The smartest founders I know are quietly losing sleep over a new question. Not how brands rank on Google, but how they sound when the machine speaks back. When a buyer asks ChatGPT who to trust, who...
The smartest founders I know are quietly losing sleep over a new question. Not how brands rank on Google, but how they sound when the machine speaks back. When a buyer asks ChatGPT who to trust, who gets named and who gets ghosted. That tension is where Yolando was born, not in a lab, but inside a business watching demand behavior change in real time.
Yolando is a Toronto based competitive intelligence and Generative Engine Optimization platform built to answer a blunt question. When AI becomes the front door, who does it let in. Founder and CEO Matt Bogoroch saw this firsthand running BirdseyePost as buyers started showing up informed by LLMs instead of landing pages. The data was there, the control was not, so the team built their own system and then realized it needed to stand on its own.
The company officially launched commercially in late January 2026 with $5 million USD dedicated to Yolando as a spin out, backed by Drive Capital. The headline number reads $8.5 million USD in cumulative funding, which reflects Drive Capital’s total commitment across BirdseyePost and Yolando. Precision matters here because this is not hype math, it is disciplined capital following real usage.
The founding trio tells you a lot about how this company thinks. Matt Bogoroch as CEO, Adam Bogoroch as COO, and Shardul Frey as CTO. Two brothers and a former KPMG cubicle mate who learned early how enterprise data actually breaks. Forbes 30 Under 30 credentials aside, the real edge is that Yolando is pressure tested daily inside BirdseyePost, not theorized on a slide.
Yolando watches how brands appear across ChatGPT, Claude, Perplexity, Gemini, and other generative engines, then tells teams exactly what to do about it. Not dashboards for sport, but actions that close the gap. Its proprietary model is trained to understand why LLMs cite what they cite, and why recycled content gets ignored. Shardul Frey has been blunt about that problem, and the architecture reflects it.
The platform runs more than forty specialized agents across research, competitive monitoring, accuracy validation, formatting, and execution. That is how teams move from insight to publishable briefs in minutes instead of weeks. Early signals matter here. Leads attributed to ChatGPT have shown higher revenue value and faster close cycles inside the BirdseyePost ecosystem, turning curiosity into pipeline.
Drive Capital does not chase noise, especially outside Silicon Valley. Founded by Mark Kvamme and Chris Olsen, with Masha Khusid deeply involved at the platform level, the firm’s bet here is not on a buzzword but on timing. As AI answers replace search results, visibility becomes currency, and Yolando is building the exchange.