Jason Early is the Founder and CEO of RISR, a wealthtech platform that helps financial advisors support business owners with business valuation, succession, exit planning, and risk clarity. With extensive experience in financial services, he has dedicated his career to building innovative tools and solutions for advisors and the clients they serve. RISR was recognized by Investment News as Best New Technology, and Jason was named to the publication's 40 Under 40. Before founding RISR, he held advisory leadership roles and served as President of a wealth technology firm specializing in private company valuation services.

Business owners often have most of their wealth tied up in their company — but many don't know what their business is really worth or how it fits into their retirement, estate, and legacy plans. Advisors frequently treat the business like a plug-in number, which can lead to misguided planning and missed opportunities. How can advisors bring real clarity, reduce risk, and help business owners plan for a successful exit?

Jason Early, a wealthtech founder and longtime financial services leader, explains that effective advice starts with true business clarity: establishing the current value of the business and the value it needs to reach to support goals like retirement and philanthropy. He recommends guiding owners to identify and mitigate both equity risk and operational risk. Jason also emphasizes planning early, operating the business as if it's always ready to sell, and building a succession or exit plan since most businesses don't successfully transact.

In this episode of The Customer Wins, Richard Walker interviews Jason Early, Founder and CEO of RISR, about helping advisors deliver better outcomes for business owners. Jason shares insights on business valuation clarity, risk reduction, and exit planning. He also discusses tax planning trends, how AI is changing software building, and the mentors who shaped his leadership.

Dan Zitting is the CEO of Nitrogen, a platform that empowers advisors by creating more engaging, confidence-building client conversations. He is a longtime SaaS entrepreneur and operator with a background in building software in governance, risk, and compliance (GRC). Before Nitrogen, Dan founded Workpapers.com and later led Galvanize through significant growth, culminating in its $1 billion acquisition by Diligent. At Nitrogen, he focuses on using modern technology to help advisors deliver more personalized guidance so clients can invest and live fearlessly.

Financial advice can feel overwhelming and emotional, especially when clients are unsure whether they're making the right decisions or if their long-term plans are truly secure. Advisors, in turn, often struggle to translate complex topics like risk, taxes, and income planning into conversations that feel clear, personalized, and confidence-building. How can advisors strengthen client trust while scaling those high-impact moments across a growing book of business?

Dan Zitting, a SaaS executive and enterprise software leader with deep expertise in governance, risk, and compliance platforms, shares how advisors can elevate client outcomes through better engagement and communication. He emphasizes meeting clients where they are emotionally, using structured talk tracks to prepare for meaningful conversations, and presenting recommendations in a professional, visual format that clients can actually absorb. Dan also highlights how modern AI can reduce prep time by automating data ingestion, uncovering hidden planning insights from documents like brokerage statements and tax returns, and helping advisors focus more on guidance and trust rather than manual workflow.

In this episode of The Customer Wins podcast, Richard Walker interviews Dan Zitting, CEO of Nitrogen, about helping advisors create fearless client moments through better engagement and AI-powered tools. Dan discusses rebranding beyond risk tolerance, building an AI-first platform, and using tax insights to deepen planning conversations.

Richart Ruddie is the Founder of Captain Compliance, a data privacy and compliance software platform that helps organizations navigate complex data protection laws and automate compliance. He is a serial founder and entrepreneur with a track record of building and exiting successful online businesses. Richart is recognized as a privacy expert and often speaks on data privacy and regulatory risk at industry events. His work focuses on empowering companies to build trust with customers and avoid costly legal issues related to privacy.

Many organizations inadvertently expose themselves to legal risk through data privacy oversights, often despite their best efforts to comply. With regulations evolving at breakneck speed, a single misstep — such as an outdated policy or a faulty consent tool — can lead to costly lawsuits. How can your organization stay compliant and protected while continuing to scale and prioritize the customer experience?

