I Had $0 Left.. Now I Make $10M/Year

Chris Waters is the founder and CEO of Waters International Realty, and the hosts said his company had sold hundreds of millions of dollars in real estate in the previous year alone. A prior interview with Waters had generated millions of views across platforms, surprising people who knew him but had not realized the scale of his financial success.

Waters entered real estate through a demanding customer from his college lawn-mowing business. The customer and his wife operated a small Keller Williams team and persuaded Waters to get his real-estate license and join the industry.

His first attempt at real estate lasted only about three or four months because he lacked patience and coachability. Waters said he dismissed advice from an experienced salesperson, saw artificial ceilings everywhere and quit because he could not see how the business would make him rich.

Waters later identified his early lack of humility as one of the central reasons he struggled. He eventually concluded that being open-minded, coachable and willing to learn from people who have already solved a problem is essential to entrepreneurship.

After leaving real estate, Waters spent roughly two or three years working as an oil-and-gas landman in Texas. His job involved locating mineral-rights owners; he described the conventional 8-to-5 work as miserable, while keeping his real-estate license active and doing occasional deals during evenings and weekends.

Waters aggressively saved his income and then put essentially all of it into an Austin bar and restaurant in December 2009. The business was near Sixth Street, and part of his reasoning was something he had read suggesting alcohol sales could rise during economic downturns, despite having no experience as a bartender or restaurant operator.

The restaurant failed about nine months later and virtually wiped Waters out. He arrived to find chains on the doors, a Texas Alcoholic Beverage Commission notice and an eviction; he said he had less than $10 in his account, possibly a negative balance, and owed money to numerous people.

The restaurant collapse became a major personal turning point because it forced Waters to admit he needed to learn rather than simply assume he could figure everything out himself. Real estate was the one field he still knew, so around 2010 he returned to it with almost no financial resources.

Unable to afford leads or sophisticated software, Waters built his real-estate pipeline through relentless cold calling. For roughly six months he prospecting in morning, lunchtime and evening blocks seven days a week, putting an estimated 30–40 hours a week into calling while often producing only one or two face-to-face appointments.

Waters said he was initially terrible on the phone, especially at listening and showing empathy. His then-girlfriend, now wife, repeatedly criticized his delivery; in one memorable call, he immediately treated a recently widowed woman's need to sell as a promising lead rather than first responding to what she was going through.

After roughly six months of poor results and continuing financial pressure, Waters hired a sales coach. The coaching focused on practical skills such as cadence, tonality, objection handling, listening and knowing when to sound enthusiastic versus empathetic.

Waters said coaching increased his appointment production by roughly 300–400%, from about one appointment a week to four or five. Once servicing clients consumed too much of his prospecting time, he hired his first inside salesperson to make calls and book appointments, which he said increased his personal productivity by another 300–400%.

Waters describes entrepreneurship as a skill-based ladder rather than something fundamentally different from a corporate career ladder. His basic progression consists of learning inside sales, then outside sales, then developing deep subject-matter expertise through actual transactions.

Inside sales is the first major skill in Waters's framework because entrepreneurs must learn how to turn a conversation with a stranger into an appointment. That includes objection handling, voice control, empathy, listening and creating enough trust to move the relationship forward.

Outside sales is the second skill: converting strangers into clients once the meeting occurs. Waters's sequence is to build rapport, educate the prospective client, establish credibility, clearly differentiate the value being offered and ultimately ask for the business.

Waters deliberately places subject-matter expertise third rather than first. He argues that entrepreneurs often wait to become experts before approaching customers, when in practice expertise develops through getting in front of customers, completing transactions, learning what the market wants and improving the offer with each repetition.

His broader business philosophy is therefore market-first rather than study-first. Entrepreneurs should discover actual demand, begin transacting, incrementally add value and allow repeated experience to turn them into experts instead of waiting indefinitely for theoretical mastery.

Waters said the first year he paid taxes on $1 million of net income marked a psychological turning point, but not entirely a positive one. Roughly six months later, in 2014, he bought an Audi R8 that he had wanted for years and began feeling that he had “made it.”

The Audi R8 became a symbol to Waters of the danger of becoming comfortable after reaching a major goal. He said he began losing his edge and later adopted the idea that once a goal is achieved, another meaningful objective must quickly replace it to preserve forward momentum.

