Dakota Rainmaker Podcast

Dakota Team

The "Dakota Rainmaker Podcast," hosted by Gui Costin, CEO of Dakota, offers a unique look into sales strategies from top industry executives. Each episode explores the inner workings of successful sales organizations, from philosophy to execution. This podcast is essential for sales professionals seeking wisdom from the best in the field.

Play

Open in

22 episodes
Avg 35 min
English

Episodes 22

Newest Oldest Longest

All20 Unplayed20 In progress0 Played0

Counted on this page — what you have heard stays on this device, so it is not something the list can be paged by.

Tuesday · 47 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 · 31 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.
S5 · E1
July 7 · 39 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 · 35 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 · 40 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 · 49 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 · 22 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.
April 21 · 39 min
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.
April 14 · 35 min
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.
March 17 · 44 min
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.
March 3 · 22 min
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.
February 17 · 51 min
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.
February 10 · 19 min
The National Squash League: Reinventing Pro Squash
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. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.
February 3 · 32 min
How Cold Email Really Works Today with Adam Rosen
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. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.
January 27 · 35 min
Why Discipline Matters in Fundraising With Larry Pokora of Tilden Park Capital
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. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.
January 20 · 34 min
From Operator to Investor: How Nate DaPore Built Roo Capital Around Talent and Execution
In this episode of the Rainmaker Podcast, Gui Costin sits down with Nate DaPore, Founder of Roo Capital, to explore how an operator’s mindset, disciplined sales execution, and hands-on value creation have shaped a differentiated venture capital platform. DaPore’s story begins with early exposure to sales and entrepreneurship out of necessity. Paying his own way through college, he convinced a car dealership to give him a trial selling cars over the summer, quickly outperforming expectations and earning enough to fund his education. That formative experience reinforced two core themes that would define his career: accountability and relationship-driven selling. Following college, DaPore co-founded Benefitfocus, a healthcare software company that digitized employee benefits enrollment at a time when paper processes dominated. Starting as the firm’s first salesperson and eventually leading a 200-person sales organization, he helped scale the business from zero to $200 million in recurring revenue and through an IPO. The experience gave him firsthand exposure to scaling teams, building go-to-market engines, and operating through rapid growth. DaPore later founded and served as CEO of PeopleMatter, a venture-backed SaaS company focused on talent management for hourly workers. While the company was ultimately successful, raising over $60 million in venture capital and exiting to a strategic buyer, the experience revealed critical shortcomings in traditional venture models. As a founder, DaPore observed that many investors were capital providers first and operational partners second, often lacking the infrastructure or incentives to meaningfully support execution. Those lessons became the foundation for Roo Capital. DaPore built the firm around a three-part model—capital, talent, and growth, designed to actively support founders beyond the check. Roo integrates an in-house executive search business and a dedicated growth team that works directly with portfolio companies on hiring, go-to-market strategy, pricing, and systems. This structure allows Roo to participate deeply in value creation rather than relying on passive oversight. A recurring theme in the conversation is DaPore’s emphasis on transparency and relationship-building, particularly with LPs. Roo replaces traditional static quarterly reports with interactive video-based portfolio updates, featuring founders directly and allowing real-time Q&A. This approach not only strengthens trust but also gives LPs a clearer understanding of how value is being created between annual meetings. On the investment side, DaPore outlines Roo’s disciplined early-stage framework, centered on the “6 Ps”: People, Passion, Pain, Possibility, Priorities, and Product. The firm prioritizes founder quality and problem relevance, investing primarily at the pre-seed, seed, and early Series A stages across cybersecurity, healthcare, and vertical SaaS. The episode closes with practical insights on fundraising as a sales process. DaPore emphasizes repetition, iteration, and feedback, using early LP meetings as pressure tests to refine messaging and sharpen differentiation. By treating fundraising like enterprise sales, Roo was able to exceed its first fund target and build momentum for future growth. Overall, the conversation highlights how operator empathy, disciplined sales execution, and hands-on engagement can translate into a differentiated and durable investment platform. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.
January 13 · 38 min
Andrew Fentress on Building a Risk-First Private Credit Platform
