The WealthStack Podcast

Technology in wealth management isn’t just changing, it’s colliding with reality. Advisors are expected to deliver deeply personalized experiences, operate at consumer-grade speed and navigate increasing complexity, all on top of legacy systems never designed for this moment. As AI accelerates what’s possible, the real challenge isn’t adopting new tools, it’s rethinking how technology supports the advisor experience from the ground up.

In this episode of The WealthStack Podcast, host Shannon Rosic sits down with Vestmark CTO Freedom Dumlao to go behind the curtain of modern wealthtech and unpack why advisor experience, data integration and agentic AI are now the real battlegrounds for scaling RIAs. 

Key takeaways:

Why consumer software experiences are redefining advisor expectations at work

How integration challenges quietly drain time and limit true personalization

Why agentic AI is the real leap forward

Why the advisor’s moat is validation, not information

How compliance doesn’t kill innovation, it sharpens it

Resources:

Listen to WealthStack on Wealth Management

Subscribe and listen to WealthStack on Apple Podcasts

Subscribe and listen to WealthStack on Spotify

Connect with Shannon Rosic:

Shannon Rosic

WealthStack website

Wealth Management

Connect with Freedom Dumlao:

LinkedIn: Freedom Dumlao

LinkedIn: Vestmark

Website: Vestmark

About Our Guest:

Freedom Dumlao is the Chief Technology Officer at Vestmark, where he leads the firm’s technology strategy with a focus on resilience, scalability, and building long-term client confidence. He brings a disciplined, hands-on approach shaped by senior leadership roles at Amazon, Zipcar, Flexcar, Wayfair, and Drift, including his work on the Alexa machine learning and AI platform. A strong advocate for open-source communities, Freedom also serves as a board member and treasurer of Ruby Central. Outside of work, he enjoys woodworking, cooking, and spending time with his two daughters building robots and experimenting with electronics.

“Personalization” has become one of the most overused words in wealth management and one of the hardest promises to actually deliver. Clients want portfolios that reflect their goals, values, tax realities, and life events. Firms want scale, efficiency, and fewer operational landmines. Too often, those two goals collide.

In this episode of The WealthStack Podcast, host Shannon Rosic sits down with Joshua Allen, CEO of TCP Asset Management, to unpack what real portfolio personalization looks like inside a fast-growing RIA and why most firms underestimate the operational cost of getting it wrong. Josh shares how TCP moved beyond model-only workflows, where automation actually helps (and where it doesn’t), and why saying no to most technology is critical to scaling personalization without creating an ops headache.

Key takeaways:

How hiring a director of advisory services strengthened tech integration

Why deeper use of existing tech beats adding more tools to the stack

How personalized portfolios are driving referrals across generations

Why most “personalized portfolios” still feel identical to clients

What’s real vs hype when it comes to AI in portfolio management

Resources:

Listen to WealthStack on Wealth Management

Subscribe and listen to WealthStack on Apple Podcasts

Subscribe and listen to WealthStack on Spotify

Connect with Shannon Rosic:

Shannon Rosic

WealthStack website

Wealth Management

Connect with Joshua Allen:

LinkedIn: TCP Asset Management

Website: TCP Asset Management

About Our Guest:

As a founding Partner and  Chief Executive Officer of TCP Asset Management, Josh Allen is charged with leading a team of wealth advisors in practice management, business development, and innovative planning solutions. These solutions have provided our clients with the resources and flexibility needed to deliver a personalized financial planning experience that is fluid and dynamic. Josh and his team have developed and refined a process that is comprehensive in nature and ties together: investment management, risk management, retirement income planning, estate planning, business and family legacy planning, and philanthropy. This exclusive process allows them to put together all the pieces of the financial puzzle for their clients as their lives unfold and be engaged when their needs evolve.

Josh received a Bachelor of Science degree from The Ohio State University in Family Resource Management. He also received a certificate in Financial Planning from Boston University. Upon completion of the education, examination and experience requirements, Josh obtained the Certified Financial Planner, CRPC® and CRPS® designations. His securities licenses include the series 7,9,10 and 66 and State of Ohio insurance license.

Josh is married to Branda, who is also one of his business partners. They together have three children, two dogs and two cats. As a family they love the outdoors, whether it is on the beach or in the mountains, they are always up for an adventure.

As advisors race to deliver “personalized” portfolios at scale, a hard reality is setting in: most personalization is still just a model tweak with a nicer label. Meanwhile, clients want more hands-on service, more transparency and more customization, while firms are trying to grow without hiring an army of operations and investment staff. The result is a widening gap between what clients expect and what legacy portfolio tools can realistically deliver. The firms that win won’t be the ones stacking more complexity. They’ll be the ones using automation to deliver truly bespoke outcomes, with clearer decisioning, tighter risk controls and better records behind every trade.

In this episode of The WealthStack Podcast, host Shannon Rosic sits down with Wes Caywood, head of distribution at Pave Finance, to unpack what “real personalization” actually means in 2026, why portfolio complexity rarely translates into client-perceived value and how automation can make portfolio management more defensible, not less. 

