Sales Coach: Dylan Caudullo Biography

Dylan Caudullo

sales coach Dylan Caudullo

Sales Coach

This nineteen-year-old self-sufficient young man was dozing off alongside his girlfriend on the cozy couch in the living room of his modest, recently leased apartment when he heard several loud bangs echo from the nearby front door. Dylan Caudullo could also discern men yelling at him from outside, instantly developing a bad feeling about the situation, he scrambled off his couch and began hurrying to his bedroom to grab a dagger for protection.

That’s when the door burst open, unleashing a flood of gun-toting police officers into his home on the basis of a judge-issued search warrant. Dylan was hand-cuffed and placed under arrest as his girlfriend helplessly stared down the barrels of fully loaded assault rifles, watching the scene unfold. “I was absolutely terrified,” he reflects. “But at the same time, relieved.”

Throughout a series of court proceedings, the state of Pennsylvania charged him with twelve different offenses, four of which were felonies, while the rest represented misdemeanors. “I called my mom,” he says, recounting his first moments behind bars. “She was desperately trying to bail me out, and even tried to take out loans, but her side of the family simply couldn’t afford to do it. They were scared for me because I was the youngest guy in the county prison.”

Seated on the cold cement floor of a metal cage, surrounded by murderers and society’s worst criminals, this teenager wondered every waking hour how many years of his life would be effectively erased. Considering there were drugs sprawled out all over his apartment when the police raid occurred, he knew it was only a matter of time before convictions got processed. The scariest thoughts of all, what if being a mediocre drug dealer turned out to be the greatest peak his life ever summited or even more tragic, the everlasting characterization of himself.

“If I had the ability to go back and tell myself something at that moment, I’d say don’t worry,” he explains via Zoom call from his new, recently-leased apartment that’s perched atop one of San Diego’s most luxurious skyrises, the property is more commonly referred to as a penthouse, really. “Everything you’re about to do is going to work.”

Yes, believe it or not, Dylan transformed his pathetic existence entrenched within the darkest depths of civilization’s underbelly into potentially the greatest turnaround in the department of corrections’ fairly miserable history. Only a couple of years later, a glance beyond his living rooms glass wall gives way to the shimmering Pacific ocean upon miles of world-class California coastline, a birdseye view of all the magnificent architecture encompassing America’s eighth-largest metropolitan, and on an average evening, plush cotton candy clouds, drenched in orange-reddish tones as the sun dances beneath the Earth’s horizon.

Although these material accolades are impressive, what’s more, is we must analyze how exactly he was able to drastically alter the trajectory of his life. This is where the true treasure of this young man’s story can be found, contemplated, and implemented by others experiencing similar circumstances. Therefore, let’s go all the way back to the very beginning.

The Childhood of Dylan Caudullo

Dylan Caudullo was born in Scranton, Pennsylvania just 21 years ago to a mother that served tables at local restaurants and a father who worked as a software technician. His biological dad abandoned their family so early on, Dylan has a hard time remembering his departure at all because he was still an infant. Regardless, the welfare of him and his two siblings was henceforth thrust into the hands of a young single mother prone to bouncing between dead-end, minimum wage jobs while simultaneously struggling with alcohol addiction.

“I got used to it, that was just life. As I got older and started hanging out with friends, I kind of looked around and thought, ‘wow it’s very peaceful in their house and not crazy,'” he recalls. “People would ask, ‘isn’t it weird not having a dad?’ I was like, that’s just the way it is, it’s not weird for me. I guess once I started taking drugs, I might have dramatized it, making the situation more of a problem than it actually was.”

He may have shown addictive tendencies from an early age, at twelve years old, he was clocking in roughly fifteen-hour days on video game consoles. On another hand, it’s important to note that Dylan’s obsession with gaming is what first introduced him to the idea of making money online. Watching YouTube tutorials on how to do certain things in Call of Duty inspired this pre-teen to launch his own channel, he innocently figured why not give it a shot and make a living doing what he loved! Although the YouTube channel never really blew up, the whole experience ingrained within his subconscious the belief that it was possible to generate substantial income from the internet.

