

Dakota Rainmaker Podcast
Dakota Team
The "Dakota Rainmaker Podcast," hosted by Gui Costin, CEO of Dakota, offers a unique look into sales strategies from top industry executives. Each episode explores the inner workings of successful sales organizations, from philosophy to execution. This podcast is essential for sales professionals seeking wisdom from the best in the field.
Episodes
Mentioned books

Jan 28, 2025 • 47min
Leadership, Longevity, and the Future of Asset Management with Brian Maute of DWS
In this Rainmaker Podcast episode, Gui Costin, Founder and CEO of Dakota, interviews Brian Maute, Head of U.S. Wholesale at DWS. Brian shares his career journey, leadership philosophy, and insights into sales, leadership, and talent development in the asset management industry. Brian discusses his transition from wealth management to asset management, advancing through roles at Van Kampen Investments and DWS. He highlights the importance of longevity in career success, emphasizing how institutional knowledge and trusted relationships have helped him navigate challenges and achieve long-term impact. Brian outlines DWS’s team structure, which prioritizes collaboration, client-centric approaches, and specialization. He explains their segmentation strategy and commitment to continuous learning, regular communication, and accountability to ensure team success and adaptability to market changes. The conversation also explores the critical role of CRM systems, like Salesforce, in operational efficiency. Brian stresses the importance of accurate data entry, pipeline management, and task-setting to maximize client engagement and results. As a leader, Brian focuses on creating a vision aligned with client needs, fostering a collaborative and competitive culture, and maintaining accountability with kindness. For young sales professionals, he emphasizes curiosity, disciplined follow-up, and confidently asking for the order as keys to success. The episode concludes with Brian addressing industry challenges, including adapting to client needs and retaining top talent, while highlighting his commitment to building an exceptional work environment at DWS.

Dec 17, 2024 • 42min
Mastering Private Fundraising: Relationship Building, Market Shifts, and Sales Strategy with Nancy Vailakis
In this episode of the Rainmaker Podcast, Dan DiDomenico, President of Dakota, engages Nancy Vailakis, Principal of Ancram IRBD, in a dynamic discussion about trends, challenges, and strategies in the private funds industry. Nancy shares her wealth of experience, offering practical insights for fundraisers and sales professionals navigating today’s complex investment landscape.Nancy, a seasoned professional with over 18 years in alternative asset management, founded Ancram IRBD, a boutique placement agency and investor relations firm. Her expertise spans private equity, private credit, and real assets, focusing on niche strategies and first-time fund launches. With prior roles at IQ-EQ, Cerberus Capital, and BlueMountain Capital, and an MBA from NYU Stern, Nancy has built a reputation as a leader in fundraising and investor relations.The conversation highlights the evolving private funds market. Nancy emphasizes the increasing investor interest in defensive strategy sectors, such as industrials, business services, and healthcare. She notes challenges in liquidity, which have slowed allocations, but anticipates an improved fundraising environment in the coming year as interest rate decreases settle in and dealmaking continues to pick up.Nancy explains her sales process, focusing on relationship-building and understanding investor needs. She stresses the importance of aligning offerings with LP mandates, avoiding mismatches that can harm credibility. Nancy speaks about the flexibility her broker-dealer platform enables, to pivot between mandates based on market demand. Tools like CRMs and collaborative platforms enhance her efficiency, enabling her to track investor preferences, maintain strong relationships, and tailor pitches to meet specific needs.The discussion explores the value of meticulous preparation and professionalism in sales. Nancy advises young professionals to perfect their craft by mastering details, such as error-free communications and compelling pitch materials. She underscores that every interaction, whether an email or a call, can influence the success of a sale. Dan reinforces this, noting that while a first email might not close a deal, it can easily derail one.Nancy also shares her views on leadership. She attributes her success to a combination of data-driven decision-making, instinct, and deep industry knowledge. She highlights the importance of listening to LPs, understanding their unique constraints, and providing tailored solutions. Transparency and thoughtful communication, especially during challenging times, build trust and long-term partnerships.Looking ahead, Nancy remains optimistic. She sees opportunities in the evolving global fundraising landscape, particularly in regions like the Middle East and Asia. Despite the tough fundraising climate, she emphasizes the importance of resilience, specialization, and sticking to what you know best.This episode offers a masterclass in fund distribution and investor relations, providing practical takeaways for both seasoned professionals and newcomers to the industry. Nancy’s focus on thoughtful relationship management and adaptability shines as a guiding principle for navigating the complexities of alternative asset management.

