Tales From The Sky Lounge-A Business Podcast

Today in the Sky Lounge we are joined by Virginie Glaenzer, fractional CMO at TechCXO and author of ""The Economy of Abundance."" From landing in Silicon Valley with four suitcases during the height of the dot-com boom to building community-driven marketing strategies that outperform traditional branding, Virginie shares insights from 25 years of digital transformation. She explains why the AI revolution exceeds the internet boom in scope, how Gen Z is rejecting traditional business models, and why the future belongs to co-creators rather than controllers. Plus hear about her minimalist lifestyle, founding the Acorn Oak women's community, and why Dubai's mall-centric culture shocked this world traveler.

What is THE SKY LOUNGE?

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

ABOUT OUR HOST:

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6

Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN

Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658

Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge

Follow Tales From The SkyLounge on Social Media

X/Twitter: https://x.com/TFTSkyLounge

Instagram: https://www.instagram.com/tftskylounge/

Learn more about TechCXO: https://www.techcxo.com/

Production/Design: James Liebman

Music: Soundstripe/Cody Martin-Sunrise

Today in the Sky Lounge, we are joined by Brantley Fry, Partner at TechCXO, specializing in human capital management. Brantley shares her remarkable journey from environmental lawyer working on the largest spills in US history to political service as state director for a US Senator, and eventually to the startup world, where she helped navigate a successful acquisition by Quest Diagnostics. Her philosophy of being a "connector" between people and policy has guided every career move, and she reveals the inside story of managing culture and communication during M&A. Plus, hear about her transformative 500-mile walk across Spain on the Camino de Santiago.

What is THE SKY LOUNGE?

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

ABOUT OUR HOST:

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6

Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN

Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658

Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge

Follow Tales From The SkyLounge on Social Media

X/Twitter: https://x.com/TFTSkyLounge

Instagram: https://www.instagram.com/tftskylounge/

Learn more about TechCXO: https://www.techcxo.com/

Production/Design: James Liebman

Music: Soundstripe/Cody Martin-Sunrise

Today in the Sky Lounge, we are joined by Alex Gafford from BlueStreet Capital, who's living proof that working smarter beats working harder every single time. Nine years ago, Alex's company discovered an asset that boosted their KPIs by 24% and revenue by 30% without spending a dime. That asset? Time itself. Through their five-hour workday experiment, they cracked the code on peak performance - turns out knowledge workers max out at five hours of real productivity, and everything after that is just expensive theater. Alex reveals the wild world of financing AI infrastructure and raw GPUs while working just 25 hours a week, plus why multitasking is quietly stealing 28% of your day.

Check out and subscribe to our new series SpeedRun here: https://www.youtube.com/playlist?list=PLfeCS-Varb4hlUN_ngCG9Nr2VXOJ8XH4Z

What is THE SKY LOUNGE?

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

ABOUT OUR HOST:

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6

Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN

Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658

Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge

Follow Tales From The SkyLounge on Social Media

X/Twitter: https://x.com/TFTSkyLounge

Instagram: https://www.instagram.com/tftskylounge/

Learn more about TechCXO: https://www.techcxo.com/

Production/Design: James Liebman

Music: Soundstripe/Cody Martin-Sunrise

Today in the Sky Lounge we are joined by Joe Gruca, Partner in Revenue Growth at TechCXO. Joe shares his remarkable journey from getting laid off during the 2008 financial crisis to helping grow Hire iQ, a pioneering automated interview platform, into a successful predictive hiring platform used by global giants like Delta Airlines. Now helping early-stage tech CEOs accelerate growth, Joe offers hard-earned insights on building repeatable sales motions, the evolution of B2B selling, and why founder-led sales are both essential and limiting.

ABOUT OUR GUEST:

As a founder, as a CRO and CSO, I’ve been in your shoes as someone who’s had to make the hard calls when the numbers didn’t line up, or scale fast when they suddenly did. I know what it takes to build from zero, and how to keep momentum when growth starts to shift.

Over the course of my career, I’ve led GTM strategy for everything from early-stage startups to PE-backed scaleups, and Fortune 500 companies. What ties it all together is a commitment to results, clarity, and putting the right structure in place to turn potential into performance. I’m here to help companies move faster, align better, and grow smarter. Because I’ve been where you are, and I know how to get you to what’s next. That’s why the C-suite turns to me when they’re out of runway, looking for real growth, or ready to ditch the slideware for sustainable bottom-line impact.

What is THE SKY LOUNGE?

