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How is it going with Olivya?That’s the question many industry peers have been asking me lately. While answering it, I couldn’t help but feel a sense of disappointment—with myself more than anything. But I knew I had to be honest about where I stood in my entrepreneurial journey and where I truly wanted to invest my energy. And that energy wasn’t in building a scalable AI/tech company.We built Olivya in just three months and three months of research and testing. Here’s a snapshot of what we created during this process: Olivya V2 (Sept 2024)Alongside my partner, Marko Kecman, we’re happy to share our key insights—both about the product and the market—for anyone who might want to continue the quest of building the perfect AI human companion… #1 The AI App Challenge: Another Habit-App ChallengeIn the rapidly growing world of AI […]

I often get puzzled about high valuations. Sure, the market sets the price. If the founder is in a hot market with many investors wanting to lead the deal, founders often lean towards the fund that can give the biggest valuation. Here's an example I witnessed myself: A founder had a term sheet for 2M at 10M from one of the best VCs in their sector, but then they got a 2.5M at 15M offer from a bigger fund, and the founders went with this offer. They could have raised 2.5M at 10.5M and gotten the industry favorite VC, but they optimized for lower dilution. As a founder myself for almost two decades and now as a startup investor for over five years, I feel that founders don't appreciate all the issues that come from raising their first institutional investor […]

My partner at F4 Fund, David Kaye, wrote about the future of AI earlier this year in his piece, "How will we touch the robots?"I want to share my thoughts on investing in AI companion, tutor, mentor, etc. companies. Here’s a list of challenges and opportunities to go beyond the initial “wow” factor, which current products excel at but often fail to sustain.Challenge: ChatGPT already a mentor and companionHere's my prediction: The LLMs keep maturing and advancing, probably to the point where an OpenAI product can do many of the things that a consumer AI app would do right now. Eventually, the companionship that LLMs provide will become commoditized to the point where your virtual buddy on your mobile screen is just a flashy interface.Another challenge: Flashy interface and long term user retentionYou could argue that a flashy interface has […]