7 min 4 sec

Online Dating Profile Service Turns Frogs Into Princes

A Massachusetts woman helps men improve their online dating profiles. Tip #1: stop being creepy.
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What It's About

From frogs to princes—this woman helps men stand out!

Business Model
Skills Required
Communication & Writing
Profit Potential

Words of Wisdom

Here's a bonus lesson from Emma (#1 dating profile tip):

"One of the tips I always give is to be specific and to add in little anecdotes/stories. So many online dating profiles are really vague, and it's hard for people to relate or latch on to anything in the profile. It's as simple as listing three books you loved and why you loved them rather than saying 'I like science fiction.'"

Fun Fact

Emma’s side hustle didn’t become a six-figure business, but it did lead to a new job. It also gave her the confidence that she needed to continue experimenting with her writing, and she now works for herself full-time.

Notes from Chris

Episode 443
Something like 30% of long-term relationships now begin through online dating. But this world can be tough to navigate, and you need an edge. Or that’s what one Massachusetts woman thought when she started an unconventional and temporary side hustle.

More than 50 million people in the U.S. alone have tried online dating. That means they have made an online dating profile. Emma Siemasko had recently met her boyfriend, who is now her husband, through online dating. As millions of people know, wading through a sea of thousands of profiles can be overwhelming. And if you’re a guy, in particular, you really need to stand out.

Based on her experience, Emma had noticed—how to put this—that so many profiles, well, sucked. They would be boring, lame, or creepy… three qualities that did not inspire most women to respond. Her goal was to help men optimize their online dating profile so that they'd perform better in the crazy pool of competitors.

She had been successful herself, meeting that boyfriend who would later become her husband. She’d helped out a few friends, showing them how to better describe themselves in a way that sounded attractive without being overconfident. And then one of those friends said, “This should be a business!”

Listen: the business didn’t scale, it didn’t make a ton of money, it didn’t become her full-time work. But it did something else, perhaps something even greater than those things.

Sometimes a small project can lead to something greater, and in this case, Emma can point to two big changes that came from saying, “OK, I’ll give that a try.”

The first was landing a new job. Frog2Prince was the most impressive thing on her resume to the employer where she worked afterwards. She has she didn’t have as much experience as the role called for, but they were impressed by her ability to make things happen. They hired her because of her side hustle.

The online dating profile service may have made just $800, but she traces her current status to that decision to try something new. That’s right, it all started with a Frog that became a prince… or at least got closer to princedom.


  • Frog2Prince: Go from a frog to a prince—check out Emma's website for profile tips and tricks!

  • Stories By Emma: Learn more about Emma and the services she offers over on her website


Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

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Quote of the Day
"On my online dating profile, I told people that I was currently trying not to eat candy, and asked them to come ask me how I'm doing with that. It gave people an easy in to say, 'Hey, how much candy have you eaten lately?' I used to call this 'giving people hooks.'"
—Emma Siemasko #SideHustleSchool

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Chris Guillebeau