Jeff Adamson co-founded SkipTheDishes, scaled it to 80% market share, and sold it for $200M—all before Uber Eats and DoorDash even got serious about Canada. He started with zero tech experience, got doors slammed in his face by restaurant owners, and had to personally place orders just to keep early partners engaged. Then, when Uber Eats launched in Toronto, backed by billions in funding, he thought it was over.

Instead, Skip became Canada’s dominant food delivery platform and got acquired for $200M.

Then Jeff did something even crazier—he decided to take on the banks.

With Neo Financial, he’s tackling Canada’s most entrenched industry, building a modern, full-stack digital bank from scratch. He's raised $100s of millions at a $1B valuation.

Why you should listen:

How bootstrapped SkipTheDishes took on $10B UberEats
How to build a three-sided marketplace.
Why building trust with customers is key to long-term success.
Why beginnings are always messy and more about grit than perfection.
Why Jeff didn't stop after exiting for $200M.

Keywords
SkiptheDishes, Neo Financial, entrepreneurship, delivery service, startup journey, market competition, founding team, restaurant industry, business growth, feedback loop, three-sided marketplace, startup journey, Canadian startups, entrepreneurship, financial services, exit strategy, partnerships, growth strategies, advice for founders

Timestamps
(00:00:00) Intro
(00:02:00) Gotta Have Thick Skin
(00:03:54) Skip's Origin Story
(00:07:18) Competing with Uber
(00:16:09) The First Few Restaurants
(00:22:45) Initial Demand
(00:26:28) Three-Sided Marketplace
(00:38:38) The Original Mission
(00:52:10) The First Year at Neo
(00:58:40) Product Market Fit
(00:59:55) A Piece of Advice

Send me a message to let me know what you think!

268: When You’re Compelled To Serve With Leann Vitale, MS, OTR/L