Attending two of the wealth management industry’s biggest gatherings in back-to-back weeks – Future Proof Festival and Osaic ConnectED – I had a rare window into both the evolution of financial advice and the people driving it forward. Across two very different formats – a high-energy corporate conference in Texas and a beachside festival in California – I had the chance to sit down with some of the industry’s most thoughtful leaders. Each conversation reminded me that beneath the data, technology, and consolidation, this business remains deeply human.
The Future Proof Festival in Huntington Beach set the tone. Instead of hotel ballrooms, panels unfolded on an open boardwalk beside the Pacific Ocean. Founder and CEO Matt Middleton told me his goal was to reinvent what a financial conference could be. “We’re all introverted in some way,” he said. But this location, with the right technology, and removing all the friction “allows [advisors] to actually engage on site.” Even after losing millions on his first event in 2022, Middleton stayed committed to building a model rooted in genuine relationships, not transactions. “You never bet against humans,” he said.
That theme of human connection came to life in my conversations with Julie Penwell of Wealthspire and Sofia Massie, founder of LionShares. Penwell, one of InvestmentNews’ Next Gen Advisors of the Year, spoke passionately about using social media and webinars to expand access to financial literacy. “The content is innovative,” she told me, “but what brings me back to Future Proof is the people.” Massie, a former quant trader turned ETF founder, described launching her first fund to minimize dividend taxes – an unconventional idea she pursued despite early doubts. “Eventually I said, I’ve got to make this a reality,” she told me. Both women represented the next generation Middleton was talking about: creative, fearless, and determined to make financial advice more accessible.
A week later, the focus shifted inland to Osaic ConnectED, where the conversation turned from connection to transformation. CEO Jamie Price opened the conference with a challenge to advisors to embrace the pace of change. “This is an amazing business to be in,” he told me. “You’re helping people do things that without you they could never accomplish.” He spoke about the “Fourth Industrial Revolution,” where artificial intelligence, digital platforms, and cloud computing are reshaping how advisors work – ultimately freeing them to focus more on clients.
That drive for reinvention was echoed by Greg Cornick, Osaic’s EVP of Wealth Management Solutions. Having helped unify Osaic’s multiple broker-dealers into one platform, he compared the process to athletic training: “You did the blood, sweat and tears, and now you get to see how well you’re going to race.” Cornick’s energy mirrored the optimism I felt throughout both conferences.
I couldn’t help but see the same message shining through both events – whether on a windswept boardwalk or in a packed ballroom: technology may transform the tools, but people will always be the heart of wealth management.
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