I didn’t come from an entrepreneurial family. My dad is a journalist and my mum a nurse, and while they have an absurdly good work ethic, business people they are not (and they’d be more than happy to tell you that). I went to a grammar school where success was thought of in a very linear way; do well in your A-levels, get a degree, and work your way up the career ladder. As with most schools, we weren’t taught about business enterprise, and I didn’t really know people who owned businesses or were that-way-wired. All I believed, was that getting A*s and As was the secret to a happy and successful life. And as many people who've been to a grammar school will attest, the environment brings incredible academic opportunity, but fear of failure looms large.
I didn’t really see my own background in any of the business founder stories I had heard either; people who’d come from a council estate and made it (think Joe Wicks), and people who’d knuckled down with the benefit of financial support and parental mentorship (Jamie Laing). Both inspirational in their own way (listen to Elizabeth Day’s How to Fail Podcast with Jamie Laing if you’re undecided on the latter — you will fall in LOVE), and both — essentially — with nothing to lose. And I felt like I did; a reasonably good academic record, access to an overdraft and… well… face.
I still don’t really think of myself as an entrepreneur (the word sounds kind of Del Boy to me anyway!), and I definitely don’t feel like business is something that comes naturally to me. But I have realised that it’s not just something that you’re born with. It’s something you can learn.
When I finally decided to set out on my dream business journey — still laden with anxiety and the fear of falling arse-over-tit, I read and listened to as many books and podcasts about business that I could get my hands on. I had an hour’s drive to work every day, and I would listen to memoirs, business guides and stories of people who’d made it when every single circumstance they encountered along the way suggested that they shouldn’t.
If you’re thinking of embarking on a similar journey, here are some of the books I recommend first:
You are a Bad Ass by Jen Sincero
The title of this book is definitely one that will make you feel like a bit of a nob if you read it on the train. But — along with The Secret — it is widely regarded as one of the definitive guides to the art of manifestation.
I am usually a bit eye-rolly about manifestation coaches; people who essentially say “I never made any money until I learnt about manifestation and became a coach who asks people for money to teach them about manifestation… pay me and I’ll tell you more!” And I am usually hugely cynical about anything a bit "woo-woo”. But it has been impossible to ignore the impact of these teachings in my own life and business since I started implementing them.
In a nutshell, it’s about having complete, unwavering faith and belief in your life or business plan, even when everything seems to be telling you that you’re on the wrong path. It’s about shouting “Is that the best you can do?” when the universe throws you a massive f*cking curveball. It’s about believing the impossible when logic seems to tell you otherwise.
For the cynics, there is still a lot In Sincero’s book that makes sense; essentially that making a plan and keeping a positive attitude will get you far (it’s not rocket science). For the more spiritually-minded, there’s the concept of literally inviting things into your life (like Caitlyn Jenner suddenly being introduced to me out of nowhere, a week after launch, and two weeks after I’d written her name down on a list of women I’d like to see in my shoes. My cynicism has taken a beating over the course of my business journey, to be fair).
Eat, Drink, Run by Bryony Gordon
Bryony probably didn’t intend to write a business guide, but this particular memoir really resonated with me when I started Otto + Ivy. As a chronic anxiety sufferer who frequently feels like a bit of a fraud, Gordon’s venture into marathon running, when she is — by her own reckoning — not someone who fits the typical athlete mould, definitely struck a chord. I had ventured into an industry that I hadn’t previously worked in, and the odd ‘expert’ made me feel like I had no business being there. But if she can run 26 miles, then how hard can it be to makes shoes that fit? (Very hard actually, but you get the idea).
Do what you love, Love what you do by Holly Tucker
It’s surprising how few business guides are written by people who actually have product business or start-up experience. Most seem to be written by life coaches, who offer wise words but very little in the way of practical advice. Holly’s book is the absolute antithesis of this, and is essential reading for anyone hoping to create a business with soul. For those who don’t follow Holly — the founder of Not on the Highstreet, and the UK ambassador for small businesses — she is the multi-coloured-kaftan-wearing guru of start-ups. I’ve listened to almost every single episode of her brilliant “Conversations of Inspiration” podcast, and it’s impossible not to be carried along on her wave of enthusiasm.
Shoe Dog by Phil Knight
This is a compulsive and sometimes dramatic read by the founder of Nike, who started selling shoes from the boot of his car and now owns a multi-billion dollar company. He recalls the intense rivalry with Adidas, dealing with manufacturers of fraudulent Nikes, and creating the initial sneaker sole with a waffle maker. I mostly listened to the audio version, which solved the age-old argument with my husband about how to pronounce Nike (he still pronounces it like it rhymes with bike, but perhaps there’s no teaching some people after all).
Other books I recommend include Losing my Virginity by Branson (a tale of basically winging it, and the entrepreneur's bible). The Obstacle is the Way by Ryan Holiday (you will need this when the sh*t hits the fan... and I've come to realise that there honestly is truth in that title). She means Business by Carrie Green; a particular takeaway being that you shouldn't listen to every single piece of advice you're given, as some opinions can be crushing AND untrue.
I am still learning, falling, making big whacking mistakes, and never has the old duck-above-water analogy been so apt. But I seem to bounce back quicker from every dilemma than I ever did at the start. And I honestly believe that if you love what you do — and you enjoy the process — then nothing can possibly be wasted. (I don't think I made that up. I think it was Oprah).