CEO Nugget

20 Entrepreneurs Share Their CEO Nugget

If you could hop into a time machine, what would you tell your younger business self? What are the biggest lessons learnt since you started entrepreneurship? This is one of our favorite questions here at CBNation.

Here’s what CEOs would tell their younger business selves.

#1- Not to be overoptimistic and ignore base rates

Photo Credit: Thomas R. Harris

The one big piece of advice I would tell myself is not to be overoptimistic and ignore base rates. I was a typical entrepreneur who knew how often businesses failed or how long they took to get established, and so on, but, like many entrepreneurs, I felt it didn't apply to me – my situation would be different. I would tell myself to look and realize that the base rates are true, and instead of just being optimistic about the future, find those who've succeeded and exceeded the base rates, learn what they did (and didn't do), then apply those to help beat and exceed those rates myself.

Thanks to Thomas R. Harris, The Exceptional Skills!

#2-Time management is the backbone to everything

Photo Credit: Kris Ward

It took 4 years for me to figure this out (but some never do). I looked around and realized…things are NOT slowing down. I was going really hard, doing the grind and it was wearing me out! I always thought working harder would get me over the next hurdle, and then it would slow down. I looked exhausted, beat up . . I was putting on weight. (Not at all how you want to present yourself . . as a business professional!) Then one day, I nearly electrocuted myself simply because I was in such a rush! Something had to change! I started feverishly examining productivity and my successes resulted in my book Win The Hour Win The Day. I’m still amazed how quickly everything turned around once productivity became my super power! I have a clarity and calm that I couldn’t even imagined. I am also more creative and all this while having a FULL life. I execute projects instead of juggling my workload and reacting to emergencies. The very best part is. . . I do all this while working way less hours!

Thanks to Kris Ward, Win the Hour Win the Day!

#3- Be convicted about your idea but not to the point

Photo Credit: Tom Wilde

The best advice I heard about entrepreneurship is that you have to care deeply about your business, but not too much. This paradox really does describe the process of building a business. You need tremendous conviction around your idea to see it through because if it really is disruptive and valuable, most people in the early days will tell you it won't work. You will have to endure this thousand of times over. The challenge though is you need to be both convicted but not to the point where you can't take input from your important constituents, namely your customers, to adjust your approach to the market to make your business successful. Looking back though, I would say that too often I let the feedback I received from outsiders be too dominant an influence on our strategy. There is something incredibly powerful about identifying a pain point in a focused and relatively narrow fashion, and then just single-mindedly crushing that problem over and over again. By doing so, you create a very large competitive barrier. Even if your strategy is wrong, I have found that this leads to better outcomes than constantly changing strategy and chasing what you see in the market. The reality is, by the time something is obviously succeeding, it’s too late to emulate it. You are better off just trying to be your best self as a company.”

Thanks to Tom Wilde, Indico!

#4- Failure is a seed that needs to grow

Photo Credit: Michael Drake

If I could travel back in time, I would tell my younger self that all the times I failed -or felt like a failure- were the seeds I needed to grow. Growth is painful but you can’t change without the pain. Every challenge is an opportunity, and I would counsel myself to embrace these opportunities.

Thanks to Michael Drake, PMG Home Loans!

#5- Structure profit into your business before you start

Photo Credit: Leonard Pickel

When writing your business plan, and you get to the end, if the bottom line doesn't say Obscene Profits, then go back and rework the plan! The business of a business is to make a profit, and the best time to structure profit into your business is before you start. Most of my early business fails were because the profit margins were too small. You get open, but it’s a struggle, to make payroll, to make rent to pay yourself anything, but if you could just do it cheaper, or sell a few more, you could make it! Then something out of your control happens. The rent goes up, or you lose a key employee, or the tax structure changes, or there is construction on your main road, or it rains every weekend for a month, and because you have no profit buffer, track record of profit to show a bank, no savings to fall back on… you are out of business. Increase advertising, increase the value of what you are selling, decrease costs, do whatever it takes to make sure when you open that your business makes a lot of money, whatever “a lot” means to you. Because if you don’t… you will fail.

Thanks to Leonard Pickel,!

#6- Fail fast and be patient

Photo Credit: Paige Arnof-Fenn

Patience – It really is a marathon not a sprint so do not set arbitrary goals like being named 30 under 30 or 40 under 40 because it may take you longer than Mark Zuckerberg to hit your stride and that's ok. Most people take many detours on their career path before finding their true calling. Don't be disappointed if you get to 40 and are still exploring because the journey really is a great adventure so enjoy it!
Fail fast- Don¹t be scared to fail, just learn from every bump in the road so you make better mistakes next time, that is where you learn the most! You learn to do by doing. Course correct and pivot along the way, it makes for a fun career path.

