

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

Jun 3, 2025 • 23min
Fundraising with Precision: Inside Optimizing Sales at LAB Quantitative Strategies with Shane McCarthy
In this episode of the Rainmaker Podcast, host Gui Costin welcomes Shane McCarthy, Managing Director at LAB Quantitative Strategies, for a thoughtful and practical conversation on building a lean, high-performing fundraising function in a data-driven investment firm. With over 25 years in the investment industry across operations, risk, product development, and portfolio management, Shane brings a rare full-stack view of capital formation.Shane shares how LAB QS, a $1.8 billion multi-strategy hedge equity manager based in Denver, is built around a risk-first, liquid, and return-per-unit-of-risk mindset. Originally spun out from one of the largest family offices in the U.S., LAB QS retains a strong cultural alignment with high-net-worth and family office investors, with growing interest from RIAs and small institutions. Their hedged equity strategy is structured to smooth volatility, limit drawdowns, and complement broader asset allocations.The business development team is lean—just two people—but Shane emphasizes that LAB QS operates with a firmwide fundraising mentality, supported by every department, from operations to compliance. The sales strategy is guided from the executive committee level, with clear goals and aligned resource allocation. Everyone has defined roles, responsibilities, and expectations, which ensures a unified commercial mindset across the firm.McCarthy stresses that face-to-face interaction and trust-building are still paramount in capital raising, especially in today's saturated and competitive investment landscape. While Zoom helps with efficiency, nothing replaces the relationship-building power of sitting across from an investor.LAB QS’s tech-forward approach is another key strength. They rely heavily on Salesforce for CRM, integrated with Dakota Marketplace for seamless prospecting and pipeline management. With support from a 10-person tech team, LAB QS uses proprietary tools to customize analytics and automate reporting, enabling more effective and informed client interactions.Culturally, LAB QS embraces a challenge process, encouraging employees at all levels to contribute ideas and question assumptions. This openness fosters humility, collaboration, and innovation—qualities that Shane believes are essential for long-term success.To young professionals, Shane offers grounded advice: embrace the long game, expect rejection, and focus on knowing your client deeply. His leadership and experience reinforce a message that great sales organizations are built on cross-functional collaboration, disciplined execution, and the humility to keep learning.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

May 27, 2025 • 32min
Capital Formation, Not Sales – Inside CAZ with Christopher Zook
In this episode of the Rainmaker Podcast, host Gui Costin sits down with Christopher Zook, founder and chairman of CAZ Investments, for an in-depth conversation on building a capital formation powerhouse rooted in intentional language, disciplined processes, and unwavering alignment. With over 30 years of investing experience, Zook shares his journey from brokerage beginnings at PaineWebber and Lehman Brothers to launching CAZ Investments—driven by a goal he set in 1991 to start his own firm within a decade, a promise he fulfilled nearly to the day.At CAZ, everything begins with personal capital. The firm identifies thematic opportunities, invests their own capital, and invites others to join alongside them—creating a culture of alignment captured in their mantra, “lead with alignment.” CAZ now manages over $9 billion in assets, up from $350 million in 2013, through 100% organic growth.A major theme of the episode is language and positioning. Zook emphasizes the importance of words in shaping perception. His team doesn’t “pitch” or share “decks”—they educate, advise, and present thoughtfully crafted materials. Their business development team is known as “Capital Formation,” reflecting the consultative, relationship-based approach they bring to investors.Zook shares how he built a capital formation team modeled on his own early sales experience, hiring in waves and fostering peer cohorts to build camaraderie and consistency. Their process includes detailed metrics—outreach volume, presentation count, conversion rates, and line depth with investors. Zook stresses the value of cultivating multiple lines with clients, which statistically improves retention and referrals.The team operates under a three-pillar framework: find new investors, deepen relationships with existing ones, and turn clients into raving fans. Zook underscores the power of consistent communication, proactive outreach during market volatility, and delivering standout service when most others retreat.CAZ has long embraced CRM, becoming an early adopter of Salesforce in 2005. Zook believes that the right CRM setup—customized for usability and leveraged for reporting—can drive a competitive, transparent, and merit-based sales culture. Dashboards, stack rankings, and responsiveness metrics keep the team focused and accountable.Zook also shares the story of co-authoring The Holy Grail of Investing with Tony Robbins and closes with timeless advice: success is built on hard work and attention to detail. For young professionals and leaders alike, this episode is a masterclass in building a high-integrity, high-performing investment firm from the ground up. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

