84 Lessons From 20 Years As An Online Entrepreneur (Updated)

I’ve been running an online business of one form or another for 20 years now.

I got started in 1998 with the start of a technology blog talking about how computers work and how to build them. Even though I now refer to it as a “blog”, back then it was just a website with articles on it. The word “blog” hadn’t even been invented yet. 🙂 It was a very manual process. I literally wrote my articles in HTML.

It never dawned on me at the time that that stupid little computer website with weird animated buttons (remember the 88×31 Netscape buttons, you old timers? 😉 ) would turn into a business.

But, it did. I turned it into a six-figure business, fielded a $1 million buyout offer within about 3 years, had that deal fall apart, then embarked on building a much more solid online business out of it as we came out of the dot-com crash. Those lessons of the dot-com crash shaped my approach to business online. (Read more about my backstory here)

And, here I am. All these years later. Still running an exclusively online business.

Of course, I don’t own that computer site anymore. I finally sold it and today the Blog Marketing Academy is my primary business. But, all those lessons I learned in an entirely different niche shape how I do things today – and how I teach my students inside The Lab. It is the reason why I focus so much on business fundamentals rather than chasing the shiny objects of the day.

Over 20 years of running different businesses online, experiencing highs and lows, as well as dealing with all the struggles that come with it… I’ve taken a lot a lessons myself. I thought I would compile some of the biggies into one blog post.

Here are 84 lessons I have come to affirm over 20 years of online business, broken down into short, pithy takeaways…

