The life of a founder is never dull. It constantly feels like you’re only one call away from greatness and potential failure at the same time.
But comfort can breed complacency right?
We’re nearing our eight birthday at PledgeMe. And believe me, I feel every one of those years older.
But it’s got me thinking about what I wish I had known from the outset.
Would any of this knowledge have got me here quicker?
To be honest, I’m not sure. As with a lot in the startup world, you just need to learn by doing.
But in the hope it may help other founders make some different mistakes in their own struggle down startup street, here are five lessons I’ve learnt along the way.
1. Know why you’re doing this
From the moment I transferred $5,000 into a business account, I’ve had doubts. Every founder does, constantly focusing on the opportunities and the risks they need to mitigate. Those that say different are probably missing the risk awareness gene and will probably turn out to be cowboys.
I never wanted a corporate, turn-up-at-9am,
I wanted to make a positive difference in the world. And for that, I needed to feel like I was in control of some of my own decisions. Not have them dictated to me. And part of that is making sure I felt the work I was doing had a bigger purpose than moving numbers around a spreadsheet.
I wish I’d taken comfort in moments of doubt around whether my decisions were right or wrong, realising that life is about the journey rather than having to get to an endpoint.
I’m not saying you shouldn’t have goals to guide you, but take the time to look back on the mountain you’ve already climbed. And remember why you’re climbing it in the first place.
Not everything you do will work, but how you handle those moments of doubt will help define you.
2. Don’t work with dickheads
This is a big one. Please. If you have even the slightest inkling that a person you’re going to start working with is a douche, turn back. Don’t engage.
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Life is too short to work with people you don’t like.
Let me repeat: life is too short.
If they yell at you, get out.
If they treat you like a little girl, get out.
If their emails come into your inbox and you don’t want to open them because you’re scared of what they’ll say, get out.
If they think they’re the smartest person in the room, get out.
If you feel bad when you’re around them, get the hell out.
You don’t have to be friends with everyone, and you definitely don’t need to work with everyone.
3. Document expectations
I love writing, despite not always being the most responsive on email. And through pained experiences, I’ve turned this power to communicate into a process of documenting relationship expectations.
Most new relationships in business start off great (otherwise they wouldn’t begin). But, even the greatest starts can lead to the lowest lows if you don’t understand what you’re getting into.
It’s human nature that we each interact and interpret nuances differently. I’m not saying people you converse with will intentionally disregard what you’ve said, but each of us brings our own baggage from previous experiences, which affects our comprehension of a situation. Often, a lot is left unsaid that should be discussed.
So my advice is to adopt a rule of writing expectations down and sharing them.
New shareholder? Get the shareholders agreement out.
New team member? Draft up a job description and contract.
New board member? Outline the terms.
If it needs to be legally binding, get a lawyer to check it (and, if the agreement is with a lawyer, don’t let them draft it).
Document everything, and trust your gut.
4. Ask questions
This follows on from the last point, but please for the love of everything good ask more questions. You might be worried about looking stupid, but I bet half the people in a room have the same unsaid query 95% of the time. (Side point: question people on their sources!)
You might think ‘I’ll Google that later’, but you never will. People love to talk, especially if it makes them look knowledgeable. It displays a level of engagement. So hopefully, asking questions can smoke out those that want to help you and those who don’t.
People in our space can be super supportive, and even more willing to share when you do too. So get out there and ask people how they approach their business — even the most senior execs will be willing to help.
5. Surround yourself with those who care about you
This starts with being yourself. You are your best asset. You can get a long way by having confidence in what you know and asking about that which you don’t. Then, complement your skills by surrounding yourself with a great team — those that feel invested in your ultimate success.
Same goes for your friends.
Starting up is hard. Staying up is even harder. So look for those who will be your cheerleader in the good times and a confidant when you stumble. Going it alone can often lead to a breaking point.
We’re social creatures so when you get an invite, say yes, and leave that spreadsheet for another day.
And one last bonus tip: don’t compare your insides with others’ outsides.
You will never truly know what’s going on in someone’s life, so focus on what you have control over and can improve.