May 20, 2025 • 47min
How Stacy Havener Built Havener Capital on Storytelling and Strategy
In this episode of the Rainmaker Podcast, Gui Costin is joined by Stacy Havener, founder and CEO of Havener Capital Partners, for a masterclass on raising capital through storytelling, behavioral finance, and human connection. Stacy’s path into the investment industry defies convention. With a background in English literature—not finance—and no Wall Street pedigree, she’s raised over $8 billion for emerging managers, resulting in more than $30 billion in follow-on assets under management. Her secret? A repeatable, story-led, data-backed approach that meets investors where they are.Stacy shares how behavioral science and human psychology inform every layer of her process. Her philosophy is simple but powerful: “Investors don’t make decisions with spreadsheets alone.” Instead of the traditional pitch-first, data-heavy approach, she advocates for flipping the script—connecting emotionally first, then backing it up with data. From how a PM smiles in a meeting to the power of a well-timed question, she details the overlooked human cues that build trust and open doors.One of the standout moments of the episode is Stacy’s take on pitch decks: ditch them, at least in the first meeting. Research shows prospects feel more positively about meetings when they do 70% of the talking. That kind of engagement doesn’t happen when fund managers are reading slides. Instead, she encourages sales professionals to focus on making meetings conversational, choreographing the interaction like a late-night talk show host—her version of the “Jimmy Fallon strategy.”Stacy dives deep into meeting preparation, suggesting salespeople treat every meeting like a performance: prepare with a one-page brief, run a 15-minute pre-meeting with the PM, and walk into the room ready to humanize the conversation. She emphasizes that salespeople are not “carrying bags”—they are critical orchestrators of connection, learning to read the room, ask better questions, and track not just activity, but allocator behavior.Closing the episode, Stacy offers clear advice to young professionals: perfect the craft before scaling the activity. Learn how to sell with purpose and intention, and let repetition come only after mastery.This episode is a blueprint for any sales professional, allocator, or fund manager looking to break the mold and raise capital through authenticity, insight, and human connection.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraisingprocess with accurate, up-to-date investor data.

May 13, 2025 • 37min
Joe Grogan on Culture and Consultative Sales at WisdomTree
In this episode of the Rainmaker Podcast, host Gui Costin sits down with Joe Grogan, Head of Distribution for the Americas at WisdomTree, for an energizing conversation on leadership, sales strategy, culture, and the power of treating people like owners. With over 25 years of experience at firms like Fidelity and State Street, Joe shares how his humble beginnings and early exposure to sales instilled a relentless drive that continues to shape his leadership style.Joe’s journey to WisdomTree began with a cold call from a recruiter and evolved into a long-standing leadership role at one of the most innovative ETF providers in the industry. He fell in love with WisdomTree’s entrepreneurial culture and commitment to transparency, client outcomes, and constant innovation. Today, he leads a 50-person distribution team across the U.S. and Latin America, focused on providing consultative value to financial advisors rather than just pushing products.Grogan walks listeners through his approach to team structure and culture, emphasizing the importance of clear expectations, open communication, and professional development. His team spans national accounts, wires, RIAs, and enterprise channels, with a strong emphasis on career pathing from analyst roles to field sales. Weekly calls, one-on-ones, and a highly transparent performance tracking system help drive accountability while fostering healthy competition.Joe also discusses how CRM and AI tools have transformed his team's efficiency. From automated meeting notes to engagement-based compensation tracking, WisdomTree leverages data to reduce administrative burden and keep salespeople focused on high-impact client interactions. He views CRM entries not as micromanagement but as “gold bars” that unlock insights and create better investor experiences.Leadership, for Joe, is about servant mindset, vulnerability, and long-term retention. He believes in empowering his team, maintaining low turnover through trust and autonomy, and treating teammates like the professionals they are. Rather than managing activity for its own sake, Joe rewards outcomes and teaches his team to think like owners of their own territory.His advice to young professionals? Nail your current role. Master the fundamentals. Don’t worry about the next job—it will come if you focus on being excellent where you are. This episode is packed with tactical insight, cultural wisdom, and authentic leadership takeaways from one of the most respected distribution leaders in the business.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

