Dakota Rainmaker Podcast

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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.

6D AGO

Dominica Ribeiro: Marketing and Distribution Under One Roof

In this episode of The Rainmaker Podcast, Gui Costin sits down with Dominica Ribeiro, Chief Marketing and Distribution Officer at Breckinridge Capital Advisors, the legendary asset manager based in Boston. The conversation covers Dominica's non-traditional career path, the structure and discipline of Breckinridge's distribution team, and the leadership philosophy that has shaped how she runs sales and marketing as a single integrated function. Dominica started full-time in the industry directly out of high school at Putnam Investments, working through her associate's, bachelor's, and master's degrees while building her career. After 5 years at Putnam, she spent 14 years at Fidelity, including a long stretch at Pyramis Global Advisors in Smithfield, Rhode Island, where she worked institutional marketing in lockstep with the distribution team. That alignment of marketing and sales, unusual in the industry, became the foundation for her current role at Breckinridge, where both functions sit under her leadership. Breckinridge is a 30+ years old independent asset manager with roughly $55 billion in AUM (as of 3/31/26) and 89 employees across offices in Boston and San Diego. The firm specializes in investment-grade fixed income and equity income portfolios delivered through customized separately managed accounts. Despite its size, the firm operates with a deliberate boutique feel, and Dominica's 20-person distribution and marketing team is structured to reinforce that. She walks Gui through how the team is organized, two regions split east and west of the Mississippi, with specialized state-level coverage, plus dedicated private wealth, institutional, national accounts, and distribution strategy teams. A key theme of the conversation is continuity of relationship. Breckinridge does not hand prospects off from sales to a separate relationship management team. The same person who brings the client in stays with them through quarterly updates and ongoing engagement, which Dominica believes drives better retention and cross-sell. That continuity is reinforced by a transparent scorecard that incentivizes business development, retention, execution, and collaboration, shared with the team in January so reps know exactly how they will be measured. Dominica is candid about CRM implementation. Breckinridge uses Salesforce, and her advice to boutique managers considering a CRM rollout is simple: don't do it without a dedicated sales enablement or operations resource. The cost only pays off when someone is responsible for data discipline and reporting consistency. Gui shares how Dakota has integrated Slack, Salesforce, and Claude to make meeting note capture nearly frictionless, eliminating the most common source of CRM data decay. The conversation closes on leadership. Dominica describes herself as leading with empathy while holding a high bar, direct when the team falls short, transparent about expectations, and clear that proactive communication is non-negotiable. Her advice to early-career salespeople is to trust their gut and communicate constantly, even in internal-facing roles. Looking ahead, she names focus as her biggest challenge: at 89 employees, the firm has to be disciplined about where it invests its time, talent, and resources, and the feedback loop from clients and prospects is what drives those decisions. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

41 min
MAY 5

Keith VanOrden on Building TCW's Retail Distribution Platform from Scratch

In this episode of The Rainmaker Podcast, Gui Costin sits down with Keith VanOrden, Head of Retail Distribution for North America at TCW. Keith brings nearly 30 years of experience building and leading sales teams, including more than 13 years at BlackRock, most recently as the national sales manager for iShares, and earlier roles at Delaware Investments, Fidelity, and Putnam, where he started his career in Boston. The conversation opens with Keith's origin story growing up in Philadelphia, attending Syracuse where he met his wife Toby, and his early internship at Smith Barney that pointed him toward distribution. He shares how a literal steno notebook, started during his wholesaling years, became the blueprint for his approach to leadership. Tracking nine different sales managers across six years, he identified the two traits that mattered most: trust and having walked in the team's shoes. When Keith joined TCW three years ago, the firm had great active fixed income, concentrated equity portfolios, and a strong legacy in private credit and asset-backed finance but no retail sales team. He built one from scratch, drawing on the notes and patterns he'd been collecting for decades. Today the team includes 15 internals, 14 in the wirehouse and independent channels, 9 in RIA, and a wealth portfolio consulting team built around white-glove service. Keith and Gui dig into the channelization debate, agreeing that the right answer depends on team size, product breadth, and where revenue actually lives. They unpack TCW's sales process anchored in Sequoia training, transparent alignment between salesperson, client, and firm interests, and a disciplined follow-up cadence. They also break down CRM as the lifeblood of distribution, with Salesforce, voice-to-text dictation, automatic internal follow-ups, and 100% adoption. Keith shares a study that overturns the old 4–6 touchpoints-per-year rule the real number is 8–12 and explains why digital engagement signals have to feed into the CRM to capture the full picture of an account. On communication, Keith emphasizes Team chats over email, including channels he doesn't even know about, which he sees as a healthy sign. He runs annual "retirement parties" for bad ideas and standing meetings that have outlived their usefulness. Gui shares Dakota's check-in cadence short, momentum-driven, never about performing for the boss. Keith reflects on managing up after 14 years with the same boss, emphasizing that he never coasts on the relationship. He describes his leadership style as servant leadership and tells the Ed Harris / Gulf and Western story every time Harris got a big job, he asked his team what they needed to succeed, and then he gave it to them. Keith looks for four traits in salespeople: natural curiosity, work ethic, a development mindset, and genuine love for the business. He closes on his biggest challenge: knowing when to pivot versus when to stick with what's working. Sometimes the highest-leverage move is to keep doing exactly what's working and trust the discipline. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

