June 20, 2016
Everything I Know About Entrepreneurship, I Learned From my Dad

A version of this post originally appeared on Forbes.

I’m always fascinated about people’s backgrounds, their upbringing, and how their parents’ work influenced them as kids. I believe this foundation sets the groundwork for someone’s own professional journey.

I’ve wanted to interview my dad for years about his entrepreneurial journey. Since yesterday was Father’s Day, I figured there was no better time than now.

I’m lucky. Dad, who is 73 now, suffered a severe stroke two years ago and it’s pretty much a miracle that he’s able to live independently in Florida. It’s also a miracle that his brain continued to heal and he’s still able to remember so many details of his past.

Here are a few of the most significant lessons my father taught me about entrepreneurship:



My dad was born in 1943 during World War II. He never met my grandfather, George Cline. Grandpa George was a Merchant Marine - part of the maritime crew that brought supplies to the soldiers during wartime. His freighter was torpedoed by a German submarine. There were no survivors.

Losing your dad before even having the chance to meet him is hard. Add to that the considerable financial strain my grandfather’s passing placed on the family. The Merchant Marines aren’t part of the armed forces, so my dad’s family did not received any pension or financial benefits from the military. They were just eligible for his social security. My grandmother was already working as a secretary trying to make ends meet, since she had two mouths to feed.

Dad grew up in Newton, New Hampshire, in a house with no electricity, running water, or bathrooms. Instead, there was an outhouse - which was very uncommon in the 1940s. The house was heated with a coal stove and during really cold nights, my dad would heat up bricks and bring them to bed to keep warm.

Dad’s family had limited financial resources, so he knew that hard work would be the only way to help pay for things that his family needed. As an adolescent, he worked a variety of jobs, from running a paper route after school for the Haverhill Gazette, to cleaning out cages at a chicken farm.

Lesson Learned: Hard work is the foundation of success and can help you overcome the obstacles or limitations that might be in the way.


Dad graduated from high school in 1960 at 17 years old. He got a job at a company that manufactured T-shirts. He was hired as a flocker, which meant he would put the finishing touches on a -shirt after the screen printing process was complete.

The company lost an employee responsible for cutting the cloth for the T-shirts shortly after my dad was hired. His manager asked Dad if he’d be interested in assuming these responsibilities. My father was eager to learn, so the decision was easy. Things went well, until he cut his thumb. The company was worried about their liability since he was under 18. Dad didn’t want to lose his job, so he ended up bandaging his thumb and didn’t bother going to the hospital.

Following that job, Dad worked for about seven years as a cutter in manufacturing before trying out a new profession: sales at Prudential Insurance.

During his three years at Prudential, he learned how to communicate with people and how to establish personal relationships. He also saw that his boss was greedy, taking advantage of people by up-selling them on insurance they didn’t always need. My dad always wanted to help people and felt that looking out for his customer’s best interest was the right thing to do. He didn’t feel right about his boss’ sleazy tactics and decided to move on.

At this point, Dad was 29 years old. He went back to what he knew best: the manufacturing industry. After cutting cloth to make golf shirts at Malden Mills, he landed at Star Sportswear, a company that which made leather coats. There, he met his future business partner.

Lesson Learned: Gain as much experience in different job functions as you can to round out your experience. It will only help you in the long run and support you in settling into what you love to do.


Dad knew that he could continue his career at Star Sportswear, but the only way to make a good living was to go out and start a company. So, at 31 years old and with three kids, my dad took a huge risk and started Vagabond Leathers with his business partner.

When starting the company, my dad continued to work full-time and earn a paycheck, while his partner went out and sold leather neckties. As orders would come in, both of my parents would make the neckties in the playroom of their home at night.

Lesson Learned: Starting a company is difficult and a major risk. Offset the risk by moonlighting in the beginning to see if your business will gain some traction.


Vagabond Leathers soon expanded and began making leather bowties and hats. But my dad and his partner knew the best opportunities were in manufacturing leather coats, as the price point was much higher.

Once things started humming, my dad converted a building he owned into a factory and started hiring employees. My mom did her part in terms of helping get my dad’s business off the ground by working long nights as a bartender, so they could keep our family fed.

Lesson Learned: You might start out doing something smaller (like Dad’s neckties) than what your business ends up being over the long haul (like Dad’s leather coats). It’s ok to start small and work toward a grander vision.


The leather coat business is tricky to run. Most of the sales are at the end of the year, but coats need to be manufactured all year long. This means purchasing materials, paying for labor, and building up inventory until the coats are delivered to the retailers. It also means floating a lot of capital until invoices are paid.

Dad and his partner found it difficult to find someone who believed in their business and would give them a line of credit to keep operations going. After pitching many local banks, they finally found one banker who believed in them and set up a line of credit they need to be successful.

This credit allowed them to establish operations in a 7,000 square foot manufacturing facility at the Amoskeag Millyard in Manchester, New Hampshire. Over time, they doubled the space’s size and grew the business from scratch to over 25 employees. Eventually, they established a multi-million dollar business, primarily selling coats to East Coast retailers - including a store at Disney in Orlando.

Lesson Learned: It might take a lot of hustle and a lot of “no’s” until you finally find someone who will either invest in your business or loan you money. Don’t give up.


After working together for 10 years, Dad and Charlie decided to parted ways. My dad decided to stay in the leather coat business, so he purchased a lot of manufacturing equipment from Vagabond Leathers and set up a new company: Classic Escape.

He ran the company for three years, but after losing money each and every year, he decided that the manufacturing industry wasn’t the right space to be in anymore. He couldn’t compete against manufacturing overseas and closed down his business to pursue opportunities in real estate.

Lesson Learned: Maybe you’ve lost out to the competition or your business just isn’t scaling as it should. Be honest with yourself and make some hard decisions based on the reality of your business - which might require you to pivot or even close up shop.


I’ve never seen my dad work for anyone but himself. He’s the true definition of an entrepreneur. I saw the hard work and the long hours that he put in, which at times was a sacrifice for our family growing up.

My parents taught me many life lessons, but one of the greatest was about the value of hard work. Beginning at 9 years old, I was responsible for cleaning the leather coat factory every Sunday. Cleaning the 14,000 square foot factory included everything from picking up leather scraps, to vacuuming the floors, to cleaning the toilets.

I remember one summer when I was 15 years old, pressing coats because the work needed to get done. Working behind a steam presser on a 90 degree day is not my definition of a good time, but it taught me about working hard. I am grateful that my parents instilled this trait in me at a young age.

Starting a business from scratch isn’t an easy feat. I witnessed my father’s ups and downs as a kid and today experience them firsthand with my own business. Entrepreneurship is in my blood, though, and I’m grateful for the lessons I learned through my father. My daughters have never seen me work for anyone but myself, and I hope my efforts one day inspire them to follow in our family’s entrepreneurial footsteps.


Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.