We focused on the hot topics du jour. The investor panel with Green Sky Ventures, InterGen Capital, and Imbue Capital focused on the changing shape of capital markets. What stood out for me was the signal-to-noise problem created by the sheer volume of new startups, angels overpricing rounds negatively affecting their future returns, and the decision point around stalling at $3-7M ARR (or just revenue if it’s not recurring) and whether it’s worth seeking an exit or not.

The operator panel with #paid and Solink - both mature, venture backed companies - covered the other hot topics: AI eats features, price the outcome not the token, trust matters, and cleverness is not a moat. It's also worth noting I did poke them a bit because at this point decade-old startups are… incumbents? Disruptees? We don't have a word for the company that was scrappy six years ago and is now the one being undercut by AI-native competitors on weekends. We should. I nominate “mature startups”.

The one moment that made me laugh was when the investor panel converged, to my surprise, on the idea that services revenue is fine now, actually, as it gets you in to deliver outcomes and builds a relationship pure SaaS businesses can’t replicate. So we have come full circle. Angels should be investing in services companies. You heard it here first, and also in 2003.

Looping back to “what happens after you accept that not every company is venture-tracked and decide to go the other way”, at Startupfest I sat down with Mishel Wong, founder of BoPaq, a Montréal company replacing single-use takeout containers with reusable ones. Good business, real traction, doesn’t fit a VC bucket given reverse logistics, physical infrastructure, and behaviour change. Exactly the kind of company the ecosystem keeps quietly calling a failure for not unicorning. And she was super open and brutally honest - worth a listen since entrepreneurs don’t often share such raw details, especially mid-decision-making.

Mishel went the strategic acquisition route. The first deal fell apart at the altar. She described it like getting left at the wedding by someone who suddenly realized they didn’t actually want kids, even though kids had been the plan the whole time. The acquirer hadn’t fully reckoned with what taking on reverse logistics actually meant, and walked once reality set in. She moved into due diligence with a second partner, going in with a sharper rule: surface the ugliest operational realities first, on purpose, before anyone gets emotionally committed. They've since closed the deal.

That’s the part worth sitting with. The alternative paths get pitched as the calmer option. They’re not. The hard part just moves. It moves from “can I raise the next round” to “does the operational reality of my business survive contact with a partner’s spreadsheet.” Most founders aren’t trained for that conversation. Most acquirers aren’t either.

First up: Kare Chemical Technologies.

Kare makes pharmaceutical-grade cannabinoids out of orange peels. Orange peels. It’s a patented catalytic process already being licensed to pharma manufacturers. The applications they’re most excited about aren’t recreational anything. They’re non-addictive alternatives to opioids and treatments for pediatric epilepsy. They recently closed a $750K pre-seed round with a very small team.

This is the kind of company I think gets undercounted right now. Not a vibes-based AI wrapper. Not a “we’re disrupting [established industry] with [LLM]” deck. Just deep, weird, hard chemistry being done by people who’ve been at it for years and have something real to show for it.

Which is also kind of why I’m at NACO. I’m less interested in what founders are pitching - that’s a known quantity - and more interested in what investors are actually thinking about right now. Not just the sectors they’re chasing (hard tech? health? climate?) but how they’re thinking about the job itself. What’s keeping them up. What they got wrong in the last cycle. How much of their thesis is conviction versus what the LPs will tolerate. And underneath all of that, a question I find genuinely interesting: where does Canadian capital think it’s going? There’s a real conversation happening up here about decoupling from US dependence… Sovereign wealth funds, domestic angel networks, less embarrassment about backing things on home soil like defence, which until recently was a negative signal and now everyone is “in defence”… and I want to know if the people writing cheques believe it or are just nodding politely on panels.

In the meantime: orange peels. Enjoy.

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I’ve been a SXSW Pitch judge for two years now, and this year I noticed something running underneath almost every conversation I had - about AI, about music, about self-driving cars - worth naming.

