In the Money

Flyer Financial

Welcome to In the Money with Flyer Financial Technologies, the company that builds cutting-edge technology designed to solve asset and wealth management firms’ toughest trading workflows. In this podcast, we help advisors and asset managers understand how technology is transforming the WealthTech sector. We’ll cover how to leverage technology for faster, smarter investment decisions, mega-trends, and more. Tune in to hear our guest experts explore the biggest challenges and opportunities in the WealthTech game.

  1. MAR 4

    Growth Through Strategic Partnerships with Dan O’Brien (Ep. 33 | Pt. 2)

    ​​Growth is on every trust leader’s mind, but for many firms, scaling creates operational drag that pulls their best people away from client relationships. How do you build capacity for growth without sacrificing the service quality that defines your firm? How do you compete when talent constraints and market complexity make it harder to do everything in-house? In our third conversation from the Association of Trust Organizations annual conference, Rusty Sommer speaks with Dan O’Brien, Business Development Officer, Financial Institutions, at AssetMark, about the paradox facing today’s trust companies. Dan shares strategies for leveraging partnerships to unlock operational efficiency, explaining how firms can access institutional-grade investment solutions, reduce time spent executing business, and create capacity for advisors to focus on what matters most: building relationships and serving clients effectively. Dan discusses: Why trust companies struggle with growth despite strong markets and how operational complexity holds them back The power of client segmentation and why 70-80% of next-generation beneficiaries change advisors How integrated technology platforms with CRM, planning, and investment tools create workflows that scale What outsourced investment models actually look like and why they don’t mean losing control or client trust Why community banks face unique talent challenges and how variable cost partnerships solve location constraints And more! Connect with Dan O’Brien: LinkedIn: Dan O’Brien Website: AssetMark Connect with Rusty Sommer: Rusty.sommer@flyerft.com  LinkedIn: Rusty Sommer Flyer Financial Technologies LinkedIn: Flyer Financial Technologies Twitter: Flyer_FT About our Guest:  Dan O’Brien is a dynamic financial services sales executive with extensive leadership experience, specializing in consultative sales strategies that create win-win scenarios for buyers and sellers. He is adept at strategic thinking, creative solutions, and effective communication, with a deep understanding of the financial intermediary, M&A, bank trust and retirement marketplace. Dan possesses a proven track record managing complex sales cycles, interfacing with C-suite executives, and leading cross-functional, geographically dispersed teams. His exceptional presentation and negotiation skills, coupled with a strong work ethic and entrepreneurial spirit, have consistently delivered solutions that achieve results.

    18 min
  2. JAN 14

    Reclaiming Time and Clarity Through Better Technology with Trasha Schwendener (Ep. 32 | Pt. 1)

    Technology is meant to create space for deeper thinking, yet many firms feel more rushed than ever. Busy workflows, manual processes, and unclear priorities often crowd out time for clients and strategy. In this episode, Rusty Sommer speaks with Trasha Schwendener, Managing Director at F2 Strategy, at the American Trust Organization’s (ATO) annual conference about how trust organizations can rethink technology to give people time back. They explore where automation actually helps, why process matters more than tools, and how firms can define their identity as client expectations shift. The conversation also covers onboarding, communication, and how modern portals shape relationships across generations. Key takeaways: Why being a thought-driven industry still leaves little room for thinking How onboarding, reviews, and distributions drain advisor time The role of process before automation in trust organizations Defining firm identity between trust company and RIA models Using technology to strengthen communication and client experience And more! Connect with Trasha Schwendener: LinkedIn: Trasha Schwendener Website: F2 Strategy Connect with Rusty Sommer: Rusty.sommer@flyerft.com  LinkedIn: Rusty Sommer Flyer Financial Technologies LinkedIn: Flyer Financial Technologies Twitter: Flyer_FT About our Guest:  Trasha Schwendener is a proven relationship and sales leader with close to 20 years experience in client management, wealth management, and fintech solutions. Her primary focus has been sales, training, and developing strategic client and partner relationships. Trasha honed her expertise through roles with trust accounting software and private wealth management firms, where she worked with bank trust departments, independent trust companies, family offices, and foundations. She is passionate about working in a continuous learning environment and helping others grow professionally. In her personal time, Trasha enjoys being with her family and volunteering with Top of the Lake Rotary. She lives in Charlotte, North Carolina.

