This week, Jack Sharry talks with Parker Ence, CEO & Co-founder of Jump Advisor AI, a fast-growing startup that brings an AI-enhanced client meeting cycle to financial advisors. Parker is an entrepreneur and operator with 12 years of CEO/Co-founder experience across advisortech, data/DaaS, AI, SaaS, and insurtech. 

Jack and Parker discuss how Jump helps RIAs and broker-dealers slash client meeting admin time by up to 90%. From real-time meeting prep and automated CRM updates to actionable insights and compliance-ready workflows, Parker shares how Jump revolutionizes the client meeting cycle for financial advisors. He also explores the company's rapid growth, significant enterprise partnerships, and his vision for the future of AI in financial services.

In this episode:

(00:00) - Intro

(01:39) - The origin of Jump Advisor AI

(03:30) - Jump's most popular product and what it does

(05:01) - Jump's enterprise-level partnerships

(06:18) - Parker's startup journey

(11:29) - Jump's three core products

(13:35) - Parker's outlook on AI in financial services

(15:29) - Parker's key takeaways

(17:34) - Parker's interests outside of work

Quotes

"What we're best known for is our AI meeting assistant that's made for advisors. And whatever the compliance team has approved, that's the most popular." ~ Parker Ence

"Don't worry so much about getting replaced by AI. Worry about getting outcompeted by other advisors who are adopting AI faster." ~ Parker Ence

"Everything that is inside the Jump product is there because an advisor requested it. So, we love partnering with RIAs, broker-dealers, solo advisors, and any of our customers to co-create the future." ~ Parker Ence

Links 

Parker Ence on LinkedIn

Jump AI

Cetera

Osaic

LPL Financial

Tim Chaves

Stanford Graduate School of Business

Google Cloud

Salesforce

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This week, Jack Sharry talks with Pete Hess, President of PureFacts. Before joining PureFacts, Pete served as Chief Revenue Officer for Americas at InvestCloud, and earlier in his career, he was CEO of Advent Software. At PureFacts, Pete leverages the firm's revenue management solution for global wealth and asset management firms, helping clients unlock new revenue streams and uncover new avenues for growth.

Jack and Pete discuss revenue management, the limitations of spreadsheets, and the importance of back-office software in the wealth and asset management space. Pete shares how firms can stop revenue leakage, optimize compensation, and leverage data to make smarter business decisions, moving beyond outdated spreadsheets and into the future of automated, insightful financial operations.

In this episode:

(00:00) - Intro

(01:45) - Pete's career journey

(08:56) - How PureFacts helps firms

(12:06) - Harvesting data for business insights and anomaly reporting

(17:02) - How PureFacts uses AI in its products and services

(20:37) - Solving regulatory issues

(21:50) - Pete's key takeaways

(23:32) - Pete's interests outside of work

Quotes

"Anytime you find spreadsheets, you've got an opportunity to sell software." ~ Pete Hess

"Revenue management is often taken for granted. People are using spreadsheets and fingers to do it, which is not what you should be doing in a space that can be programmatically automated." ~ Pete Hess

"Don't take for granted all your back-office processes. When you see spreadsheets, there are probably errors being made, and time-to-money is being delayed." ~ Pete Hess

Links 

Pete Hess on LinkedIn

PureFacts

SS&C Advent

InvestCloud

John Wise

Stephanie DiMarco

Khoros

Vista Equity Partners

WCAS

GrowthCurve Capital

PureRewards | PureFacts

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This week, Jack Sharry talks with Stephen Chen, Founder & CEO of Boldin. Stephen is a classic entrepreneur who takes pride in creating innovative ways to help anyone achieve financial independence. He built the "TurboTax" for financial planning and has been creating platforms for SAAS, classes, coaching, and CFPs for consumers, advisors, and companies.

Stephen talks with Jack about how he makes retirement planning more accessible, collaborative, and user-friendly. He shares how he built a "TurboTax" for financial planning that resonates with DIY planners and high-net-worth individuals and how Boldin has evolved from a direct-to-consumer offering to a robust platform serving consumers, advisors, and large enterprises.

