Louis Gump joins us in the Sky Lounge to explore a question every founder and executive faces eventually: what happens after the acquisition? In this candid conversation, Louis shares how he helped build the mobile business at CNN.com, led digital transformation at The Weather Channel, and became the steady hand guiding post-acquisition innovation at startups and growth-stage companies alike.
We unpack the differences between entrepreneurs and intrapreneurs, what makes someone thrive inside a big company post-acquisition, and how timing and self-awareness shape every meaningful career move. Louis also discusses the importance of clarity in strategy, the value of not rushing change, and why keeping founders involved after a deal often leads to better outcomes.
Louis is also the author of The Inside Innovator, a practical guide to driving innovation from within established companies — ideal for leaders navigating post-acquisition roles or scaling without the founder title.
Whether you’re scaling, selling, or staying to build the next chapter — this episode will meet you at the crossroads.
ABOUT OUR GUEST:
Partner in the Executive Operations Practice of TechCXO
Author of ""The Inside Innovator: A Practical Guide to Intrapreneurship"" available at booksellers and here: https://louisgump.com/
Experienced executive with a demonstrated track record of success in the media industry on multiple platforms. Skilled in Digital Strategy, Innovation, Local Media, Multiplatform Content and Advertising, Connected TV, Mobile Media and Marketing, Management, and Mergers & Acquisitions (M&A). Strong business development professional with an MBA focused on General Management and Leadership.
CONTACT:
LinkedIn: https://www.linkedin.com/in/louisgump/
Site: https://louisgump.com/
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 Mike Martin, fractional CMO at TechCXO and creative veteran behind some of advertising's most impactful campaigns. Mike shares the inside story of creating the legendary Truth anti-smoking campaign, producing million-dollar Super Bowl spots that ran only once, and why he believes vanilla content is the biggest risk brands can take. From dealing with maniacal bosses who threw storyboards down hallways to accidentally creating viral moments with ice cream trucks at elementary schools, Mike's career spans the evolution from traditional advertising to AI-powered creativity. Plus, hear his travel adventures including swimming with 400-pound pigs in the Bahamas and getting rewarded for government success by having his program cancelled.
ABOUT OUR GUEST:
Mike Martin is often described as a muse for creative-minded entrepreneurs and executive leaders who struggle to synthesize the brand story swirling in their heads. He operates at the intersection of Performance & Persuasion with an unwavering belief that revenue growth is accelerated when creativity has accountability and content marketing is grounded in human truth. Mike is a rare breed of CMO who cut his teeth on the creative side, building award-winning campaigns before pivoting into being an agency owner, tech startup founder, and software development shop CMO before exiting.
Mike is well acquainted with the entrepreneurs journey and navigating periods of prosperity and adversity. With decades of experience in consumer marketing, B2B & B2C SaaS, G2C, and tech startups, he helps brands recalibrate strategy, reconfigure teams, and refocus on revenue growth as an interim and fractional CMO.
CONTACT:
Email: mike.martin@techcxo.com
LinkedIn: https://www.linkedin.com/in/mike-martin-atl/
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 Ted Stone, a 72-year-old fractional CFO at TechCXO who's living proof that experience beats age in the business world. Ted shares insights from four decades of private equity deals, including rollups, spinoffs, and integrations that taught him every strategy in the playbook. He explains how the ""silver tsunami"" of baby boomer business exits is creating unprecedented opportunities for private equity firms, why ESOPs are emerging as attractive exit strategies, and how fractional executive work lets veterans stay in the game past traditional retirement. Plus, hear his incredible travel story about surviving not one but two helicopter incidents on a single business trip.
ABOUT OUR GUEST:
Ted is an experienced CFO who has worked with companies from start-ups to $2 billion global firms across technology-intensive industries including software, energy efficiency, logistics, and manufacturing.
He combines finance, operations, and engineering expertise to build transparent management systems and drive value creation through operational turnarounds, acquisitions, and growth opportunities. Ted's collaborative, low-ego approach bridges technology teams with business leaders, and he has extensive experience in capital raising, M&A transactions, and consistently helping companies outperform competitors in equity value creation.
CONTACT:
Email: ted.stone@techcxo.com
LinkedIn: http://www.linkedin.com/in/tedstonecfo
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 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
<p>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.</p>
<p>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.</p>
<p>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.</p>
<p>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.</p>
<p>What is THE SKY LOUNGE?</p>
<p>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.</p>
<p>ABOUT OUR HOST:</p>
<p>Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.</p>
<p>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.</p>
<p>Subscribe and turn on notifications to listen to new episodes as they launch!</p>
<p>YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6</p>
<p>Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN</p>
<p>Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658</p>
<p>Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge</p>
<p>Follow Tales From The SkyLounge on Social Media</p>
<p>X/Twitter: https://x.com/TFTSkyLounge</p>
<p>Instagram: https://www.instagram.com/tftskylounge/</p>
<p>Learn more about TechCXO: https://www.techcxo.com/</p>
<p>Production/Design: James Liebman</p>
<p>Music: Soundstripe/Cody Martin-Sunrise</p>
Joining us in the Sky Lounge today is Lisa Calhoun, founding managing partner of Valor Ventures! Lisa shares her journey as a fourth-generation entrepreneur, the importance of relationships in venture capital, and her investment philosophy. She and Todd discuss the current state of the venture landscape, the impact of AI on startups, and advice for young entrepreneurs. Lisa shares her insights on navigating challenges in the industry and the transformative power of travel and personal growth.
