Tales From The Sky Lounge-A Business Podcast

Ep42 Chris Thomajan: Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners Jan 21, 2026

Today in the Sky Lounge, we are joined by Chris Thomajan, a CFO who's spent 35 years with startups and has worked with over 100 companies—mostly in biotech, mostly venture-backed, always as the steady hand while everyone else loses their minds.

Chris didn't start in finance. English major, disco worker in London, law firm (hated it), Columbia Business School, then three decades of pattern recognition in the startup world. He's developed a particular skill: knowing which CEOs will make it and which won't. He's even categorized them like wine—from Beaujolais Nouveau (enthusiastic first-timers) to Port (dictators you really don't want to work for).

We explore what makes Boston's biotech ecosystem unique, why nine out of ten boards need to be ""managed away,"" and what it really takes to prepare a company for IPO. Chris breaks down the current VC landscape (""too many capital calls, not enough distributions""), why he'd never personally invest in early-stage biotech, and the one quality that separates great CEOs from the rest: the ability to delegate.

Plus: hitchhiking 5,000 miles across America in an era when that was still possible.

ABOUT OUR GUEST:

Chris Thomajan has been a CFO for over 30 years in a variety of industries, including: biotech, medtech, healthcare tech, software, digital media, Internet services and investment banking.

Chris was a founding partner of America’s Growth Capital, a boutique investment bank focused on emerging growth technology companies. He was the early-stage CFO/VP Operations for Asurion Corporation, which is a closely held, multi-billion-dollar private company. He was also the founding CFO for a pioneering Internet company, Delphi Internet Services, which was acquired by News Corporation in 1993.

Chris has extensive experience in raising debt and equity. He has also been involved in numerous M&A transactions and has managed the operations of several start-up companies during rapid revenue growth. He received a B.A. from Dartmouth College and an M.B.A. from Columbia University.

CONTACT:

https://www.linkedin.com/in/chris-thomajan-1879143

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

Ep41 Bryan Dennstedt of AIWithBry—2026 Trends: Trust in AI, Healthcare, College, AGI & more Dec 31, 2025

Today in the Sky Lounge, Todd is joined by Bryan Dennstedt for the second year running to review how their 2025 AI predictions played out and forecast what's coming in 2026.

They tackle the AI trough of disillusionment head-on—turns out they nailed it, though some people are well up the other side, while others are still stuck at the bottom. The conversation moves from commercial real estate's ongoing struggles to the rise of agentic workflows that are replacing simple chatbots. Bryan explains the shift from ""light bulbs to motors""—companies moving beyond point solutions to build real automation factories.

The duo unpacks SaaS pricing compression, the manufacturing renaissance happening through local 3D printing, trust verification, and speed starting companies in the AI era. They close with a lightning round covering college's ROI, world models versus LLMs, healthcare disruption, and whether we'll hit AGI by 2027.

Check out Part 2 on Bryan's pod AIWithBry: https://bry.net/ai

ABOUT OUR GUEST:

Bryan 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:

LinkedIn: https://www.linkedin.com/in/phingers/

Website: https://bry.net/ai

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

2025 Travel Stories: What Happens When You Get Out There to Make Things Happen! Dec 25, 2025

What a year of incredible journeys and unexpected connections! As 2025 comes to a close, we're bringing you our most memorable travel stories from the Sky Lounge—those moments when business trips turned into adventures and chance encounters became game-changing partnerships. These stories capture what really happens when entrepreneurs, consultants, and investors step out of their comfort zones to build something meaningful.Thank you to our remarkable guests who shared their journeys, and to you—our listeners—for joining us every step of the way.

Pour yourself something good and let these stories remind you why the best opportunities often come from simply getting out there. Here's to 2026—may it bring even bolder moves and bigger adventures. See you in the Sky Lounge!Check out and subscribe to our new series SpeedRun here:

Look for the Blog post for this episode here:

What is THE SKY LOUNGE?

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.

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, DevOps, QA, and Customer Success professionals.Subscribe and turn on notifications to listen to new episodes as they launch!YouTube:

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Learn more about TechCXO:

Production/Design: James LiebmanMusic: Soundstripe/Cody Martin - Sunrise

Ep40—Steve Subar—Business Model First, Product Second: Thirty Years of Building Smarter Dec 10, 2025

Today in the Sky Lounge, we are joined by Steve Subar, a COO/CEO with 30+ years of building and exiting companies who's now tackling an altogether different problem with his new company MatFresher: dirty yoga mats.

