High School dropout to 60k…the story of my friend Isaac

Colby Foster
10 min readDec 3, 2017

Dropped out of high school at 16? Thats okay, you can still get your income to $60k…

My friend Isaac went from delivering sandwiches at Jason’s Deli to managing a team that produces millions of dollars in sales per month. Raised by a single mom, Isaac dropped out of high school at 16, went broke 3 times, and bounced around the restaurant industry for almost 10 years before landing a professional job that got his income past $60,000.

How did a food delivery guy go from dropping out of high school to being a manager in the professional world?

He was consistent enough and persistent enough to stay hungry through adversity. Isaac didn’t start off life making the best of choices, but his choices got less worse over time until he finally broke through the cycle that keeps so many down. Isaac never allowed himself to be a victim and is now building the life he always wanted with the woman of his dreams. I hope you enjoy reading his story as much as I did hearing it!

Listen to Podcast: iTunes, Stitcher, SoundCloud.

Favorite Quotes:

”I was a lazy deadbeat”

“I don’t have to do the trend that everyone else does.”

“I still had some of that laziness inside of me. I had not yet worked that out of me yet. (min 24). I wanted to make more money, but i didn’t know how, and Iwasn’t hungry enough to do it.

“learn what your manager is looking for.” (min 32)

“With a strong work ethic and a desire to serve and love people, you can put a roof over your head” — Colby

Top Takeaway

In minute 32, Isaac gave us insights into his greatest skill… discovering what people want and giving it to them. His stories of how he wooed his managers in the restaurant industry clearly translated to his success in the real estate world. My favorite quote was, “in every relationship, focus on making the experience highly pleasurable for the other party… your main goal is for the other individual to enjoy that interaction”

High School Drop Out

Isaac’s mom and dad got divorced when he was 5 years old. He grew up in a single mother household with not much income. At age 16, he dropped out of high school. Isaac recalled, “I was a lazy deadbeat. I loved to just hang out and do nothing. I had no drive.”

First Job: Food Delivery Guy

By age 18, Isaac knew he didn’t want to be poor anymore. As soon as he was old enough to vote, he moved out of his house and started working as a food delivery driver at Jason’s Deli. He had learned how to befriend the head honcho who set the schedules and assigned the routes for all the employees. This allowed him to work the most profitable shifts. Isaac was living the good life and was making around $2,500 bucks a month due to tips!

Isaac worked 30 hours a week at $7.00/hour + all the tips he could make. It was a lesson to him that if he performed better services and made pepole’s experience with him pleasant, he would increase the odds of him bringing home more money.

Lessons Learned at Jason’s Deli:

  • Befriend the head honcho
  • Whether you like someone or not, you have to suck it up and deal with it.

“I learned how to read people and judge their facial expressions to see how they are reacting to what I’m doing or saying. [I learned] the humility to step back and understand frustrations and figure out how to resolve them.”

Working 2 Jobs

Isaac landed his first job outside the restaurant industry through happenstance. He was selling an old car and sparked up a conversation with the buyer. Turns out the buyer was a hotshot in a mortgage company and was willing to bring Isaac on as his personal assistant. Leaping at the opportunity, Isaac said yes and started spending his days getting his new boss coffee, sorting papers, and taking notes…pretty much anything his new boss wanted. At night Isaac was still working at Jason’s Deli.

Isaac spent 2.5 years in this job and used his knack of befriending the boss to start training to get his mortgage license in hope for career advancement. Isaac was underpaid as an assistant and because he didn’t have the “money shifts” delivering food anymore he was barley scraping by financially.

Isaac finally stopped working both jobs when a friend of was able to get him a job making $13/hour at another morgage company. His past skills in the industry and his refined people skills allowed him to contiue to prosper inside the professional world.

Outworking laziness

In Minute 24 with Isaac he said this amazing line, “I still had some laziness inside of me. I had not yet worked that out of me yet. I wanted to make more money, but I didn’t know how, and I wasn’t hungry enough to do it.”