May 6, 2025 • 44min
DeWayne Louis on Scaling Smarter with AI at Versor Investments
In this episode of the Rainmaker Podcast, guest host Pat Tighe welcomes DeWayne Louis, founding partner of Versor Investments, for a deep dive into how the firm uses technology, process, and leadership discipline to scale a lean, global investment business. With over 20 years of experience spanning hedge funds, private equity, and investment banking, DeWayne shares how his career shaped the culture and strategy behind Versor’s quantitative investment platform.Versor, managing approximately $1.4 billion in AUM, specializes in quantitative equity strategies including single stocks, event-driven, and global equity index futures, all powered by proprietary research and robust data infrastructure. Founded by a team that previously worked together at Investcorp, Versor’s mission was to spin out and commercialize the quantitative research insights they had developed over a decade of institutional investing.A central theme of the episode is Versor’s use of AI and automation to maximize efficiency. With just five people on the distribution team, the firm leverages tools like Salesforce, Microsoft Teams transcription, Motion AI for project tracking, and automated DDQ systems like Qvidian to streamline operations and boost productivity. DeWayne emphasizes that embracing AI isn’t optional—it's a strategic advantage. He shares how junior team members often lead innovation by identifying new tools, and leadership’s openness to those ideas allows the firm to stay nimble and competitive.DeWayne also walks through how the team organizes itself using OKRs and A+ projects—firmwide priorities with measurable outcomes that drive growth and innovation. These initiatives are reviewed and executed collaboratively by a partner group, ensuring alignment across departments and clear accountability.When it comes to fundraising, DeWayne discusses the evolving landscape and their expansion into the wealth management channel via new mutual fund products. He credits platforms like Dakota Marketplace for helping them efficiently reach a wider RIA audience.As both a player and coach, DeWayne shares leadership lessons on empowerment, trust, and mentoring. He advises younger professionals to become fluent in investment strategy, embrace technology, and approach relationships systematically. For fellow leaders, he stresses the importance of removing barriers to innovation and listening to voices at every level of the firm.This episode is packed with valuable insights for sales professionals, fundraisers, and distribution leaders looking to scale smarter with fewer resources and stronger processes.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

Apr 29, 2025 • 29min
Earning Trust, One Deal at a Time – Drew Dolan, DXD Capital
In this episode of the Rainmaker Podcast, host Gui Costin welcomes Drew Dolan, co-founder and principal of DXD Capital, for a compelling conversation on data-driven development, investor relations, and building a specialized real estate platform. With over 20 years in real estate and a deep passion for ground-up development, Drew shares how he transitioned from technical sales into leading one of the most forward-thinking firms in self-storage.Founded in 2020, DXD Capital was built on the belief that self-storage is a real estate-driven asset class where location and timing are everything. By leveraging a proprietary analytics platform, Radius+, co-created by Drew’s partner, DXD is able to assess rates, density, competition, and demographic trends with precision. This data-first strategy has helped DXD identify and develop prime self-storage projects across the U.S.—from Nantucket to Maui.Drew walks through the firm's capital strategy, explaining their evolution from a $63M LP fund to a flexible model incorporating both funds and one-off joint ventures with family offices. This structure allows DXD to cater to both high-net-worth individuals and large institutions, with a focus on customization, transparency, and performance. Drew emphasizes that communication is key—monthly updates, timely financials, and responsiveness help build trust with their 300+ investors.Internally, DXD runs a lean, focused operation with 30 employees spread across three main offices and remote locations near active projects. Slack and weekly check-ins are central to internal communication, while in-person retreats help maintain cultural connection. Drew also shares his leadership philosophy, centered around empowering others, encouraging ongoing learning, and hiring people who are better than him in key roles.From an IR standpoint, DXD recently expanded its team, bringing in professionals with strong relationship instincts and private equity backgrounds. Drew underscores that while industry knowledge can be taught, trust and human connection are what open doors. Their tech stack, including Juniper Square and HubSpot, helps them manage investor communication and track data, but Drew admits the most effective outreach still comes down to “hand-to-hand combat.”Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

