Justin Waller on Business, Moving Out of Your Hometown, Dating & The Power of Focus

Justin Waller was introduced as a serial entrepreneur and founder/CEO of Red Iron Construction, an eight-figure construction company operating across the United States and beginning to expand internationally. The School of Hard Knocks hosts James, Jack and Josh interviewed him in Miami about his background, business building, investing, leadership and personal philosophy.

Waller grew up poor in south Louisiana in a household that included violence and family conflict, and he said his family was not even middle class. Rather than seeing that environment as his inevitable future, he became conscious early that other kinds of lives were possible.

Sports gave Waller his first meaningful exposure to families living better than his own. He was a strong athlete and a varsity starter as a sophomore, which put him in other families’ homes and more affluent neighborhoods and showed him possibilities he had not seen growing up.

He believes proximity makes previously intimidating levels of success feel normal and attainable. Seeing better homes and lifestyles as a teenager shaped his later belief that physically placing yourself around success can expand what you consider possible.

Construction initially seemed like the only realistic path Waller knew for making serious money without becoming a doctor or entering a traditional professional career. He described it as making “doctor money” while wearing work boots.

Living in Miami later broadened Waller’s thinking beyond construction. He said the environment exposed him to business models that may produce a much greater return on his energy than traditional construction.

Waller encourages young people to leave their hometown temporarily, but not necessarily to abandon their work or spend months traveling. His version of travel is spending a few days in places such as Miami or Los Angeles, continuing to work while observing people, businesses, wealth and lifestyles that are uncommon at home.

He said exposure to successful people is valuable less because of Ferraris or Lamborghinis themselves than because it makes freedom and alternative ways of living feel less foreign. His argument is that repeated exposure can break the psychological assumption that those lives belong to a completely different class of people.

Waller believes cities have distinct cultures and “souls” that can affect ambition and creativity. He cited living in New Orleans and visiting Los Angeles, Denver and Utah in his twenties as experiences that energized him before he returned home to work.

Travel also taught him that many places are less different than they initially appear. Working across markets led him to see similarities between places such as Mobile, Alabama, and Baton Rouge, Louisiana, which increased his confidence that a business process working in one market could work elsewhere.

He values pattern recognition as a major entrepreneurial advantage. Once he understood that customers, workers, hotels, retailers and basic operating conditions repeat across markets, geography became much less intimidating to him.

Waller said this is one reason he sees value in truck driving for a young person: it exposes someone to many parts of the country and reveals recurring patterns in people and communities.

He considers his steel-erection skill highly portable. Waller repeatedly said that if he lost everything and were dropped into virtually any American city—or even another country—he believes he could be hanging steel again within about six weeks.

The deeper asset, in Waller’s view, is competence rather than the company or money currently attached to it. He believes accumulated skills, systems knowledge and confidence cannot be taken away by bankruptcy or the loss of a particular business.

Waller pushed back on the idea that wealthy people are fundamentally different from everyone else. He described himself still grocery shopping, meal-prepping, eating inexpensive rotisserie chicken and salad, and watching educational YouTube videos much like he did before becoming wealthy.

He said his experience with affluent entrepreneurs has made him associate sustained success with persistence, relationships and surviving repeated failures rather than with some mysterious personal quality. He also argued that success can be humbling because successful people often remember how many serious setbacks preceded it.

Waller described money primarily as a tool and a scoreboard rather than an ultimate purpose. In his framing, financial results are evidence that value was created, but money by itself is not what he considers most important.

He advised judging wealthy people individually rather than assuming money reveals their character. His suggested tests were simple: spend time with them, watch how they treat service workers and ask about their failures.

The podcast hosts said entrepreneurs were often the people most willing to stop and speak with them when they were building their channel by approaching strangers in financial and technology districts. They interpreted this as experienced entrepreneurs recognizing the persistence required to start from nothing.

The hosts and Waller both rejected the assumption that most successful people began wealthy. They discussed people who used difficult childhoods or financial circumstances as motivation to create a different future for themselves and their children.

Waller said pursuing an unconventional path means repeatedly being challenged by people living more conventional lives. He described friends questioning his choices, reminding him of what his business had not yet accomplished and interpreting his changed priorities as evidence that he had “changed.”

His response is that he did change because his goals and the person he intended to become changed. He does not consider preserving an old identity or lifestyle a worthwhile goal if it conflicts with where he wants to go.

Red Iron’s growth involved repeated serious setbacks, including losing money, dropped steel, injured workers and stolen trucks. Waller treated these events as part of the operating reality of entrepreneurship rather than evidence that the business should automatically be abandoned.

His central resilience principle is that competitors are being hit by many of the same difficulties, so endurance itself becomes a competitive advantage. When something goes badly, his question is essentially who will quit first.

Waller became the youngest board member of a metal-building contractor association and estimated that he was roughly 25 years younger than many people around the table. Rather than viewing the age gap as a disadvantage, he concluded that he had decades available to absorb mistakes and learn the industry.

He said multiple people have left him or the steel industry to start companies of their own and later returned. Waller attributes his own durability less to exceptional genius than to building systems, surviving mistakes and continuing after failures that cause others to leave.

Waller strongly advised entrepreneurs to master one business before trying to become serial entrepreneurs. He compared personal energy to a limited supply of water: spreading it across five young plants may keep any of them from becoming large enough to bear fruit.

He believes operating one company through real scaling teaches lessons that cannot be learned by repeatedly starting small businesses. Someone who leaves every company before it becomes large never learns what happens when accounts receivable, cash flow, management and organizational complexity become serious.

Waller described businesses as having life cycles resembling human development. Early-stage companies are like infants making basic mistakes; growing companies become more dangerous as larger amounts of money and receivables create the ability to seriously damage themselves; mature companies eventually reach a period when their systems operate effectively.

He warned against mistaking modest early revenue for mastery. His example was an entrepreneur reaching roughly $500,000 in revenue while making only a fraction of that in profit and then assuming they are ready to build several unrelated businesses.

Waller believes serial entrepreneurship is over-glamorized. For most people, he recommends first building one dominant company that financially stabilizes their life and teaches them how to scale before spreading attention elsewhere.

If Waller were starting his career again, he said he probably would choose real estate rather than construction. His reason is not that construction failed him, but that construction requires repeatedly winning new projects while certain other models create recurring or residual income.

He advises young entrepreneurs to study the economics of a business model before falling in love with the industry itself. He favors models in which work performed today continues generating revenue later, rather than businesses where every completed transaction forces the owner to start hunting for the next customer.

He contrasted recurring revenue with his own early construction experience. A backyard metal building might earn him only about $2,000–$3,000, after which he could still have hundreds of prospective customers who required follow-up before another transaction occurred.

Waller recommends looking at someone roughly 20 years ahead in the career you are considering and studying that person’s actual daily life. His test is simple: if that is approximately the life the industry produces, would you still want it?

He warned young people not to assume they will somehow escape the normal economics and lifestyle of an industry simply because they are unusually talented. If the typical successful veteran’s life is unattractive to you, his advice is to choose another model before investing decades in it.

Waller began diversifying into real estate only after construction had become a substantial source of wealth. At the time of the interview, he said his group had acquired about 300 rental “doors” that year and that he had closed four trailer parks in a single month.

He considers real-estate underwriting a broadly useful financial skill. He specifically mentioned learning net operating income, cash-on-cash return, internal rate of return and the fundamentals of evaluating a deal.

Waller said real estate became actionable for him because he spent years studying deals before opportunities arrived. After construction work, he would sit at his computer at night, underwrite properties himself, watch educational material, run the numbers repeatedly and analyze listings on LoopNet.

He learned to scrutinize sellers’ projections instead of accepting a pro forma at face value. Repeated practice taught him to recognize assumptions that looked unrealistically perfect and to form his own view of what a property was worth.

