Raising Private Money with Jay Conner

Achieving Sustainable Success Through Team Building and Systemization with Josh Thomas

Jay Conner

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In the modern entrepreneurial world, “working harder” is often worn as a badge of honor. But if you’re trapped in a never-ending cycle of doing everything yourself, even in a highly profitable business, you’re likely feeling the stress and missing out on the freedom you thought entrepreneurship would provide. The recent episode of “Raising Private Money” with Jay Conner and Josh Thomas, founder of VAIQ and host of the “Leverage Everything” podcast, unpacks why doing less (the right way) is not only desirable but essential for growth and happiness.

The Real Bottleneck: It’s Not Money or Deals

For many real estate investors and entrepreneurs, the supposed bottleneck is usually either finding deals or raising money. But as Jay and Josh illuminated, the real limiting factor is often the refusal to build the right team and implement effective systems. Both speakers share candid personal experiences from their early days—Jay recalling nights when the stress bled into family life, and Josh reflecting on patterns he’s seen with thousands of entrepreneurs in over 30 industries.

This stubborn “lone wolf” approach inevitably extracts a toll: time, mental energy, relationships, and ultimately, money. What’s harder to spot than monetary losses are the hidden costs of stress, lost opportunities, and burnout. As the episode makes clear, sole operators eventually hit the ceiling—where the only path forward is to learn how to leverage time, talent, and systems.

The Mindset Shift: Delegate and Disappear

For Jay, a pivotal “wake-up call” came after realizing financial success wasn’t fulfilling when it came paired with overwhelm. His commitment thereafter: dictate, delegate, and gradually step away from daily operations. This philosophy doesn’t mean abandoning the business or lowering standards; it’s about smartly putting people and systems in place so that the business serves you, rather than the other way around.

Josh brings two decades of practical experience to the discussion, warning against the mirage that hiring alone solves all problems. He explains the critical need for foundational systems and clarity on desired outcomes—before seeking to delegate tasks. Without that clarity, bringing on help (remote or otherwise) only risks amplifying inefficiency. Entrepreneurs must first document and refine processes so new hires become force multipliers, not added headaches.

The Four-Box Framework for Trustworthy Business Relationships

Beyond operational efficiency, the episode also covers Josh’s insightful framework for assessing business relationships—a model directly applicable for those seeking or offering private money, but also valuable for leaders overseeing teams, partnerships, or even personal interactions. Josh outlines four sequential “boxes” that must be checked for a healthy, productive engagement:

  1. Integrity: Is the person trustworthy? All other considerations are irrelevant without this foundational element.
  2. Competence: Do they know what they’re doing? No matter how much you like or trust someone, if they lack skill, the partnership is doomed.
  3. Stewardship: Will they be responsible caretakers of your resources, whether that’s money, time, or energy?
  4. Deal Details: Only after the first three are in place do the specifics of the opportunity or relationship truly matter.

This model flips the common pitch-centric approach. True leverage—whether with employees, partners, or lenders—flows from trust and capability, never just numbers.

Pulse: Bringing High Performance to Virtual Teams

Josh also expands on “Pulse,” his process-driven system modeled after elite athletes. Like Tiger Woods or Michael Jordan, top performers rely not on raw hustle, but consistency, constant measurement, coaching, skill refinement, and relentless execution. By instilling these traits into remote teams (especially with affordable int