My Top 3 List of Infamous Personal Business Flops and Failures

It’s not easy to turn an idea into a business that makes money. In my list of business flops and failures below, I share some of the ideas I’ve had over the years that never turned into anything, and the learning lessons I took from them. If you’re a tech industry entrepreneur, I hope you can take something from them!

Also, if you’ve never written down your own failures and learning lessons, you might not be fully bedding down the learning lessons you can benefit from in future enterprises, so why not do it now?

electronic forms automation (image)

1990 – Electronic Forms Automation

Back at the turn of the century, Gartner was projecting that Electronic Forms was going to become a huge market. At the time, I was in the printer hardware industry and the Magic Quadrant report convinced me that it was worth investing in. Certainly, the notion of moving to electronic forms from hard-copy forms printing made sense to me from my stand-point in the printer hardware industry. While the Electronic Forms industry did grow a little over the next few years, the pace of adoption was by no means at the scale Gartner projected.

What did I learn from this?

Industry reports are useful and helpful, but you shouldn’t use them as the only source of your decisioning. It’s always better to speak with your target audience–the people who directly influence the buying decisions–and make sure they are ‘ready’ to make the move to a new way of working.

The consequences?

That Gartner report convinced me to move industry. As it happened, the change of direction in my case opened my eyes to new problems and challenges, so it wasn’t such a bad impact. Furthermore, I’ve never relied on industry reports ever since.

enterprise mashups (image)
enterprise mashups (image)

2003 – ‘Jigsaw’ Enterprise Mashups

This was my first attempt with the team behind ‘ENCANVAS‘ to create a No-Code tool-kit to create enterprise apps that could harvest data from across the enterprise. Yet again, Gartner projected a huge spike in demand. This time, I was more skeptical of the industry analysis. Indeed, when I spoke to the target audience there was definitely ‘a problem’ using traditional tools to create apps that senior managers needed to turn strategic plans into actionable operational improvements supported by IT.

We went ahead and created the first version of ‘ENCANVAS‘ (then called ‘Jigsaw’) and we were soon winning awards. What we hadn’t counted on was the resistance from IT leaders to trying something new that changed THE WAY they worked.

What did I learn from this?

Fear of change is an enormous de-motivator for enterprise decision makers. Most are less concerned with progressing their business forward, and more concerned with their departmental performance and the outcomes they are specifically measured on. Some personalities genuinely don’t care about the ‘big picture’–even when they are part of the management team. If your business idea requires ‘change’ in attitudes and methods (not just technology and instruments), then you’d better make sure the rewards are compelling enough to overcome ‘change resistance’ objections.

The consequences?

The Enterprise Mashups market turned out to be a flop. It spawned over twenty businesses–even big names like Microsoft and Google who tried their hand–that all either disappeared over the next two years, or diversified as we did at ENCANVAS. there are only a few companies that survived this wrong steer–companies like OutlookSoft and that remained in the No-Code space, and others that transitioned to become leading RPA kernels, later acquired by companies including Kofax and Lexmark. On the plus side, the technical features required for Enterprise Mashup applications led our team to develop a complete suite of No-Code APIs that are now in high demand thanks to digital transformation and iPaaS demands.

enterprise collaboration and messaging (image)
enterprise collaboration and messaging (image)

2006 – Squork Messaging Platform (Email Alternative)

If you are ‘that old’ you will remember that Google came up with a hugely innovative product back in 2006 called Google Wave. It was the first real attempt by any major vendor to displace email with something better. In the case of Google Wave, users were able to send one another real-time messages to individuals and groups, facilitating a conversation that would progressively contain all of the contributions.

It was a forerunner to systems like Slack, WhatsApp, Facebook Messenger, etc. Having seen the concept, I became convinced the development team at ENCANVAS could produce a solution that was simpler and less graphically rich (reducing loadings on enterprise infrastructure). What came out of it was ‘Squork‘ which, were you to take a read of the design brief, was basically WhatsApp. Unfortunately, we never had the funding to take the solution to market, as ENCANVAS was taking priority on our development resources. Consequently, Squork was never to reach its market. This is all the more galling when WhatsApp didn’t even start until 2009 and the guys there sold their business to Facebook for $4 billion in cash, $12 billion in Facebook shares, and an additional $3 billion in restricted stock units 

What did I learn from this?

I learned a lot from Squork. Firstly, if you really are committed to a business idea, don’t try to push the elephant up hill by yourself. Sometimes, it makes sense to reach out for funding to give yourself a platform for success. Secondly, no matter how good an idea might be, no entrepreneur should consider doing more than one initiative at the same time. Time is too precious to split it down the middle.

The consequences?

By trying to develop Squork at the same time as ENCANVAS, not only did we not bring the product to market, but it also slowed the time to market of the second generation ENCANVAS platform, in an industry when time to market is everything. This had dire consequences for ENCANVAS (we weren’t able to fully leverage the technology for another few years) and I never made $3 billion either!


I guess my biggest take-away is to recognise that inevitably failures do happen when you’re on the bleeding edge of innovation. Every creative process is a blend of successes and failures. When you learn from them, it doesn’t feel quite so bad. Additionally, I’ve found every failure has motivated me to learn a different discipline, industry or method that has ultimately added to my career.

So don’t fear failure, but make sure you write down the learning lessons objectively–and try not to do it again!

Ian Tomlin Pic

Ian Tomlin

CEO Newton Day

Ian Tomlin is a business management consultant, having led a career as a CEO, marketer, tech innovator, and business writer. He founded and is CEO of the marketing and innovation company Newton Day where he helps businesses tell their product stories and make conversation with their customers. His writing includes fourteen titles including the 60-Minute Expert series of ultimate ‘how-to’ guides for practitioners. Follow him on LinkedIn or Twitter.