People make mistakes. New entrepreneurs make mistakes all f’ing day long. We’ve made a LOT…
Things we’ve done wrong:
Asked for too much
THE STORY: In the earliest of Skimm days, a very big brand wanted to work with us. The head of said brand was an idol of ours and we were very excited. They asked us to throw out a number of how much it would be to work together in a very big way. We asked people for advice and people told us to aim really high. We aimed a little too high.
THE REACTION: We got a bunch of emails telling us we should be ashamed of ourselves and that we had lost a potential mentor.
THE PANIC: We wrote 3 apology notes and sent flowers we couldn’t afford.
THE LESSON: We were wrong. But we also realized that a mentor should want to welcome the opportunity to teach us and put us in our place. Not just make us feel bad.
Never showed up
THE STORY: We had a meeting with the co-founder of a successful brand. We forgot to put it in our calendar and never showed up.
THE REACTION: Angry emails from an assistant asking where the f we were.
THE PANIC: We sent two apology emails, a hand written apology note, and alerted the person who connected us to let them know what happened, and sent flowers. Again. Then two follow up emails. Never heard from her again.
THE LESSON: Nothing annoys us more than when people waste our time so we think it’s fair that said co-founder should have hated us for awhile. Time to move on.
Didn’t pursue enough
THE STORY: We really liked a potential investor. But couldn’t make up our mind about when we were closing our round. So we let the clock tick and tick and tick. When we checked back in with said investor, she was no longer making investments for the year.
THE REACTION: She told us that we didn’t pursue her enough.
THE PANIC: We wrote a letter telling her she was right and why we wanted her involved.
THE LESSON: Go after what you want. Or opportunities will slip by.
Forgot about it
THE STORY: We had an amazing intern who worked for us remotely. And then we forgot about her. We forgot to give her assignments. Forgot to check in. Forgot we had her as a resource.
THE REACTION: The intern kept asking if she could do stuff. We kept putting a note on our to-do list to email her back with an assignment.
THE PANIC: We told her it wasn’t her, it was us. And we meant it.
THE LESSON: Managing is a full-time job. Identify key areas you need help in and look for solutions that you can utilize. But adding ‘help’ for the sake of help, wastes everyone’s time.
NEW ENTREPRENEUR LESSON OF THE DAY: You’re going to make mistakes. Get over them and learn how not to make them again.
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.