Waters attributes part of his 2014 stagnation to ego, lack of focus and investing in too many unrelated ventures. He believes his core business could have grown substantially faster had he remained disciplined instead of spreading himself across multiple projects.

He now believes entrepreneurs sometimes need to deliberately preserve difficulty and challenge rather than optimize their lives entirely for comfort. The discussion connected that idea to the argument that gradual struggle develops the capabilities required to retain and manage success, rather than merely obtaining it.

Waters's entrepreneurial exposure began at about age 12, when his mother told him he needed to earn money for extracurricular activities she could not afford. She was an emergency-room nurse raising Waters and his brother, and helped create door hangers for a small business called CJ's Lawn Service.

The childhood lawn business gave Waters his first practical lesson in marketing. His mother and brother distributed door hangers, customers called, and Waters—who recruited another neighborhood child to help—earned about $25 per lawn and became fascinated by the direct connection between marketing and sales.

He also liked the autonomy of working for himself from an early age. Choosing his schedule and rules made entrepreneurship more attractive than conventional employment.

In high school around 1998–99, Waters worked at Circuit City and exploited the employee discount on car-audio equipment to resell products on the newly emerging eBay. Employee discounts could reach roughly 50–70%, creating an obvious resale margin.

Circuit City eventually fired Waters over the resale activity. He said management and a corporate representative confronted him with pages of employee purchases; Waters argued that the written policy did not specifically prohibit eBay resale, and he said the company subsequently issued a new companywide rule explicitly banning the practice.

During his freshman year of college, Waters moved to upstate New York to help an uncle who had purchased a franchise. He deliberately used the experience to study how a franchise playbook turns a repeatable system into a functioning business.

Waters disliked the New York climate—he recalled roughly 120 inches of snow that year—and wanted to return to Texas without taking on a college loan. Using money saved while working with his uncle, he returned to the door-hanger strategy and rebuilt a lawn business in Texas to help pay for school.

Waters believes genuine entrepreneurship requires an unusually high tolerance for risk, hardship and sustained obsession. In his view, many people like the idea of entrepreneurship, but relatively few are willing to bet heavily on themselves, endure prolonged adversity and continue working until they find a solution.

Focus became one of Waters's biggest lessons after his own failed diversification. Inspired partly by The Magic of Thinking Big, he argues that entrepreneurs often mistake a temporary growth ceiling for the limit of their core business and chase unrelated ventures instead of creatively finding the next expansion path inside the business they already understand.

Waters links several of his worst periods to operating without an outside coach or accountability partner. He had no coach during the period surrounding the Audi R8 and his aggressive diversification; roughly 18 months later, as those ventures began deteriorating, he hired another coach.

By 2024, Waters was using several specialized advisers rather than one general coach. He described having a CEO adviser, a financial/CFO-type adviser and a marketing adviser, while saying he still needed someone focused on physical fitness.

His financial adviser helps him model the six-to-12-month consequences of major business decisions before Waters commits capital. That includes forecasting how much an initiative will cost, how far cash reserves may fall and when a return should realistically begin.

Waters said falling cash reserves can create emotionally bad decisions for high-drive entrepreneurs because cash becomes a psychological scorecard. Knowing in advance that reserves are supposed to fall during a planned investment period helps distinguish an expected drawdown from a genuine crisis.

He particularly values financial advisers who challenge entrepreneurial optimism rather than act as “yes men.” A more conservative adviser can force the entrepreneur to test assumptions, model downside scenarios and defend why an investment should work.

Waters embraced Daymond John's line, “Pioneers get slaughtered, but settlers prosper,” as a warning against unnecessary reinvention. The discussion noted that many extremely wealthy people own conventional businesses such as HVAC or plumbing companies rather than creating the next Google.

He believes humility should push entrepreneurs toward proven models before radical innovation. Real estate has existed as a mature industry for generations, yet in his twenties Waters was sitting on what he described as a red IKEA couch trying to figure out how to outcompete national companies such as Zillow instead of first mastering an established model.

Waters recommends modeling people who have already succeeded in the same industry, building a reliable revenue foundation and then funding experiments from discretionary profits. Innovation should come after the economic engine works, not as a substitute for proving that customers will buy.

