Denver, Colorado

Hey, I'm Caleb.

Founder of Cubby. We make smart safety beds for kids with special needs. Happiest when moving fast. Welcome to my corner of the internet.

8M+
Nights slept
15K+
Families helped
~50
Team members
01 The Story

From garage sales to medtech.

My first business was a garage sale. Mom's idea. She said I could keep a cut of the profits. That turned into selling random stuff around the house on eBay. Got in a bit of trouble for that. Then I started importing products from Asia and built a real online store. I was 14.

Studied at University of Waterloo. Caught the startup bug. Traveled and volunteered across 30+ countries. Came back wanting to build something that actually helps people.

Joined SendGrid. Rode it to IPO. Learned what great culture and high-performing teams look like.

Started Cubby. We make safety beds for kids with special needs. Modern. Tech-enabled. Insurance-covered.

Bootstrapped to $1M+ with zero full-time employees.

Cubby got bigger than me. That's the goal.

Now I hire people smarter than me. Thats most of the job. Still figuring out the rest.

02 Off the Clock

Anything with adrenaline.

Snowboarding
Photography
Motorcycles
Mountain Biking
03 Dispatches

Building in public.

People Investments: Why I spend more time on people than product these days.
1,025 engagements
The Bootstrapped Sleep-Preneur: From eBay to medtech.
537 engagements
COO Role: What I learned about finding the right operator.
279 engagements
Welcome, Alex! Announcing our new COO joining the Cubby team.
268 engagements
9,000 Families Strong: A milestone I never imagined when we started.
248 engagements
Help Build Our Dream Team: We're hiring a Sr Recruiter to help us scale.
260 engagements
Follow along on LinkedIn →
04 Principles

How I think.

Raise the ceiling, not the floor.
Hire for slope, not y-intercept.
Move fast. Get reality contact early.
Two-way doors: decide and go.
Energy and enthusiasm are underrated.
Small teams beat bureaucracy.
Focus on what matters.
Do good things with good people.
© 2026 Caleb Polley