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1. Keep things simple. When you feel things getting complicated, stop and look for what you’re doing wrong.  Power is found in simplicity. Complexity is a sign of failure.
   [clickToTweet tweet=”Complexity is a sign of failure.” quote=”Complexity is a sign of failure.”]
2. It is as important to work ON your business as it is to work IN it. Never get so entrenched in being the worker in your business that you forget to be the CEO.
3. Never, EVER fail to launch a site without building your email list. Your email list is your source of leverage and momentum for a new site. Failing to build it means you will likely never get off the ground.
4. Don’t worry about perfection. Make it good enough. Perfection is often undefined. We don’t even know what it looks like and likely wouldn’t notice it if it were. In reality, absolutes are unattainable. So, get it to “good enough” state then move onto your next project.
5. When you want to accomplish more, give yourself less time to do it. I’m at my most productive when I’m about to go on vacation. I get a TON done beforehand because I KNOW I have a deadline. Tasks will expand to the time allotted. It is called Parkinson’s Law.
   [clickToTweet tweet=”The best way to get a lot done is to cut your available time to get it done in half.” quote=”The best way to get a lot done is to cut your available time to get it done in half.”]
6. This is a people business. They’re not pixels on an analytics graph. They’re people. Treat them as such.
7. Never waste your time trying to make everybody happy. Some people are so busy making themselves unhappy that it is a waste of your time to try to fight them on it. There are some people who will complain no matter what. So, listen to them, evaluate, then decide if real action is warranted. If it is an outlier, forget about it.
8. It is your blog and your list. You own it. You’re the one who does all the work. You pay the hosting bills. Keep that in mind if you have that stray person who complains you are charging too much or don’t do enough for them for free.
9. It is more important to connect with the RIGHT people in your audience, than to worry about raw numbers. Raw traffic figures, comment counts, or even list size are not nearly as important as how many of the RIGHT people you have. Engaged subscribers are more important than raw subscribers. Number of customers is more important than raw traffic.
10. The only proof of a product idea that matters is sales. It doesn’t matter what anybody tells you or how interested they seem… if they aren’t asking you to take their money, take it with a grain of salt.
    [clickToTweet tweet=”The only proof of a product idea that matters is sales.” quote=”The only proof of a product idea that matters is sales.”]
11. Never assume you know what your audience wants. Ask them. One of the most common mistakes I see is people who build a product because they think people need it. It is arrogant… and stands a good chance of falling flat.
12. Who gives a shit how many comments you get? Comments don’t get you paid. Spending time worrying about how many comments your post gets shows you have the wrong priority. In fact, you might even be better just turning comments off altogether.
13. Don’t go into debt to fund your online business. It is completely unnecessary and just adds stress. Don’t buy things for your online business with credit. This is the internet… you can literally make up an offer and make sales out of thin air. So, do it.
14. Creation of valuable offers is how a business makes money. Ad income is just filler income. Affiliate income is a profit maximizer. It isn’t really a real business until you’ve got your own products/services on offer that you sell directly.
    [clickToTweet tweet=”Ad income is just filler income. Affiliate income is a profit maximizer.” quote=”Ad income is just filler income. Affiliate income is a profit maximizer.”]
15. Be a real person. Don’t ever say “we” when it is just “I”. People see right through that.
16. Email list > Social Media List. Building your social media follower lists is practically useless when compared to your email list. Focus on your email list. If a social media “guru” tells you email marketing is dead, laugh at them then walk away.
17. A blog is not a business. Blogs are a great marketing platform. But, they’re not a business. And they never have been.
18. Start or join a mastermind group. It is difficult and limiting to try to build and grow your business as an “only one”, trying to be a hero. This would tends to operate best at a minimum of two. As a solo entrepreneur, it is important to have a peer group to discuss things with. Or hire a mentor to provide a second set of eyes.
19. Being understood is more important than sounding smart. Communication is only effective if it is clear and understood by the people on the other end. Usingn big words to try to impress just makes you stupid.
    [clickToTweet tweet=”Being understood is more important than sounding smart.” quote=”Being understood is more important than sounding smart.”]
20. Balance out “real life” and virtual work. You can only be at your computer for so long before your world closes in and your productivity drops. It is important to balance that mental work out with activity in the real, physical world.
21. Time is a more valuable asset than money. Never spend too much time trying to save a few bucks. In the end, you’re losing money in the long run by taking time trying to reinvent the wheel just to save a few bucks upfront.
22. Technology changes. Platforms change. People don’t. Focus on the people and the rest of it is just a means to an end.
23. Outsource before hiring employees. Some would disagree, but for a business like mine which runs lean and mean, employees are a huge expense. I’ve done it. It was incredibly expensive and the bookkeeping was ridiculous. If you can outsource to a contractor, do it.
24. Change your work environment every so often. Today, my primary work computer is a laptop. I can work wherever I please and it isn’t any different. Coffee shops are nice. Going out in the RV is nice. Hell, sometimes I just work from my back porch. 🙂
25. Don’t skimp on your computer and work equipment. If you plan to make your living with it, the least you can do is not cheap yourself out. You get what you pay for.
26. Don’t be afraid to show your personality. People like it. It makes you REAL. And speaking of “real”, just be REAL. Don’t have a different online persona than you do in real life. It makes things more complicated.
27. Don’t play follow the leader in your marketing. It is really easy to look at what somebody else is doing and assume it is working really well. If you blindly model it, your results may be completely different. Trust me, even the “gurus” sometimes just make a wild guess. 🙂 Not everything they do is working even if they make it seem like it is. What’s happening behind the scenes is often different.
28. Those who make a point to flaunt their success are often not very successful in reality. The joy comes from the game of creating that success, not the end result of it. If I see somebody who is trying to flaunt their money, I immediately look at them as a source of entertainment rather than a source for anything meaningful.
29. Don’t waste time comparing yourself to others. Instead, compare to who you know you can be. Compare to yesterday’s self. Are you advancing? Are you better than you were a year ago? That’s the only true measure. Remember, if you judge people by what they say on social media, you’re looking at their public image but comparing it to your behind the scenes. If you’ve ever watched the raw footage of a movie and compared it to the finished film, you’d be surprised how different it is. Don’t make the mistake of comparing somebody else’s finished film with your behind the scenes footage.
    [clickToTweet tweet=”Don’t make the mistake of comparing somebody else’s finished film w/ your ‘behind the scenes’.” quote=”Don’t make the mistake of comparing somebody else’s finished film w/ your ‘behind the scenes’.”]
30. Don’t buy an internet marketing product because of hope. Buy because you know immediately what you’re going to apply it to and you’re committed to action. Buying internet marketing products and collecting them for “someday” makes no sense. Yes, even if the product you’re buying is mine. 🙂
31. Passive income online is a pipe dream. It takes a lot of time and effort to make a passive income. When it comes to online business, “passive” simply means leveraged time. It means your income and your time are not connected. You can be out doing something unrelated and your business doesn’t shut down. It takes work to get to that point. But, in no way does “passive income” mean you’re not working quite a bit.
32. Don’t feel obligated to keep up with the latest news and trends. Most of it is stuff you don’t need to know. It is noise. The basics remain pretty much the same over time. Until you’ve mastered the basics and your business is humming along really well, you have no business trying to follow every little trend or launch.
33. Never compromise with your own reality. Never let others talk you into being “reasonable” or “realistic” about your goals. What is true is what is true from your perspective. Period. End of story.
34. Don’t ever make promises in your marketing that you can’t deliver on.
35. Your biggest periods of growth usually come when you’re most uncomfortable. Some of my best, highest-revenue periods in my business were when I was stressed out and felt like I was barely hanging on. I was doing things that made me nervous. It felt weird at the time, but now I look at it as a time of growth that I’m grateful happened.
36. Never be scared to fire a customer or client. Sometimes, the customer is not right. Sometimes they’re just being an a-hole and you’ll be better off banning them or telling them exactly what you’re thinking.
37. Low priced customers are usually more trouble. Customers who have paid very little for something are more likely to be complainers and ask for refunds. They are also much less likely to get results. It doesn’t mean there isn’t a time and place for low-priced offers, but you need to keep the bigger picture in mind on this and not rely on it. It is very tough to build a business on the back of cheap crap.
38. Don’t compete on price. Instead, keep your prices within reason and figure out how to compete on service, quality and experience.
39. Don’t let your business consume you. Your business is supposed to support you, not the other way around.
    [clickToTweet tweet=”Your business is supposed to support you, not the other way around.” quote=”Your business is supposed to support you, not the other way around.”]
40. If an email list you’re on never does anything except try to sell you, then unsubscribe. At the same time, realize that every site needs revenue to survive so don’t get annoyed when they sell. Realize it is a balance. As long as you are getting value from that list, stay on it. Otherwise, leave.
41. The first step to making money online is to stop searching the Internet for how to make money online. That phrase “make money online” is flawed because money is a result of service to another, not a platform. Plus, “make money online” will pull up all kinds of scammy crap with a lot of promises designed to take advantage of that mindset. If you search for how to make money online, you’re basically painting a bullseye on your forehead for scammers to shoot at.
42. Take care of your health. Your business doesn’t mean shit if your body is messed up.
43. Don’t put all your eggs in one basket. Have multiple streams of income. You should have more than one offer to make. You should have offers at different price points. You can have some profit maximizers going, such as affiliate sales. But, a business on a solid foundation is not a “one trick pony”.
    [clickToTweet tweet=”A business on a solid foundation is not a one trick pony.” quote=”A business on a solid foundation is not a one trick pony.”]
44. Always try to build a continuity income stream into your business. Recurring revenue is the basis for online business stability. It is how you grow a business over time rather than constantly chasing the next sale or the next launch.
45. Take control of your time. Don’t let others control it for you. This means you deal with email on your terms and not sit there waiting for it. It means you don’t allow clients to run you around. You learn to say “no”.
46. Never hire an outsourced worker without documented processes for them to follow. I’ve done it. It ends up bringing on more confusion and wastes your money.
47. Marketing isn’t bad. It is the lifeblood of your business. Fail to market, you die. Those who think that all efforts to sell something are slimy… will remain poor.
    [clickToTweet tweet=”Those who think that all efforts to sell something are slimy… will remain poor.” quote=”Those who think that all efforts to sell something are slimy… will remain poor.”]
48. Manage by the numbers. Your business needs to have certain key performance indicators that are tracked and measured over time in a concrete way. Then, you make decisions based on the trends of those numbers. It is so much easier than “shooting from the hip” and guessing what to do.
49. Constant preparation for launch is just a search for excuses not to launch. Knock it off and deliver. As my grandfather always told me, the only way to catch a fish is to have your hook in the water.
50. When you find that something you did was successful, then do more of that. Not everything you do has to be “new”. In fact, it isn’t very smart. When you find that something was working, you should systematize it so that it will continue, no matter how boring it is.
51. Be willing to question the status quo. Constantly be on the lookout for things you do which are not leading to results and stop doing them. Just because you’ve been doing something habitually for awhile doesn’t mean you can’t change your mind.
52. Don’t create big products just for the sake of it being big. Focus on what is needed to deliver a result. The customer wants a result, not a big box of crap which will overwhelm them. The “bigness” of a product doesn’t justify a higher price. Only results do.
    [clickToTweet tweet=”The ‘bigness’ of a product doesn’t justify a higher price. Only results do.” quote=”The ‘bigness’ of a product doesn’t justify a higher price. Only results do.”]
