Dakota Rainmaker Podcast

Hosted by Dakota Team

Business Management

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Oct 2026

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About the show

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.

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October 20, 202637 min

The Art of Subtraction: Sales Leadership Lessons from Wellington’s Chip Saltz

In this episode of the Rainmaker Podcast, Gui Costin sits down with Chip Saltz, head of US Wealth Alternatives Distribution at Wellington Management. Chip leads the firm’s advisor sales efforts for its hedge fund and private investment capabilities across wirehouses, independent and regional broker-dealers, and RIAs. Before Wellington, he held distribution roles at Harrison Street Private Wealth, Versus Capital Advisors, Starwood Capital Group, and John Hancock. Chip starts with his origin story. He grew up in New Orleans, bartended through college at a fine dining restaurant, and was drawn to wholesaling by the Morgan Keegan professionals who came in for dinner. He got his start at Wood Logan, the distributor for Manulife and John Hancock, where a mentor taught him a formula for success: the quality of your presentation times the quality of your product times the frequency you see people. The key, he says, is that the product is you. He later moved to WP Carey to sell non-traded REITs, then to Starwood, and now Wellington, where he is building a dedicated wealth business. Gui and Chip agree that the core of a great fundraiser is hard work and likability, which can’t be taught, along with the ability to consistently book meetings with qualified buyers. Chip explains that alternatives sales depend on helping advisors understand structure, liquidity, and operational constraints, because those details are part of the product. The conversation then turns to how Chip runs his team. Wellington has 7 external wholesalers, with plans to grow to 12 to 14, plus internal wholesalers and sales specialists. Chip describes the internals as living in both the past and the future, prospecting ahead and following up on what already happened. Because advisors may allocate only around 5% of a portfolio to these products, he says it takes 8 to 12 touches, not the 3 to 6 often cited, so the team has to stay ever-present. His communication rhythm includes a collaborative Monday sales call, Wednesday product office hours, regular one-on-ones, and a monthly sales momentum call that ends with deliverables, decisions, and ownership. They also discuss the role of the CRM and AI. Chip calls the CRM table stakes and says personal notes help build relationships. Wellington has reduced meeting logging from 90 minutes to 90 seconds, and Chip expects AI dictation to bring it down further. Gui shares how he dictated call notes into Claude and sent them into Salesforce. On leadership, Chip says he leads from the front, holds people accountable, gives direct feedback, praises publicly, and corrects privately. He adds that simplicity isn’t dumbing down, it’s discipline, so that a team’s best use of time is in front of advisors. His advice for young salespeople is to understand your product deeply instead of memorizing a pitch, read widely, become the person you’d want to work with, ask for the order, and bracket your time. Chip names Influence by Cialdini as a go-to, and Gui recommends The Challenger Sale. Asked about his biggest challenge, Chip points to prioritizing finite time. He picks 2 to 5 items that move the business forward and says no to the rest, calling the business the art of subtraction.

