I'm an ocean dweller living in a seaside down just outside of Boston.  I live for rainy days, vintage dresses, and the perfect full-fat cappuccino. You’ll catch me cold plunging year-round with girlfriends, chasing my sons around, or on date night with my husband, Tom.  I'm a serial entrepreneur and use work as a vehicle to do good.  If I'm lucky I'm in bed by 9, book in hand, recharging for whatever magic (or mayhem) tomorrow brings.

I'm an ocean dweller living in a seaside town just outside of Boston. I live for a season change, vintage dresses, and the perfect full-fat cappuccino. You’ll catch me cold plunging, chasing my sons around, or on date night with my husband. I'm a serial entrepreneur who uses work as a vehicle for good. If I'm lucky I'm in bed by 9, book in hand, recharging for whatever magic (or mayhem) tomorrow brings.

Wife, boy mom to two,
lover of rainy days,
anti-hustle enthusiast

Wife, boy mom to two,
lover of rainy days,
anti-hustle enthusiast

A BIT ABOUT ME

After years of building brands, communities, and momentum, I’ve learned the most powerful thing you can offer is your full self.

I’m in a season of staying close to what matters. Breathwork before inbox. Walks with my kids after school. Good coffee, early mornings, honest work, and plenty of room to feel what’s real.

For years, I ran Olives & Grace, built communities, launched brands, and held space for hundreds of founders. I’ve loved the spotlight, but I’ve also learned how much of me was tied up in producing. Performing. Proving.

I’m not chasing the next big thing—I’m choosing the next right thing. That’s what guides my work now. What feels good, what feels honest, what has room to breathe.

I host Founder dinners. 6am meditations, Community Reflection Circles, I listen intently when my three-year-old tells me about Hulk Smash. And I keep daring myself to live a full, dynamic life. Not for applause, but because this is what I came here to do.

I’m not interested in toggling between founder and mother like two separate selves. I’m building a life where the Venn diagram overlaps—where who I am at work and who I am at home feel connected, not compartmentalized. Where the version of me who leads and the version who mothers share the same presence, values, and softness.

That overlap is the space I’m protecting. It’s where I move from. It’s the work I’m doing.
And if you’re here for that, too—welcome.

Presence over performance.
Connection over clout.

Photographing your moments in San Francisco, California

Sofi Madison