Wealth Management
View MoreEpisode 074: In this “Best of 2024” episode of The Connected Advisor, Kyle Van Pelt brings together four leaders from four firms to discuss why firms should own their data and why data and technology are keys to success. Featuring Mike Prior, Brian Preston, Mark DeLotto, and Chrissy Lee.
In this episode:
(00:00) – Intro
(00:52) – Mike Prior on the importance of a modern approach to technology.
(04:37) – Brian Preston on how to build organic growth by being on the front edge of technology.
(07:00) – Mark DeLotto on the criticalness of data in all aspects of building a firm.
(12:00) – Chrissy Lee on how technology is the secret to exceptional operations.
Links
Mike Prior on LinkedIn
Priority Financial Group
Brian Preston on LinkedIn
Abound Wealth
Mark DeLotto on LinkedIn
Simon Quick Advisors
Chrissy Lee on LinkedIn
Merit Financial Advisors
Connect with our hosts
Milemarker.co
Kyle on LinkedIn
Jud on LinkedIn
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Episode 015: One of the biggest challenges in managing a wealth management firm is integrating various systems and platforms to create a seamless workflow. This challenge can often feel like trying to piece together a complex puzzle where every component must fit perfectly to maintain a technological edge in the industry. In such a rapidly evolving field, providing a comprehensive infrastructure for advisors is essential, as it allows them to concentrate their efforts on what truly matters: exceptional client service and sustainable growth.
In this episode of Connected, Kyle talks with Kyle Wesley, Chief Digital Officer at Bleakley Financial Group. They discuss the challenges of managing a firm, the importance of integration in the technology stack, and the future of the industry. Kyle also shares insights on how Bleakley supports its advisors and leverages technology to provide a seamless experience. He highlights the role of technology and artificial intelligence in driving growth and efficiency.
Join us as we discuss:
[02:10] – Being a Penn State Nittany Lion fan.
[03:38] – The role of a chief digital officer in an RIA.
[05:49] – How to stay on top of technology changes in the industry.
[07:03] – Bleakley’s predefined technology stack.
[08:30] – Bleakley’s criteria for integrating its core systems.
[10:23] – Advisors’ support system at Bleakley.
[14:46] – The challenges of managing a platform.
[17:38] – What it takes to implement technology in a platform.
[21:58] – The challenge of integrating multiple platforms.
[26:09] – The use of Power BI for data analysis.
[30:11] – Kyle’s thoughts on the future of the financial advisory industry.
[35:23] – Kyle’s favorite thing to do outside of work.
Key Takeaways
Providing a comprehensive infrastructure for advisors allows them to focus on client service and growth.
Integration is a key challenge in managing a technology stack, and Bleakley prioritizes seamless integration between platforms.
The future of the industry lies in a centralized data warehouse and a user interface that brings together all the necessary tools and information.
AI has the potential to revolutionize the industry by automating processes and providing personalized insights for advisors.
Quotes
“In everything we do, we pilot with a small user group. We get more feedback before we roll it out slowly to a broader group until it is fully rolled out to all advisors and staff.” ~ Kyle Wesley
“The challenging part of any integration is if you have different platforms, it’s never going to be completely seamless. So that’s definitely the challenge because you have to teach everyone where you need to go for which thing, and it’s not going to be one spot.” ~ Kyle Wesley
“Cybersecurity, in general, is probably the biggest threat to our business. But if you’re able to normalize the data because you have it from so many sources, that’s where AI becomes more meaningful.” ~ Kyle Wesley
Links
Kyle Wesley on LinkedIn
Bleakley Financial Group
Michael Kitces
Orion Advisor Solutions
Salesforce
Practifi
Ignite CRM Solutions
eMoney Advisor
LPL Financial
Pontera
DocuSign
Power BI
Connect with our hosts
Milemarker.co
Kyle on LinkedIn
Jud on LinkedIn
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Google Podcasts
Produce game-changing content with Turncast
Turncast helps your company grow by producing top-quality content and fostering transformative conversations. We specialize in content generation, podcasting, digital strategy, and audience growth for fintech and financial services companies. Learn more at Turncast.com.
In this episode of Connected, we talk with Rich Walker, Founder and CEO of Quik!. Rich shares his inspiring career journey and the ups and downs that eventually led him to build Quik!. He talks about what real connection with clients is all about, and his mission to motivate and empower people to be the best versions of themselves.
We also dive into technology, the challenges of standardized data collection, and the importance of automation for financial advisors. In a fragmented industry where a mere 20% of transactions are automated, Rich provides a fresh perspective on how automation can help advisors focus on what is most important.
As a student of communication, Rich also provides insight into the key elements of great connections and how intentional practice can help advisors become better listeners, leading to better outcomes.
Join us as we discuss:
[01:07] – Rich’s background and why great communication is the foundation of great connections.
[10:21] – Rich’s career challenges in the financial industry and what led him to the idea for Quik!.
[18:30] – Why going fully digital is a challenge for many firms.