October 13, 20261 hr 3 min

Culture Is the Strategy: Christina Adamson of Ares Wealth Management Solutions

In this episode of the Rainmaker Podcast, host Gui Costin sits down with Christina Adamson, Partner and Co-Global Chief Operating Officer of Ares Wealth Management Solutions, to unpack how a disciplined, people-first approach helped Ares grow its wealth business roughly 50x in five years across eight evergreen funds. Christina previously held roles at Citigroup, Deutsche Bank, and Black Creek Capital Markets before joining Ares in 2021. The conversation opens with communication, the foundation of any fundraising role. Christina explains that early alignment with the people you serve on their three-to-five-year goals, followed by a steady cadence of short touchpoints, keeps everyone on the same page. Updates should not be weather reports; they should share intelligence that helps the recipient do their job better. Gui adds that every interaction with a prospect is an audition for what working with you will feel like after they invest. Christina's unsolicited advice for salespeople is to outwork everyone, stay curious about what the prospect is trying to solve, and cut out the noise to focus on building trust. If you can't say a prospect trusts you, she says, you're in the wrong business. From there, the pair dig into culture as a competitive advantage. Christina credits CEO Mike Arougheti for setting the tone, with an emphasis on collaboration, transparency, trust, and no egos, alongside real autonomy for leadership teams. Gui adds that clear standards free people up to execute. Both acknowledge that protecting culture as a firm scales sometimes requires actively managing out people who aren't the right fit. The discussion turns tactical when Gui and Christina explore how technology supports a team of 200 people across 15 offices. Christina describes Ares' use of Teams channels to share intelligence in real time, and both stress a simple rule: if a meeting isn't logged in the CRM, it didn't happen. Gui calls missed call notes "gold bars" left on the table, and they discuss dictating a call report in the lobby, letting AI polish it, and routing it automatically to the right colleagues. Christina explains how Ares layers distribution intelligence and AI into its CRM so reps start each day knowing where to focus, while the relationship manager remains irreplaceable. Gui cautions that collecting data is only half the job; keeping it updated takes a process. Hiring gets significant airtime. Christina meets every candidate, from summer interns to managing directors, and looks first for drive, then a blend of EQ and IQ, and a desire to be part of a team. They discuss why former competitive athletes tend to thrive in sales, conditioned to handle rejection without self-pity, and why setting clear expectations in interviews lets candidates opt out early. Gui shares Dakota's monthly "W Days," where teams explain what is and isn't working, and Christina recalls her father's advice to "make it ugly." They close on leadership focus: doing only what only you can do, and investing in the "not urgent but important" work that drives transformative growth.

September 29, 202632 min

If It's Not in Salesforce, It Didn't Happen: Michael O'Shea on Sales Discipline at Origin Investments

In this episode of the Rainmaker Podcast, Gui Costin sits down with Michael O'Shea, Director and Head of Private Wealth Solutions at Origin Investments, for a wide-ranging conversation about systems, discipline, and what it actually takes to build a durable capital-raising career. Michael's path into the business started almost by accident nearly two decades ago, when curiosity about what a REIT and a Series 7 actually were pulled him into calling on advisors and raising capital for niche, tax-advantaged real estate deals. That early curiosity turned into a genuine passion for investing, which he later formalized by going back to school for an MBA in real estate finance and earning his CFA charter, a credential he says fundamentally sharpened how he talks about markets and builds trust with advisors. Michael shares the origin story behind Origin Investments itself: a Chicago-based real estate manager founded by two former Mercantile Exchange traders, Michael Episcope and David Scherer, who built significant personal wealth trading before computers pushed traders out of the pits. Rather than keep taking on trading risk, they built Origin to invest more transparently and with better alignment than what they'd experienced themselves as investors. Nineteen years later, the firm manages $5 billion in assets, supports more than 5,000 investment partners, and now partners with 165 RIAs, all distributed through a lean, fully RIA-and-family-office-focused team of five reps plus Michael and a sales enablement associate. A major thread of the conversation is Michael's belief that systems, not goals, drive consistent fundraising results. He leans on an Olympics analogy: the goal is gold, but it's the underlying training system that actually gets an athlete there. Applied to sales, that means knowing exactly who you're calling on, mastering your product, and building weekly, monthly, and quarterly cadences with real process improvement baked in. That same discipline extends to pipeline management. Michael reviews his team's pipeline every week specifically to catch staleness or inflated deal sizes, a philosophy Gui strongly echoes: the best salespeople who raise the most money are the ones who keep the tightest, most accurate pipelines, especially when no one else is watching. The two also dig into how technology has changed the day-to-day of fundraising. Michael describes Salesforce as his daily "cockpit," now supercharged by AI tools that transcribe calls and voice memos directly into call notes and tasks, removing much of the friction and dread that used to come with logging activity. Gui ties this back to his own hard rule at Dakota: if it's not in Salesforce, it didn't happen, because that documentation is exactly what a sales rep's salary is paying for. On leadership, Michael describes himself as a coach who removes roadblocks and filters out noise for his team, while holding a firm, non-negotiable line on entering call notes. His advice to young fundraisers centers on continuous self-investment, learning AI tools, coding, and new skills, so they're preparing not just to be a great analyst, but eventually a great CEO. He closes by naming his current challenge: a capital markets backdrop where the 10-year Treasury and cap rates aren't behaving as expected, making long-term, illiquid asset classes like real estate a harder sell in the near term. Disclaimer: All Origin Investments statistics referenced herein — including assets under management, investor count, RIA partner relationships, and any projections, targets, or track-record figures — are as of September 1, 2026, are derived from Origin's internal records, and are unaudited. These figures are subject to change and are not indicative of future results.