High School

When asked about adulthood ambitions during his freshman year of high school, Dylan slyly attempted to save face by telling classmates he planned to find a cyber-security job, the troubling reality was, he had no clue what he wanted to do, and if aware of anything at all, knew his academic future couldn’t be too bright. “I wasn’t a good student, I was a terrible student. I just did not take school seriously,” he establishes. “I would tell people I wanted to go to college but did not really care. I had no sense of direction.”

That summer turned out to be the first time he smoked marijuana, the opportunity came up while playing video games with a boy who had recently been expelled for bringing “pot brownies” to campus. Amid a brief break in gameplay, the kid asked him if he’d like to try some weed, Dylan said sure, contributed twenty dollars towards buying it, and before long, they were smoking out of a makeshift pipe.

Each puff brought with it a sense of relief Dylan had yet to feel in life, if just for a clandestine moment, the tremendously chaotic family circumstances he was born into drifted away. Getting immediately hooked, not necessarily to the marijuana itself but to the relaxation that accompanied inhaling it, he began selling random trinkets laying around the house in order to fund his newfound method of psychological escapism. As items to hawk started running low, his strategy digressed into selling the very weed he was smoking, locking this minor into a vicious cycle of getting high on his own supply.

He noticed how much the folks around town were willing to pay for quality marijuana and supposed he’d focus the majority of his energy on this illicit, snowballing drug operation of his. “I was still living at my mom’s house so I was trying to keep everything under the radar,” he explains. “Honestly, I didn’t do a very good job, even after buying a weed vaporizer for smoking in the house, she’d always mention to me how it smelled like weed. She never cared too much or tried to take anything away from me, she’d just say something like, ‘stop making it smell like weed in the house!'”

The making of a Drug Dealer

Dylan Caudullo eventually sought out and got hired for a job at Wendy’s, he deemed it an opportunity to make more money, which in turn, meant securing the ability to buy more drugs. Working long hours, this intentioned teenager stayed at the fast-food burger joint for over a year, until he purchased a car and decided to deliver pizzas for a neighborhood pie shop.

The new gig secretly served two financial purposes, getting dependable paychecks cashed and because he’d drive about town every day, spare time and sheer convenience afforded him the chance to drop off drugs at his personal customers’ homes in between pizza stops. The smooth operator hit a road bump, per se, when his vehicle rolled over an embankment and subsequently broke down; not too fond of minimum wage jobs, he began pondering alternative methods of generating an income.

“The idea of making money from online sources kind of sparked back my senior year. I thought to myself, well shoot, cyber-security isn’t looking so hot because I still don’t even understand what it is,” he remembers. “I honestly just didn’t want to go to college. High school was terrible and I didn’t see how college would be any different, plus I’d have to pay for that education! It seemed like a trap so I decided to figure out a way to not go to college.”

Right after graduating and as soon as he turned eighteen, Caudullo moved into his grandparents’ house, viewing it as a place where the next phase of his life could be plotted out. He knew that selling drugs was not the permanent solution to manifesting a decent living, however, what if he did it for just a little bit longer, just long enough to save up for a real business venture or some sort of investment in himself.

“I got this dinky little apartment and was selling drugs heavily. There were people coming in and out all day every day,” he says. “I would hotbox the place all the time, my neighbors knew what was going on, there’d be scenes outside like somebody screaming from the car at the person in my place or the time a guy threatened to shoot me in the face; I don’t know how it took me so long to get caught, honestly.”

A year into the guy’s full-time drug dealer dystopia, the aforementioned scene unraveled as the police raided his apartment and sent him off to jail. With offenses and evidence piling up, his lawyer visited him in prison to inform him their case was not looking so good and that he should emotionally prepare to face a twelve-year sentence.

