One of the questions I’m asked most often is how to actually get started and confidently invest. It’s easy to get frustrated with always consuming content and never making that first bold move. It doesn’t help that my conversations are always with accomplished, alpha-types who have been successful in their careers.  

So, how do you gain the confidence to take the first step to buying an established website and securing your future?

The Beginner’s Curse

I have a friend named Alan who I’ve known for a few years professionally. We met through an outside interest and stayed in touch. He has regularly asked me about our e-commerce activities. I’ve made suggestions to him on what to read and he even bought a great course I thought would help him.  

In one of our conversations Alan described a problem I faced myself for a long time:

                        “You know a lot, but you don’t know where to begin.”

                              Alan, London UK, on “The Beginner’s Curse.”

You can and will waste a lot of time wandering around in the dark without any notion you will ever execute on anything. I spent too long trying to solve for this myself and feeling more insecure every day.  

Now my look backwards tells me there are three critical elements to analyze to insure you maximize your opportunity to succeed and gain the confidence to act.  

How to Start

First you need to picture the end state that will make you happy. Determining this is critical to helping develop your “why.”  In my view, it can’t be about some monetary goal without a human connection. In my case I was staring at retirement with two younger kids and not enough savings. I had real urgency (and still do).  

Without a solid reason for making the sacrifices you will make, you will not push through the inevitable tough times and self-doubt that ensues from tackling the complexities of owning an online business. I assure you your mettle will be tested and things will not go as scripted. Not even close.

The next necessary thing to do is assessing your own strengths and mapping them to success in building and running an online business. You’ll never be certain, as you do not actually see yourself through the lens a successful veteran does. Handicap this with not knowing the importance of even minor differences in competency levels and it’s hard to feel too certain you’ll succeed. But most of us have a good idea of what we do well.

Commit to mastering a core set of skills and understanding well areas you’re deficient.  Ultimately you’ll need to surround yourself with experts who you direct. You’ll need your core skill as an edge and a good team around you to succeed.

Finally, it’s easy to tell when someone is lost when they have not focused like a laser on a specific monetization strategy. They are perusing Flippa looking at everything from AdSense to SaaS sites and anything in-between. But picking the right monetization strategy is practical analysis once you know the moving parts.  

You need to assess where you want to end up and leverage your unique strengths. You then need to contrast these with what a specific monetization model requires to succeed.

These are the three components you need to get correct:

  • Your desired end state
  • Your skill assessment
  • Your monetization strategy

If you don’t, you’ll likely fail or be unhappy, or both.  

You can start to visualize your future easier and begin to feel some confidence. However, this feeling won’t be permanent. You just don’t have enough evidence yet.

How to Know You’re Right

Tom Corley from The Rich Habits Institute says you cannot think your way to confidence. Confidence must be earned and you build it one level at a time. Corley defines the 3 levels as: 

  • LEVEL #1 – Expert KnowledgeHaving specialized knowledge in a particular field or niche.
  • LEVEL #2Expert Knowledge and Advanced SkillsHaving both Expert Knowledge and Advanced Skills in a particular field or niche takes you to the next level, elevating your confidence even higher.
  • LEVEL #3Expert Knowledge, Advanced Skills and Achieving Success — You can attain the highest level of confidence when you have mastered all three levels: Expert Knowledge, Advanced Skills and Achieving Success. This makes you a bona fide expert in your field or niche.

Most career professionals I know have Level #1 Expert Knowledge, many in more than one area. If you have excelled in your career over 15 years or more you have likely mastered more than one competency. You can trust this is the case.

As I described earlier, the problem is you may not appreciate what you possess. But I speak to people every day with unexploited “superpowers” I envy. Don’t get stuck here.

Level #2 is trickier for people trying to extend themselves into the online business world. Traditional careers and professions don’t usually allow you to build the required Advanced Skills to succeed in online business. Fortunately, great courses are available to augment an enthusiasm for acquiring the right Advanced Skills.  

But courses are static and you will not feel truly confident about your proficiency. You need to do the work as it’s prescribed by the experts and understand the concepts well enough to teach them to others. Most courses have forums now where you can do exactly this.

Level #3 can only come from succeeding. The irony is that most successful first-time online entrepreneurs harbor deep insecurity—they think they got lucky— for a long time after they have truly succeeded. Setbacks occur constantly, so you worry it’s all going to end for some unforeseen reason.

Many who are successful for the first time quickly sell a profitable business to lock the in the profit. Others worry their success is not repeatable. But the reality is many who have just experienced first time success can likely replicate this on some level.  

The only way I know to succeed is by doing. The best way to start is to beta-test your skills with smaller investments that will help you learn and build your confidence.


Most late career professionals have excellent Expert Knowledge. They just need to assess it correctly.

Excellent courses exist to help people seeking to develop Advanced Skills that are relevant. You must choose the right course to fit your specific need, and maybe some expert help.

Achieving Success requires making a commitment. Take a venture capital approach to investing and make smaller commitments.

Follow this plan and you’ll develop real confidence in your investing based on your success. Keep this framework in mind and you may also spot a successful but fearful seller, offering you an excellent opportunity to invest.

My mantra is, “You’re just a deal away.” This can mean your retirement is secured, you can fund a college education, or you can fire your boss and travel the world.

If you’re interested in joining our program to level-up your knowledge base and save yourself time and money, send me an e-mail and let me know your situation.

2 Comments. Leave new

  • What about an article on the different monetization strategies and pros/cons? I think thats my next step, choosing a strategy.

    • Hi Tim! I just published on physical goods being the best first investment. I’m thinking of contrasting drop shipping (my favorite), FBA, and wholesale. Send me an email with your thoughts on where you’re at. Thanks!


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