Everybody on every panel and stage was talking about trust. Trust is the new moat. Trust is the new differentiator. Trust trust trust. Fine. But “trust” is doing so much work right now that it’s starting to mean nothing, which I think is a bit of a problem when you’re trying to build something. So let me try a more useful word: receipts.

When everyone has the same tools and the output is cheap to produce, what’s left is the trail behind the output. The reasoning, the track record, the proof, the why. The stuff that’s actually hard to fake.

Let me show you what I mean with a three act vignette.

The Kids Are Buying CDs

I was having fried chicken at Gus’s, and, over the inability to make eye contact with our server, started chatting with a chap who does strategy at Universal Music and negotiates the deals with the streaming companies. He told me that kids these days (👴🏻) are now buying… CDs and CD players. They’re cheap, you have ownership over the media (inasmuch as one can), they’re tangible, and… no screens, no algorithm deciding what’s next.

This stuck with me because it’s not really about CDs. It’s about the fact that the streaming model asks you to take everything on faith: that the song will still be there next week, that your subscription will still exist, that Amazon won’t take the book away, that the playlist hasn’t been quietly reordered for reasons the algorithm doesn’t owe you. A CD is a receipt. You can hold it. It’s evidence that a transaction happened and that a thing exists and will continue to exist whether or not a Series C startup decides to pivot.

That’s a weirdly old-school thing for a kid to want, but I get it.

The Fart App Era Grows Up

Last year at SXSW, my take was that AI felt like the early iPhone App Store: experimentation, novelty, fart apps, nobody quite sure what the platform could really do. This year the panels and the parties had moved on. The question now is: now that everyone can build with AI, what actually lasts?

The creator economy tracks were saturated with this anxiety. Everyone is talking about authenticity. And I’ll be honest. I’m sick of the word. It’s started to sound… inauthentic. (How fitting). But underneath the buzzword is a real thing, which is that when AI commoditizes the tools and increasingly the content itself, what differentiates a creator is not what they made this week but the trail behind them. The point of view they’ve held over time. The takes they got right. The takes they got wrong and admitted to. The reps. The receipts.

Your audience isn’t buying the post. They’re buying you, and the only way they can do that is by looking at the trail.

WayMo Or Less

I took my first Waymo. Genuinely impressive. Quick tip: sit in the front. No awkward passenger energy, and you control the radio and the temperature.

The car won’t make u-turns. It won’t do 31 in a 30. It won’t cut through an alley even if it would obviously be faster. Which makes sense… you can’t program in “just do whatever makes sense” if you ever want any of these decisions to hold up in court. So maybe the machines are safer but not faster. Or maybe I lived in NYC for too long.

What was harder to accept were the unexplained moments. It dropped me off on the wrong side of a highway - twice - without saying a word. My hunch is that the car won’t drop you off next to your destination if there’s any hint of an illegal stop or blocking right-of-way, so it just… didn’t. It backed up at a red light to make room for a truck behind it, which is polite but genuinely alarming when you don’t see it coming and your stomach tells you the car is misbehaving.

The fix isn’t complicated, and it’s the same thing the CDs and the creator economy stuff is about: tell me what you’re doing and why. Give me the receipt in real time. The technology earned my respect on the first ride. It hasn’t quite earned my trust yet, and the gap between those two things is exactly the thing I’m trying to name. Waymo has the capability. What it’s not giving me is the receipt.

Trust, Built From Receipts

So that’s the thing I keep coming back to. Trust is real, but it’s the conclusion. Receipts are the mechanism. When the tools are cheap and everyone can produce the output, the differentiator is the evidence behind the output. The reasoning behind the take, the track record behind the brand, the explanation behind the decision the robot just made.

I think this is a useful frame for anyone building right now, because it tells you where to invest. Not in more capability - that’s a commodity - but in the trail. The receipts. The stuff that takes time and can’t be faked, which is, conveniently, the stuff AI is worst at.

What’s your take?

In the meantime, here’s what a Waymo’s like from the driver’s POV.