49 min
APR 28

Stephen Tiller on Leadership, AI, and Picking Up the Phone

In this episode of The Rainmaker Podcast, Gui Costin sits down with Stephen Tiller, who joined Sterling Global Financial roughly 13 years ago after a 35-year career across some of the most respected names in real estate finance and investment banking. Sterling, founded by David Kosoy more than 50 years ago, manages roughly $7–8 billion in assets across six countries and runs a platform that includes private credit lending funds, development and construction businesses, trust companies, and banks. Stephen describes it as a microscopic-scale version of the Brookfield or Blackstone model, with real estate as its DNA. The conversation opens with Stephen's origin story growing up in a northern Ontario mining town, playing varsity hockey at Western, and starting his career at CB Richard Ellis as it was first entering Canada. He spent the 1990s working out distressed real estate and financial companies at RBC Capital Markets, an experience he credits as foundational to how Sterling underwrites and builds products today. He later ran the merchant bank at Brascan under Bruce Flatt, and led global investment real estate banking at Bank of Montreal before joining Sterling. On sales, Stephen explains that distribution is Sterling's number-one priority. The firm's Canadian retail engine runs through FundServ the platform owned by the major Canadian banks and dealers which connects the firm to thousands of retail investors. Once approved, the platform allows an IA in Vancouver to invest a client on Friday after a Thursday request. But the efficiency of the back end only works if the front end is covered: Sterling's sales team is built around managing the IA and RIA channels, understanding each advisor's book and decision-making. Communication inside the firm is high-touch and high-frequency, with twice-weekly calls at critical junctures. Stephen leans heavily on time-tested sales discipline tell them what you're going to do, do it, then tell them what you did combined with a modern tech stack including HubSpot, Asana, and a growing AI layer. He's candid that Sterling is "on the 5-yard line" with AI but treats it as a top-down priority, with senior executives leading the rollout themselves. On leadership, Stephen credits founder David Kosoy, who at 60+ years in the business is still first in the office. He emphasizes buy-in by example, boots-on-the-ground decision-making, and picking up the phone which he argues has become a real leadership differentiator as email turns into a CYA tool. His marina infrastructure example captures it: only by being physically on site did the team realize they didn't have a development site with a marina, they had a marina with a development site. His advice for young professionals: ask better questions and anticipate where the puck is going, not where it is. He closes on the biggest challenge facing the industry today the pace of regulatory and geopolitical change and his answer to it: grow or die. Constant improvement, reinvesting in people, and adapting the business, because the people are 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.

22 min
APR 21

Jeff Collins: Selling What Doesn't Fit in a Bucket

In this episode of The Rainmaker Podcast, Gui Costin sits down with Jeff Collins, Managing Partner of Cloverlay, for a deep conversation on what it takes to raise institutional capital for one of the most differentiated strategies in private markets. Cloverlay, now on its fourth fund, invests exclusively in uncorrelated, non-operating assets — wireless spectrum, intellectual property on the content side, Broadway theatrical rights, litigation finance, pharmaceutical royalties, and other esoteric assets that don't sit neatly inside traditional buyout, credit, or real asset buckets. The result is a firm with a sales challenge that's fundamentally different from its peers: Cloverlay isn't competing to be the best CLO equity fund in a crowded category. It's competing to be understood at all. Jeff walks through the origin story of Cloverlay, his decade-plus at Morgan Stanley Alternative Investment Partners, and the realization that the "special situations" work he was doing there — the completion-portfolio assets absent from most institutional allocations — deserved to be its own firm. He initially thought Cloverlay would be a family office and multifamily office strategy. Instead, 85% of the capital came from true institutions: public pensions, corporate pensions, and the most sophisticated allocators in the world. That reality shapes everything about how Cloverlay goes to market. Jeff argues that positioning is the entire game when you're selling something no LP has a bucket for. The firm has sharpened its pitch down to four sentences, leading with "uncorrelated assets, and you don't own them" and immediately moving to concrete examples. The mechanics of the 60-minute meeting get significant airtime: Jeff and Gui agree that the default structure — firm background, two questions, 40 minutes of the LP talking — isn't really a meeting. Cloverlay intentionally breaks that muscle memory by asking questions most LPs rarely field, pulling them out of autopilot and forcing them to start slotting Cloverlay into their portfolio in real time. The CRM is the backbone of Cloverlay's sales discipline. A 9 AM Monday sales meeting runs every week, organized by relationship owner rather than as a report-out, with senior investment and sales leadership triangulating on every target. Gui and Jeff then dig into how AI is transforming what's possible with relationship data — Dakota's Claude-in-Slack tool surfacing full four-year customer histories, and Claude coming to Dakota Marketplace — while making clear that none of it works without disciplined data entry upstream. Jeff closes with a candid assessment of the current fundraising environment: in 30 years, he has rarely seen new relationships harder to secure. Unlike the post-GFC period, when allocators leaned into opportunistic trades, today's LPs feel no urgency — they can simply wait. The firms that win in this environment are the ones finding the minority of allocators who still view differentiated strategies as a solution to uncertainty. And for any GP eyeing international capital, Jeff leaves a concrete tactical note: the Middle East operates entirely on WhatsApp. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

