80 Lessons From 19 Years As An Online Entrepreneur

A summary of 80 lessons that I have learned over the course of 19 years as an online entrepreneur, through highs and lows, and different businesses.

  • Larissa says:

    It is Awesome!!!!!!!!

  • lorrainegrula says:

    I guess 14 internet years is equal to 84 dog years.  You are an old coot!   🙂  I’m 54 so that makes me ancient.  This was an excellent post David.  No doubt you could take that post, expand on it and turn it into a one hour video.  There is so much wisdom in this list.  Thanks, as always.  I’ve been doing this for 6 years now and even with all the ups and downs, it has been rewarding and fun.  Compared to so many others who give internet marketing advice, you are a breath of fresh air.  You are practical and honest, not  just spewing swipe copy crap and giving false promises.   

  • Tasi says:

    That’s awesome, Dave

  • Will Atkinson says:


  • Will Atkinson says:

    Excellent, excellent, excellent! Everyone in Internet marketing should read this post, regardless of skill or experience. Good job, David.

  • Matt says:

    Great post!  I’m relatively new to the blogging world and this post will most likely save me weeks of running in circles.  Blogging is pretty much a hobby for me now because I love doing it but haven’t really tried to make any income from it, yet:) Thanks for your insights!

    • David Risley says:

      No problem. Just remember, doing it as a hobby and as a business aren’t necessarily the same. Doesn’t mean you can’t enjoy it like a hobby, but it does mean that the considerations are different.

  • Are Morch says:

    Hi David.

    Now I think my mind is younger then what my birth certificate tells me.. lol

    It was a valuable list here of great lessons learned. And the cool thing about it that some of these lessons you passed on to us that drops in here either on your blog, or that taken part in some of your training. 

    One of the most important lessons I learned is that this journey is not about taking perfect action steps or have detailed map that guide you to your destination. 

    It is actually ok to take imperfect action steps, and yes sometimes it also totally ok to take a scary detour without really knowing where you are going. Sometimes even the best have hickups and they just move on. 

    One of the things I found incredible value was to get a mentor or accountability partner (not sure if this goes along with your MasterMind group). Here I learned that I was a perfectionist!!(?? never knew). So I can now conquer to your point to settle with ‘Good Enough’. Is it scary to do things I never done before? You bet it is.. but I have more fun then I ever had. So as I started out with my mind is now younger then my birth certificate. My good friend John Haydon told me that a child smile in average 400 times per day. So I everyday now I deliver some childish service 😉


    Are Morch
    Hotel Blogger

  • Tatum says:

    Great info. Thanks!

  • Nice list Dave. 
    – I need to remember #26 & #36
    – I’d love to be able to do more of #56 but it takes me too long to write sometimes to make that an option.
    – #59 Cluttered Desk = Cluttered Mind…What does an empty desk = ? 😉

    I’ve learned that I still have a lot to learn.

    – Chris

    • David Risley says:

      Empty desk is usually a good thing, not to worry. 🙂

    • PJ Brunet says:

      I agree with David, but there are exceptions and extremes.  Some intelligent people are capable of processing tons of information.  And there are some disciplines where you’re not working with cute apps all day.   Random example, if you write historical non-fiction, you might be working in an old library with old photos and books piled around you.  Just look at the cockpit of the space shuttle, it looks like clutter to the outside world but it makes sense to the astronaut.  Maybe the other extreme is a sensory deprivation chamber, j/k.

  • Bernd says:

    Awful list, David. Excellent!
    Love 31: “Your biggest periods of growth usually come when you’re most uncomfortable. Learn to accept that.”
    It is so true!

  • Mk Akan says:

    thanks for this…very many golden nuggets here…my issue is with creating big perfect products…thanks 

  • Thank you for valuable lesson, thanks Dave. Good work!

  • Peponne says:

    David, I’m truly impressed by your professionality, your down-to-hearth-no-nonsense attitude, and above all, your stupendous generosity. I expect to be doing business with you real soon. Best regards!