    20 min
  3. 10/09/2025

    Operational Leadership with Matt Sonnen: Turning Practices into Enterprises (Ep. 31)

    Operations is the hidden engine that turns ambition into enterprise growth. Yet, for many firms, it’s overlooked until bottlenecks appear. In this episode, Rusty Sommer speaks with Matt Sonnen, Chief Operating Officer of Coldstream and host of the COO Roundtable podcast, about the pivotal role of operations in wealth management firms. Matt shares insights from his unique journey as a consultant and operator, the importance of community among COOs, and how process, people, and technology align for growth. Key takeaways: His career path from Focus Financial to running his own consultancy to becoming COO at Coldstream Why he founded COO Society and how it builds peer support and education for operations leaders Why process, not technology, is often the real source of trading and operational errors The dangers of chasing “more clients” versus focusing on deeper relationships with fewer clients How COOs must balance profitability, tech platforms, human capital, and AI adoption to prepare firms for sustainable growth And more! Connect with Rusty Sommer: Rusty.sommer@flyerft.com  LinkedIn: Rusty Sommer Flyer Financial Technologies LinkedIn: Flyer Financial Technologies Twitter: Flyer_FT Connect with Matt Sonnen: LinkedIn: Matt Sonnen Coldstream Wealth Management The COO Roundtable Podcast COO Society About Our Guest:  Matt Sonnen has over 25 years of experience in the financial services industry. As Chief Operating Officer, Matt manages all aspects of Coldstream’s operational platforms to identify opportunities to scale and systematize processes ensuring capacity for the firm’s continued growth. In addition, Matt will also oversee the firm’s Information Technology, Performance Reporting, Client Service, and CRM efforts. Before joining Coldstream, Matt was the Founder and CEO of PFI Advisors – a firm dedicated to consulting registered investment advisor (RIA) owners on best infrastructure and culture practices. Matt has been a thought-leader in our industry – publishing over 270 practice management articles, research papers, and podcasts. In June 2021, he launched The COO Society to create a community of RIAs centered around coaching operations professionals. Matt learned the ins and outs of the wirehouse model at Merrill Lynch in the late 1990s.  Matt left Merrill in 2005, and a few years later, he was introduced to the RIA marketplace, helping build the infrastructure for Luminous Capital prior to its founding in 2008.  As COO and CCO at Luminous, he navigated technology and compliance challenges as the firm grew from $1.7 billion in assets to nearly $6 billion in less than five years.  Luminous Capital was sold to First Republic Bank for more than $100 million in 2012, after which Matt headed to Focus Financial Partners in New York City, where he helped partner firms streamline operations and improve back-office efficiencies. Matt graduated from the University of California, Los Angeles with a Bachelor of Arts in Economics. He currently resides in California with his wife, Reese (Larissa), and son, Luke.

    24 min
  4. 09/18/2025

    Cutting Through WealthTech Noise with Chip Kispert (Ep. 30)

    Wealth management firms are drowning in technology, but which tools truly matter? In this episode of In The Money, host Rusty Sommer talks with Chip Kispert, Managing Partner of Beacon Strategies, about separating hype from value in AI, compliance, and alternatives. They explore how firms can scale effectively, adopt tech without fatigue, and prepare for the next wave of client expectations. Key Points: How advisors face tech overload and why plug-and-play solutions that simplify workflows are gaining traction Real AI use cases like estate planning, compliance surveillance, and portfolio monitoring versus “AI noise” The challenges of Rep-as-PM, the role of benchmarks, and how tech supports customized portfolios Compliance concerns around AI, the urgent need for firm-level AI policies, and regulatory expectations The growing demand for alternative investments, hurdles in adoption, and why scalability is the ultimate catalyst for firm-wide change And more! Connect with Rusty Sommer: Rusty.sommer@flyerft.com  LinkedIn: Rusty Sommer Flyer Financial Technologies LinkedIn: Flyer Financial Technologies Twitter: Flyer_FT Connect with Chip Kispert: LinkedIn: Chip Kispert Beacon 100% Better Everyday Podcast Beacon Strategies, LLC About Our Guest:  Chip Kispert is the Founder and Managing Partner of Beacon Strategies, LLC. He has over 20 years of experience in the broker-dealer and asset management industries. Chip specializes in developing and implementing data management-centric supply strategies, focusing on infrastructure evolution. Before founding Beacon, he was the Vice President of Sales at Trust Company of America and held senior sales and business development roles at Fidelity Investments for four years.

