The Friend Who Goes on Reality TV With You | Episode 3 🎙️

Startups, Rejection, and Building the Impossible with Lindsey Witmer Collins

What happens when your app agency consultant becomes your reality TV co‑star, your startup builder of an impossible idea, and one of your deepest soulmate friends?

Ever had a friend who’d join your wildest pitch?
This is the story of friendship forged in fire.*

In this episode, I sit down with tech founder Lindsey Witmer Collins, the brilliant software architect and tech founder, who saw my Pumpspotting pitch deck and told me I’d be successful in our first meeting. (Obviously, I loved her from day one.)

Lindsey is the friend who said yes to pitching on a moving escalator to Gwyneth Paltrow and Will.i.am, who dreamed up the Breast Express with me at 4 a.m. over tequila after we got rejected, and who spent years in the trenches building a movement that changed the conversation around breastfeeding in America.

We get into the serendipitous mutual friend who introduced us, what Lindsey saw in that original orange‑and‑teal PowerPoint that made her want to work with me, and how we ended up as the very first pitch on the very first episode of Apple TV’s Planet of the Apps.

We talk about standing on that floor getting all green lights from celebrity mentors and still being told no, the devastating rejection that led to our most brilliant idea: a teal‑and‑pink boob‑covered Breast Express and tour the country.

But mostly, we talk about what it takes to build impossible things together. The isolation of being an inventor, the importance of being truly seen in the trenches, and why our friendship survived when the business didn’t. Plus the beautiful role reversal happening now, where I get to support Lindsey’s dream of Scribbly Books after all those years she held me together on her couch.

This isn’t about perfect partnerships. It’s about the messy, ambitious, life-changing kind of friendship where someone matches your vision and says “let’s do it” instead of “are you sure that’s a good idea?”

Have a listen:

“I remember them saying, you’re gonna succeed because you’re so tenacious. Like we were just not gonna give up. You were not gonna give up.”

In this episode, we get into:

• How a Costa Rica wellness retreat led to meeting your soulmate business friend

• What Lindsey saw in Amy’s pitch deck that made her know she’d succeed

• Pitching on a moving escalator to Gwyneth Paltrow, Will.i.am, Gary Vee, and Jessica Alba

• Getting all green lights on Apple’s Planet of the Apps and still being rejected

• The 4 a.m. tequila margarita moment that birthed the Breast Express

• Building a teal‑and‑pink boob bus and touring the country (Vogue, BBC, local news everywhere)

• What it actually costs emotionally to invent something that’s never existed before

• Why building businesses together can destroy or deepen friendship, and what makes the difference

• The beautiful role reversal: supporting each other’s dreams across a decade

• Soulmate friends vs. acquaintances we call friends (and why the precious few matter so much)

• AI, social fabric, and why we need to learn our UPS driver’s name

• Plus: Why Midwest friends are the best friends, Lindsey’s legendary gift‑giving, and whether you should say yes to reality TV with your friends
  

Perfect for anyone building something big and impossible right now, wondering if friendships can survive when businesses don’t, or looking for that one person who says “let’s build a bus” instead of “are you sure?”

Lindsey’s Friend Picks

Lindsey’s current obsessions she’s gifting to all her friends:

• Small dogs (Happy will make you want one.)

• OJS‑M sparkly nail polish from Olive & June (so forgiving when it chips you can’t even tell)

• Lake Pajamas for maximum coziness (I got them for Christmas & am also in love)

Special mention: Check out Lindsey’s company Scribbly Books, where she creates magical custom illustrated storybooks featuring your kids as the main characters. Every page is a work of art and my kids are obsessed.

Join the campfire conversation

Talk to us: Who’s the friend who said “let’s do it” instead of “are you sure?” Have you ever had a friendship forged through building something impossible together? Tell us your stories.

If you’re building something big right now and you have that one friend who doesn’t ask “are you sure?” but says “let’s figure it out”, send them this episode. Tell them you see them.

Follow the show on your favorite podcast platform so you never miss an episode, and come hang out with us on Instagram @theyeahnoforsureshow for behind‑the‑scenes moments and campfire energy.

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*Fun fact: When we say friendship forged in fire we mean it: Lindsey and I have been in many high-stakes scenarios together from reality TV to big investor pitches (while pumping) to live QVC. Talk about trust…she’s seen me at my most nervous and vulnerable and still stuck around.