Life Behind Bars

It didn’t take long for fellow inmates to nickname the fair-skinned, blue-eyed, and light hair having Dylan Caudullo, Justin Timberlake. The call sign worried him because he wasn’t sure what sort of potentially sexual suggestions it could imply, nevertheless, a day came when an incredibly massive man approached his cell, consequently walling off the exit. He proceeded to tell “Justin” he handcrafted some gift for him and pulled a fabric necklace clearly made of mutilated t-shirt remains out from behind his back.

“He tried forcing it over my head. I just started making intense eye contact and telling him, ‘dude, I don’t want your necklace,'” Caudullo vividly recounts; the inmate then became frustrated, shouting how sad he was that “Justin” wasn’t accepting his present. “He goes back to his cell then returns with this ring that he made and starts trying to get it on my hand. I’m just like, bro stop!”

When the man decided enough was enough, he quit trying and told “Justin,” he had just passed a test vital to his continued well-being. If he would have let him place the jailhouse jewelry on his body, he would have been known as weak and nobody would hesitate to beat him up or take advantage of him in unimaginable ways. Dylan gained the impression that this seasoned inmate was intending to share with him a survival tactic more than he was attempting to engage in malicious activity.

Further navigating the corrections system, he was frivolously paired with a physically humongous cellmate who obviously suffered from mental illness, this made Dylan uneasy as he contemplated what debauchery the usually gentle madman could be capable of. He’d be minding his business laying in bed – a thin mat stuffed with ducktape-like material, a razor-thin layer of feathers, that’s planted over a cold sheet of metal – on the top bunk, then all of a sudden, he’d notice his cellmate’s face creep over the edge whilst uttering the awfully familiar question, you want to hear a story?

“This guy would tell me the same repetitive story every time, just in different words,” he surmises. “Either there was a husband or father figure that beat his wife or the child the couple had together. Then my cellmate came into the picture, heard about what was going on, beat the man to a pulp, and got him arrested. Afterward, he’d stay over at the house and make love to the wife. Every time, it was this pretty much same thirty-minute story told in different scenarios.”

Fighting Off Depressing Thoughts

Aside from the occasional story session interruptions, being incarcerated left Dylan Caudullo with plenty of time to think about his rehabilitative circumstances. Although the first few days he was eager for a fresh start and chance to begin rewriting his life’s script, days turned into weeks, which caused once motivating thoughts to sometimes drift in a more negative direction.

“There were thoughts like, my life is over, nothing is going to work out, it’s been terrible so far, it’s just getting worse, I might as well end it,” he openly shares. ” But on the flip side, there was another part of me that wanted to be an inspiration to other people and manifest light out of the whole situation.”

Seeking knowledge, he checked out self-development books from the prison’s library – reading them restored his sense of hope for the future, in addition, journaling helped as well. About a month into being jailed, his lawyer returned with good news: he qualified for a probationary option called “treatment court” where if accepted into the program, he’d have to go to rehab for a month, then AA meetings every day for a year and a half, and also schedule a weekly meeting with his probation officer for six months straight.

Our distressed teenager translated the legal gab into one word: FREEDOM.

Dylan Caudullo is Released From Prison

His fellow inmates warned him that treatment court was a trap akin to getting handed a life sentence, however, Dylan took the deal, excited to experience life’s simpler pleasures like not having to starve due to scantily rationed meals, being able to sleep in an actual bed, and not having to be terrified by his environment every waking moment. The charges against him would be left pending until his completion of the program, and if he were to mess up, he’d be headed right back to the slammer.

“I was absolutely on point and super disciplined, which they had never really experienced,” he says. “Rehab was amazing compared to prison, obviously it sucks, but I was so happy to be out of a jail cell! After getting released from that facility, I moved back into my grandparent’s house and started trying to map out my next move.”

