On leadership and startups when you don’t fit the mould

In the spirit of International women’s day, here are a few things learned so far on leadership and running a tech business. I hope it helps anyone that feels out of place with the knowledge there are others like you quietly plugging away.

1. The broader tech startup industry is fuelled on smoke, mirrors and BS that makes Nathan Barley sketches seem tame. Having a slick pitch and a vision will impress your startup friends and family only. Keep your AI, Blockchain, IoT buzzword bingo and fantasies of how you will disrupt the giants to yourself. Humbly work out why anyone should even spend 30 seconds using your thing.

2. Top skills underrated in leaders are empathy and the ability to keep their mouth shut and observe. Be present to problems people are facing, it will help you build amazing products as well as be a better manager.

3. It’s ok to refuse to play i.e. to gas about how you are crushing it or run towards every conference stage and startup competition. Instead work out how to be straightforward to do business with and easy to buy from.

4. Don’t compare yourself to others who seem to be doing it for less time than you or have raised more money. Shout out to the Benjamin Button startups that were registered 10 yrs ago but claim a founding date 5–8 years later, I see you but am not mad. It really does take a lot of time.

5. It’s hard to run a business. You think about it 24hrs a day and the grind phase is at least 10–15 years. There will be at least once a week where you wonder why you are even doing this. Do you know more than you did a month ago? Do you have more revenue? Acknowledge it.

6. It’s completely doable without sitting at a desk 14 hrs per day. It is totally doable if you have children. It’s your party; you can set up remote teams if you want, finish early to do the school run without worrying about what a boss will say. There are a lot of women in the world with children working much much much harder than me and without a small % of the autonomy I enjoy.

7. Lead by example. Don’t expect your team to pay attention to the details if you don’t, don’t expect your team to be transparent if you aren’t.

8. Raise or don’t raise money there is no right way. Do stop reading the VC pro /con blog posts. The whole thing is so steeped in privilege and survivor bias to be utterly useless. Side eye people that have really strong opinions on how others finance their companies.

Yes, it is likely that a Stanford dropout white dude will walk in/out with millions of funding with less merit than you, the numbers tell us this is reality in 2018. I personally prefer to spend my mental energy on things I have control over and accept the chips will fall where they may.

9. Understand the stats and be mindful of the probabilities, allocate your time and energy accordingly. I calculate that each customer meeting I take will have a 10–20% of success but a VC meeting will have a 0.1% or less. I allocate my time mostly to the things with a higher likelihood of success. The wonderful VCs I know get why this is necessary and the ones that get petulant get the side eye.

10. Addition to 9 to maximise your chances of success, work harder to win over firms that have a track record of funding other people like you or (even better) those that have senior partners that look like you. Life is much easier when you aren’t the first.

11. Just because something has a low chance of success, it doesn’t mean you don’t do the prep work and bring excellence. Bring everything or don’t do it at all.

12. Study companies that have got far with very little money and intimately understand what they got right. It will give you discipline when (never an if) times are tough.

13. Have a plan if you raise, don’t raise, under raise. Stress test the shit out of the worse case scenarios. Know exactly on what dates contingency measures will get triggered and update probabilities weekly based on facts. Chop off happy ears and cultivate scepticism. People are polite but hardly anyone will tell you that your baby is ugly or that they just don’t get it. With planned contingencies, you will sleep soundly and can concentrate on being present at on the day to day work.

14. Find customers as quickly as humanly possible, from day 1. Then pour blood, sweat and tears into keeping them happy.

15. Have fun :) I still have to pinch myself every day that people pay for a thing I built.

  • * Am still learning and reserve the right to change.
  • ** ymmv
  • *** yyy I know not all X