Tales From The Sky Lounge-A Business Podcast

Todd Merrill
  • 5.0 (1)
  • Business
  • Updated Weekly

Welcome to Tales from the Sky Lounge, a podcast where host Todd Merrill—a veteran software engineer and founder—takes you on an intimate journey through the world of business, consulting, and venture investing. From our virtual perch high above the daily grind, we dive into candid conversations with entrepreneurs, consultants, and investors who share their battle-tested insights and untold stories from the startup trenches, offering fresh perspectives on what it takes to thrive in today's dynamic business landscape.

  1. Ep 48 Kumar Ampapathini: What Builders Get Wrong About Capital—From Someone Who's Lived Both Sides

    May 13

    Ep 48 Kumar Ampapathini: What Builders Get Wrong About Capital—From Someone Who's Lived Both Sides

    Today in the Sky Lounge, we are joined by Kumar Amapathini, fractional CFO and Tech CXO partner with over 25 years spanning Cisco engineering, Merrill Lynch investment banking, JP Morgan, and Guggenheim Partners. Kumar started as a software developer watching Cisco make billion-dollar acquisitions he couldn't fully decode — not because the technology was over his head, but because the business logic was. That gap sent him to the University of Chicago for an MBA and into a finance career that eventually took him back to the startup world he'd left behind. Today he serves growth-stage companies as a fractional CFO, bringing Wall Street-level deal experience to founders who need it most before they can afford it full-time. He walks through what institutional investors actually want to see — and why it's usually not what founders think — unpacks the M&A process behind the Schedule City acquisition by Vagaro in October 2024, and makes the case that the highest bidder almost never wins a deal. He also shares the """"corporate athlete"""" approach that keeps him sharp across a full client travel schedule — including the food poisoning lesson that permanently ended his airport culinary experiments. ABOUT OUR GUEST: Kumar Ampapathini is a TechCXO Partner and experienced finance executive who serves clients as C-Suite / Board advisor and an interim and fractional CFO. Kumar manages all financial aspects of his clients’ businesses, including Capital / Revenue Planning, Fundraising, Cap Table Management, Contract Negotiation, FP&A, Strategy, M&A, Audit, Dashboards / Scorecards, Investor Reporting, Payroll, and Taxes. Kumar’s select current and past clients include Wabbi (Cyber Security, SaaS), Security Journey (SaaS), Schedulicity (fintech, SaaS), MobileWalla (DaaS, SaaS), Delve (Software, Advertising), Pison Technology (Software / Hardware), Pippin Title (fintech, SaaS), GoodUnited (tech, SaaS), Nav.it (fintech, SaaS), Ness (Credit Card), Families in Transition (non-profit), Our Village United (non-profit), genrae (crypto), GeoXEnergy (Geothermal), etc. CONTACT: LinkedIn: https://www.linkedin.com/in/kumar-ampapathini-cpa-mba-063375/ 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

    1h 4m
  2. Ep 47 Karen Rands—The Compassionate Capitalist: Inside Secrets to Angel and Crowdfund Investing

    May 1

    Ep 47 Karen Rands—The Compassionate Capitalist: Inside Secrets to Angel and Crowdfund Investing

    Today in the Sky Lounge, we are joined by Karen Rands, founder of the Compassionate Capitalist Movement and author of Inside Secrets to Angel Investing and Inside Secrets to Crowdfund Investing. Karen spent years at IBM navigating the transition from mainframe dominance to distributed computing — watching Dell, Compaq, and Apple take market share from a company that assumed loyalty was permanent. That front-row seat to corporate stagnation shaped everything that came after: a pivot into intrapreneurship, a failed dot-com-era fundraising run that introduced her to angel investing, and a moment in a parking deck outside an Atlanta investor meeting where she found her calling with goosebumps. She took over a nearly-defunct angel group — discovered the membership was largely fictitious and the revenue model nonexistent — rebuilt it into one of the top 50 most active angel networks in the U.S., and has spent the years since solving the one problem nobody else is tackling: most people who have the means to be angel investors have never heard the term. Karen and Todd dig into why the angel investing model hasn't been innovated since the 1980s, what revenue share financing unlocks for Main Street businesses that VCs will never touch, and why AI is finally making Karen's long-held vision of a digital investor education platform actually executable. Plus: the snowstorm, the last flight out of LaGuardia, and what happens when IBM opens the bar mid-circle over Hartsfield. ABOUT OUR GUEST: Karen Rands, founder of the Compassionate Capitalist™ Movement, is a nationally recognized thought leader on angel and crowdfund investing. A former IBM innovator and past Managing Director of a leading angel group, she has spent 20+ years advising entrepreneurs and guiding investors. As the author of two books as part of the 'Inside Secrets' Series about Angel and Crowdfund Investing, host of the top rated podcast The Compassionate Capitalist Show, and creator of The Compassionalist Academy™; a digital on demand training platform for learning how to be angel / crowdfund investors, Karen inspires and equips people to build wealth by investing in private businesses, fund innovation and share in the success of those founders' businesses. All of her links to books, podcast, academy, free resources and social links are available at http://bit.ly/linkCCS. CONTACT: http://bit.ly/linkCCS 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. 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

