Hey, I'm Caleb.
Founder, builder, and happiest when moving fast. Welcome to my corner of the internet.
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. 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. Now I hire people smarter than me and figure out where we're going.
Based in Colorado. Snowboard, motorcycles, mountain bikes. Anything with adrenaline and flow.
Behind the Scenes
Building Cubby in public
People Investments: Why I spend more time on people than product these days...
1025 engagementsThe Bootstrapped Sleep-Preneur: How I went from selling on eBay to building a medtech company...
537 engagementsCOO Role: What I learned about finding the right operator for your startup...
279 engagementsWelcome, Alex! Excited to announce our new COO joining the Cubby team...
268 engagements9,000 Families Strong: A milestone I never imagined when we started...
248 engagementsHelp Build Our Dream Team: We're hiring a Sr Recruiter to help us scale...
260 engagementsHow 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