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.

Diana Cabrices is the Founder and Fractional Chief Evangelist of Diana Cabrices Consulting, a growth-focused firm that energizes B2B wealthtech and financial services brands by amplifying their stories and building emotional connection with financial advisors. She has a track record of driving significant revenue growth, having helped a martech platform grow its recurring revenue by 10x in three years. Diana partners with CEOs and leadership teams to serve as their outsourced brand evangelist, speaker, and growth ambassador. A frequent industry speaker and contributor, she leverages her experience across sales, marketing, technology, and advisor engagement to help companies scale.

Many fintech and advisory firms struggle to stand out, explain their value, and consistently get in front of the right audiences. Marketing feels fragmented, sales conversations start too zoomed in on product features, and social content falls flat. How can these firms turn their story into an engine for demand and trust?

Diana Cabrices, a brand evangelist specializing in fintech and financial services, recommends starting with deep listening — reviewing sales and customer calls to uncover real pain points and language that resonates. She then builds messaging around the problem, not the product, and amplifies it through stages, webinars, podcasts, video, and especially LinkedIn to meet advisors where they are. Diana stresses partnering with leadership while confidently challenging assumptions, using social content that feels human and bold, and leaning on AI only as a "second brain" to repurpose content, not to replace authentic, on-stage performance.

In this episode of The Customer Wins, Richard Walker interviews Diana Cabrices, Founder and Fractional Chief Evangelist of Diana Cabrices Consulting, about using brand evangelism to drive growth. Diana also talks about crafting customer-led messaging, leveraging LinkedIn, and using AI tools without losing authenticity.

Ben Wiener is the Managing Partner at Jumpspeed Ventures, a venture-capital firm focusing on early-stage, Jerusalem-founded tech startups. Since founding the firm in 2014, he has served as the lead investor in dozens of startups and often provided their very first capital. Before his VC work, Ben co-founded his first startup in 1999 and gained experience as both a corporate lawyer and clerk at Israel's Supreme Court. He is also the author of Fever Pitch and holds a BA in economics from Yeshiva University and a JD with honours from Columbia Law School.

Communicating the true value of an idea is a common hurdle for entrepreneurs — investor interest often fades not from weak concepts but from unclear or uninspired pitches. Even the most innovative founders can stumble when translating passion into persuasion. How can startups tell their story in a way that connects deeply with investors and customers alike?

Venture capitalist and author Ben Wiener shares how storytelling can transform the way founders present their businesses. Drawing from his experience and his book Fever Pitch, he introduces the HEART framework — a five-part structure that helps entrepreneurs communicate their purpose, stakes, alternatives, differentiation, and team strengths. He emphasizes truth over performance, encouraging founders to make their product — not themselves — the hero of the story. By focusing on clarity, authenticity, and emotional connection, Ben's approach helps entrepreneurs pitch with confidence and integrity.

In this episode of The Customer Wins, Richard Walker interviews Ben Wiener, Managing Partner at Jumpspeed Ventures, about the art of storytelling for entrepreneurs. Ben discusses his HEART framework for crafting compelling startup pitches, why truthfulness matters more than flash, and how to shift the focus from the founder to the product. He also shares insights on the role of AI in storytelling and lessons from his own entrepreneurial journey.

Thomas Clawson is the Co-founder of Slant, a next-generation AI-powered CRM built to help financial advisors streamline workflows and deepen client relationships. He co-launched the platform to replace traditional CRM systems by integrating AI agents that manage meetings, follow-ups, and client interactions. Under his leadership, Slant has raised $3.3 million in seed funding and scaled to serve over a thousand advisors. Prior to this venture, Thomas held leadership roles in marketing and demand generation at tech unicorns, including Whatnot and Podium.

Financial advisors face growing pressure to deliver personalized service while managing an ever-expanding workload. Traditional CRMs, however, often add complexity instead of reducing it — creating more manual tasks and slowing growth. With AI transforming the way professionals work, how can financial advisors adopt technology that actually simplifies their day-to-day operations while improving client outcomes?

