5 Things Entrepreneurs Can Learn from Online Dating If you're looking for the perfect match, here are five ways online dating might just sharpen your entrepreneurial acumen.

By Dorie Clark Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.

Online dating is notoriously frustrating, from out-of-date pictures and misrepresented bios to uncomfortable meetings where only propriety prevents you from bolting immediately. But as an entrepreneur braving the wilds of Internet matchmaking, I've discovered over the past few months that there are some crucial lessons we can all learn from the (sometimes painful) process. If you're looking for the perfect match, here are five ways online dating might just sharpen your entrepreneurial acumen.

Enhancing your market research. The process of meeting people – and seeing what they're looking for – can be an interesting reality check. What do our competitors have to offer? How do we measure up? And are there small ways we could improve or upgrade? You can't (and shouldn't) change your personality, but you may be able to pique a few more people's interest if you cultivate new "product features" like an interest in visiting art galleries or going to wine tastings.

Related: Do Pass Go: Business Lessons From Monopoly

Crystallizing your value proposition. What makes you stand out? Why should someone choose you? You can probably explain this in your sleep for your product or your company – but it's a lot harder to do it for ourselves. Filling out (often extensive) online profiles is an exercise in self-knowledge, and forces us to consider where we excel. Do you emphasize your sense of humor, or your caring nature? Your keen intellect, or your MacGyver-like adaptability? You have to get inside the head of your "customer" and figure out what they most want.

Streamlining your sales funnel. In your company, not every customer inquiry leads to a sale. Over time, you learn how to weed out bad prospects, and how to nurture good leads into satisfied long-term customers. Similarly, online dating provides enough volume so you can begin to understand what a good (or bad) prospect looks like. How can you spot them early, and either cultivate them – through good conversation and intelligent questions – or quickly get out of Dodge?

Related: 4 'Magical' Keys to Business From My Stint at Disney World

Making the ask. Sometimes – in business and in life – we're hesitant to make a direct ask, relying instead on hints or guesses. It might spare our egos in the moment. But in the long term, it's a disastrous strategy: years later, how would you feel if you discovered you missed out on a major contract, or a possible relationship with someone amazing, because you misunderstood the signals? Online dating teaches you to be clear and direct – and that way, at least you know for sure.

Dealing with rejection. Clearly, no one likes rejection. But any entrepreneur who succeeds 100% of the time needs to start selling to people besides Mom and Dad. Failure is an inevitable part of stretching and growing your business – and the same goes for your personal life. You're going to find plenty of people through online dating who might seem like good prospects but somehow don't fully recognize the quality you're offering (like my recent date, who rushed home after an hour because she "forgot to feed the cat"). Each rejection is data you can use in the future, to tighten up your sales funnel and make better projections about who will ultimately be the right "customer" for you. But it is a numbers game, and that means you'll face a lot more failure than success. That may seem discouraging while it's happening. But when success comes, it's like your startup going public – exponential returns beyond what you can possibly imagine.

Related: The 7 Management Lessons of Pope Francis

Dorie Clark

Speaker, Marketing Strategist, Professor

Dorie Clark is a marketing strategist and speaker who teaches at Duke University’s Fuqua School of Business. She is the author of Reinventing You. 

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Starting a Business

How to Build a Side Hustle That Stands on Its Own — Without Burning Out

Ready to take your side hustle to the next level? This article shows you how to turn it into its own unique brand that gets noticed and grows on its own.

Business Ideas

70 Small Business Ideas to Start in 2025

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2025.

Science & Technology

101 Small Business Ideas to Match Your Personality, Investment, Skills & Goals

Still stuck on what biz to start? Use AI to uncover 101 custom ideas aligned with your skills, values & lifestyle—plus a 90-day roadmap to launch with clarity.

Business Solutions

Access 25 Hours of AI Training for Less Than $20

This e-degree gives you hands-on AI training that's perfect for entrepreneurs wearing many hats.

Productivity

Squeeze a Whole Business Book into Your Lunch Break

Power through 1,800+ titles without falling behind on your calendar.

Branding

How to Remove or Bury Negative Articles on Google

Here's how to remove negative articles from Google search results, protect your brand reputation and suppress harmful content.