In this episode:

(00:00) - Intro

(01:39) - What Bolden does and why it matters

(03:12) - The growth in user adoption for financial planning

(06:23) - Stephen's career journey

(10:09) - Boldin's organic growth strategy

(13:14) - Stephen's plans and investment strategies

 (15:54) - Creating a collaborative platform for advisors

(18:10) - The role of AI in Boldin's operations

(20:51) - Using simulations to optimize financial actions

(23:13) - Steve's key takeaways

(24:050 - Steve's interests outside of work

Quotes

"We want anyone to be able to build their own financial plan and, through planning, get literate, make good decisions, hopefully take action, and achieve better outcomes in their life." ~ Stephen Chen

"If financial advisors are aging out, how do we bridge that gap? I think it's going to be technology enabling advisors to serve more people." ~ Stephen Chen

"AI is real, and it's amazing how fast it's changing and what's possible. It's shocking, and it's a little scary." ~ Stephen Chen

Links 

Stephen Chen on LinkedIn

Boldin

Charles Schwab

Wells Fargo

Salesforce

RTX

McKinsey

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This week, Jack Sharry talks with Rob Pettman, President of TIFIN. Rob brings more than 20 years of leadership experience across wealth management, investment platforms, and financial technology.  Before joining TIFIN, Rob served as Executive Vice President of Wealth Management Solutions at LPL Financial, where he oversaw the firm's investment product distribution, retirement business, advisory platforms, and research organization, managing over $70B in AUM. During his 19-year tenure, he helped lead LPL through its rapid growth to $1.4T in assets and more than 22,000 advisors.

Jack and Rob talk about how AI is changing the way wealth and asset management firms grow and operate. Rob also shares how TIFIN uses AI to improve the overall growth of these businesses and how those who embrace AI as a growth engine are reaping the benefits through organic client growth, advisor enablement, and enhanced decision-making.

In this episode:

(00:00) - Intro

(01:49) - How advisory firms can use AI to their advantage

(04:22) - Strategic use cases for AI

(06:03) - The evolving results of AI implementation

(08:37) - How TIFIN uses AI for wealth and asset managers

(14:47) - The process of refining AI capabilities

(16:47) - The current state and future outlook for AI adoption

(20:12) - The characteristics of firms leading in AI adoption

(22:17) - Rob's key takeaways

(24:23) - Rob's interests outside of work

Quotes

"Just doing AI for better experiences doesn't create commercial value. And so actually having these specific problems to solve with the intended outcome in mind is really where it's at." - Rob Pettman

"Traversing multiple systems in financial services or wealth management is still a problem. There are solutions for this now where AI can actually straddle all of these disparate systems and put together a holistic view of the client relationship, the portfolio, and how they are doing relative to the plan." ~ Rob Pettman

"Some of the firms that are furthest ahead have the ability to operate with speed. They try to minimize distributed decision-making and have an accountability mindset that enables decisions to actually occur faster." ~ Rob Pettman

Links 

Rob Pettman on LinkedIn

TIFIN

LPL Financial

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In 2024, SEI made a strategic investment in TIFIN.

This week, Jack Sharry talks with J. Womack, Head of Asset & Income Optimization at SEI. In his role, J. drives revenue growth by helping investors keep more of what they earn by optimizing their household assets for tax and retirement income. He focuses on expanding SEI's ability to deliver differentiated, client-centric wealth solutions that improve financial outcomes at both the household and enterprise level.

Jack and J. explore the growing importance of tax management in wealth creation and how the industry is moving toward the UMH. J. also discusses the distinction between a multi-account UMA  and a multi-account UMH, how the convergence of technology, operations, and products is setting a new standard for value delivery in the industry, and why tax optimization has become one of the most powerful differentiators in wealth management today.

