88 Tips & Rules for being an AWESOME Entrepreneur


photo credit: Skley

Welcome to Russ-O-Matic’s Rules of Entrepreneurship Engagement!

If you pop the word “entrepreneur” into Google, you’ll be bombarded with clichés like “Think Big!” or “Be Your Own Boss!”. Truth is, being an entrepreneur requires a lot of hard work, time and effort. Starting your own company will be one of the biggest challenges you’ll ever face in your life, but if all goes well, it’ll have one of the biggest pay-offs too.

If you’re thinking about venturing out on your own and making the world a better place, then check out these 88 rules for being an AWESOME entrepreneur.

Entrepreneur: Tips & Rules for Success

1.) Don’t expect it to always be fun. There’s a really good chance you’ll doubt yourself and maybe even hate yourself along the way. You’ll wonder why you ever got the hair brained idea to start a company in the first place and you may even start looking at the people around you as your enemies rather than your friends – after all, they let you go through with this madness. Didn’t they? See that? People have the tendency to throw blame around when things get tough. When the time comes (and that’s a “when” not an “if”) don’t let yourself fall into this line of thinking. Fortunately, with the bad (or downright ugly) also comes the good and hopefully you’ll have more good days than bad, but be prepared for it to not always be sunshine and rainbows.

2.) Don’t run out and hire people on a whim. There will come a time when you’ll have to hire people in order to expand your business, and that’s a good thing. However, resist hiring people unless absolutely necessary, at least at first. Along with your rent, staff salaries can be one of your most significant fixed costs – stop and think about this. Fixed costs. Remember, the more people you have depending on you, the more accountable you need to be. Eventually when you do hire people, make sure you treat them right. Not spreading your own resources too thinly will help ensure each employee you do hire gets the most benefit out of their role in your firm.

3.) Get some customers. This probably should have been the first rule. Getting a customer before you ever have a business is a bonus, since it’ll tell you if there’s true demand for your product. If you don’t have customers, you don’t have a business. Never forget that.

4.) Whether you’re selling a physical item or a service, consider calling it a product. People don’t buy things they can’t see, touch, feel or smell. Sometimes, calling something a “service” can make it seem less valuable than calling it a product. There’s a little company called Oracle that is a great example of how this works. They claimed they had a physical product – a database – and that if you purchased said database, you’d get people to come install it at your location. Obviously, there was no actual product. They were a glorified consulting company in the beginning, but because they marketed themselves as providing a product, rather than a service, people put more value in the company and bought in more often.

You’re on the road to success.


5.) Never fear failure. It’s perfectly acceptable to fail, start over and re-build. Businesses fail and change all the time. Each failure brings with it a learning experience. Reflect on it and use it to better your next endeavour. In order to start thinking like a successful entrepreneur, you’ve got to stop fearing failure.

6.) Try make a profit from the beginning. This seems like it should be every businesses goal, but a surprising number of entrepreneurs seem to forget this. Do your best to raise money whenever an opportunity presents itself. Getting money will be one of the hardest things you do in the beginning and it’s much easier to attract investors to a business that’s floating rather than one that’s so far underwater that they can’t even see the surface.

7.) Keep your ideas simple for the point of raising money. Compare it to selling a car. Although you need to have detailed information ready to present when requested, at first instance – you don’t go into the history of the vehicle or the specifics about how the engine works – you point out the simple and fun aspects of the car and the driving experience. It drives, it’s blue, it has heated seats and a leather interior. Information like “there were 2 previous owners” and that “the sale has had one run through the auction block” only comes in later once you have piqued interest. Simplicity is key.

8.) Don’t be afraid of a little competition. Competition forces you to improve. It’s a motivating factor and can turn a small business into a well-known name and industry power player. Don’t ever be afraid to compete and prove that your product is the best.