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🎙 New Episode: How Donal Greene Beat $100M Startups (and Got Acquired on His Terms)

Most identity verification startups in 2022 were flush with VC cash... $200M raises weren’t uncommon. The standard playbook: raise big, spend fast, pray you don’t get hacked.

Donal Greene? He skipped all that.

Instead, he bootstrapped a tiny team, built a better product, got to $10K MRR, and then forced one of his competitor’s customers to acquire him.

This is not a case study in fundraising. It’s a playbook for building something better, faster and getting paid for it.

What stood out to me:

• MLP > MVP: Donal focused on building a “Minimum Lovable Product,” not just something that functioned. It worked: ID verification in 20 seconds, zero clicks, better fraud detection than the $100M giants.

• Domain expertise wins: What I thought was cool was that he constructed a team with 10+ years of biometric security experience. That edge made the product defensible and differentiated.

• He bootstrapped smarter: He focused on being fast, efficient, and good enough to close paying customers. That made it viable and visible to acquirers.

• Prospect your buyer: The wildest move? He identified a flaw in a competitor’s system, filmed a screen recording, and cold-DM’d a customer CEO. That CEO replied… with a Google Meet link. Weeks later, deal done, selling to Canada's Certn.

There’s a ton here for founders who don’t want to chase hype, and want to build on their own terms.

Donal doesn’t just tell the story of his exit; he demonstrates how to engineer your own.

🔊

Watch or listen: YouTube | Apple Podcasts | Spotify

Toronto Tech Week 2025: Recap & Thoughts

This past week marked the inaugural Toronto Tech Week, a grassroots response to years of fragmented ecosystem events and, notably, the recent loss of Collision to Vancouver. Modeled after other tech weeks around the world, it aimed to unify and energize the city’s tech scene.

So, how was it? I think the team did an admirable job.

Here’s the thing about most conferences: content quality varies, but the real action happens at the side events. Toronto Tech Week leaned into that insight. It was the side events, minus a central tentpole. The organizers told me on my livestream that they aimed for 10,000 attendees. If they hit that, they’re in the same ballpark as Web Summit Vancouver, which reported 15,727 this year. Not bad for a first outing.

And without a formal main event, there was still a ton of substance. We saw everything from packed mixers to conversations with some of Canadian tech’s sharpest minds. Brad Feld came to talk mentorship. Evan Solomon, now Canada’s new Minister of AI and Digital Innovation, came to listen. Netflix CTO Elizabeth Stone shared how they’re scaling and evolving (hot take: they want to be the next YouTube). A cohort of scaling entrepreneurs from Northern Ireland came to MaRS to explore North American markets. I even joined a panel with Dwayne Forde of Mantle at a founder matchmaking event hosted by YSpace and the Black Entrepreneurship Alliance.

In total? Over 300 events. Too many to name, but plenty to move the needle.

I’ve come to believe that culture drives everything in an innovation ecosystem. Government policy is downstream of culture. Risk-taking and entrepreneurship are, too. So is the instinct to rest on your laurels. And culture, as we all know, is the hardest thing to change.

By definition, events like this start by preaching to the choir. But this one had a glimmer of something more. A sense it might just be crossing the chasm into the broader fabric of Toronto.

Good thing crossing chasms is what tech entrepreneurs do best.

Upcoming Events

July 9-11: Startupfest in Montréal. We'll be doing a pop-up show on the event floor. Come by, say hi!

September 24-25: ALL IN, Canada's largest AI conference in Montréal, where I'll be hosting the All In Talks stage again.

🔊

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• How Donal built a “Minimum Lovable Product” instead of chasing MVP hype

• Why deep domain knowledge beat VC-funded noise

• What he learned replacing his founding team mid-build

• How a cold outreach turned into a full acquisition

• And what he’d do differently the next time around

This one’s for the builders who’d rather out-execute than out-raise.

