Dakota Rainmaker Podcast

In this episode of the Rainmaker Podcast, host Gui Costin, founder and CEO of Dakota, sits down with John Bailey, co-founder of OneFund Investments, to discuss how his firm is democratizing access to venture capital and private equity. Bailey shares insights into his journey from working at General Atlantic to launching OneFund and the strategies that have contributed to the firm’s growth.Bailey begins by reflecting on his background, from studying at Tufts University to earning an MBA from Wharton. After working in consulting and growth equity, he realized a fundamental issue in the investment industry: access to top-tier private equity and venture capital funds was restricted to institutional investors and ultra-high-net-worth individuals. With minimum check sizes in the millions, most investors were effectively shut out of these opportunities. Seeing this gap, Bailey co-founded OneFund Investments, a fund of funds designed to provide accredited investors with diversified access to top-performing funds in the private markets.Launching OneFund required a strategic approach to building investor relationships from the ground up. Unlike established firms with large institutional networks, OneFund had to develop a go-to-market strategy tailored to a new investor demographic. One key lesson Bailey shares is the importance of listening to potential investors before designing a product. Many firms build their funds first and then try to sell them, but OneFund engaged with investors early to understand their needs, shaping its offerings to provide the access and diversification they were looking for.Bailey also highlights the crucial role of technology in managing investor relationships. A well-implemented CRM system allows the team to track investor engagement, refine outreach efforts, and tailor communications based on behavior patterns. Rather than relying on broad content distribution, OneFund takes a personalized, high-touch approach, ensuring investors receive relevant and timely information. Education has been a major focus, as many of their investors are new to private equity. To address this, OneFund offers webinars, investor calls, and detailed materials to help clients make informed decisions.Reflecting on leadership, Bailey believes in leading by example and embracing every aspect of the startup process, from high-level strategy to granular tasks. His advice to young professionals is to align themselves with a product they truly believe in, as conviction is key to long-term success. This conversation offers valuable insights for sales professionals, fundraisers, and investors looking to navigate the evolving private equity landscape.

In this episode of The Rainmaker Podcast, host Gui Costin sits down with Brad Jung, Head of North America Advisor and Intermediary Solutions at Russell Investments. Jung shares insights on sales leadership, team alignment, and how to effectively manage a large, remote sales force while maintaining high performance.Jung opens with his personal story, reflecting on his early work experiences, from a childhood paper route to working construction in college. These formative experiences instilled in him the value of hard work, relationships, and the importance of service—principles that have shaped his leadership style today.As the conversation shifts to Russell Investments, Jung discusses the firm’s evolution from institutional investment management to serving individual investors. He explains how the company's institutional sales approach trickled down into financial advisory services, allowing individual investors to benefit from the same level of sophistication as large institutions. With over $331 billion in assets under management as of 12/31/24, Russell Investments is a global leader in investment management solutions.A key focus of the episode is managing a remote sales force effectively. With 70% of his 120-person North American team working remotely, Jung emphasizes the importance of alignment, communication, and transparency. He structures his leadership approach around five pillars: strategy, structure, people, process, and performance. Weekly pipeline meetings ensure sales teams remain accountable, while leadership focuses on removing roadblocks to success. He also highlights the importance of tracking and reporting sales activity to prevent misalignment between internal and external sales teams.Jung introduces a "collision" communication method, where informal, unplanned conversations replace rigid, scheduled meetings. He actively reaches out to team members for short check-ins, believing these real-time interactions provide deeper insights into challenges and opportunities. He also discusses the necessity of a robust CRM system, ensuring all sales activities are logged, analyzed, and leveraged for smarter decision-making.As the discussion unfolds, Jung emphasizes the role of mentorship and continuous learning. He urges young professionals to find mentors, stay curious, and master their craft. He also shares leadership lessons from his own journey, emphasizing the importance of knowing your “why”, inspiring a shared vision, and leading with a personal, relationship-driven approach.The episode wraps with a discussion on prioritization and adaptability in leadership. Jung stresses the importance of focusing on what truly matters, staying agile in the face of industry changes, and fostering an environment where salespeople feel supported, valued, and motivated to perform at their best.

In a fascinating discussion, Jonathan Harari, Managing Director at Crescent Capital Group, shares his journey from Paris to finance leadership, including stints at PIMCO and Blackstone. He emphasizes a true sales mindset, advocating for proactive outreach and building relationships with 'new names' in client engagement. Harari also dives into team dynamics, stressing the importance of CRM systems, transparency, and a supportive culture in fostering sales success. His insights offer valuable lessons for anyone looking to innovate in the field of sales leadership.

