In this episode of The Breakout CEO, host Jeff Holman talks with Dr. Darren Pulsipher—advisor, speaker, author, and host of Embracing Digital Transformation—about the real turning points behind his career.
Dr. Darren recounts walking away from a high‑tech role after a blocked spinout and non‑compete, jumping into a non‑tech company as CIO, and riding it through explosive hypergrowth. Along the way, he learned that founders who scale must master managing up—stacking the deck before the board meeting, avoiding surprises, and trading details for decisive asks.
He also shares practical ways CEOs can delegate low‑value tasks to AI, keep passion without burnout, and build the strategic infrastructure (including a strong legal backbone like a fractional general counsel and clear IP strategy) to grow with confidence.
The moment: Early in his career, Dr. Darren built technology that a billion‑dollar employer refused to spin out. He put his badge on the table, walked out, and got slapped with a non‑compete. The startup plan stalled.
The turn: A friend called with an unexpected offer—run IT for a multi‑level consumer brand. Not high‑tech. Not the plan. He took it.
The breakout: Within two years, the company surged from a few million a month to $80M/month, ballooning to 1,500+ employees and a campus of buildings. As CIO, Dr. Darren learned a new game: speak in outcomes, not details; make decisions and own them; and manage up long before the board meeting. That crash course shaped everything that followed—his executive approach, his mentoring of scaling leaders, and his lens on digital transformation.
The lesson for CEOs: Breakouts often arrive disguised as detours. If you’ve built a great team and product, your next leap depends less on pushing harder downward and more on navigating upward—pre‑aligning directors and investors, bringing no surprises to the room, and asking for exactly what the business needs. Pair that with ruthless focus: automate the mind‑numbing work with AI, protect your energy, and keep your strategy written down and visible.
Listen to the full episode for Dr. Darren's detailed story and insights.
The founders who scale aren’t the ones with the most stamina—they’re the ones who change games.
Dr. Darren’s story shows how a hard stop can force the right upgrade: from managing people to managing up; from passion that burns hot to passion that endures; from doing it all to automating the low‑value work. Pair digital transformation with strategic infrastructure—board alignment, a fractional legal team or fractional GC, and a forward‑looking IP strategy—and you’ll innovate with confidence without betting the company on every decision.
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Advisor, speaker, and author helping CEOs and public‑sector leaders navigate digital transformation. Host of the top‑ranked podcast Embracing Digital Transformation and Embracing Digital This Week. Darren also teaches in Vanderbilt’s online M.S. in Computer Science program and serves as Chief Solutions Architect, Public Sector at Intel.
LinkedIn: https://www.linkedin.com/in/darrenpulsipher/
DrDarrenSpeaks.com is the platform of Dr. Darren Pulsipher—speaker, author, and advisor on digital transformation and generative AI. Through keynote talks, workshops, and his top-ranked podcasts, Darren equips leaders to embrace new technologies, align people and processes, and turn disruption into growth.
Website: https://drdarrenspeaks.com
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Jeff Holman is a CEO advisor, legal strategist, and founder of Intellectual Strategies. With years of experience guiding leaders through complex business and legal challenges, Jeff equips CEOs to scale with confidence by blending legal expertise with strategic foresight. Connect with him on LinkedIn.
Intellectual Strategies provides innovative legal solutions for CEOs and founders through its fractional legal team model. By offering proactive, integrated legal support at predictable costs, the firm helps leaders protect their businesses, manage risk, and focus on growth with confidence.
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The Breakout CEO podcast brings you inside the pivotal moments of scaling leaders. Each week, host Jeff Holman spotlights breakout stories of scaling CEOs—showing how resilience, insight, and strategy create pivotal inflection points and lasting growth.
Listen and subscribe on your favorite podcast platform:
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Want to be a guest—or know a scaling CEO with a breakout story to share? Apply directly at go.intellectualstrategies.com.
01:30 — Viral momentum without the blueprint
Darren’s podcast, Embracing Digital Transformation, hits #1 in Apple’s tech charts after five years of consistent shipping—proof that tenacity still beats tricks.
10:45 — The badge on the table
A blocked spinout leads Darren to resign—and a non‑compete closes the door. The unexpected opening: a CIO role outside tech.
20:05 — Hypergrowth, up close
From ~$3–4M/month to $80M/month in two years; scaling headcount to ~1,500 across multiple buildings. New muscle: managing organizations, not just people.
23:25 — Managing up beats managing down
Founders who scale learn to pre‑wire the board, avoid surprises, and ask for decisions—not airtime. Details derail; clear options win.
27:55 — Are you the visionary or the builder?
Most founders can’t (and shouldn’t) take a company to a billion‑dollar outcome. Choose your arena—and get a mentor outside your industry who has no stake other than your growth.
34:30 — Use AI for leverage, not as a crutch
Offload low‑value, repetitive tasks to AI so your brain stays in strategy mode. Use generative AI to spark ideas—then make the decisions yourself.