That preparation gave him confidence to act quickly when genuine opportunities appeared. He said enough underwriting experience can allow an investor to recognize a good deal immediately and confidently approach someone for substantial investment capital rather than hesitating.

Waller uses real estate both as an investment and as part of his tax strategy. He discussed depreciation and cost-segregation studies, along with using property deductions in relation to income from his construction operations; these were descriptions of his own approach rather than detailed tax advice.

His real-estate strategy includes value creation rather than simply collecting existing rent. He mentioned raising rents, adding additional trailers to parks and making other improvements designed to increase cash flow and property value.

Waller said he expected to move beyond existing properties into development of large apartment complexes. That represented a planned next stage of his real-estate activity.

Red Iron Construction traces back to around 2011 and began with Waller and two other people working from a truck. He had studied construction and initially took small jobs, including backyard metal buildings.

His first important commercial job took roughly three weeks and produced about $25,000 for him when he was around 24 or 25. That result showed him how profitable the business might become if he could eliminate losing projects and occasionally land unusually profitable ones.

Another early roofing job reportedly produced roughly $50,000–$60,000 in about two weeks. The size and speed of those early profits convinced him that scaling the model could create substantial wealth.

Reading The E-Myth helped shift Waller from simply doing construction work toward building systems around the work. He began formalizing processes and hired an estimator, which became an important turning point.

Hiring an estimator created pressure to build an organization around the increased volume of bids. More bids required more workers, scheduling, supervision and eventually project managers, so delegation effectively forced the company to grow beyond Waller himself.

Waller cautioned that extremely fast early success can create dangerous overconfidence. He said entrepreneurs sometimes stumble into an unusually favorable model, become wealthy quickly and mistakenly conclude that success in that one business means they are prepared to operate completely different or heavily regulated businesses.

He considers unknown blind spots one of the greatest risks when entering a new industry. His advice is to find people with deep experience who have already suffered the expensive mistakes you have not yet encountered.

Waller said the first condition for useful advisers or employees is psychological safety: people must know they can disagree with the owner without being punished simply for offering an opinion. Otherwise leaders surround themselves with people who say yes regardless of whether a plan makes sense.

He distinguishes hearing advice from surrendering decision-making authority. Waller believes the leader still has to make the final call, but employees should know their opinion was genuinely considered even when the leader chooses another direction.

He said he would be furious if a failed initiative were followed by an employee saying, “I knew that wasn’t going to work,” because he expects concerns to be raised before the failure. To him, silence in that situation means either the employee did not care or the company failed to create a culture where speaking up was safe.

Waller considers culture more fundamental than strategy. A sophisticated plan has limited value if the people expected to execute it do not trust the organization or care about the outcome.

He deliberately acknowledges when someone on his team has a better idea than his own. His stated principle is that he does not need to be personally right; he needs the team to win.

Among the business books discussed were The E-Myth, Rich Dad Poor Dad and several books by Patrick Lencioni, including Death by Meeting, Getting Naked and The Ideal Team Player. Waller said most of his reading has been business-oriented and mentioned Tony Robbins as a more general personal-development option.

Waller said learning to delegate is important, but allowing yourself to delegate can be even harder. Founders often keep responsibilities because they can perform them, even when their personality and energy make them poor long-term owners of those functions.

He advises founders not to automatically hire people who resemble themselves. Two highly similar founders may both gravitate toward the same work while neglecting the functions neither enjoys.

Waller used estimating as his own example of a role he was capable of doing but should not have retained. He disliked sitting for hours with technical drawings, specifications and legal details, whereas a detail-oriented estimator enjoyed exactly that work, so Waller effectively “fired” himself from estimating.

His hiring philosophy is to match natural tendencies to the job. He sees outgoing personalities as better suited to some sales roles and highly precise, introverted personalities as potentially well suited to accounting or technical work.

The owner’s job, in Waller’s view, is to design roles in which both the employee and the founder can naturally perform well. He would hire someone very similar to himself mainly if he wanted that person eventually to replace him in the role.