Steve shares how he validated his latest venture, not by building a machine first, but by setting up a folding table at yoga studios with rubber gloves and antiseptic spray. Would anyone actually pay two bucks to clean their mat? (Hint: yes, they would)

We explore his journey from founding Open Kernel Labs (which ended up in 1.6 billion phones before its acquisition by General Dynamics) to consulting for tech companies, where he witnessed founders make the same expensive mistakes over and over. Steve breaks down why ""information plus experience equals wisdom,"" why he'll never do B2B sales friction again, and how the NSA's paranoia became his go-to-market strategy.

Plus: why he once flew Sydney to San Francisco for a meeting that didn't result in funding—but changed everything anyway.

ABOUT OUR GUEST:

Steve Subar is an experienced technology leader with 20+ years of success launching and scaling high-growth tech companies from inception to IPO or Fortune 500 acquisition. He is known for novel product and business model innovation, focusing on enterprise applications, B2B, and SaaS.

As a founder, CEO, investor, and board member, Steve builds clever strategies, winning teams, accelerates growth, fosters strong customer relationships, and creates superior shareholder value.

His investment and exit scorecard includes raising $150m+ in capital, 5 acquisitions, and 1 IPO. He holds dual American and German citizenship with extensive knowledge of EU and APAC operations.

At TechCXO, Steve partners with CEOs, boards, and private equity firms for early and mid-stage technology companies.

He is chairman of the Cyber Threat Intelligence Network and on the advisory board for Northwestern University’s Farley Center for Innovation. He holds a BS in Marketing with a concentration in Computer and Information Technology from Miami University.

CONTACT:

https://www.linkedin.com/in/stevesubar/

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

Ep 39—Neal Miller—Decades of Financial Strategy Across 70 Companies and Still Going Nov 19, 2025

Today in the Sky Lounge, we are joined by Neal Miller, partner emeritus at TechCXO and one of the firm's earliest members. Neal shares stories from 19 years working with over 70 companies, including the legendary Cloud Sherpas journey that started with a Monday morning Starbucks meeting in 2008 and ended with an Accenture acquisition. He reveals the simple napkin drawing that transformed Boomtown from chaos to clarity, why the 1983 IPO market let an $8 million revenue company go public, and his unusual career path from KPMG auditor to software sales to CFO. Plus, hear about his transition to Costa Rica, lessons from owning a microbrewery, and why uncertain economic times actually strengthen the fractional executive model.

ABOUT OUR GUEST:

Serial technology company exec for early/mid stage technology, healthcare and healthcare tech enabled services companies.

Started career in Public Accounting at KPMG

Early career - Served as CFO of 3 public companies and 3 private/VC backed.

2006 - was 5th partner to join TechCXO (then TechCFO), roles included: Managing Partner of CFO Practice, Atlanta Geo Practice, Member of Executive Committee and Board of Managers. Have worked as a fractional exec with over 60 early stage companies, from pre-revenue to >$60M in revenue. Participated or led many capital and debt raises and several exit transactions.

Currently serve as BOD member of 2 equity backed companies

CONTACT:

linkedin.com/in/neal-miller-542642

Neal.Miller@techcxo.com

(770) 329-9069

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

Ep38-Louis Gump-Innovation, Timing, and Leadership Whether You're an Entrepreneur or Intrapreneur Oct 22, 2025

"

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

"

Ep37—Mike Martin—Big Tobacco to Government Contracts: Building Breakthrough Brand Campaigns Oct 01, 2025

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

"

Ep36—Ted Stone: Decades of Financial Strategy — Still in the Game and Giving Back Sep 17, 2025

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

Ep35 — Virginie Glaenzer: Rewriting the Rules: Growth, AI, Community, and the Meaning of Wealth Sep 03, 2025

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

Ep 34 - Brantley Fry: Why Connecting People and Process Is Your Secret Weapon Aug 20, 2025

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

Ep 33 - Alex Gafford: The 5-Hour Formula for Maximum Productivity in Minimal Time Jul 30, 2025

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

Ep32 Joe Gruca — From Pink Slip to Pivot: Predictable Sales in Unpredictable Markets Jul 09, 2025

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

Ep31 Mike Biwer—The Hidden Engine of the Economy: Unpacking the Power of Distribution with Cavallo Jun 18, 2025

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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

"

Ep30 Bob Brogan — Road Warrior to Business Architect: 40 Years of Transforming Companies Jun 04, 2025

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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

"

Ep29 Teja Yenamandra—Beyond Resumes- The Case for Talent-First, Human-Centered Hiring May 14, 2025

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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

"

Ep 28 Michael Weinstein—Tariffs and Economic Uncertainty - How We Got Here & What's Next Apr 30, 2025

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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