dear founder,

september didn't go according to plan. & that's exactly what needed to happen.

this was the month we stopped pretending we had it all figured out & started doing the actual work of figuring it out. messy conversations replaced polite ones. hard truths replaced comfortable assumptions.

less performing, more becoming.

the moments that changed everything:

• the vault breakthrough happened. after months of building toward something that felt "almost right," the crab boil dinner became our inflection point. not because the food was good (it was), but because that's where we finally said the things we'd been scared to say.

• user feedback started speaking louder than our assumptions. nine test users had been trying to tell us something. we'd been so busy falling in love with our product that we forgot to fall in love with our customer. tony robbins was right: emotion connected to information is unstoppable.

• team communication leveled up. stopped explaining ourselves to each other & started actually hearing each other. the indirect communication through relationships? dead. direct founder-to-team clarity? alive.

• in-person time proved everything. escape rooms, long dinners, & real conversations. the vault wasn't just a conference—it was proof that we do our best work when we're in the same room, working on the same problems.

• leadership fears dissolved. turns out the thing i was most scared to do (tell the team we weren't ready) was exactly what we all needed to hear. fear of disappointing people was keeping us from serving them.

challenges that became clarity:

• the $17k question got real. when your developer says "you need more validation before you build this," & you realize they're right, you have two choices: ignore it or listen. we listened.

• comfortable got uncomfortable. we were acting like we'd already made it instead of acknowledging we're still making it. comfort was the enemy of growth.

• systems needed systems. amazing people aren't enough without amazing processes connecting them. we're building those bridges now.

what i'm carrying:

sometimes the breakdown is the breakthrough.

nine users who gave us feedback we weren't ready to hear.
team conversations that solved problems instead of avoiding them.
in-person moments that reminded us why we're building this together.
the realization that being scared to lead was keeping me from leading.

we're not building a product anymore.
we're building the people capable of building the right produc

looking into october:

daily insights that actually stick.
user conversations that go deeper.
team systems that actually serve the mission.
leadership that leads from truth, not comfort.

we're not starting over.
we're starting from something real.

the messy middle is where the magic happens.
& we're right in the thick of it.

with purpose, vision, & deep appreciation for this team,

Brooke

p.s. to the founder reading this who's been avoiding that conversation, that decision, that truth you know needs to be said—you're not alone in the fear. but the thing you're most scared to face? that's probably exactly where your breakthrough is waiting. have the conversation. admit the thing. take the action. the messy middle is where we all live, & it's where the real work gets done.

Brooke Sherwood

CEO & Founder

+1 (719) 565-9196

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