Richart Ruddie, a passionate advocate for data privacy, tackles these very issues by offering a comprehensive software solution designed to help businesses navigate data privacy laws and prevent costly litigation. He explains how even B2B and financial services firms are at risk, emphasizing that privacy requirements aren't just about marketing — they're about protecting employee and customer data from breaches and misuse. Richart dives into real-world examples where a lack of compliance led to massive fines and job losses, illustrating the high stakes involved.

In this episode of The Customer Wins, Richard Walker interviews Richart Ruddie, Founder of Captain Compliance, about building trust and protecting businesses through innovative privacy compliance. Richart discusses not only the technical challenges of privacy but also the immense value of a customer-obsessed culture, scaling personalized service, and the importance of staying ahead of ever-evolving regulations.

Mark Ovaska is the Co-founder and CEO of Precept, an AI-driven integration platform that helps fintech companies connect to any API quickly and simplify complex data integrations. He co-founded the company to eliminate lengthy and costly integration projects, enabling teams to scale without engineering bottlenecks. Before Precept, Mark led software platform revitalization and other ventures, blending technical leadership with product strategy. His background also includes creative work in photojournalism, with work featured in major publications.

Many organizations struggle with fragmented data, sluggish integrations, and disconnected systems that create friction for both teams and customers. These challenges hinder the ability to deliver timely, personalized, and reliable customer experiences at scale. How can businesses overcome data complexity without adding more cost, time, or technical debt?

Mark Ovaska, a technology and product executive with deep experience in data platforms, integrations, and AI-driven systems, explores these issues. He explains why great customer experiences depend on connected, portable data and how standardization reduces friction and unlocks scale. Mark shares how AI can map and connect systems in real time, eliminate redundant integration work, and shift focus away from "how many integrations exist" toward readiness and flexibility. His guidance centers on treating data infrastructure as foundational plumbing that enables faster innovation, agentic workflows, and long-term growth.

In this episode of The Customer Wins podcast, Richard Walker interviews Mark Ovaska, Co-founder and CEO of Precept, about simplifying data integrations to power better customer experiences. Mark discusses AI-powered integration speed, the role of data standardization, and how modern infrastructure enables agentic workflows and scalable growth.

Molly Pierce is the CEO of Track That Advisor, a firm that helps independent financial advisors turn complex business data into clear, actionable insights to grow and scale effectively. She joined Track That Advisor in 2017 and is passionate about helping advisory teams track their metrics and reach their full potential. Molly holds a Bachelor's degree in finance and economics from Grand Canyon University.

Many advisory firms invest heavily in marketing and lead generation, yet still struggle to convert prospects or understand why their growth stalls. Without clear visibility into which processes work and which break down, teams often rely on guesswork instead of data-driven action. How can advisors simplify their metrics, cut through analysis paralysis, and focus on the numbers that actually drive growth?

Data expert Molly Pierce breaks down the core metrics that every advisor should track and explains why these leading indicators matter more than lagging ones, such as ROI. She explains how to measure stick rate, close rate, average case size, and cost per client while emphasizing the importance of serving existing clients to generate organic growth. Molly also encourages firms to compare their results with industry benchmarks, leverage pending leads, and use data as a spotlight to reveal hidden business opportunities.

In this episode of The Customer Wins, Richard Walker interviews Molly Pierce, CEO of Track That Advisor, about leveraging data to drive growth for advisory firms. Molly discusses the value of benchmark comparisons, the power of focusing on current clients, and why human connection still matters in an AI-driven world.

Colleen Bowler is the Co-founder of C&J Innovations, a firm that provides tools and assessments to help financial advisors build deeper, life-centered relationships with clients beyond just the numbers. She is the Co-creator of The Passport Package, a mindset-based assessment system bridging the human and financial sides of planning. As a Certified Financial Planner with nearly 30 years of experience, Colleen previously built a top-one-percent advisory firm managing over $500 million in assets and completed a succession plan in 2020. Outside of her business ventures, she has co-authored a book and remains committed to mentorship, generosity, and helping others achieve balance in business and life.