Thanks to Paige Arnof-Fenn, Mavens & Moguls!

#7- Focus on the upside

Photo Credit: Paul Faust

The advice I would give to my younger self is sometimes the advice I still need to give to myself: to focus on the upside. When you are thinking about any situation, interaction, challenge, or opportunity, don't spend time thinking about all of the things that can go wrong. You have to train your brain to look for all of the things that could go right, instead. We're programmed to assess risk at all times and look for potential pitfalls. The what ifs that you should be focusing on are the potential upsides – use those as your metric for making decisions. It's easy to find a problem and use it as an excuse. Fear will only hold you back. Inaction is, by definition, much less effort. In most cases…even if something does go wrong or you outright fail…SO WHAT! We make a bigger deal out of things than other people do. We highlight our failures in our mind in huge neon lights when most outside people hardly notice or remember. There are many times in my life that I've psyched myself out and missed an opportunity. You have to flip the script in your head, stop focusing on what could go wrong, and focus on what could go right.

Thanks to Paul Faust, RingBoost!

#8- Be more tech-savvy

Photo Credit: Lance J. Robinson

Above all else, I’d tell my younger self to be more tech-savvy and take the internet more seriously. That way, I could have established a stronger internet presence earlier on and continue to build it over the years. Nowadays, it’s vital to be computer and internet literate as a business owner. In law, we’re seeing a strong trend towards the paperless, and some attorneys are struggling to keep up. This goes doubly for cybersecurity. There are rules that govern client-lawyer confidentiality, and any perceived breach of that confidentiality or negligence concerning client privacy could land you in hot water.

Thanks to Lance J. Robinson, The Law Office of Lance J. Robinson!

#9- Be positive

Photo Credit: Mark Armstrong

I’d explain that you run into two different kinds of people in this world: can-do’s and naysayers. I’d explain that one of life’s great temptations is to become a naysayer: to join the crowd and fit in. You’ll be welcomed with open arms, too, because misery loves company. And it’s easy: you never have to take risks, and put yourself on the line. You can be “above it all,” and sneer and laugh at the people who are striving, and trying to make a difference. I’d explain that naysaying is a trap, self-sabotage, and that you must avoid naysayers at all costs. I’d tell myself to stay positive and be proactive. When in doubt, act. Don’t cede your life to circumstance.

Thanks to Mark Armstrong, Mark Armstrong Illustration!

#10- Time travel

Photo Credit: Jeremy Rose

Given an opportunity to time travel, and change or do something different than before, I'm sure I'd invest in Bitcoin. It may be a cheesy answer, but knowing how much their value skyrocketed over the last few years I'd invest in some coin, wait to sell them at a high price and buy myself a vacation home in some summer resort, maybe in Hawaii.

Thanks to Jeremy Rose, CertaHosting!

#11- Stop focusing on the money

Photo Credit: John Munn

If I could go back in time and tell my younger business self anything it would be to stop focusing on the money. Focus on providing value to customers and the money will come. Besides, money is not nearly as important as time, freedom, or the satisfaction of helping people. Spend more time with your friends/family and doing good in the world – that will make you infinitely happier than money ever could.

Thanks to John Munn, Global Digital Week!

#12-Don’t shy away from constructive debate

Photo Credit: Peter Maglathlin

It's a lesson I could only learn by starting-up my business. And that would be: Don’t shy away from constructive conflict or debate. It’s important to be transparent, and many times the best ideas are born in the midst of debates and disagreement.

Thanks to Peter Maglathlin, Trade Hounds!

#13- Thank you

Photo Credit: Bethany Babcock

Thank you for going home to study when others partied. Thank you for working full time in college to avoid loans. Thank you for working long hours and volunteering for projects so you could learn new skills. Thank you for staying at that job a little longer than you wanted to learn how to communicate and navigate challenging working environments. Thank you for not doing what everyone told you to do. All the sacrifice was worth it and my thirty-year-old self thanks you.

Thanks to Bethany Babcock, Foresite Commercial Real Estate!

