All Episodes

Adoption Isn't Impact: Where Enterprise AI Coding Stalls | Nadeem Haider | Ep 54

Nadeem Haider, a software engineering leader with 20 years at Citrix, maps the five-stage maturity curve enterprises face when adopting AI coding agents—from individual experimentation through team standardization to full agentic development. He argues that adoption metrics don't equal transformation, explains why 'AI ergonomics' of legacy codebases determine agent effectiveness, and advocates for risk-stratified code review where humans focus on high-blast-radius changes while agents handle boilerplate.

The Crawl-Walk-Run Playbook for Adopting AI | Jim Hasty, Ep 53

Jim Hasty, founder of Cogle Group, discusses his company's evolution from technology consulting to AI-powered software products. He shares lessons from building Plan Checkers, an AI tool that reduces municipal permit review time from weeks to minutes, and outlines a crawl-walk-run framework for enterprise AI adoption focused on automating emotionally draining tasks rather than chasing adoption metrics.

Founders: These Are the Mistakes You Don't Know You're Going to Make | Steve Walsh, Ep 52

Steve Walsh, an angel investor and startup advisor, shares lessons from 25 years building multi-billion dollar B2B divisions at Cox and Comcast before transitioning to helping early-stage founders. He discusses common founder mistakes, when to raise capital, the importance of customer validation before building product, and how he filters 6,000 conversations down to 69 investments through rigorous vetting and founder education.

If You're Not Making Money, You're Not Worth Money: 1,000 Valuations | Gregg Ficery, Ep 51

Gregg Ficery, founder of Integgra Advisory Services, discusses his 15-year career in business valuation, explaining when companies need valuations (fundraising, 409A compliance, M&A, litigation), how to maximize company value, and current trends in venture capital and AI investment. He shares his journey from dot-com survivor to Silicon Valley Bank to independent consultant, plus his side project: a book documenting pre-NFL professional football history.

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.

The CEO Is the Salesperson: Why Founders Can't Hand Off the Pitch | Jen Bonnett, Ep 49

Jennifer Bonnett, a longtime tech entrepreneur and former ecosystem builder at ATDC and Invest Atlanta, discusses her transition back into technology through AI experimentation. She shares lessons from building a search engine in 1997, her current work vibe coding consumer apps with Claude, and her philosophy that CEOs must personally sell for at least the first year before delegating. The conversation explores how AI is lowering barriers to entrepreneurship while emphasizing that founders still need strong networks, customer discovery skills, and the discipline to market early.

What Builders Get Wrong About Capital, From Someone Who Knows Both Sides | Kumar Ampapathini, Ep 48

Kumar Ampapathini, a fractional CFO and former Wall Street banker, discusses his transition from software engineering at Cisco to investment banking and eventually fractional CFO work. He explains how AI is transforming startup economics, why institutional investors prioritize path-to-profitability over pure growth, and what founders misunderstand about capital. Kumar shares M&A negotiation insights and emphasizes that strong founders matter more than perfect products.

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.

Ep 46 Rachel Zeller of Kitces.com—Hiring Humans in an AI World

Rachel Zeller, Managing Director at Kitces.com, discusses how her fully remote financial education company is adapting hiring practices in response to AI-generated applications. She explains their human-centric approach: requiring robust application forms instead of easy-apply, manually reviewing every submission, asking candidates to submit AI transcripts alongside work samples, and prioritizing culture fit over technical skills that can be trained.

Crypto Grows Up: Building at the Intersection of Blockchain and AI | John Church, Ep 45

John Church, lead product manager at Nethermind and adjunct professor at Duke University, discusses his journey from DAO leadership to institutional blockchain work. The conversation covers stablecoins, zero-knowledge cryptography, AI agents interacting with blockchain, and how crypto infrastructure is maturing from speculative chaos to institutional adoption. Church emphasizes fundamental understanding over tactical skills as AI transforms software development.

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.

How Two Veterans Are Solving Business Development with TractionBD | Yates & Bedol, Ep 43

John Yates, a tech attorney with 44 years of experience, and Greg Bedol, a serial entrepreneur and consultant, discuss their AI-powered business development platform Traction BD. They explain how AI is transforming professional services business development from a centuries-old mentor-based model into an automated system that helps lawyers, accountants, and consultants maintain relationships and convert prospects into clients through persistent, personalized outreach.

