Crisis-Resilient Entrepreneurship

Strategies for navigating major economic disruptions like 9/11, the 2008 financial crisis, and COVID-19 while maintaining business continuity and customer relationships.

7 episodes

From Pink Slip to Pivot: Predictable Sales in Unpredictable Markets | Joe Gruca, Ep 32

From Pink Slip to Pivot: Predictable Sales in Unpredictable Markets | Joe Gruca, Ep 32

Joe Gruca, newly joined partner at Tech CXO, shares his journey from corporate VP of Sales through founding Higher IQ (an AI-powered interview platform acquired after raising venture capital) to fractional revenue leadership. He discusses navigating the 2008 financial crisis as an accidental entrepreneur, building predictable sales motions for early-stage B2B SaaS companies, and how AI is transforming both sales execution and customer success while the fundamentals of relationship-building remain constant.

Tariffs and Economic Uncertainty: How We Got Here and What's Next | Michael Weinstein, Ep 28

Tariffs and Economic Uncertainty: How We Got Here and What's Next | Michael Weinstein, Ep 28

Michael Weinstein, a fractional CFO with decades of Wall Street and corporate finance experience, analyzes the current economic uncertainty driven by tariff policy, Federal Reserve decisions, and structural market challenges. He explains how tariffs function as a massive tax increase, why venture capital liquidity has frozen, and how uncertainty prevents corporate investment—while arguing that entrepreneurship and new business formation will ultimately lead the economy out of stagnation.

IT Roundtable: Leadership and Cost Optimization in Challenging Times | Ep 15

IT Roundtable: Leadership and Cost Optimization in Challenging Times | Ep 15

Three fractional IT executives discuss cost optimization strategies during economic downturns, including cloud infrastructure waste, vendor management, and strategic hiring decisions. They share specific examples of reducing AWS spend by 50-75%, eliminating unused software licenses, and the risks of cutting technical staff without preserving domain expertise.

Hard-Won Lessons from a Long and Successful Tech Journey | Chris Caparon, Ep 10

Hard-Won Lessons from a Long and Successful Tech Journey | Chris Caparon, Ep 10

Chris Caparon, co-founder and former CEO of Sephoria Software, shares his 20-year journey building an accounts receivable automation company from a garage startup to a successful exit to private equity. He discusses navigating multiple economic crises, evolving technology platforms, and the relentless customer focus that enabled his bootstrapped company to serve Fortune 500 clients across 110 countries.

Cultivating Resilience Through Adaptation, Partnership and Growth | Christy Johnson, Ep 07

Cultivating Resilience Through Adaptation, Partnership and Growth | Christy Johnson, Ep 07

Christy Johnson, performance engineering lead at VIP Ventures, discusses her unconventional path from microfinance in Costa Rica to steel manufacturing to venture capital. She shares lessons from seven years as CEO of a portfolio company, the importance of culture in remote teams, and VIP's hands-on approach to helping founders through focused strategy, investor symposiums, and operational coaching.

Mastering Marketing Evolution in the Digital Age | Lewis Goldman, Ep 02

Mastering Marketing Evolution in the Digital Age | Lewis Goldman, Ep 02

Lewis Goldman, a growth marketer at TechCXO, discusses his career evolution from advertising psychology to digital transformation leadership at major companies like CNBC, Citigroup, and MetLife. He shares lessons from the dot-com era, explains modern marketing channel dynamics between Google and Meta, and describes how AI is reshaping both targeting capabilities and content authenticity in digital marketing.

Building Authentic Leadership and Culture in Startups | Maria Goldsholl, Ep 01

Building Authentic Leadership and Culture in Startups | Maria Goldsholl, Ep 01

Maria Goldsholl, fractional Chief People Officer at TXO, discusses authentic leadership, building trust-based cultures in startups, and the value of fractional executive services. She emphasizes psychological safety, transparent communication, and learning from career setbacks as foundations for effective leadership and organizational growth.

Want to go deeper?

Work With Me
Back to all topics