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The Speakeasy

You got into business for freedom. But behind the scenes of your hard-won success is a solopreneur working long hours and second-guessing decisions. We need sustainable business and marketing strategies. We crave meaningful conversations. And we want unfiltered fun.This isn't just content. It's a community - one in which curiosity, self-expression, and heart are the only prerequisites. Online business owners, this is your stomping ground. (Warning: You may be asked to spill your guts.)

Get scrappy.

MADE WITH LOVE & GUTS BY ⏲ DAYLIGHT EDITION Think back to when you first started your business. How scrappy you were then. How creative. How bold. You created offerings you were excited about, even if they weren’t yet refined. You launched a website and told people about it, even though it wasn’t polished. You pitched dream clients and podcast hosts, even though you were a relative unknown. Maybe success came quickly, or maybe it took a while to gain traction. Maybe you spent way too much...

There are two kinds of perfectionists.

MADE WITH LOVE & GUTS BY 🎉 NEW YEAR'S EDITION Back in October, I kicked off a somewhat unexpected and completely life-altering journey by enrolling in yoga teacher training. So far, it’s been humbling, joyful, and revelatory in every way. And I gotta say, it’s been a much-needed counterbalance to—and perspective shift from—my routines and thought patterns of late. As Semisonic’s “Closing Time” plays on 2024, one of the many things I’m meditating on with this renewed, ever-evolving outlook is...

Show your work.

MADE WITH LOVE & GUTS BY ⏲ DAYLIGHT EDITION Hey Reader, I don’t know if it’s because it’s back-to-school season or because I’m teaching a Draft House workshop tomorrow (it’s not too late to join us!), but I’m having flashbacks to math class today. Weirdly, that made me think about marketing. Let me explain. Remember how on math tests, it wasn’t enough to get the answers right? You also had to show your work? (So, if copying the answers from the boy you were flirting with was your strategy,...

51 alternatives to wasting your time on IG.

MADE WITH LOVE & GUTS BY ⏲ DAYLIGHT EDITION Nearly every business owner I talk to who markets on Instagram has a love/hate relationship with it. It's like a toxic relationship: You give everything to try and please the algorithm and it rarely loves you back. You feel like you can't leave the platform because where else will you find that kind of potential reach? You think you've finally figured out what works, and then they move the goalpost. You remember the good days when reach and...

You got into business for freedom. But behind the scenes of your hard-won success is a solopreneur working long hours and second-guessing decisions. We need sustainable business and marketing strategies. We crave meaningful conversations. And we want unfiltered fun.This isn't just content. It's a community - one in which curiosity, self-expression, and heart are the only prerequisites. Online business owners, this is your stomping ground. (Warning: You may be asked to spill your guts.)