His failed restaurant also shaped his belief in testing ideas at the smallest practical scale. Rather than spending hundreds of thousands of dollars building a restaurant, he now suggests testing demand through something like a food truck or supplying prepared food through an existing retailer before committing major capital.

The difficult 2022–23 housing market reinforced those lessons. Speaking in January 2024, Waters said U.S. home-sale transaction volume in 2023 had fallen below 2008 levels and that his brokerage had been getting “kicked” for roughly 18 months.

Waters said his company had sometimes spent $500,000 to $1 million testing initiatives that could have been tested for approximately $50,000. The downturn strengthened his commitment to focus, discipline and minimum-viable-product thinking.

He rejects the idea that early entrepreneurs primarily suffer from a lack of resources. His view is that the real constraint is often resourcefulness: most concepts can be tested inexpensively, revenue can then be reinvested incrementally, and outside capital becomes easier to obtain after a repeatable growth record exists.

Waters does not think “selling yourself” requires elaborate personal branding when the underlying confidence is genuine. He said confidence grows through repetitions and competence, while energy, hunger and excitement can persuade people even before someone has decades of experience.

Early in Waters's real-estate career, homeowners sometimes hired him primarily because he seemed more excited to sell their house than competing agents. He sees authentic enthusiasm and passion for the product as foundational sales advantages.

Waters rejects an 8-to-5 mentality for someone seeking unusually large entrepreneurial outcomes. His broader argument is that exceptional results generally require periods of obsession and effort that exceed the expectations of conventional employment.

The hosts described Waters's company as expanding beyond its original market into other Texas cities by roughly 2015. Waters said the critical transition was moving from personally mastering sales to learning how to lead other leaders and build an organization capable of reproducing results without him doing everything.

He separates employees into rare “unicorn” performers and a much larger population of useful “utility players.” The practical goal is not to expect every employee to behave like the founder, but to recruit enough exceptional leaders to direct a larger organization of solid specialists.

Scaling therefore requires a clear strategy, short operating cycles and accountability. Waters emphasized setting quarterly tactical priorities and ensuring key leaders remain coachable, resourceful and capable of executing against them.

Waters cited a striking industry statistic that roughly 98% of real-estate agents close fewer than about 1.5 transactions per month. He considers roughly 1.5–2 closings a month, or 18–24 annually, a basic threshold for developing enough current transaction experience to function as a genuine market expert.

Internal surveys at Waters's company repeatedly found prospecting to be the activity agents disliked most. He said approximately 99% identified calling strangers as their least favorite part of the job, even though many were perfectly comfortable talking when someone called them first.

Waters believes many people enter real estate with a mistaken picture of the job. They expect flexibility, showing attractive properties and face-to-face interaction, whereas successful agents who must generate their own business often spend significant time prospecting and building an appointment pipeline.

Waters International responded by removing cold prospecting from its agents' core job rather than trying to force every agent to enjoy it. The company created an inside-sales operation that generates and books appointments so agents can concentrate on face-to-face meetings, showings and closing business.

That model deliberately separates inside sales from outside sales in the same way large companies create specialized jobs. Waters tells recruits that his agents are primarily outside salespeople; someone who wants to be a full entrepreneur responsible for every function may be a poor fit for his organization.

The specialization model traces partly to Gary Keller's The Millionaire Real Estate Agent, which Waters's mother gave him when he graduated college. Waters later concluded that the same principle appears in high-growth companies generally: successful large organizations consist of specialists rather than one person performing ten unrelated jobs.

The founder's job evolves from learning multiple functions personally to knowing when each function should become someone else's full-time specialty. Waters stresses that this requires surrendering control and accepting that delegated employees may sometimes fail.

Waters said one of his biggest recruiting realizations came around 2012–13, when he was working 18–19-hour days and wearing numerous hats. Exhausted founders often hire the first available person as relief, but a weak hire can create more problems instead of increasing capacity.

George Anders's The Rare Find strongly influenced Waters's approach to recruiting. He focused on the common pattern in organizations such as elite financial firms, Special Forces and Teach for America: an extremely broad candidate funnel combined with a very selective final filter.

Waters uses the acronym RSTLM—recruit, select, train, lead and motivate—to describe core leadership responsibilities. Of those functions, he considers recruiting and particularly selection the highest-leverage activities because exceptional self-driven people require comparatively little management.