Thomas Clawson, an expert in advisor technology and automation, shares how embracing AI-first design principles can completely redefine the CRM experience. He emphasizes simplifying workflows, reducing manual data entry, and allowing advisors to focus on people instead of processes. Thomas discusses how chat-based interfaces and AI-powered insights can make managing client relationships seamless. By building adaptable systems that learn from user behavior, Thomas highlights how advisors can serve more clients efficiently while maintaining a personal touch.

In this episode of The Customer Wins, Richard Walker interviews Thomas Clawson, Co-founder of Slant, about reimagining CRM for financial advisors through AI and automation. Thomas also discusses the need for simplicity in advisor technology, the rise of chat-driven user interfaces, and how his team built a secure CRM in just six months.

Michelle Feinstein is the General Manager and Vice President, Global Financial Services at Salesforce, a company that provides cloud-based CRM and enterprise software to help businesses connect with customers. She leads global solutions and strategy for the financial services sector, focusing on wealth and asset management. With over 25 years of experience in the industry, Michelle guides firms in digital transformation, data usage, and advisor-client engagement. She works across product, partner, and client teams to modernize the technology and operations of financial firms.

Financial services firms face challenges in unifying technology, streamlining advisor workflows, and adopting AI to improve experiences. Legacy systems, fragmented data, and slow governance often block innovation. How can firms modernize, improve adoption, and leverage AI while maintaining trust?

Michelle Feinstein, an expert in digital transformation and client experience, explains that success begins with a clear strategic purpose — identifying the specific business outcomes technology should achieve. She shares how leading firms streamline advisor experiences by integrating data, simplifying workflows, and leveraging AI to automate repetitive tasks such as meeting prep and client summaries. Michelle also emphasizes adopting open, flexible systems that allow firms to plug in specialized AI tools while keeping human oversight central to innovation.

In this episode of The Customer Wins, Richard Walker interviews Michelle Feinstein, General Manager and VP of Global Financial Services at Salesforce, about transforming financial services with AI and customer-centric design. Michelle discusses how firms can build unified experiences, leverage AI agents for automation, and transition to consumption-based pricing models that drive efficiency. She also shares insights on advisor retention, data integration, and the future of AI adoption.

Greg Bennick is the Founder and Executive Director of One Hundred For Haiti, an international humanitarian initiative focused on rural Haiti's development, community leadership, and human empowerment. He is also a keynote speaker, documentary producer, and author of Reclaim The Moment. Greg has delivered transformative presentations in 27 countries, spoken to audiences ranging from private groups to thousands at major corporate events, and has been recognized as a TEDx speaker. His work centers on building better teams, fostering authentic human interactions, and helping organizations and individuals reclaim focus amidst daily distractions.

Many professionals struggle to connect authentically with their audiences — whether in sales, leadership, or public speaking. They focus too much on outcomes like applause, recognition, or profit, and lose sight of the people they're meant to serve. How can leaders, speakers, and entrepreneurs shift their focus from themselves to creating genuine, lasting impact for others?

Greg Bennick, keynote speaker, author, and humanitarian, offers actionable insights on how to engage people through authenticity, empathy, and listening. He explains that effective communication starts before the first word is spoken — by observing, preparing with intention, and reading the room. Greg encourages listeners to check their egos, focus on shared human experience, and remain adaptable in every interaction. Drawing on decades of stage experience, he emphasizes that success comes from service, not self-promotion.

In this episode of The Customer Wins, Richard Walker interviews Greg Bennick, keynote speaker and author at gregbennick.com, about the power of authenticity in communication and leadership. Greg shares how to listen deeply to audiences, build trust through vulnerability, and adapt quickly when plans change. He also discusses public speaking fears, the role of AI in creativity, and lessons from his book Reclaim the Moment.