September 22, 202647 min

Autonomy with High Expectations: Angela Kay on Leading Without Micromanaging

In this episode of the Rainmaker Podcast, Gui Costin sits down with Angela Kay, President of BasePoint Advisors and Global Head of Capital Markets, to trace her path from an accidental start in finance to leading distribution at a $7 billion private credit platform. A political science and public policy major at the University of Pennsylvania who spent a college year working in the Clinton White House, Angela graduated in 2002 into a post-9/11 hiring freeze and landed, almost by chance, as a research assistant at a global macro hedge fund in New York. From there she earned a master's in public policy from UCLA while working as a sovereign debt analyst at TCW, then helped launch Ice Canyon, a joint venture with Canyon Partners, where she raised the firm's AUM from zero to $4.25 billion before eventually joining BasePoint in 2020 to help institutionalize the business and build its SEC-registered advisory arm. The conversation's core theme is Angela's belief that effective fundraising starts with investment fluency: she describes herself as an investor first and a fundraiser second, and argues that the best fundraisers bridge portfolio knowledge with genuine curiosity about what an LP is actually trying to solve, not just what they're asking on the surface. Gui builds on this, framing fundraising not as a "salesperson" function but as a professional, consultative discipline built on long-term relationships that can span decades and evolve into genuine friendships. The discussion moves through several practical themes: the value of cold outreach (Gui's line, "you're one email away from a 20-year relationship," anchors this segment), the importance of prioritization over busyness, and structured but human communication both within a distribution team and up to a firm's executive committee. Angela describes BasePoint's team structure, organized by investor type and geography, built around a "team sport" mentality rather than siloed coverage, and her rule that every meeting should end with clarity on where things stand, not vague reassurances like "great meeting." A significant portion of the episode focuses on the CRM as institutional memory: Angela stresses entering notes in real time rather than deferring them, drawing on her own experience migrating a firm onto Salesforce years ago. Both she and Gui highlight how AI has changed this workflow, removing the friction and dread salespeople associate with writing call notes and making it dramatically faster to capture and later mine years of accumulated information. The episode closes with two reflective questions. Asked to describe her leadership style, Angela offers "autonomy with high expectations,” hiring for curiosity, organization, and drive, then giving her team room to operate against clearly stated annual goals. Asked for advice to young salespeople, she emphasizes humility: enter meetings to learn rather than to prove expertise, admit what you don't know, and protect your reputation, since it compounds over a career just like capital does. Disclaimer: Angela Kay is President of BasePoint Advisors LLC ("BPA"), an investment adviser registered with the U.S. Securities and Exchange Commission, and also serves as Global Head of Capital Markets at BasePoint Capital LLC, an affiliate of BPA that is a commercial service provider to separately organized lending subsidiaries. See Items 10 and 11 of BPA's Form ADV Part 2A. This content reflects Ms. Kay's personal views and is provided for general informational purposes only. It is not investment, legal, or tax advice, or an offer or solicitation to invest in any fund.

