TFTSL Ep44—Niral Shah
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.
TFTSL Ep41 — Bryan Dennstedt of AIwithBry
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.
TFTSL Ep32 – Joe Gruca
“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.
TFTSL Ep30 – Bob Brogan
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.
TFTSL Ep28 – Michael Weinstein
“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.
TFTSL Ep27 – Jeff Haynie
Joining us today in the Sky Lounge is tech entrepreneur and innovation veteran Jeff Haynie, co-founder of Appcelerator and now founder of Agentuity, a startup building a next-gen cloud platform for AI agents.
Jeff takes us deep into the early days of mobile development—before React Native, before Node.js—and the wild ride of launching Titanium, an open-source mobile framework that scaled to millions of developers. From those Silicon Valley go-go years to today’s decentralized future, Jeff shares startup lessons, hard-won insights, and where he sees the future of AI development going next.
TFTSL Ep25 — Lisa Calhoun
“Joining us in the Sky Lounge today is Lisa Calhoun, founding managing partner of Valor Ventures! Lisa shares her journey as a fourth-generation entrepreneur, the importance of relationships in venture capital, and her investment philosophy. She and Todd discuss the current state of the venture landscape, the impact of AI on startups, and advice for young entrepreneurs. Lisa shares her insights on navigating challenges in the industry and the transformative power of travel and personal growth.
Growing up, working for her family’s commercial print shop, cold-calling clients as a teenager, and witnessing the rise of the microcomputer revolution firsthand, Lisa’s got a lot of experience with making things happen in the tech industry. She explains how those experiences shaped her investing philosophy at Valor, where she leads seed-stage AI and SaaS deals across the South.
TFTSL Ep21 — James Rozich
In this episode of Tales from the Sky Lounge, Todd Merrill speaks with Adam Lehde, co-founder of Happen Technologies, about his journey in building a hybrid software development team that leverages talent from Ukraine. They discuss the cultural differences encountered while working with Ukrainian developers, the impact of remote work dynamics post-COVID, and the potential for a thriving startup culture in Ukraine as the country looks towards recovery from conflict. In this conversation, Adam Lehde shares his journey through mobile development, the challenges of cross-platform technology, and the importance of user engagement in apps. He discusses the balance between family and career, his transition to entrepreneurship, and how fitness plays a crucial role in managing stress. Adam also reflects on his travel experiences and the cultural insights gained along the way, emphasizing the value of community and personal growth.
TFTSL Ep20 — Adam Lehde
In this episode of Tales from the Sky Lounge, Todd Merrill speaks with Adam Lehde, co-founder of Happen Technologies, about his journey in building a hybrid software development team that leverages talent from Ukraine. They discuss the cultural differences encountered while working with Ukrainian developers, the impact of remote work dynamics post-COVID, and the potential for a thriving startup culture in Ukraine as the country looks towards recovery from conflict. In this conversation, Adam Lehde shares his journey through mobile development, the challenges of cross-platform technology, and the importance of user engagement in apps. He discusses the balance between family and career, his transition to entrepreneurship, and how fitness plays a crucial role in managing stress. Adam also reflects on his travel experiences and the cultural insights gained along the way, emphasizing the value of community and personal growth.
TFTSL Ep19 – Kathryn O’Day
Joining us today in the Sky Lounge is Kathryn O’Day, entrepreneur and partner at Atlanta Ventures. Kathryn shares her journey of building multiple successful startups and being a major part of massive acquisitions. We dive deep into the parallels between endurance sports and entrepreneurship, uncovering how triathlon training taught her key lessons in consistency, grit, and pushing through difficult times.
Kathryn also reveals key insights into startup culture, highlights how Atlanta Ventures finds and molds startups to be their best selves and shares the value of being “positive, supportive, and self-starting”—qualities that shaped her experience at Pardot and beyond. We explore the importance of confidence, especially for women in tech, and discuss why being nice can be a superpower in business.