Growing up, working for her family's commercial print shop, cold-calling clients as a teenager, and witnessing the rise of the microcomputer revolution firsthand, Lisa's got a lot of experience with making things happen in the tech industry. She explains how those experiences shaped her investing philosophy at Valor, where she leads seed-stage AI and SaaS deals across the South.
ABOUT OUR GUEST:
Lisa Calhoun is an experienced leader in venture capital. Lisa was recently named Atlanta Investor of the Year by Startup Atlanta and highlighted among Business Insider’s Top 30 Women Early-stage Investors in the U.S. She is the founder and managing partner of Valor Ventures, the South’s first woman-led, institutional venture capital firm, now investing its third fund. Valor’s portfolio employs just over 1,000 people and has a footprint across 25 countries.
Under her leadership, Valor leverages a high performance portfolio of AI and SaaS software companies based in the South. Valor’s first checks into AI startups change the real world. Valor portfolio firms are helping guide major law firms (Visalaw); major city industrial cores around vehicle automation (Autonoma); US hospitals (AI genomics and mental health monitors); as well is on the front in Ukraine (AI drone intelligence).
Valor is also known for developing Vic, a visionary AI-powered investment management platform integrated with industry leaders like Salesforce, Carta, and PitchBook. Valor funds are backed by notable institutional investors as well as thoughtful private capital.
CONTACT:
https://www.linkedin.com/in/lisacalhoun/
https://valor.vc/
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 Alan Gold, a marketing and sales strategist with decades of experience in M&A, startups, and growth strategy. Alan has been on both sides of the table—helping companies scale, navigating acquisitions, and leading turnarounds. From being part of the launch team for Wi-Fi technology to working on speech recognition and AI-powered business tools, he’s seen how markets evolve and what it really takes to stay ahead.
We dive into:
Plus, Alan shares hilarious and wild travel stories, including a baboon with an attitude and getting detained in Colombia.
If you’re in startups, consulting, M&A, or just trying to grow a business, this one’s for you.
Alan’s a veteran of the B2B marketing world, having been an executive in startups, international public companies, high-growth technology and services companies, leading marketing and sometimes both marketing and sales efforts.
Over my career, I have launched new technologies that are integral to our daily lives, repositioned companies to take advantage of new markets, and been involved in M&A activities on both sides of the process. I’ve worked in many different industries, including software, supply chain, medical and pharma, healthcare applications and services, as well as telecom and AI-driven planning software.
Email: alan.gold@techcxo.com
Phone: 978-886-1910
Tales from the SkyLounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people who are shaping the future of these industries. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.
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.
Joining us today in the Sky Lounge is Antonio Pagano, founder of Wawandco and co-founder of Symbol Security. Todd and Antonio discuss cybersecurity’s human element, compliance, evolving phishing attacks, and AI’s role in scams. Antonio shares insights on real-world incidents, cyber insurance trends, and the dynamics of running a business with a remote co-founder. He also delves into the challenges and successes of entrepreneurship, emphasizing the balance between ambition and well-being, and how staying grounded fuels creativity and success.
ABOUT OUR GUESTAntonio Pagano is a visionary entrepreneur from Barranquilla, Colombia, dedicated to making technology accessible. In 2013, he founded Wawandco, a software development company delivering efficient, high-quality solutions for US and European clients. His expertise spans web applications, mobile solutions, APIs, and UX.
Antonio co-founded Symbol Security, a SaaS company focused on cybersecurity awareness. By addressing human risk factors, Symbol Security helps organizations protect their assets. His innovation extends to tools like Releaso, leveraging AI for product communication, and Retabler, optimizing data workflows. Beyond business, Antonio is a devoted family man who enjoys sports, outdoor activities, and quality time with loved ones.
Contact:Email: antonio@wawand.co | antonio@symbolsecurity.com
Socials What is THE SKY LOUNGE?Tales from the Sky Lounge is a podcast that takes you through business, consulting, and venture investing, featuring stories from entrepreneurs, consultants, and investors shaping these industries.
ABOUT OUR HOSTTodd Merrill is an experienced software executive assisting clients as a fractional or interim CTO and CISO at TechCXO. A SaaS leader, Todd blends technical expertise with mentoring.
Subscribe and turn on notifications to listen to new episodes as they launch! Follow Tales From The Sky Lounge on Social MediaProduction/Design: James Liebman
Music: Soundstripe/Cody Martin - Sunrise
Today in the Sky Lounge, Bryan Dennstedt joins Todd Merrill as they bring their unique perspectives from years in business, technology, and investing for a deep dive into the trends that will shape 2025. From venture capital’s cautious return to the AI-driven reshaping of industries, this episode is a candid discussion about what’s next for tech, work, and investing. Everything from whether AI is going to hit speed bumps or keep climbing, blockchain’s role in authenticity in AI and the future of collaboration tools is on the table!