    1h 19m
  3. Ep 46 Rachel Zeller of Kitces.com—Hiring Humans in an AI World

    Apr 15

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

    Today in the Sky Lounge, we are joined by Rachel Zeller, Managing Director and Integrator at Kitces.com, the leading education and resource platform for financial advisors. Rachel started as a virtual bookkeeper doing five hours a month for founder Michael Kitces in 2006 — before remote work was a thing anyone took seriously. Nine years later, he asked her to drop every other client and come run the operation full-time. The job description was essentially: "I have no idea what it's going to look like, but it's going to be so much fun." In this conversation, Rachel walks through what happened when Kitces doubled its staff in 2021, how she built systems while the plane was already in the air, and why she now requires candidates to submit their AI transcript alongside their work sample. She talks through the candidate whose eyes kept going up and to the right mid-interview, why she turned off LinkedIn Easy Apply, and what """"culture fit every time, flat out"""" actually means in practice. Plus: what she's coaching her college-age son to develop that no AI can replicate."" ABOUT OUR GUEST: With a background in counseling and a love of spreadsheets and project management, I have found a role that allows me to lean into those skills simultaneously. My time as Managing Director is split between executing company strategy and overseeing the projects that roadmap towards those goals and ensuring my Team has everything they need to be their best selves at work. CONTACT: LinkedIn: https://www.linkedin.com/in/rachel-zeller-51013656 Email: rachel@kitces.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

    44 min
  4. Ep45 John Church: Crypto Grows Up: Building at the Intersection of Blockchain and AI

    Mar 11

    Ep45 John Church: Crypto Grows Up: Building at the Intersection of Blockchain and AI

    Today in the Sky Lounge, we are joined by John Church, lead product manager at Nethermind and adjunct professor at Duke University. John has been deep in the blockchain world since 2017 — from speculative ICOs to running treasury management for a 20,000-person decentralized autonomous organization, to now working on zero-knowledge cryptography and AI agent infrastructure. In this conversation, John breaks down what stablecoins actually are and why their adoption matters far beyond the crypto-native crowd. He explains why Ethereum's decentralization gives it an edge over faster competitors, and what it means that AI agents are already building wallets and executing trades on their own. He also shares his take on how he's preparing engineering students for a world where AI compresses timelines — and creativity matters more than syntax. Plus, a survival school story from the Utah desert involving a wanted poster, stolen macaroni casserole, and a well-timed lie. ABOUT OUR GUEST: John Church is a Lead Product Manager at Nethermind, specializing in enterprise blockchain solutions, cryptography, and digital assets. Currently serving as an Adjunct Professor at Duke University Pratt School of Engineering, John teaches Fintech with a focus on blockchain. Previously, they held the role of Director of Product Management at Bankless Consulting, providing oversight on web3 projects. With over 20 years of experience in technology implementations and project management, they have contributed significantly to the field, including as a core contributor to BanklessDAO and a proud validator of Ethereum since 2020. CONTACT: LinkedIn: https://www.linkedin.com/in/john-a-church/ 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

    57 min
  5. Ep44 Niral Shah: A Trauma Surgeon & Entrepreneur Talks Healthcare, AI and What’s Next

    Feb 25

    Ep44 Niral Shah: A Trauma Surgeon & Entrepreneur Talks Healthcare, AI and What’s Next