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.

2026 Trends: Trust in AI, Healthcare, College, AGI & More | Bryan Dennstedt, Ep 41

Todd and Bryan Dennstedt review their 2025 AI predictions, finding they accurately forecasted the AI trough of disillusionment, agentic AI emergence, and VC conservatism. They predict 2026 will be defined by organizational absorption of AI capabilities rather than new breakthroughs, with agentic workflows becoming default, SaaS pricing models compressing, and trust verification emerging as a critical business category. They emphasize that rapid AI-powered software development is fundamentally changing startup economics and making previously marginal business ideas viable.

2025 Travel Stories: What Happens When You Get Out There to Make Things Happen!

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

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

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.

Big Tobacco to Government Contracts: Building Breakthrough Brand Campaigns | Mike Martin, Ep 37

Mike Martin, fractional CMO at Tech CXO, discusses his career building breakthrough brand campaigns—from the Truth anti-tobacco campaign's guerrilla marketing tactics to Super Bowl spots for Monster.com. He shares lessons on creative courage, navigating difficult bosses, and how AI is transforming marketing while emphasizing that creativity still requires human oversight and strategic foundations.

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

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?'

Why Connecting People and Process Is Your Secret Weapon | Brantley Fry, Ep 34

Brantley Fry, partner at Tech CXO, shares her unconventional career path from environmental litigation to political operations to human capital management. She discusses her work on major environmental disasters (TVA coal ash spill, BP oil spill), serving as state director for a U.S. senator, and helping a health tech startup through acquisition. The conversation explores employment agreements, non-traditional hiring, and building culture through M&A transitions.

The 5-Hour Workday: Maximum Productivity in Minimal Time | Alex Gafford, Ep 33

Alex Gafford, a corporate finance executive at Blue Street Capital, discusses his company's nine-year experiment with a five-hour workday that increased productivity by 24% and revenue by 30%. He explains how condensed work schedules, protected focus time, and AI tools enable knowledge workers to achieve peak performance while maintaining work-life balance, challenging traditional assumptions about hours worked versus results delivered.

SpeedRun Ep19 Marketing Plans with Virginie Glaenzer - Tales from the Sky Lounge

Todd and Virginie demonstrate live how to build a complete marketing plan using AI tools like ChatGPT and Claude. They identify lack of clarity as the biggest barrier to AI adoption among executives, design a five-step 'AI Value Blueprint' service offering targeting CMOs, CROs, and COOs in B2B SaaS, and develop persona-specific messaging and automation workflows—all within one hour using conversational AI.

SpeedRun Ep20 Canva with Mike Martin - Tales from the Sky Lounge

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.

SpeedRun Ep18 wordpress Tales from the Sky Lounge

A developer attempts to fix WordPress SEO and indexing issues using Claude AI, discovering that AI agents are treated as bots by robots.txt and encountering limitations when automating bulk changes. The experiment reveals both the potential and pitfalls of AI-assisted site maintenance, particularly the importance of human checkpoints.

SpeedRun Ep12 Conference Attendee Email Lead Parsing Tales from the Sky Lounge

A developer experiments with using Claude AI to automate conference lead generation by parsing a PDF attendee list and creating a complete HubSpot marketing campaign. Claude autonomously researches the conference, segments attendees, writes email sequences, and designs lead scoring workflows—but hits output limits when generating the final CSV, revealing practical constraints in AI-driven business development automation.

SpeedRun Ep13 Email Marketing Write an Agent Tales from the Sky Lounge

A CTO demonstrates how Claude AI can autonomously design and build a complete email marketing automation system from a single meeting recording. Starting with meeting notes and a one-line goal, Claude generated technical architecture, wrote Python code, created file structures, and produced sample email sequences—all through conversational prompts without traditional software development.

SpeedRun Ep11 Medical Videos Ideation Tales from the Sky Lounge

A marketing strategist uses Claude AI to develop a content strategy for a medical SaaS client with an AI diagnostic chatbot. The AI generates platform-specific recommendations for LinkedIn, YouTube, and TikTok, analyzes successful medical content creators, and proposes viral marketing concepts inspired by 'Will It Blend' and House MD, while cautioning against IBM Watson's failed broad-claims approach.

