Episode

The Founder Who Outsmarted $100M Competitors and Created His Own Exit - Donal Greene - Trustmatic

Donal Greene built lean, moved fast, and turned a cold DM into an acquisition beating far better funded competitors without playing the usual startup game. Toronto Tech Week, in its first proper form, felt like a cultural shift: still early, but starting to reach beyond the usual crowd.

Episode

Startups Are Changing & Ecosystems Need to Catch Up

Why most startup ecosystems are falling behind in the AI era and what top cities like Philadelphia are doing differently. JF Gauthier of Startup Genome joins Rob at Web Summit Vancouver 2025 to unpack how policy, capital, and culture must evolve.

Episode

Are AI startups still building products? Or just vibes?

AI startups aren’t building apps. They’re building coworkers and skipping the roadmap while doing so. I debate vibe coding. And a Web Summit Vancouver 2025 recap.

Episode

Connor Gaydos Bought Enron to Fix America's Energy Crisis - Consensus 2025

At Consensus 2025, I stumbled on something surreal: Enron is back. The once-disgraced brand is being rebooted by a meme-maker to solve America’s energy crisis—with batteries, nuclear energy, Web3 tokens, and transparency.

Episode

Austria: The Startup Bridge Between East and West

Austria’s startup scene is quietly exploding, thanks to a new EU-wide legal framework, Vienna’s unmatched livability, and its unique East–West access.

Episode

Startup Boards That Actually Drive Results with Breen Sullivan of The Fourth Effect

Early-stage startup advisory and fiduciary boards are often set up… incorrectly. One secret weapon to supercharge growth - and avoid huge mistakes - might just be hiding in plain sight: strategic advisory and governing boards.

Episode

FreightSimple’s Solution to Shipping's Biggest Headache with Natasha Ross

Freight logistics quietly powers our economy - until it breaks. Natasha Ross, cofounder of FreightSimple, shares candid insights into fixing shipping absurdities, gaining trust in skeptical markets, and why solving “boring” problems unlocks huge startup opportunities.

Episode

DeepSeek vs. OpenAI: What This Means for AI Startups with Ryan Henry

Most AI startups today are just wrappers around existing tech. So how do you build something that lasts? In this episode, we break down how AI really works, where the real moats are, and how founders can win in a rapidly evolving landscape.

Episode

Melissa Kwan // eWebinar - Burnout, Bootstrapping, & Building Better

Decelerator with Rob Kenedi Episode 2: Melissa Kwan of eWebinar.

Update

On Failure (?)

Let's talk about "failure".

Episode

Jennifer Yip // Lunch Money

Decelerator with Rob Kenedi Episode 1: Jennifer Yip of Lunch Money.

Update

Drop Week & The State of SaaS

The state of SaaS in Canada with Chris Arsenault of iNovia and the Episode 1 drop party.

Update

🚀 Yes, Episode I

A drop party, a quantum chemistry pod, and a dollop of Geoffrey Hinton.

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The software consulting business model: what's next?

Software consulting business models and a song to get you through the week.

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Startup demo day season has already begun

YSpace demo day, startup patterns, and a track to listen to while reading the newsletter.

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A Northern Irish trade mission

Following a trade mission from Northern Ireland, and follow & chat with us on our social channels.

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Canada's AI Supercluster had an event...

The ALL IN AI conference in Montréal & rock music. Like peanut butter and chocolate.

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Happy New Fall

The fake new year and I'm hosting part of an AI conference in Montréal.

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Founders, play your own game

On bring funny & a state of the fintech union.

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It has begun...

The first interview has been recorded, a summer soirée, and some plant based salmon.

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Purgatory & AI Generated Music

Whew, well last week's Collision was quite the 40C + humidity week, with too many events and people to even start listing. I do like the conference and, while I'm sad it's leaving TO, I'm happy that Vancouver's taken up the

Update

The final Collision

This week in Toronto is the last Collision conference ever. A version of it is moving to Vancouver, rebranded as Web Summit. So, this week is a busy one and if you're here, make sure you say hi. I'm going to these things (check out the

Update

A Crank, A Pedal, Tools & Entertainment

Hey folks, happy almost summer. An action packed first note to you all! We're one turn of the crank into the production of the show, but in the meantime we've been up to a ton. We even have a special invite for you at the end,

Show

Decelerator Teaser

A talk show style series focusing on entrepreneurs, investors, & ecosystems building tech companies differently, hosted by Rob Kenedi. The fake testimonial AI was generated by Syed Iftikhar.