WealthTech on Deck

In this episode, Jack talks with Keith Gregg, Founder, and CEO of Chalice Network, a fintech company based in San Diego.

Keith has more than three decades of experience in financial services and executive leadership. During the first part of his career, he served as a financial advisor and created his first independent business focused on planned giving. Keith also served in the US Marine Corps and was the recipient of the Presidential Service Award from President Ronald Reagan. 

Keith and Jack discuss the benefits of creating digital marketplace e-commerce platforms, helping small businesses, and embracing tech advancement in the industry.

“There's no turning back--that genie is out of the bottle. They're not going to put it back in, so you better become incredibly perfect with being able to digitally communicate and coordinate and deliver to your customers via a digital platform.” ~ Keith Gregg

In this episode, Jack talks with Lee Chertavian, Operating Partner at Long Ridge Equity Partners.

Lee is one of the pioneers in the advisory space. He was the CEO of Placemark, a sophisticated asset management company, which was purchased by Envestnet seven years ago. Lee led its growth to nearly $16 billion in assets under management with more than 45,000 clients. Furthermore, Lee finished his MBA with distinction at Harvard Business School.

Lee and Jack discuss the improved tax management in UMAs, six key trends in fintech, and the role of tech in enabling advisors to make better decisions.

“Consider a client's entire lifestream. We need to figure out planning. We need to integrate with tax, not just the tax on the portfolio, but their whole tax situation. And fortunately, so much data is becoming more digitized that we have the ability to bring that in—to help the advisor make those better decisions for clients.” ~ Lee Chertavian

In this episode, Jack talks with Jeff Quigley, Vice President of Enterprise Relationships at LifeYield about navigating the world of social security. They’re also joined by Alyson Dorosky, Marketing and Social Security Specialist at LifeYield.

Jeff helps thousands of advisors understand and implement LifeYields’ Social Security+ solution through group training and seminars. Alyson is a technical lead at LifeYield and covers the gamut of client services, including helping advisors keep track of the myriad rules around social security. 

Jeff and Alyson talk with Jack about maximizing retirement income outcomes by leveraging social security tools, and the concept of delayed filing credits (for the client and the surviving spouse), and layers of income.

"If you don't have these tools, it is difficult to make good informed decisions that you can benefit from. Firms that are adopting these kinds of technology and tools, for instance, when the pandemic hit, their usage went through the roof. They were ready in a digital world right there.” ~ Jeff Quigley

In this episode, Jack talks with Scott Holsopple, Chief Growth Officer at Hightower Advisors.

Scott has 20 years of experience in investment banking, private equity, and wealth management. Scott and his team at Hightower work with firms to help them stand out and achieve the vision for the next chapter of their business.

Scott and Jack discuss what goes into a thoughtful client experience and how adding value and scale helps achieve organic business growth.

"We’re in an ever more competitive industry. Technology is enabling us to do more things. Firms with scale are really deploying assets and specialties and expertise in a way that's never been done before in this industry. And I think it's going to require us to be more thoughtful.” ~ Scott Holsopple

In this episode, Jack talks with Paul Deer, Vice President of Advisory Service at Personal Capital.

Paul oversees a team of more than 60 financial advisors and their clients at Personal Capital, the first advisory firm of any scale to conduct their business online. In addition, Paul is passionate about hybridizing wealth technology with human interaction so you can provide holistic and personalized advice at the same time.

Paul and Jack discuss the reinvention of retirement planning, the importance of advisor specialization, and the confluence of human and digital advice.

“We have found that you can't just do it with tech. You need to have humans to have a real conversation with where you can perceive emotions and kind of dig deeper than just the surface of what someone's telling you. So that combination is what's going to help people make the best possible financial decisions over and over again, throughout their lifetime. Which is going to help them with the best possible outcome.” ~ Paul Deer

In this episode, Jack talks with Daniel Crosby, Chief Behavioral Officer at Orion Advisor Solutions.