SpeedRun Ep14 Ask a Blue Shirt Tales from the Sky Lounge

A CTO demonstrates building a vector database search system in one evening using Claude Code, outpacing weekend projects built with no-code tools. He contrasts Claude Desktop's planning capabilities with Claude Code's implementation power, showing how AI enables rapid development of production-grade infrastructure including AWS deployment, MCP servers, and WordPress plugins.

SpeedRun Ep 06 Durable Agent Writing -Tales from the Sky Lounge

A CTO demonstrates how to convert Claude Desktop prototypes into production-ready AI agents using Python, Pydantic, and LangGraph. The episode walks through extracting MCP tool configurations and system prompts from chat sessions, then generating deployable code that can run on schedules or respond to events—illustrating how agent development costs are approaching zero.

SpeedRun Ep 10 audio engineer local bizdev p -Tales from the Sky Lounge

A father uses Claude AI to help his college-age son, an aspiring audio engineer, develop a comprehensive business plan for launching a recording studio service in Atlanta's hip-hop scene with a $350 budget. The AI generates detailed market analysis, pricing strategies, venue partnerships, social media tactics, and a 90-day action plan that validates the son's instincts while expanding his strategic thinking about client acquisition and business development.

SpeedRun Ep 05 Projects with SOW from Notes and Emails -Tales from the Sky Lounge

A consultant demonstrates using Claude Desktop with MCP integrations to automatically generate client proposals by synthesizing meeting transcripts, emails, and web research. The AI system searches Google Drive for templates and meeting notes, analyzes Gmail exchanges, researches the client online, and produces a complete statement of work—all from a single prompt.

SpeedRun Ep 09 Resource Use for ICP + GTM Plan -Tales from the Sky Lounge

A fractional CTO demonstrates using Claude AI with deep research mode to generate a comprehensive business development plan. By uploading marketing materials, case studies, and service offerings, the AI produces detailed ideal customer profiles, multi-channel outreach strategies, budget allocations, and personalized contact sequences—illustrating how experienced professionals can leverage AI to automate strategic planning while maintaining the judgment to guide and refine outputs.

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%.

Road Warrior to Business Architect: 40 Years of Transforming Companies | Bob Brogan, Ep 30

Bob Brogan shares four decades of operational and strategic consulting experience, from early data warehousing work at IBM subsidiaries to leading turnarounds and exits. He discusses his approach to business transformation through modular design, cash cycle management, and the importance of mentorship—both as an angel investor evaluating founders and through his Legacy Guild charity providing scholarships to students who've lost parents.

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

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

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.

Coaching Elite Leaders, AI Productivity and the Need for Tech Diplomacy | Matt Oess, Ep 26

Matt Oess, a sales and marketing consultant and executive coach at TechCXO, discusses his coaching practice for C-suite leaders, his deep dive into AI productivity tools over the past 14 months, and his advisory role with Purdue's Croc Institute for Tech Diplomacy. He demonstrates practical AI automation workflows he's built using platforms like Make.com, explains the maturity progression from zero-shot generative AI to multi-agent systems, and shares insights on how AI is transforming business operations and the SaaS industry.

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.

Sales, Marketing, and AI: How to Survive, Scale, and Avoid Stagnation | Alan Gold, Ep 24

Alan Gold, a 30-year marketing and sales veteran, discusses his career spanning Wi-Fi launches, speech recognition, and AI tools across startups and M&A. He covers current market uncertainty, the shift from sales tactics to strategy, AI's impact on entry-level roles, and why promoting top salespeople to management typically fails. Gold emphasizes listening skills, differentiation, and strategic thinking over tactical execution.

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.

2025 Trends: AI, Venture Capital, and the Future of Work | Bryan Dennstedt, Ep 22

Bryan Dennstedt, fractional CTO at Tech CXO and sustainable investing advocate, discusses 2025 trends with host Todd. They cover venture capital's conservative shift post-SVB, AI's permeation across business (from agents to trust frameworks), the rise of niche podcasts and influencer marketing, and crypto's regulatory thaw under new US leadership. Core insight: AI and blockchain will become as fundamental as electricity, but organizations must navigate trust, compliance, and the trough of disillusionment before realizing transformative value.

