In 1985, I was born in Boston, Massachusetts. Twenty-seven years before I sold my first company. We lived in a small 600 sq. ft apartment just outside the city until I was 3 years old. After moving around a few times, at the age of 6 my parents decided to settle down in the small town of Greenland, NH with a total population of 3,208 people. Most of the surrounding area was used as farmland for growing crops and raising cows. It had a small town feel, with a strong local community; a great place to raise a family.

Throughout my childhood, I was surrounded by entrepreneurs. All of my uncles on my moms side owned their own businesses. My grandparents owned and operated multiple mobile home parks. My dad worked as an independent IT consultant for universities and larger corporations. For years, he commuted over 1.5 hours each way to work. To earn extra income for the family, my mom started her own interior design business. Both my parents worked very hard and made huge sacrifices to enable my sister and I to live a middle class lifestyle.


By senior year in high school, my dad had transitioned into a full-time position at Boston University. Due to his employment there, if I was accepted, my college education would only cost 10% of the full tuition. Even though I was an average B student throughout high school, I got accepted. In the hopes of gaining an appreciation for the value of education, I decided to defer enrollment and take a year off.

I wanted to be a ski bum. I took $800 dollars Id saved up from my summer jobs and drove across country to Jackson Hole, Wyoming with a friend of mine. To get a free ski season pass, we had to work on the mountain. Butwhen we arrived, all the jobs at the ski resort were taken. After 3 weeks of jobs hunting, we were nearly broke. Living in a one bedroom motel room, eating ramen for breakfast, lunch and dinner wasnt what I had imagined. We were desperate.

With only $200 left in my bank account, we heard two housekeeping positions just became available at the local hotel. We took the jobs! And for the next five months, we vacuumed rooms, made beds and cleaned toilets. But, when we werent working, we skied powder up to our chests, drank PBR (beer) and chased the local ski bunnies. It was one of the best times in my life.

After the ski season ended, I finally understood the distinction between poor freedom and rich freedom. I worked 35 hours a week and only made $230 after health insurance and taxes. Most of my food came from hotel room fridges and cupboards that people on vacation left behind. I was totally broke, but could ski and party with friends every day of the week. That is poor freedom.

I wanted rich freedom. Ill tell you more about this later.


When I returned home to attend college in 2003, the internet bubble had completely collapsed. Stocks were at all time lows, and the economy was in a deep recession. My dad was laid off. I would no longer receive a 90% discount on tuition. Suddenly, I went from having to pay $4,500 per year to $45,000. Between the generosity of my parents and grandparents, I had just enough to cover 1.5 years of school. Then I would be stuck with student loans of $115,250 at the end of four years.

Thats a lot of money!

I had to find a way out of this future financial hole. Freshmen year, I was on the rowing team. My 6 foot 4 inch, athletic build served me well. We practiced 2 hours every morning from 5:30am 7:30am before class, then 2 more hours in the afternoon from 4:30pm 6:30pm. Rowing is considered a spring sport, but we still compete in the fall and train indoors throughout the winter. It never stops. Guys even go to training camps during the summer. I worked. At the end of freshmen year, I was ranked top 1 or 2 on the team. I knew four of my teammates recruited from Canada, Germany, and Australia were receiving full-scholarships to row. Three of them were ranked below me. This was the best way out of financial hell from student debt.

Throughout the entire year, I worked so hard to prove my athletic ability and value to the teams performance. Now I needed my coach to really see it. So on a sunny spring afternoon, after my first rowing season ended, I walked into my coachs office to ask for money. A lot of money. Forty five thousand dollars. We talked for nearly two hours. I illustrated my full value, supported by facts and metrics of my performance. I explained the alternative. If I didnt receive scholarship money for rowing, Id have to get a job instead.

I promoted the SH*T out of myself.

And…guess what? Soon I became a full-scholarship athlete. I had done it! He made the ultimate decision, but I influenced the outcome. And Im so grateful to have received the funds because I graduated without a penny in student loans.

What if I never had the courage to ask?


Throughout college I never knew what I wanted to do. More importantly I didnt know who I wanted to become. I just wanted to make a ton of money and be perceived as hugely successful. Remember I learned I didnt want poor freedom. So at least I knew I had to get rich.

Nearly five years had passed since the last recession. The unprecedented rise in the housing market fueled our economic recovery and growth. But as we all know, this period of euphoria was short lived. At the time of my graduation in 2009, the financial crisis plunged our country into the worst economic recession since the Great Depression in 1929. Companies stopped hiring and started laying off over 100,000 people per month. In total, 7.9 million people lost their jobs.

Well, I majored in finance. And this was the worst time to find a job, especially in finance. Either way I had to try. I interviewed at 11 different firms senior year for full-time employment. Accounting firms, consulting firms and investment banks. Of all the jobs, I knew investment bankers make the most money. So thats what I really wanted. And some of the interviewers picked up on it.

When I interviewed at one accounting firm, the Vice President with a stern look asked me, why do you want to be an accountant?

It felt like the thermostat was suddenly cranked up to 170 degrees. This most basic interview question seemed like a complete curve ball. Beet red in the face, I mustered up a response, well sir, because I like the validity of data. Yeah, right. I didnt get the job offer. I say dumb things in interviews when I dont know what I want.