Dec 10, 2024 • 1h 4min
Breaking Down Barriers: Jeff Carlin on Nuveen’s Shift to De-Channelized Sales Models
Welcome to another insightful episode of the Rainmaker Podcast hosted by Gui Kostin, Founder and CEO of Dakota. This week, Gui engages in a thought-provoking conversation with Jeff Carlin, CFA, Senior Managing Director and Head of Global Wealth Advisory at Nuveen. Jeff shares his extensive journey from his roots in San Francisco to becoming a pivotal figure in the investment industry, highlighting the milestones of his career, including his roles at Smith Barney, Charles Schwab, and IndexIQ before joining Nuveen in 2010.Jeff unpacks the evolution of Nuveen’s wealth distribution strategy and the shift towards prioritizing impactful advisor relationships. By leveraging lessons from the SaaS industry, Jeff and his team focus on efficiency, segmentation, and team-oriented structures to optimize advisor engagement. He emphasizes the importance of de-channelization, segmenting advisors by their operational style rather than labels, and aligning sales structures to address dynamic client needs.A key highlight of the episode is Jeff's analogy of sales teams as jazz ensembles—finding harmony by following a consistent core structure while allowing individual creativity. He delves into the significance of clear communication, leveraging CRMs for accountability, and fostering a culture of respect and collaboration within sales teams.Jeff also provides advice for aspiring professionals in sales, stressing the value of patience, continuous learning, and embracing mentorship—whether through direct interaction or by observing industry leaders. He touches on the challenges of attracting and retaining top talent, emphasizing the necessity of aligning individual motivations with organizational culture.The episode concludes with Jeff's vision for sustainable success: building teams that are not just results-driven but also operate cohesively and ethically. Gui wraps up by reflecting on the core principles shared and their applicability to building thriving distribution organizations.

Dec 3, 2024 • 34min
The Power of a Consultative Sales Approach with Rob Logan of Principal Asset Management
In this episode of the Rainmaker Podcast, host Dan DiDomenico sits down with Rob Logan, Managing Director and Head of Distribution for Retirement Investments at Principal Asset Management. Rob brings nearly 30 years of experience to the discussion, sharing actionable insights on sales leadership, team culture, and navigating a rapidly evolving marketplace.Rob provides a detailed overview of Principal’s operations, including its position as a Fortune 500 financial services company and its growth in global asset management, now managing $513 billion in assets. He outlines his team's structure, which focuses on three key sales channels: DCIO, high-net-worth RIAs, and retirement investment support. Rob highlights how his team leverages business intelligence, CRM tools like Salesforce, and a consultative sales approach to drive results in a competitive landscape.The conversation dives into Rob’s leadership philosophy, emphasizing servant leadership, transparent communication, and respect as critical to building a successful and cohesive team. He also offers advice for aspiring sales professionals, encouraging them to become students of the industry, develop a consistent sales process, and maintain a healthy work-life balance.Rob and Dan explore current market trends, including the rise of alternative investment vehicles, market consolidation, and the convergence of retirement and wealth management. Rob’s forward-thinking approach and dedication to his team provide valuable lessons for leaders and sales professionals alike.This episode is packed with insights on driving growth, fostering collaboration, and staying ahead in a dynamic industry. Don’t miss the opportunity to learn from Rob’s wealth of experience.

Nov 26, 2024 • 43min
Revolutionizing Sports: Wayne Kimmel of SeventySix Capital on Innovation, Tech, and the Future of Fan Engagement
In this captivating episode of the Rainmaker Podcast, host Gui Costin engages with Wayne Kimmel, CEO and founder of SeventySix Capital, a venture capital company revolutionizing the sports industry. With a career spanning investments in tech, sports media, and entertainment, Kimmel shares insights into his company’s mission to back entrepreneurs who are redefining the sports landscape using innovative technologies like AI, data analytics, and augmented reality.Kimmel recounts how SeventySix Capital started in 1999, focusing on groundbreaking ventures like SeamlessWeb, Take Care Health Systems, and NutriSystem, before transitioning to the sports industry in 2018. Today, the firm is laser-focused on investing in technologies that enhance both on-field performance and the fan experience. From AI-driven data solutions to smart bats developed by portfolio companies like Diamond Kinetics, Kimmel illustrates how technology is democratizing access to professional-grade tools, making them available to athletes at all levels.A recurring theme in the discussion is the intersection of sports and innovation. Kimmel highlights notable investments, such as C360, which developed the pylon cam technology widely used in NFL broadcasts by all the major media networks. He explains how these technologies create immersive experiences for fans and unlock new revenue streams for sports organizations. Kimmel also delves into SeventySix Capital’s strategic use of thought leadership and media, including the SeventySix Capital Sports Leadership Show, to attract top-tier entrepreneurs and maintain its industry edge.The conversation touches on broader trends shaping the sports ecosystem, including the integration of AI and data analytics, the rise of sports betting, and the expanding role of major tech players like Amazon and Apple in sports broadcasting. Kimmel also underscores the critical importance of integrity and compliance in regulated industries like sports betting, emphasizing SeventySix Capital’s commitment to creating safe, fun, and sustainable business models.Closing the episode, Kimmel reflects on the immense opportunities within the $3 trillion sports industry, from fan engagement to advanced tech adoption. He credits SeventySix Capital’s success to its ability to source groundbreaking ideas, build meaningful relationships, and push the boundaries of innovation. This insightful episode is a must-listen for anyone interested in the future of sports, technology, and investment.

