From the Wattpad Office to Ada’s Next Chapter Congratulations to Mike Murchison, David Hariri, and the entire Ada team on the combination with Dialpad! Here’s a little backstory about how it all started. Back in 2015, Mike was working on a startup called Volley that wasn’t going well. Before shutting it down, he had another idea: what if AI could answer customer-support emails? Wattpad was one of the largest consumer internet companies in Canada, so naturally we handled a large volume of support tickets. I’d known Mike for years, so he started coming into our office a couple of times a week to build and test his new product. I watched the prototype evolve firsthand. Initially, it barely worked. But gradually, it started answering real customer questions, and the results kept getting better. Wattpad became Volley’s first paying customer, and Two Small Fish Ventures became its first investor after the pivot. Volley was subsequently renamed Ada. The rest is history. Of course, building a startup is never a straight line. Over the next decade, Mike and his team navigated countless challenges and built something of tremendous value. And Wattpad remained an Ada customer even after I stepped aside from the company. I’m glad that Wattpad and Two Small Fish Ventures played a part in Ada’s early days. From a prototype that barely worked in the Wattpad office to this milestone. What a journey! Congratulations again, Mike and team! Wishing everyone at Ada and Dialpad tremendous success in this exciting next chapter. Globe and Mail report: https://www.theglobeandmail.com/business/article-ada-toronto-ai-chatbot-firm-dialpad-merger/ The post From the Wattpad Office to Ada’s Next Chapter appeared first on Allen's Thoughts.... https://allensthoughts.com/2026/11/04/from-the-wattpad-office-to-adas-next-chapter/ #rss #feeds #linksharing #qwibbit

Why We Don’t Invest in Competing Startups Historically, one of the golden rules of venture capital has been not to invest in competing startups. But AI is beginning to challenge that convention. Even the storied Silicon Valley VC firm Benchmark is finding it increasingly difficult to avoid conflicts between portfolio companies. As AI makes software easier to build, startups are expanding into each other’s markets faster than ever. Companies that weren’t competitors yesterday could become competitors tomorrow. I was particularly surprised by a comment from Benchmark partner Eric Vishria who told TechCrunch: “We are not product or technology experts.” That statement helped crystallize why we take a different approach at Two Small Fish Ventures. Our expertise is our edge One of our first principles is that we only invest in areas we understand deeply, both technically and operationally. Our entire investment team has technical backgrounds and hands-on operating experience spanning software, hardware, product development, commercialization, and company building. We love working closely with founders, helping them think through technical challenges, product strategies, commercialization, hiring, and company-building decisions. That’s a big part of the value we bring beyond capital. Capital is a commodity, and great companies look for more than capital from their investors. Our technical and operating expertise is how we differentiate ourselves and attract the best founders and companies. We want founders to choose us not just for our capital, but for the value we can bring to their journey. That level of involvement requires trust To provide meaningful help with technology, product strategy, and commercialization, founders need to share information they wouldn’t necessarily share with other investors. Financial updates and board materials alone aren’t nearly sufficient for the kind of hands-on support we provide. We need to understand the difficult problems founders are wrestling with, where their technology is struggling, what they haven’t figured out about their product, what challenges they face operationally and which strategic options they’re considering. That kind of openness requires trust. Imagine we invested in two companies competing for the same customers, developing similar technologies, or pursuing the same opportunities. Even if we maintained perfect confidentiality, the perception of a conflict would be difficult to eliminate. Once founders begin wondering what they can safely share with us, they’ll naturally share less, eroding the very value we’re trying to provide in the first place. Different investors, different models Venture firms don’t necessarily need to operate the same way. Some investors focus primarily on capital allocation, while others are deeply involved in company building. Many fall somewhere in between. For us, particularly in early-stage deep tech, simply providing capital isn’t sufficient. Without deeply understanding how the technology works, how the product should evolve, and how commercialization might unfold, it’s difficult to provide the kind of support that helps founders make the most of their capital. That’s the approach we’ve chosen, and it’s why founder trust is so important to us. Of course, this becomes more complicated as companies evolve. Two startups that aren’t competitors when we invest might eventually move into overlapping markets, especially as AI makes those boundaries more fluid. But by being thoughtful about potential overlap from the beginning and having open conversations with founders at the time of investment, we can minimize the risk of future conflicts. We can’t eliminate every possibility of overlap, but we can be deliberate about the decisions within our control. Ultimately, our reputation is worth far more than any single investment opportunity. We don’t want to compromise the trust we’ve built with our founders, and knowingly investing in companies that already compete is a conflict we can simply avoid. Our edge demands boundaries Our competitive advantage comes from deep technical understanding, operating experience, and hands-on involvement with founders. We don’t want to dilute that edge. We want to protect the reputation and trust that make it possible. If being deeply hands-on is our superpower, protecting founder trust is non-negotiable. That’s why we don’t invest in competing startups. The post Why We Don’t Invest in Competing Startups appeared first on Allen's Thoughts.... https://allensthoughts.com/2026/10/28/why-we-dont-invest-in-competing-startups/ #rss #feeds #linksharing #qwibbit