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Dakota Rainmaker Podcast: Daily Summaries Delivered
by 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.
Latest Episodes
The most recent episodes — sign up to get AI-powered summaries of each one.
- 3 weeks ago39 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 th...
- May 19, 202635 min
Dan Amir: Inside Crow Holdings' Wealth Distribution Playbook
In this episode of The Rainmaker Podcast, Gui Costin sits down with Dan Amir, Managing Director of Investor Coverage at Crow Holdings, for a wide-ranging conversation on building a wealth distribution team, applying institutional rigor to the wealth channel, and leading a sales organization through a difficult fundraising environment. Dan grew up in New Jersey, spent the first 13 years of his career in New York at BNY Mellon and Morgan Stanley in relationship and distribution roles, and made ...
- May 12, 202640 min
Dominica Ribeiro: Marketing and Distribution Under One Roof
In this episode of The Rainmaker Podcast, Gui Costin sits down with Dominica Ribeiro, Chief Marketing and Distribution Officer at Breckinridge Capital Advisors, the legendary asset manager based in Boston. The conversation covers Dominica's non-traditional career path, the structure and discipline of Breckinridge's distribution team, and the leadership philosophy that has shaped how she runs sales and marketing as a single integrated function. Dominica started full-time in the industry direct...
- May 5, 202649 min
Keith VanOrden on Building TCW's Retail Distribution Platform from Scratch
In this episode of The Rainmaker Podcast, Gui Costin sits down with Keith VanOrden, Head of Retail Distribution for North America at TCW. Keith brings nearly 30 years of experience building and leading sales teams, including more than 13 years at BlackRock, most recently as the national sales manager for iShares, and earlier roles at Delaware Investments, Fidelity, and Putnam, where he started his career in Boston. The conversation opens with Keith's origin story growing up in Philadelphia, a...
- Apr 28, 202622 min
Stephen Tiller on Leadership, AI, and Picking Up the Phone
In this episode of The Rainmaker Podcast, Gui Costin sits down with Stephen Tiller, who joined Sterling Global Financial roughly 13 years ago after a 35-year career across some of the most respected names in real estate finance and investment banking. Sterling, founded by David Kosoy more than 50 years ago, manages roughly $7–8 billion in assets across six countries and runs a platform that includes private credit lending funds, development and construction businesses, trust companies, and ba...
- Apr 21, 202639 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 esote...
- Apr 14, 202635 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 ...
- Mar 17, 202644 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 sid...
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About Dakota Rainmaker Podcast
The "Dakota Rainmaker Podcast," hosted by Gui Costin, CEO of Dakota, offers a unique look into sales strategies from top industry executives. Each episode explores the inner workings of successful sales organizations, from philosophy to execution. This podcast is essential for sales professionals seeking wisdom from the best in the field.
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Frequently Asked Questions
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Dakota Rainmaker Podcast covers topics including Business, Management. Our AI identifies the specific themes in each episode and highlights what matters most to you.
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