In this episode of The Rainmaker Podcast, Gui Costin sits down with Andrew Fentress, Co-Founder of ACRES Capital, to discuss his career path, the formative experiences that shaped his leadership style, and the lessons he carries forward from multiple market cycles. The conversation blends personal background with practical insights on sales, investing, and long-term platform building. Fentress begins by tracing his early life in the Washington, D.C. area, where he grew up surrounded by competition, entrepreneurship, and professional athletics. Exposure to business builders and elite performers at a young age instilled an appreciation for discipline, preparation, and accountability, themes that recur throughout his career. That competitive mindset was reinforced at Boston College, where he spent four years on the varsity sailing team, learning how consistent effort and teamwork translate into performance under pressure. After college, Fentress entered the workforce through a direct sales role outside of financial services, gaining early, hands-on experience with prospecting, persistence, and client engagement. Recognizing the need for stronger technical and financial grounding, he later pursued an MBA at UNC’s Kenan-Flagler School of Business. Graduate school proved to be a critical inflection point, equipping him with the analytical tools and language necessary to operate effectively in institutional markets. His entry into Wall Street came through opportunistic networking rather than a traditional recruiting path. A last-minute opening in Morgan Stanley’s summer analyst program provided the gateway into institutional finance, where he went on to build foundational skills in communication, risk-taking, and navigating complex organizations. Fentress describes the trading environment as a daily test of judgment and accountability, where feedback is immediate and credibility matters. In the mid-2000s, Fentress transitioned into private credit, helping to build a platform at a time when the strategy was still relatively nascent. That experience, combined with living through the Global Financial Crisis, shaped his long-term perspective on risk. He emphasizes that credit investing is ultimately defined by losses avoided, not just returns generated, a lesson that continues to inform his approach today Those lessons became central when Fentress co-founded ACRES Capital. He explains that the firm was built with a risk-first mindset, emphasizing discipline, downside analysis, and alignment across the platform. Rather than optimizing for short-term market conditions, ACRES was designed to endure volatility and perform across cycles. Throughout the episode, Fentress also highlights the importance of staying close to clients and assets. Being on the road, meeting investors, and seeing markets firsthand is not just relationship-building, it’s a critical learning tool. For him, real insight comes from continuous exposure to people, properties, and conditions on the ground. The conversation ultimately underscores a consistent message: durable success in investing and sales comes from preparation, humility, and respect for risk. Cycles change, markets evolve, but discipline and curiosity remain enduring advantages. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.
Dec 16, 2025 · 34 min
Building Trust at Scale: Brian Willer on Leading High-Performing Institutional Sales Teams
In this episode of the Rainmaker Podcast, Gui Costin sits down with Brian Willer, Senior Vice President and National Sales Manager of Institutional Business Development at Federated Hermes, to discuss leadership, communication, and the operational discipline required to scale an institutional sales organization. Willer begins by reflecting on his early background growing up in Maine with no direct exposure to investment management. His interest in financial markets was sparked by curiosity rather than formal guidance, eventually leading him to Bryant University, where a trading simulation room cemented his desire to enter the industry. He launched his career at Fidelity Investments on the inside sales desk, gaining foundational training during the Global Financial Crisis. This period proved formative, teaching him how to navigate difficult market environments, client uncertainty, and the importance of preparation and resilience. After several years at Fidelity, Willer sought a path that allowed him to move into the field without leaving New England. Following a stint in recordkeeping sales, he joined Federated Hermes in 2013, entering the institutional business during a period of growth. Over time, he progressed into a leadership role overseeing an eight-person institutional sales team across North America, while working closely with the firm’s liquidity, treasury, and consulting relations groups. A central theme of the conversation is culture and communication. Willer emphasizes that Federated Hermes’ culture is built on trust, transparency, and long-term tenure, supported by a relatively flat organizational structure. He believes leaders must stay deeply connected to their teams, noting that sales leadership cannot be effective from a distance. His communication model blends structure and consistency—biweekly team meetings, monthly one-on-ones, and formal quarterly reviews—with constant daily interaction to stay close to opportunities, challenges, and client conversations. Willer also highlights the importance of tapping into collective intelligence. He encourages open sharing across the team, allowing reps to learn from one another’s positioning strategies, client objections, and successful approaches. By deliberately creating forums where ideas and insights are exchanged, he helps eliminate silos and raise the performance of the entire group. This philosophy extends beyond sales to cross-functional collaboration with product, marketing, and RFP teams. The discussion also covers the role of CRM systems, particularly Salesforce, as a core business tool rather than an administrative burden. Willer stresses the importance of data quality, capturing meetings early, and documenting detailed notes to support long institutional sales cycles. A well-maintained CRM enables better internal coordination, more relevant client outreach, and improved prioritization across teams. When asked about leadership philosophy, Willer describes his approach as trust-based and intentional. He prioritizes kindness, thoughtful communication, and honest feedback delivered in the right setting. For young professionals entering the industry, his advice centers on building relationships early and focusing on controllable factors such as preparation, process, and continuous learning. He concludes by noting that time management is his greatest challenge as a leader, and that prioritizing what best serves clients and the team is the framework he uses to stay focused and effective. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.
Dec 9, 2025 · 31 min
Mark Tower on Consistency, Connection, and Leading with Purpose in Institutional Sales