Nevertheless, I was persistent. I received one offer. From one investment bank. It felt like my greatest accomplishment in life to date.

I was an investment banker for 3 years. Every year was grueling. As an analyst, youre expected to stay in the office at least until 11:00pm every night Monday thru Friday, weekends too. Most nights you work until 1:00am or 2:00am. You live in excel spreadsheets and powerpoint presentations.

Many nights in the cab ride home, Id ask myself what the hell am I doing with my life? These types of introspective questions usually arise when youre not making decisions for the right reasons. My primary motivation was the money. Where else could I make over $100,000 a year at 23 years old?

I had accomplished my near-term goal of making a lot of money. But soon realized money doesnt go very far when youre buying bottles at clubs, eating steak dinners, and flying to Vegas on weekends. It also doesnt make you happy. Ill write a post on this at some point. Fortunately, I had the sensibility to save some money. And after three years, when the lure of money no longer outweighed the pain of doing something I hated, I quit.

Some say never quit. My grandfather says, Know when to hold them, and know when to fold them. I was ready for something new.


I woke up the next morning to a sense of complete freedom. No boss telling me what to do. No corporate culture shaping my behavior. I suddenly realized, Im 26 years old and I can do whatever the f*ck I want.

Have you ever felt freedom like that?

So I started a company. When you start a company there is no blueprint. No one tells you what to do, how to do it, or what direction to go. Therefore, you are forced to use your mind. Forced to think of ideas, identify problems, create solutions. The company, my co-founder and I started was focused on helping home owners find trusted estate liquidators. In the event your parents die or you downsize your home, you would typically need to sell everything. Its a higher end yard sale. People are taken advantage all the time because its a cash based business and most of us dont know what grannies vase is worth.

Within 3 months, we worked with customers across seven states in the US. But..it didnt take long to realize I wasnt passionate about marketing to 65+ year olds. So we made the difficult decision to shut down the business.

Only two months later though, I started my second business. This time, we built a marketing platform for event organizers. Within 2 months, we had over 500 people signed up to use our product. I told everyone I knew about it, and their friends. At the early stages of a business, you are promoting yourself before the business. People have to buy into you first because their is no product. Its only an idea.

Even after initial traction, I began to disbelieve in the long-term vision. The market was fragmented, competition was growing, and customer budgets were tight. After 10 months of growing the business, I wanted out.

The good news: I had a valuable asset. This baby was worth something. I found a buyer that wanted the software code and the visitor traffic to our website. After one week of negotiations, we settled on a price. My first company was SOLD! It was by no means enough to retire on. But it was 5 times the amount of money I invested in the business and one hell of a good feeling.


Now, Im writing to share my stories with you. Its fun for me. It helps me improve my craft and reflect on my personal experiences.

Why do I write about self-promotion in business?

What I discovered, is that people perceive you however you present yourself. Even if you dont think youre in sales, you are. You sell people everyday. You sell people to pass the ketchup, pickup the dry-cleaning, clean the dishes, print the documents. Next time, before you ask someone to complete any of those tasks, call them a HUGE A$$HOLE first. See how theyll still do it.

Whether your job is in sales or not, doesnt matter. You are in sales. You influence people everyday.

You know why sales professionals have a bad reputation?

Its because the last time you were sold on anything you probably didnt realize it. A good sale occurs when you want to buy. The sales professional merely helps you make the decision. As humans though, we are powerfully effected by a negative experience. When any event is paired with a strong negative emotion it becomes tattooed to our brains. Therefore, we really only remember the bad sales experiences. The sales guy that pressures you into buying with sleezy closing lines evokes a strong offensive and irritating emotion. Versus a good sale call, which evokes enthusiasm and excitement for the product not the individual.

The saying goes, people like to buy, not get sold.


The number one most important factor in life is our health. In Maslows hierarchy of needs, the most fundamental needs pertain to health. Breathing. Food. Water. Without these elements, you will die. Until you satisfy these needs, you de-prioritize all other needs. Security. Love. Esteem. Self-Actualization. For someone who is scared of public speaking, but hasnt eaten in 3 days. Try putting a bowl of fruit, center stage in an auditorium of 10,000 people. I promise you, they will walk out in front of everyone. No problem.

We pay such close attention to our most fundamental needs because our natural instincts take control in desperate times. But once we satisfy this fundamental need, we no longer have the luxury of relying on our instincts. We must use our minds to make decisions to achieve higher level needs.

I am writing about self-promotion in business because it is the cornerstone of success. The Oxford dictionary defines self-promotion as the action of promoting or publicizing oneself or one’s activities. Whether you are looking for a job, a promotion, a vendor or a customer. You must tell people what youre all about. Even in your personal life. If you want to attract someone at the bar, you have to share your personal story. A little self-promotion.

Dont confuse self-promotion with vanity.

Dont confuse self-promotion with arrogance.

Dont confuse self-promotion with egotism.

Self-promotion isnt just about you. Its about helping other people get what they want too. If you developed the cure for cancer, wouldnt you want to share your activities with the rest of the world? Now is the time to start sharing your skills and experiences with others so everyone can benefit. And in the process, you will too.

Don’t hesitate to leave a comment here if you have any thoughts or questions. This is a chance to promote yourself right now.