Travel Stories Compilation: Perspectives, Peeves, Perks, Profound Lessons and Priceless Stories

Sales, Marketing, Sumerians and Avoiding Founder's Disease | James Rozich, Ep 21

Jim Rozich, founder of Wheels Up Sales and Marketing, discusses common mistakes early-stage founders make when going to market—particularly 'Founder's Disease,' where entrepreneurs lead with product features instead of customer value. He covers CRM implementation, value-based email messaging, discovery call methodology, and how AI tools should support rather than replace human sales judgment.

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

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

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

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.

Leadership, Resilience, and Sales Mastery | Rich Makover, Ep 16

Rich Makover, a fractional Chief Revenue Officer and executive coach at TechCXO, discusses his journey from Penn State lacrosse player to CPA to sales leadership at Avon and beyond. He shares insights on hiring athletes for sales roles, the importance of resilience over winning, situational coaching methodologies, and his transition to fractional leadership and executive coaching, including his decade-long mentoring program for Penn State lacrosse.

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.

AI Roundtable: Where Do We Stand and What's Next? | Ep 14

A panel of AI and machine learning practitioners—Joel Foreman (Director of AI at Airworks), Nicos Vasilioglou (VP of Research at Relational AI), and Kevin (Partner at TechCXO)—discuss the current state of AI, distinguishing hype from reality, practical applications, and future directions. They explore LLM capabilities, ethical concerns around training data, the need for AI infrastructure standards, and emerging opportunities in medicine, optimization, and enterprise applications.

Mastering UK-US Market Entry from Either Side of the Pond | Marc McCarthy, Ep 13

Marc McCarthy, founder of Pro Consult IQ, discusses the complexities of B2B software expansion between UK and US markets. He covers cultural sales differences, regulatory considerations across US states, the importance of hiring locally, and strategic decisions around partnerships versus direct market entry. McCarthy emphasizes that shared language creates false assumptions about ease of expansion, and successful cross-Atlantic growth requires understanding time zones, legal frameworks, pricing strategies, and customer expectations that differ significantly between markets.

The Modern Marketing Landscape, from a Seasoned Expert | Katherine Hunter-Blyden, Ep 12

Katherine Hunter-Blyden, a fractional CMO, discusses her career journey from Fortune 500 companies like Ford and Progressive to serving small businesses. She covers the evolution of marketing measurement, the importance of email marketing and content strategy, brand versus direct response tactics, and how AI tools are transforming marketing efficiency while many professionals remain hesitant to adopt them.

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

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

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

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.

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.

A Journey Through Valuations, Ventures, Visions and Vodka | Mike Blake, Ep 06

Mike Blake, founder of High Score Strategies, discusses business valuation methodology, the changing landscape of patent protection, and his journey from venture capital to running a valuation consultancy from Portugal. He shares insights on helping founders navigate term sheets, the limitations of valuation in early-stage negotiations, and the story of launching Atlanta's Startup Lounge networking events that helped build the city's entrepreneurial ecosystem.

Winning Strategies from Gridiron Grit to Healthcare Innovation | Jay Kleinman, Ep 05

Jay Kleinman, a 30-year healthcare sales and business development veteran, discusses how lessons from playing D1 football at Auburn under Pat Dye shaped his approach to building commercial teams for early-stage healthcare companies. He covers segmentation strategy, discovery-based selling, and the transformation of elder care through digital health and telemedicine adoption accelerated by COVID-19.

From Rowing to Venture Capital: Lessons in Teamwork and Growth | Mark Flickinger, Ep 04

Mark Flickinger, partner at BIP Ventures, discusses his journey from mechanical engineering and competitive rowing to venture capital. He explains BIP's platform-heavy approach to supporting portfolio companies, the firm's focus on high-net-worth investors, and strategies for navigating the current venture market. Flickinger emphasizes the importance of board governance, team-based competitive experience, and building sustainable businesses during economic downturns.

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.

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

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.