9.) Delay using a PR firm. It’s well known that PR builds brands. Don’t get me wrong, I believe wholeheartedly in the power of marketing and branding. But I’m also a strong proponent for running a lean business – especially in the early stages. To begin with, you are the best PR for your company. Get out there and build a buzz yourself. If you have a quality product and treat people right, your company will speak for itself. It should also be said that not all PR firms are the same so when you’re ready to use one, be sure to do your homework.

10.) Hone your communication skills. It doesn’t matter if you’re talking to an employee, a customer or an investor, you’ll need to get your point across in a tactful, but clear way. Hone your communication skills all the time and never stop improving.

11.) Put the customer first. This is very important. Your customer service can’t stop when the purchase is complete. Keeping the communication lines open will help ensure repeat business and it will also help the customer to recommend you to their friends and family, which means more business for you. Win-win!

12.) Don’t forget that your customers & prospects are human – they aren’t competition. Instead of trying to batter them into the ground and getting them to cave into purchasing whatever you’re selling, try to find out what they need, what they want, what they desire and then fulfill that. You want them to leave happy.

13.) Remember the details. This is something to keep in mind with both customers and employees. Remember life details like spouses, kids, jobs, etc. Connect with people on a personal level to ensure they’re happy.

14.) Micromanage your business without being stifling. There’s nobody that knows your product better than you, but if you’re not a software developer (for example), it’s probably best to leave the heavy lifting to the professionals. Instead of telling them how to do their jobs, keep an eye on the development and carefully direct the project the way of your vision. The more oversight a group has, the better. That way, at the end of the development phase, nobody can say they didn’t know what you were looking for.

15.) Hire local when possible. Yes, outsourcing can help bring your operating costs down. But when possible, have pride in your area and make sure your community benefits from your business. Not only is this a good thing to do but your customers will have more respect for you because of it.

16.) Get plenty of sleep. To be a great boss and entrepreneur, you need to sleep a reasonable amount. That’ll help keep your temper at bay (if you are quick to anger) and your mind sharp.

17.) Exercise. Don’t forget to take care of yourself while you create your business. Getting to the top is pretty useless if you’re too unhealthy to enjoy it. Give yourself the maximum time to revel in your success by keeping in shape.

18.) Sell when you’re sick of it. There’s nothing worse than a boss that hates being at work. If the day comes where you dread what you’re doing or when you’re sick of the business, it’s time to sell. Remember that selling takes a year or so of planning, so prepare the ship to dock in port as soon as you decide the ride is getting too rough.

19.) Keep your mind healthy. Don’t make problems for yourself if you don’t need to. You want to stay emotionally healthy as well as physically healthy. Hire smart people that you trust, that way they are capable of dealing with some of the problems that arise.


20.) Pray. It doesn’t matter if you believe in God, Allah, Buddah, Fate or nothing at all. Just take a few minutes out of your day to reflect and be thankful for your success. It keeps you humble, it reminds you of what you have and it prevents you from losing your grounding. Thankful, humble entrepreneurs are the kind everyone likes and wants to be.

21.) Don’t forget to pamper your employees. Your employees are the ones keeping your business afloat when you’re not there. Get them gifts to show them you appreciate them. Massages, tickets, coffee cards. Whatever you can think of, can afford and know they’d enjoy.

22.) Act like the parent and like the company and employees are your children. Give boundaries, don’t be afraid to say no, but give them space to grow and prove themselves.

Go on…strive for success baby!

23.) Don’t be greedy. You may think your product is the best thing since sliced bread, but if you overprice it, nobody will buy it. Likewise, if you pay your employees less to pad the profit margins, you’ll only hire minimum-wage talent. Pay well, price your product accordingly and you’ll be making more money than you know what to do with.

24.) Be your brand. Branding is absolutely everything. Get your name out there and plug your product as much as possible. Word of mouth advertising is great, but get on TV if you can, have a story in the paper, whatever it takes.

25.) Don’t kill yourself building your business. It’s not worth it. Your children, your spouse and your employees are all relying on you. You need to think big, but not at the expense of your personal relationships. Having a life outside of the business will keep you happy, humble and well-rounded.

