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Steve Lockshin on the power of being independent

“You have to be a little crazy to start your own business. Seventy percent of businesses fail, and you have to believe you’re in that 30%.”

—Steve Lockshin 

Steve Lockshin has always hated running.

The veteran financial advisor and entrepreneur has never been one to find joy in a morning jog. But early in his career, Steve found himself rising early to head out on hour-long runs with Bob Levy, a trailblazer in financial technology and one of the most influential people in Steve’s storied career.

For five hours every week, Steve would reluctantly tie up his sneakers and head out for a run with Levy where he’d hold forth on everything from proper asset allocation to the secrets of manager selection. Lockshin’s love for running never blossomed, but he knew the lessons he was learning would have a profound impact on his career, so he kept at it: one foot in front of the other while a titan of finance dispensed sage advice between breaths. 

That advice has paid dividends for Steve throughout his career, especially as he built several businesses from the ground up. After cutting his teeth in the insurance industry, Steve had the opportunity to set up a family office for one of his clients and found success after going to one of his mentors and asking for help. That success helped Steve launch his first company in the early 1990s, the wealth management and consulting practice CMS Financial Services. The company eventually grew to more than $1 billion in AUM before the decade was out, leading to the firm’s acquisition by Convergent Wealth Advisors in 2001. 

CMS eventually became Fortigent, and Steve’s star as a wealth advisor and RIA continued to rise. Fortigent grew to one of the industry’s largest wealth advisory firms, focusing on working with the complex issues facing ultra-high-net-worth individuals and building trust with A-list clients. Steve was recognized as the country’s Top Independent Financial Advisor by Barron’s in 2011, an award that honored nearly two decades of hard work. 

But it hasn’t all been high-profile clients and shiny awards. Steve remembers times when he couldn’t make payroll and couldn’t afford to pay himself. At Advice Period, the tech-driven RIA he started in 2014, he didn’t take home a check for three years, a challenging period that paid off when Advice Period started racking up commendations and clientele.   

His advice for those starting out is straightforward: Be true to yourself and find your voice. It’s a fundamental credo that can be challenging for younger advisors to embrace, but Steve figured out a long time ago that if you don’t believe in yourself, then neither will your clients. 

He points to a moment early in his career where he found himself nervous and self-conscious about pitching to high-profile clients. He was, in his words, “petrified of screwing up.” But when he realized that he was the expert in the room, that pressure was lifted. You have to be confident that you know what you’re doing while retaining the humility to say, “I don’t know, but I’ll find out.”

The Road to One Hundred Million

It’s a simple secret, but that philosophy has followed Steve throughout his career, even as he’s changed his perspectives on different investment vehicles and the state of the industry. Conviction is one of the most important tools an advisor can have, and it’s helped him build, grow, and prosper over the course of his career.  

His newest venture, Vanilla, is putting that philosophy to practice in a new industry: estate planning. It’s a corner of advisory services that has lagged behind as the industry has embraced technology platforms, and Steve’s successful track record as an entrepreneur bodes well for the 2-year-old startup. He wants to equip advisors with the same set of tools for estate planning as they have for other aspects of wealth management, unlocking what he’s called the “last frontier of advisor technology.”  

Steve’s career is a story of adaptation and perseverance, and the bonds he’s built with his clients mean that they trust him even when, as he says, he “changed religions” on investment strategies. Being true to yourself and speaking honestly about evolving perspectives is something he attempts to pass on to those he’s mentoring. The hour-long jogs with mentors are (thankfully) in the rearview mirror, but the decades-long dedication to learning, growing, and thriving is here to stay. 

About The Human Advisor

This podcast is dedicated to changing the conversation from how big a financial advisor’s book of business is to how well they take care of their clients and actually help people. There’s a new breed of modern advisors who want to make a difference and do something meaningful. And in our series, we’re telling their stories.




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