Serial Entrepreneurship

The practice of repeatedly founding and scaling multiple ventures over time, applying lessons learned from previous startups to new opportunities.

25 episodes

Parallel Entrepreneurism: Shipping Startups Side by Side | Kirby Winters, Ep 50

Parallel Entrepreneurism: Shipping Startups Side by Side | Kirby Winters, Ep 50

Kirby Winters discusses launching multiple ventures simultaneously using AI-powered development, including Cyber Savi (a compliance automation platform), a vodka brand, and Unshucked (an oyster tracking app). He explains how agentic AI enables building production-ready software in weeks instead of years, the shift from consulting to outcome-based services, and strategies for selling cybersecurity compliance tools through MSP channel partners.

Inside Secrets to Angel and Crowdfund Investing | Karen Rands, Ep 47

Inside Secrets to Angel and Crowdfund Investing | Karen Rands, Ep 47

Karen Rands, founder of the Compassionate Capitalist Movement, discusses how individuals can build wealth by investing in entrepreneurs through angel investing and equity crowdfunding. She shares her journey from IBM intrapreneur to angel investor advocate, explains revenue-share investment models as alternatives to traditional equity deals, and outlines strategies for building diversified portfolios that generate both financial returns and social impact.

A Trauma Surgeon and Entrepreneur on Healthcare, AI and What's Next | Niral Shah, Ep 44

A Trauma Surgeon and Entrepreneur on Healthcare, AI and What's Next | Niral Shah, Ep 44

Niral Shah, a trauma surgeon and serial entrepreneur, discusses his journey from starting a search engine startup during the dot-com boom to returning to medicine and now investing in healthcare innovation. He shares lessons from shutting down his first company responsibly, explains why healthcare represents 18-21% of US GDP with poor outcomes, and identifies opportunities in AI-driven biotech, disintermediation of healthcare delivery, and multiomic drug discovery targeting aging as a treatable condition.

Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners | Chris Thomajan, Ep 42

Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners | Chris Thomajan, Ep 42

Chris Thomajan, a CFO with 35 years of experience across 100+ startups, discusses his career path from English major to finance leader in Boston's biotech ecosystem. He shares frameworks for evaluating founding teams, navigating venture capital cycles, and preparing companies for IPO, emphasizing that betting on the right 'jockey' matters more than the business idea itself.

Business Model First, Product Second: Thirty Years of Building Smarter | Steve Subar, Ep 40

Business Model First, Product Second: Thirty Years of Building Smarter | Steve Subar, Ep 40

Steve Subar, serial entrepreneur and inventor of MatFresher, discusses his business-model-first approach to building companies. After 30+ years founding and exiting ventures including Open Kernel Labs (acquired by General Dynamics), Subar explains how he validated product-market fit for MatFresher—an automated yoga mat cleaning machine—by manually cleaning mats at studios before building the product. He emphasizes innovating business models alongside technology, the importance of experience over information, and why wisdom beats rapid iteration.

Decades of Financial Strategy Across 70 Companies and Still Going | Neal Miller, Ep 39

Decades of Financial Strategy Across 70 Companies and Still Going | Neal Miller, Ep 39

Neil Miller, a partner emeritus at Tech CXO with nearly 20 years of fractional CFO experience across 70+ companies, shares his career journey from public accounting through multiple CFO roles at public companies to pioneering fractional executive work. He discusses value creation stories including Cloud Sherpas (acquired by Accenture) and Boomtown (90M+ revenue exit), the current venture capital environment, and how AI tools are compressing startup development cycles while raising the bar for execution speed.

Innovation, Timing, and Leadership for Entrepreneurs and Intrapreneurs | Louis Gump, Ep 38

Innovation, Timing, and Leadership for Entrepreneurs and Intrapreneurs | Louis Gump, Ep 38

Louis Gump, fractional CEO/COO and author of Inside Innovator, discusses his career building mobile businesses at CNN and The Weather Channel, the critical differences between entrepreneurs and intrapreneurs, and how founders can successfully transition into larger organizations post-acquisition. He emphasizes that innovation requires leadership commitment, cross-functional collaboration, and understanding when to adapt entrepreneurial instincts to corporate environments.

