Startups, Survival, and Self-Mastery: Lessons from 30 Years as a Founder

Imagine stepping into the role of CEO at just 19 years old, navigating the whirlwind of business growth while wrestling with the weight of immense responsibility. That's precisely what our guest, Wil Schroter, founder of startups.com, experienced. Through candid reflections, he shares personal milestones that marked both triumphs and tribulations, revealing how the relentless pursuit of stability shaped his entrepreneurial path. Despite achieving financial success, Wil opens up about the physical and mental toll of overworking, emphasizing the crucial lessons in self-care and health he gained later in life. We tackle the nuances of ageism and leadership through Wil's experiences as a young CEO in the 1990s. His natural curiosity and passion for understanding people became his guiding force, allowing him to see beyond the surface and embrace empathy in business. Discover the origins of startups.com and how a period of managing multiple ventures led Wil to reevaluate his priorities, thanks to insights from his wife. This journey underscores the importance of aligning actions with values and reassessing what truly matters, especially in the ever-evolving startup landscape. Balancing work, health, and family emerges as a central theme, with a focus on maintaining personal connections within growing companies. Wil shares his insights on setting boundaries and preventing work from consuming every waking moment, a challenge many founders face. From the necessity-driven roles in early-stage companies to the adaptability required for scaling, his story offers valuable lessons for entrepreneurs aiming to harmonize business aspirations with personal well-being. Join us as we explore these compelling themes and gain a deeper understanding of the motivations and priorities that define a successful entrepreneurial journey. Timestamps 00:00 - Introduction and Welcome to the Legacy Podcast 00:37 - Reflecting on Wil's Journey from Young CEO at 19 01:20 - The Immense Pressure and Responsibility of Rapid Business Growth 02:15 - Personal Costs of Success: Physical and Mental Toll 03:05 - The Fear of Instability Rooted in Challenging Upbringing 04:00 - Insights on Health and Self-Care Learned Later in Life 04:55 - Navigating Ageism and Seniority as a Young CEO in the 1990s 06:00 - The Power of Curiosity and Asking Questions in Leadership 08:05 - Realization of What One Can Do vs. What One Should Do 11:07 - Exploring Startup Evolution and Learning from Mistakes 12:00 - Aligning Business Ventures with Personal Values and Passion 13:00 - Pivot from Fundable.com to Startups.com as Core Business 14:00 - The Necessity of Adaptability in Staffing and Leadership 16:00 - Maintaining Close Personal Connections Within Organizations 17:00 - Setting Boundaries to Prevent Work from Encroaching on Personal Life 19:00 - Insights into Creating Longevity and Sustainability in Entrepreneurship 21:00 - Encouragement to Teach and Inspire Future Entrepreneurs 22:00 - Wil's Commitment to Helping Others Build Their Own Destiny 24:00 - Where to Find More Information About Startups.com and Wil's Work 25:00 - Closing Remarks and Gratitude from the Podcast Host   Episode Resources: Find out what Wil is up to here: https://www.startups.com/ Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit businesslegacypodcast.com. Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit businesslegacypodcast.com to access the shownotes and additional resources on the episode.