A Product Market Fit Show | Startup Podcast for Founders

He sold SkipTheDishes for $200M—then grew Neo Financial to a $1B valuation. | Jeff Adamson, Co-Founder of NeoFinancial & SkipTheDishes

Mar 24, 2025

Jeff Adamson, co-founder of SkipTheDishes and Neo Financial, shares his remarkable journey from launching a food delivery service that dominated Canada to creating a billion-dollar digital bank. He discusses overcoming initial rejections and adapting strategies to build trust with customers. Jeff reflects on the emotional weight of selling Skip and how he pivoted to take on the banking industry. He also emphasizes the importance of resilience, continuous improvement, and the messy but crucial beginnings of any venture.

01:01:06

Episode guests

Jeff Adamson

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Episode notes

Podcast summary created with Snipd AI

Quick takeaways

Early-stage entrepreneurs must embrace rejection while actively seeking genuine feedback from stakeholders to align their offerings with market needs.

Building robust partnerships with local businesses is essential for fostering trust and driving mutual success in competitive markets.

Developing proprietary technology is crucial for financial startups, as it enhances customer experience and supports sustainable growth amidst economic changes.

Deep dives

Feedback-Driven Approach

Gathering feedback early on is crucial for building a successful business. Entrepreneurs shared their experiences of approaching restaurant owners, often facing rejection and skepticism, while emphasizing the importance of persistence. Validating ideas through direct feedback helped them understand what restaurant owners truly valued, shifting their approach from scripted pitches to authentic conversations. This adaptability laid the foundation for their subsequent success by ensuring their services aligned with actual market needs.

Intro

4min

From Campus to Cuisine: The Journey of a Canadian Food Delivery Service

11min

Navigating the Launch of a Food Delivery Service

15min

The Journey of Building a Food Delivery Brand

3min

Reflections on a Milestone Exit and Its Real Impact

2min

Navigating Canada's Fintech Landscape

24min

Navigating Growth and Product Fit in Startups

3min

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

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