    Today in the Sky Lounge, we are joined by Niral Shah — trauma surgeon, serial entrepreneur, and one of the more unusual career arcs you're likely to hear about. Niral started medical school at 19, paused to build a search engine in Silicon Valley during the dot-com boom, went back to finish his MD, became a trauma surgeon, and then in 2018 decided healthcare was headed for a reckoning and he needed a seat at that table. This conversation covers a lot of ground. Niral talks about pitching Nokia Ventures without a deck — and not even knowing he was going to pitch. He walks through why he chose Chapter 7 over keeping the cash when his first company ran out of road, and what that decision meant for his reputation with investors. On healthcare, he's direct: the U.S. spends 18-21% of GDP on it and gets outcomes roughly equivalent to Albania. He explains where the fat actually is, why the end user and the buyer are almost never the same person in healthcare, and where he thinks entrepreneurs should be focusing right now. Plus, his wife's very unexpected airport lounge conversion story. ABOUT OUR GUEST: Niral Shah, MD MBA FACS is triple-board certified in Surgery and Critical Care by the American Board of Surgery. A serial surgeon-entrepreneur with unique vantage at the intersection of medicine, innovation and entrepreneurship successfully launching and scaling early-stage technology and life science companies. Having founded and exited two companies and advised a number of others, Niral brings a proven track record of translating clinical insight into commercial success and guiding startup teams from ideation through exit. He received his MBA from the University of Michigan - Ross School of Business and he was awarded the C.K. Prahalad Initiative Fellowship to evaluate new models focusing on healthcare for the “Bottom of the Pyramid” and transferability to developed countries. He continues with various humanitarian causes even going into hotspots when needed such as Haiti with the United Nations Stabilization Mission and was the course lead for trauma surgery on behalf of the Harvard Humanitarian Initiative and the International Medical Corps in Mykolaiv Oblast, Ukraine. In his free time, he enjoys golfing, skiing, fishing, and spending time with his family. CONTACT: LinkedIn: www.linkedin.com/in/niral-shah-md-mba Contact info 617-544-7428; niralshah.md@gmail.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. As a C-Level executive, 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

    1h 2m
  6. Ep43 John Yates and Gregg Bedol—How 2 Industry Veterans Are Solving Business Dev with TractionBD

    Feb 9

    Ep43 John Yates and Gregg Bedol—How 2 Industry Veterans Are Solving Business Dev with TractionBD

    Today in the Sky Lounge, we are joined by John Yates and Gregg Bedol. John has spent 44 years representing tech companies in Atlanta, starting in 1981 when IBM opened up the PC architecture—literally the beginning of time for the tech community. Gregg has been in consulting since the Arthur Andersen days and is now a serial entrepreneur on his latest venture. The conversation centers on their collaboration building TractionBD, a platform that takes John's four decades of business development expertise and makes it accessible through AI. They break down why most professionals fail at business development—it takes 7 to 10 touches to convert a prospect, but most give up after two or three. The solution isn't just about automation; it's about making those touches authentic, timely, and impossible to forget. John and Gregg also discuss Atlanta's opportunity to plant a flag in Applied AI, the evolution from business cards in coat pockets to voice-enabled relationship management, and why the traditional mentorship model for professionals is being compressed from decades into days. Plus, travel stories involving conference calls on Italian mountainsides and horse-drawn wagons at India's largest toll booth. ABOUT OUR GUESTS: John Yates John Yates is a partner at Gunderson Dettmer with over 40 years representing tech companies and investors throughout the Southeast as a recognized leader in the field of technology law. He co-founded several influential Atlanta organizations including the Southeastern Software Association, Technology Association of Georgia, Tech Executives Roundtable, and Tech Leaders Forum. A sought-after speaker, John has delivered 250+ presentations at events hosted by organizations like the American Bar Association. His contributions to Atlanta's tech community have earned him recognition as one of Atlanta's ""Most Influential Leaders,"" the Technology Association of Georgia's ""Leader of Influence Award,"" and induction into the Computer Museum of America's Hall of Fame. He also serves on the boards of Duke Law School and Furman University. Gregg Bedol Gregg Bedol is a technology executive, entrepreneur, and advisor with over forty years of experience in enterprise software, professional services, and consulting. He has worked both inside established organizations and as an independent consultant, delivering complex, long-running engagements. That experience gave him a clear view into how professional services really operate—where time goes, how follow-up breaks down, and why business development often becomes uneven even for capable professionals. Gregg is known for a practical, systems-oriented approach. He focuses on how incentives, tools, and workflows shape behavior over time. Today, he is Co-Founder and CEO of TractionBD, where he applies those lessons to building tools that support consistent execution without adding unnecessary overhead or sales pressure. CONTACT: John Yates https://www.linkedin.com/in/johncyates/ Gregg Bedol https://www.linkedin.com/in/greggbedol/ Find out what SUMMIT is from episode 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. 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

    1h 4m
  7. Ep42 Chris Thomajan: Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners

    Jan 21

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

    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

    53 min
  8. Ep41 Bryan Dennstedt of AIWithBry—2026 Trends: Trust in AI, Healthcare, College, AGI & more

    12/31/2025

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

    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

    1h 1m
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About

Welcome to Tales from the Sky Lounge, a podcast where host Todd Merrill—a veteran software engineer and founder—takes you on an intimate journey through the world of business, consulting, and venture investing. From our virtual perch high above the daily grind, we dive into candid conversations with entrepreneurs, consultants, and investors who share their battle-tested insights and untold stories from the startup trenches, offering fresh perspectives on what it takes to thrive in today's dynamic business landscape.

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