In the Money

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 [https://www.linkedin.com/in/dan-o-brien-9701732/] * Website: AssetMark [https://www.assetmark.com/] Connect with Rusty Sommer: * Rusty.sommer@flyerft.com  [http://Rusty.sommer@flyerft.com] * LinkedIn: Rusty Sommer [https://www.linkedin.com/in/rustysommer/] * Flyer Financial Technologies [https://flyerft.com/] * LinkedIn: Flyer Financial Technologies [https://www.linkedin.com/company/flyerft] * Twitter: Flyer_FT [https://twitter.com/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.

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 [https://www.linkedin.com/in/trasha-schwendener-0469363b/] * Website: F2 Strategy [https://www.f2strategy.com/] Connect with Rusty Sommer: * Rusty.sommer@flyerft.com  [http://Rusty.sommer@flyerft.com] * LinkedIn: Rusty Sommer [https://www.linkedin.com/in/rustysommer/] * Flyer Financial Technologies [https://flyerft.com/] * LinkedIn: Flyer Financial Technologies [https://www.linkedin.com/company/flyerft] * Twitter: Flyer_FT [https://twitter.com/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.

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  [http://Rusty.sommer@flyerft.com] * LinkedIn: Rusty Sommer [https://www.linkedin.com/in/rustysommer/] * Flyer Financial Technologies [https://flyerft.com/] * LinkedIn: Flyer Financial Technologies [https://www.linkedin.com/company/flyerft] * Twitter: Flyer_FT [https://twitter.com/flyer_ft] Connect with Matt Sonnen: * LinkedIn: Matt Sonnen [https://www.linkedin.com/in/mattsonnen/] * Coldstream Wealth Management [https://www.coldstream.com/] * The COO Roundtable Podcast [https://www.coldstream.com/the-coo-roundtable-podcast/] * COO Society [https://coosociety.com/] 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.

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  [http://Rusty.sommer@flyerft.com] * LinkedIn: Rusty Sommer [https://www.linkedin.com/in/rustysommer/] * Flyer Financial Technologies [https://flyerft.com/] * LinkedIn: Flyer Financial Technologies [https://www.linkedin.com/company/flyerft] * Twitter: Flyer_FT [https://twitter.com/flyer_ft] Connect with Chip Kispert: * LinkedIn: Chip Kispert [https://www.linkedin.com/in/chip-kispert-3573274/] * Beacon 100% Better Everyday Podcast [https://podcasts.apple.com/ca/podcast/beacon-1-better-everyday/id1830535959] * Beacon Strategies, LLC [https://www.beaconstrategiesllc.com/] 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.

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  [http://Rusty.sommer@flyerft.com] * LinkedIn: Rusty Sommer [https://www.linkedin.com/in/rustysommer/] * Flyer Financial Technologies [https://flyerft.com/] * LinkedIn: Flyer Financial Technologies [https://www.linkedin.com/company/flyerft] * Twitter: Flyer_FT [https://twitter.com/flyer_ft] Connect with Benoit Fleury: * LinkedIn: Benoit Fleury [https://www.linkedin.com/in/benoit-fleury-0526b43/?originalSubdomain=ca] * Website: d1g1t Inc [https://www.d1g1t.com/] 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.