Decades of Financial Strategy, Still in the Game and Giving Back | Ted Stone, Ep 36

Decades of Financial Strategy, Still in the Game and Giving Back | Ted Stone, Ep 36

Ted Stone, a 72-year-old fractional CFO, discusses his decades-long career in financial leadership, including multiple private equity-backed M&A transactions, integration strategies, and current work helping companies navigate recapitalizations and ESOP transitions. He shares lessons from rolling up businesses, managing post-acquisition culture clashes, and why he continues working seven years past traditional retirement age.

Rewriting the Rules: Growth, AI, Community, and the Meaning of Wealth | Virginie Glaenzer, Ep 35

Rewriting the Rules: Growth, AI, Community, and the Meaning of Wealth | Virginie Glaenzer, Ep 35

Virginia Glaenzer, fractional CMO and author, shares her journey from moving to Silicon Valley in 1998 with four suitcases to building tech companies during the dot-com era. She discusses how AI is reshaping work, why communities should be built into brand DNA rather than added as tactics, and introduces her 'economy of abundance' framework that challenges scarcity-based business models by asking 'how much is enough?'

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.

The Hidden Engine of the Economy: The Power of Distribution | Mike Biwer of Cavallo, Ep 31

The Hidden Engine of the Economy: The Power of Distribution | Mike Biwer of Cavallo, Ep 31

Mike Biwer, CEO of Cavalo, discusses how his company helps wholesale distributors optimize profitability through technology that controls pricing and margins at the line-item level. Founded by a distributor who achieved 10x industry-average profits, Cavalo evolved from a Microsoft Dynamics add-on to a multi-platform solution serving the $10 trillion distribution sector, where average pre-tax margins are under 5%.

Beyond Resumes: The Case for Talent-First, Human-Centered Hiring | Teja Yenamandra, Ep 29

Beyond Resumes: The Case for Talent-First, Human-Centered Hiring | Teja Yenamandra, Ep 29

Teja Yenamandra, founder of Gun.io, discusses building a talent-first freelance marketplace that connects senior software engineers with companies based on merit rather than price. He shares insights on remote work culture, AI's impact on software development, the importance of relationship-focused venture capital partnerships, and how the developer job market is shifting toward backend and AI implementation work.

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.

The Rise of Agentic Systems and AI-Driven Development | Jeff Haynie, Ep 27

The Rise of Agentic Systems and AI-Driven Development | Jeff Haynie, Ep 27

Jeff Haynie, serial entrepreneur and founder of Appcelerator (acquired after reaching 1M+ developers), discusses his journey from building cross-platform mobile frameworks in 2006 to launching Agentuity, a cloud platform for AI agents. He shares lessons from raising capital in Silicon Valley, navigating acquisitions, and why he believes agentic systems will require fundamentally different infrastructure than today's human-centric cloud.

Earning Every Win: Grit, Innovation, and Knowing When to Venture | Lisa Calhoun, Ep 25

Earning Every Win: Grit, Innovation, and Knowing When to Venture | Lisa Calhoun, Ep 25

Lisa Calhoun, managing partner of Valor Ventures, discusses her fourth-generation entrepreneurial background and leading seed-stage B2B AI and SaaS investments across the South. She explains venture capital's relational nature, the 2024 venture winter that shuttered 40% of smaller funds, and how AI is eliminating coding as a constrained resource while transforming software development economics.

Phishing, AI Scams, and the Ever-Intensifying Cybersecurity War | Antonio Pagano, Ep 23

Phishing, AI Scams, and the Ever-Intensifying Cybersecurity War | Antonio Pagano, Ep 23

Antonio Pagano, CTO and co-founder of Symbol Security and founder of Wano, discusses the evolution of cybersecurity threats—particularly AI-enhanced phishing attacks—and the human vulnerabilities that remain the weakest link in security. He shares insights from running two companies across continents, bootstrapping Symbol Security for six years, and building Wano's 45-person development team in Colombia while maintaining work-life balance and continuous learning.

Family Values, Ukrainian Excellence: Creating the Ideal Workplace | Adam Lehde, Ep 20

Family Values, Ukrainian Excellence: Creating the Ideal Workplace | Adam Lehde, Ep 20

Adam Lehde, co-founder of Happen Technologies, discusses building a hybrid software development company that partners US-based strategy with Ukrainian engineering talent. He shares his journey from mobile developer to entrepreneur, the cultural advantages of working with Ukrainian developers, and his philosophy of building a family-first company culture supported by community practices like F3 fitness groups.

Triathlons, Startups, and Success: A Playbook for Entrepreneurs | Kathryn O'Day, Ep 19

Triathlons, Startups, and Success: A Playbook for Entrepreneurs | Kathryn O'Day, Ep 19

Katherine O'Day, partner at Atlanta Ventures, discusses her journey from employee number nine at Pardot through two successful acquisitions (ExactTarget, then Salesforce) to becoming an early-stage investor and venture studio operator. She shares lessons on bootstrapping companies, building culture through core values, and why consistent execution over time—like training for an Ironman—matters more than short bursts of effort in entrepreneurship.

A Born Entrepreneur on Startups, Product Blueprints, and Global Scaling | Ghazenfer Mansoor, Ep 18

A Born Entrepreneur on Startups, Product Blueprints, and Global Scaling | Ghazenfer Mansoor, Ep 18

Ghazenfer Mansoor, founder of Technology Divers, discusses his journey from Pakistan to building a global software development company. He explains his 'blueprint methodology' for converting napkin sketches into production-ready applications, the challenges of managing distributed teams across continents, and how AI tools are transforming both software development and client operations. Mansoor emphasizes the importance of entrepreneur peer groups and shares insights on mobile app development trends.

Scout Skills, Leadership Hacks, and Smart Security in the Age of AI | Kirby Winters, Ep 17

Scout Skills, Leadership Hacks, and Smart Security in the Age of AI | Kirby Winters, Ep 17

Kirby Winters, fractional CISO at TechCXO, discusses his journey from telecom to cybersecurity consulting, emphasizing leadership lessons from Eagle Scouts and entrepreneurship. He covers the evolving threat landscape—from social engineering to AI-enhanced phishing—and explains how fractional security leadership helps SMBs navigate SOC 2, HIPAA, and CMMC compliance without full-time hires. The conversation explores VPN evolution, cyber insurance realities, and the critical need for proactive security planning before customer mandates or breaches force action.

Insights, Tips, Tricks and Wisdom from a Tech Veteran | Rob Reesor, Ep 11

Insights, Tips, Tricks and Wisdom from a Tech Veteran | Rob Reesor, Ep 11

Rob Reesor shares his journey from early AI expert systems development at Intellicorp through pioneering e-commerce at Virtual Vineyards to executive technology leadership across multiple private equity-backed companies. He discusses the evolution of software development practices, the challenges of technical debt management, and the critical importance of trust-based leadership in building high-performing engineering teams.

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.

Grit Becomes Growth: The Path from Pain to Transformation | Bart Foster, Ep 09

Grit Becomes Growth: The Path from Pain to Transformation | Bart Foster, Ep 09

Bart Foster shares his journey from corporate executive to founder of SoloHealth, a health screening kiosk company that scaled to 4,000 Walmart locations before he was forced out by his board. He discusses the emotional trauma of losing his company, his intentional relocation to Boulder, and founding Business Outside—a consulting practice that uses nature-based experiences to help leaders build authentic connections and live more intentionally.

Machine Learning at MIT to Entrepreneurial Growth and Fundraising Success | David Morczinek, Ep 08

Machine Learning at MIT to Entrepreneurial Growth and Fundraising Success | David Morczinek, Ep 08

David Morczinek, CEO of Airworks, discusses his journey from aerospace engineering at Airbus to founding a geospatial AI company at MIT. He explains how Airworks analyzes aerial data from drones, satellites, and aircraft to automate infrastructure mapping, the pivot from pure AI to AI-plus-services when customers weren't ready for full automation, and navigating multiple funding rounds from seed to private equity while maintaining work-life balance.

From Startup to Successful Exit: Lessons from a Healthcare Entrepreneur | Jan Heybroek, Ep 03

From Startup to Successful Exit: Lessons from a Healthcare Entrepreneur | Jan Heybroek, Ep 03

Jan Heybroek shares his 17-year journey building and selling a medical market research company to a medical education firm in 2021. He discusses the M&A process, post-acquisition integration challenges, healthcare industry trends including personalized medicine and AI diagnostics, and lessons learned about transparency, perseverance, and the value of fractional executive talent for scaling startups.

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