7 Lessons My Dad Taught Me About Entrepreneurship

In today’s post, I will share 7 lessons my dad taught me about entrepreneurship.

My dad is a very successful entrepreneur in his own right. He’s been working for himself, living the American Dream for the past 30+ years. He and my mom have their own antique auction and self-storage business.

As a child, I watched my dad leave his job security to pursue his dreams and ambitions of being his own boss. By his example, I learned a lot about the mental toughness, guts, vision and courage someone has to have to give up a steady paycheck and take a walk into the unknown.

Because of his example, and the fact that I am also a free spirit, I decided to start my own business when I was 24 years old. I’ve been an entrepreneur ever since (18+ years).7 Lessons My Dad Taught Me About Entrepreneurship

7 Lessons My Dad Taught Me About Entrepreneurship 

What I would like to do in this post is share a few things valuable lessons my dad taught me about entrepreneurship. These are some simple, yet powerful lessons that really shaped my life and mindset. They are listed in no particular order. Enjoy.

# 1: Do Something You Love & You Will Never Work a Day in Your Life

My dad has never worked a day in the past 25-years. That’s how he sees it anyway.

Yes, he has done the physical work, but for him it is a labor of love. My dad loves people and he loves buying and selling antiques. He loves a good adventure. Buying antiques is like one big treasure hunt for him. He never knows what he will find, where he will go, or who he will meet.

I know that for the past 25+ years my dad woke up every day and loved to go to work! How many people can actually say that? I couldn’t imagine him going to a day job and having a boss tell him what to do. He wouldn’t survive one day. He’s a free spirit and wired to be his own boss.

By his example, he taught me that if you do what you love you will (1) never work a day in your life and (2) the money will eventually follow. Life is too short to do something you don’t enjoy.

# 2: Believe in Yourself

My dad is a confident guy. Not arrogant, just confident. He believes in himself and what he is doing.

Even before his business became profitable and successful he believed in what he was doing and he knew he would eventually succeed. I think that is one of the major reasons he became successful.

If you have self-esteem issues, get some help. If you have worthiness issues, get some help. You won’t make it long in business if you don’t believe in yourself. In addition, you must believe in what you are doing. You can’t fake confidence.

Confidence is one of the most important attributes of every successful entrepreneur that I personally know. Without confidence, it will be hard to find customers. It will be hard to get financing, and it will be extremely difficult to stay the course, even when things aren’t going your way.

Remember, people like to do business with confident people.

# 3: Businesses Take Years to Succeed

It took my dad nearly a DECADE to really build up some momentum in his business and get over the hump. During that time, he never wavered. Yes, there were times he had to do some temporary jobs to help pay the bills. But, he stayed true to his purpose and made it work.

Having been in business 18-years myself now, I understand this valuable lesson. It’s taken me over 10-years to really figure my business out and build something I can be proud of.

The bottom line is this: don’t expect to be an overnight success with your business. Rome wasn’t built in a day. Good things take time. Have some patience and persist UNTIL you succeed.

Most people who start a business have been employees their entire lives. They’ve grown accustomed to the work 40-hours get paid for 40-hours mentality. When they start a business and work hard, but don’t make much money in the beginning, they throw in the towel and quit.

Owning a business is much different than being an employee. You don’t get paid to show up. You only get paid to produce. You will work twice as hard for half the money your first few years in business. It sucks. But if you stay the course and succeed, it will be well worth it financially.

I have since learned that most businesses take a year or two to get profitable and five to ten years to become successful, and running smoothly (in most cases). You definitely need to take the long-term view.

# 4: Learn from Your Mistakes

No one is perfect and no business is perfect. My dad made many changes to his business through the years, from scaling his business up to scaling it down, to changing how many auctions he had, to what types of auctions he had, etc.

Not everything he did was a success. Learning is done mostly through trial and error. You try something. You learn from it and make the necessary adjustments.

My dad constantly reflects and analyzes on what is working in his business and what isn’t working well. He makes sure that every mistake is an opportunity to learn something new and improve.

He was never afraid to try something new. He wasn’t afraid to fail. Each action provided valuable new insights and lessons that would provide wisdom, experience and knowledge, which would benefit him greatly in the future.

A lot of people in the world have the fear of failure. I think we learn this in school. Failure is actually a good thing. It teaches us valuable lessons. In my own lifetime, I have learned that the only way to succeed is to fail, and fail, and fail, UNTIL you succeed.

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If you love what you do you will never work a day in your life ~ Popular Saying# 5: You Are in The People Business

Every entrepreneur is in the people business. Yet, some entrepreneurs don’t understand that.

My dad is naturally good with people and can make a new friend anywhere he goes. People like him, trust him and respect him. I learned that if you want to make it in business you have to be able to get along with people.

You need a good handshake, good eye contact, good people skills, and most importantly, integrity. You won’t keep many customers if people don’t like you. You must become likable and relatable.

