5 Entrepreneurial Lessons I Learned Since My Last Birthday

As I write this on my 31st birthday, I thought it may be helpful to take a look back at this year in my life as well as in business. I probably learned more about business in the past 365 days than I have thus far in my life.

Overall, my business did grow (prorating fiscal year) and I brought on some great clients, but most importantly I did a lot of work on myself as a CEO.  Therefore, instead of discussing my successes, I thought I would tell a few stories and subsequent entrepreneurial lessons that I did not know 365 days ago and those few events that forced me to learn these business / life lessons.

As you’re reading this, it is important to realize that old habits die hard, but to get to the next level, you have make sure that you kill them. With that being said, please enjoy my essay recounting the last 52 weeks of my entrepreneurs journey.

1. Come To Terms With Your Shortcomings. Ignoring Them Can Lead To Dangerous Places.

I hate numbers and used to consider them a shortcoming not because I couldn’t learn them, but because I was almost afraid that if the business would dip even 1%, that meant doomsday.

The thinking is very irrational, but I always figured that if I did what I needed to do (marketing, recruiting, media stuff, internal recruitment, etc.), the numbers would just go away. Ignore and everything is good.

This boneheaded tactic almost hurt me and could have damaged a great company that I gave everything I had to build what it is today. As terrible as it may seem, to be successful in business you must face your weaknesses and figure out how to make them work in your favor.

It’s not all that bad once you start working on them. After all, you’re the CEO of your own company – you must grow yourself in order to grow others.

2. Make Decisions Based On Logic, Not Based On Emotion

A very bad habit I had when I was younger was that I would make impulsive decisions based on a particular emotion I was feeling that day or sometimes even in the moment. It was never quite a problem until my business got bigger and I became responsible for others.

I don’t think that it is intelligence that makes the great CEOs from the average, rather it’s their ability to use their intelligence to make decisions even during times of stress that prove to be emotionally taxing.

What soothes in the short term can become a pain in the long term.

3. Don’t Think In Black And White Terms

There is a commercial running in the U.S. for an online print shop, which among other things prints basic business cards. In the commercial, one of the actors refers to the time when he first showed printed business cards he purchased to his sister only for her to say that he now has a real company.

In business, there is no line that you must cross for your business to be real. When you land your first deal, nobody comes to your door to congratulate you and they sure as hell don’t either when your business becomes worth ten million.

Real is what you make it. Don’t think in terms of all or nothing. It is very self-defeating.

4. Don’t Overspend. No Stock Goes Up Forever, No Business Increases Forever.

Many people associate entrepreneurs with lavish spending. When you become successful and things are readily available to you, don’t over indulge thinking that you are invincible in business.

My best season in little league was when I was 13 years old. I remember two things from that season: my batting average and my friend A.J.’s father. 

A.J.’s father was the nicest guy you would ever meet. A self educated man, he owned a construction business and when it did well, he would buy boats, awesome interior decor… and most impressive to us was the deep fryer they had in their kitchen (very high class for Toms River, NJ).

About two years after that season, my friend’s house was empty. We would sit on the floor to watch the gigantic TV screen too young to comprehend how miserable it must have been for A.J. (my friend) and his dad. He would eventually build back up his business years and years later, but digest this story do your best to prevent it from happening to you.

Even more unfortunate, A.J.’s father made another grave mistake. Not good with numbers and not wanting to face it, A.J.’s dad kept a lot of cash lying around the house while logic would say put it in a safe place. His house was robbed and he lost a fortune.

The story ends there. There is not a positive takeaway except that maybe all these lessons are somehow intertwined?

5. Learn How To Delegate And Think Like An Employee

The hardest part of management for entrepreneurs is that they don’t think like employees and assume that employees think like entrepreneurs. Many psychologists refer to this as “projecting.” Don’t get me wrong, if this were only the case, my life would be a lot easier.

To successfully manage an employee, you must delegate a set amount of work for them everyday or else they will take what you would describe as your life’s work and perceive it to be wishy-washy. While that doesn’t sound right, it’s the truth.

Treat your employees with respect, not as friends and always give them guidance and knowledge, but not without that signed non-disclosure.

In Closing

Years 30 to 31 were cramming years for me. I pretty much laid it out and really hoped that somehow it connected.

Now, I must warn you that anyone can read this article, but the man or woman who can execute on 1 or 2 will be further along in their journey as an entrepreneur. None of us are perfect and none of us will ever be, but I have a feeling that the ones who come closest lead the happiest, most lucrative lives.


