My friend Alisa told me something completely matter‑of‑fact: “I suck at friendship.” Not apologetically. Not with shame. Just as a plain, true thing.

Alisa loves people. She’s a birth doula, angel investor, and the woman who became my founder doula during the hardest years of building Pumpspotting. She listens in a way that makes you feel fully seen. She just has a very specific idea of what friendship actually means—someone you’d give a kidney to, someone who’d be in your delivery room—and by that definition, she feels like she’s failed more than she’s succeeded.

This conversation goes deep. We talk about the grief of losing friends you thought would be there forever, and looking honestly at your own part in those endings. About what friendship in your 50s feels like when you finally have time and you're choosing people with intention. About surviving the teenage daughter years to become friends on the other side. And at the end, Alisa tells me something I wasn't expecting: that I'm the first person she's ever done friendship differently with.

If you’ve ever lost someone you loved and wondered what your role was, or you’re in midlife craving friendships that are real and chosen and yours, this episode is for you. Stay with it all the way through; it only gets richer.

Join the campfire → yeahnoforsure.com | Instagram → @theyeahnoforsureshow

Follow Your New Friend Alisa Marie:

The Mothership on Substack | Let's Talk Birthy | @LetsTalkBirthy

Alisa’s Friend Pick: The Besque Body Oil she’s gifting everyone she loves right now.

What happens when reality TV says no, but your friendship says yes and you build something impossible together anyway?

I sit down with Lindsey Witmer Collins, the brilliant software architect and tech founder who saw my Pumpspotting pitch deck and believed I’d succeed before we’d even met. We pitched to Gwyneth Paltrow and Will.i.am on a moving escalator for Apple TV’s Planet of the Apps, got all green lights, and still got rejected. So we drank tequila until 4 a.m., dreamed up the Breast Express, and spent the next few years proving everyone wrong by building a startup that changed the conversation around breastfeeding.

We talk about what it’s like when your app consultant becomes one of your soulmate friends, the isolation of being an inventor, and why our friendship survived when the business didn’t. We get into the serendipitous Costa Rica connection that brought us together, standing in that pitch circle refusing to back down, and the beautiful role reversal happening now where I support her dream of Scribbly Books after years of her holding me together on her couch.

This isn’t about perfect partnerships. It’s about startup friendships forged in fire - matching someone’s ambition, saying “let’s do it” instead of “are you sure?”, and building something that changes lives even when it doesn’t work out the way you planned.

For anyone building something impossible, wondering if friendships survive business failures, or looking for that one person who sees your vision before anyone else does.

Lindsey’s Friend Pick: Small dogs, sparkly OJS‑M nail polish from Olive & June, and Lake Pajamas.

Join the campfire → yeahnoforsure.com | Instagram → @theyeahnoforsureshow

Follow Your New Friend Lindsey:

Scribbly Books | WLCM App Studio | Website

@ScribblyBooks | LinkedIn

What happens when a friendship hits a breaking point, and you choose to repair it instead of run?

I sit down with Holly Curtis—brilliant creative director, sauna companion, and the friend who answered the phone when I had my first panic attack in an orthodontist parking lot. Holly and I have been friends for a decade, we're on each other's emergency contact lists for literally everything, and we almost lost each other.

We talk about the Newport Folk Festival rupture, the midnight apology letter, and why we decided this friendship was worth fighting for. But we also get into matching metallic snowsuits through Covid fires, constantly lowering our expectations and being really excited when plans actually happen, and the Gilmore Girls vs. Parenthood debate.

This isn't about perfect friendship. It's about the messy, vulnerable, life-saving kind - the kind where you can call from a parking lot and someone says, "I can feel that you're not okay."

For anyone who’s ever almost lost a friend, wonders if deep friendship is still possible in midlife, or knows the feeling of calling someone, crying from a parking lot.

Follow Holly on Instagram.

Join the campfire → www.yeahnoforsure.com | Instagram → @theyeahnoforsureshow

Holly's Friend Pick: Wooden Spoon Magic Magnesium for better sleep (way better than another glass of rosé). Use code YEAHNOFORSURE for 10% off.