#14- Life is a single-player game

Photo Credit; Tommy Griffith

Right now, you think that everyone is watching you. You think that everyone is judging and evaluating you, sitting on pins and needles, anxiously waiting to see what you do next. If you succeed, you think they'll erupt in thunderous applause, and if you fail, you think they'll be disappointed, murmuring about how you had so much potential, but you blew it. The reality is that no one cares. No one cares about you, your business, or what you do with your life. You think life is a multi-player game, where we are all competing with each other. It's not true. Life is a single-player game. You are only competing with yourself. You can either take this as the most horrifying conclusion possible, or the complete unshackling of your own psyche. No one is watching – so do whatever you want. Empty the gas tank and dance like no one is watching – because I can assure you, no one is.

Thanks to Tommy Griffith, ClickMinded!

#15- Start a business earlier

Photo Credit: Marc Andre

When I was in my 20's I didn't want to start a business because I saw it as being too risky. It wasn't until I had gone through several frustrating years of dealing with corporate America that I finally decided to start my own business. Once I started my own business, my financial life and the level of satisfaction with my career improved drastically. I wish I would have started sooner rather than looking for a job that would satisfy me.

Thanks to Marc Andre, Vital Dollar!

#16- Network heavily OUTSIDE of your trade

Photo Credit: Simone Dominique

In my early years I spent most of my efforts improving my skills and networking within one industry. When that financial industry crashed and thousands of people were laid off, I went through the painful process of learning new technology skills. Now I know that there is tremendous value in stepping outside of my comfort zone, keeping a philosophy of lifelong learning, networking at other industry functions, and finding areas for collaboration.

Thanks to Simone Dominique, Global Center for Climate Resilience!

#17- You are a serious businesswoman

Photo Credit: Hannah Attewell

When I started my business, especially as a young woman working in a creative field, I was often worried people felt my job wasn’t serious, that is was an expensive hobby, something that couldn’t make money, or worse yet, they assumed I was being funded by my parents until I got a “real job” (I was not being funded by anyone). As a result, I diminished my success a lot, I played down my achievements, believed I had just been lucky or it was a fluke. I made myself small. That stopped me from really showing up as a serious business owner, putting myself out there when opportunities arose and also it made me really nervous that I wouldn’t be able to keep replicate my success as my business grew. That was over 8 years ago and my business has grown, I now call myself an entrepreneur and business owner first before explaining what I do and there is so much power in that.

Thanks to Hannah Attewell, Force of Nature Coach!

#18- Have an Endgame

Photo Credit: Rio Rocket

Something I was fortunate enough to learn sooner than later was that you shouldn't only aim to use your working skills to make other people successful by solely focusing on building their business to earn a check. You need a long-term plan, an endgame you might say, in which you can utilize your skills for a much higher level of personal success. Listen, the struggle to avoid burnout is very real. I use to burn out all the time when I was younger because I put so much work into making other people highly successful in order to earn my fee/commission. I would have wanted to tell myself right out the gate that the best way to grow a career is by absorbing as much knowledge as possible from those you are performing the work for. Once you start to become accomplished in your field if you are knowledgeable, experienced, and proficient enough, you will be approached by people with business ventures who have the business idea but need either the creative mind or another skill they are lacking. A skill that you can provide in order to bring a very lucrative idea to fruition. These are your golden opportunities.

Thanks to Rio Rocket 

#19- Learn Sales!

Photo Credit: Jacqueline Basulto

No matter what you do as a business person or as a human in general, being skillful in sales is necessary to achieve success. Whether you're trying to sell a service, market a product, or ask someone to go on a date, learning to sell will help you understand how to be sensitive to other people's thoughts and needs, where opportunity lies in the market, how to best present yourself, and how to help others. The more you help others and present yourself (or a product or service) as a solution to a problem, the better off you'll be in business. Not only that, but learning sales made me a million times more confident in my own voice and speaking up for myself as a young woman.

Thanks to Jacqueline Basulto, SeedX!

#20- Take care of your overall health

Photo Credit: John Crossman

I would tell my younger self to spend much more time educating myself on feelings and mental health. Exercising regularly, eating healthy, journaling, expressing feelings, calling friends, and seeing a counselor. I learned all of these in my 40s and wish I had learned in my 20s

Thanks to John Crossman, Crossman & Company!

What would you tell your younger business self? Tell us in the comments below. Don’t forget to join our #IamCEO Community

Mercy - CBNation

This is a post from a CBNation writer. CBNation is a Business to Business (B2B) Brand focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts ( and videos ( CBNation is proudly powered by Blue 16 Media.

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