Why Businesses Fail #11 - Unlocking Startup Success: Building Strong Teams, Overcoming Entrepreneurial Challenges, and Thriving in the New Business Era

Weekly Show Summary

This week, our show brings together expert guests and actionable advice to answer the million-dollar question: “What does it really take to succeed as a modern entrepreneur?” From founder fallouts and team building, to navigating common startup pitfalls and finding your unique voice, each segment packs plenty of practical solutions (and a healthy dose of reality) for founders old and new. Get the inside scoop on transforming setbacks into setup for success, mastering the psychology of entrepreneurship, and harnessing today’s digital tools to look—and be—your most professional self. Whether you’re a first-time founder or seeking a business reboot, you’ll find wisdom, wit, and real-world steps to help your venture thrive.

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Episode Summaries & Key Takeaways

Episode 1: S12 E49 Janis Michala 1 Audio with Jeremy Gray

Janice Michala, seasoned startup pro, joins Jeremy Gray to tackle a foundational reason startups fail—having the wrong team—and offers people-first solutions for building lasting, impactful businesses.

Key Takeaways: 

  • Choose co-founders wisely: Deeply examine values, commitments, and expectations—friendship alone isn’t a recipe for startup harmony.

  • Prepare for the real conversations: Discuss risk, time commitment, family involvement, and what happens when things go wrong.

  • Understand control vs. ownership: Holding more shares doesn’t guarantee leadership—focus on trust, clear roles, and living up to your word.

Episode 2: S12 E50 Janis Michala 2 Audio with Jeremy Gray

Jeremy and Janice continue their candid conversation on founder dynamics, funding pitfalls, and the realities of startup life from both the boardroom and the kitchen table.

Key Takeaways: 

  • Talk with your support network early: Bring in spouses and family to align on expectations and risk tolerance before you dive in.

  • Respect investor concerns: Recognize that family-run businesses often face skepticism from funders; transparency with employees is vital.

  • Put people and culture first: Top-performing startups prioritize team cohesion, open dialogue, and customer focus above ego or control.

Episode 3: S12 E51 Sher Pt 1 with Jeremy Gray

EdTech strategist Cher Downing shares her perspective on today’s entrepreneurship landscape, highlighting the shift toward self-employment and the importance of finding (and articulating) your unique niche.

Key Takeaways: 

  • Identify and articulate your niche: Go beyond broad experience—define what you’re uniquely great at and why it matters.

  • Plan with purpose: Launching with a clear outline, measurable goals, and flexible milestones is essential for avoiding common startup failure traps.

  • Leverage your experience: Use your hard-won industry insights and connections to shape your offer and stand out from the crowd.

Episode 4: S12 E52 Sher Part 2 with Jeremy Gray

Cher returns for an honest discussion on conquering imposter syndrome, leveraging networks, and thriving as an entrepreneur in the hybrid, post-pandemic world.

Key Takeaways: 

  • Build and activate your network: Early clients often come through referrals—be proactive, clear, and unafraid to ask for help.

  • Embrace free (and low-cost) tools: Platforms like Canva, Google Workspace, and iMovie can help you look professional and punch above your weight.

  • Keep learning and wearing every hat: Early-stage entrepreneurs benefit from hands-on experience; free classes and resources can fill skill gaps until you can delegate.

Host Bio

Jeremy Gray is a seasoned international business leader, fractional CFO, and the insightful voice behind “Practical Solutions to Difficult Problems.” With decades of hands-on experience helping startups and growing companies navigate tricky terrain, Jeremy delivers real-world guidance, unvarnished analysis, and the occasional dose of European wit.

Mentioned Resources

Next Steps & Final Thoughts

Ready to move from insight to action? Start by getting brutally honest about your “why,” your team, and the everyday realities of entrepreneurship. Schedule that candid conversation with a co-founder, reach out to someone in your network, or brainstorm your specific niche until it’s crystal clear. Don’t let the fear of failure or the weight of the unknown stop you—every thriving business started with imperfect first steps and plenty of pivoting along the way.
Most importantly, remember: entrepreneurship is a journey, not a solo-destination. Embrace the power of your people, leverage the (often free) digital tools at your disposal, and keep leaning into learning. And if you ever need a nudge or a practical solution to a difficult problem? You know where to find us—helping you navigate one business challenge at a time.

Ready to dive deeper, connect with like-minded entrepreneurs, or get practical advice tailored to your situation? Visit businessinasia.org or connect with Jeremy Gray directly via LinkedIn. Here’s to smart strategies, resilient teams, and products your customers will love!

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