From building apps at Best Buy to getting into Techstars, this episode is a masterclass in startup grit. Our guest, a Toronto-based founder and ex-Apple/IBM engineer, walks us through building 35+ projects, what failed, what made money, how he learned sales from scratch, and why he’s now obsessed with solving go-to-market problems for B2B startups.

We go deep into:

- How to know when to kill an idea

- Lessons from making $0 to 5-figure MRR

- The truth about VC pressure vs bootstrapping

- Building SaaS + service hybrid models

- Staying sane while building solo

Timestamps:

00:00 - Intro: From On Deck to 35 Ideas

01:00 - Why most technical founders fail at sales

04:00 - Best Buy hack: Gaming ad revenue with Android apps

06:30 - First “real” win: Canada Top 10 apps

08:00 - Building “Spotify for News” (and shutting it down)

10:30 - When to kill your startup

13:00 - Side hustle to 1k MRR → quitting full-time job

16:00 - Why learning sales changed everything

18:00 - Selling blueberry honey to learn sales

21:00 - Cold email agency that failed — what went wrong

24:00 - SaaS vs. service models: What scales?

28:00 - “My platform did 10 things. Users wanted 1.”

31:00 - Mission-driven idea testing

35:00 - The 5K/month rule & building in public

38:00 - Should you raise VC or bootstrap?

41:00 - Burnout, support systems & staying sane

45:00 - AI tools stack: Cursor, Claude, Replit & more

50:00 - What actually keeps him going after 35+ tries