Law enforcement seized all of the money he had during the raid, leaving him no other choice but to start at ground zero. Dylan took a dishwashing job at a local restaurant, with every scrub, his thirst for something more than minimum wage grew. He started buying online courses to learn how to make money via the internet – his fierce conviction drove him to invest every ounce of those finite hours between soapy shifts into learning an entrepreneurial trade.

“I can’t go from kingpin drug dealer to dishwasher,” he’d mutter aloud. “My idea at the time was to start a digital marketing agency but then I thought about getting a sales position immediately. At least if I got paid off commission, that’d be a lot more fun than getting paid an hourly rate.”

Rather fatefully, after letting his probation officer in on the impending career makeover, she pointed him in the direction of a company that would be able to exceptionally accommodate treatment court’s demanding program. After getting hired thanks to his reference, on the first day, his new boss told him, “I don’t like you, I don’t think you can make this work, here’s the script and a list of leads, prove me wrong.”

The Rise of Dylan Caudullo

The company employing Dylan Caudullo at this point was a cold-call center that sold Sawzalls, blades that can cut through wood, nails, fiberglass, branches, plaster, masonry, and metals including aluminum, cast iron, steel, and even high-strength alloys. In order to function at its highest capacity, the blade must be attached to an electric reciprocating saw, which thrusts the Sawzall blade in a back and forth motion resulting in supreme slicing. With this being said, one may be led to fancy the sales team sold the very equipment the blades practically required for usage, but nope, they were just selling good ol’ boxes of blades to unsuspecting construction contractors.

“I started cold-calling and reading the scripts my manager gave me,” Caudullo humbly remarks. “I was horrible, I sounded like a robot, I would stutter, mess up the script, but somehow on the first day, I got a sale! Whether it was some higher power in the universe, I don’t know, something bigger than myself must have helped me out there. Then my boss told me, ‘okay, you got lucky with one sale, let’s see if you can do it again.'”

What really irked the teenager’s boss was Dylan’s dress and demeanor – we’re talking button-up shirt, well-groomed physical appearance, and displays of cleanliness accompanied by manners. Contrastly, their shared workspace looked like a tornado thrashed through it, leaving trashy debris piled around the close quarters, what’s more, most of the other folks employed there were on probation as well and tended to dress in tattered, unprofessional clothing. The bottom line, this poor fellow just didn’t fit in.

Be that as it may, his work ethic and exceptional production were second to none. Although the job demanded a traditional nine to five work schedule, he came in an hour early and stayed for hours after others already clocked out, taking full advantage of the fact America’s west coast still had daylight left, along with further business potential. Truthfully, it didn’t make sense to him why people bought the product from them in the first place, nonetheless, he eked out enough money to gradually surpass his grandparents’ combined income.

“It was strictly commission-based, with no guaranteed pay,” he notes. “Orders started to get kicked back though. Meaning, we’d send the blades out on credit and expect customers to pay over time and if they didn’t do so, then the salesperson had to take on return shipping costs and forfeit their commission back. A few months in, a lot of orders began getting kicked back as clients wondered, ‘why in the world did I order this box of blades?’ Frankly, I don’t blame them, after looking the product up online, I found that people could easily get them for nearly half the price we were selling the blades at!”

Founding a Marketing Agency

Now that he was back on his feet financially, had paid off all leftover, pesky legal fees, and saved up a total of $5,000 Dylan Caudullo looked forward to making another big investment in himself. He had purchased all kinds of online courses in the past, however, they never seemed realistic or he just didn’t apply the knowledge correctly, whatever the case may have been, those educational resources always seemed to lead to some inevitable dead end. Then he stumbled across a man that’d become his first mentor.

“When they called me, it was the way they communicated, the questions they were asking, and how they got me interested,” he remembers. “I thought, I don’t know what their program is about but if I could just learn from these people how they communicate with other people, then I will be set for life! No matter what happens, if I can do what they’re doing to me right now, I’ll be good.”