  • Kat Lessin says:

    Thanks David.  Today was the perfect day for this post.  So what I needed to hear.  Well thought out and very valuable insights especially from your experience being an “older person in the room” or in this space. 🙂

  • This! #55: Get plenty of sleep – Working all night is a sure way for the following day to be almost entirely useless. Beyond that, it’s unhealthy. I choose sleep over work as much as possible because I perform better the next day, and I get more done in less time. #31 is always true, without fault. I wish there was an easier way, but great periods of growth seem to happen only when I’m uncomfortable.

  • Cody Wheeler says:

    Lot’s of productivity tips in here. I dig it. Question for you Dave – What would your Top 3 of these be that are actionable today? I see keep things simple in there, but then I see 65 tips that sort of overwhelm me to read and 95% of which I’m not going to remember. Maybe it’s hard to narrow it down that much. What are the heavy hitters here dude?

  • Daniel says:

    Why do you say being 34, you are considered the “old” crowd?  Aren’t most bloggers varying in ages anyways?  I read other bloggers and they all vary in ages, from early 20’s to 30’s.. and through 50’s +

    • David Risley says:

      You’re right in the general area of blogging. I was referring mainly to the people in the same niche as myself, in other words the whole “blog about blogging” thing. Most of the people I know in this market – and people you may know, too – are older than I. Plus, there’s the experience factor since I’ve been doing this longer than most.

  • Debbie says:

    Great article. Been indep contrctor about 20 yrs and now deciding to get website, blog, etc. Just have question about number 3 ….I want to come across like I have small business and am writing content as “we” instead of “I” so people do NOT think it is just some rinky-dinky co. However, sounds like I am way off. Right?

    • David Risley says:

      I don’t know your business, but in general, there’s nothing wrong with embracing the fact you’re a one-person show. These days, people like doing business with real people and not feel like they’re just a number in a big factory.

  • Danny says:

    Summary: be irreverent, make it rain.

  • Mike says:


    It’s crazy to think that 34 is old in this business. I’m right behind you at 32.

    I liked # 3 “Never, EVER fail to launch a site without building your email list. If you’re not building your email list, you are completely wasting your time and you’ve already failed whether you know it or not.”

    Everyone always talks about how important starting a list is. Why? Because it is!

    • David Risley says:

      Yep. People don’t do it because they don’t want to pay the $19 for Aweber or something, but its such lame thinking if they’re at all serious about building a business.

  • ES says:

    The point, ‘first step to start making money online is to stop searching for it online’, is an exemplary statement. It does require a few years to understand it though 🙂

    • David Risley says:

      Yeah, I could elaborate on it. But, its also simple. Making money comes with delivery of an outcome to a market who needs it. When people search for “how to make money”, they’re starting with the end result. Nobody starts a business with the thought, “I’ll do whatever makes me money.”. People in the real world understand about delivering value to a customer. “Make money online” searches will just lead people astray.

  • I could not agree more with the bonus Dave.  As an Officer in the Army for 8 years, I had many superiors.  The only ones I truly respected were those willing to accept responsibility.  I try and lead my life/business by that mantra.  It’s easy to blame others.  

  • Thanks for the motivation! I just finished setting up the email list for my blog. Now I need to work on marketing.

  • Your shared a huge and comprehensive list of tips. To get great results for business your tips are very important and workable, i will try to get benefits from your experience.

  • MikeHaydon says:

    Is the choice of 65 because you’re so old in internet years that you’re ready to retire? Just kidding. Great list and something that bears further study. Thanks.

  • Ela Zyrek says:

    This was huge, David. I really like this article!

  • Ela Zyrek says:

    This was huge, David. I really liked this article! Thank you@elazyrek:twitter

  • As a side note, I wanted to share this on my Facebook page through my smart phone, but there was only a ‘like’ box. So I couldn’t share it..

  • Thank you David for telling it like it is. I know I only discovered you a few weeks ago but you restored my faith in business that operate online. Yes – business is business – regardless of where it occurs – the same rules need to apply. 

    Taking your awesome advice (and mine) – I’ll be logging off for over 3 weeks to nurture my ideas and churn them out as realities vs. half hearted, exhausted brain farts … 
    To creativity and telling it like it is! 

  • Swamykant says:

    That’s Awesome list, David

  • Hello David,

    Too many similar thoughts 🙂

    I’ve started list building after reading one of your posts (about 3 months back!). And I’m not at all worrying about the comment count (before I used to worry about them, this pissed off me).