Apr 22, 2025 • 29min
Driving Distribution with Discipline – Daniel Noonan, Cohen & Steers
In this episode of the Rainmaker Podcast, host Gui Costin sits down with Daniel Noonan, Executive Vice President and Head of Wealth Management Consulting at Cohen & Steers, to explore what it takes to lead and scale a top-tier distribution team in today’s evolving investment landscape. With more than two decades of experience at firms like Nuveen, PIMCO, and State Street Global Advisors, Daniel brings a thoughtful, measured approach to sales strategy, team leadership, and client engagement.Daniel offers an inside look at how Cohen & Steers is expanding beyond its core REIT franchise into private real estate, retirement solutions, and most recently, active ETFs. With a 50-person U.S. wealth distribution team, the firm is structured to stay agile while maintaining deep relationships across channels including RIAs, wirehouses, independent broker-dealers, and private banks.A central theme in the conversation is intentional sales process. Daniel emphasizes the importance of identifying the right advisor profile—those who embrace active management, endowment-style portfolio construction, and value in real assets. The firm leverages CRM technology, specifically Salesforce, as a “force multiplier,” empowering the sales team with data, segmentation, and efficiency to spend more time with high-potential clients. He stresses that success comes from combining the “art” of client engagement with the “science” of targeting and tracking.Daniel also discusses the challenges and opportunities of new client acquisition, particularly in the fast-growing but complex RIA channel. He advocates for a consultative, business-minded approach, focused less on product pushing and more on providing value—whether that’s market insight, operational advice, or branding strategy.On leadership, Daniel defines his style as collaborative, present, and servant-oriented. He believes in staying close to the business and investing time with his team to remove roadblocks and reinforce shared goals. He encourages open communication across levels, structured reporting, and measurable goals that prioritize effort and process over uncontrollable outcomes.For young professionals, his advice is to be a “student of the game”—stay curious, work hard, and differentiate yourself through depth and breadth of knowledge. His biggest challenge today? Focus. With multiple initiatives underway, Daniel’s priority is maintaining clarity on what matters most and building infrastructure to support that focus. This episode is a masterclass in strategic sales leadership and thoughtful organizational growth.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

Apr 15, 2025 • 26min
Michele Colucci on AI-Driven Healthcare at DigitalDx Ventures
In this episode of the Rainmaker Podcast, Michele Colucci, founder and managing director of DigitalDx Ventures, joins Gui Costin to discuss how artificial intelligence is revolutionizing healthcare diagnostics—and how her firm is leading the charge. With a background spanning law, technology, entrepreneurship, and venture capital, Michele brings a multidisciplinary approach to investing in early-stage diagnostic companies that leverage AI and data to detect disease earlier, more accurately, and with less invasiveness.Michele describes the mission of DigitalDx: to identify startups that enable faster, more accessible diagnostics for major diseases, particularly in areas like neurology where early detection is critical but traditionally difficult. She explains that the human body is essentially a data problem—and that by harnessing AI, it becomes possible to detect issues long before symptoms appear. One of the firm’s standout investments includes an FDA-approved over-the-counter syphilis test with a 10-minute result time.She walks listeners through the firm’s investment criteria, focusing on statistically significant sample sizes, scalability, and team coachability. DigitalDx looks for companies under a $20 million pre-money valuation and plays an active role post-investment, often joining boards and supporting portfolio companies through major growth milestones. Michele emphasizes the power of deep bench support—her team includes experts from NVIDIA, Stanford, Siemens, and more—alongside an innovative “Entrepreneur in Residence” program and a fellowship that sources global deal flow while nurturing underrepresented talent in venture capital.DigitalDx distinguishes itself not just by investing capital, but by offering founders access to a robust, highly experienced network that helps de-risk startups across science, regulatory, reimbursement, and go-to-market strategies. Michele also touches on the importance of aligning passion with professional purpose, both for her team and young professionals entering venture capital. Her leadership style prioritizes conviction, team ownership, and positivity, steering away from zero-sum thinking and toward collaborative problem-solving.As Michele reflects on market headwinds, she points to fundraising as a current challenge but emphasizes that conviction-driven investors—those looking ahead to where innovation is going, especially at the intersection of AI and healthcare—are best positioned for long-term success.This episode offers a powerful look into how visionary leadership, deep domain expertise, and a mission-driven model can reshape the future of healthcare investing.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