53. Don’t throw everything and the kitchen sink into a product offering. It is too hard to market. I made this mistake with my first launch of Blog Masters Club. The training covered so much ground that it was hard to narrow down a cohesive marketing message.
54. Whenever possible, never create a custom solution that only you know how it works. I used to run my business using custom solutions, many which I built myself. The problem was that I was the only guy who knew how it worked. I was the only person who could fix anything. Contrast this with a platform like Wordpress where you can accomplish almost anything using third-party plug-ins that others created and support. Today, I will avoid anything custom if I can help it. Only create something “in house” when it is an absolute necessity.
55. Marketing automation is an important component to growing and scaling a business. You can’t automate everything, but many things you can.
56. Don’t keep information in your head. You won’t remember it. I use tools like Evernote and Dynalist to keep “to do” items and other things out of my head.
57. Focus on how to make more money before you focus on how to cut your expenses. Income and expansion should be the focus, not only shortages. Focusing on shortages breeds more shortages. The solution to “not enough money” is to make more money.
58. Learn how to say “no” and not feel bad about it.
59. Set money aside for taxes. It sucks when you forgot to plan for it.
60. Keep a budget and stick to it. Real businesses do real accounting, budgeting, and income/outgo tracking. It is small-time thinking to make spending decisions based on your bank balance.
61. As you make money, sock some of it away into long-term assets. Online businesses come and go. The dollar is only as good as the confidence in it and it won’t last forever. Hard assets of lasting value are a way to make the earnings of your business ever-lasting.
62. Keep your tasks clear and concise and know exactly what you’re shooting for. Otherwise, you’ll spin your wheels and nothing will get done. Know exactly what “done” looks like so it is crystal clear when you’re finished.
63. It is better to do less and excel at it, than to do more and be only mediocre.
64. Get plenty of sleep. Burning the midnight oil quickly leads to burnout, and your work suffers. While you may do it occasionally, having a better balance so you don’t have to is preferable.
65. Work in batches, and combine like tasks together. For example, write all your blog posts for the week in one sitting. Get it done so you can focus on other things for the remainder of your week. Multi-tasking is usually grossly inefficient.
66. Blogging every day is a waste of your time. Today, I focus on The Redwood Strategy and it is far more effective.
67. The less time you spend on social media, the richer you’ll likely be. Social media is literally designed to be addictive. If you’re on there quite a bit every day… congrats. You’re an addict.
68. Keep your workspace clean. Cluttery offices make cluttery minds. Usually when I feel myself being a little scattered and unfocused and not knowing what to do, I simply stop and clean my office. It helps.
    [clickToTweet tweet=”Cluttery offices make cluttery minds.” quote=”Cluttery offices make cluttery minds.”]
69. Online business isn’t much different than regular business.
70. A product means nothing if it isn’t delivered.
71. Don’t spend too much time worrying about an unethical few. Don’t fail to bring a product to market because you’re worried about people stealing it and redistributing it without paying. Employ reasonable safeguards then move on. Focus on your real customers, not on those unfortunate few who have already failed because they try to steal. They won’t succeed because karma will bite them in the ass. In reality, very few will try to rip you off anyway so why waste much time worrying about it?
72. Working smart is more important than working hard.
73. If you’ve got nothing new to say on your blog, don’t stress it. Simply don’t post anything. Your blog isn’t the business anyway.
74. Some people are meant to be employees and not entrepreneurs. And there’s nothing wrong with that.
75. The only way to truly survive is through constant improvement. The moment you become comfortable with the current situation is the day you start withering away. You must be constantly CREATING your business for it to grow. Create it like an artist.
    [clickToTweet tweet=”You must be constantly CREATING your business for it to grow. Create it like an artist.” quote=”You must be constantly CREATING your business for it to grow. Create it like an artist.”]
76. Information overload is easy to solve. You simply stop paying attention. You’re in full control of your attention. Nobody else is. Stop wasting your valuable resource.
77. Don’t sell from your heels. If you feel back-off at the idea of selling your product, then you need to re-visit your product so that you can make it so important to your prospect that you’d be doing them a disservice not to get them to buy it. Create a product you believe in so that you’re excited and compelled to sell it to them because they will love it.
78. Practice inbox zero. If inbox zero is a lost cause for you, then it is time to re-organize your incoming lines of communication. It means you’ve lost control.
79. Separate planning from execution. It is inefficient and ineffective to try to make decisions on what you’re doing while you are doing it. I do my best work when I plan out a project before I sit down to actually do it. It actually takes less time doing it using this two-phase approach.
80. Be willing and able to accept responsibility. The moment you look to others to provide for you, or blame others for things which aren’t going right for yourself, you have failed. Taking responsibility doesn’t mean taking “blame”. Responsibility isn’t the same as blame. Responsibility is the willingness to CAUSE something. And if you’re not willing to cause things, pack up, go home and get out of the way.
    [clickToTweet tweet=”Responsibility isn’t the same as blame. Responsibility is the willingness to CAUSE something.” quote=”Responsibility isn’t the same as blame. Responsibility is the willingness to CAUSE something.”]
81. You have more freedom when you impose barriers on yourself. Many like the idea of online business so they have no rules, can get up when they want, can do what they want. In reality, that “free for all” life is pretty unsuccessful. Freedom without barriers is a recipe for nothing. As an entrepreneur, when you impose order and discipline on yourself, freedom will result.
82. Systems and checklists isn’t just for the big guys with big teams. Systems and checklists means you’re creating an asset that can exist outside your own head. It is a prerequisite for freedom and expansion. It puts order into your day-to-day activities.
83. The way to make more money is to make more offers.
84. Not everything in business should be scalable. In fact, some of the biggest growth opportunities in business today are by doing what is NOT scalable.

I hope you found some value in this. It took me some time to put together. 🙂

If you did, I’d appreciate it if you share it or quote me out on social media. Thanks in advance!