26.) Have a pathway to advancement. It’s awful to work for a company and know that you’re stuck in your current position with nowhere to go. Even if your employees can’t advance in title, make sure they advance in salary. Have a regularly scheduled review and give raises, even if they’re small. Little bits of encouragement on a regular basis increase the likelihood of your employees actually wanting to work for you.

27.) Let the bad eggs go. If you have an employee that constantly complains about wages despite regular raises, bad mouths the company or bad mouths you, it’s time to fire them. You need to surround yourself with people that will help your company, not hinder it. Being an awesome entrepreneur involves knowing which employees to keep and which ones to cut loose.

28.) Get cosy with your landlord. Assuming you don’t own the building your business is housed in, you’ll need the blessing of your landlord if you ever choose to sell said business (in some areas), to get building and maintenance related issues sorted in a timely manner & for smooth rent review discussions. Getting off on the right foot today can prevent problems in the future and make it easier for you to rent a second or larger space with them if needed.

29.) Avoid moving offices if not absolutely necessary. Unless employees are over-sharing desks, falling over each other, there’s no need to move to bigger digs. Keep the relationship with the landlord and the stability of being in one location for a long time.

business-success-tips-entrepreneur-tips- party

30.) Throw holiday parties, but don’t use company money for it. Consider the annual Christmas party your gift to your employees. Invite customers, employees, their family and associates, then live it up. As a bonus, it’ll build morale.

31.) Get personal. You want to be the type of entrepreneur that employees can come to when they’re in trouble. If someone comes crying to you, take them out into the fresh air and just be with them while they unload. Listen to the problem and do your best to fix it.

32.) Donate money to charity. Be one of the big guys that cares. It won’t go unnoticed.

33.) Return calls. Just returning a phone call when you say you will can score you big points with customers, vendors and distributors.

34.) Ask for advice. It’s okay to not always have the answers. Ask your customers how you can improve your product and ask your employees how you can improve your business.

35.) Hire your customers. If a customer loves your company and loves your product, odds are they’ll be a passionate employee and a great asset.

36.) Add surprises to your orders. If you’re sending out a demo or filling a customer order, add a little something extra. Maybe a note, or a small bonus that the customer didn’t pay for. These small acts of goodwill will really impress.

37.) Keep up with the news. Knowing what’s going on in the world and what is concerning your customers will help you make smart business decisions while offering products that are relevant. Look around you, be aware of what others need and work to address those needs.

38.) Don’t over-indulge. Once you make it big, you’ll realize that the world of entrepreneurs is like one giant party. Resist the urge to meet up and socialize too often and work while others are out playing. Eventually you’ll wind up higher up the ladder while they’ll still be hungover, wondering what happened.

39.) Don’t listen to the nay sayers. Watch out for the gloom and doom type that are out to prove the whole world is ending. They want you to be scared so they can come in and scoop up all the money while you’re not looking.

40.) Use your free time to think of new ideas for your business. Look for inspiration in all situations. You never know when a great idea will hit you in the head.

41.) Depressions, recessions and other negative economic situations just don’t matter. No matter how bad it gets, there’s always money in the market and if you have a must-have product or service, there will always be buyers. Strive to have the product or service people can’t live without.

42.) Bring someone with you to meetings. If you’re busy and have a hard time following up, this is especially important. Let the person you bring with you do the follow-up. Call yourself a mentor if you want to.

43.) Let your customers do your advertising for you. Find sponsorship opportunities that bring in more customers.

44.) Make it easy for people to sign up to communications. Have as few steps as possible to sign up for newsletters, email promotions, etc. Make your sign-up widget mobile friendly since a lot of consumers are now accessing the internet from their smartphones.

45.) Contrary to popular belief, put as much of the information about your company on the front page of your website as you can. People on smart phones hate clicking around to multiple pages for the information they’re seeking because it takes more data and slow-loading pages can be troublesome to navigate.

46.) Say yes to any opportunity that advances your company. If there’s an opportunity to meet with a big player in your industry, but it will cost you money, say yes anyway.