His hiring philosophy is that elite organizations create meaningful barriers to entry rather than treating every applicant as scarce. A wide recruiting funnel gives a company enough choice to reject merely adequate candidates and retain the strongest performers.

Waters considers a conventional one-hour interview weak evidence because almost anyone can perform well temporarily. He prefers putting candidates through practical versions of the work so the company can observe their behavior under realistic pressure.

Inside-sales candidates at Waters's company are tested through a role-play involving a homeowner whose listing failed after six frustrating months and who now distrusts real-estate agents. Candidates must attempt to overcome that hostility and secure an appointment without extensive preparation.

The company intentionally rejects the candidate at the end of the role-play regardless of how well the call went, then watches the reaction. Waters said weaker responses usually fall into two categories: excessive self-promotion or becoming angry and defensive.

He recalled a Pepperdine graduate who reacted to the simulated rejection by invoking how difficult her university was to enter and arguing that rejecting her would be a mistake. Waters used the example to show how pressure can expose defensiveness that a conventional interview might never reveal.

The response Waters wants is curiosity rather than defensiveness: asking what the employer was looking for and continuing the conversation. For an inside salesperson who will hear rejection constantly, that response signals resilience, emotional control and the instinct to gather information rather than immediately surrender.

Waters therefore recommends incorporating real work into hiring whenever possible. The test does not need to resemble months of Special Forces selection; even a short realistic exercise can reveal far more than an ordinary interview about how a candidate will actually perform.

For residential investors in the 2024 environment, Waters identified “subject-to” transactions as a major opportunity created by homeowners holding mortgages around 2.5–3%. The target is an owner who needs to move, has little equity and therefore may be unable to sell conventionally after transaction costs.

In a subject-to transaction, the investor takes ownership of the property while the existing mortgage remains in the original borrower's name and the investor assumes responsibility for making the payments. Waters presented the structure as a way to acquire property with little or potentially no initial cash while relieving a seller who cannot easily exit the house.

Waters suggested lining up a tenant before completing a subject-to purchase to reduce the investor's cash exposure. With the seller's written permission, the property can be marketed for rent and the seller's move-out, closing and tenant move-in can be coordinated to minimize vacancy.

A subject-to deal only works economically if the property's total monthly carrying cost is safely below achievable market rent. Waters emphasized calculating principal, interest, taxes and insurance and leaving positive cash flow for repairs and other incidental expenses rather than merely matching the mortgage payment.

Waters also identified wholesaling as a low-capital entry point into real-estate investing. The investor finds a distressed or underpriced property, gets it under contract at a discount and transfers or resells the opportunity to another buyer, earning the difference for sourcing the deal.

He suggested physically identifying neglected properties and using public foreclosure information as potential lead sources. County courthouse foreclosure lists are public records, and Waters noted that properties pulled from one scheduled sale often return later if the owner's financial problem remains unresolved.

Across both investing strategies, Waters returned to the importance of outside-sales skill because the transaction begins with a stranger trusting the investor. An investor asking a homeowner to transfer a deed while leaving a mortgage in the homeowner's name must establish rapport, credibility, expertise and a compelling explanation of why the arrangement serves the seller.

The hosts connected Waters's sales framework to their own success reaching high-profile guests. They described cold outreach eventually leading to a telephone conversation with Grant Cardone's assistant, where they still had to persuade a gatekeeper to give them access; Waters classified that as another form of inside sales.

The discussion emphasized that effective cold outreach must be deliberate rather than vague. The hosts contrasted strategic requests with the large number of generic direct messages they receive that begin with little more than “question for you.”

One host said door-to-door sales for a home-remodeling company had been a major character-building experience. On one canvassing trip he knocked on a house where the resident opened the door holding a rifle; he later learned the entire neighborhood belonged to one owner and consisted of renters, meaning none of the residents could buy the decks and patios he was selling.

Waters International said it operates a scholarship program for people entering real estate, including paying approved recruits' real-estate-school costs. Waters stressed that admission is deliberately difficult and follows the selective hiring philosophy he described throughout the conversation.

Waters also said he remains active outside brokerage through real-estate investing and angel investing. His current activities therefore extend beyond selling homes into acquiring assets and backing other ventures.