September 15, 202631 min

The Long Game: Ava Mallin on Building Allocator Relationships That Last

In this episode of the Rainmaker Podcast, Gui Costin talks with Ava Mallin, Managing Director in Private Wealth at Ardian, about her non-traditional path from an English degree into fundraising, and what she's learned leading private wealth relationships across the US. Ava shares how emotional transparency informs her leadership style, why daily feedback is more effective than annual reviews, and how a strong CRM — with Dakota as an overlay — has become essential infrastructure for her team. She also discusses hiring for culture fit over individual qualification, and why allocator relationships should be built with a long-term mindset rather than around a single fundraise.

July 7, 2026Episode 139 min

If You're Explaining, You're Losing: Mark Allen of Royal Oak Realty Trust

In this episode of The Rainmaker Podcast, Gui Costin talks with Mark Allen, President and Chief Development Officer of Royal Oak Realty Trust, about building a fundraising operation from the ground up in an industrial REIT. Mark covers how Royal Oak grew its distribution team from three to eight by hiring geographically rather than by channel, why shared account ownership beats ring-fencing relationships, and how disciplined communication, CRM tools, and AI-powered call notes are reshaping the sales motion amid heavy RIA consolidation. He and Gui also unpack his player-coach leadership style and the fundraising formula he's taken from The Tao of Fundraising — why simplicity beats complexity every time.

May 19, 202635 min

Dan Amir: Inside Crow Holdings' Wealth Distribution Playbook

In this episode of The Rainmaker Podcast, Gui Costin sits down with Dan Amir, Managing Director of Investor Coverage at Crow Holdings, for a wide-ranging conversation on building a wealth distribution team, applying institutional rigor to the wealth channel, and leading a sales organization through a difficult fundraising environment. Dan grew up in New Jersey, spent the first 13 years of his career in New York at BNY Mellon and Morgan Stanley in relationship and distribution roles, and made the pilgrimage to Dallas in 2017 — pre-COVID, before it was cool to go south. He joined Crow Holdings, the Dallas-based real estate investment and development firm founded by Trammell Crow, which today operates a development platform across multifamily and industrial sectors in 20 offices nationwide and an investment management business spanning industrial, multifamily, manufactured housing, self-storage, retail, and student housing. Crow Holdings Capital started its partnership journey in the institutional world — foundations and endowments first, then pensions and sovereign wealth. Over the last six years, the trajectory of growth in private real estate has shifted decisively toward the individual wealth community, which is why Dan was hired to lead a dedicated wealth coverage effort. His team of four (going to five) is structured geographically rather than channelized, with deliberate diversity of backgrounds — RIA, wirehouse, and non-linear distribution paths — to create overlap with how RIAs, wirehouses, and private banks actually behave in a market. Dan and Gui dug deep into the discipline of communication: starting every year with a written business plan, measuring weekly against benchmarks, and once a quarter looking back at the original plan. Communication up to leadership is succinct by design — pull data from Salesforce, summarize the position on each strategy, and engage the executive team only on genuinely strategic decisions. Dan emphasized the judgment of knowing when you need executive input. The CRM is the backbone of the operation, and AI sits on top of it. Dan ranked the CRM as indispensable for activity tracking, goal measurement, meeting note memorialization, and populating pre-meeting briefs across the broader client engagement team. Gui shared Dakota's pro tip for using Claude to dictate call notes in the lobby immediately after a meeting — eliminating the typing friction that has historically been the biggest barrier to capturing IP. Both agreed that AI is only as good as the data going in, and that picking one source of truth and training the team on it is now a strategic business decision, not a data decision. The conversation closed on leadership, trust, and culture. Dan's philosophy centers on understanding individual motivations, holding everyone accountable consistently, and trusting the team to do their jobs without micromanaging. In a difficult fundraising environment, maintaining team motivation comes from giving people the room to build durable, non-transactional relationships. Dan credited Crow Holdings' top-down culture as the reason he has never felt more like himself professionally — and the reason the team can apply institutional rigor to the wealth channel without losing the human element. 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 12, 202640 min

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.

May 5, 202649 min

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.

April 28, 202622 min

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.