47.) Pursue your ideas, even if they initially appear worthless. You’ll never know which ideas are great and which have the potential to be great unless you pursue them. The really bad ideas will fizzle out early on anyway (when you do your initial research into the project), so don’t worry about chasing a bad plan – within reason of course! 🙂

48.) Keep a blog. The easiest way to connect with customers on a personal level is through a blog. Tell your personal stories and let people get to know you. Become a voice and a leader for your industry. If people turn to you and your blog for information, they’ll probably go to your site for the products they need.

49.) Realize that you can’t save the world. Know what your limitations are and do what you can, but don’t stress over things you can’t change. If you have a product that sounds like it can solve all the world’s problems, you’re probably not being truthful about its capabilities. Don’t try to make your product into some kind of magical cure-all or you risk hurting your reputation.

50.) Frame your first dollar. It will keep you humble and remind you of where you came from.

51.) Tread “re-sale” waters carefully. Be very careful if you choose to get into a business that resells the services of another firm under your own brand. Be sure to vet the service provider well and make sure that they are really good at what they do. At the end of the day to the customer, it’s YOU that’s providing the service and if there’s a huge mistake somewhere – it’s your reputation that’s on the line.

52.) Be careful when considering doing business with clients referred by your lawyer or accountant. Generally this isn’t that big of an issue but in some cases it’s another idea that has the potential to cause problems if thing were to go sour (you both share the same agents) and can usually end up being just a colossal waste of time…time that you don’t have. Again, exercise caution.

53.) Celebrate your success. Your employees need it, you need it, so why not go for it. Bring in a masseuse, have lunch catered and take a few minutes on Friday afternoon to reflect on everything that went right.

54.) Sell your first company. It’s too easy to become emotionally attached to your first company and unless your name is Mark Zuckerberg, or you’re absolutely still enjoying the ride it’s probably time to sell. Put the notch in your belt and the money in the bank so you can invest in your next enterprise.

55.) Pay your employees first. Pay for your business expenses, then your employees and then finally yourself. That way, you’re motivated to make sure there’s something leftover.

56.) Don’t get too hung up about your ideas. Ideas on their own are useless. It’s okay to bounce your thoughts around with someone else. You can guarantee you’re not the first person to ever thing of something worthwhile, but what you want to do is be the first to offer that great idea in product format at a great price. Being open about your ideas won’t make you weak, it’ll actually give you a huge advantage as you bounce ideas off other people.

57.) Be yourself. If you’re honest with yourself and are acting naturally, it’ll be easy to tell if you’re doing something you love or doing something to make money. You’ll be a much better entrepreneur if you love your work and have a passion for your business.

58.) Don’t be all about the money. If you want to be rich, that’s fine and that’s a great goal, but if you want to have a successful business and be a great boss, you may need to separate your drive to succeed from your goal of being rich. Don’t look at a product in terms of what you can sell it for, but in terms of how much other people will like it. If you have a solid product that you love and that many other people love, financial success will soon follow on its own.

Strive for both personal & business success.


59.) Work hard to achieve your goals. Your job shouldn’t be all-consuming, but you’ll need to bust your butt to get ahead, especially in the beginning. Having an idea is half the battle. The other half is having the commitment to successfully infiltrate the market.

60.) Hire people that are smarter than you. This won’t do a thing for your ego, but hiring a great team of people that are smarter than you will give your businesses every advantage. Once you have that team in place, turn the reins over and let your management team prove themselves. They’ll feel great having the extra responsibility and you’ll feel great knowing that your baby is in good hands.

61.) Find someone you can trust as a personal advisor. Everyone needs someone they can trust that they can just bounce ideas off of. Once you find that person, consider working with them as your personal advisor. You’ll save money foregoing the bad ideas and with any luck, your sounding board will help you make improvements to your best ideas that can make you even more money.