📬 Tech entrepreneurship is changing fast. Join the conversation: https://decelerator.link/updates?ref=youtube

#podcast #interview #ai #startups #entrepreneur #entrepreneurship #technology #technews #artificialintelligence #innovation

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🎙 New Episode: Why Most Startup Ecosystems Aren't Ready for the AI Boom

At the inaugural Web Summit Vancouver 2025, I sat down with JF Gauthier, founder of Startup Genome, to unpack why ecosystems like those in Canada, Europe, and beyond are falling behind, and what cities like Philadelphia are getting right. They also just released their 2025 report.

So many things stuck out for me in our conversation including (and no, this is not a ChatGPT bullet list):

• the fact that startup ecosystem value has dropped 23% globally, its biggest drop ever, but ultimately still grows 4x faster than the rest of the economy

• In ecosystem land, Toronto fell from #13 to #20 and Vancouver from #15 to #36. OTOH, Tel Aviv, Singapore, Seoul all had government-seeded private scaling. And Philadelphia galvanized its ecosystem with no government help at all.

• JF also cited the example of DeepSeek and how the Valley-based companies acted on this innovation. They tested the new models with in days and shared their learning rapidly. He noted innovation velocity isn't just about capital - it's about ecosystem learning loops.

Just so much meat on the bone here...

Whether you're a founder, policymaker, or investor, this is your roadmap to staying relevant in the AI era.

🔊

Watch or listen: YouTube | Apple Podcasts | Spotify

Toronto Tech Week 2025: The Livestream Prep Tour

Watch the livestream, but not live!

Toronto Tech Week is coming up this week and one of the primary complaints I heard from friends and a few enemies is that the number of events was overwhelming and just tough to choose from and navigate. So I reached out to the organizers of the event and hosted a livestream this past week (our first 🙌🏻) to hear their perspectives on the event. If you're thinking of attending, have a listen!

Upcoming Events

June 23-27: Toronto Tech Week, we'll be out and about for its inaugural incarnation.

July 9-11: Startupfest in Montréal.

September 24-25: ALL IN, Canada's largest AI conference in Montréal, where I'll be hosting the All In Talks stage again.

🔊

Subscribe: YouTube | Apple Podcasts | Spotify

At the inaugural Web Summit Vancouver 2025, I sit down with JF Gauthier, founder of Startup Genome to unpack why ecosystems like those in Canada, Europe, and beyond are falling behind and what the top-performing cities are doing differently (like Philadelphia).

We dive deep into:

• Why AI is killing traditional SaaS

• How governments can seed ecosystems then get out of the way

• The real reason Canada's commercialization gap persists

• What investors should be doing in the AI-native era

• The new rules for building and scaling in 2025

Whether you're an entrepreneur, policymaker, or investor, this is your roadmap to staying relevant in the next wave of innovation.

🔗 Full Startup Genome report

📬 Tech entrepreneurship is changing fast. Join the conversation.

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New Episode: Ryan Henry on YC Spring 2025, Agents & Vibe Coding

Once again, I sat down with Ryan Henry of Sand Hill North, the sole VC at a family office to get his hot takes on the cutting edge startups he invests in. Why focus on the YCX25 batch for a show about building tech companies differently? Well, one is he does invest in the latest companies out of YC, and I'm fascinated by what shiny new AI tech shows up. And two, as a non-traditional investor, he doesn't have to deploy capital. He can do whatever makes sense for the fund whenever it makes sense.

So why check it out? This one gets into the weird tension of where we are right now: in between building tools and building coworkers. We cover:

• What “vibe coding” actually is (and why Ryan thinks I got it wrong)

• The early signals of agentic workflows taking over creative tasks

• What a good founder looks like in the age of AI

• Which traditional startup structures are breaking - and when those patterns don’t work, especially in enterprise or high-stakes domains

Check out the full episode - does this match what you're seeing and hearing?👇🏻

🔊

Latest Episode: YouTube | Apple Podcasts | Spotify

Web Summit Vancouver 2025

After Vegas, New Orleans, and Toronto, Web Summit's newest North American destination is now Vancouver. I do enjoy these conferences and this one was no exception. It was significantly smaller than the previous iterations (15k people vs 40k), but Vancouver is a smaller city and there were no shortage of things going on. Aside from hosting an event, I moderated a panel on Canada's innovation opportunity within the Vancity Innovation house (a side event that hoped to increase BC's impact in tech writ large), and even recorded a pod with the founder of the Startup Genome project.