39 min
APR 14

Mike Castino on Market Makers, Platform Fees, and Building a Boutique ETF Firm

In this episode of the Rainmaker Podcast, Gui Costin sits down with Mike Castino, President of Sound Capital Solutions, for a deep dive into the mechanics of ETF creation, distribution, and the accelerating structural shift reshaping investment management. Mike's career began on the floor of the Chicago Mercantile Exchange, where he spent 12 years as an independent futures trader before transitioning into the investment management industry. His first sales role came at Claymore ETFs — one of the original ETF families, eventually acquired by Guggenheim and later Invesco — where his trading floor instincts translated directly into his commercial style. From there, Mike spent over a decade at U.S. Bank Global Fund Services, building out the business development function for ETF administrative and custodial services from the ground floor into a high-revenue operation. Sound Capital, the firm he co-founded with Claymore veteran Nick Dalmasso, was born from a shared entrepreneurial itch and a clear view of where the industry was heading. Sound Capital operates two complementary businesses: a white label ETF advisory service, where the firm serves as the registered advisor for clients who want to launch funds without building their own infrastructure, and a solutions provider offering that supports asset managers before, during, and after launch. Unlike traditional consultants who parachute in with a plan and leave, Sound Capital positions itself as a long-term partner focused on helping clients both build and retain AUM. A major theme of the conversation is the mechanics behind getting an ETF to market — and the parts that most first-time issuers underestimate. Revenue sharing with broker-dealer platforms is more complex and more negotiable than it appears, with fees ranging from flat access charges to AUM-based percentages to paid data packages. Market maker relationships are similarly misunderstood: firms like Jane Street and Citadel are not standing by as utilities for any issuer that arrives. They are selective partners who respond to seed capital, credible distribution plans, and meaningful trading relationships. Mike and Gui also discuss the transparent versus non-transparent active ETF debate, where Mike is direct: the flows have settled the argument. Non-transparent structures have failed to gather meaningful organic assets, while transparent active ETFs have surged — and the front-running fears that once justified opacity are largely overstated for anyone outside of micro-cap strategies. The conversation closes on two forward-looking topics. First, the dual share class structure — now approved for 30+ firms beyond Vanguard — which Mike sees as the long-term bridge that will unlock sticky mutual fund assets as intermediaries build switching infrastructure. Second, the challenge of building a young firm's credibility in a market that prizes institutional tenure. Mike is candid: individual experience only goes so far when prospects are evaluating the firm itself, and the answer is simply to deliver exceptional work, every day, one client at a time. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

36 min
MAR 17

Paul Stanton on How Founder-Led Brands, Content Marketing, and Agentic AI Are Reshaping Capital Raising