62.) Don’t stop learning. You’re never going to have all the answers. Ever. Don’t pretend that just because you’ve reached a certain level of success that you suddenly know all there is to know about running a business. Learning doesn’t have to take place in the classroom, so it’s important to be open to learning new things no matter where you are. Check out some online courses that you can take at your own pace.

63.) Create the right work environment. Nobody can work well in a workplace that’s dirty, cramped or poorly lit. Create a happy, fun place to work and you’ll suddenly see that everyone likes heading to the office a lot more. The best entrepreneurs are those that give their employees the same work conditions they themselves enjoy. Comfortable chairs, desk space and happy, productive colours are all things to consider.

64.) Dress for success. If you’re meeting with a client or vendor, dress for the part. Wear a suit and don’t forge to add a power tie. At the office, more comfortable clothes can be fine as long as you let your employees enjoy the same privileges. Whether you’re dressed up or not, don’t be sloppy. Regardless of how casual your clothing is, you still want to look like the boss.

65.) Avoid distractions. There are lots of distractions that can take you away from your business and goals. Relationships that aren’t going anywhere, quick money schemes and regular parties (unless partying is your business :)) are all distractions. Ignore them and focus on creating your business.

66.) Maintain your tools. You need your computer to do your work. Take care of it so you never lose your source of income. Likewise, your phone is probably an important asset too. Put a little money into getting a good model and then make sure you take care of it properly so it will last for years.

67.) Never stop networking. There are endless ways to make contacts in your field. Connecting with other professionals is called networking. Sign up for LinkedIn, Facebook or any other social site you can find and make sure your profile is easy to follow. Connect with employees, causal contacts and anyone else you can think of. You’ll have the opportunity to make introductions to your friends’ friends if you play your cards right.

68.) Be warm. Remember that cold fish you worked for in high school to earn spending money for movies and the school ball? Don’t be like that. Take every trait you can think of that your least favourite boss had and reverse it. Be like that.

69.) Turn your phone off at the end of the day. You can’t be awesome 24/7. Even the best entrepreneurs need time to just be themselves on their own, whether that’s playing the part of the bachelor or the devoted father. Do yourself a favour and forget about business for at least a couple hours a day. You’ll go back to work refreshed and ready to keep tackling problems.

70.) Write down your goals. Writing your goals out makes them more solid. It reinforces them in your own mind and gives you something physical to revert back to. People that write their goals down are more likely to achieve them. Don’t just write business-related goals, but also leadership goals you wish to reach, like retaining employees longer, offering better benefits or making it into a list of top companies to work for.

71.) Have a growth mindset. A lot of people wind up giving up on their dreams because they have a false belief about themselves. They may tie success to a specific item, causing them to have a fixed mindset. Successful entrepreneurs feel that success is linked to hard work, learning and training. Their mindset is backed by growth. Strive to be this way.

72.) Have faith, not just in a higher power, but in yourself. Don’t lose faith in your own abilities even if you have a few failures. You need to build and maintain your confidence in order to stay on top. If you believe you can achieve anything, you’ll be a lot more likely to do it.

73.) Be open to constructive criticism. Many times, people are afraid to give feedback to entrepreneurs because they don’t want to paint themselves as a target for revenge. Make sure you’re open and accepting when it comes to feedback so that anyone, from an employee to a customer, can honestly tell you what is and is not working for them. You can use that honest feedback to hone your system and create a better business. If you’re open to feedback, but you’re not getting any – go and seek it out. The faster you hear what isn’t working, the fast you can fix it and grow your business.

74.) Don’t let yourself give up. Don’t give yourself the option of giving up. Don’t have a plan B or an evacuation procedure in place in a sense (I don’t mean you shouldn’t have contingency plans for your business operations-wise). Make yourself stick it out and make yourself make the business work – even if you don’t get it right the first time.

75.) Be careful about who you are friends with. You’ve probably had a variety of friendship types in the past. From users to true friends, to people who tend to leak their belief systems onto those around them. Because of that, it’s better to surround yourself with others that are like you – tenacious, smart, driven and daring. Eliminate anyone in your life that is weighing you down. Harsh – but necessary.