For its freshman year, it was a good start. It certainly had a BC vibe and clearly rallied their tech ecosystem. The Web Summit team have clearly built a well oiled machine as well. What I'm looking forward to at future iterations - and I know this is tricky - is a more "global" feel. Yes there were countries and companies from around the world, but - and maybe it's just that I wasn't invited to the cool kids parties and stages - it felt Canadian. It's a global conference's North American edition, and I think it still has to grow back into that global stature. I know this is hard work and doesn't happen quickly, but IMHO that should be their north star for 2026 - feel more centre of the universe.

I'll be going back, excited to see the next iteration, and hope to see you there too.

Upcoming Events

June 23-27: Toronto Tech Week, we'll be out and about for its inaugural incarnation.

July 9-11: Startupfest in Montréal.

September 24-25: ALL IN, Canada's largest AI conference in Montréal, where I'll be hosting the All In Talks stage again.

🔊

Subscribe: YouTube | Apple Podcasts | Spotify

AI startups in 2025 are throwing out the roadmap. In this episode, investor Ryan Henry shares what he’s seeing at the frontier: agentic workflows, founder-led experimentation, and why traditional product roles are fading fast. We also revisit a debate about “vibe coding” - intuition-led building in a world of moving targets.

📍 Key Moments

• 00:00 - Introduction to Ryan Henry and his family office VC approach

• 02:40 - Ryan's fund structure: investing in other funds for deal flow

• 07:12 - Different return expectations compared to traditional VCs

• 18:30 - Debating "vibe coding": what it is and its implications

• 21:32 - The evolution of AI-assisted development capabilities

• 27:10 - Concerns about rapid prototyping vs. proper customer discovery

• 33:30 - Current YC trends: AI agents, robotics, and advanced manufacturing

• 41:55 - The state of AI agents today and what they can reliably do

• 47:38 - Building companies with anticipation of improving AI capabilities

⁠Subscribe to my newsletter here to stay up to date on the new startup world⁠!

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New Episode: Enron

At the Consensus 2025 conference in Toronto, I discovered something unexpected: Enron - yes that Enron - the infamous energy company that collapsed in 2001 is being revitalized with a mission to solve America's energy crisis.

Connor Gaydos, best known for creating the viral "Birds Aren't Real" movement, shares his vision for transforming the disgraced Enron brand into a trusted energy provider focused on transparency, community, and innovative solutions to fix the electrical grid.

Some highlights for me:

• Rebranding disaster into opportunity: Connor bought the Enron brand post-bankruptcy and is reviving it as a transparent, trustworthy energy company in Texas.

• Memes meet megawatts: Connor’s past with the viral “Birds Aren’t Real” meme taught him the power of community and storytelling. Now he’s using that same memetic savvy to build a loyal following around Enron’s mission.

• Solving the energy crisis with grit and tech: The plan? Start as a retail energy provider in Texas with a focus on cleantech - batteries that store excess solar and wind power for peak hours - and scale from there. There’s even a beta micro nuclear reactor (“The Egg”) (!) in the pipeline.

• Crypto complications, but not just for cash: Enron tried a token offering to get the community involved, but ran into shady liquidity providers manipulating the market. The lesson? Trust and transparency are the only currencies that matter for long-term success - something that resonates with me.

• Fighting monopolies with attention and authenticity: Texas’s deregulated energy market is ripe for disruption, but entrenched players don’t make it easy. Connor’s strategy? Use the Enron brand legacy to get people talking, demand better service, and force regulators to sit up and take notice.

