My startup failed - here's what I learned...

Well ladies and gentlemen, it's time for the annual "my startup failed - here's what I learned" blogpost!

Before I begin I do want to acknowledge to myself that despite the outcome, I sacrificed a lot for this startup - my life savings, my relationship at the time, my income, I went to live at home in Johannesburg after living in a beautiful apartment in Cape Town, and then I moved to frikken Oklahoma! (no offence guys) I remember when I first got to America I literally had zero money and my best mate in LA had to order me groceries on his Instacart account. What I'm saying is, I gave her a lot of myself. But that was also the problem. I gave her too much, and eventually, she burned me the f*ck out.

But after processing the last few years of this experience while I spend some time in solitude in the idyllic English countryside - I realise it all played out the way it was meant to. I truly believe that, and I'm not using God or "everything happens for a reason", as a comforting, rationalisation strategy. I have processed it very well and I have come to understand on a much deeper level, that what I was after, and why I went after it in the first place - was not in line with who I authentically am or what my purpose is. But enough about me.

So ironically, our product's biggest flaw was that it did exactly what it was intended to do - expose issues within a team that weren't spoken about or identified, and then nudge team leaders to address them (with actionable tips). The real flaw however was my naivety. I didn't realise (or want to admit) that most managers didn't actually want to know about the problems in their teams. And once they did surface, they wanted to bury it. I once had a manager email me saying "Turn this thing off!!". Clearly giving his team a platform to raise issues anonymously was of great threat to his job.?

So I think my failure to recognise why (or where) we weren't getting mass adoption and pivot fast enough is what I'd say is the core reason why we failed. Of course, that is in addition to the many other classic first-time (tech) founder mistakes like; overly optimistic financial planning, impulsive hiring, corporate partnering too early, raising too little money, and not delegating enough. I mean initially, I was trying to bootstrap while creating a new category which is like trying to make an announcement at JFK with a toilet paper roll.

I used to mentor young entrepreneurs in South Africa, but what's funny is that on my journey, I never took my advice. I never followed the two books I used to swear by (The Four Steps to the Epiphany, and Crossing the Chasm). I guess it's just one of those life truths that ultimately - we have to learn through our own mistakes. After all, I failed to pivot fast enough and to niche small enough.

I do want to state that the startup didn't fail due to my (then addiction) or mental health. Sure, they may have contributed to the speed and efficiency of things, especially seeing as the last 18 months I was running on burned-out oil and pretty much hated my job. But one of the things that I learned from my first investor is that you can't blame anyone else for your business outcomes - every decision comes back to the founder and he or she alone is accountable for their business no matter what. That’s not to say that you should just blame yourself for every decision, no matter how dumb it seems, because a) there's absolutely no utility in blaming and shaming yourself, and b) it's all valuable lessons learned which will contribute to your overall success.

The good news is, I've found it really easy thus far to pursue new business ventures, because a) they haven’t been tech startups which are, well...bloody hard, and b) my fear of failure has drastically diminished. I now understand that business is a game. Except characters don't really die, you can always hit the restart button. I realised this whole capitalism thing really is just a game and whoever has the bigger ego generally wins. That's not a stab at capitalism and the free market system, I just don’t think most players in the game realise that they're the ones actually being played. I'm really grateful to have been away from it and had the opportunity to return to my artistic roots these past few months. I digress.

“We must be willing to let go of the life we planned so as to have the life that is waiting for us.'” Joseph Campbell

Here are some of the key learnings I came to understand the hard way:

1. It's all about who you work with - life’s too short to work with assholes.

• Do in-depth background checks - don't apologise for them - if people don't want to go through them that's a red flag itself.
• Get objectivity - your judgement can sometimes be blurred by what impresses you about that person.
• Make sure the people you’ll work very closely with, are people you'd actually want to hang out with.
• Test by results/outcomes not resume/CV - they mean absolutely f*ckall - Always do a trial.

2. Make sure work is fun - you can still enjoy it even if it’s your company!

• Have fun along the journey, after all you may die before the destination!
• Invest more heavily than you think in team-building, social activities etc
• Don't take it all too seriously (remember, it's all just a simulation??)
• Delegate as much of the boring stuff as possible! Strengths-based working.

This was a big one for me that contributed to my burnout. Being naturally a resourceful person I would force myself to learn to do the things I was bad at (and even hated) just because I was under the impression that the founder has to do everything in the beginning, and startups are hard, and just get on with it mate.

3. Find partners and investors who make you comfortable

• You want to be able to feel comfortable to be fully transparent with your backers/partners and if they are always trying to screw you, well what kind of backers are those to begin with.
• Oh and master expectation management, from setting them to managing them (with your team, investors, customers, and yourself!)
• Be transparent instead of holding all the stress to yourself (share the load - and if your partner doesn't share - they're not a true partner)

Last but not least - TAKE CARE OF YOURSELF! Healthy CEO = Healthy Company. I neglected myself for far too long and it really had a bad impact on my mental health and fueled my addictions. It's a lonely journey (even if you're not a solo founder), so make sure to have a strong support system in place, and nurture your relationships -? you'll need them more than ever.

Pro-Tip: Be careful not to build your sense of self around your startup - that way your emotional clock, and your self-esteem is not subject to what happens in your startup which mostly is beyond your control. It's a business, not a bloody limb.

I was truly blessed to have a few enlightened and supportive people around me toward the end that helped me to prepare and accept the outcome with as much equanimity, humility, and gratitude as possible. And I am forever grateful to them for that.

I'll end with this nugget of positivity - Someone told me this recently which never even occurred to me -? despite the startup failing, throughout its existence it never failed to provide many things to many people, like jobs, learning opportunities and experiences, and those skills and lessons will spread into other areas and other projects going forward. I liked that. I'd add that we also contributed to the positive narrative on employee experience and team performance through our blogs, webinars and conversations. Hopefully, some of that impact was felt by some employees somewhere.

I want to thank all of those who contributed to my vision over the years, not going to name everyone but you know who you are, and you are appreciated.

Au Revoir until the next one, and don't take life too seriously, or it will take you (seriously).

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Also loved this article by Wil Schroter ?: https://www.startups.com/library/expert-advice/emotional-cost-startup-founder