Daniel is a psychologist and a behavioral finance expert who helps advisors and investors understand the psychology of financial markets. He believes that through tools, such as the Irrationality Index and the new 3D Risk Profile from Orion, we'll be able to assess emotional reactions to volatility.

Daniel and Jack discuss the benefits of risk management tools, the role of human behavior and psychology in investing, and the future of behavioral finance.

"We need to educate clients and advisors about the realities of behavioral finance. We need the right environment, the right portfolio mix for them, but we also need that encouragement that's happening just in time to educate people when they're on the precipice of making a decision.” ~ Daniel Crosby

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In this episode, Jack talks with Jud and Kim Mackrill, Co-Founders and CMOs at Milemarker, Inc.

Kim and Jud Mackrill are partners in life and in business. Together, they have built careers on providing solutions in tech integration for the finance world. Before Milemarker, they helped advisors innovate through their marketing company, Mineral Interactive. After Mineral’s acquisition, Kim and Jud led the rebranding of Carson Group.

Kim, Jud, and Jack discuss harnessing the power of data, modernizing your firm’s tech stack, and the importance of client behavioral psychology in tech implementation.

“This is the path. You have to really start with empathy designed for the user, build the data model, and then deliver it because the future is far more complex.” ~ Jud Mackrill

In this episode, Jack Sharry talks with John Connors, the Founder and CEO of Boathouse Inc.

Before building his firm in 2001, John worked for corporations such as Hill Holiday and McCann Worldgroup. John’s vision of success and high performance as a marketer was greatly influenced by these industry pioneers and set him on the path to building his own firm.

John talks about why maintaining clients over the long-term is essential to success. High client retention is a matter of having a connection strategy, leveraging data, and building a narrative around the business.

John and Jack discuss the concept of narrative economics, the importance of storytelling, and the use of data sets to drive brand strategies.

“Narrative drives economic impact. Most CEOs and CFOs know that. They have economic data (GDP, employment, housing, etc.) but never narrative data to look at causality, correlation related to the economic data.” ~ John Connors

In this episode, Jack Sharry talks with Heather Kelly, the Senior Vice President of Advisory and Strategic Accounts at Allianz Life Insurance Company of North America.

Heather has been in the industry for over 25 years. However, if she was asked at the beginning of her career what wealth tech means, and what it would mean after decades, she would brush it off and continue doing what the mentors before her told her to do.

Heather has been in different roles in different big insurance companies, including United Capital and Allianz. Throughout those years, she offered her expertise and led the conversations about risk management, insurance, retirement planning, and now, fintech innovation and integration. Heather was also the first recipient of The Young Professional Honor for her advocacy in helping women excel in their profession.

Heather and Jack discuss the future of distribution, continuous innovation in the industry, and advocating for increased knowledge of technology.

“Continuing to innovate, continuing to think what the next iteration is going to be, what’s going to make the client experience and the advisor experience even better—that’s something we should talk about in the industry often.” ~ Heather Kelly 

In this episode, Jack Sharry talks with Len Reinhart, a pioneer in the UMH industry and founder of several successful advisory firms. Len began discussing the subject of separately managed accounts, managed money, an advisory approach, and, of course, UMH, nearly 20 years ago. 

As a baby boomer himself, Len witnessed firsthand the diminishing benefits for boomers as retirement suddenly became their primary responsibility. Simultaneously, he began his career working with managed money where the goal was listening to clients first, unlike the aggressively cold-calling brokers he sat beside. He listened to clients’ goals, their risk requirements, and built strategies to meet those individual needs. 

Focusing on retirement and listening to clients’ end goals, both financial and personal, became the basis of his approach to advising. As he built firms with a client-first approach in mind, his success caught the attention of competitors and the industry. 

Len and Jack discuss the transition from winning the financial rat race to simply funding future liabilities. They also discuss why UMH is such a powerful tool for accomplishing lifelong goals and how the role of advisors has shifted to help clients reach those goals. 

“The end goal of the unified managed household is to take all the clients’ assets, their goals, and aspirations – meaning what are they trying to accomplish with their life – and put them together. And I think the further you take this, the better.” ~ Len Reinhart