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Most CEOs assume that winning means competing harder. Andrew Ackerman learned the opposite. When Dreamit Accelerator found itself stuck behind larger, more established competitors, the question wasn’t how to move from number three to number one. It was whether that race was worth running at all. This episode explores the pivotal decision to stop fighting for position in a crowded market and instead redefine the track entirely. If you’re competing aggressively but not gaining meaningful advantage, this conversation will challenge how you think about positioning, focus, and execution under constraint. Along the way, Andrew shares hard-earned lessons about: Why discovery beats build-first instinct Why defining success before acting prevents wasted cycles Why focus matters more than feature depth And why time, more than competition kills startups Check out Andrew's work at https://www.scv.vc/ Say hello to Andrew! LinkedIn: / andrewbackerman LinkedIn: / second-century-ventures Think you'd be a great guest on the show? Apply https://go.intellectualstrategies.com/ Chapters 00:00 Introduction and Icebreakers 00:01 Personal Insights and Leadership Skills 00:26 The Journey of Entrepreneurship 13:50 Transitioning to Dreamit 2.0 26:52 Learning from Experience and Iteration 44:09 Advice for Aspiring Entrepreneurs Get in Touch with Jeff Holman ⤵️ Website: https://www.intellectualstrategies.com/ Instagram: / holmantech Facebook: / jeff.holman.9678 LinkedIn: / holman ➖➖➖➖➖➖➖➖ The Breakout CEO is a podcast for growth-stage business leaders: founders, CEOs, and executive advisors who are scaling companies, navigating inflection points, and leading through rapid growth. Hosted by Jeff Holman, CEO advisor, legal strategist, and founder of Intellectual Strategies, the podcast features 30-45 minutes of insight-packed episodes with innovative entrepreneurs, scaling CEOs, expert operators, and CEO coaches behind high-growth ventures.