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:
- Integrity: Is the person trustworthy? All other considerations are irrelevant without this foundational element.
- 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.
- Stewardship: Will they be responsible caretakers of your resources, whether that’s money, time, or energy?
- 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 international talent), businesses can shed busywork, reclaim strategic focus, and scale seamlessly.
Key Takeaways: Build Freedom by Leveraging Others
Jay and Josh’s dialogue delivers a powerful reminder: lasting freedom and business growth aren’t products of heroic solo efforts but rather of deliberate leveraging—of people, processes, and principles. Whether you’re bottlenecked by your own busyness or afraid to leap into delegation, remember: you’ll never “find” the time to scale. You have to make it—by letting go and tapping into the strengths of others.
This episode is a must-listen for anyone ready to stop only surviving and start truly living their entrepreneurial vision.
10 Discussion Questions from this Episode:
- Jay Conner and Josh Thomas both emphasize the importance of building a strong team for scaling a business. What are some barriers that prevent entrepreneurs from delegating tasks or hiring help, and how can they overcome these obstacles?
- According to Josh Thomas, doing everything yourself in a business doesn’t just cost money but can also impact time, emotional well-being, and relationships. What personal experiences resonate with this idea, and how have you managed these non-monetary costs?
- Josh Thomas outlines common mistakes entrepreneurs make when hiring remote talent. What systems or strategies have you found most effective for onboarding and managing remote employees?
- The episode highlights the principle that you are only earning at the level of the tasks you perform. How can business owners identify which tasks to delegate, and what resources can help them make these decisions confidently?
- Josh Thomas describes four “boxes” a private lender checks before investing: integrity, competence, stewardship, and deal details. How can real estate investors demonstrate these qualities to potential lenders?
- When discussing the timing of hiring, Jay Conner and Josh Thomas push back against the idea of waiting until you’re “ready.” What risks are involved in hiring before you feel fully prepared, and how can these risks be mitigated?
- The Pulse system (Process, Updates, Leadership, Skills, Execution) is central to Josh Thomas’s approach to building high-performance teams. Which of these elements do you think is most challenging to develop, and why?
- Throughout the episode, both speakers mention the value of having a business coach or mentor. In what ways have coaching or mentorship benefited your professional growth, and how would you recommend others find the right coach?
- Applying the “four boxes” concept to personal and professional relationships beyond business, how can these foundational values improve trust and collaboration in teamwork?
- Josh Thomas shares about leveraging international virtual assistants through his company, VAIQ. What are your perceptions or experiences with hiring internationally, and what are some advantages or challenges you foresee in this model?
Fun facts that were revealed in the episode:
- Josh Thomas has been a guest or host on over 1,200 podcast episodes and currently hosts the podcast “Leverage Everything,” which boasts over 400 episodes.
- The Pulse system, developed by Josh Thomas, is inspired by the traits and habits of elite athletes like Tiger Woods and Michael Jordan, focusing on process, updates, leadership, skills, and execution to optimize team performance.
- Jay Conner once had a wake-up moment about business and life balance when he found his wife, Carol Joy, overwhelmed with checkbooks and bills at 10 pm, which led him to rethink his approach and commit to automation and delegation in his real estate business.
Timestamps:
00:00 Building a Real Estate Team
05:00 The pressures of entrepreneurship
08:07 Committing to business automation
10:12 Hiring and delegation strategies
15:19 Taking risks for success
19:56 The lender’s checklist for loans
23:13 Importance of competence in deals
24:48 Ensuring investor money is handled well
30:02 Hiring international employees for success
30:57 Hiring and integrating international talent
36:01 Connect with Josh Thomas:
35:29 Hiring advice and book offer
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