Many financial advisors excel at the technical side of planning but struggle to deeply understand what clients truly value. Traditional discovery meetings can feel clinical, rushed, or incomplete, leaving advisors without the human insights needed to build stronger relationships. How can advisors uncover what matters most to clients in a fast, scalable, and meaningful way?

Colleen Bowler, an expert in mindset-based financial planning and client engagement, explains how helping clients reflect on their own readiness, wellness, longevity, and partnership mindsets leads to richer conversations and deeper trust. She illustrates how five-minute assessments give advisors immediate clarity on client priorities, reduce meeting time spent on basic data gathering, and spark constructive dialogue that might not happen otherwise. Colleen encourages advisors to use these insights to celebrate client progress, strengthen household communication, and shift from purely financial conversations to holistic guidance.

In this episode of The Customer Wins, Richard Walker interviews Colleen Bowler, Co-founder of C&J Innovations, about using mindset assessments to humanize financial planning. Colleen also discusses improving advisor–client conversations, uncovering emotional patterns around money, and using AI to free up time for a deeper connection.

Josh DeTar is the EVP of Evangelism at Tyfone, Inc., a company that builds omnichannel digital banking and payments solutions for credit unions and community banks. He champions the use of technology to empower financial institutions to deepen member relationships and deliver seamless digital experiences. Josh's personal credit union journey inspired his advocacy, having experienced the impact of community financial services firsthand before transitioning to the fintech industry.

Many financial institutions promise personalized service, yet customers often feel disconnected when outdated digital tools undermine that experience. Community banks and credit unions, despite strong relationship-driven missions, struggle to compete with the speed and polish of big-bank technology. How can smaller institutions overcome technical gaps while staying true to their human-centered values?

Josh DeTar, an expert in digital banking strategy and customer experience, explains how community institutions can bridge this divide through transparency, empathy, and deliberate relationship-building. He emphasizes the importance of listening closely to customer needs, building only what adds real value, and maintaining open communication — especially when mistakes occur. Josh's approach encourages leaders to sit on the same side of the table with customers, foster trust early in the relationship, and create internal cultures where honesty and accountability thrive.

In this episode of The Customer Wins, Richard Walker interviews Josh DeTar, EVP of Evangelism at Tyfone, about elevating digital experiences for community financial institutions. Josh discusses the power of transparency, the role of culture in customer success, and why "breaking bread" — literally — helps strengthen relationships. He also explores long sales cycles, building features that matter, and leading with humility.

Brian Portnoy is the Founder of Shaping Wealth, a company that delivers human-first, applied behavioral-finance learning and engagement for financial advisors, corporations, and educational institutions. A CFA charterholder with a PhD from the University of Chicago, Brian has over two decades of experience in hedge-fund and mutual-fund investing. He now focuses on helping people make better money decisions and align finance with a meaningful life. Brian is also the best-selling author of The Geometry of Wealth and The Investor's Paradox.

Financial advisors excel at technical guidance but struggle with the deeper human challenges their clients face. Money triggers stress, fear, and uncertainty, yet most advisors aren't trained to navigate those emotional dynamics. How can advisors improve their conversations, build trust, and truly guide clients toward better financial decisions?

Brian Portnoy, an expert in behavioral finance and the psychology of money, explains how advisors can strengthen their emotional intelligence, clarify their own money stories, and adopt a human-first mindset. Highlighting the value of skills such as self-awareness, empathy, and better listening, Brian emphasizes practical tools for improving client conversations across prospecting, discovery, onboarding, and reviews. He also shares the importance of well-being science and how understanding happiness and purpose can meaningfully reshape financial guidance.

In this episode of The Customer Wins, Richard Walker interviews Brian Portnoy, Founder of Shaping Wealth, about human-centered financial advice. Brian discusses the psychology of money, improving client conversations, and the role of emotional intelligence. He also explores advisor wellbeing, communication strategies, and the impact of AI-powered coaching tools.