Never forget that people like to do business with people they know, like and trust.

# 6: Have a Supportive Spouse

My dad is very lucky to have such a supportive spouse (my mom). My mom went back to work when my dad first started his business. That was tough for her, but fortunately everything worked out fine, and after a few years she quit her job to be a stay at home mom again.

I learned that having a supportive spouse can make all the difference to your long-term success and happiness. If your spouse is constantly nagging and complaining, you won’t be in business long (or you won’t be married long).

It’s also important to think from your spouse’s perspective and have frequent communication with them about how things are going in the business.

Choose your spouse wisely. They will have more influence on your life than any other person. Ideally, you want someone who is supportive and encouraging (make sure you are the same way with them).

# 7: Tweak and Change as Needed

One of the most important lessons my dad taught me about entrepreneurship is that businesses constantly change. So does the marketplace.

My dad is always analyzing and looking for new profit centers for his business. He evaluates what he does, determines whether or not it is working well, and then modifies his game plan as needed.

He is constantly living the slight edge principle (get a little bit better every single day). Over a period of years, this has given him a huge advantage over his competitors.

He still keeps his core business, but he changes his strategy from time-to-time. He looks for new opportunities for improvement and he seizes them. I encourage you to do the same thing!

About 10-years ago, he decided to add a “storage unit” business, which has turned out well for him.

2020 Update

My dad is now semi-retired. He will never fully retire (he still loves what he does), but he has cut back his work schedule to enjoy life and do more hunting, gardening, tend to the chickens, fishing, reading and relaxing. He also got a new pup (Pete), a Brittany Spaniel, in 2019. It’s nice to see my father relax and enjoy the fruits of his labor. Him and my mom are still happily married and approaching 46-years of marriage.

<noscript><img decoding=async class=wp image 16529 size full lazyload src=httpsonlinemlmcommunitycomwp contentuploads201508devant and grampajpg alt=dad width=400 height=533 srcset=httpsonlinemlmcommunitycomwp contentuploads201508devant and grampajpg 400w httpsonlinemlmcommunitycomwp contentuploads201508devant and grampa 225x300jpg 225w sizes=max width 400px 100vw 400px ><noscript> My dad with my son They went fishing

Final Thoughts

In conclusion, these are seven lessons my dad taught me about entrepreneurship. I’m proud to say that I love, respect, and admire my dad. He is one of my life and business mentors and one of my best friends.

He taught me so much about entrepreneurship and life, just by his personal example. I consider myself very lucky to have Harold Holmes as my father. I hope these seven business lessons will help you as much as they have helped me.

What do you think? Which lesson on this list resonates with you the most? Why? What did you learn about entrepreneurship from your dad? Leave a comment below to let me know what you think. I look forward to hearing from you. Have a great day.

chuck holmes


Chuck Holmes
Network Marketing Professional

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11 thoughts on “7 Lessons My Dad Taught Me About Entrepreneurship”

  1. Lesson no 3 resonates with me the most. We are living in a time where people has lost the patience being a virtue mantra. I am truly grateful with your constant supply of rare wisdom towards building my business.

    Many thanks my friend.


  2. You’re lucky to have an entrepreneur dad that you look up to.

    My favorite lesson is #3. You might get successful much faster than 5-10 years. But in more cases than not, building a business takes time.

    Establish both long term and short term goals, and layout the steps you need take to reach your goals.

    There’s no such thing as overnight success. And understanding that will save you a lot of disappointment and frustration in the long-run.

  3. Excellent lessons. Parents are always sharing nuggets of wisdom that we can apply in business and life. My dad too shared so many things with me as a child that I never imagined I would be able to reference now as an adult in the business world, but in fact I have benefited so much from those lessons. Many of the same lessons your dad passed on I also learned from both of my parents. It is a blessing to have people in our lives who want us to learn from their mistakes and grow into better people.

  4. My Father was also a strong mentor for me. He is retired from the Air Force, and also had his own CPA business. He taught me a lot about saving money and being wise in investing. I see your Dad also taught you a lot on these subjects.

    My Dad is now retired and lives in Arizona where he golfs often. I talk with him over the phone on a regular basis and he is still a great mentor to me. When it comes to tax questions, the first person I ask is my Dad.

    Our parents can teach us many things about business and life. I know mine have. Thanks for sharing about your Father Chuck.

  5. Thank You for writing this post. Your father’s teachings reminds me of my entrepreneur father as well and I always remember being a young girl listening to his lessons. And like you, I grew up not wanting to get involved in business, but 23 years later, I’m in the process of starting my own. This post is gold!

  6. This is a beautiful love letter to your father and a note of inspiration to anyone who wonders what drives entrepreneurs to push boundaries, the rules of logic and anything else that stands in the way of reaching goals.

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