Check out the full episode - I'd love to hear your take on this.👇🏻

🔊

Latest Episode: YouTube | Apple Podcasts | Spotify

Upcoming Events

Here's what's coming up, and do subscribe to our events calendar here.

May 27-30: Web Summit Vancouver, its inaugural conference in a new location. We'll be hosting a soirée - limited spots, check it out here.

June 23-27: Toronto Tech Week, where we'll have some announcements coming up soon.

July 9-11: Startupfest in Montréal.

September 24-25: ALL IN, Canada's largest AI conference in Montréal, where I'll be hosting the All In Talks stage again.

🔊

Subscribe: YouTube | Apple Podcasts | Spotify

Connor Gaydos, best known for creating the viral "Birds Aren't Real" movement, shares his vision for transforming the disgraced Enron brand into a trusted energy provider focused on transparency, community, and innovative solutions to fix the electrical grid.

With energy and Web3 investors, he shares his vision and journey to date, with a little bit of token malfeasance he discovered along the way.

0:00 - Consensus 2025 recap

3:01 - Meet Connor Gaydos, the new CEO of Enron

5:47 - Lessons learned from "Birds Aren't Real" and memetic marketing

8:46 - Enron's mission to fix America's energy crisis

11:12 - Innovative battery solutions to address peak energy demands

14:00 - How Web3 and community tokens fit into Enron's strategy

17:15 - Building trust with a historically distrusted brand

21:22 - The "Egg" - Enron's micro-nuclear reactor concept

24:28 - Taking on entrenched energy monopolies

29:46 - Building community through internship programs

31:31 - Lessons from cryptocurrency setbacks

33:34 - Enron's six-month roadmap to enter the Texas energy market

Connor explains how he's using memetic marketing to raise awareness about energy issues while building a legitimate business focused on battery storage, retail energy provision, and eventually micro-nuclear technology.

By attracting attention through the infamous Enron brand, he hopes to challenge the status quo in an industry that has lacked innovation and customer focus.

#startup #founder #entrepreneur #entrepreneurship #web3 #podcast

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New Episode: Austria!

This week, I had the pleasure of talking with Markus Raunig from AustrianStartups about all things European tech, and Austria in particular.

Here’s what Markus shared about the European and Austrian startup scene, and why you may want to take a closer watch / listen:

• Europe’s tech narrative is changing. For years, the meme was: America innovates, China duplicates, Europe regulates. But with fresh EU initiatives like the "one company" legal framework—essentially creating a virtual 28th state to simplify cross-border startups—Europe is pushing to attract top talent and compete on a global scale.

• Austrian startups thrive on stability and quality of life. Vienna has been named the most livable city in the world multiple times, combining affordable living with excellent infrastructure and access to talent from both Western and Eastern Europe. This unique geographic and cultural crossroads gives startups one of the best bases for European scaling.

• Entrepreneurship needs to be a mindset cultivated early. Markus draws a parallel to how Austria created a ski culture by teaching every child to ski. Now the focus is on early entrepreneurial education — giving young people the tools and mindset to take risks confidently, supported by a robust social safety net that empowers rather than encourages complacency.

• Austria balances social safety with economic dynamism. There’s a strong social safety net that allows risk-taking without the fear of losing everything. However, this can also breed complacency. The real work is in activating people to use that safety net as a launchpad to pilot their own ventures rather than stay passengers in life.

Check out the full episode for a deeper dive into Austria’s ecosystem, Europe’s startup ambitions, and the tradeoffs that are made. 👇🏻

🔊

Latest Episode: YouTube | Apple Podcasts | Spotify

NACO Summit 2025

Last week I moderated a couple of panels at the NACO (National Angel Capital Organization) Summit in Ottawa, Canada the day after the election. The energy was palpable as it's obvious Canada itself is at an inflection point where Canadians have to the opportunity to choose their destiny and have unprecedented power to do so. Whether this time's the charm remains to be seen, but the innovation ecosystem is clearly ready to step up and make that change. How remains the billion dollar question.