In this episode:

(00:00) - Intro

(02:03) - J.'s background and career history

(08:09) - J.'s transition into fintech and his early days at SEI

(09:48) - From technology expert to investment strategist

(12:37) - The role of tax management in advisor value

(16:34) - The road to the unified managed household

(21:37) - Unlocking the value of tax through tech, product, and service delivery

(26:01) - Why tax smart strategies drive organic growth

(28:36) - Workplace insurance and annuities

(32:01) - J.'s key takeaways

(34:23) - J.’s interests outside work

Quotes

"UMH has the potential to play an integral role in the workplace as providers are looking at ways to deliver more value to plan sponsors and solve real problems for investors." ~ J. Womack

"Taxes are where all the action is. It's where the biggest misalignment between client expectations and advisor behavior is. If you solve that, you create a really compelling value proposition that will be attractive to people and create stickier relationships." ~ J. Womack

"Multi-account UMA is the foundation of getting to UMH. Closing that gap from a tax perspective, that's where you have the ability to actually deliver comprehensive tax management." ~ J. Womack

Links 

J. Womack on LinkedIn

SEI

The Wharton School

Jeff Benfield

Scott Smith

Cerulli Associates

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Scott Smith is the Senior Director of Advice Relationships at Cerulli Associates, where he leverages deep research and analysis to define challenges and deliver solutions across the wealth management landscape. Known for his clear-eyed insights, Scott studies market trends, advisor behavior, and platform innovation to help firms navigate an increasingly complex industry.

This week, Jack talks with Scott about his latest research on U.S. managed accounts and why tax optimization has emerged as the top priority for firms, surpassing even portfolio construction. They dive into strategies like tax-loss harvesting, asset location, and tax-smart withdrawals, exploring both the progress being made and the challenges that remain. From compliance and legacy systems to advisor adoption and third-party solutions, Scott highlights what firms must do to make tax-smart investing accessible, effective, and essential for client success.

In this episode:

(00:00) - Intro

(01:56) - Cerulli’s latest research on managed accounts 

(04:29) - Surprising findings from the study

(05:46) – Why asset location has seen little progress

(06:45) – The reasons asset location remains underused

(09:18) – Walking the fine line between tax planning and tax advice

(11:18) – Making tax optimization simple and straightforward

(12:38) – Tax-loss harvesting and transition management

(14:14) – Coordinating multi-account households for tax efficiency

(19:31) – The complexities of managing dynamic households

(21:14) – Scott’s recommendations for better tax planning

(24:42) - Scott's key takeaways for firms and advisors

(26:00) - Scott's interests outside of work

Quotes

"Our goal isn't to educate advisors on every line of the tax code. But letting them know what the fundamentals are, what each of these steps is doing, and then giving them the tool to do it is the most important part." ~ Scott Smith

"A lot of the advances in this industry are limited by advisor adoption. So it's most important to create this path of least resistance to tax optimization." ~ Scott Smith

"Trying to steer a legacy portfolio accounting or advisor workstation into a better place and redoing the whole thing on the way while still trying to do business is not easy for anyone. So the firm setting up systems to take care of this and making it as easy as possible for advisors to do that is the only way to compete long term." ~ Scott Smith

Links 

Scott Smith on LinkedIn

Cerulli Associates

Vanguard

Morningstar

EY

55ip

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This week, Jack Sharry talks with Ken Dychtwald and Ken Cella. Ken Dychtwald is the Founder & CEO of Age Wave. He is a psychologist, gerontologist, and author of 19 books. For decades, Ken has been regarded as the nation's foremost thought leader on population aging and its profound business, social, financial, and cultural implications for the healthcare workforce. 

Ken Cella is the Head of External Affairs at Edward Jones, where he is responsible for fostering strategic partnerships and expanding relations with policymakers, industry leaders, and other influencers to make a greater impact on society. He is also a member of the Edward Jones Enterprise Leadership Team, which guides the firm's strategy to grow its impact and create value for clients, colleagues, and communities today and into the future. 

Together, they unpack one of the most overlooked and under-discussed financial issues in American households: caregiving. Drawing on insights from research commissioned by Edward Jones in partnership with Morning Consult and Age Wave, Ken Cella and Ken Dychtwald share the emotional, financial, and societal costs of caregiving. With nearly half of all Americans either serving as or expecting to become caregivers, this conversation sheds light on what it truly means to care for a loved one and what financial advisors can do to better support clients in navigating these challenges.