In this episode of the Rainmaker Podcast, featuring Mark Tower, Senior Institutional Sales and Marketing Professional at Asset Management One USA, delivers a comprehensive masterclass in relationship-driven sales strategy, leadership, and career longevity within the asset management industry. With 25 years of experience, Tower offers a mix of practical advice and personal anecdotes that emphasize the importance of consistency, adaptability, and authenticity in building a successful sales career. Tower shares his background growing up as the youngest of eight children in New Jersey, an experience that helped him develop strong interpersonal communication skills. After initially exploring a career in radio while studying at Boston College, he pivoted to finance after a pivotal career fair encounter led to an internship at Orbitex. This early exposure to asset management sales shaped his view of the business as deeply relational rather than purely transactional. Throughout his career, from retail wholesaling to institutional alternatives, Tower has maintained a wholesaler’s mentality, centered on volume, persistence, and regular in-person meetings. He stresses that while the sales process has evolved, particularly in the post-COVID world, the fundamentals remain the same: show up, follow through, and build trust over time. Tower describes structuring his travel plans like a “milk route,” ensuring consistent visibility with clients, which builds credibility even when meetings aren’t immediately productive. At Asset Management One, Tower leads a small business development team but operates within a global firm backed by Mizuho Bank and Dai-Ichi Life. He explains how even with a lean U.S. team, global coordination is key, and everyone, from operations to compliance, is considered part of the broader sales function. Internal communication is facilitated through Microsoft Teams, allowing seamless collaboration across time zones and remote work environments. Tower emphasizes the critical role of technology, particularly CRMs, in organizing and scaling a salesperson’s efforts. He’s a strong advocate for Salesforce, especially when integrated with tools like Dakota Marketplace, which he credits for increasing efficiency and effectiveness in prospecting and follow-ups. He believes that proper CRM usage not only supports personal productivity but also improves firm-wide communication and accountability. Leadership-wise, Tower positions himself as a “player-coach,” actively supporting his team without micromanaging. He highlights the importance of empathy, advocacy, and leading by example, whether through hands-on involvement in RFPs or making time for late-night coordination with global colleagues. For aspiring sales professionals, Tower’s advice is simple but powerful: be present, be authentic, and be helpful. He encourages young professionals to prioritize face-to-face engagement, attend conferences, and resist the temptation to overly rely on digital outreach. In an era where emails and automation dominate, Tower argues that true relationship-building still requires showing up and offering genuine value. Overall, this episode delivers valuable insights into what it takes to build and maintain a successful institutional sales career in asset management. Tower’s experience-driven wisdom and grounded leadership philosophy offer lessons not just for sales professionals, but for anyone navigating a relationship-intensive industry. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.
Dec 2, 2025 · 27 min
Karl Engelmann on Building Sarmaya, Selling with Conviction, and Leading Through Relationships
In this episode of the Rainmaker Podcast, host Gui Costin welcomes Karl Engelmann, co-founder and COO of Sarmaya Partners, to share the story behind the firm’s rapid emergence and his philosophy on sales, leadership, and entrepreneurship. With over three decades of experience in financial services, Karl offers listeners a rare, behind-the-scenes look into launching an asset management firm and the strategic thinking driving its success. Karl begins by tracing his unconventional career path, from aspiring journalist to accomplished sales leader. His communication skills and passion for storytelling laid the foundation for a career that spanned roles at Angel Oak Capital, Cambiar Investors, and AIM/INVESCO. These experiences culminated in the co-founding of Sarmaya Partners, where Karl saw the opportunity to build a firm aligned with his vision and values. The conversation dives deep into Sarmaya’s unique investment strategy, which centers around a thematic belief in a new commodity super cycle. Rather than chase overcrowded markets, Karl and his partner Wasif identified a return to tangible assets like gold, silver, and copper as the next long-term trend. After initially structuring the firm as an LP, they pivoted to launching an actively managed ETF in January 2024 to better serve a broader investor base. Karl shares Sarmaya’s go-to-market strategy and how they’ve grown from two founders to a six-person team, carefully hiring seasoned professionals with deep industry relationships. He emphasizes the power of focus, targeting RIAs, family offices, and mid-sized broker-dealers—segments often overlooked by larger firms but open to differentiated strategies. A major theme throughout is the importance of relationships over transactions, and Karl’s approach is deeply rooted in decades of trust and credibility built across the industry. Sales process and infrastructure also play a key role in the discussion. Karl highlights the importance of having a clean, well-maintained CRM as the central nervous system of the firm’s sales efforts. Partnering with Dakota has helped Sarmaya stay agile and organized in an environment where client rosters and firm dynamics are constantly shifting. The episode also explores Karl’s leadership style, which blends high accountability with trust and autonomy. He believes in empowering experienced salespeople to execute without micromanagement, while maintaining clarity through communication and shared goals. His mantra—"take the bit out of the mouth and let them run"—underscores his belief in hiring the right people and giving them room to perform. As the episode closes, Karl speaks candidly about the biggest challenge facing Sarmaya: growing assets under management. Yet his energy is unwavering. With a strong product, clear strategy, and relentless optimism, Karl’s approach to sales and leadership provides an inspiring blueprint for anyone building a firm from the ground up. This episode is a masterclass in execution, resilience, and the long game of relationship-driven sales. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

Showing 1–20 of 22 episodes