If It's Not in Salesforce, It Didn't Happen: Michael O'Shea on Sales Discipline at Origin Investments

In this episode of the Rainmaker Podcast, Gui Costin sits down with Michael O'Shea, Director and Head of Private Wealth Solutions at Origin Investments, for a wide-ranging conversation about systems, discipline, and what it actually takes to build a durable capital-raising career. Michael's path into the business started almost by accident nearly two decades ago, when curiosity about what a REIT and a Series 7 actually were pulled him into calling on advisors and raising capital for niche, tax-advantaged real estate deals. That early curiosity turned into a genuine passion for investing, which he later formalized by going back to school for an MBA in real estate finance and earning his CFA charter, a credential he says fundamentally sharpened how he talks about markets and builds trust with advisors. Michael shares the origin story behind Origin Investments itself: a Chicago-based real estate manager founded by two former Mercantile Exchange traders, Michael Episcope and David Scherer, who built significant personal wealth trading before computers pushed traders out of the pits. Rather than keep taking on trading risk, they built Origin to invest more transparently and with better alignment than what they'd experienced themselves as investors. Nineteen years later, the firm manages $5 billion in assets, supports more than 5,000 investment partners, and now partners with 165 RIAs, all distributed through a lean, fully RIA-and-family-office-focused team of five reps plus Michael and a sales enablement associate. A major thread of the conversation is Michael's belief that systems, not goals, drive consistent fundraising results. He leans on an Olympics analogy: the goal is gold, but it's the underlying training system that actually gets an athlete there. Applied to sales, that means knowing exactly who you're calling on, mastering your product, and building weekly, monthly, and quarterly cadences with real process improvement baked in. That same discipline extends to pipeline management. Michael reviews his team's pipeline every week specifically to catch staleness or inflated deal sizes, a philosophy Gui strongly echoes: the best salespeople who raise the most money are the ones who keep the tightest, most accurate pipelines, especially when no one else is watching. The two also dig into how technology has changed the day-to-day of fundraising. Michael describes Salesforce as his daily "cockpit," now supercharged by AI tools that transcribe calls and voice memos directly into call notes and tasks, removing much of the friction and dread that used to come with logging activity. Gui ties this back to his own hard rule at Dakota: if it's not in Salesforce, it didn't happen, because that documentation is exactly what a sales rep's salary is paying for. On leadership, Michael describes himself as a coach who removes roadblocks and filters out noise for his team, while holding a firm, non-negotiable line on entering call notes. His advice to young fundraisers centers on continuous self-investment, learning AI tools, coding, and new skills, so they're preparing not just to be a great analyst, but eventually a great CEO. He closes by naming his current challenge: a capital markets backdrop where the 10-year Treasury and cap rates aren't behaving as expected, making long-term, illiquid asset classes like real estate a harder sell in the near term. *Disclaimer: All Origin Investments statistics referenced herein — including assets under management, investor count, RIA partner relationships, and any projections, targets, or track-record figures — are as of September 1, 2026, are derived from Origin's internal records, and are unaudited. These figures are subject to change and are not indicative of future results.*