Ep 50 - Kirby Winters —Parallel Entrepreneurism: Shipping Startups Side by Side

Ep 50 - Kirby Winters —Parallel Entrepreneurism: Shipping Startups Side by Side

Today in the Sky Lounge, we are joined by Kirby Winters — a returning guest and a self-described multipreneur running several companies at the same time. Most founders build one thing and give it everything. Kirby's bet is different: when AI compresses the build cycle from years to months, you can run companies in parallel. He and Todd get into why that's suddenly viable — and what it actually takes to hold three (and more) ventures in your head at once. The anchor is Cyber Savi, the compliance firm he built after walking away from consulting six months ago, now up to seven tools. But the same velocity that let him ship those tools also powers the others: Literally Vodka, a celiac-friendly brand born from his wife's search for something sippable and gluten-free, now expanding across the Southeast; and Unshucked, an app for tracking and rating oysters by origin and salinity. Along the way: why knowledge stopped being worth selling, the """"AI DR"""" problem nobody's planning for, and a bucket-list parachute landing at a beach bar. ABOUT OUR GUEST: Kirby Winters has been a lifelong student of technology, immersing himself in the field for decades. His career began in the wireless industry with GTE Wireless, where he gained diverse experience in roles ranging from marketing manager to database administrator. He then transitioned to the internet sector, launching Winter Media, a consultancy for new internet ventures and software development. In 1999, he co-founded Solar Velocity, a full-service interactive marketing firm he led for over a decade before selling the company in 2011. Kirby joined TechCXO at the end of 2015, where he contributed to their team of C-level professionals providing fractional services to organizations nationwide. Beyond his primary work, he has been an active investor and advisor in the startup ecosystem, serving on the Board of Advisors for the legal video advice platform LawTake and acting as a founding member and head of technology for the live-streaming event company CrowdCams. He maintains a strong interest in supporting dynamic, early-stage companies with significant potential. CONTACT: https://www.linkedin.com/in/kirbywinters Learn more: https://cybersavi.com/ https://literallydrink.com/about-us/ https://unshucked.co/ 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 49—Jen Bonnett - The CEO Is The Salesperson: Why Founders Can't Just Hand Off the Pitch

Today in the Sky Lounge, we are joined by Jennifer Bonnett — a longtime Atlanta tech entrepreneur who coded a search engine called eTour.com in 1997, five years before Google existed, and rode it to one of the most-trafficked websites in the world. After years building Georgia's startup ecosystem at ATDC, the Savannah Economic Development Authority, and Invest Atlanta's Women's Entrepreneurship Initiative, she's done something deliberate: walked away to spend the summer ""playing with AI."" This conversation moves fast across what's actually changing. Jen explains how she sold a no-AI city government on its first pilots, why she runs a Hermes agent that drafts her email every morning but never hits send, and the moment her voice-controlled recipe app jumped ahead because someone across the kitchen said ""next."" She and Todd map out a $30K model for starting companies in an era where software is cheap — and why the CEO still has to be the one selling. Plus: the real case for co-founders, why fewer than 2% of venture capital reaches women, and the three cities Jen has called home. ABOUT OUR GUEST: Jennifer Bonnett transforms ideas into impact. A Technology Executive and Startup Ecosystem Developer with over two decades in software development and IT management, she's built a career on empowering entrepreneurs and fostering disruptive innovation — because in every founder's dream, she sees a milestone for the industry. Her track record spans turning a struggling non-profit into a thriving hub, relocating tech firms, and pioneering programs like the Savannah Logistics Innovation Center, alongside championing women's entrepreneurship through StartupChicks. Today she's most intrigued by AI, Fintech, and Sustainable Tech — always watching for trends that serve a broader societal benefit. CONTACT: Linkedin: https://www.linkedin.com/in/jenniferbonnett/ 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 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