One of Red Iron’s biggest early growth tactics was making a very small company appear professionally prepared enough to compete for major commercial work. A mentor gave Waller a polished proposal template, which he adapted for Red Iron, and he paid to create a formal prequalification package emphasizing matters such as safety.

At the time, the company had only about four people, but its bid materials looked like those of a much larger steel-erection contractor. Waller used that credibility to move away from backyard projects and target larger commercial buildings.

He developed a systematic method for identifying every general contractor bidding a project rather than relying only on contractors who already knew Red Iron. An employee called architects’ offices for pre-job information that revealed which general contractors were bidding.

If one contractor invited Red Iron to quote a project and ten contractors were bidding it, Waller would send the finished bid to all ten. Even when those unsolicited contractors did not win the project, Red Iron often ended up on their bidder lists for future work.

That prospecting system created enough volume that Waller moved his estimator from part-time to full-time and created a formal bid schedule. The company eventually produced roughly five or six bids per week.

Waller recalled bidding roughly $20 million worth of work during one growth phase and winning several million dollars of it while he was only about 26. The precise amount won is unclear in the transcript, but the scale of bidding marked a major leap from the company’s backyard projects.

Red Iron also used contractor databases and construction lead services to find general contractors and submit bids aggressively, whether or not the company had been personally invited. Waller credits that outbound bidding process as one of the most important things that accelerated the company.

He reinforced that prospecting by visibly branding completed work. He put Red Iron signs on jobs, photographed projects and distributed those results through social media to make the growing track record visible.

Waller identified physical training as one of his core personal habits and described the gym as almost a church to him. Fitness is not a side interest in his framework; he sees it as foundational to discipline, confidence and business performance.

Another important habit is spending substantial time alone thinking, often while driving. The hosts referenced Waller spending roughly one to two hours driving by himself, and he said early-morning quiet is particularly useful because it allows internal thoughts to become audible without constant external noise.

His references to waking at 4:00 a.m. were not a universal prescription. He explicitly said he does not always wake at 4 and was not telling everyone else they must; the underlying point was to create enough quiet to recognize what you already know you need to do.

Waller’s core sales advice is to sell something you believe genuinely improves the customer’s situation. He argued that if a salesperson sincerely believes not buying would leave the customer worse off, conviction becomes visible and selling becomes much easier.

He contrasted that with selling a weak or deceptive product. If the seller privately knows the offer is “snake oil,” Waller believes that uncertainty appears in their behavior and makes conviction difficult to fake.

He recommends selling by clearly showing the customer what their future could look like with the product. The more specifically and confidently that future can be explained, the stronger the sales conversation becomes.

In construction, Waller separates winning the first job from winning repeat business. The initial sale requires confidence that Red Iron can meet the schedule and coordinate with other subcontractors; repeat work comes from how the company behaves when the inevitable problems begin.

He emphasized that construction projects routinely face rain, stuck equipment, worker errors and late materials. Customers remember contractors who continue communicating and solving problems when conditions deteriorate.

Waller said he lost roughly $50,000–$60,000 on individual jobs for one major customer but refused to disappear or abandon the relationship. The customer continued awarding Red Iron work, and Waller said he eventually recovered the money through later projects.

He believes reliability during losses creates unusually durable customer relationships because construction has many operators who disappear after a serious problem and reopen elsewhere. Staying visible and accountable when a project hurts financially becomes a form of differentiation.

Waller’s most serious business crisis left him approximately $1 million down and believing bankruptcy was possible. He remortgaged his house to help make payroll, maxed out lines of credit and credit cards, and moved cash between accounts simply to keep obligations covered.

The crisis followed an attempted scale-up that included hiring an experienced person whose performance did not work out as expected. Waller described consecutive estimating or bidding failures that cost roughly $250,000, then another $100,000, followed by additional losses.

He said the financial blows left him mentally exhausted for roughly eight months to a year and wanting badly to quit. By that point, however, he felt he had “burned the boats” enough that walking away without another serious skill or direction was not a realistic option.

