approximately 30–60 minutes every day regardless of circumstances.

Studying entrepreneurs who had made hundreds of millions restored some of his confidence because he recognized principles in their stories that he had already lived through himself. He said he had previously lacked the language to articulate those experiences rather than lacking the experiences themselves.

That process eventually expanded Edwin’s belief about the level of wealth he could create. He said he came to believe he was capable or “worth” $100 million and then began attracting people capable of helping build on that scale.

Several Biblical ideas form the intellectual framework Edwin repeatedly returns to. He cited Proverbs 18:21 on the power of the tongue, the principle that he can do all things through Christ who strengthens him, and Proverbs 24:16 about the righteous falling and rising again.

Proverbs 18:21 influenced Edwin’s emphasis on positive declarations. He is deliberately cautious about speaking negative outcomes over himself and especially over his children.

He interprets Proverbs 24:16 as a lesson that righteousness or faith does not eliminate repeated failure. In his telling, the essential distinction is continuing to rise after falling rather than expecting a problem-free life.

Edwin said he once expected stronger faith to produce fewer problems but changed that view. He now believes serious challenges continue regardless of faith and can become the conditions through which faith and resilience are exercised.

He links resilience to a group of deliberately cultivated virtues: gratitude, discipline, humility, truthfulness, courage, perseverance and generosity. His point is that these traits are hardest to maintain precisely when pressure makes them most necessary.

He contrasts those virtues with easier reactions such as bitterness, indiscipline, arrogance, dishonesty, fear and greed. Because talent is not always controllable, he argues that character is one area people can deliberately develop.

Tithing appeared as one example in his discussion of generosity. Edwin used it to illustrate his broader belief that desirable virtues are often difficult because they require acting against immediate self-interest.

A manager gave Edwin one of his lasting lessons when he was about 16: the more stress and pressure he could responsibly carry, the more money he could eventually make. He said that statement has stayed with him throughout his career.

He therefore tends to confront pressure rather than escape it. Each survived challenge becomes, in his view, evidence that he can withstand a larger one.

Edwin’s final advice to younger people returned to the importance of large dreams. He believes people are born capable of meaningful achievement and that God may place dreams in them partly to pull them into circumstances where greater dependence on faith becomes necessary.

He does not believe the purpose of every dream is simply the achievement itself. In his religious interpretation, pursuing an intimidating goal can matter because of who a person becomes and how it changes their relationship with God.

His recurring principle is that worthwhile things are generally “uphill,” while easy paths tend to move downhill. He intentionally seeks difficult challenges because he believes he feels most alive when something substantial is demanding growth from him.

Once one category stops being challenging, Edwin looks for another. He suggested that someone no longer motivated by making more money might challenge themselves to give more away, deepen their faith, strengthen their fitness or improve another neglected area.

Edwin said 2024 had been a down year for the businesses. At the time of the interview he said he was rebuilding both companies while also dealing with significant family-side difficulties, which he framed as another challenge to work through rather than a final defeat.

He defined faith and fear as opposite projections about a future that has not yet happened. Faith imagines the best plausible future, while fear imagines the worst, and he believes both require mental energy before either outcome exists.

Edwin said that, for him, roughly “90% of winning” has been faith. When faced with uncertain outcomes, he deliberately chooses to direct his imagination toward success rather than rehearse failure.

His desired legacy is centered more on the people he develops than on products, revenue or companies. He wants to create leaders and unusually successful earners who can trace part of their development to his organizations.

Edwin said he has not sold his company partly because he still enjoys changing people’s lives through it. He views his own transformation from a shy, stuttering and financially desperate teenager into a major business owner as something he wants to reproduce for others.

He wants the same leadership and faith principles passed to his children through example rather than lectures alone. His formulation was that important things are often “caught” rather than taught, so his behavior has to match the character he tells them to develop.

For his children, Edwin specifically wants to recreate the foundational belief his mother gave him—that God remains with them during both good and bad periods. His desired family legacy is children who become leaders, develop character and lean more heavily on faith when difficulties arrive rather than abandoning it.

Edwin said his public social handle had recently been changed from “Tedwinator” to an account using his name and “official.” He joked that his wife had finally approved the change.

His companies were still actively hiring at the time of the conversation. Edwin said people could contact him by direct message, that he personally still checks those messages, and that he tries to answer questions or share useful knowledge when possible.