Leaving Work Behind

5 Lessons From 5 Failed Online Business (That You Could Be Making Too)

Written by Guest Author on January 26, 2016. 16 Comments

Tom: The following is a guest post written by Tom Hunt – the Founder of Virtual Valley, a platform that connects entrepreneurs and rockstar virtual assistants, with the mission of giving entrepreneurs back one million hours of their time by 2018. Subscribe for his weekly bootstrapped marketing tips here.

Did you ever think that you could simply throw up a landing page describing your product or service and that people would immediately flock to you? Or that you could tweet your link to an influencer with 1.7m followers and he/she would retweet it to an eager audience?

I did.

And as I sat there refreshing my Google Analytics stats on my first online business, I was both confused and disappointed. Out of the billion websites out there, why are people not spending time on mine?

Then, slowly, I started to learn…from mentors, friends, websites, blogs, books, seminars – and most importantly, from experience.

With the above in mind, in this post I will share my five greatest lessons from five of my online business ventures that ultimately “failed” (though more on that later).

1. Self Help Book Blog

Let’s rewind three years…

For the previous six months I had been a voracious reader. As writing was the most effective method for me to learn and retain information, I kept notes of much of what I read.

After amassing a lot of notes, it occurred to me to create a blog that collated and shared my book summaries with the world.

I eagerly headed over to a freelancer marketplace and hired a developer to bring my vision to life…

Now, bearing in mind I have zero design experience, do you think I went for the safe (i.e. WordPress) route, or a completely custom design that I thought was “elegant”?

I’m sure you can guess.

We built the site, uploaded a number of book reviews and placed Amazon affiliate links at the end of each review.

Amazon Associates report

As you can see from the image above, the traffic hasn’t exactly been “flowing” over the three years (the ~2% conversion didn’t result in any payments, as this was me purchasing books.)

People will come to your website if you give them what they want. On this project I had focused mainly on making the site look “good”, rather than giving people what they wanted.

On the plus side, I did manage to secure interviews with Dave LoganRobin Baker and got an email from Seth Godin:

Email from Seth Godin

Lesson learned: Focus on helping people first and foremost. Everything else comes later.

2. Supralinks

As traffic to my Self Help Book Blog was dying down and my drive to leave my corporate role was increasing, I thought: Why not just buy an existing online business?

So I did…two in fact.

Flippa is a great place if you know how to use it. I didn’t.

One of the businesses I purchased cost me around $1,000. It still makes around that each month now (completely outsourced). The other was Supralinks – an article writing service that had extremely attractive traffic and sales statistics on its Flippa listing. Maybe too attractive for the age of the domain or the Alexa ranking.

However, I happily handed over $3,200 to a man somewhere in the world only to discover that the traffic and sales stopped abruptly. In fact, it seemed like they never really existed at all.

After a couple of months of hapless marketing I decided to put the project to rest.

In summary, I could have potentially saved a significant amount of time and money by verifying the data claimed by the Flippa seller.

Lesson learned: Trust, but verify.

3. Outsource Your Tinder

About a year on from the previous lesson, I had started to use Tinder a lot.

I was inspired by the ease in which an attractive, well-designed landing page using Strikingly could be set up, and also that a couple of friends were starting a Tinder profile optimization service. I thought: Why not just provide a fully outsourced Tinder service for a monthly recurring fee that guarantees a certain number of dates per week?

I bought the domain, created the page and integrated a PayPal link for $49 per month guaranteeing one date per week. I then created a Twitter account and shared the link with a couple of friends.

A week later I actually started to investigate into how it would be possible to deliver the product. At the time Tinder did not allow you to swipe in other locations, and the solution would require some tricky VPN stuff I knew little about if my outsourced team in the Philippines were to deliver the service (under my instruction of course).

In response to my findings, I refunded our first customer and increased the monthly fee to $149…

PayPal receipt

Maybe I was started to get the hang of this online business thing?

