Dakota Rainmaker Podcast

In this episode of the Rainmaker Podcast, Gui Costin sits down with Jonathan Kingery, Chief Distribution Officer at DoubleLine, for a wide-ranging conversation on building and leading high-performing distribution teams. Jonathan joined DoubleLine in 2025 and oversees the firm’s U.S. relationship management team across institutional, wealth management, sub-advisory, and retirement. Before that, he held senior roles at Franklin Templeton and Lord Abbett.

Jonathan traces his path from Dover, Delaware, where his father was his school principal through fourth grade, to a history degree at the University of Delaware and then to American Express Financial Advisors at age 22. Spending roughly seven years as a financial advisor gave him a lasting belief that everything starts with the client. At 30 he moved into asset management at Lord Abbett, where he later built the RIA team from a desk of one. He then went to Franklin Templeton, rising to head of U.S. wealth management with a team of about 270, before choosing a smaller, “SEAL Team 6” style team at DoubleLine.

The conversation turns to the fundamentals of sales leadership. Jonathan explains that a defined sales process turns habits into freedom, taking the thinking out of the day-to-day so salespeople can be creative in front of clients. He shares his “mission, team, individual” filter for decisions. He and Gui discuss the CRM as the “central nervous system” of a client business and how tools like voice notes and Claude make capturing call notes easier than ever. They agree that AI is only as good as the data beneath it, and that keeping data fresh, with advisor turnover of 20% to 25% a year, takes a dedicated team.

On leadership, Jonathan describes his approach: get the right talent in place first, then set the environment and the standards. He explains that the root of the word culture is care, and that “the lowest standard you’re willing to accept will define your culture.” A leader who ignores low effort pulls top performers down. Gui adds that kindness and high performance reinforce each other, and that the goal is to keep your best people forever.

Jonathan also shares practical advice for young professionals entering investment sales: write down your goals and your principles by hand, share the goals with someone, and revisit the principles each year as a living document and a North Star. He still keeps the list he wrote at age 29, and Gui ties this to Dakota’s own mantras.

Finally, Jonathan names prioritization as his biggest challenge, with his current focus on hiring for a new Tampa internal desk and open major-market territories. He doubled the distribution team in his first year, and both guests stress hiring deliberately. They close on self-awareness, scheduling time for thought leadership, and Stephen Covey’s advice to plan the week, not just the day. Gui calls the conversation “pure gold,” a to-do list for anyone who wants to run and lead a team.

In this episode of the Rainmaker Podcast, Gui Costin sits down with his longtime friend Lori McEvoy, a recently retired financial services executive who spent nearly a decade at Jennison Associates, retiring as managing director and global head of distribution. With more than 30 years in distribution, including leadership roles at Pilgrim Baxter, Fred Alger Management, WisdomTree Investments, and ClearBridge Investments, Lori shares the lessons she learned building and leading sales organizations and what she is doing next as she relaunches Investment Management Solutions.

Lori opens with her origin story. The fourth of five children in a big Irish Catholic family in Malvern, Pennsylvania, she grew up the daughter of a tile setter and a stay-at-home mom, in a family where no one had gone to college. After a year of working to save money, she enrolled at West Chester University, played Division I softball, and took a job at small-cap growth firm Pilgrim Baxter as its 13th employee. She stayed 16 years, rising from administrative assistant to equity partner and learning the business from the bottom up.

Turning to tactics, Lori and Gui discuss the importance of alignment with the boss. Lori recalls her boss telling her he did not like the question of an asset goal, because if you execute the tactics of the plan every day, AUM will follow. She describes servant leadership as her style and shares the four traits she hires for: passion for the craft, a team-first mindset, low ego with high EQ, and a commitment to continuous improvement. When she arrived at Jennison, the firm had no true distribution organization, so she built one focused on retaining institutional clients, cross-selling, and growing outside the US.

A major theme is the CRM. Lori calls it the backbone of the company and believes that if it is not in the CRM, it never happened. She explains how Jennison made Salesforce a firm-wide initiative, how she used its data to send a monthly Business Highlights report, and how Dakota Marketplace keeps information current compared with the outdated “green book” directories of years past. Gui encourages salespeople to think of themselves as “Inc.,” keep their CRM simple but organized, and use AI to dictate call notes straight into Salesforce.

Lori also offers advice for young salespeople: love what you do, become a student of the business, network through organizations like AIMSE, and emulate your leaders. She explains her philosophy of giving back in three buckets: mentorship, philanthropy, including her new seat on the AmeriCares board, and financial education. Through IMS, she hopes to help asset managers with distribution, talent assessment, and succession planning, much like a GM putting the right players on the field.

Gui closes by sharing his own 2011 realization that his mission for Dakota is to help other people get what they want out of life. The conversation ends on a theme of kindness, high standards, and a career that, as Lori says, “is not over.”

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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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.

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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.

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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.

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In this special edition of the Rainmaker Podcast, host Gui Costin sits down with Spencer Lovejoy, Co-Founder and CEO of the National Squash League (NSL), and BG Lemmon, co-owner of the Philadelphia Lightning, to unpack what it takes to build a modern sports league from the ground up, and why squash is uniquely positioned for a team-based reinvention.

The conversation opens with Spencer’s journey from junior squash in New Haven to competing professionally on the global circuit, and ultimately to co-founding the NSL alongside his partners. After years of playing an individual sport that often felt isolating, Spencer saw a clear gap in professional squash: the absence of teams, local identity, and a product that resonated with American sports fans. The NSL was designed to answer a simple but powerful question he was asked repeatedly as a pro: “What team do you play for?”

