One of the best parts of building Future Proof Citywide is listening to people who are shaping the next era of wealth and investment management. There’s no shortage of opinions about AI, but every so often, someone frames the change in a way that makes you think deeper.
That’s what happened in a recent discussion with Jason Pereira, Senior Partner and Financial Planner at Woodgate Financial an independent Canadian wealth management firm.
I often describe Jason as the Canadian Michael Kitces for his ability to break down the most technical parts of our industry into plain English. In true Canadian form, he always smiles and politely reminds me that Michael Kitces is actually the American version of Jason Pereira.
To Jason, AI is a test of how quickly people can evolve. Here are five lessons that stood out from our conversation.
1. Pilots Are Supposed to Fail
When the MIT study came out showing that 95% of corporate AI projects produced limited productivity gains, Jason and I agreed: that was to be expected. That’s how learning happens.
Early pilots are designed to fail, to expose the gaps in data, process, and understanding. The real issue isn’t that firms didn’t get results; it’s that too many mistook experimentation for execution. Announcing an “AI strategy” before knowing what problem to solve or who’s accountable for it is why so much progress looks like failure from the outside.
The lesson: failure in early AI adoption shouldn’t be viewed as a waste, it’s feedback.
2. Technology Isn’t the Problem, People Are
Jason’s core argument is blunt but true: humans don’t change, our toys do.
Every wave of technology – desktop, mobile, cloud – followed the same curve: hype, resistance, and slow adoption. AI is no different. The challenge isn’t the capability; it’s the culture. Until firms align incentives, structures, and education around these tools, the technology will always run ahead of the people using it.
3. Smart Firms Are Building for Stewardship, Not Optics
The firms getting it right are preparing foundations. Jason calls it data stewardship:
- Is your data clean and organized?
- Do your systems actually talk to each other?
That’s what smart acquirers are now looking for in M&A due diligence. “What’s your AI strategy?” has become as important as AUM or client demographics. As he puts it, “The more work I have to do after I buy you, guess what? That line item and that opportunity cost just came off your price.”
4. AI Is Empowering a New Kind of Builder Advisor
One of the aspects Jason was most excited about was vibe coding, describing a problem in plain language and having AI generate working code in minutes.
That ability is democratizing innovation inside firms. Advisors who used to rely on tech teams can now create simple, tailored tools on their own. A 60-year-old non-technical advisor with decades of experience can design a workflow app that solves a client pain point, without writing a line of code.
As Jason puts it, “Write down the thing you need to solve the problem, put that into the machine and see what comes out. Just try that and then go from there and you will be marveled by what’s possible.”
5. The Real Return on AI Is Time
When AI actually delivers efficiency, the question becomes: what do we do with the time we get back?
Jason sees three options. We can serve more clients, though that risks thinning the human connection that defines great advice. We can work less, if balance is the goal. Or we can go broader and deeper, using that time to deliver more value.
If AI gives us back time, we have to decide how to use it: to learn faster, collaborate more openly, and build systems that lift the entire profession.
Looking Ahead to Future Proof Citywide
The real advantage in this new era will come from community. The firms that share openly, learn from one another, and build together will move faster and further than those who go it alone. That’s what Future Proof Citywide is built to do: unite the leaders, builders, and innovators shaping how AI will redefine the future of wealth management.
Don’t miss your chance to educate yourself and your firm, and experiment alongside industry leaders, inside our all-new AI Playground, a 21,000-square-foot pavilion packed with live demos, startup showcases, peer-to-peer discussions, and hands-on learning zones.
Register now to join the movement transforming how wealth management learns, builds, and grows in the age of AI.
Author
Matt Middleton
Founder & CEO, Future Proof
Matt Middleton is the founder and CEO of Future Proof, the company behind the world’s largest AI-native finance event, Future Proof Citywide. He leads the vision for building community-driven experiences that connect the most forward-thinking investors, advisors, technologists, and creators redefining financial services.
Disclaimer: This article was written by me … with the help of AI (ChatGPT 5 to be specific). If we’re building an event about how AI is transforming finance, we’d be hypocrites not to use it ourselves. At Future Proof, we’re testing and deploying AI at every stage of the business: from how we research and write, to how we design, plan, and deliver events. Consider this both an experiment and a preview of what’s to come.