[24:26] – The importance of technology, data, and automation.
[32:15] – Rich’s passions and interests outside the financial industry.
Key Takeaways
Listen to your clients and truly understand their needs, fears, and goals. This not only results in better connections but also enables financial advisors to provide more personalized services.
Positivity and optimism can be powerful elements in achieving success. Mirror back to people their potential and inspire them to be their best selves.
Don’t underestimate the importance of technology. Data standardization can be a major hurdle for advisors. Look for ways to automate so you can focus on the most important tasks and relationships.
Constantly improve communication skills. Advisors should always be students of communication. Effective communication with clients builds trust and helps advisors understand their clients better.
Quotes
“I’m always going to be a student of communication because it’s a skill that we are constantly using throughout our life and we can always build upon.” – Rich Walker
“I believe everybody can do what they set their mind to. I want people to believe in themselves more and do their best. So, I’m always the cheerleader.” – Rich Walker
“There are three stages of listening. There’s listening for my turn to say what’s next. There’s listening to understand what you said. And then there’s connected listening, active listening, where I’m truly digesting what’s important to you.” – Rich Walker
Links
Rich Walker on LinkedIn
Quik!
The 7 Habits of Highly Effective People by Stephen Covey
Aaron Klein
Arbor Day Foundation
Connect with our hosts
Milemarker.co
Kyle on LinkedIn
Jud on LinkedIn
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Technology has transformed the financial advisory industry in recent years.…
Practice Management
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Investing
View MoreEpisode 064: Traditionally, value propositions are centered on beating the market and outperforming benchmarks. However, these factors often fail to deliver consistent and reliable results for investors. To address this challenge, Fairway Wealth Management aims to provide reliable results by focusing on factors investors can control. These include tax efficiency, cost management, and behavioral guidance.
This week, Kyle talks with Mark Weiskind, Founding Partner and President at Fairway Wealth Management. Mark helped found the firm in 2002 to provide clients with world-class, high-touch, completely independent, and objective advice. Kyle and Mark discuss delivering reliable value, how smaller firms can provide comprehensive financial planning without joining big platforms or consolidators, and how technology is essential in streamlining processes and enhancing client experience.
In this episode:
[03:03] – Mark’s money moment
[07:02] – How Mark defines reliable value
[10:20] – Tax alpha
[16:11] – Fees and holistic advisory services
[19:39] – How Fairway provides comprehensive service without joining big platforms
[25:24] – The challenges of small boutique firms
[31:55] – Mark’s thoughts on the future of the RIA industry
[35:29] – Mark’s Milemarker Minute
Key Takeaways
Reliable value is built on factors that are controllable and consistent, such as tax efficiency, cost reduction, and behavioral guidance.
Tax optimization is a key area where advisors can provide significant client value.
Technology is a valuable tool but should be used strategically to enhance efficiency and client experience.
Smaller firms can compete with big names in the industry by offering personalized service, building strong relationships, and investing in employee development.
Quotes
[07:07] – “For most firms in our industry, the value proposition is based on aspirational concepts and predictions and things investors and advisors don’t have any control over. We focus on things that are controllable, where the value is reliable and consistent.” ~ Mark Weiskind
[21:16] – “I think the way to succeed is by being hands-on and really just serving the heck out of your clients. As a small boutique firm, if you can do that in an exceptional way, you can truly differentiate yourself as an advisor.” ~ Mark Weiskind
[26:04] – “One of the challenges of being a smaller firm is that we don’t always spend enough time or don’t have the resources to really focus on that tech stack. As more and more technologies emerge, it’s hard to keep up.” ~ Mark Weiskind
Links
Mark Weiskind on LinkedIn
Fairway Wealth Management
Deloitte
Connect with our hosts
Milemarker.co
Kyle on LinkedIn
Jud on LinkedIn
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Turncast helps your company grow by producing top-quality content and fostering transformative conversations. We specialize in content generation, podcasting, digital strategy, and audience growth for fintech and financial services companies. Learn more at Turncast.com.
Most Viewed
Episode 127: This week, Kyle Van Pelt talks with Matt Regan, President at Wealthcare. With more than two decades in the financial services industry, Matt has helped build several transformative business models, including launching the retail brokerage and OpenIPO system at WR Hambrecht+Co. His work has consistently focused on scaling world-class organizations with a strong commitment to the client experience.
Kyle talks with Matt about building scalable, sustainable advisory businesses at the intersection of technology and operations. Matt shares his journey into wealth management, the evolution of Wealthcare from planning software to a full-service platform, and how standardized systems drive organic growth and enterprise value. They dive into affiliation models, M&A strategy, talent challenges, and the future of advice in an AI-driven world—especially for emerging advisors and smaller clients.
In this episode:
(00:00) – Intro
(02:44) – Matt’s money moment 0.