Key takeaways:

How to modernize portfolio management with “blowing up” your existing workflows

Where AI actually fits in portfolio management

Where the personalization gap shows up most clearly (and why it becomes an ops and time problem fast)

What automation should capture for compliance, auditability, and transparency 

The biggest mistake firms make when evaluating portfolio tech

Resources:

Listen to WealthStack on Wealth Management

Subscribe and listen to WealthStack on Apple Podcasts

Subscribe and listen to WealthStack on Spotify

Connect with Shannon Rosic:

Shannon Rosic

WealthStack website

Wealth Management

Connect with Wes Caywood:

LinkedIn: Wes Caywood

LinkedIn: Pave Finance

Website: Pave Finance

About Our Guest:

Wes Caywood is the Head of Distribution at Pave Finance, where he works closely with advisors and firms to modernize portfolio management through thoughtful use of technology and automation. With more than 20 years in financial services, Wes brings deep experience working with sophisticated clients, family offices, and advisory teams. A U.S. Naval Academy graduate and former Navy officer, he is driven by a service-oriented mindset and a focus on helping advisors deliver personalized, well-prepared client experiences at scale.

As artificial intelligence-powered tools flood the market and marketing becomes faster, cheaper and easier to automate, advisors are discovering an uncomfortable truth: more tech doesn’t automatically create more trust. In an industry that’s louder and more crowded than ever, growth is no longer a tactics problem; it’s an attention, resonance and differentiation problem. The firms that win will be the ones that understand how technology amplifies identity, not replaces it, and how behavioral finance and neuroscience shape decisions long before a prospect ever takes a meeting.

In this episode of The WealthStack Podcast, Shannon Rosic sits down with Dr. Joshua Wilson, founder of NeuBeFi, to explore where tech, behavioral finance, and human psychology actually intersect, and why most advisors are focusing on the wrong side of the decision-making process.

Key takeaways:

Why most firms have a marketability problem, not a marketing problem 

How technology amplifies identity rather than creating differentiation

What “signal discovery” means and how it turns sameness into differentiation

Why growth fails when treated as a checklist instead of a diagnosis

How clarity and cognitive relief drive trust in money decisions

Resources:

Listen to WealthStack on Wealth Management

Subscribe and listen to WealthStack on Apple Podcasts

Subscribe and listen to WealthStack on Spotify

Connect with Shannon Rosic:

Shannon Rosic

WealthStack website

Wealth Management

Connect with Dr. Joshua Wilson:

LinkedIn: Dr. Joshua Wilson

LinkedIn: NeuBeFi

Website: NeuBeFi

About Our Guest:

Dr. Joshua Wilson is the pioneer behind Neuro-Behavioral Finance—a transformative approach that fuses behavioral finance, neuroscience, narrative strategy, and decision science to help advisors and FinTechs become the only option their ideal clients feel drawn to.

Before becoming a sought-after strategist to RIAs and FinTechs, Joshua spent nearly two decades inside the arena where he achieved significant success. Joshua has personally closed hundreds of millions in AUM both virtually and in person.

During his time with TD Ameritrade, he was a highly decorated advisor, National Coach of the Year, led the national sales training program, and traveled the country representing the firm.

After transitioning to the independent RIA world, he built and grew his advisory practice from $0 AUM and no base salary. After selling his book, he led another RIA from turnaround to rapid expansion to acquisition as CEO. In addition to guiding wealth advisors and FinTechs, his expertise has been sought by $20+ billion asset managers, platforms backed by Y Combinator, marketing agencies, and venture capital firms.

His programs have reshaped firms that later appeared in Forbes, Financial Times Top 300 RIAs, the RIA Database’s Top 100 Emerging Wealth Managers, and more. Individually, Joshua has been named to multiple Forbes lists honoring America’s top financial advisors and recognized multiple times as a 5 Star Wealth Manager.

For three years running, the WealthStack season has officially started the same way: with an unfiltered wealthtech outlook conversation between Shannon Rosic and Davis Janowski, senior technology editor and research analyst at Wealth Management. If 2025 was the year firms finally started using AI, 2026 is shaping up to be the year we find out whether all that tech actually pays the rent.

In this annual tech vibe check, Shannon and Davis dig into how AI notetakers quietly reshaped advisor workflows, why agentic AI and “AI operating systems” are the next wave, and what this all means for junior talent, firm structure and the future “Chief AI Officer.”

They also explore whether Franken-stacks are really dying, how niche platforms and new lead-gen tools are redefining value, and why cybersecurity and deepfakes may be the biggest underpriced risks on every CTO’s roadmap. 

Key takeaways:

What under-the-radar innovations to watch in the 2026

How data fragmentation limits real AI adoption despite rising tech budgets

What agent-based platforms signal about the future of advisor software

Why critical thinking remains more valuable than pure AI skills

How cybersecurity risks are growing faster than regulatory responses

Resources:

Listen to WealthStack on Wealth Management

Subscribe and listen to WealthStack on Apple Podcasts

Subscribe and listen to WealthStack on Spotify

Connect with Shannon Rosic:

Shannon Rosic

WealthStack website

Wealth Management

Connect with Davis Janowski:

LinkedIn: Davis Janowski

Instagram: @DavisJanowski

About Our Guest:

Davis Janowski is a New York-based technology journalist whose work spans consumer, business and the FinTech sectors.

Prior to his six years with WM, Janowski worked for Forrester Research as an analyst covering Digital Wealth Management. In edition, he has worked for two FinTech startups, Wealthfront and New York-based FeeX, Inc. (now Pontera). His work covering the advisor tech space began in 2007 when he joined InvestmentNews as the advisor industry’s first dedicated technology reporter. His start in tech journalism began as an editor with PC Magazine in 1999 where he later served as an analyst and reviewer.

His work has appeared in The New York Times, Wealth Management, Financial Planning, RIABiz, InvestmentNews, PC Magazine, numerous blogs and several books, including Technology Tools for Today’s High Margin Practice. He has also been a speaker and moderator at numerous industry conferences.

Outside his day-to-day he is a senior guide for Manhattan Kayak Company in New York City.