In this episode:

(00:00) - Intro

(02:29) - Edward Jones’ groundbreaking study on caregiving 

(04:25) - The wide-ranging impact of caregiving on families and society

(06:57) - Why Edward Jones is investing in caregiving research

(11:06) - Caregiving’s reach: a reality for nearly everyone 

(13:47) - Edward Jones’ transformation toward holistic financial wellness

(18:29) - Culture, community, and client well-being at the center

(21:18) - Balancing technology with timeless values

(23:59) - Building trust in the advisor–client relationship

(27:45) - Ken Cella on the emotional toll—and fulfillment—of caregiving

(30:05) - Ken Dychtwald’s key insights and takeaways

(32:30) - Ken Cella's interests outside of work

(33:25) - Ken Dychtwald's interests outside of work

Quotes

"Caregiving takes a toll beneath the surface, and a lot of times, people don't talk about it." ~ Ken Cella

"We're in the business of helping people feel competent and secure in their financial future. So, we want to improve retirement security for families and caregivers." ~ Ken Cella

"Edward Jones is really serving the fabric of America in a way that's unique. We want to be part of a solution where business and society come together to create better outcomes for families through financial wellness." ~ Ken Cella

"It's not just the super-wealthy who need someone in their corner. It's everyday folks who need a guide, someone to direct them and help them." ~ Ken Dychtwald

"I have never encountered a firm that I thought cared more about both its work, the people who work there, the population it serves, and the community. So, I've grown a lot of respect and affection for the people of Edward Jones, and I feel proud to be affiliated with Edward Jones." ~ Ken Dychtwald

"There's a lot of strain, disruption, and unhappiness that can come with seeing somebody you love struggle. But there was also a sense of honor and a sense of doing something good for a loved one. The fact that Edward Jones is taking the lead in representing the purpose of caregiving, its high intention, and the quality of life that comes from it is to be applauded." ~ Ken Dychtwald

Links 

Ken Cella on LinkedIn

Ken Dychtwald on LinkedIn

Age Wave

Edward Jones

Morning Consult

Susan Collins

Mark Warner

Brittany Pettersen

Maria Elvira Salazar

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Teddy Gold is the co-founder of 3i Members, a private, invite-only network for family offices, exited entrepreneurs, and active fund managers. With a background in investment and a passion for building communities rooted in trust, Teddy helped launch 3i to solve the problem of random deal sourcing by leveraging curated peer collaboration. 

This week, Jack Sharry talks with Teddy about how 3i Members has grown into a thriving platform that facilitates smarter investing through crowdsourced expertise and strong relationships. They explore how the network vets opportunities, builds trust through shared values and non-solicitation, and helps members navigate everything from private deals to personal financial decisions. Teddy also shares why many successful investors are turning away from traditional wealth management models in favor of peer-driven, transparent support systems.

In this episode:

(00:00) - Intro

(01:58) – What is 3i Members?

(03:57) – Why investing benefits from qualified crowdsourcing

(05:30) – How the 3i crowdsourcing model actually works

(07:09) – The role of trust in successful peer investing

(08:50) – Community, credibility, and connection: the currencies of 3i

(14:03) – Core principles behind a trusted investment platform

(19:27) – The 3i business model: transparency over transaction fees

(21:16) – Teddy’s big takeaways on trust and network-driven decision-making

(24:13) - Teddy's interests outside of work

Quotes

"Deal sourcing is random, and we can make that process less random by creating a network of people we know and trust." ~ Teddy Gold

"There's no shortage of noise in the world, particularly around investments, and no shortage of new sources of information. What's hard is finding good, curated, quality voices." ~ Teddy Gold

"Investing is a good application of crowdsourcing as long as the crowd itself is qualified." ~ Teddy Gold

"The fundamental piece of building trust is giving in proportion to the amount you're taking in a relationship." ~ Teddy Gold

Links 

Teddy Gold on LinkedIn

3i Members

Mark Gerson

GLG

Billy Libby

Goldman Sachs 

Upper90

City Parks Foundation

Authentic and Ethical Persuasion

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John Sweeney is a seasoned financial services leader with a career spanning senior roles at Fidelity Investments to entrepreneurial ventures at the forefront of innovation. Over nearly two decades at Fidelity, he drove product and technology development across mutual funds, ETFs, managed accounts, and retirement solutions. After leaving Fidelity, he immersed himself in startups exploring blockchain, alternative investments, and AI. Today, as head of Praxis Solutions, he blends strategic insight with advanced technology execution, helping wealth and asset management firms harness AI and blockchain to improve efficiency, decision-making, and client outcomes.

