If I Had to Start Over, This is What I’d Do Differently

Today, I’m sharing everything I would do differently in my online business if I had the opportunity to start over from scratch!

This is a follow up to my last post, the history of my first online business.

I’m often asked: If I had to start over again, knowing what I know now, what would I do differently?

And more importantly, why?

There’s a lot, so let’s get right into it…

I Should Have Been Proactive—Not Reactive

When I created a blog to help me keep track of my notes and pass the LEED exam, that was being proactive.

Starting my first online business only after getting laid off, when it was an opportunity I had all along? Reactive.

It was my lay off that forced me to look at my other options and give internet business a shot, and it’s pretty sad to realize that without the layoff to push me forward, I guarantee I would have never ventured into the online space.

I wasn’t looking for opportunities, and I was very close to missing this one.

I’m not saying that you should quit your job to start your own business—I never encourage anyone to straight up quit their jobs without a plan.

What I am saying is that we all have the option to either be on offense or on defense.

I should have seen the opportunity I created and run my LEED exam business on the side while I still had my 9 to 5 job, but because I wasn’t being proactive I let the site sit stagnant for months until I was finally laid off.

And when you consider that in the early days, after I began monetizing the site, it was generating $20,000 to $30,000 per month… it’s pretty crazy.

Are you on offense, or are you on defense?

I Should Have Been More Confident in Myself

There are a lot of instances during my online journey, especially in the beginning, when I did not take action because I wasn’t confident in myself and my abilities.

For example, when I was told by a successful colleague to write an ebook for my site, I thought of every excuse not do it:

This lack of self confidence delayed any sort of action on my ebook, and it was only after several other people begged me to write it, including a couple of my own readers who heard I had thought about it and said they were already waiting to pay for it when it was finished, did I finally take action and do it.

As a result:

If there’s anything I’ve learned, it’s that “my inner world creates my outer world”, which is actually a quote from Secrets of the Millionaire Mind by T. Harv Eker, a great mindset type book that I recommend. [Full Disclosure: As an affiliate, I receive compensation if you purchase through this link.]

In other words, if you don’t think something is possible, then you’re probably right—it will never happen.

Nowadays, I try to instill confidence in everything I do—from blog posts that I write to public speaking, and I recommend you try to do the same.

I Should Have Priced My Ebook Higher

When I launched my first ebook, I sold it for $19.99.

After the first month, it generated $7,126.91, which I was extremely happy with!

Halfway through the second month (November of 2008), I receive an email from a customer who purchased my ebook. He also happened to be a business owner and he gave me some amazing advice along with his email.

Paraphrasing, he said:

“Pat, your book is excellent, but you’re selling yourself wayyy too short. Your guide is definitely NOT a $20 book. Please raise the price, I promise you it’ll be better for everyone.”

To be honest, I really had no clue what I was doing. I was happy with $19.99 because it was way below the price of any other guide on the market, and my thinking was that the lower the cost, the better, because a low price is attractive.

What I eventually learned is that yes—a low price is attractive, but only to certain point.

It depends on the product, but if the price gets too low, it cheapens the value of the product in the eyes of the customer to a point where they won’t buy it anymore.

After that (amazing) email, I raised the price for the rest of November to $24.99 (probably should have done more). Then in December, to $29.99.

Here are the results:

Beyond the increase in earnings, I actually saw an increase in the number of units sold each month as well—which is amazing. A higher price seemed to yield a higher conversion rate!

That said, the price can only go up to a certain point before it’s viewed as “too expensive”—and after testing $34.95, $39.99 and $49.99—the $29.99 price point turned out to be the sweet spot.

I’m glad I got that email—because even the smallest price change over a long period of time definitely add up.

It’s been 3 years since.

That $10.00 difference between $19.99 and $29.99, even at a rate of only 1 sale per day for the last three years, adds up to $10,950.00.

I Should Have Chosen a Better Domain Name (And Understood Trademark Infringement)

One of my most interesting and stressful business experiences happened when I received a cease and desist notice& asking me to immediately shut down my LEED exam site, or else legal action would be taken. They gave me a week to shut things down.

The reason for the letter was because I was using a trademark “LEED” in my domain name—which is a no-no. My domain was previously at intheleed.com before I switched to GreenExamAcademy.com.

Even though some companies don’t care about people using their trademark in domain names, many companies do—but either way if you do use a trademark in a domain name you take the risk of a company, at any time, nailing you for it.

I ended up hiring a lawyer the same day to fill me in on the details, and let me tell you—those fees adds up quickly!