(03:58) – Wealthcare’s origin story
(06:20) – Wealthcare’s affiliation model
(12:24) – Common pitfalls in M&A
(14:04) – The talent gap and finding Gen 2 successors
(15:33) – Matt’s thoughts about the future of M&A
(19:34) – What it takes to build a firm from $0 to $100M in today’s market
(22:47) – The role of AI in serving HENRYs (High Earners, Not Rich Yet)
(26:50) – Why soft skills are the new hard currency
(28:27) – Matt’s outlook on the future of the industry
(32:37) – Matt’s Milemarker Minute
Key Takeaways
Standardization creates enterprise value. A repeatable operating system is what turns an advisory practice into a real business. Consistency across planning, investments, client service, and operations becomes your biggest growth lever.
Tech-enabled platforms only matter if the tech actually supports the advisor’s workflow. A true tech platform is not a stack of tools. It’s a single operating system that connects planning, investments, trading, and service in one experience.
“Date before you marry” might be the future of advisor M&A. Affiliation provides an opportunity for advisors to integrate systems, see the culture, and test-fit a partner long before selling the firm. It reduces regret and increases alignment.
Not every acquisition is a good acquisition. Great M&A means buying businesses you can meaningfully improve.
Quotes
“What the founder of this firm preached was that you should do things in a very systematic, repeatable way. It’s the only way you scale. It’s the only way you grow organically.” ~ Matt Regan
“[Being a financial advisor] takes an incredible amount of resilience and aggressive dedication to building a business. And it’s not for the faint of heart.” ~ Matt Regan
“Progress empowers the people who work for us here and creates career paths and a valuable professional life for Wealthcare’s employees. I care deeply about the people who work here. And I want to see them not only succeed financially, but become happy people.” ~ Matt Regan
Links
Matt Regan on LinkedIn
Wealthcare Capital Management
Wells Fargo
Fidelity Investments
Orion Advisor Solutions
Charles Schwab
Morgan Stanley
The Passenger
Blood Meridian
Connect with our hosts
Milemarker.co
Kyle on LinkedIn
Jud on LinkedIn
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This week, Jack Sharry talks with Arthur Worthington, Managing Director…
Recruiting, Optimizing and Fighting for Impactful Wealth Management Firms in 2026
Episode 126: This week, Kyle Van Pelt talks with Sarah Simmer, Partner and Senior Wealth Advisor at Heritage Wealth Advisors. Sarah delivers customized wealth management and tax planning services to individuals and families, with a special focus on multi-generational households.
Sarah talks with Kyle about what world-class client experience truly requires, especially for ultra-high-net-worth families. She shares the tactical side of scaling a white-glove firm, highlighting the importance of rigorous client segmentation, the courage to have difficult fee conversations, and how to use data to determine exactly who you should and shouldn’t be serving.
In this episode:
(00:00) – Intro
(03:10) – Sarah’s money moment
(06:11) – How Sarah’s mother influenced her career in wealth management
(09:13) – How an auditor’s mindset translates to serving high-net-worth families
(10:30) – What client experience means for ultra-high-net-worth families
(13:16) – How Sarah uncovers and manages client expectations
(17:55) – Why proactively discussing fees can reinforce value
(22:46) – How Heritage scales white-glove service to ultra-high-net-worth clients
(30:03) – How a scaled white-glove service feels personalized
(34:08) – Sarah’s outlook on the future of the financial services industry
(36:22) – Sarah’s Milemarker Minute
Key Takeaways
Client experience is not a deliverable. It’s the whole relationship. The client’s perception is the reality. Leaders need a consistent feedback loop to ensure the experience matches the intent.
Audit-trained minds bring hidden superpowers. Learning how to learn quickly and diagnose problems is often more valuable than specific industry knowledge.
Don’t fear the fee conversation. While many leaders shy away from this topic, proactively raising it allows you to realign expectations. If the client hesitates on the fee, it’s an immediate signal that there is a disconnect in the perceived value of the service being delivered.
Providing white-glove services at scale requires a personalized approach. White-glove service feels impossible to scale unless you define exactly who fits in which bucket.
Quotes
“At the end of the day, we’re a people business, so the client’s experience is their reality. We can think we’re doing a fantastic job, but if the client has a terrible experience through all of it, we’re not going to stay in business.” ~ Sarah Simmer
“If you believe in the value you’re providing to your clients, you shouldn’t be scared to check in with them on how that fee feels.” ~ Sarah Simmer
“If we can focus on making the information and the story we’re trying to get to the client more aligned with the types of experiences they enjoy, that’s the goal.” ~ Sarah Simmer
Links
Sarah Simmer on LinkedIn
Heritage Wealth Advisors
PwC
Dee Ann Remo
KPMG International
McKinsey
A Bit Much
Northanger Abbey
Connect with our hosts
Milemarker.co
Kyle on LinkedIn
Jud on LinkedIn
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Produce game-changing content with Turncast
Turncast helps your company grow by producing top-quality content and fostering transformative conversations. We specialize in content generation, podcasting, digital strategy, and audience growth for fintech and financial services companies. Learn more at Turncast.com.
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