From Lobster to Loner - leaving Google to start a business

So much has been written about how to start a business, sell a business and all the steps in between. Little has been written about what the first few months are like after you’ve made the leap. A period of time where you don’t know what you’re doing, live in a constant loop of anxiety, joy, despair and excitement, and have to quickly become comfortable with being deeply uncomfortable.

Building a business is hard but it’s incredible fun. Below are seven learnings from the last five months. This is not an attempt to glorify the “struggle”. I wrote this to provide a candid perspective on my experience of going “all in”. Hopefully there’s something useful here for others undertaking or considering undertaking similar journeys.

Just get doing

If you removed 50% of white collar jobs from most companies you wouldn’t see any material change in performance. Not true when starting out. When you’re sick, tired and behind on sleep, you keep going. You have no choice. You realtime live the relationship of energy input to momentum output. It’s on you to make things happen and keep moving.

Take care of base

Your default operating state in the first few months of starting a business is frazzled. Your to-do list is a hydra, you’re having to quickly up skill on a number of topics where your base knowledge is low, you are working harder than you ever have before, and you have little cognitive capacity for anything outside of work. Most likely, you will be a poorer version of yourself to the people that matter the most.

During this phase, your quality of life and mental toll are so closely correlated with the support of the people you’re closest to. This is a team journey you go on together. They ride the highs, support you through the lows and are the anchor that keeps you sane. Recognise the sacrifices and tradeoffs partners make to enable you to do what you do.  Most entrepreneurs wouldn’t exist without them.

Your core friends are also so important. You need people who’ve known you for a long time and don’t care what you’re doing for work. People who can pull you out of your head and make you remember there is a big old world out there.  Cherish your support network, it’s so much harder without them.

Be unreasonable with how you value your time

I’ve always been obsessive with how I manage and prioritise my time but the last five months have forced this to a new level. Most weeks I’ll plot out everything I need to do, time block it in my calendar and quickly realise there aren’t enough hours in the week. It’s not romantic to cordon off time in your calendar to spend with your wife but if you don’t, work will find a way of creeping in. You have to learn to be focussed, place a premium on routine and structure, and block time for the things you really value. This is, and I imagine will always be, a constant work in progress. Balance is elusive.

Existential dread is a constant companion, that’s ok

This is personality specific and will vary depending on your business model, life situation and level of risk. For me, it’s been a challenge. I have a mortgage and wife who’s about to have a baby - there were plenty of reasons to stay at Google.

My mind is always on, I’m constantly thinking about how to get the best out of our team, the quality of work we’re doing for our customers, our finances, technology risk, and what we need to do to move faster. I was never a good sleeper and this has definitely become worse. I can’t say I have a good solution but I’ve become much better at recognising where the little demon on my shoulder comes from and being comfortable with it. The usual stuff helps: exercise, diet, a good night’s sleep, reading novels before going to sleep. Oh, and being really clear on why you left in the first place.

Write down your push and pull factors and stick them on your wall

One of the best pieces of practical advice I’ve received was to write down a list of all the push factors that made you want to leave your job and all the pull factors that made you want to start a new one. This is your ‘why’ and it’s powerful. If I’m working late at night doing something unglamorous and feeling flat, I just have to look up and am quickly reminded that there isn’t anywhere else I’d rather be. I’d also recommend sharing them with your business partner/s as you’ll get a much deeper understanding of how you both think and can better support each other when you go through the inevitable lows.

Choose your work wives wisely

There is so much literature on choosing co-founders and building strong relationships that I haven’t got anything novel to add to the discourse other than to say, take this seriously, it’s so important. Starting a business is a lonely undertaking and you need great people who you trust deeply by your side. I’m incredibly lucky on this front.

Small gestures are powerful

The little things mean a hell of a lot. Food packages from my aunt, parents in law coming over and cooking dinner, friends dropping in unannounced and taking me for a walk. To be honest, I think a lot of these were done for my wife’s sanity as much as my own but my god they made a difference. It takes a village to build a company.