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 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 Ep22 – Bryan Dennstedt
Today in the Sky Lounge, Bryan Dennstedt joins Todd Merrill as they bring their unique perspectives from years in business, technology, and investing for a deep dive into the trends that will shape 2025. From venture capital’s cautious return to the AI-driven reshaping of industries, this episode is a candid discussion about what’s next for tech, work, and investing. Everything from whether AI is going to hit speed bumps or keep climbing, blockchain’s role in authenticity in AI and the future of collaboration tools is on the table!
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.