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

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 [https://www.dakota.com/calendar-website] to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

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 [https://www.dakota.com/calendar-website] to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

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 [https://www.dakota.com/calendar-website] to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

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 [https://www.dakota.com/calendar-website] to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.

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 [https://www.dakota.com/calendar-website] to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.