Work the laziness out of you? I think this is a paradigm shift for a lot of people and it’s one of the key reasons I feel Isaac has had so much success in life. He understands that action creates feelings and rarely do feelings create lasting action. Although in his early 20’s Isaac probably wasn’t making the best choices in life, he was still doing something.

A mentor of mine wrote a book called “Real Power”. In this, he quotes, “It is not enough to nurture strong feelings; we can only effect change by doing.” — Real Power page 26

Rock Bottom…Again

Isaac got let go during “The Great Recession”. He hit rock bottom, was jobless and ended up moving back in with his mom for the second time. He couldn’t even afford $208/month car payment and had to sell his car to his mom in order to makes ends meet. Having no where to go, Isaac turned back to the food industry and got a job making sandwiches at a place called, Just Fresh. At this point, Isaac started to want more out of life and knew he had to make a change.

Wisdom in the Trenches

Isaac has a knack for befriending his boss at every place he works. As per his speciality, he described this process to me and it was per gold!

“you’ve got to learn what your manager is looking for (min 32). No matter what industry you are in, you are always serving people.”

Isaac explained to me that even if you serve people with a selfish motivation, you are still serving them and thats okay.

He quotes Adam Robinson from the Tim Ferriss Show saying, “In every relationship, focus on making the experience highly pleasurable for the other party. Your main goal is for the other individual to enjoy that interaction.”

Turning Point #1 — Promoted to Management

Isaac worked really hard at Just Fresh and ended up becoming a manager. He was making around $25,000 a year. The only step up from his position was the GM who earned around 50k. $50,000 a year was not Isaac’s goal in life and this was a turning point. He realized he didn’t want to continue this cycle throughout his life but didn’t really know where to go.

Getting Fired

Isaac ended up getting fired from Just Fresh and was forced to move back into his mom’s house for the 3rd time. Looking back, he says this was one of the best things that happened to him because it caused him to get busy. He started attending community college full time and called in a favor from a friend to get him hired at a restaurant called, 131 Main.

At this point, Isaac had been working for 6 years in different jobs and his income still hadn’t crossed over $30,000 in a single calender year.

Through these 6 years, he had learned a lot about people and had developed a strong work ethic. The year was 2012 and Isaac was 24 years of age.

Next Step

Isaac had a good job at 131 Main and with the tips and high price points, he was now making more money than he ever had made (around $3,000 per month).

One thing I loved about talking to Isaac was that he is a person who realizes he controls his own destiny. I remember him saying “I want to get there, but I’m not putting all the effort”.

At 131 Main, Isaac was making $2.13 / hour but averaging $100 in tips per shift.

One Step Back, Two Steps Forward

$3k a month is good for most people, but Isaac wanted more. Issac realized that in order to make more money himself, he was going to have to become more valuable to the company and also grow his skills. To propel him forward, Isaac cross trained at his job and learned how to be a bartender.

He took a pay cut in the short term with his income falling to $7/hour and no tips. His leap of faith paid off and within a few months he was an official bartender and was surpassed his 3k month income at the restaurant.

Turning Point #2 — First Mentor

The year was 2012 and Isaac was 27 years old. Into to the picture comes Christine (future wife) and into the picture comes Christine’s father. The father, Joseph, helped shaped Isaac and molded his life toward a more religious one. He stopped working on two days a week but worked 9am-10pm on another day to make up for the lost income.

First Professional Job

At 131 Main, Isaac impressed one of his customers so much that he got a job offer out of the interaction. The gentleman worked for a recruiting firm and his department was responsible for IT recruiting. Isaac knew sales and was a natural with people. He followed up properly and before he knew it, had his first every professional interview. Isaac nailed the interview and was somehow able to negotiate a salary of $50k per year base salary with potential for bonus and commission. It seemed like his days of waiting tables was finally going to come to an end and he could get married.

