Tales From The Sky Lounge-A Business Podcast

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

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

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

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

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