Instead of abandoning construction, Waller analyzed where the major risks were actually coming from and rebuilt much of the company. He changed how contracts were structured and how the business dealt with employees, subcontractors and customers.

The restructuring began working, which convinced him to commit fully to the revised model. Looking back, he believes the near-collapse forced operational changes he might never have made while the company was comfortable.

Waller does not consider himself a social-media expert and attributes much of his online growth to having built credibility before becoming a public personality. He had already spent years quietly building a substantial real-world business in Louisiana before appearing prominently online.

He said established creators were willing to bring him onto their platforms partly because his offline track record gave him credibility. Those appearances helped accelerate his audience growth.

Waller had wanted to create YouTube content earlier but intentionally delayed because he had personal business goals he had not yet achieved. He said he would have felt dishonest presenting himself publicly as an authority before meeting those standards.

He sees his audience as a movement more than an entertainment channel. The feedback that matters most to him is people saying his material changed their lives, rather than simply recognizing him from the internet.

Waller said he still has a persistent internal voice telling him he could have performed better despite his success. His self-improvement framework therefore is not based on reaching a point of complete satisfaction but on managing what continually enters his mind.

His third major habit was to “guard the gates” of the mind by deliberately controlling information consumption. He said his personal YouTube feed contains almost no entertainment and is dominated by subjects such as business, real estate, interest rates, history and geopolitics.

He recommends actively retraining social-media algorithms around the life someone wants to build. That means marking distracting content as unwanted and deliberately searching for subjects such as real estate, banking, business and other skills until the feed becomes educational.

Waller believes knowledge reduces fear by turning something vague and intimidating into something understandable. In his analogy, fear resembles mistaking an unknown shape in a dark closet for a monster; turning on the light reveals what is actually there.

He also warned that discouragement can come from people who genuinely love you rather than enemies. His father, whom Waller described warmly, sometimes encouraged him to slow down because he feared the business might become too large and collapse.

Waller summarized this dynamic as “suppression is wrapped in love.” His point was not that relatives or friends are necessarily malicious, but that their own fear and comfort levels can quietly push someone toward smaller goals.

He argued that another person’s progress can unintentionally force friends or relatives to confront things they have not accomplished themselves. That discomfort can produce discouraging advice even when the person giving it believes they are being protective.

His recommended response is to remain kind while holding the boundary. He used refusing a relative’s food while pursuing a fitness goal as a small example of learning not to abandon commitments merely to avoid disappointing someone.

When asked about people who know their life is going badly, Waller said most already recognize the problem; the larger issue is not knowing what to do next. His practical first step was again to change what they consume and begin exposing themselves to small, actionable examples of making money or improving themselves.

He suggested even modest side-hustle content can shift someone from passive consumption toward thinking in terms of opportunities. His example was learning how people buy and resell items through marketplaces rather than filling every free hour with entertainment.

Waller said money itself is not his highest value; freedom and being able to take care of people he loves matter more to him. He often brings other people on trips and said seeing them enjoy experiences is more motivating to him than the luxury itself.

He claimed he could personally be content living in one of his trailers, driving an F-150 and eating simple meals. He used that contrast to argue that the cars, houses and visible wealth are not the main source of his satisfaction.

A negative viral clip involving Waller and Lila Rose became a test of his relationship with online criticism. He said the clip initially received around 10 million views and later reached far larger numbers, while he learned about it from someone named Thomas rather than finding it himself.

Instead of being devastated by the negative attention, Waller said he became glad the incident happened because it showed him how insulated his real life was from internet opinion. He concluded that his offline relationships and daily life were satisfying enough that strangers online could not ruin his day.

His dating advice to young male entrepreneurs was primarily to remain focused on their mission rather than making dating the center of their life. He argued that women notice men who are disciplined, progressing and visibly building a future.

Waller said he has never favored aggressively “chasing” women and is not especially interested in teaching dating tactics or “game.” His view is that a man who stays focused and becomes attractive through discipline will naturally receive interest and can decide whether to pursue a relationship from there.