I had learned from the first lesson learned above to give people what they actually wanted and had found people looking for my product. I even managed to rank in the number one position in Google for “outsource tinder” within a couple of weeks and had a reliable, proven design.

However, I had not completed enough research on how the service would be delivered and had a number of other projects on at the time, so decided to refund our second customer and leave the site as it was.

Lesson learned: Ensure that you can and want to deliver the service you (plan to) offer.

4. The Girlfriend Funnel

Remaining in the same niche, I started to develop my knowledge more broadly in the dating world.

At this point I had quit my job and was running a small outsourcing company in Europe from my laptop. I was aware that I learn best from writing notes and teaching, so why not try again?

I installed and customized a WordPress template on a domain and planned to target the keyword “how to get a girlfriend”. My plan was to build an email list over three months before launching my first product (which would teach guys how to get a girlfriend).

I started pumping out content every day and was getting a little bit of traffic and building a small list. Here is my weekly subscriber list:

Email subscriber growth chart

The problem here was that I had no audience.

I was providing value and had a good, proven design, but the email list growth was too slow for my product launch goals (it required a 1,000 person list but only reached around 200 by the time of launch).

I have since discovered where I went wrong: I didn’t know enough about the industry and did not know enough people in the industry.

If I was to try this again I would spend 1–2 months commenting on blogs, guest posting (I did manage two posts here and here, under the pseudonym of Dave Smith) and building relationships with influencers in the niche.

This would enable me to build my skills, awareness and relationships to a place that would facilitate faster growth when I did start producing content.

Lesson learned: Don’t try to build an audience in a niche that you don’t know.

5. Highlife: Caracas

Building on lessons from all of the above, two good friends and I decided to provide accommodation, co-working space and transport for digital nomads looking for an exotic place to live, work and play in Venezuela.

We set up a WordPress theme, a Typeform application and social media profiles, and started reaching out to people we knew and people we didn’t.

We even received some unconventional PR on Twitter when our site was called out for being a “brotastic colonialist adventure program”:

Tweet screenshot

I had recently learnt from a master copywriter that if people are not slightly annoyed or offended by your website copy, you are too bland.

We received a number of applications (both fake and real), but are yet to close our first sale. Furthermore, we are unsure if we will be in Venezuela to deliver the program, so will most likely have to refund our customers regardless.

Key lesson: Again – be willing to deliver!


There we have it: Five of my greatest “fails” in five previous online businesses.

However, before I leave you in the glow of satisfaction that you haven’t made so many or such stupid mistakes, there is one more point we need to address.

You will note in each of the businesses above that there were some real positive takeaways:

Which leads us to the question: were these really “failures”?

I suppose that would depend on your definition of the term:

Failure is the state or condition of not meeting a desirable or intended objective, and may be viewed as the opposite of success.

If the definition of the “failure” of a business would be to not meet an objective within a certain time frame then yes, we have five “failures”. But if we were to expand that timeframe over a greater number of years, or even a whole life…we may come to a different conclusion.

As now, I am rolling up all of the experience listed above and beyond into a new project that is about to launch. Will that be a “failure”? We’ll see.

Do you have any tales of failure or lessons learned? Let us know in the comments section below!

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16 Responses to “5 Lessons From 5 Failed Online Business (That You Could Be Making Too)”

  1. Akosua Albritton
    January 26, 2016 at 7:23 pm

    It seems this writer missing core biz desires in all 5 situations. Maybe he ought to look into a franchise that he really wants to do or focus on writing and how make money online or off. That is his passion.

    • Tom
      January 28, 2016 at 2:07 pm

      Thanks for feedback Akosua!

      Yes I definitely see your point here and that I lacked core passion in each of these projects and think that the reason I will succeed in my currently one will because I am now more passionate about helping my customer/clients 🙂

      What is it that you do?