Nov 21, 2024 • 39min
Rainmaker Live! November 2024
In this episode of Rainmaker Live!, Gui Costin, Founder and CEO of Dakota, and Tim Dolan break down the Four Core Principles of the Dakota Sales System, offering a step-by-step guide to achieving sales success in the investment management industry. They discuss the launch of Dakota Talent, a specialized job board connecting talent and employers, and introduce the Rainmaker Podcast, a platform where industry leaders share their strategies. Gui and Tim dive into key topics, including setting clear sales expectations, identifying high-impact target markets, mastering sales meetings, and building a robust follow-up system using CRM tools. Packed with actionable insights and real-world examples, this episode is a must-listen for investment professionals looking to refine their sales approach, improve accountability, and drive meaningful results. Tune in for practical advice and a roadmap to sales excellence!

Nov 12, 2024 • 41min
The Power of Cold Outreach in Private Markets with Valentine Whittaker of Epic Funds
In this Rainmaker Podcast episode, Gui Costin, Dakota’s Founder and CEO, interviews Valentine Whittaker, Director at Epic Funds. With over 20 years of private market experience, Valentine shares his career journey, his role at Epic Funds, and insights into his leadership approach, particularly in sales and investor relations. Valentine has a deep background with firms like Abbott Capital Management, Schroders Capital, and JP Morgan, bringing a unique perspective to managing investor relationships and business development in the private fund space.Valentine explains that Epic Funds prioritizes providing niche, capacity-constrained strategies, viewing investor relations as a crucial, solution-driven role. His team leverages a process-driven approach to sales, using tools like Dakota’s technology to maximize efficiency and target client engagements. Valentine highlights the importance of advance planning, building a forward calendar that outlines key meetings and opportunities in each city, ensuring a streamlined and purpose-driven travel schedule.Cold outreach is a cornerstone of Valentine’s strategy, emphasizing the value of personal touchpoints, whether through phone calls or follow-up emails. He discusses how tools like LinkedIn and Dakota help track industry shifts, such as when professionals change roles, turning these moments into genuine engagement opportunities. Valentine advocates for using CRMs to maintain organized records of client interactions, making follow-ups and deal progress easy to manage. The consistent and process-oriented approach, he notes, is critical to staying efficient and focused, especially for smaller teams.In a segment on leadership, Valentine describes his style as collaborative and supportive, emphasizing teamwork and empowering colleagues. For those new to investment sales, he stresses the importance of mentorship, product knowledge, and diligent preparation. To him, successful investment sales require not just mastering pitches but also understanding the nuances of investment products and building authentic relationships with clients.Valentine also highlights the challenges in educating clients about private market funds, particularly trustees unfamiliar with the space. He sees this as an ongoing effort, where educating allocators helps cultivate meaningful partnerships, positioning Epic Funds as a reliable resource. His passion for sales and client education comes through as he reflects on the privilege of serving clients in the private markets.This episode is packed with actionable insights on sales strategy, client engagement, and leadership, making it a must-listen for anyone in the investment sales arena.

Nov 5, 2024 • 47min
Client-Centric Leadership at Vanguard with Jane Greenfield
In this episode of The Rainmaker Podcast, host Gui Costin interviews Jane Greenfield, the head of consultant engagement at Vanguard, a leader in investment and wealth management with over $9 trillion in assets. Jane shares insights into her career journey from banking to her current role, emphasizing Vanguard's unique client-centered culture. With a mission-driven focus, Jane highlights how Vanguard’s client-owned structure, established by founder Jack Bogle, creates a strong emphasis on long-term client relationships, which she has been a part of for over 23 years.A major theme of their discussion is the value of institutional knowledge gained through longevity within a company. Jane explains how Vanguard’s rotational culture allowed her to develop a comprehensive understanding of the firm, which she believes is vital to serving clients effectively. Gui and Jane also discuss the importance of company culture in fostering success, with Jane sharing that Vanguard prioritizes team collaboration, support, and a commitment to the client’s best interests. This dedication to the client is reflected in their approach to sales, where the team treats consultant relationships with the same care they would with clients.The conversation dives into Vanguard’s sales process, with Jane outlining the team’s strategic approach to building relationships and their tactical focus on client engagement, preparation, and follow-up. Weekly and monthly team huddles, along with town halls and dashboards, keep everyone aligned and foster transparency. She also discusses Vanguard’s commitment to using CRM systems to capture critical client interactions, reinforcing the importance of clear, structured communication within the team and with leadership.Jane’s leadership style is grounded in being “in the arena” with her team, supporting a long-term approach and balancing high expectations with compassion. She concludes by offering advice to aspiring professionals: be relentless learners about clients, offerings, and the sales craft itself. For Jane, an effective leader is one who is accessible, focused, and committed to the growth and success of both the team and its clients, embodying a culture where teamwork and client focus lead to sustained success.