As he made his willingness to buy their content clear, a male voice over the phone informed him the course material cost $5,000 and proceeded to outline payment plans assuming the nineteen-year-old didn’t exactly have that kind of money laying around. Dylan cut him off by saying, let’s just do the five G’s. Following the transaction, as he was later told, the whole call center lost their minds and freaked out, with a handful yelling, that kid was cold-blooded! Two weeks into the program, he earned a pair of clients who signed onto independent four-figure contracts with his brand new digital marketing agency, one compensating him $2,000 per month, and the other $1,500 a month.

Despite his recently acquired, effective sales tactics, he struggled to retain clients because there was no adequate training made available on how to run social media marketing campaigns; in other words, the goods got sold, but not delivered. Customers rarely received the results they were promised, questioned the operation’s legitimacy, and ultimately stopped making payments as soon as they saw fit. Going about business this way seemed unsustainable, so Dylan got on the phone with his mentor, who then flew him across the country to San Diego for a week’s worth of more intimate instruction.

Considering he was still on probation at the time, it was a miracle law enforcement allowed him to leave the state, and then he’d need divine intervention once again when those seven precious days crept to a close. He craved one more week with the team in California and he, his mentor, along with another colleague drafted proposals for his probation officer explaining the necessity of the learning experience.

“They gave me an extra week,” he thankfully recollects, just before revealing the perplexing effect a pandemic would have on his life’s orientation. “COVID blew up, everything started shutting down, and the plane ticket I had got canceled. It was impossible to find another flight!” The lawful supervisors back in Pennsylvania understood that he had no choice but to stay put until further notice and patiently waited for a reasonable solution to his unprecedented dilemma to surface.

Dylan Caudullo Moves to California

A shimmering California dream in the making, Dylan Caudullo sold the modest digital marketing agency he owned to a colleague, then proceeded to sell his mentor’s training and ads services that were geared towards fitness professionals. Months would go by, eventually compelling his probation officers on the east coast to again ask, when he planned on returning. They were not aware he had to lease an apartment in the meantime – obviously, there was no way this resourceful twenty-year-old was going to live on the streets for months while the world sorted itself out.

Due to his successful “rehabilitation,” he earned the right to graduate from treatment court, however, was informed that he needed to be in Pennsylvania for the ceremony. Traveling back home was simply not a possibility and a judge later approved his proposal to graduate virtually, forever absolving Dylan of his henceforth distant, nefarious past.

“When I initially made the decision to move into my new apartment, I couldn’t really afford the rent but I figured that would force me to produce more income, which it definitely did,” he says. “I wasn’t even very good at sales, I’d just get so many people on the line every day that somebody would eventually say yes. I had no skill, it was pure work ethic – I’d clock in maybe seventy to eighty hours per week. At the onset, I barely made enough money to survive another month.”

Perhaps his tireless attention to the desirable quest at hand has something to do with the very same addictive personality that once hindered him. What many would consider a flawed character trait – which started with meaningless video games, resulted in marijuana addiction, and climatically had the guy caged up like an animal behind bars – was brilliantly reverse-engineered and purposefully transfixed on our inalienable right to the righteous pursuit of happiness.

“At the time, I could go work at McDonald’s and secure more money for the hours I was putting into sales,” he admits. “I did the math, I was making like seven or eight dollars an hour for the first month or two, which is drastically less than California’s minimum wage! I just knew, if I didn’t quit and kept at it, I’d wind up making a bunch of money.”

Launches a Course

A sales manager position came calling, all of a sudden, Dylan Caudullo was responsible for hiring employees onto his team. In order to discover fresh talent, he searched countless Facebook groups that could have had prospects, eventually stumbling across one with thousands of members eager to master the art of closing sales. After publishing a single post on the forum, describing the kind of money he was generating, hundreds of people began commenting and DMing him, inquiring for further information.

