How Starting a Business Is a Lot Like a First Date


Long before Tinder, back when I sported a flip phone and still didn’t mind men who courted me using their DJ names, I went on a blind date with someone we’ll call Dustin (or DJ Duz if it helps set the mood).

To make a short story shorter, Duz was a dud. If I remember correctly, I was ready for the check before the sushi was served. The downfall of The Duz had nothing to do with his jokes, his appearance, or how he ate his miso. Duz was a dud because he seemed to have absolutely no idea how much space he was taking up in the conversation. By the end of the meal, I knew everything about him. I knew about his next gig, his favorite album, his car, his cat, and his dentist.

But that wasn’t even the really annoying thing about Mr. Duz. In fact, the reason I remember this evening so vividly was because his behavior shocked me. We had an entire meal together, and he asked zero questions. Every sliver of the conversation I offered up was stomped out by a Duz-focused parallel, a Duzie anecdote, or another pointless name drop. Duz had an ego that knew no bounds.

I guess the only piece of information Dustin retained about me was my phone number, because he continued to call.


Listen up, business owners

Talking to small business owners about their work has taught me a lot. And one connection I’ve only recently made is starting a small business is a lot like going on a first date. It takes guts. A lot could go wrong. And sometimes (hopefully, only sometimes) it can feel like talking to a brick wall.

But the one thing you can do to avoid heartbreak from the beginning of your new business is to listen. Ask questions, learn about your customers, your friends, your competitors, and truly hear them out. You never know what piece of information you might learn that will help you make an important decision for your product, service, sales, or branding. Listening will build trust, and you’ll sleep better knowing you gave your audience a chance to give their two cents.


Love is in the air!

Is there anything more nerve-wracking than a first date? How about starting a business? This Valentine’s Day, we’re spreading the love on social media — and we’re taking our own advice. We want to hear from you!

How is starting a new business like a first date? Are there butterflies? Sweaty palms? Horror stories? Finish the tweet (tag @TSheets!) and share your best small business/first date comparison for a chance to receive a beautiful date night package on us!



We’ve purchased fabulous date night items from small business owners and entrepreneurs, so you can have a fun night in with your sweetheart knowing you’re helping an entrepreneur continue their own love story. (Oh, and we’re throwing in a Fujifilm Instax Mini 90 Instant Film Camera to capture the fun!)


This Valentine’s Day, “Finish the Tweet”

You have from now until February 21, 2018, to give us your small biz/first date comparison. Winners will be chosen in a random drawing and notified via email. Taxes are the responsibility of the winner. Employees of Intuit Inc and their respective parents, subsidiaries, affiliates, advertising agencies, and members of their immediate family, and any persons living in the same household are not eligible to enter or win. The prize is a “Date Night” gift box approximately valued at $500.

Read the official rules here.


Happy Valentine’s Day from all of us here at TSheets!