From “We’ve made it!” to “Oh sh*t, now what?” — I’m sharing the real story of building Proposify.

I’ve been building Proposify for over a decade — through bootstrapping, hyper-growth, hiring execs, missing goals, fixing culture, shipping great (and not-so-great) products, and somehow coming out the other side.

This newsletter is where I break it all down — what worked, what didn’t, and what I’d do differently — so you can build smarter, faster, and with fewer sleepless nights.

Kyle Racki, CEO and Co-founder of Proposify.
Fascinating article, Kyle. Love your honesty and vulnerability here.

- Ton

I feel like you’re writing these emails - certainly this one - right to me.

- Paul

Really appreciate these emails. Motivating and grounding. Both are much needed!

- Melanie

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What You’ll Get

  • Behind-the-scenes lessons on SaaS growth, leadership, and product

  • Data-driven insights from running a PLG + sales-led company

  • Stories from the trenches on hiring, culture, and hard decisions

  • Frameworks and mental models I use to scale teams and products

  • Occasional failures (and what they taught me)

👉 Join 10+ years of lessons from the trenches
Get one story, framework, or insight each week — straight from my desk at Proposify.

Hey Kyle, One of the best newsletters I’ve gotten in my inbox in a while.

jenny

Jenny Beres
President & Co-Founder, Pink Shark PR