Can You Date and Hustle Too? ✨

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Estimated Reading Time: 7 minutes

Hey Fearless Friend!

Today on a Valentine’s edition of Stay Fearless or Die Trying:

1. We have a group for fearless women in CT. Reply to this email if you want me to add you!

2. I break down dating in this startup world… and why it sucks! 💔 (Scroll to the end for my list of ways to meet people!)

3. I’ve been paying my rent with my Bilt card (there’s no fee) and it’s literally genius. I’m not being paid to tell you this but I do get points if you sign up (redeem your points for flights and so much more). Sign up here.

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TLDR of dating from Beehiiv Founder himself:

…and it really feels true this year with Valentine’s Day being yesterday. My Instagram stories were full of date nights, expensive dinners, and gifts. Meanwhile, I’m on my couch cold-pitching brands and waiting for chocolate to go on sale tomorrow.

Dating as an entrepreneur or founder has a special set of challenges. I mean, one simple search on X for “dating entrepreneur” and you’ll see tweets like these:

People assume all entrepreneurs are that one guy from high school who won’t stop posting about his “next big idea.” But real entrepreneurs dedicate years to projects that may or may not succeed, work around the clock, and take big risks:

So why am I bringing this up—just to make you feel worse? Nope! I want our community to break free from this stigma and actually find fulfilling relationships.

My team writer, Beth, found this 2023 Indiana University Study that floored me. I always thought success in this lifestyle meant going it alone, but the study shows otherwise: Entrepreneurs with supportive, engaged partners have both stronger businesses and stronger relationships.

But here’s the catch—finding someone genuinely excited about your startup? That’s a whole other challenge. Entrepreneurs are taking to unconventional methods to find love, like Nick Gray (serial founder and entrepreneur) who flew a blind date to Japan for a special experience:

Something like this sounds right up my alley. I hate dating apps, even the “exclusive” ones like Raya (🤮) and I’ve been compiling ways to meet people for years.

So here’s my list of ways to meet likeminded people (no dating apps required):

1. Turn Networking into Friendworking: Fill your network with interesting, friendly, and ambitious people. Sparks happen naturally in the right circles.

2. Lean Into Entrepreneurship: Join spaces dedicated to founders. No one understands the grind better than a fellow entrepreneur. (Just don’t get a reputation for using networking events as speed dating!)

3. Run Away from Entrepreneurs: Burnt out from business talk over dinner? Try meeting people outside your industry. Join a cooking class, running club, or volunteer. Your hobbies might just lead you to someone amazing.

4. Touch Grass—Literally: Get outside! Go for a walk, visit a park, explore a new café. You can’t meet someone from your couch.

5. Ask Around: Your friends know you best—so why not see if they know someone who might be a great match?

And if your business is your one true love? That’s perfectly okay, too! Don’t let social pressure convince you otherwise.

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