We use this conversation to unpack the launch of the Insight Innovation Ventures fund, why it grew out of years of running the Insight Innovation Competition, and how we plan to support founders who are building at the intersection of research, analytics, and applied AI. Steve shares the entrepreneurial journey that led him from Zappi to CEOfriend, an AI‑powered advisory platform that gives founders and SME CEOs an always‑on “virtual board” of specialist advisors across finance, investment, entrepreneurship, competitive intelligence, market trends, leadership, and go‑to‑market strategy.

A big part of the discussion is the problem CEOfriend is trying to solve: most early‑stage CEOs cannot afford a world‑class board, yet they still need informed, context‑aware advice on everything from P&Ls and board packs to pricing, org design, and fundraising. CEOfriend’s agents are built on multiple large language models, wrapped in secure infrastructure that keeps company data outside the models while allowing the system to learn from each interaction and act more like a proactive human advisor than a generic chatbot. We also explore the roadmap ahead, from live AI “board meetings” between agents to the potential for domain experts to scale their impact by encoding their expertise into specialized agents.

As part of launching the IIV Fund and our collaboration with CEOfriend, we’ve arranged a special offer for the Insight Innovation Ventures community. If you want to try CEOfriend for your own business, use the coupon code LENNY when you sign up via CEOfriend to unlock our early‑stage partner discount.

Watch or listen to the full conversation to hear more about why we’re building Insight Innovation Ventures, how CEOfriend works in practice, and what this all might mean for the future of entrepreneurship in the insights and innovation space.

You can also check out Steve demoing CEOfriend here: