What does it take to grow a startup from the ground up, weather industry changes, and scale sustainably? In this episode, we hear from an experienced entrepreneur who has spent over 17 years building and scaling businesses, especially in the challenging climate tech industry. From leading a company to $50 million in revenue to facing the hard realities of failure, our guest shares essential insights on resilience, strategic growth, and the lessons learned from navigating an unpredictable market.

Discover how he tackled cash flow issues, handled rapid industry changes, and maintained a culture of innovation even as his business grew. This episode also delves into practical advice on founder-led sales, managing competitive pressures, and maintaining mental well-being amid the demands of startup life.

Listen in to learn:

• The value of founder-led sales and why staying close to the sales process can drive growth.
• Key strategies for maintaining cash flow and managing risks as your business scales.
• Tips for founder mental health, from building resilience to celebrating small wins daily.

Press play to gain actionable insights on building a sustainable business and lessons from real startup failures.

What if women in remote and underserved regions had access to world-class mentors? In this episode, we dive into the story of a social entrepreneur who has created a global mentorship network to connect corporate leaders with women in the developing world. Her mission is to empower women through mentorship, allowing them to build leadership skills, gain confidence, and access opportunities that were once out of reach.

Our guest shares her personal journey from corporate to social impact, explaining how she transitioned from a structured business environment to creating a values-driven organization. She reflects on the importance of mentorship, why vulnerability is a strength in leadership, and how the right mentor can make all the difference in a founder’s journey.

Tune in to learn:

• The transformative power of mentorship and how it builds leaders.
• Why staying true to your values is essential for sustainable success.
• Practical advice for early-stage founders on building inclusive, impact-focused cultures.

Hit play to explore how this powerful mentorship program is fostering future female leaders and driving social change across continents.

Did you know that tens of thousands of people are currently trapped in modern slavery in Australia alone? In this episode, we meet a dedicated social entrepreneur who left a corporate career to start a powerful movement against modern slavery. She shares how her nonprofit organization fights human trafficking and supports survivors through education, advocacy, and innovative business models.

Join us as our guest talks about the challenges and breakthroughs of building a mission-driven organization, from learning hard lessons in hiring to setting up social enterprises like cafes that fund her cause. She explains how diversifying revenue streams has helped sustain her mission, even through COVID, and the impact of Australia’s Modern Slavery Act on corporate responsibility.

Listen to gain insights on:

• How to start and scale a social enterprise focused on human rights.
• Strategies for balancing purpose and profit in a nonprofit organization.
• Tips for creating meaningful partnerships with businesses to drive change.

Press play to discover an inspiring story of resilience and innovation in the fight against modern slavery.

Are you overwhelmed by the complexities of holistic health and wellness? In this episode, we follow the journey of a wellness entrepreneur who turned her own health struggles into a mission-driven business. After facing burnout in a high-stress finance job, she realized the need for accessible, data-driven solutions in holistic health. Now, she leads a company dedicated to empowering people with personalized wellness products backed by science.

Join us as our guest shares the ups and downs of building a wellness brand, from securing $11 million in funding to overcoming the challenges of being a female founder in a male-dominated industry. Learn how she navigates resilience, manages rejections, and makes tough calls—all while balancing her personal life and growing her online presence.

Tune in to discover:

• Proven strategies for navigating investor rejections and securing funding as a female founder.
• The importance of building community and brand authenticity in wellness.
• Practical insights on managing stress, preventing burnout, and maintaining work-life balance as an entrepreneur.

Press play to hear an inspiring story of purpose, resilience, and innovation in the wellness space.

What does it take to build a startup culture that thrives on resilience, empathy, and performance? In this episode, we explore the journey of a seasoned people and talent leader who’s dedicated her career to helping tech startups build strong, high-performing teams.

Our guest shares her unique path from studying theology to working in recruitment, where she discovered her passion for helping founders create winning teams. With insights gained from working across deep tech, fintech, and high-growth startups, she discusses the realities of scaling early-stage teams, managing different personality types, and the importance of creating a strong, adaptable culture. She also dives into her approach to "radical candor" in feedback, her thoughts on the evolving workplace, and why empathy and flexibility are crucial for sustainable performance.

Tune in to learn:

• The keys to hiring and retaining top talent in a fast-paced startup environment.
• How to build a culture that aligns performance with values for long-term success.
• Practical advice for founders transitioning from working in their business to working on their business.

Press play to uncover valuable lessons in leadership, culture, and team-building that can help your startup thrive.

In this episode, we explore how one entrepreneur is bridging the digital divide and bringing empathy into the tech industry. With over 30 years of experience in IT, our guest shares her journey from her early days in customer support to founding a tech company focused on making technology accessible and user-friendly for all, especially underserved communities.

Hear her story of founding a business with a unique culture centered on kindness and respect, and discover how she’s driving impactful initiatives to help the elderly and underserved populations gain confidence with technology. From hospital iPad lending programs to training young digital mentors, she’s building community and connection in powerful ways.

Listen to gain insights on:

• The importance of empathy and understanding in tech support.
• How accessible tech initiatives can benefit both young and elderly communities.
• Strategies for managing rapid growth and maintaining a healthy work culture.

Press play to learn how this innovative leader is reshaping tech support for everyone and creating a lasting impact in her community.

Keywords for Discoverability:
Digital accessibility, tech support, community building, digital mentorship, bridging the digital divide, startup success, empathy in tech.

Episode Summary

Steve Plummer, a seasoned entrepreneur with over a decade of experience, shares his journey through multiple startups and the various roles he's taken on, including Head of Product and CEO.

He discusses the challenges of being a solo founder, the importance of building a strong co-founding team, and the need for robust go-to-market strategies.

Steve highlights his experience with scaling technology and handling B2B sales, emphasising the importance of understanding both the product and the market. He also touches on his involvement with handball in Australia, aiming to develop talent for future Olympic games.

Listen on:

YouTube:⁠ YouTube Channel⁠

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Apple Podcasts:⁠ Apple Podcasts⁠

iHeartRadio:⁠ iHeartRadio⁠

Amazon Music:⁠ Amazon Music⁠

Socials:

TikTok:⁠ TikTok⁠

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YouTube:⁠ YouTube⁠

Website:⁠ www.failwisdom.com⁠

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Disclaimers:

The views and opinions expressed in this podcast are those of the hosts and guests and do not necessarily reflect the official policy or position of the podcast owner or sponsor. Any content provided is for informational purposes only and should not be interpreted as professional advice. Always consult with a qualified professional for specific advice tailored to your situation.

Chapters

• 00:00 - Introduction and Background
• 08:58 - Starting a Business and Dealing with Challenges
• 13:14 - Ransomware Attack and Cybersecurity Measures
• 16:09 - Lessons Learned and Tips for Early-Stage Founders
• 29:13 - Protecting Your Business and Managing Finances
• 37:22 - Maintaining Mental Health and Well-being
• 45:31 - Future Plans and Giving Back

#StartupJourney #Entrepreneurship #TechInnovation #ProductManagement #FounderAdvice #BusinessGrowth #Leadership #TechScaling #B2BSales #AustralianStartups

Curious about the mindset and resilience it takes to succeed in the startup world from a young age? In this episode, we dive into the journey of a young entrepreneur who transitioned from high school ventures to launching multiple startups in his early twenties.

Our guest reflects on his early experiences, from his first social media project at 14, to an unexpected venture selling drinks at school, and the lessons he learned along the way. With a hands-on approach to building businesses, he shares the skills he gained through trial and error, which have fueled his passion for problem-solving and innovation. He also talks about co-founding a personalized training app, working with offshore staffing solutions, and exploring the pay-later travel industry.

Tune in to discover:

• Practical insights on pricing strategies and managing costs in startups.
• How resilience, cold calling, and networking open doors to new opportunities.
• Tips for validating a product and building it to adapt to real user feedback.

Press play to learn from this inspiring entrepreneurial journey and gain insights to fuel your own startup path!

Links and Resources

• Connect on LinkedIn
• Learn more about Fishburners
• Explore ActiveMate

Release Schedule:
New episodes are released every Wednesday, providing insights from inspiring startup journeys.

Keywords for Discoverability:
Startup success, entrepreneurial journey, resilience in business, startup networking, personalized training app, offshore staffing, pay-later travel.