The Breakout CEO
The Breakout CEO is a podcast for leaders who are building, breaking through, and leveling up. We're excited to feature bold leaders and sharp thinkers who help scale innovation, build real teams, and navigate the pressures of growth. Hosted by Jeff Holman—CEO advisor, legal strategist, and founder of Intellectual Strategies—the show features 30-minute, insight-rich conversations with entrepreneurs and experts operating at the edge of innovation and growth. Each episode dives into the mindset, strategy, and critical decisions behind real inflection points: the kind of moves that create traction, transformation, and breakout success in businesses with $5M–$50M in revenu...
6 - Persistence in Action: Redefining the Fintech Landscape with ASA's Landon Glenn
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the CEO and Founder at ASA, Landon Glenn. Landon shares his journey from humble beginnings to building ASA, which partners with banks and credit unions to securely connect financial data and services using advanced technologies.
He emphasizes the challenges of fintech entrepreneurship, the importance of financial education, key partnerships, and ASA’s vision to transform banking. Landon also reveals plans for a Nasdaq listing and emphasizes persistence, strategic networking, and mentorship as keys to his success.
Listeners ar...
5 - Pivoting in the Face of Adversity: Lessons from a Tech Leader’s Journey with Intel Corporation's Dr. Darren Pulsipher
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the Chief Solutions Architect at Intel Corporation, Dr. Darren Pulsipher. Darren discusses his diverse career, from teaching at Vanderbilt to leading digital transformation at Intel.
Darren shares pivotal “breakout moments,” including lessons learned from startup setbacks and hypergrowth leadership. He covers balancing passion with family, the challenges of managing up versus down, and practical advice for CEOs on leveraging AI and finding mentors to navigate growth and digital change.
Listeners are encouraged to nominate CEOs with compelling brea...
4 - Smart Strategies for a Thriving Software Development Business with DevSquad's Phil Alves
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the CEO at DevSquad, Phil Alves. Phil shares his journey from Brazil to building a scalable SaaS development company in the U.S. He discusses the challenges of scaling a service business, the importance of team structure, culture, and playbooks, and Phil’s focus on sustainable, bootstrapped growth over chasing venture capital.
Phil highlights his breakout moment, his philosophy on risk, and how DevSquad maintains quality by limiting clients and planning growth.
Listeners are encouraged to nominate CE...
3 - The Rollercoaster of Entrepreneurship: Embracing Ups and Downs for Growth with Startup Ignition Academy's John Richards
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the Founder and CEO at Startup Ignition Academy, John Richards. John shares his journey from academia to building and scaling businesses, including launching the first internet yellow pages and mentoring Utah’s top startups.
He discusses the importance of mentorship, pattern recognition, and the unique Utah startup culture. John also offers practical advice on lean startup methodology, choosing scalable business models, and building operational foundations before scaling.
Listeners are encouraged to nominate CEOs with compelling breakout journeys.
...2 - Cash Flow and Innovation: Strategies for Sustainable Growth in High ASP Markets with SubcontractorHub's Justin Brach
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the CEO at SubcontractorHub, Justin Brach. Justin shares how near-death experiences shaped his drive for balance and purpose in life and business.
He discusses his company’s innovative approach to decentralizing home services, leveraging AI, and scaling efficiently. Justin details their unique hybrid monetization model, the importance of rapid iteration, and maintaining a strong company culture focused on health and family.
Listeners are encouraged to nominate CEOs with compelling breakout journeys.
Check out Justin's work HE...
1 - From Crisis to Confidence: Unleashing the Breakout CEO Within with Jeff Holman
In the inaugural episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Josh Elledge of UpMyInfluence speaks to Jeff Holman.
Jeff is the founder and CEO of Intellectual Strategies. He explains the podcast’s mission: to spotlight CEOs who have overcome major business challenges and achieved breakthrough moments. Drawing from his experience providing fractional legal teams to startups, Jeff shares how these pivotal stories can inspire and empower other leaders.
Listeners are encouraged to nominate CEOs with compelling breakout journeys.
Check out Jeff's work HERE.
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