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Starting a Business: Things I’d Tell My 90-Day Self


I started North Street ten years ago as a freelance web designer and developer with too many projects to handle on my own. It started innocently enough. Then I started hiring and managing freelancers to pick up the slack—and now here we are 10 years later with a long-term office lease, full-time employees, 401ks, and an actual business. 🤘

Recently, I was asked to reflect on my first 90 days as a business owner and think about the advice I’d give myself. It was fun exercise that made me realize just how much I’ve learned—mostly through mistakes—over the last 10 years. Here’s what I came up with:

You Can’t Do it All

It’ll become quickly apparent that you can’t do everything yourself. Identify those things that lie at the intersection of what you like to do and what you do best and focus there. Delegate as much of the other stuff as you can.


The best thing I did early on was to hire an accountant to reconcile my books, pay vendors, invoice clients, chase down AR, and pay quarterly tax estimates. These activities could take up half your week if you let them, leaving you little time for anything else. Consider hiring one of the many fractional CFO and bookkeeping services out there.


Open a separate bank account dedicated solely to what you need to sock away for taxes and then forget it exists. Pretend it isn’t there. Your accountant, bookkeeper, or fractional CFO can advise on the percentage of earnings you should save. Too many first time business owners don’t take this into account and get sunk by a surprise tax bill they can’t pay.


In addition to tax savings, I recommend building up a minimum of two months of overhead in cash. This will help you ride out the dry times as you establish steady streams of income. It’s also a rainy day fund for when something like—I don’t know—a global pandemic suddenly erases most of your dependable revenue.


I didn’t even know this was a thing until I was in business for more than 7 years. You’re going to have down months and even down years. A line of credit provides instant (but not free) access to cash when you’re in a pinch like, say, needing to pay employees and vendors while waiting for an overdue client check to come in.


Whether it’s a formal relationship or not, find someone you can talk to who has already run the traps. Owning a business can sometimes feel like you’re in a vacuum. You experience issues and stressors that your friends, family, and employees can’t possibly understand. Early on I had the good fortune of befriending the owner of an agency like mine, but much bigger and more established. He became something of an oracle—someone I could call any time to talk through a client, employee, or financial issue.

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