Eric Stenson on Risk, Responsibility & the Entrepreneur’s Journey
What really keeps entrepreneurs awake at night? In this episode of What Keeps You Awake.TV, host David Hooser sits down with Eric Stenson — accomplished IT leader, CEO, and serial entrepreneur — to unpack the real challenges of building, protecting, and scaling businesses.
🔥 Inside This Episode:
• The weight of leading 100+ employees while serving 7,000+ clients
• Why data security is one of the biggest risks SMBs face today
• Lessons from leaving a stable C-suite role to start a software company
• How growing up with both an attorney mother and entrepreneurial father shaped his path
• The tradeoffs of freedom vs. responsibility in business ownership
• Why problem-solving, product–market fit, and resilience drive long-term success
Eric also shares hard-won insights on vendor relationships, pivots, and why entrepreneurship is equal parts sleepless nights and unlimited upside.
📌 If you’re a small business leader or aspiring founder, this episode delivers valuable perspective on the risks and rewards of entrepreneurship.
🔔 Don’t forget to subscribe to What Keeps You Awake.TV for more real stories from leaders building, scaling, and protecting their businesses.
🔑 Hashtags:
#EricStenson #Entrepreneurship #SmallBusiness #BusinessGrowth #Leadership #SerialEntrepreneur #DataSecurity #PivotEquity #StartupLife #BusinessStrategy #WhatKeepsYouAwakeTV #PhoenixBusiness #SMB