76.) Control your emotions. It’s easy to get emotionally involved in your business, but the key to success is not letting your emotions control you. Whether you’re terrified of failing or beyond angry at a vendor that let you down, you need to put a lid on your emotions when you’re on the clock. Find other ways to get a release, such as working out or meditating.

77.) Stay inspired. It can be a lonely road for an entrepreneur. Sometimes giving up and joining the worker bees again seems like a great idea. Don’t do that. Stay inspired by reading books or articles about other people that have been in your shoes. You can even network and have lunch with like-minded individuals.

78.) Don’t waste time living in the past. Any mistakes you made in the past, whether it was hiring the wrong person or trying to grow too quickly, no longer matter. Give up on past mistakes and only look to the future. Remember that every day brings a new opportunity and every time you walk through the door, you’re starting fresh. It’s never too late to wipe the slate clean and start over, so if you’re not the type of entrepreneur you want to be, it’s never too late to change that.

79.) Always have discipline. One of the toughest part about being an entrepreneur is that you don’t have a boss. You are the boss. All of the decisions come down to you. There’s never anyone to give you direction when you just don’t want to try any more. If you need to take a break from being the boss, hopefully you’ve hired smart, trustworthy people that can steer the ship in your absence.

80.) Use the term “we” more than the term “I” and mean it. You can’t build a business on your own. Even if you don’t have a single employee, you’ve relied on other people to reach success. Whether it’s your customers, your banker that gave you a loan or a friend that pushed you to start your business, you didn’t get where you are on your own. Remember that.

81.) Release new products regularly. You know the feeling you get when your favourite brand releases a new product that you’ve just got to have? Give your customers that feeling. Keep them anticipating more and their excitement will rub off on you.

Entrepreneurship: Keep building on your recipe for success.


82.) Always look for new sources of funding. Even if your business is off the ground and making money, never stop looking for sources of funding. The more funding you have, the less stressed you’ll be and the happier you’ll be. Happy entrepreneurs make the best bosses.

83.) Look for novel ways to deliver your product. You may not have access to a fleet of drones that can drop your product to people’s doorsteps (hint hint…Amazon), but maybe you can outsource to someone who does. Having trademark packaging or including a personal note are just some of the ways you can add a touch of novelty to your product delivery.

84.) Have a Facebook page and update it yourself. There’s nothing less awesome than an entrepreneur with a personal Facebook page maintained by an employee. Make your own updates. Genuine updates – they will be better received by the public.

85.) Pack in experiences as often as possible. You can get a lot of inspiration from a single experience. Whether it’s traveling, hitting up a local winery or just playing tourist in your own city, mingling with other everyday people is a great way to figure out what the market wants and what it needs.

86.) Don’t be a player. Yes, I said it. You’d be surprised how many companies have struggled with image issues because of their CEO’s midnight indiscretions. One even got fired by the board from a company HE FOUNDED! Success makes people do stupid things. Don’t have a string of meaningless relationships that will get your face plastered in the tabloids. Instead, focus on meaningful relationships. You can beat the odds and your fidelity will make the public and your employees respect you even more.

87.) Let your employees be creative. Everyone in your company is valuable and can have great ideas. If you constantly brush off the mailboy’s suggestions because he’s “just a mailboy”, you may be missing out on a great mind. Be open and value all of your employees equally.

88.) Be willing to grow. You can’t change overnight, but be willing to accept change as a part of life and embrace changes that will make you a better person. If you suddenly find yourself not liking the type of person or boss that you are, change. It’s that simple.


Use these 88 tips to be the type of entrepreneur people idolise. This collection of tips will help you lead a successful personal life while your business thrives and your employees rejoice. Soon, you’ll be universally loved and on the road to true success. Don’t forget us little people when you get there! 🙂

32 Responses

    • Russ-O-Matic

      Thanks Judia, I do enjoy sharing what I can with the world. 🙂


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