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The Mental Rollercoaster of Startups

Remy Sharp

Benjamin Southworth

April 29, 2019

I can’t remember all the startup ideas I’ve spun up. But I can always remember the emotional roller-coaster that goes with it. Whether it’s a week long sprint, or a seven year marathon.

So far I’ve only brought one idea fully to completion of the journey, with an exit to Tiny Capital in 2017. You’d have thought that would have me happy, I can’t talk to the other founders, but it set off a huge bunch of hard questions that have occupied my thoughts for at least a year or more.

Since I was 16 I’ve suffered from depression and anxiety. This manifests itself in many ways but for me it has matured ( or perhaps I have ) in to a ceaseless self criticism, I’ve learned to turned this in to a tool to get things done. The desire to silence the beast has pushed me to do more than I imagined, but it is not a healthy relationship, but one I need to repair before too long.

But I’d sold my company right? I’d won? The beast was slain right? I’d ticked off another bucket list thing off, and before I was 40!

Nope. Not a bit of it. The money came and healed the financial bruises I’d acquired, and let me get set back up in London and up my lifestyle quality.

After a while back in London, The beast reappeared. 3 Beards, my heart and soul for the last 7 years had closed, Unicorn Hunt was loved and had done okay, but I’d broken myself against it over the last two years, and now, back in London, a success by even my own measures, I was distraught. Who the hell even was I anymore?

As founders, I - somewhat simply - think we’re either artists or criminals ( PG talks far better about this in Hackers & Painters ) and I’m on the artist side. As such these projects are my babies, they occupy the majority of my thoughts. I sketch logo’s on napkins, I have notebooks crammed with thinking and doodles, domain names piled high, and a thousand questions I want answers to. I love it in the way of discovering a song on the guitar, or trying to paint a portrait. It’s the act of uncovering something beautiful and learning new skills and knowledge along the way.

This, however, can leave you at the caprice and mercy of your projects, we have great days and bad days, we go from loss and rejection to huge wins and successes and for even for those who are without mental health issues going in, you’re unlikely to walk out of this industry without a few mental bruises or close hand experience of it.

Everyone needs to understand their own mind, it’s weather patterns, and it's warning signs.

Here’s my top tips; your mileage may vary.

  1. Work hard, but get enough sleep.

  2. Have fun, but don’t let play interrupt work too often.

  3. Don’t let the negative voices internally stop you, you’ll hear enough externally. Have faith.


  4. Know your business inside out, upside down and back to front. Know what you don’t know and plan for what you do. Uncertainty can breed anxiety.


  5. Get away from the screen(s), walking and thinking is better than tweeting and researching without aim.


  6. Write, sketch, model, map, summaries, expand, discuss & reflect.

  7. Ask for help, people want to support you.

If you ever want a coffee, or a drink to talk about your own mental health as a founder, then please drop me an email, I'd be happy to listen.

Why not tweet me your own suggestions, resources, tips etc and I'll keep updating this post with the best tips.

Benjamin