In this episode of the Rainmaker Podcast, Gui Costin sits down with Paul Stanton, a partner at Thesis Driven and PTB, a real estate investment banking boutique. The conversation spans Paul's career journey, the power of content marketing in the investment world, and the transformative potential of AI for business builders. Paul's path into real estate began after college at the University of Richmond, where he started in brokerage at Newmark before moving to the investment and development side. He later pursued a forward-thinking thesis around flexible office space, acquiring boutique Class B office buildings and operating them under co-working brands, a strategy that was derailed by COVID-19. Rather than retreating, Paul pivoted and launched an investment bank focused on operationally complex, niche real estate strategies, including outdoor hospitality, sports infrastructure, and surf infrastructure. This work eventually merged with Thesis Driven, a real estate media company he co-founded with entrepreneur Brad Hargreaves, focused on innovation in the built world through a capital markets lens. A central theme of the conversation is the untapped opportunity for investment managers to build audiences through content marketing. Paul and Gui agree that the investment management industry represents the largest white space in content marketing today, most firms hide behind corporate brands and compliance concerns rather than humanizing their story. Both point to Jon Gray of Blackstone and Andreessen Horowitz as rare examples of founder-led brands that have embraced media to build trust at scale. Paul notes that the psychology behind this is rooted in parasocial relationships, when someone sees your face and hears your voice consistently, their brain begins to feel like it knows you, which creates a powerful foundation for trust in capital raising. Paul shares his own experience building a LinkedIn presence over the past year, emphasizing that the mental shift that got him started was reframing content creation from self-promotion to education. By sharing what he was seeing in the capital markets and emerging asset classes, he found an authentic voice that resonated with his audience. Gui echoes this, noting that the most engaging posts are never about funds or accolades, they're about real experiences, lessons learned, and genuine insight. The episode closes with a discussion on AI and its implications for business. Paul introduces the concept of agentic AI, specifically his experience setting up an AI-powered capital markets analyst named "Sarah" using an open-source local infrastructure tool. Sarah reasons through tasks, builds databases, drafts email campaigns, and conducts research autonomously. Paul describes the experience as the most mind-blowing development he's seen since first using ChatGPT, underscoring the idea that AI agents are beginning to function like real employees. When asked about his biggest challenge, Paul cites focus, the entrepreneurial temptation to chase every new AI-driven opportunity rather than staying disciplined on core priorities. It's a fitting note to end on: in a world of expanding possibility, clarity of purpose remains the competitive edge. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

44 min
MAR 3

Be Kind and Win: Gui Costin, Dakota

In this special episode of The Rainmaker Podcast, Gui Costin is interviewed about his book Be Kind. He reflects on early leadership missteps marked by volatility and ego, and the turning point that reshaped his approach to culture and accountability. Gui challenges the belief that high performance requires harshness, arguing instead that kindness and hard standards can coexist. He draws a key distinction between being “nice” and being “kind,” emphasizing direct, respectful feedback over avoidance. The episode reinforces a core leadership principle: words, tone, and daily behavior from the top ultimately define culture and performance. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

23 min
FEB 17

Michael Sidgmore on Winning the Wealth Channel

In this episode of The Rainmaker Podcast, Gui Costin sits down with Michael Sidgmore, Partner and Co-Founder of Broadhaven Ventures and Founder of Alt Goes Mainstream, to unpack one of the most important structural shifts in asset management today: the convergence of private markets and private wealth. Michael begins by walking through his path from growing up outside Washington, D.C., to studying at the London School of Economics, where he first gained exposure to private markets by leading one of the world’s largest student-run hedge fund and private equity conferences. That early immersion led to roles at Goldman Sachs’ Principal Strategic Investments group, early-stage operating experience at Mosaic, and ultimately a formative stretch at iCapital, where he helped build distribution efforts pre-product, with a blank slate approach to the wealth channel. That experience shaped his long-term thesis: private markets are becoming mainstream, and the infrastructure supporting them must evolve accordingly. At Broadhaven Ventures, Michael invests across fintech, asset management, and market infrastructure businesses that sit between general partners (GPs) and limited partners (LPs). His focus centers on the “plumbing” of private markets, from pre-investment distribution to post-investment reporting and analytics, particularly as more capital flows in from the wealth channel. The conversation then turns to Alt Goes Mainstream (AGM), Michael’s media platform designed to educate both private markets professionals and wealth managers about their growing intersection. His “north star” is clear: education drives allocation. As large asset managers increasingly prioritize private wealth distribution, they must rethink branding, marketing, and direct engagement. Meanwhile, wealth managers must better understand how private markets firms operate, structure products, and build long-term partnerships. Gui and Michael explore the evolving role of brand in asset management. Distribution, they note, is expensive and operationally complex, but firms that invest in both boots-on-the-ground sales and aerial marketing support can “own the narrative.” In an environment where attention is fragmented and algorithms are controlled by third parties, direct communication, whether through podcasts, newsletters, or owned media studios, has become a strategic advantage. Ultimately, the episode highlights a defining industry shift: distribution is no longer optional for firms seeking scale. As private markets expand into wealth, success will favor those who combine infrastructure, education, and authentic brand-building to meet in the middle. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

51 min

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.

Creator

Dakota Team
Years Active

2024 - 2026
Episodes

86
Rating

Clean
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© 2026 Dakota Rainmaker Podcast
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