Upcoming Events

Here's what's coming up, and do subscribe to our events calendar here.

May 15-16: The OOO Summit in NYC, created by events magnate Andrew Yeung.

May 27-30: Web Summit Vancouver, its inaugural conference in a new location. We'll be hosting a soirée - limited spots, check it out here.

June 23-27: Toronto Tech Week, where we'll have some announcements coming up soon.

July 9-11: Startupfest in Montréal.

September 24-25: ALL IN, Canada's largest AI conference in Montréal, where I'll be hosting the All In Talks stage again.

🔊

Subscribe: YouTube | Apple Podcasts | Spotify

Subscribe: Apple Podcasts | Spotify | YouTube

SXSW

I promised all the SXSW things, so here they are. This week's episode was filmed there and I even guested on another podcast (see below), so if you feel like you've missed it, well... this will be as close to going as possible.

New Episode: 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. And no, ChatGPT did not use those hyphens, I did.

I spoke with Breen Sullivan, founder of The Fourth Effect, at SXSW 2025. The Fourth Effect is revolutionizing how startups and experienced executives connect.

She delves into:

• Why most startups are missing out on a goldmine of expertise and growth potential

• The surprising way corporate executives can break into the startup world (and why they should)

• How to build a board that actually adds value (hint: it's not just about big names)

• The strategic moves that can help founders maintain control as they scale

If you’re a founder looking to build strategic advisory relationships, or an executive wanting to break into the board ecosystem, this episode offers invaluable insights on maximizing these relationships for mutual benefit.

Ready to level up your board game (cough)? Check out the episode below 👇🏻

🔊

Latest Episode: Apple Podcasts | Spotify | YouTube

Bonus: SXSW Pod Appearance - CRAFTED

I ended up meeting Dan Blumberg, host of the CRAFTED podcast, where he sat down with me and we traded some post-conference thoughts and I shared:

• my theory that we’re in AI’s “fart app” era

• why AI itself is already commoditized

• the state on a B2B creator right now based on what we learned at the conference

CRAFTED.Dan Blumberg

Upcoming Events

Here's what's coming up, and do subscribe to our events calendar here.

April 29-30: NACO's Summit in Ottawa, the National Angel Capital Organization's annual gathering, where I'll be doing an on-stage interview.

May 27-30: Web Summit Vancouver, its inaugural conference in a new location. We'll be hosting a soirée - limited spots, check it out here.

June 23-27: Toronto Tech Week, where we'll have some announcements coming up soon.

July 9-11: Startupfest in Montréal.

September 24-25: ALL IN, Canada's largest AI conference in Montréal, where I'll be hosting the All In Talks stage again.

🔊

Subscribe: Apple Podcasts | Spotify | YouTube

Check us out: Apple Podcasts | Spotify | YouTube

But First, A Note

What a time to be alive. It's been a while, so there's lots to catch you up on! Went on a revelatory trip to SXSW, which included recording not one but two shows, supporting a startup pitch winner, Xatoms, and eating a lot of BBQ. But that's for the next episode.

FreightSimple

Freight logistics quietly powers our economy - until it breaks. FreightSimple is a B2B logistics company that solves these shipping problems. To that end, we recorded this episode before the trade war started in earnest, so perhaps I need to have Natasha Ross, the cofounder, on weekly to follow the twists and turns in her business.

The business may seem dry - spoiler alert: that's the point - but it ain't. We covered the typical startup stuff (problem, solution, etc.), but Natasha was unusually candid about how she looks at her business. Her cofounder exited to Apple previously, which creates an interesting dynamic. I asked her whether she was shooting for an acquisition or how did she define success, and she answered thoughtfully.

I also felt the need in the monologue to talk about enshittification and where I think it will show up next.

In this episode we cover:

• The absurdity of freight logistics: "You'd email or call around, hoping someone replies before your shipment misses the truck."

• The startup reality check: "Initially, the market was allergic to tech; now they can't get enough."