Overwhelmed with a tidal wave of responses, he relayed the event to his mentor, who then developed a specialized $5,000 course for this burgeoning social media demographic. Dylan understood the virality of his rapidly unfolding situation was too good to pass up, therefore, he established an entirely new division, within the company he worked at, that’s soul mission involved educating these largely facebook-derived clients on closing sales. He ingeniously fanned the attention-drawing flames of their novel operation when informing course participants, if they were to refer another paying student then they’d get paid commission on that sale.

“For $5,000 people would get unlimited access to the course material, job placement assistance, and a weekly training call with myself for a whole year,” he outlines. “In the first forty-five days, we did over $1,000,000 in sales. My mentor tried telling me to handle that kind of high volume all on my own, I said no, Sean Adams is coming with me. Adams and I are an amazing duo, he’s got an incredible work ethic!”

The company couldn’t adequately deliver on the scale of its fresh team’s phenomenal production, which meant some clients inevitably fell by the wayside and began posting complaints online. Things got to the point where Caudullo realized he was providing nearly all of the intrinsic value for customers by answering questions and helping clients out via weekly training calls. His frustration grew over the fact these students he spoke with on a daily basis weren’t quite getting the supportive resources they deserved. “When people are paying that much money, they need to be taken care of as much as possible,” he believes.

Dylan Caudullo Goes Solo

Revisiting a recurring theme in his life, Caudullo’s ethical concerns inspired him to seek more knowledge, and hoping to fix the unorganized situation on his own, he enrolled in an Ohio-based, in-person class teaching business management. There, he’d arm himself with the tools requisite for arranging an immensely effective internal business structure. The company he worked for brought in somewhere around $100,000 per month when he first arrived, now his division alone produced $2,300,000 in sales over the course of a single month; needless to say, this twenty-one-year-old was at the center of something special.

“I was out in Ohio and I just wanted to become better as a person, whether that was in sales or personal development,” he reveals. “It [the course] really expanded my awareness, I thought, I don’t have to rely on other people in order to create in this world. I came to the conclusion, I wanted to be completely at cause for everything in my life, and working for somebody else’s business was not conducive to that goal. I decided I’d branch off and do my own thing.”

Amidst a snowy rust belt winter, in February of 2021, Dylan Caudullo closed the first two sales of his solo career before phoning his mentor to inform him, he quit.

Adventure of a Lifetime

Bad news trickled in the next day as apparently a number of peers who he understood were going to leave with him changed their mind after the owner of that company, his mentor, soberly reminded them who signs their dependable paychecks each month. Stepping outside a classroom mid-lecture, he called several characters he had encountered in the past, everybody was on board with the vision, and just two months into their venture together, they’ve generated north of $1,000,000 in contract sales; back at the division he formerly ran, insider sources report that sales have substantially declined.

“I don’t just have people watch video courses, they actually train with me live,” he explains, while also noting the early mental challenges he helps students overcome. “When you get started in sales, it’s kind of like starting your own business, for most people like myself it can be a struggle in the beginning, you’re putting in a lot of hard work and not getting much out. But if you can stick through that difficult period, it’ll be worth it in the end.”

Dylan Caudullo invaluably adds, “the actual prospecting and lead generation is way more important than your skills as a closer. If you don’t have the ability to manifest interest and get new people in front of you then it doesn’t matter how good of a closer you are. I tell my students all the time, outflow is the most important thing when you’re getting started; reach out to folks and put those communication lines out there so much so to the point that the universe has to give you something in return. Results will always come back as long as you keep flowing out.”

Let it be known, it was on the heels of drug addiction, an unquenchable thirst for knowledge, and the paralyzing societal effects of a global pandemic that harmoniously afforded one man the destined opportunity to reclaim his life. Imagine that, a fortuitous flight to California for a brief week-long stay turning into the adventure of a lifetime, or at the very least, something as simple as a fresh start.


If you enjoyed this story on the life of sales coach Dylan Caudullo, be sure to check out the time Benjamin Franklin ran away from home at seventeen years old.

For further media coverage of Dylan Caudullo, here is a recently published article he’s featured in by the Washington Post.