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

ABOUT OUR HOST:

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6

Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN

Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658

Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge

Follow Tales From The SkyLounge on Social Media

X/Twitter: https://x.com/TFTSkyLounge

Instagram: https://www.instagram.com/tftskylounge/

Check out our new series SpeedRun where Todd takes a look at the latest AI technologies. https://www.youtube.com/playlist?list=PLfeCS-Varb4hlUN_ngCG9Nr2VXOJ8XH4Z

Learn more about TechCXO: https://www.techcxo.com/

Production/Design: James Liebman

Music: Soundstripe/Cody Martin-Sunrise

Today in the Sky Lounge, Todd Merrill interviews Mike Biwer, CEO of Cavallo, discussing his journey to the company, the importance of distribution in the economy, and the challenges and strategies in the software and ERP space. They explore the origin of Cavallo's name, the company's growth, customer satisfaction, and the significance of profitability in distribution. Mike shares insights on navigating ERP changes, the role of private equity, and how to approach economic cycles. He also offers advice for aspiring software CEOs, emphasizing the need for product market fit and understanding customer problems.

What is THE SKY LOUNGE?

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

ABOUT OUR HOST:

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6

Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN

Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658

Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge

Follow Tales From The SkyLounge on Social Media

X/Twitter: https://x.com/TFTSkyLounge

Instagram: https://www.instagram.com/tftskylounge/

Learn more about TechCXO: https://www.techcxo.com/

Production/Design: James Liebman

Music: Soundstripe/Cody Martin-Sunrise

Bob Brogan joins us in the Sky Lounge to share his journey as Managing Partner at TechCXO for the Great Lakes Region. He pulls back the curtain on four decades in operations, IT, consulting, and strategy—including the story behind an incredible $100 million exit. From his family's surprising connection to the Chicago Bears to what really makes a business investable, this conversation delivers wisdom that's been battle-tested through multiple economic cycles.

ABOUT OUR GUEST:

Value Creation Expert

-My outcomes and deliverables

-Led numerous Buy/Sell-side Transactions totaling > $250M

-Enabled Revenue, GM & EBITDA Growth synchronously as CFO.

-Delivered multi-million $ CF improvements for companies

-Automated key functions to reduce cycle times & drive GM performance

My style and attributes

-Collaborative & Mentor

-Versatile

-Passionate

-Player/Coach -Team Builder

-Simplifying the Complex

-Integrity Matters

My background

-35 years in business - variety of C-Level leadership roles

-Operational & Financial Leader with $5.0M-$100M in Revenue

-Strategic Advisor for Private, VC & PE portfolio companies

-Track record of delivering EBITDA & CF Improvement

-Enable Strategic Metrics for all levels of the Organization

-Deep expertise in Enterprise SaaS, Recurring Rev. Services & Supply Chain

-Transaction Readiness & Exit Support

My top 5 areas of expertise

-Strategy Definition & Execution (Enterprise Alignment)

-Financial Performance Improvement (KPI, Metrics, etc.)

-Executive & Board Reporting (Visibility, Forecast, Actuals)

-Transaction Readiness & Execution

-Finance & Accounting Standardization

What is THE SKY LOUNGE?

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

ABOUT OUR HOST:

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6

Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN

Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658

Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge

Follow Tales From The SkyLounge on Social Media

X/Twitter: https://x.com/TFTSkyLounge

Instagram: https://www.instagram.com/tftskylounge/

Learn more about TechCXO: https://www.techcxo.com/

Production/Design: James Liebman

Music: Soundstripe/Cody Martin-Sunrise

Joining us today in the Sky Lounge is Teja Yenamandra, founder of Gun.io — the dev marketplace built for engineers who don’t belong on job boards. From martial arts to macro trends, Teja breaks down why great hiring is about rhythm, not resumes; how AI is reshaping the shape of work itself; and what most startups forget after the match is made. This is a founder story built on cold calls, precision matching, and scaling trust — not headcount.

What is THE SKY LOUNGE?

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

ABOUT OUR HOST:

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6

Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN

Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658

Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge

Follow Tales From The SkyLounge on Social Media

X/Twitter: https://x.com/TFTSkyLounge

Instagram: https://www.instagram.com/tftskylounge/

Learn more about TechCXO: https://www.techcxo.com/

Production/Design: James Liebman

Music: Soundstripe/Cody Martin-Sunrise

Joining us today in the Sky Lounge is Michael Weinstein — fractional CFO, economic strategist, and finance veteran — who brings his hard-won insights and wit to an time of financial uncertainty in the current economic climate. From early days at Anheuser-Busch (yes, there was free beer) to senior roles in asset management, Michael has seen more business cycles than most of us have had iPhones.