• Natasha’s best lesson: "Solve the boring stuff—complexity hides opportunity."

• How to earn an industry's trust and Natasha's advice for entrepreneurs.

Let me know what you think!

• Listen to this episode on Apple Podcasts

• Listen to this episode on Spotify

• Share on LinkedIn

• Share via email

• Share on Reddit

• Share on Facebook

• Share on X

Upcoming Events

Here's what's coming up, and do subscribe to our events calendar here.

April 29-30: NACO's Summit in Ottawa, the National Angel Capital Organization's annual gathering, where I'll be doing an on-stage interview.

May 27-30: Web Summit Vancouver, its inaugural conference in a new location.

July 9-11: Startupfest in Montréal.

September 24-25: ALL IN, Canada's largest AI conference in Montréal, where I'll be hosting the All In Talks stage again.

🔊

Check us out: Apple Podcasts | Spotify | YouTube

The business may seem dry - spoiler alert: that's the point - but it ain't. We covered the typical startup stuff (problem, solution, etc.), but Natasha was unusually candid about how she looks at her business. Her cofounder exited to Apple previously, which creates an interesting dynamic. I asked her whether she was shooting for an acquisition or how did she define success, and she answered thoughtfully.

I also felt the need in the monologue to talk about enshittification and where I think it will show up next.

In this episode we cover:

• The absurdity of freight logistics: "You'd email or call around, hoping someone replies before your shipment misses the truck."

• The startup reality check: "Initially, the market was allergic to tech; now they can't get enough."

• Natasha’s best lesson: "Solve the boring stuff—complexity hides opportunity."

• How to earn an industry's trust and Natasha's advice for entrepreneurs.

00:02:00 – Interview begins: Natasha Ross from FreightSimple

00:08:30 – Life before FreightSimple: struggles with manual logistics

00:14:52 – Empowering businesses to simplify freight decisions

00:22:37 – Why solving logistics problems is uniquely rewarding

00:29:34 – Behind-the-scenes: automating freight bookings

00:37:08 – Eliminating costly mistakes in shipping logistics

00:46:12 – Overcoming startup challenges in resistant industries

00:54:26 – Gaining industry trust: lessons from FreightSimple’s growth

01:02:10 – Natasha’s advice for entrepreneurs navigating complex industries

01:00 - A family office VC’s AI perspective 04:30 - AI startups: How investors really think 08:45 - AI as a business: Feature vs. product 12:20 - How AI models actually work and think 18:10 - The business models of AI and OpenAI’s strategy 24:00 - Startups vs. incumbents: How to win in the AI era 30:15 - DeepSeek’s role and where it fits in 35:40 - AI's real economic moats 40:25 - What’s next for AI startups?

AI is moving fast, but do you really understand how it works, how to think of relevant business models, and what the heck just happened with DeepSeek last week? What the heck is an AI startup anyway?

In this episode, I sit down with Ryan Henry, a venture capitalist with deep AI expertise and who actively invests almost exclusively in AI startups, to go beyond the headlines and get into the real mechanics of AI. We discuss how these models actually work, the business models shaping them, and most importantly, how startups can win in this new, rapidly changing AI-driven world.

We cover:
✅ How AI really “thinks” and what that means for businesses
✅ If AI startups were just "wrappers" for the core 🥇winning🥇 business model of the models themselves, did the models just get ... wrappered? Is that a word?
✅ The real economic moats in AI (hint: it’s not just GPUs)
✅ Where DeepSeek fits into the AI wars and why it matters
✅ How entrepreneurs can leverage AI without being wiped out by incumbents

If you’re building, investing, or even just thinking about AI (or AI is thinking about you), this episode will give you the frameworks and insights you won’t get from a superficial news story.

❓ Would love to hear your thoughts! Did we capture your perspective? Were we entirely wrong? Let me know!

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Upcoming Events

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February 13: Koru's - OTPP's venture studio - 5th anniversary party.

March 7-12: We'll be at the SXSW, so be there or be square.

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