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Management · Dakota Team

Dakota Rainmaker Podcast

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

Showing 20 · updated from the feed

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 fundraisin

Jul 7
39 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

May 19
35 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 legen

May 12
40 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

May 5
49 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 acros

Apr 28
22 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 institu

Apr 21
39 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

Apr 14
35 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 conve

Mar 17
44 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,

Mar 3
22 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

Feb 17
51 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, c

Feb 10
19 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,

Feb 3
32 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+

Jan 27
35 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

Jan 20
34 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 th

Jan 13
38 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 a

Dec 16 2025
34 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 comprehensiv

Dec 9 2025
31 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 emer

Dec 2 2025
27 min

Ryan Williams on Mastering Sales with a Lean Team and a Personal Touch at Swan Global Investments

In this episode of the Rainmaker Podcast, Gui Costin sits down with Ryan Williams, Director of National Accounts at Swan Global Investments, to explore what makes a lean,

Nov 18 2025
26 min

Leading with Transparency and Bazooka Content: Manish Khatta on Scaling Potomac

In this episode of the Rainmaker Podcast, Gui Costin sits down with Manish Khatta, CEO and CIO of Potomac, for a candid and insightful conversation about building and sca

Nov 11 2025
35 min

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