This week, Jack talks with John about how Praxis Solutions uses AI and blockchain in concert to solve complex challenges in financial services. From dramatically reducing investment review times to enhancing compliance processes, John explains how his team builds custom, scalable tools that integrate into existing workflows. They explore blockchain as a “source of truth” and AI as a visible decision-making engine—technologies that together improve efficiency, reduce costs, and democratize access to institutional-grade advice while maintaining accuracy, transparency, and regulatory compliance.

In this episode:

(00:00) - Intro

(01:21) – John’s career journey: from Fidelity leadership to fintech innovation

(03:44) – Moving into the blockchain space and its early applications

(05:58) – Where smaller companies should begin their AI journey

(07:23) – How AI and blockchain work together

(09:18) – Inside Praxis Solutions: strategy, execution, and innovation

(12:07) – The types of clients Praxis serves best

(15:20) – AI as a powerful tool for building new solutions

(16:44) – Breaking down the Praxis business model

(18:34) – Front, middle, and back-office AI use cases in financial services

(21:41) – Streamlining compliance, policies, and procedures with AI

(24:15) – The future of AI in financial services

(26:19) – How AI is reshaping the cost of custom solutions

(28:02) – John’s top takeaways for financial leaders exploring AI

(29:41) - John's interests outside of work

Quotes

"AI, in general, is great at taking large, complex data sets that are today analyzed by expensive humans." ~ John Sweeney

"When we think about our aspirations as a firm and why we think AI is going to be a useful tool for financial advisors and their ecosystem that serves end investors, we think it democratizes a lot of access to institutional-grade theses." ~ John Sweeney

"The cost of custom software used to be very expensive, and AI development has changed that." ~ John Sweeney

Links 

John Sweeney on LinkedIn

Fidelity Investments

Praxis Solutions

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This week, Jack Sharry talks with Jamie Hopkins, Chief Wealth Officer at WSFS Bank and CEO of Bryn Mawr Capital Management. Before WSFS Bank, Jamie held various positions at Carson Group, including Managing Partner of Wealth Solutions, Managing Director of Carson Coaching, and Director of Retirement Research. Jamie is also the Founder of FinServ Foundation, a nonprofit dedicated to coaching and developing the next generation of financial professionals. 

Jamie shares his journey from personal tragedy to industry leadership, highlighting how his mother’s experience inspired a lifelong mission to expand access to financial guidance. They explore the convergence of wealth management models, the future of trust and estate services, and why firms must invest in people over products. Jamie also discusses his work with the FinServ Foundation, advocating for a more inclusive and sustainable financial industry.

In this episode:

(00:00) - Intro

(02:20) – Jamie’s personal “why” for joining the financial industry

(06:13) – A career built on passion, scale, and purpose

(09:05) – How firm types are converging in today’s landscape

(13:38) – The challenge of defining and delivering differentiated service

(17:33) – What’s next: Trusts, estate planning, and digital disruption

(19:44) – Why estate planning is the industry’s overdue frontier

(22:00) – Jamie’s mission to give back and shape the next generation

(25:18) – Three takeaways for the future of financial advice

(27:08) - Jamie's interests outside of work

Quotes

"Great companies come down to great people. Try to find great people to surround yourself with. You're only as good as they are." ~ Jamie Hopkins

"I see firms that want to be everything to everybody, and realistically, you usually cannot be that. That holds you back from some of the growth and scale that you might be looking for." ~ Jamie Hopkins

"Wealth management services look more similar everywhere. It's your people for the next decade that are going to distinguish you from anywhere else. So, invest in your people, take care of them, hire great people, find great people, and keep them." ~ Jamie Hopkins

Links 

Jamie Hopkins on LinkedIn

WSFS Bank

FinServ Foundation

The American College of Financial Services

Carson Group 

Omani Carson

SEI

iCapital

Trust & Will

Wealth.com

Wealth Management EDGE Conference

Financial Services Institute

Schwab Impact conference

McKinsey

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