Startups, Survival, and Self-Mastery: Lessons from 30 Years as a Founder
Release Date: 05/19/2025
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Confidence isn’t a personality trait, it's a system you can train. In this episode of the Business Legacy Podcast, Paul Dio sits down with mindset and confidence expert Natalie Plamondon-Thomas to explore how our brain creates stress, doubt, and emotional loops and how to interrupt them. Natalie shares the neuroscience behind confidence, the difference between the logical mind and unconscious mind, and why most people accidentally program themselves for stress. Through powerful metaphors and practical tools, she explains how to rewrite internal dialogue, break anxiety cycles, and access peak...
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Choose Growth Over Comfort and Build a Lifeswitch
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Helping People Sleep Better with Data-Driven Reviews
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What happens when you mix analytical rigor with an everyday product like a mattress? You get NapLab, a data-driven review site created by Derek Hales, whose mission is to help people sleep better by eliminating the guesswork behind mattress shopping. In this episode of the Legacy Podcast, host Paul Dio sits down with Derek to explore how a personal frustration with mattress shopping led to a full-time career in objective sleep product testing. What started as a weekend side project quickly turned into one of the most trusted mattress review platforms online. Derek walks through his meticulous...
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Redefining Professional Outreach in the Age of AI
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Is cold email dead? Not even close you’re just doing it wrong. In this episode of the Legacy Podcast, host Paul Dio speaks with Adam Rosen, founder and CEO of Email Outreach Company (EOC), a service helping startups and businesses scale their outreach through strategic, professional cold email. From landing Fortune 500 clients like Amazon and Bank of America to getting replies from Mark Cuban and Ajay Banga, Adam shares real stories that prove email is still one of the most powerful tools in business if you know how to use it. He breaks down what’s changed (and what hasn’t) in the email...
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Rethinking Water Quality and Community
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What happens when a software founder returns to her roots in Maine and sees clean water as the foundation for local economic development? In this episode of the Legacy Podcast, host Paul Dio speaks with Jen Millard, co-founder and CEO of Maine Love, a growing water brand with a mission far bigger than hydration. After years leading tech companies and consumer product startups, Jen returned to her home state to build something that mattered not just a brand, but a vehicle for job creation, sustainability, and local reinvestment. From repurposing idle breweries to creating a supply chain that...
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Why Connection and Curiosity Drive Business Growth
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From Disruption to Advantage with Futurist Insights
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Integrating Vitamins into Daily Habits
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The Intersection of Real Estate and Tax Advisory
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Matthew Wessels, partner at Wessels Realty and Tax Advisors, takes center stage as he shares his compelling journey from the hills of New Hampshire to carving a unique niche in the real estate and tax advisory world. Matthew's story is a testament to the power of combining passions, as he skillfully marries his accounting background with a fervor for real estate development. Our conversation uncovers how he transitioned from the corporate treadmill to co-purchasing his first property, igniting a career that now stands at the intersection of real estate analysis, general contracting, and...
info_outlineImagine 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.
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