Back to Waiting Tables

In the first week of his new job, Isaac realized he was in over his head. He worked for this firm a whole 7 days before quitting due to be too overwhelmed. Isaac quit with dignity and was honest and respectful with his boss. I think it was the right decision to leave as Isaac explained to me that he was getting physically ill because he was so nervous and didn’t know what he was doing.

Isaac was now back to waiting tables. His income went from 50k+ back to 30 and he knew being back in the restaurant industry delayed his timeline for marriage.

What’s Next?

One night, Isaac was sitting in his room and ask himself, “who do i know?” as he was trying to find a way out of his current income situation. Isaac started calling his friends to see if anyone had a lead on a real job for him. After a few calls, Isaac connected with a friend who knew a guy that worked at a mortgage company and they were hiring loan processors.

I really like the back story here of how Isaac had this relationship. It started with him “saying yes” to his friend Dean. He had helped build a fence for Dean’s brother-in-law for free and they bonded over BMW’s. Dean’s brother in law referred Isaac to his friend Matt and Matt referred him to Wyndham Capital to apply for a job as a Loan Processor.

Crossing the $60k Threshold

Isaac interviewed, passed, and the company told him to make a decision in 24 hours. Isaac accepted to job and left 131 Main for the last time. The position of a loan processor was his intro into Wyndham where he still is today. So how did he get to 60k?

He worked his way up to being a Loan Officer Assistant and had a salary of $30,000 per year. Due to the bonus structure and the companies success, Isaac brought home $60k his first year. Isaac married Christine shortly after this.

After a year, Isaac took over for a manager at the company who got fired and performed well enough to keep the job. This put his salary at $55,000 and his bonus put him around 80k!

Conclusion and Advice:

  • Do a lot of studying.
  • If you want to advance your career, you need to have a way of getting there.
  • Create the desire to study
  • Create the desire to invest in yourself.
  • Quote from Jim Rohn, “you can always go to work and earn a paycheck, but if you go to work for yourself, you will earn a fortune.”
  • If you truly want something, you’ve got to work for it.
  • Be hungry to advance yourself.
  • Don’t come to work just for a paycheck.
  • Sacrifice and make the company and yourself better.
  • One book: “The Miricale Morning”
  • Don’t sleep in, wake up early!

Time Stamps

  • Dropped out of high school at 16. [1:32]
  • Got GED and started community college [5:06]
  • Moved out of house at 18 [7:33]
  • First Job at Jason’s Deli [8:17]
  • How to befriend the manager at your job [12:28]
  • Meets successful mortgage bank when selling his car [17:03]
  • Get opportunity to become a Mortgage Loan Officer [19:00]
  • Working out the laziness within [24:40]
  • Moved back in with mom for the second time [28:08]
  • Working at Jason’s Deli making sandwiches on the line [31:03]
  • (Business) Relationship advice [33:41]
  • Get’s promoted to Manager at Just Fresh [36:20]
  • Moves out of moms house [38:30]
  • Get’s Fired from Just Fresh [39:00]
  • Calls in a favor from a friend to get a job waiting tables at 131 Main [40:29]
  • Making 3k month as Waiter [43:21]
  • Cross Trains to become bartender to earn more money [47:00]
  • Meets Wife [50:32]
  • Meets first Mentor (father-in-law) [51:02]
  • Can’t get married while working at a restaurant. [54:47]
  • Get’s first real professional job [57:18]
  • Signs on at $50,000 to be a headhunter [59:17]
  • Quits new job after 7 days [1:00:00]
  • Becomes a Loan Processor making $30,000 [1:18:22]
  • Gets past $60k [1:29:00]
  • Shout Out to Isaac’s Mom! [1:30:21]
  • Advice and favorite book [1:35:21]



Colby Foster

I really admire people who can think through ideas. I hope you will join me to help me think through my own.