No one wants to talk about their failures, yet it’s the most important way to learn and improve. Learning through doing is more about making mistakes as it is about repetition. The key is to look back and review: the post-mortem.

It’s a part of the startup game and it’s important to know that in the world of startups, failure is the norm - not the exception. When you join a startup it’s important to acknowledge that you’re going to be out of your comfort zone.

In mid-2006, I joined what would become a failed startup venture. We officially dissolved the company in mid-2012, however in reality it had failed far earlier. I’d like to share some of my views on the experience.

TL;DR version? Click here.

In the Beginning

Three friends and former colleagues of mine approached me with an idea in the photo management software and online sharing space. They viewed the market as fragmented and poorly served, particularly in the ‘full-stack photo solution’. I generally agreed; we became the founders of Tecagora and created the product Snapact.

Our team and share structure:

  • Business guy (28%): accounting, legal, sales/business development
  • Business/Technology guy (24%): operating and some product management/development
  • Technology dude (24%): Windows software development
  • Technology dude (me, 24%): some Windows software dev but mostly server side web app development

We had no share/option vesting schedules or cliffs - just straight up percentage ownership. We bootstrapped the business and kept separate full-time jobs elsewhere. Naturally, evenings and weekends were meant for ‘starting up’.

The product was photo management software for Windows tightly coupled to a web app for online photo sharing - and we were excited to bring this vision to life.

The Long Road

We made some early assumptions on how we’d generate revenue, based on our collective prior experiences at other companies. Instead, we made the easy decision to focus on building the product right off the bat with little regard to monetization.

It was also decided that adding features before launching was critical. It was important to us to have a product that did more than a minimal feature set. This left us with a really long roadmap to get anything to market. In short, our overall plan was: build it and they will come.

To be clear, our initial product vision wasn’t as feature-rich as the entrenched competition. However, we definitely should have simplified our initial product’s feature set further to get to market quicker.

I don’t remember exactly how long it took to get to launch day, but we were excited when we opened the doors to the public. We labeled Snapact ‘beta’ because it was the cool thing to do at the time with your new tech baby.

Both the software and the online photo sharing portal were free at launch; we uploaded the software on various free/shareware portals for distribution.

I seem to remember we decided to make the photo sharing service freemium: share up to 100 photos (or something like that), after that you’d need to upgrade. The photo manager client software remained free.

We also briefly talked about looking for funding, but quickly decided we didn’t want to dilute our shares - besides, what could funding bring (if we could even get it) that we needed?

Reality Hits

We had several thousand downloads over the lifetime of the product - notably, this isn’t a lot. Worse, we didn’t make it easy for users to give us feedback. This limited our ability to iterate and improve - we were reduced to guesses and assumptions. Never a good thing.

Some product reviews were written and published online - a few were surprises to us, most had been at our request/suggestion to pertinent sites. We managed to get placed on a software compilation disc distributed via a European non-english magazine.

Despite in-app prompting, few people were signing up for our online photo sharing service. You shouldn’t expect much from just a few software downloads/installs/users, when only a small fraction will sign up for a freemium service.

Eventually Google Adsense was added to shared photo pages. Revenue from this was - you guessed it - negligible. We tried working with 3rd party vendors to generate product sales - I don’t remember the specifics of this, but vendors quickly lost interest in pushing the distribution of Snapact. They’re commission-based and if people aren’t raving about the product it won’t generate sales - leaving them with little incentive.

I remember frustration, fear, anger and hopelessness at various points after the startup honeymoon and launch periods. While I truly enjoyed building the product, our team interaction began to feel strained. Remember, this was a bootstrapped company - it provided no income for any of us. It wasn’t even covering its own costs.

It began to feel like we allowed only consensus-driven decision-making, meaning we weren’t making critical decisions. We glossed over and tried to ignore important signals which, if we’d been attentive may have given us better direction.

Essentially, it felt aimless.

So Many Lessons: TL;DR

  1. Your expectations, no matter how realistic they seem - are actually wildly optimistic.
  2. Don’t be secretive about your idea. Sure it’s your baby, but before you pour money and time into it, do your best to invalidate it - get outside input.
  3. Don’t be wishy-washy. Make concrete decisions. No one should ever leave a discussion or meeting wondering what the outcome was or next steps are.
  4. Listen to your gut; recognize signals. Your subconscious is probably aware of various signals that you’re unwilling to see.
  5. Set goals and measure progress towards those goals. If a goal isn’t on track then it’s either too optimistic or you need to consider another path. The end result is the same - you need to adjust. Worst case should be a pivot.
  6. Don’t be afraid to walk away from a situation/startup/idea you’re not happy with. Move on to the next.
  7. Always be inventive/innovative/ideating. Look outside your group - how are other people achieving success? Can you apply that to your startup?
  8. Collaborate outside your startup team. Discussing methods, tools, ideas, etc with others can only create stronger output.
  9. Know how to grow a userbase. Maybe they won’t all succeed, but have an arsenal of strategies to deploy. This means researching, preparation and lead time.
  10. Talk to your cofounders. Don’t sweep concerns under the rug, air your dirty laundry. Deal with things rather than bottling them up.
  11. Right from the beginning, formulate your funnel. Acquisition, sales, retention - they’re all important elements to factor in.
  12. Advertising based revenue isn’t a foundation to build a business on. You need a massive monthly pageview count to make Adsense and the like work.
  13. If something goes wrong, use the 5 Whys to determine a course of action. Hell, if something goes right, use the 5 Whys to solidify what you should bake into your startup DNA.
  14. Don’t re-invent the wheel. Find a way to improve the wheel but make sure that people need your better wheel.
  15. Charge your users from the beginning. You avoid awkward moments later when you want to add payments in. Crucially, you also discover whether you have a revenue model and product worth pursuing. It also means that bootstrapping can be feasible.
  16. Consider getting funding. Just the act of trying to get funding will reveal a mountain of wishful thinking on your part. (I’m all for bootstrapping, but going for funding really is an eye-opening experience)
  17. Share/option vesting and cliffs aren’t a bad thing. It allows someone to walk away from the company without those who remain feeling ripped off. Everyone involved should feel protected.
  18. Realize that whatever your thoughts for your MVP (minimal viable product) are, it’s probably still too much. Trim some more fat, then launch. Then iterate based on feedback.
  19. Don’t bother with fancy C-level titles until well after there is someone to impress. I don’t mean users - investors and the like. Instead, you’re all founders trying to start something up. Keep the focus on that.
  20. If you’re excited about something, you’re not thinking rationally. Take some time and don’t rush in. You need to think it through.

Back to Today

I still look back at this startup with mixed emotions. I still remember that initial excitement and am still on the hunt for it again - but this time in a sustainable form. I learned an incredible amount from this failure, and for this I am grateful to my former cofounders.

Life has since changed for each of us, but I’m still friends with them. We’ve all moved on to other projects and jobs and we all still have the startup bug.

This retrospective is solely from my point of view, not representing the thoughts and opinions of my fellow co-founders. They likely view things differently.

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James is a Canadian living on Canada's west coast. Interested in tech, code, startups, and being awesome. Leading tech efforts at ChatterBlock, OneWed, and SeafoodX. Top-notch Dad, subjectively speaking.

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