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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Produce game-changing content with Turncast
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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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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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This week, Jack Sharry talks with Sneha Shah, Executive Vice…
Episode 133: This week, Kyle Van Pelt talks with Jennifer Goldman, Founder and Strategic Operations Transformer and Integrator at My Virtual COO. Jen is an operations expert with 30 years of experience helping 1,000+ service businesses to thrive.
Jen talks with Kyle about what it really takes to run a profitable, scalable advisory firm. From defining what makes a truly great operator to navigating the messy middle of firm growth, Jen shares practical insights on constellation thinking, building operational leaders, and making hard profitability decisions. She also dives into the emotional and structural crossroads firms face as they scale, the evolving role of technology and AI in operations, and why clean data and strong systems still require human ownership.
In this episode:
(00:00) – Intro
(03:33) – Jen’s money moment
(06:39) – What it takes to be a great operator
(08:55) – How “constellation thinking” works
(12:19) – Balancing SOPs with creativity in operations
(14:42) – The profitability challenges in the growth process
(16:57) – What determines whether you should build or join a platform
(21:42) – How Jen utilizes AI in her work
(23:01) – Why AI can’t replace CRMs
(27:27) – Why it’s important to have clean CRM data
(32:36) – What it takes to build a process for advisors and investors
(37:35) – What Jen looks for when engaging with advisors
(39:53) – Jen’s outlook on the future of the financial services industry
(42:51) – Jen’s Milemarker Minute
Key Takeaways
Think like an operator. Great operators don’t work in silos. They practice “constellation thinking”—understanding how a change in one area (people, process, technology, profitability) impacts the rest of the organization. Sustainable growth comes from seeing those connections before making decisions.
Progress beats perfection when scaling a business. Operators must act with imperfect information and accept small failures along the way. Waiting for perfect data or perfect conditions slows growth. Progress, iteration, and course correction are what move firms forward.
Your growth path depends on how well you’ve built your team. When firms hit major crossroads, whether to scale into a platform or join one, the deciding factor is often people. Leaders who develop decision-makers and future executives create optionality—those who don’t often feel stuck or fatigued.
Systems create stability, but creativity keeps operations moving. SOPs and structured processes are essential for consistency, but operators must also stay flexible and creative when reality doesn’t follow the playbook. Balancing structure with adaptability is key to running a resilient firm.
Quotes
“Your data is so important. It’s telling you stories. If you don’t keep it clean, it’s not going to tell you what you need to do next with the business.” ~ Jennifer Goldman
“Businesses cannot scale unless they’re constantly and continuously improving. It doesn’t have to be a heavy lift. Just shine a light, make a small change, and keep going.” ~ Jennifer Goldman
“This clarity around data and understanding, pulling it together, and using it effectively is so important. It allows you to have more touch with the people around you, whether it’s clients or the advisor teams.” ~ Jennifer Goldman
Links
Jennifer Goldman on LinkedIn
My Virtual COO
The Let Them Theory
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.
Episode 132: This week, Kyle Van Pelt talks with Andrew Evans, Chief Executive Officer of Rossby. Before Rossby, Andrew served as Executive Vice President at TAG Advisors and as a Securities Principal at Cambridge Investment Research.
Andrew talks with Kyle about entrepreneurship, growth, and designing better businesses. With a background in musical theater and a career that spans mortgage brokerage and financial advising, Andrew shares the parallels between creative careers and financial services, why repeatable processes beat flashy marketing plans, and how thoughtful design can transform the advisor experience.
In this episode:
(00:00) – Intro
(01:39) – Andrew’s money moment
(04:55) – Parallels between mortgage brokerage and financial advising
(07:07) – How Andrew built his early book of business
(11:50) – The financial-planning version of a closing credit
(13:07) – Redefining traditional conferences with The Unconference
(16:41) – How The Unconference generates the best business ideas
(19:43) – What it means to drive business forward
(25:04) – The concept of “less but better” in business and technology
(28:39) – Designing intuitive systems and reducing operational friction
(32:22) – Creativity, patience, and building differently
(35:16) – Andrew’s outlook on the future of the financial services industry
(44:13) – Andrew’s Milemarket Minute
Key Takeaways
Whether you’re selling a mortgage or a financial plan, technical skills are just the baseline. The real growth comes from mastering interpersonal and psychological engagement and understanding the emotional drivers behind a client’s financial decisions.
Plan a repeatable process. Growth becomes sustainable when your marketing and operations are simple enough to execute consistently every day.
Design for less but better. Complexity is the enemy of efficiency. In leadership and tech, aim for intuitive design that reduces clicks and surprises. Your goal should be to create a “source of truth” for data that lets your team spend less time on administration and more time on high-value work.
The best ideas at any conference or meeting rarely come from the person at the podium. They happen in the hallways, over coffee, or during shared activities.
Quotes
“Nobody gains great ideas by sitting there and being lectured at. It doesn’t happen. The best stuff happens in the conversations on the edges.” ~ Andrew Evans
“You can’t satisfy everyone. Whatever you’ve decided on for your firm’s tech stack, someone is going to hate it. So, design for the firm’s data integrity first, then let them pick their tools.” ~ Andrew Evans
“Focus on where your practice’s source of truth is. That’s where you really need your agent. Keep it focused. Keep it tight.” ~ Andrew Evans
Links
Andrew Evans on LinkedIn
Rossby Financial
Raymond James
The Unconference
Kelsey McKenna
Seeds Investor
Midquel McClendon
Capital Square
The Design of Everyday Things
Redtail Technology
Wealthbox
Advisor360
eMoney Advisor
The Lord Of The Rings
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.
This week, Jack Sharry talks with Garrett Beam, Head of…
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