    But I’ve one question about the 9th point. How to find the ‘right’ audience for my blog? 

    Any help?


  • Another great post David. #49 is one people need to remember 😉 

    My brain is a mass of wrinkly grey awesomeness, but it has so many great ideas locked away in it that I just can not recall. You need a great system that allows you to store and categorize your ideas in a way that will enables you to recall them and actually ACT on them.If you rely totally on your brains ability to recall those ideas, you will flush many great ideas away.

  • Thanks for this awesome list David! I think I have to write down some of it in my notes as a reminder.
    One thing I need to put as my laptop wall paper is “The less time you spend on social media, the richer you’ll likely be.” hehehehe…
    Closing down my FB now 🙂


  • Murray Lunn says:

    Number 28, all the way.

    “Don’t feel obligated to keep up with the latest news and trends. Most of it is stuff you don’t need to know.”

    I can’t even begin to tell you how quickly you can be swept up into this “need” for keeping up-to-date with every tid-bit of information. Doing so not only burns you out but has you chasing these goals that don’t truly matter. Yes, it’s important to understand trends but if they get in the way of business than they’re just a distraction. Keep your head down, work on what matters, get shit done. Plain and simple.

  • Glynne says:

    Great advice David.  What I want to know is how can you build a list if you have nothing to sell?  We (yes it is ‘we’) have a humanitarian website raising awareness and funds for global charities.  Not certain how to encourage people to sign up to our list?  Any suggestions?

    • David Risley says:

      You don’t need anything to sell to build a list. It is all about capturing the emails of people with similar interests. You could build a simple update list for global happenings to bring charitable events to people’s attention, for instance.

  • Kathleendeane says:

    Those were amazing insights! All of them I believe are spot on! Thank you for compiling them for others benefit

  • Evette says:

    Thank you David for putting this list together and sharing it, great info.

    Thank you!!

  • robinhallett says:

    Wow, thanks for this, David. I can tell you worked hard 🙂 I learned more than a few dozen of these the hard way myself! I really appreciated your suggestions of what other pitfalls I might avoid (digital baby here). All the best to you, David!

  • Manuel says:

    David, I found your blog by chance and I must admit that you have really done it. I read this post in its entirety and I agree with 99% of your statements. Thanks for sharing your knowledge.

  • leckyt says:

    Wow! Awesome list!

    Now, on to the other great resources; so much to learn…

    If the rest of the free stuff is as good as this, I can’t wait to sign up for the paid stuff, too!

  • Simon Zaku says:

    What a super article here, David!

    I’m caught up with some of the lessons you shared with us above.

    Lesson #4. Don’t worry about perfection: As a new entrepreneur and also new in the online marketing space, I always get this feeling “this needs to be perfect, Simon!” but it’s not true. I’ve seen things go well when I let the mistakes happen and forget about perfection.

    Lesson #5. When you want to accomplish more, give yourself less time to do it: As someone who has set goals, I’ve found that I get things done not only when I give less time but also when the goal goes public. The fear of ‘public shame’ gets in me and makes me want to work. It might be different for some people though.

    #Lesson #12. No one gives a shit about how many comments you get: I might slightly disagree with this lesson. Yes, getting tons of comments doesn’t give you more money directly but you can get insights that can get you more money. For instance, lets say I wrote a blogpost about a problem my target audience faces then you end it with “have you had the same problem? Share it with us!”

    I might end up getting tons of ‘audience problems’ in that comment alone. So with my short experience, I believe comments can be worth it. Sometimes I find myself checking the number of comments first before sharing one. It shows there’s a community here. Real humans are here.

    Thanks & congrats on your 19th year.


    Simon Zaku.

  • Morgan Reece says:

    Great list, and very helpful. Shared on my Facebook page. 🙂

  • Congrats, David on your ‘anniversary’. Thanks for taking the time to compile this list through the years. Continued success to you.

  • Hi David, Great post !
    Could I translate it in French, with Link to your Blog on my own blog (ConseilsMarketing.com) ?

    It is very inspiring, and remind me a lot of Tim Ferris ;D

    Have a nice day

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