I was basically told that I did have a slim chance of keeping the domain name if I wanted to fight for it—but it wasn’t worth the stress, price and hassle, so I was (er, my lawyer was) able to negotiate that I simply change the domain name—since the mark was the real issue.

I bought GreenExamAcademy.com and did a 301 permanent redirect to keep all of my link juice flowing and rankings up in Google, and anyone who went to an old link would be automatically redirected to the new page.

All seemed well, until I was contacted AGAIN with another letter saying that even the redirect was technically still a use of the trademark, so I had to get rid of the 301 redirect and close the domain.

Luckily, enough time went by that Google picked up on the new site so I maintained MOST of my rankings and traffic.

Definitely a learning experience…

Don’t use a trademark in a domain name unless you have the rights or license to do so.

I Should Have Started My Email List Right From the Start

One of the biggest mistakes I ever made (and I made it twice!) was not starting an email list right away.

With my LEED exam site, I waited an entire year after monetizing and selling my ebook before I started to get serious about collecting email addresses.

E-junkie [Full Disclosure: As an affiliate, I receive compensation if you purchase through this link.], the shopping cart that I use, has basic email capabilities, but only those who opt-in during the billing process can receive emails, and even then there are not that many features that come with it.

Just think, a year’s worth of customers and I had no great way to contact any of them.

I had no way to tell them about the new audio guide that just came out, or that there was a coupon code that they could use or give to their friends during the holidays.

Big mistake.

And you would think that I would have learned, but I didn’t even start building the email list for The Smart Passive Income Blog until January of 2010, nearly a year and a half later after this site was born.

Better late than never, but better now than tomorrow.

Here’s my beginner’s guide to starting a newsletter so you can start building your list right away if you haven’t already.

I Should Have Done More Video

Video has been amazing for the growth of the Smart Passive Income brand. At nearly 1.5 million video views and 8,200 subscribers (I’ve already reached my 2012 goal! Time to re-goal!), it’s definitely put my brand in front of more eyes, and I know it has helped with SEO and keyword rankings for posts on my blog as well.

With GreenExamAcademy.com, the only video I created is a screencast of some of the features within my ebook—and that’s it.

I definitely missed out on a lot of opportunity there, so if I could go back into time, in addition to studying by writing down my notes on the blog, I would create videos for it too.

I bet by recording myself talk about the material, I would have learned and mastered the material even faster, and at the same time become an even bigger authority in the space.

I Should Have Built a Thriving, Long-Term Community

The biggest regret I have with my first online business is that I did not build a real, thriving community.

I had a small community of people, at times, in the comment section of the blog, but those people would always change as each person finished up studying for their exam.

There were a number of (dumb) reasons I didn’t create a community on my site:

  1. I thought that an off-site forum, one which I was a part of and always referred to on my blog, was a good enough community solution for my audience. Now that I look back, I think everyone would have benefited much more by being part of a community on the same site they were studying from. Not very proactive of me.
  2. I was so convinced that once people passed their LEED exam, they would be done with my site for good. Instead, I should have taken the opposite approach and thought that my site is not just for passing the exam, but for building relationships that can be useful even after people pass the exam. Not very confident of me.

An on-site community or forum would have been an amazing resource for testimonials, case studies, immediate feedback, a place to recruit affiliates, and a source for post-LEED exam related products I could have sold related to the field. When the traffic was up to 8k to 10k visitors a day that would have been amazing. Now, the traffic has died down, the industry is changing and it’s sort of in a transition period right now.

With Smart Passive Income, many of you know I have an active Facebook community of 21,000 people, which is awesome, but I am planning on something on-site sometime in the future 😉

To Finish Up

A few key takeaways here are:

  1. It’s obvious I’ve made a lot of mistakes along the way—but those will never stop me. Mistakes are good, failures will come, and as long as you learn from them and keep moving forward, you’ll eventually get to where you want to be.
  2. I’m going to reiterate the importance of confidence in your business. Even though it’s just one section of this post, it actually pertains to many of the others—like pricing, being proactive, doing more video and building a community. Being confident will take you a long way, and if for some reason you’re around a lot of people who just seem to drain your confidence, don’t hang around them anymore—or find more ways to connect with people who will lift you up instead.
  3. There are always things that you “should have done instead”—that’s just the way life is. Don’t dwell on it though, because you can’t change the past. You can only change your future, and the future of others—which is why I shared all of this with you today.

Thanks, and please enjoy the rest of your week!


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  • Pat Flynn

    Hi, I’m Pat, founder of SPI and host of the Smart Passive Income Podcast. Let’s continue the conversation over in our communities.

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