Dream: We’ll get funding and a magical fairy will deposit paychecks for us and our employees in our bank accounts each week. And then give us really nice health insurance.
Reality: Setting this stuff up is the worst. THE WORST. There are always mistakes and you will learn more about state and federal taxes than you ever cared to.
Lesson: Ask other founders who they use, monitor every detail. If something feels like a mistake, it probably is one, and it’s your responsibility to fix it.
Staying in relationships
Dream: We’ve talked about how the fundraising process was like dating—in the worst possible way. And how hiring can be a series of very bad Match dates. But once we met our investor match and first hires we kinda sorta thought we were happily settled into relationship-ville. Not quite.
Reality: Keeping your current investors happy and your employees happy is a lot like being in the most insecure relationship ever. There’s always a little voice whispering — are things really OK? You want to show them how much you love them and that you know they love you, but secretly you’re always wondering if they’re cheating on you.
Lesson: Learn to focus on your team and keep them happy, challenged, motivated, and invested.
Hiring for jobs that bore you
Dream: We’ll get funding and a magical fairy will find us a bookkeeper, a contract lawyer, and an accountant
Reality: You have to interview people for these positions and find the right fit. To many, ‘startup’ budget means different things—especially when they hear you just took in money. Each type of role often believes theirs is the most important line item in your budget.
Lesson: Only go through referrals.
Dream: We’ll have a “Richie Rich” moment and drink a milkshake with our feet up.
Reality: We haven’t had one yet but every entrepreneur—from the new ones to those on Fortune 500 lists look like they have Stockholm Syndrome when they talk about theirs.
Lesson: We are continuously warned to “keep it casual for as long as we can”—we’ll keep you posted.
New Entrepreneur Lesson of the Day: Decide on your favorite brand of wine and stock up. Being a CEO is hard.