ABOUT OUR GUESTBryan Dennstedt is an accomplished Fractional CTO or Fractional CIO with TechCXO in Charlotte, North Carolina, where he has focused his efforts as a hands-on Fractional CTO and Interim CIO with numerous clients. He is an expert in mobile application development, healthcare integrations, and all aspects of telemedicine and has worked on over 40 engagements in a fractional capacity for the firm. His experience includes managing all information technology operations, from fractional CTO product development to Interim CIO large-scale technology migrations. Bryan works to ensure that his clients’ high-level Information Technology roadmaps are well-defined and then digs into the details to ensure that established metrics, accountability, and results are being delivered by the team he leads. Once a client is up and running with his methodologies, the Fractional CIO capacity can be leveraged in an ongoing model, and it can be ramped up to Part-Time CIO as needed throughout a project.
Contact:Tales from the Sky Lounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people who are shaping the future of these industries. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.
ABOUT OUR HOSTTodd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CISO as a partner at TechCXO. With a history of leadership and innovation in SaaS product development, Todd combines technical expertise with a knack for mentoring.
Subscribe and turn on notifications to listen to new episodes as they launch! Follow Tales From The Sky Lounge on Social MediaProduction/Design: James Liebman
Music: Soundstripe/Cody Martin - Sunrise
This year has been a whirlwind of adventure, and as we gear up for an incredible 2025, we’re hitting pause to share something special—our favorite travel stories! From mind-boggling mishaps to inspiring lessons learned on the road, these tales are all about the joy, challenges, and magic of exploring the world while living in the world of business.
We’re so grateful to our amazing guests and YOU, our listeners, for making this journey unforgettable. Sit back, relax, and let these stories take you places. Here’s to another year of growth, adventure, and connection. See you in 2025!
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 HOSTTodd 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! Follow Tales From The SkyLounge on Social MediaProduction/Design: James Liebman
Music: Soundstripe/Cody Martin-Sunrise
Joining us today in the Sky Lounge is Jim Rozich, founder of Wheels Up Sales and Marketing. Jim specializes in helping early-stage startups overcome the unglamorous yet essential challenges of building solid sales and marketing processes. From CRM implementation to crafting value-driven email campaigns, Jim shares practical insights that founders need to create traction and scale effectively.
In this episode, we explore the realities of early-stage startup sales, common pitfalls, and the art of developing scalable processes that work. Jim also shares his thoughts on the evolving venture investing landscape and why startups are becoming the “new bricks and mortar.” Plus, we dive into the tools and tactics that can help founders thrive, including the strategic use of CRMs, leveraging AI for marketing, and the critical importance of personalization in sales.
ABOUT OUR GUEST
With a dynamic career spanning two decades in sales and marketing, I’m Jim Rozich. As an industry veteran, I have consistently navigated the intricacies of bringing products and services to market - honing my expertise in crafting tailored strategies for CRM implementation, devising lead generation tactics, and refining messages that resonate with target audiences.
My genuine passion for business development and startups is what sets me apart. Embark on your journey with confidence, knowing that you have a trusted ally with a 20-year history of propelling businesses to new heights.
Socials
Contact info
Email: jim@wheelsupsales.com
What is THE SKYLOUNGE?
Tales from the SkyLounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people shaping these industries' future. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.
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!
Follow Tales From The SkyLounge on Social Media
Production/Design: James Liebman
Music: Soundstripe/Cody Martin-Sunrise
Today in the Sky Lounge, we’re joined by Adam Lehde, co-founder of Happen Technologies, to explore the art of building businesses across borders. Adam shares how he turned his initial doubts about outsourcing into a thriving hybrid business model that bridges Midwest strategy with Ukrainian tech talent.
We dive into Adam’s journey from a rocky internship to mastering mobile development, the resilience of Ukrainian developers amidst wartime, and why culture always matters in tech. Adam also reveals how personal priorities and work-life balance shaped his company’s values and offers insights into the ever-evolving remote work landscape.
And yes, you’ll want to hear why Ukraine’s tech scene is full of PhDs and rocket scientists—and what makes it an underestimated hub for startups and innovation.
ABOUT OUR GUESTPrior to founding Happen Technologies, Adam spent his career building mobile apps and managing software projects for national brands, including Mazda, Hyundai, Anheuser-Busch, National Car Rental, and more.
He has a passion (maybe an obsession) for improving everything he encounters and looks for EVERY opportunity to make it better.
Socials Contact infoEmail: adam@happentechnologies.com
What is THE SKYLOUNGE?Tales from the SkyLounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people shaping these industries' future. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.
ABOUT OUR HOSTTodd 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! Follow Tales From The SkyLounge on Social MediaProduction/Design: James Liebman
Music: Soundstripe/Cody Martin-Sunrise