BG Lemmon brings a complementary perspective, blending his background in competitive collegiate squash with his career in finance and private investing. As a co-owner of the Philadelphia Lightning, BG discusses how his involvement grew organically, from persistent interest as a fan to hands-on participation in league operations. His experience reinforces a central theme of the episode: early-stage organizations require everyone to wear multiple hats, regardless of title.

A key focus of the discussion is how the NSL has intentionally broken from traditional squash formats. With six-player rosters, three-on-three matches, timed periods, substitutions, and power plays, the league prioritizes pace, strategy, and fan engagement. The power play, in particular, introduces a risk-reward dynamic that encourages aggressive, creative shot-making, something rarely seen in traditional professional squash.

Looking ahead, Spencer outlines the league’s near-term and long-term vision: measured expansion into new U.S. markets, a more robust match calendar, and continued emphasis on high-quality live events. Both Spencer and BG stress the importance of disciplined growth, proving the product, building the right partnerships, and earning credibility before scaling too quickly.

The episode closes with a discussion of the partnership between the NSL and Dakota, grounded in shared values around relationships, community, and bringing people together through sport. At its core, the conversation highlights how team culture, on the court and in business, can transform an individual pursuit into something much bigger.

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In this episode of The Rainmaker Podcast, Dakota Founder and CEO Gui Costin sits down with Adam Rosen, founder of an email marketing agency that helps startups, unicorns, and large enterprises generate sales through cold email. The conversation offers a practical, experience-driven look at how cold outreach has evolved, and why it remains one of the most effective tools in modern sales when executed correctly.

Adam begins by walking through his entrepreneurial origin story, from studying sport management in college to discovering entrepreneurship late in his academic career. That pivot led to his first startup, a college recruiting platform that worked with major global brands. Despite making early mistakes, Adam credits cold email as the single most important driver behind acquiring customers, raising capital, and ultimately exiting the business—experience that later became the foundation for his current company.

A major theme of the episode is how dramatically the cold email landscape has changed since the mid-2010s. Adam explains that tactics that once worked, such as sending high volumes of emails from a primary domain, are now actively harmful. Today, success starts with infrastructure: properly set up sending domains, inbox warming, and protecting domain reputation. Without that foundation, even strong copy and targeting won’t matter because emails won’t reach the inbox.

The discussion then shifts to measurement and optimization. Adam cautions against tracking open rates in cold email, noting both deliverability risks and unreliable data. Instead, he emphasizes reply rates as the most meaningful signal of success, since a reply confirms both inbox placement and message resonance. Sudden drops in reply rates, he explains, are often an early warning sign of deliverability issues.

Beyond tactics, the episode dives into the psychology of cold outreach. Adam and Gui agree that the biggest barrier to success isn’t technology, it’s mindset. Cold email doesn’t feed the ego and requires resilience in the face of rejection. Adam frames email as nothing more than a tool to connect party A with party B, arguing that professionals who can stomach direct feedback and rejection will consistently outperform those who avoid it.

The episode closes with actionable guidance on email construction, from concise, relevant subject lines to short, direct body copy that clearly states purpose, value, proof, and a call to action. The takeaway is clear: when paired with the right infrastructure and mindset, cold email remains one of the most scalable and reliable ways to build pipelines.

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In this episode of the Rainmaker Podcast, Gui Costin sits down with Larry Pokora, Managing Director on the Investor Relations team at Tilden Park Capital, to unpack a 30+ year career spanning traditional asset management, alternatives, and institutional fundraising. The conversation moves from Pokora’s blue-collar upbringing in Pittsburgh to his hard-earned perspective on what actually drives long-term success in fundraising.

Pokora begins by tracing his career back to an unconventional starting point: working as a programmer analyst at Mellon Financial Services after attending the Community College of Allegheny County. That early technical role, he explains, trained him to think linearly, diagnose problems, and stay disciplined when things didn’t work the first time. Those habits—problem-solving, persistence, and accountability, became foundational as he transitioned into product specialist and sales roles within Mellon.

A pivotal chapter followed at SEI Investments, where Pokora gained broad exposure to how asset managers, consultants, and investment teams operate. His time at SEI provided a full view of the institutional ecosystem, from OCIO mandates to consulting dynamics, while reinforcing the importance of preparation and repetition in winning mandates. Despite success, Pokora recognized a gap in his experience: he wanted to work closer to firms actually managing capital.

That realization led him to Brandywine Asset Management and later to what he describes as a career-defining move, joining Paulson & Company in 2006, just ahead of the Global Financial Crisis. Fundraising during this period required more than performance figures; it demanded the ability to clearly explain complex strategies to consultants and allocators navigating fear, skepticism, and unfamiliar instruments. Pokora emphasizes that sales at this level is ultimately about education and translation, not persuasion.

Throughout the conversation, Pokora outlines a clear fundraising philosophy. First, knowledge is non-negotiable, knowing your product, understanding portfolio fit, and being fluent in competitors’ strategies. Second, there are no shortcuts. Even decades into his career, Pokora still prioritizes volume, preparation, and follow-through. Third, disciplined CRM usage is a competitive advantage, enabling better client engagement, internal reporting, and accountability.

Beyond tactics, Pokora highlights the less discussed but equally important role of energy and leadership. Investor relations professionals set the tone within an organization, particularly during challenging periods. Showing up prepared, optimistic, and transparent builds trust internally and externally.

The episode closes with practical advice on internal communication, executive interaction, and final presentations, reinforcing a recurring theme: success in fundraising is built through consistency, clarity, and doing the work, day after day, cycle after cycle.

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