In this episode of The Rainmaker Podcast, host Gui Costin, Founder and CEO of Dakota, sits down with Allen Gray, Managing Director at Silvercrest Asset Management Group. With decades of experience in institutional sales and marketing, Allen shares insights into his career, leadership philosophy, and the evolving landscape of institutional investing.Allen begins by discussing his career journey, which started at Kidder, Peabody & Company despite having no formal business education. He quickly adapted, completing accounting courses and participating in a management training program. After the firm's acquisition by General Electric, he sought partnership opportunities and co-founded Radnor Capital Management, growing assets from $10 million to $1.6 billion in six years before selling to U.S. Trust Company. Later, at Osprey Partners, he helped expand assets from $800 million to $4.2 billion in just two and a half years.At Silvercrest, Allen was tasked with building an institutional business from the ground up. When he joined in 2008, the firm had $6.5 billion in ultra-high-net-worth assets but only $100 million in institutional assets. Through strategic acquisitions and disciplined growth, Silvercrest now manages $10 billion in institutional assets, with top clients averaging over $400 million each. The firm has expanded investment capabilities, adding growth and international strategies.Allen’s sales strategy emphasizes process over volume. His teams are structured into small, specialized silos with dedicated investment, client service, and business development professionals. He stresses relationship-building over transactional sales, ensuring long-term partnerships. Silvercrest also leverages subadvisory relationships, allowing distribution through larger platforms without engaging in retail sales.Communication and transparency are essential to Allen’s leadership. Silvercrest tracks an "actionable pipeline", focusing on opportunities likely to close within six months. His trust-based leadership allows experienced professionals the freedom to execute their responsibilities while maintaining accountability. He prioritizes hiring skilled individuals, providing them with the right tools, and minimizing bureaucracy.For young professionals entering the fundraising business, Allen advises deep investment knowledge beyond sales materials. Understanding market dynamics, analyzing performance data, and maintaining transparency in tough times are key to success. He highlights industry challenges, including increased competition from consulting firms offering multi-manager funds, making direct institutional outreach more crucial.

In this episode of The Rainmaker Podcast, Gui Costin sits down with Todd Cassler, Chief Growth Officer and Partner at Cerity Partners, to explore the strategies and mindset that have fueled Todd’s success in financial services. With over 25 years of industry experience spanning roles at Mariner Wealth Advisors, John Hancock Investments, and Manulife Investment Management, Todd shares his journey from an unexpected start in insurance to leading growth initiatives at a firm managing $130 billion in assets.Todd discusses the nuances between institutional, wealth management, and retail channels, highlighting the key differences in decision-making processes. While institutional markets rely on professional buyers and defined frameworks, the wealth management space offers more flexibility to influence decisions at the point of sale. Todd emphasizes the importance of focusing on channels where firms have the highest probability of success, rather than chasing large mandates with low chances of conversion.The conversation delves into leadership and growth strategies. Todd stresses starting with clear goals, the “big rocks”, and having an honest reflection on an organization’s capabilities. He advocates for focusing on high-impact areas rather than spreading resources too thin. On leadership, Todd champions empowerment, accountability, and adaptability. He believes in hiring talent for the future, fostering transparent communication, and delivering both positive feedback and constructive criticism to drive growth.Todd also touches on the critical role of technology, particularly CRM systems, in enhancing productivity, managing risk, and supporting data-driven decisions. For small teams skeptical of CRM adoption, he underscores its value not just as a sales tool but as an essential part of client retention and business continuity.Wrapping up, Todd offers advice to young professionals: show up, listen more than you speak, ask insightful questions to establish expertise, and invest in personal development. His insights provide actionable takeaways for fundraisers, sales leaders, and anyone looking to excel in financial services.

In this episode of the Rainmaker Podcast, Gui Costin interviews Eric Green, Chief Investment Officer at Penn Capital, about the firm’s innovative approach to small-cap investing and current market opportunities. With over 25 years of experience, Eric shares how Penn Capital employs its Complete Capital Structure Analysis™, a methodology that examines a company’s entire capital structure, from secured debt to equity, to uncover hidden value and mitigate risk. This integrated perspective allows Penn Capital to spot market inefficiencies and make better-informed investment decisions, distinguishing them from traditional small-cap managers. Eric explains how Penn Capital focuses on leveraged small-cap companies, which many managers avoid, as they historically outperform over the long term. By leveraging credit expertise, Penn Capital ensures these investments are carefully selected to minimize risk, boasting an impressive track record of avoiding bankruptcies in their equity portfolios. He also stresses the importance of partnering with true small-cap managers who align with the Russell 2000, warning that many managers operate with inflated market caps that fail to deliver the expected diversification and growth potential of small-caps. Eric highlights macroeconomic factors positioning small-caps for a rebound, including deregulation, M&A activity, and anticipated interest rate cuts. He identifies sectors like natural gas, which is critical in the energy transition, and consumer industries such as gaming and restaurants, which benefit from strong spending trends, as key areas of opportunity. The episode concludes with Eric’s advice on diversification within small-cap investing. Penn Capital’s alpha-generating strategies thrive during upcycles, making them a valuable complement to more defensive small-cap managers. This episode offers actionable insights into navigating the small-cap space, helping investors capitalize on emerging opportunities in today’s market. 

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. 

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.

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.

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.