Photo courtesy of Tama Leaver

About Ken Sundheim

At age 25, Ken Sundheim started KAS Placement Recruitment and Staffing from a studio apartment in New York. With no industry experience nor contacts, Ken learned the staffing business out of a book. KAS Placement now has two offices and is currently nominated as America's Most Promising Companies in 2012 by Forbes Magazine. Ken has previously contributed to NYTimes.com, WSJ.com, USAToday.com, Forbes and many more. You can read more at kensundheim.com.

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  • Hi Ken, I’m curious as a result of point number one with the numbers, what are you doing differently now? Are you working with your accountant and watching the numbers more closely on a regular basis and making decisions based on what you learn?

    • Ken Sundheim

      Hi Yaro,

      I’m sorry for the delayed response, I was on vacation. I have hired an accountant now and am making decisions based on numbers rather than creativity if that makes sense.

  • nice article Ken.

    points 1 and 5 resonated really well with me.

    regarding point 1, the sooner one realizes this the better. many people try to improvise on their weaknesses. one approach I have taken is to let the weaknesses be just those, and instead get better at what my strengths are. there are too many resources one can rely on to fill in the gaps – and one can never (IMO) overcome all weaknesses to the point where the time investment pays off.

    regarding delegation, my businesses, whether offline or online, have grown leaps and bounds since I started delegating. for example, hiring a manager and paying them a healthy salary has done wonders for my brick and mortar business. hiring virtual assistants have taken my online businesses to a whole new level. same goes with hiring rental property managers.

    delegation is key to success at every level, and a fortune 100 CEO will say the same.

  • Hi Ken – Thanks for sharing this, I really enjoyed it. Points 2 and 3 definitely saw myself relating to.

  • Surminga

    Can really relate to your second point, but this is a new thing to me, not sure I’ve looked back over and assessed myself but only looked back over my business

  • To be successful in business you must face your weaknesses and figure out how to make them work in your favor. It was as if you were referring to me here. That is the worst thing that always happen to entrepreneurs, they allow their fear to overpower them instead of using it to there advantage. Thanks Ken for sharing such and awesome post.

    • Ken Sundheim

      There is a saying that denial becomes an addiction. Thanks for reading!

  • If one can overcome their shortcomings, they will very likely be successful in my opinion. Everyone has some type of talent, and when you remove the obstacles to that talent, you’ve freed yourself to be successful.

  • Great tips! Your readers might enjoy learning more about the role business location plays in startup success. They can find several free white papers here – http://enterpriseappalachia.com/

  • Overspending is something entrepreneurs have difficulty avoiding, especially when their businesses are yielding so much profit at the moment. They still need to save some money for rainy days. The market doesn’t stay the same, so they need to be on their toes financially.

  • you are so right, especially lesson number 4 , i can relate to it very well
    thanks for sharing those valuable lessons with us.keep up the amazing work

  • Hey Ken,

    I think a lot of these lessons seem to relate to your own limiting beliefs which you’ve changed in order to get out of your own way – e.g. with the delegation one the limiting belief might have been ‘It’s not worth delegating’, ‘I can’t afford the time/money to delegate this’ or ‘Nobody can do this as well as I can’ – whereas if you never do it, you’ll never know and it’s something you need to do in order to grow, create space and make your business processes better and more scalable.

    The other massive point I think successful entrepreneurs ‘get’ is the idea of failure – i.e. they just have no concept of it at all – it’s ok to fail, but failing doesn’t make you a failure. Anyone successful with anything worth shouting about has got there through failing first before they succeeded.

    It’s a really interesting article – but surely you learned more than 5 things? I reckon I probably learned about 365 things in my first year as an entrepreneur 😉

    • Ken Sundheim

      Hi Alan,

      I have learned a lot, yes. Maybe too much. Thanks for reading.

  • Hi Ken,

    thanks for these pointers. I am just starting out and can see the potential in myself and my character traits to fall into more than one of these pitfalls. Forewarned is forearmed as they say.


  • JC

    3 & 4 speak most to me. I think being able to realistically balance your budget is the hardest thing to do as an entrepreneur (and seems/feels impossible for startups most of the time).

  • Great post. I think 1 is an especially important point – denial is never a good place to be in!

  • Allain Flores

    it’d be of help to me as a future social entrepreneur. lot of thanks, Sir Ken. 🙂

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