  2. Bob Valcourt
    January 26, 2016 at 11:05 pm

    Thanks for the eye opening post Tom,
    I am guilty of failure #1 as well, maybe not to that extent but still….

    I don’t see them as “failures” but as learning opportunities.

    Most people will never even try anything and laugh at you for failing.

    I have learned more in the last 6 months about making money and business in general than I have in the 20 years before that.

    I like you will keep trying until something works. I commend you on your persistence.

    • Tom
      January 28, 2016 at 2:08 pm

      Thanks Bob!

      Really appreciate the feedback and TOTALLY agree with failure Vs learning experience.

      What are you currently learning about?


  3. Kim Mason
    January 27, 2016 at 8:11 am

    Thanks Tom – an entertaining and educational post – thoroughly impressed by the speed and drive behind your various ventures….

    I provide advice to SMEs on business development on my blog, so that people can learn enough that they never need to hire a consultant like me.

    One of my most popular articles to date (and my absolute favourite to write) was “my top ten new business mistakes – I made them so you don’t have to.”!

    Thanks again for sharing yours,
    All things new biz

  4. Tom
    January 28, 2016 at 2:09 pm

    Hey Kim!

    Thanks for feedback, can you link me to your post?


  5. Elvis Michael
    January 30, 2016 at 9:03 pm

    Thanks for sharing, Tom.
    It seems that you were guilty (to some degree, at least) of jumping from one thing to another a tad quickly. And trust me, i am the all-time master of this stuff. And it really sucks.

    I did love your Tinder idea. And considering the one or two sales you made, i can see the potential there (especially now with other Tinder competitors). Would you ever reconsider jumping into any of these again, perhaps now that you are MUCH more experienced? 🙂

    Anyway, i love your creativity. Sadly, a creative mind can be our worst enemy considering we only have 24hrs in a day.

    Keep fighting the good fight!

    • Tom
      February 2, 2016 at 2:16 pm

      Hey Elvis!

      It seems we are kindred spirits 🙂

      I definitely succumb to the “grass is greener” mindset as you pointed out, but think I am starting to control that now.

      Which is why I would hesitate before taking on any new projects e.g. res-starting the Tinder biz, but defiantly think there is potential that is only rising with the prevalence of online dating, you want to take that idea on? 😉


      • Elvis Michael
        February 14, 2016 at 7:37 pm

        Haha, I would love to take on that idea — but as you said, I gotta have some self-control on my end, too!

        I recently purchased Todoist Premium (a to-do list pap) and the first thing I did was fill it with a very tight, almost unrealistic task list. After it had me working almost every hour of the day, thats when I opened my eyes and admitted to myself that I was trying to do too much. So I have scaled back a bit, despite still “itching” to resume some projects. They’re simply gonna have to wait.

        Needless to say, keep us posted about your successes; you’re always an inspiration, bud.


  6. Venkatesh Khajjidoni
    January 31, 2016 at 12:57 pm

    Hi Tom,

    Awesome post. There are many lessons to learn from your “trials”(I don’t call them failures) of many businesses.

    Your story is reminding me again and again that first I should give what my audience want — quality content.

    Thanks for great article.

    • Tom
      February 2, 2016 at 2:17 pm

      Hey Ventakesh!

      Yes totally agree with not calling them “failures” (does “failure” even exist?)

      For sure, a profitable business starts and ends with giving people what they want and NOT doing what you want.

      Thanks for taking the time to read/comment 🙂

  7. Dane Hinson
    February 3, 2016 at 10:02 pm

    Tom, love hearing the failures. If you don’t “fail” you’re not moving forward. I think the lessons learned are what propelled you to where you are today. Thanks for sharing!

  8. Alvin Wolff
    February 22, 2016 at 3:39 am


    Would you say that buying websites on Flippa is a good idea? I have been told about this but always assumed you don’t really know what you are getting into.

    Obviously, you explained your experience this one time, but do you have any other experience with Flippa?


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