Episode summary
If It's Not in Salesforce, It Didn't Happen Michael O'Shea on Sales Discipline at Origin Investments
Dakota Rainmaker Podcast
· · 33 min · Hosts: Gui Costin · Guests: Michael O'Shea
Summary
Michael O'Shea argues that durable capital raising is built on systems, not vague ambition. He says his path into the business started almost by accident, but once he got into niche real estate fundraising he invested in himself with an MBA in real estate finance and the CFA charter, which he says improved how he talks about markets and wins trust.
He describes Origin Investments as a Chicago firm founded by former Mercantile Exchange traders Michael Episcope and David Scherer, who wanted more transparency, alignment, and lower fees than they had seen as investors. O'Shea says Origin now has about $5 billion in assets, over 5,000 investment partners, and 165 RIAs, supported by a lean five-person distribution team plus a sales enablement associate.
The conversation focuses on his operating philosophy: tight CRM discipline, weekly pipeline reviews, clear priorities, and constant process improvement. He says, "If it's not in Salesforce, it didn't happen," because the CRM is the cockpit that lets the team track tasks, follow-ups, and stale opportunities. He also emphasizes direct leadership, high standards, and ongoing training for a niche business that requires both tax knowledge and sales precision.
Key takeaways
- O'Shea says Origin runs a five-person distribution team focused entirely on RIAs and family offices, not broker-dealers.
- He argues that sales success comes from systems and repeatable cadences, not from chasing arbitrary goals.
- He says the CRM is mandatory: "If it's not in Salesforce, it didn't happen."
- O'Shea believes stale pipeline entries hurt performance, so every opportunity must be reviewed and updated weekly.
- He advises young capital raisers to keep investing in themselves and learn adjacent skills like Python, AI, and workflows.
Notable quotes
“It was really like, you know, what is a REIT? What is a Series 7? That seems like an interesting thing to sort of pursue about 18 years ago”
“If it's not in Salesforce, it didn't happen”
“I look at it as like the cockpit that we're in every single day”
“the 10-year Treasury”
How the episode opens
Origin data, as of September 1st, 2026. Source: Origin Investments internal records, unaudited, subject to change.
Welcome to the Rainmaker podcast with your host, Gee Costin. The goal of this podcast is to give listeners a unique look into sales strategies from top industry executives. We introduce you to the heads of sales and heads of distribution who will help you understand the inner workings of the successful sales organizations from philosophy to execution.
This podcast is essential for sales professionals seeking wisdom from the best in the field. If you're not familiar with Dakota and their Dakota Rainmaker content, please check out dakota.com to learn more about their services.
This episode is brought to you by Dakota Marketplace. Are you tired of constantly jumping between multiple databases and channels to find the right investment opportunities? Introducing Dakota Marketplace, the comprehensive institutional and intermediary database built by fundraisers for fundraisers.
With Dakota Marketplace, you'll have access to all channels and asset classes in one place, saving you time and streamlining your fundraising process. Say goodbye to the frustration of searching through multiple databases, websites, Form ADV's, and say hello to a seamless and efficient fundraising experience. Sign up now and see the difference Dakota Marketplace can make for you.
Visit dakota.com/dakota-marketplace today. What is up everybody? It's Gee Costin, founder and CEO of Dakota.
Welcome to another episode of the Rainmaker podcast. I'm so excited to be joined by Michael O'Shay from Origin Investments. Michael, welcome.
Hey Gee, thanks for having me. — Oh, so thrilled to have you. As director and head of private wealth solutions, Michael leads Origin's capital raising initiatives, oversees sales strategy, and develops strategic partnerships with registered investment advisors to expand Origins investment platform. Previously, Michael served as head of Origin Exchange, Origins 1031 Exchange platform.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- sales discipline
- pipeline management
- capital raising systems
- salesforce ai automation
- real estate investing
Companies and tickers mentioned
- CRM
- Origin Investments
- Salesforce
Watch the episode
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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Dakota Rainmaker Podcast, this episode and its artwork belong to Dakota Team. Octagon is not affiliated with the show; this page is an independent summary.