Apr 8, 2025 • 30min
Scaling Private Wealth with Doug Krupa, KKR
In this episode of the Rainmaker Podcast, host Gui Costin welcomes Doug Krupa, Managing Director and Head of Global Wealth Solutions in the Americas at KKR. Doug shares the story of his career—from his early days as a financial advisor working with New York City firefighters to leading one of the most innovative wealth distribution platforms at KKR. His passion for making private markets more accessible stems from those early experiences, where he saw firsthand how institutional allocations to private equity contributed to long-term success.Doug walks listeners through the structure and mission of his team at KKR, which has grown significantly since he joined in 2019. Focused on intermediaries like financial advisors and RIAs, his team has developed evergreen investment solutions across asset classes, delivering institutional-quality strategies in a more accessible format. He emphasizes a localized, relationship-driven approach, with team members embedded in major metro markets across the U.S.Communication and process are at the heart of Doug’s leadership style. KKR’s wealth team operates with a high level of collaboration, leveraging instant messaging, a custom CRM, and content centralization platforms to share real-time insights, content, and KPIs across channels. Weekly sales meetings and monthly all-hands calls ensure the team stays aligned, while quality interactions, new advisor penetration, and sales versus budget remain key performance indicators.Doug also discusses how his team prioritizes rapid communication of what’s working (and what’s not), and the importance of tracking structured client feedback through CRM. His leadership philosophy centers around curiosity, responsiveness, and removing roadblocks for his team. He likens himself to a “chief agitation officer,” continually challenging the status quo to improve transparency, technology, and product innovation.For young professionals entering investment sales, Doug encourages a relentless curiosity, a willingness to ask “why,” and involvement in product development and messaging—skills that not only build credibility but also fuel long-term career growth. He stresses the importance of education, noting that broader adoption of private markets relies on helping advisors and clients better understand the asset class.This episode is a must-listen for distribution leaders and sales professionals seeking to scale their efforts, adopt a tech-forward sales strategy, and drive long-term engagement through thoughtful innovation.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

Apr 1, 2025 • 48min
Guantong (“GT”) Sun on Process-Driven Fundraising at Turning Rock Partners
In this episode of the Rainmaker Podcast, host Gui Costin sits down with GT Sun, Senior Vice President of Investor Relations at Turning Rock Partners, for an engaging conversation about data-driven fundraising, leadership, and building trust in the world of private credit. GT shares his dynamic career journey, from humble beginnings in the AIG mailroom to working at Lehman Brothers during the 2008 financial crisis and later helping build out fundraising operations at firms like Fortress, Golub Capital, and Pretium. His experience spans both the client-facing and operational sides of capital formation, giving him a unique perspective on the intersection of data, relationships, and process.At Turning Rock, GT leads a small, nimble investor relations team and emphasizes process as a cornerstone of success. He walks listeners through their disciplined weekly cadence, from Monday partner meetings to regular pipeline reviews and strategic engagement planning. He highlights the importance of communication, preparation, and execution—drawing parallels between the sales process and the investment process. GT emphasizes how using case studies to tell the firm’s story and show live deal execution helps investors connect with the firm’s strategy in a tangible way.One of the key takeaways from the conversation is GT’s focus on process, particularly CRM and data management. He discusses the critical role a robust CRM plays in managing LP relationships, tracking touchpoints, and driving accountability across the sales process. GT underscores the need for clean, accurate, and regularly updated data to keep fundraising efforts efficient and effective. He also explains how capturing detailed notes and tracking patterns in investor questions helps tailor messaging to different audiences, whether pensions, insurers, or consultants.GT also shares his leadership philosophy—"be a captain on the team"—highlighting the importance of preparation, attention to detail, and humility. He leads by example, believes no task is too small, and stresses the value of clarity, respect, and integrity. For younger professionals, his advice centers around building trust, staying curious, and viewing every experience as an opportunity to compound your skills over time. His passion for the work and belief in continuous improvement shine throughout the episode.This episode offers a masterclass in combining discipline, empathy, and process to build lasting investor relationships in a competitive fundraising landscape.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.