    27 min
  5. 08/28/2025

    Elevating Advisor and Client Experiences Through Wealth Tech Innovation with Benoit Fleury (Ep. 29)

    Wealth management is evolving rapidly, and technology is no longer just a support tool; it’s a driver of strategic growth. How can advisors deliver truly personalized client experiences while running more efficient businesses? How can tech stacks attract top talent and position firms for the future? In this episode of In The Money, Rusty Sommer talks with Benoit Fleury, Chief Product Officer and co-founder of d1g1t, about how open architecture, AI integration, and institutional-grade analytics are redefining wealth management. Benoit shares practical insights on personalization at scale, operational efficiency, and the secure use of AI to transform client and advisor interactions. Key highlights include: Why elevating the advisor experience with better tech directly enhances the client experience How personalization at scale is essential for engaging different types of investors The role of institutional-grade analytics in building trust and deeper relationships How integrated, cloud-based architectures streamline operations and remove inefficiencies The secure integration of AI to power automation, contextual reporting, and proactive portfolio management And more! Connect with Rusty Sommer: Rusty.sommer@flyerft.com  LinkedIn: Rusty Sommer Flyer Financial Technologies LinkedIn: Flyer Financial Technologies Twitter: Flyer_FT Connect with Benoit Fleury: LinkedIn: Benoit Fleury Website: d1g1t Inc About Our Guest:  Benoit Fleury leads the design, development, and implementation of the d1g1t wealth management platform. A Fintech Entrepreneur and product guru with a passion for building advanced investment and risk management solutions, he brings over 20 years of experience in projects with over 100 financial institutions in North America, Europe, Latin America, and Asia, including investment banks, asset managers and hedge funds, insurance companies, exchanges, and wealth management firms. Benoit was a co-founder and the Head of R&D, Financial Engineering, and Products at R² Financial Technologies, acquired by S&P Capital IQ. Prior to R², He was at Algorithmics (acquired by IBM), where he led the development of its managed services and SaaS market, and credit risk platform. Benoit holds a Master of Science and Business Administration from the University of British Columbia and is a CFA charter holder.

    28 min
  6. 06/26/2025

    Balancing Operational Efficiency with a Strong Brand Story for Growth with Randy Lambert and Joe Steuter (Ep. 28)

    Are you struggling to articulate your brand’s story or connect with clients in a meaningful way? Discover the art and science behind building a powerhouse brand that supports growth and client trust. In this episode, Rusty Sommer speaks with Randy Lambert and Joe Steuter from Intention.ly about transforming growth through strategic brand messaging. They explore the map to supercharge growth and build a cohesive brand narrative in the ever-evolving financial industry. The conversation highlights practical insights from decades of industry experience, emphasizing the balance between operational efficiency and compelling storytelling. Learn how understanding customer needs, simplifying your brand message, and maintaining internal alignment can differentiate your firm in a competitive landscape. Randy and Joe discuss:  (03:09) The importance of building strong customer relationships and uncovering their pain points (04:34) Why simplified storytelling boosts engagement and growth (07:55) Navigating brand messaging and organizational alignment during mergers and acquisitions (10:36) The role of core values in managing growth and cultural alignment (18:23) How brand impacts the recruitment and retention of advisors (20:39) Tactics for building a strong internal brand that drives external growth We unravel the elements that make a brand powerful and trustworthy, both inside and out. Tune in and refine your own brand strategy! Connect with Randy Lambert: Intention.ly LinkedIn: Randy Lambert Connect with Joe Steuter: Intention.ly LinkedIn: Joe Steuter Connect with Rusty Sommer: Rusty.sommer@flyerft.com  LinkedIn: Rusty Sommer Twitter: @RustySommer Flyer Financial Technologies LinkedIn: Flyer Financial Technologies Twitter: Flyer_FT About our Guests:  Randy Lambert is Intention.ly’s EVP and Head of RIA Solutions. With three decades in the Registered Investment Advisor (RIA) and FinTech space, Randy Lambert has a proven track record of scaling operational processes to manage elite-level growth. By comprehensively understanding the RIA operational process, Randy can enhance processes and provide value that creates a great client and employee experience. His passion is leading a talented team that supports our mission to help every client maximize their Orion experience. Their team does this by championing a proven process that empowers advisors to focus on their top priorities with the highest impact for the advisory firm. In business and in life, the art of the message matters most when building a connection. As the Chief of Communications at Intention.ly, Joe Steuter brings 20 years of brand consulting experience in message development, brand building, and communications strategy to inform, engage, and inspire action. Throughout the past two decades, his work has impacted financial services in varying degrees, from helping independent financial advisors mold their personal stories to building brands at the firm level and playing a central role in articulating brand messages for one of the country’s fastest-growing RIAs in the country.

