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.
Tales From The Sky Lounge
Claim This Podcastby Todd Merrill
52 episodes
Updated Weekly
Accepts GuestsHas SponsorsLocation 🇺🇸
42
Podcast Authority
BetaFairBased on show quality, social media presence, reviews, charts, and more
Quality37
Social90
YouTube72
Engagement0
Podcast Overview
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.
Language
🇺🇲
Publishing Since
2/9/2024
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42
Podcast Authority
BetaFairBased on show quality, social media presence, reviews, charts, and more
Quality37
Social90
YouTube72
Engagement0
6
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11
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excellent
Episode Length
57 minutes
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good
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3.0/5
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Recent Episodes
June 24, 2026
Ep 49—Jen Bonnett - The CEO Is The Salesperson: Why Founders Can't Just Hand Off the Pitch
Host Todd Merrill interviews Technology Executive Jennifer Bonnett about why founders must lead sales efforts, even with AI advancements, to drive startup success.
May 13, 2026
Ep 48 Kumar Ampapathini: What Builders Get Wrong About Capital—From Someone Who's Lived Both Sides
<p>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.</p><p>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.</p><p>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.</p><p>ABOUT OUR GUEST: </p><p>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.</p><p>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.</p><p>CONTACT:</p><p>LinkedIn: https://www.linkedin.com/in/kumar-ampapathini-cpa-mba-063375/</p><p>What is THE SKY LOUNGE?</p><p>Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.</p><p>ABOUT OUR HOST:</p><p>Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.</p><p>He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.</p><p>Subscribe and turn on notifications to listen to new episodes as they launch!</p><p>YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6</p><p>Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN</p><p>Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658</p><p>Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge</p><p>Follow Tales From The SkyLounge on Social Media</p><p>X/Twitter: https://x.com/TFTSkyLounge</p><p>Instagram: https://www.instagram.com/tftskylounge/</p><p>Learn more about TechCXO: https://www.techcxo.com/</p><p>Production/Design: James Liebman</p><p>Music: Soundstripe/Cody Martin-Sunrise</p>
May 1, 2026
Ep 47 Karen Rands—The Compassionate Capitalist: Inside Secrets to Angel and Crowdfund Investing
<p>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.</p><p>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.</p><p>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.</p><p>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.</p><p>ABOUT OUR GUEST: </p><p>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.</p><p>All of her links to books, podcast, academy, free resources and social links are available at http://bit.ly/linkCCS.</p><p>CONTACT:</p><p>http://bit.ly/linkCCS</p><p>What is THE SKY LOUNGE?</p><p>Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.</p><p>ABOUT OUR HOST:</p><p>Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO.</p><p>He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.</p><p>Subscribe and turn on notifications to listen to new episodes as they launch!</p><p>YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6</p><p>Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN</p><p>Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658</p><p>Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge</p><p>Follow Tales From The SkyLounge on Social Media</p><p>X/Twitter: https://x.com/TFTSkyLounge</p><p>Instagram: https://www.instagram.com/tftskylounge/</p><p>Learn more about TechCXO: https://www.techcxo.com/</p><p>Production/Design: James Liebman</p><p>Music: Soundstripe/Cody Martin-Sunrise</p>
52 total episodes available with 16 transcripts
Deep-dive analytics for Tales From The Sky Lounge
Frequently asked questions
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- What is Tales From The Sky Lounge?
- How often does this podcast release new episodes?
This podcast updates weekly.
- Where can I listen to this podcast?
This podcast is available on 7 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
No, this podcast does not typically feature guests.
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