Two years ago, when Ajay Gupta left UBS to start his own independent wealth management firm in San Diego, he wasn’t sure if anyone was coming with him.

But it wasn’t the first time Gupta took a risk in stepping out on his own: Fifteen years ago, he transitioned his advisory practice in Canada to start anew in San Diego. Today, he is CEO and CIO of Gupta Wealth Management, an RIA that recently surpassed $1 billion in assets under management.

Gupta, 44, has also received attention for his high-profile clientele, who include self-help gurus Deepak Chopra and Tony Robbins. Gupta Wealth Management serves high-net-worth and ultra-high-net-worth families, endowments and foundations nationwide.

“All of our clients are high net worth,” Gupta says. “Many of them have substantial assets with us. We have a lot of accounts between $2 million and $20 million.”

Last year, Robbins included Gupta’s experience in his book Money: Master The Game: 7 Simple Steps to Financial Freedom.

“He’s spent hundreds of hours talking about my perspective on the industry,” Gupta says. “The people who read it were curious—they were accustomed to the brokerage model—and we’ve received a lot of inquiries since the book was published.”

The exposure has fueled the growth of Gupta Wealth Management and has raised Gupta’s profile within the industry.

But his success and ambition are guarded by his humility. The Canadian son of an Indian immigrant, Gupta is a second-generation financial advisor.

“My father inspired me to take care of others, as he did for myself and my siblings,” Gupta says. “I began exploring the realm of finance at a young age, and have been learning ever since.”

After studying at Concordia University and completing the Wharton School's advanced training program for the CIMA designation, then interning with his father, he began working in the industry, first taking a job as a broker and advisor with Midland Walwyn, which was later purchased by Merrill Lynch. In 2000, he moved his practice to San Diego.

Gupta broke away from Merrill Lynch to join UBS in 2008, when he had around $308 million in assets under management.

“At the time, I was encouraged by my wealthy clients who had made money in banking to have a plan B,” Gupta says. “My plan B was to go independent.”

In 2013, as the largest UBS affiliate in San Diego, managing around $540 million in client assets in almost 120 accounts, Gupta once more considered his options.

“In 2010, I started buying real estate. I thought it was a good idea because I was buying it substantially below cost. I was also interested in Dimensional Fund Advisors strategies, but I was blocked from making purchases on the UBS platform. I started to think more about how I could build responsible portfolios with the funds I had access to, but it was very difficult.”

As his frustration mounted, Gupta brought on Englewood, N.J.-based MarketCounsel to help guide the transition to independence. “I felt it was the right decision at the time,” he says.

Gupta was nervous about breaking away, unsure of how his clients would react.

“My biggest concern was going to be that I resign and nobody follows,” Gupta says. “That I put up my own office, my own location on a long-term lease, and no clients follow.”

One of the first clients he spoke with was Tony Robbins.

“I called him to explain what was happening; it was supposed to be a five-minute conversation,” Gupta says. “That conversation ended up lasting three and a half hours. He really wanted to understand as much about suitability and the fiduciary standard as possible and to be walked through the hidden fees. At the end, he not only stayed with me, he also asked me to be his primary advisor.”

In the end, all of his clients followed his breakaway, Gupta says.

“We were already managing $500 million,” Gupta says. “Our clients understood the fiduciary standard, we walked them through it, and they all consolidated their accounts and started to refer their family members.”

Even with the knowledge that his clients would follow, breaking away left Gupta with additional issues, like finding technological platforms to conduct the day-to-day business of a wealth management firm.

He eventually settled on the technology of Los Altos, Calif.-based Jemstep, which melded portfolio and relationship management systems, allowing advisors paperless, automated customer account transfers and self-service processes. “What surprised me was that my technology platform improved across the board from CRM to analytics to portfolio management,” Gupta says.

Finding the right custodian was also extremely important. Gupta initially used Schwab Advisor Services and Fidelity International Wealth Services as custodians, but has since added Pershing Advisor Solutions and TD Ameritrade Institutional.

“When clients hear those names, they immediately know that their assets are very safely invested,” Gupta says.

As an independent, Gupta has continued his commitment to the fiduciary standard, creating Portfolio Checkup, a web tool that allows investors to evaluate their portfolios and determine the cost of owning their investments.

“This was really inspired by Tony,” Gupta says. “I started thinking beyond myself. Tony made me realize that I had the opportunity to go beyond my high-net-worth clients and help others realize what their investments are costing them. Our technology goes in and scans your asset allocation and analyzes all the internal fees. It won’t tell you the commissions, but it will give you the cost of owning the individual investments, and the analysis is shocking to a lot of people.”

Portfolio Checkup was developed as a partnership between Gupta’s Stronghold Financial and Jemstep. The tool charges no fees to investors and has diagnosed almost $6 billion in assets to date.

While the original plan was to use Portfolio Checkup to refer interested investors into a low-cost, low-fee robo-advisor, the plan expanded to connect clients with RIAs nationally. Gupta vetted then partnered with a handful of leading national, independent firms which are recommended by Portfolio Checkup as fee-only alternatives to users paying high brokerage fees. This network has 75 offices around the country and collectively manages more than $45 billion in assets.

“We put together a client bill of rights to talk about maximum fees and to make sure firms guaranteed the fiduciary standard,” Gupta says. “They can go through the process. They may not be right for us or might prefer a more local advisor, so users can identify the right fit and transfer their accounts to that firm if they choose.”

Firms that receive assets through referrals from Portfolio Checkup pay 25 percent of their advisory fees to Stronghold annually.

“It’s a fully disclosed and transparent 25 percent of the advising fee,” Gupta says. “That allows us to continue to maintain this seven-figure website.”

But Gupta maintains that the website is a tool to spread awareness of the fiduciary standard and to educate clients from brokerage firms.

Now Gupta is setting the stage for his firm’s continued growth.

“We’re going to open an office in New York before the end of the year,” he says. “Our clients are spread out across the country, so we want to make sure we’re able to grow to serve them. I don’t know if we’ll double our assets again in less than two years, but I see us continuing to grow slowly and intelligently.”