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2 Biggest Lessons Learned As a Business Owner

By: SmallBizClub


businessman hand holding light bulb with finance document and tool,concept of New ideas for business and fonance.

Starting a business means learning a lot of things on the fly. You might have a business degree or have years of experience working for others, but there are countless things you’ll have to learn for yourself, or learn from others.  SmallBizClub recently asked three of our Advisory Board members about their biggest lessons learned as a business owner while they grew their companies.

Ted Jenkin, CFP®

There are two big lessons I learned having owned more than 10 businesses in my career.  When it comes to your projections to get the business off the ground, measure twice and cut once.  No matter what you put down on an excel spreadsheet, it is going to take you one year longer to become profitable than you project on your initial assumptions as real-life hits both on the revenue and expense side when you start running the business.  The second is to get it in writing.  While a handshake deal or a ‘we will take care of it’ sounds good, what counts in business is what is in writing including rent agreements, vendor agreements, employee agreements, and sales agreements,  it’s important to get yourself a very good attorney and do not cheap out on that cost.  Or, it will cost you in the long run.

Ted Jenkin is a certified financial planner and the founder of oXYGen Financial, a leader in financial services for the X & Y generations. Ted is Editor-In-Chief of the top ranked personal finance blog, Your Smart Money Moves and host of the #1 entrepreneur podcast, The Shrimp Tank.

Ben Norton, CEO VelocityX

I’ve had the good fortune to own three businesses and be a partner in two more. I’ve learned countless lessons through my entrepreneurial journey. Some were through accomplishing objectives, though that vast majority were from coming up short.

I Would Have Been Done Sooner But I Had Help

Definitely one of the biggest lessons I’ve learned during my career has been that I can’t do everything myself and I’m definitely not the best and the smartest when it comes to all facets of business. When I finally accepted this and embraced the fact that the key to success in business is surrounding yourself with great people, giving them the resources they need and getting out of their way so they can achieve great things. There’s an old proverb that really brings this home; “if you want to go fast, go alone. If you want to go far, go together.”

To Achieve a Great Vision You Have to Have Great People

Above view of friendly business team working together at meeting

Another of the biggest lessons I’ve learned in business is that you cannot achieve a great vision without great people. What it means to be a great fit in an organization is unique to each business. As a leader, you need to define what it means to be a great member of the team and then make sure everyone of your employees fits your definition. There are two components to this; Right People and Right Seat.

Right People means someone aligns with your core values and are a great fit with your culture. Right Seat means they have the skills, knowledge, experience and desire to excel in their role. Right People, Right Seat…you have to have both.

Ben Norton is CEO of VelocityX, dedicated to helping other entrepreneurs run their businesses on EOS (The Entrepreneurial Operating System®).

Bill Yates, Executive VP, Velociteach

I posed the “lessons learned” question to a number of friends who have launched a business or run a small business today. Their responses are a treasure-trove of advice. We can lump them into 3 categories:


You’ve got to know the numbers. Having a solid understanding of the financial aspects of your business is foundational. Check out this advice from seasoned entrepreneurs:

  • “If your background is not finance, take a basic accounting class.  It is so important to know your numbers.”
  • “Understanding the cash flow requirements and patterns of your chosen business and how to operate within that framework.”
  • “Make damn sure you have enough capital to last twice as long as you forecasted. Then double it again!”
  • “Cash flow. That is all…”


Finances are vital. Equally important is building a healthy team. If you want to grow and scale your small business, you need to create a high-performing team and lead well. See what others shared with me:

  • “Surround yourself with people that are smarter than you AND willing to tell you how to do it better.”
  • “Never come to me with a problem without (bringing) a possible solution. Even if it is the wrong solution, we’ve got to start somewhere.”
  • “Get the right people in the right place.”
  • “Firing is like a Band-Aid. Hire slow. Fire quickly.”
  • “Never undermine the authority of a manager under you in front of staff.”


Money and people are important for small business owners, and so is having the right mindset. A key to staying in business… and eventually thriving is maintaining a positive attitude and welcoming the chance to learn. Leaders of small business need to have resiliency and open-eyed optimism woven into their DNA. Consider these perspectives from other small business leaders:

  • “For me, there were a lot of tough times early on, and people look to you to be optimistic. It only takes one good event or year to turn things around and flourish, so… remain positive and optimistic.”
  • “Don’t be afraid to ask for help.”
  • “I learn something new every day.”
  • “Keep asking questions – you’re never too old to learn, and you’ve never learned enough to know it all.”
  • “Problems are many; the only thing you can control is how you personally react and handle them.”

Bill Yates is the Executive Vice President of Velociteach, dedicated to helping project managers get better.

Published: May 7, 2024

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SmallBizClub.com is dedicated to providing small businesses and entrepreneurs the information and resources they need to start, run, and grow their businesses. The publication was founded by successful entrepreneur and NFL Hall of Fame QB Fran Tarkenton. We bring you the most insightful thinking from industry leaders, veteran business owners, and fellow entrepreneurs. Follow us on Facebook, Twitter, and LinkedIn.

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