    39 min
  7. 06/09/2025

    Unlocking Data Superpowers for RIAs: Thrive in the Age of Information (Ep. 27)

    What if your financial data could talk?  Would it reveal new secrets about your clients, business, and the future of wealth management? In this engaging episode of “In the Money,” host Rusty Sommer dives deep into the age of data with Oleg Tishkevich, the visionary founder and CEO of INVENT®. Together, they explore the transformative power of data integration in reshaping the wealth management landscape. Listen in as Rusty and Oleg discuss: (03:07) The complexities of data scattered across multiple systems and the role of AI in creating cohesive conversations with your data. (06:42) How Invent is pioneering an ecosystem that integrates various financial systems to enhance advisor-client interactions. (12:11)Oleg’s insights into the evolving RIA industry and why customizable, client-centric solutions are the future. (14:42)The critical role of technology in adapting and redefining the advisor-client relationship. (28:43) Oleg’s prediction for 2025 and how each firm might become its own artist in crafting unique client experiences. Connect with Oleg Tishkevich: LinkedIn: Oleg Tishkevich Invent® Connect with Rusty Sommer: Rusty.sommer@flyerft.com  LinkedIn: Rusty Sommer Flyer Financial Technologies LinkedIn: Flyer Financial Technologies Twitter: Flyer_FT About Oleg Tishkevich:  Oleg Tishkevich is a visionary technology entrepreneur and the founder and CEO of Invent®, a cloud-native software development and consulting firm serving the wealth management and real estate industries. With a focus on systems design, data architecture, and digital experiences, Invent® helps enterprise firms and registered investment advisors (RIAs) modernize their technology infrastructures  Prior to founding Invent®, Tishkevich established Finance Logix, a next-generation financial planning software company known for its engaging mobile planning app, Retire Logix. The app was recognized as the “Best Money Move” by Money magazine and voted the number one mobile app for advisors. Finance Logix was acquired by Envestnet in 2015, where Tishkevich served as Chief Technology Officer for Financial Planning.​ Throughout his career, Tishkevich has been instrumental in delivering custom firm-wide solutions for major companies such as Wells Fargo, Bank of America/Merrill Lynch, AssetMark, and Janney Montgomery Scott. His leadership continues to drive innovation in the financial technology sector, helping firms transition to cloud-native platforms and enhance their digital capabilities.

    30 min
  8. 05/28/2025

    AI and Financial Advisors: Why 2025 Will Be a Turning Point with John O’Connell (Ep. 26)

    How is Artificial Intelligence reshaping the wealth management industry? In this episode, Rusty Sommer sits down with John O’Connell, CEO and Founder of The OASIS Group, at the bustling Market Council Summit in Las Vegas. Together, they explore how AI is rapidly transforming the way advisors serve clients, from streamlining workflows to enhancing personalization at scale. Their conversation highlights both the opportunities and challenges of integrating AI into financial services, while emphasizing the continued importance of human expertise in the process. Rusty and John discuss: (01:56) The rise of AI and its prevalence in conferences today  (03:34) How note-taking tech is gaining traction in wealth management  (04:40) The evolving AI wealth tech map with over 80 firms and growing  (07:57)Enhancing the client experience with AI and the importance of having humans in the loop  (14:13) The future of financial advice aided by AI and its potential to increase productivity  Connect with John O’Connell: LinkedIn: John O’Connell The Oasis Group LinkedIn: The Oasis Group Connect with Rusty Sommer: Rusty.sommer@flyerft.com  LinkedIn: Rusty Sommer Flyer Financial Technologies LinkedIn: Flyer Financial Technologies Twitter: Flyer_FT About our Guest:  John O’Connell has more than 30 years of leadership experience in both emerging businesses and mature, established organizations. He started his career designing and developing financial applications at Merrill Lynch and KPMG Peat Marwick. He was a member of the team for an IPO, sale of a firm, and packaging 2 other firms for sale. He held North American leadership positions at Oracle for over 8 years. He was the president of a FinTech firm and held C-level customer-facing roles at two global, publicly traded companies. John is the Founder and Chief Executive Officer for The Oasis Group. A firm specializing in helping wealth management and technology firms to solve their most complex challenges. The Oasis Group helps firms with technology selection and implementation, sales processes and strategy, and processes to attract, sell, propose, onboard, and service new clients.

    34 min

Ratings & Reviews

5
out of 5
2 Ratings

About

Welcome to In the Money with Flyer Financial Technologies, the company that builds cutting-edge technology designed to solve asset and wealth management firms’ toughest trading workflows. In this podcast, we help advisors and asset managers understand how technology is transforming the WealthTech sector. We’ll cover how to leverage technology for faster, smarter investment decisions, mega-trends, and more. Tune in to hear our guest experts explore the biggest challenges and opportunities in the WealthTech game.