With Toronto Tech Week still fresh in mind, I am reflecting on the events I attended and what made some stand out more than others.
Here are some of my thoughts:
Careful curation of attendees is super powerful as it helps gather people with similar interests in the same room and spark great discussions. I witnessed events that did this very well and those events were much more valuable for me to attend.
Many events allowed you to work out while networking which is a great habit stacking if you enjoy both things. I found myself joining 2 founders runs throughout the week and had a memorable time. From the other events I saw on offer there was something for everyone from pilates to paddle.
I also enjoyed events that promoted discussion and sharing rather than just passively listening to a lineup of speakers demo their products. For example, one event hosted a science fair where product builders could demo their product in a room between the main presentations, where attendees could approach the tables with the products they want to interact with.
In one of the newsletters I follow there is this quote. What do you think about it?
Chatbots comply with the user s wish to solve the problem on their own, even when this is impossible and may make matters worse. Chatbots, in fact, are not built to help, but to please. If you feel flattered when your LLM tells you how smart your question was (I certainly do), you are not alone: a pre-print from 2025 found that all major LLMs were highly sycophantic.
I ve been looking at different smart-home setups and one thing I keep coming back to is how much of the system should depend on the cloud.
Cloud-based platforms are convenient because they make remote access and setup relatively simple, but local control seems appealing for reliability and response time. If the internet connection goes down, I d still want basic things such as lights, switches and sensors to work normally.
Two of my blog posts flipped from "Submitted and indexed" to "Crawled, currently not indexed" this week. No edits, no redirects, nothing changed on my end.
I went through everything GSC actually exposes: robots meta says index,follow, the canonical points to itself, HTTP status is 200. Technically clean by every check available. Google indexed them once, then quietly pulled them back out, with no error and no explanation anywhere in Search Console.
Every outbound tool now claims it can write emails that sound handwritten. Scrape a LinkedIn profile, pull recent posts, mention a specific detail, and the email reads like a real person spent five minutes on it. Reply rates on individual campaigns can look great for a while. But inboxes across the internet are filling up with the exact same pattern of "I saw you posted about X" openers, and spam filters are getting better at catching bulk sends that mimic personal writing.
I ran outreach fully manual for a while before building any automation around it. No AI, no templates copied across contacts, just reading each person's profile and writing something specific to them. That got a reply rate around 25%, which is high for cold email by most benchmarks. When I started automating parts of it to scale past what one person can write by hand, the reply rate didn't hold. Not because the automation was bad, but because the moment personalization becomes systematic, it starts pattern-matching to every other automated email a prospect has already seen that week.
I try really hard to be the kind of founder that listens to users. The whole idea of building something people want is that you're supposed to be paying attention to them, not building in a vacuum.
But every time I've followed the loudest requests, I've ended up building things almost nobody else wanted. One vocal customer asks for a feature, it feels urgent because they're right in front of me, and three weeks later it's sitting there barely used.
Genuinely trying to understand this before we launch something later this year. Every founder story says we launched on PH and got X users, but for every one of those there are probably a hundred launches that got 40 upvotes and disappeared by evening.
Curious what actually separates the two outcomes. Is it mostly about hunter reputation and launch-day coordination (rallying your own network to upvote early) or does the product genuinely need to be compelling enough to travel on its own once real strangers see it?