We dig into the structural fractures in today’s economy, why uncertainty is stalling investment, and how tariffs are creating ripple effects across industries. Michael breaks down why venture capital exits are clogged, the “overvalued” truth behind many private companies, and how interest rates are shaping (and stalling) our next wave of innovation. Plus, we explore how entrepreneurship might be the escape hatch — if we’re bold enough to build what’s next.

Chapters

0:00

Introduction to Michael Weinstein and His Career

2:47

Current Economic Landscape and Uncertainty

5:47

Impact of Tariffs on the Economy

8:55

Venture Capital and Market Dynamics

12:04

The Role of Interest Rates in Economic Growth

14:55

Foreign Investment and Market Reactions

18:06

Corporate Profitability and Tax Implications

21:03

Historical Context of Economic Cycles

24:03:00

Employment Trends and Economic Shifts

34:40:00

The Economic Impact of COVID-19 on Small Businesses

40:07:00

Entrepreneurship as a Catalyst for Recovery

44:42:00

The Role of Innovation in Economic Growth

52:34:00

Navigating Corporate Politics and Skills Development

59:37:00

Travel Tales and Life Lessons

What is THE SKY LOUNGE?

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

ABOUT OUR HOST:

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6

Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN

Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658

Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge

Follow Tales From The SkyLounge on Social Media

X/Twitter: https://x.com/TFTSkyLounge

Instagram: https://www.instagram.com/tftskylounge/

Learn more about TechCXO: https://www.techcxo.com/

Production/Design: James Liebman

Music: Soundstripe/Cody Martin-Sunrise

Jeff Haynie joins us in the Sky Lounge to talk scaling Appcelerator, why JavaScript won, the soul of Silicon Valley, and how AI agents are reshaping everything. From early days coding for iPhones to launching Agentuity—his latest startup focused on cloud-native agentic systems—Jeff shares a founder’s-eye view of what’s next for AI, startups, and software infrastructure.

ABOUT OUR GUEST

Jeff Haynie is a seasoned entrepreneur and technical founder with a track record of launching and scaling five venture-backed companies, collectively raising over $175M in funding. With a deep passion for building tools and platforms that empower businesses through software, Jeff has spent his career at the intersection of technology and business impact. Currently, he is the founder of Agentuity, where he is pioneering the next evolution of AI agents—combining artificial intelligence with human ingenuity and creativity to reimagine how we shape the future.

CONTACT:
https://x.com/jhaynie?lang=en
https://www.instagram.com/jhaynie/
https://x.com/agentuity
https://www.instagram.com/agentuity_ai
https://www.youtube.com/@agentuity

What is THE SKY LOUNGE?

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

ABOUT OUR HOST:

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6

Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN

Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658

Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge

Follow Tales From The SkyLounge on Social Media

X/Twitter: https://x.com/TFTSkyLounge

Instagram: https://www.instagram.com/tftskylounge/

Learn more about TechCXO: https://www.techcxo.com/

Production/Design: James Liebman

Music: Soundstripe/Cody Martin-Sunrise

Joining us today in the Sky Lounge is Matt Oess, a seasoned leader in sales, marketing, and executive coaching at TechCXO. With over a decade of experience guiding C-suite executives, Matt shares invaluable insights on leadership coaching, AI-driven business transformation, and navigating the complexities of high-stakes decision-making.

We dive deep into AI’s game-changing potential, the evolving role of coaching in leadership, and how businesses can leverage AI for productivity, sales, and innovation. Matt also takes us behind the scenes of his work with the Krach Institute for Tech Diplomacy, where he’s helping shape global policies on emerging technologies like AI, semiconductors, and cybersecurity.

From early-stage startups to billion-dollar enterprises, Matt has seen it all. He reveals why vulnerability is a CEO’s secret weapon, how AI is revolutionizing business workflows, and why the next era of software might outgrow traditional SaaS models.

Join us for a thought-provoking discussion that bridges technology, leadership, and human potential—perfect for executives, tech enthusiasts, and emerging leaders preparing for tomorrow's challenges.

What is THE SKY LOUNGE?

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

ABOUT OUR HOST:

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6

Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN

Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658

Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge

Follow Tales From The SkyLounge on Social Media

X/Twitter: https://x.com/TFTSkyLounge

Instagram: https://www.instagram.com/tftskylounge/

Learn more about TechCXO: https://www.techcxo.com/

Production/Design: James Liebman

Music: Soundstripe/Cody Martin-Sunrise