He used his own early schedule as an example: even after spending the night with a woman, he would get up around 4:00 a.m., put his boots on and return to work. In his telling, maintaining the mission rather than rearranging life around dating increased rather than reduced attraction.

For young entrepreneurs intimidated by rooms full of older, wealthier or more accomplished people, Waller’s advice was to talk less and listen more. When he first sat on an industry board, he did not try to prove himself by immediately expressing opinions.

He found that experienced businesspeople were often happy to explain their own histories if asked genuine questions. Waller took older industry veterans for drinks, asked how they began, listened to how they built their companies and allowed them to be the expert.

His networking formula is attention, questions and genuine interest rather than trying to impress the most successful person in the room. He believes that approach frequently makes experienced people want to help the younger person voluntarily.

For someone whose existing friends are not pursuing the same goals, Waller recommended deliberately spending more time with people they respect online. He said he often preferred driving alone while learning from YouTube to partying or drinking with people who were not moving in his desired direction.

He sees online communities as capable of supplying real friendship and brotherhood despite geographic distance. That makes it less necessary, in his view, to remain intellectually dependent on the attitudes of whatever social circle happens to be physically nearby.

Waller places physical health above financial wealth because he sees the body as the platform from which money can be rebuilt. If forced to choose between his current money and his current physical condition, he said he would probably keep his body because he believes he could use it to build wealth again.

He believes physical fitness improves both cognition and how other people perceive a person. He associated exercise with clearer thinking and argued that a visibly fit body communicates discipline before someone knows anything about your bank account.

Waller emphasized that his current physique was created rather than inevitable. He described an alternative version of himself still in south Louisiana at roughly 260 pounds, working in a plant and living in a trailer, to argue that his current identity came from repeated choices.

For him, the deeper benefit of fitness is learning to trust yourself. Repeatedly showing up to train proves that you can keep commitments, and he believes that self-trust transfers into accepting difficult business opportunities.

His financial advice to a young entrepreneur beginning to earn substantial money is to automatically remove a large percentage from the spending account. Waller said he has been automatically transferring money out since about age 25 and effectively forces himself to operate as though that money does not exist.

He prefers investing excess earnings in assets that can continue producing without his direct labor. He mentioned real estate, broad-market investments such as the S&P, and some cryptocurrency, while saying his crypto exposure is money he could tolerate losing completely.

Waller now combines luxury spending with substantial asset purchases rather than treating consumption as the primary reward for success. He described putting hundreds of thousands of dollars into deals intended to pay him for years while also owning expensive cars and properties.

One of his greatest financial fears is becoming someone who “was rich once.” Automatic investing is partly a defense against earning a great deal during a strong period and later having nothing permanent to show for it.

He set himself an asset threshold before buying a Lamborghini: he would not buy one until he owned more than 100 real-estate doors. Once the income-producing base existed, he felt comfortable buying the car because recurring property income could support the expense.

If he could give his younger self one business lesson, Waller would choose a model with long-term residual returns on energy. He specifically gave insurance and real estate as examples and again stressed looking at people 20 years ahead before committing to an industry.

Waller said he ultimately wants to be remembered for having a “relentless heart.” He does not expect to be remembered as the smartest person or greatest entrepreneur, but wants to speak what he believes is true even when doing so costs him socially.

He said helping young men is particularly meaningful to him even though some of his views attract substantial criticism. In his own framing, helping young men become stronger and more capable also benefits the women and families around them.

Messages from people saying his work changed their lives are the form of recognition he values most. He described relentlessness, generosity and caring about people as more important parts of the legacy he wants than his financial achievements.

His final advice to younger people was to get physically quiet enough to distinguish their own conviction from everyone else’s influence. When family, friends or society are pulling in different directions, he believes the individual must decide what life they can personally commit to rather than borrowing somebody else’s decision.

Waller said even an unusually ambitious or unconventional goal deserves pursuit if, after serious reflection, it is what the person genuinely believes they must do. His closing argument was that a decision aligned with someone else’s fears will never receive the same commitment as one aligned with the person’s own sense of direction.