Oct 29, 2024 • 38min
Strategic Leadership and Wealth Management: Frank Riccio of First Eagle Investments
In this episode of the Rainmaker Podcast, host Dan DiDomenico, President of Dakota, sits down with Frank Riccio, Head of U.S. Wealth Solutions Sales and Strategic Relationships at First Eagle Investments. Frank brings over 20 years of leadership experience in the financial industry, having previously held prominent roles at PIMCO and Allianz Global Investors. In this conversation, he delves into his background, career journey, and current role at First Eagle, where he oversees daily operations and drives strategic initiatives for the Wealth Solutions team.Frank gives listeners an insightful overview of First Eagle Investments, a privately held asset management firm managing $140 billion in assets. He highlights the firm's commitment to active management and its rich history dating back to 1864. First Eagle’s investment approach emphasizes resilient wealth creation, a philosophy that has proven its value across market cycles, particularly during periods of market volatility.A significant portion of the conversation centers around the importance of sales leadership and team management. Frank explains how First Eagle’s sales team is organized to maximize efficiency, including a dedicated focus on major metropolitan areas, and how the firm leverages data to optimize sales efforts. He shares insights on his leadership style, emphasizing transparency, direct communication, and the value of cultivating a strong company culture. Frank also talks about the importance of feedback loops within his team, discussing how regular communication and collaboration ensure alignment with the firm’s goals.For those early in their career, Frank offers advice, encouraging young professionals to take full advantage of the opportunities in entry-level sales roles, such as gaining exposure to different areas within an asset management firm. He stresses the importance of controlling what you can control and staying positive, even when faced with rejection.The episode concludes with a discussion of the challenges and priorities facing First Eagle in the future, particularly in terms of balancing internal responsibilities, client engagement, and maintaining a focus on long-term growth through strategic hiring and team development. This episode provides valuable insights into the leadership strategies of a seasoned industry veteran and offers practical advice for those looking to succeed in the financial services sector.

Oct 8, 2024 • 38min
Mastering Boutique Growth: Mark Clewett on Leading Conestoga Capital Advisors to $8 Billion in Assets
In this episode of the Rainmaker Podcast, guest Mark Clewett, President and Managing Partner of Conestoga Capital Advisors, sits down with host Dan DiDomenico to discuss his career, leadership philosophy, and the growth of his firm. Clewett shares his professional journey, beginning with his education in finance at Penn State and early roles at SEI Investments and Delaware Investments. He reflects on joining Conestoga in 2006 when the firm was relatively small, managing $200 million in assets with a team of just seven people. Over the years, Conestoga grew into an established boutique firm with over $8 billion in assets under management.Clewett credits much of Conestoga's success to its focus on small- and mid-cap growth equity strategies and its emphasis on long-term, durable relationships. He emphasizes the importance of consistency and quality in client communications, especially when engaging institutional consultants. Clewett also highlights the firm’s niche strategy of concentrating on portfolios of companies with a competitive advantage and sustainable earnings growth, which has positioned Conestoga well within the competitive investment landscape.The conversation touches on the key role consultants have played in Conestoga’s growth. Initially, Clewett focused on institutional relationships to leverage consultant networks, which helped expand the firm’s reach. Over time, the sales team grew to include dedicated personnel for institutional and advisor relations. Clewett also discusses the importance of a strong internal culture, where all teams—whether investment, client service, or operations—work closely and respect each other’s roles.Clewett offers practical advice for young professionals and sales leaders, emphasizing the long-term nature of relationship-building and the need to embrace change in career trajectories. He reflects on his personal leadership style, noting that maintaining the firm’s collaborative, respectful culture is a priority as Conestoga grows.The episode concludes with a discussion about scaling a boutique firm, the challenges of competing with industry giants, and the constant need to elevate marketing materials and communications as the firm expands. Clewett's insights provide a thoughtful roadmap for navigating the complexities of growing and leading a boutique investment firm.