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 Ep43 —John Yates and Gregg Bedol
Today in the Sky Lounge, we are joined by John Yates, a partner at Gunderson-Dettmer, and Gregg Bedol, founder of TractionBD. Their collaboration represents something rare: seasoned professionals using decades of hard-won experience to build something genuinely new.
John arrived in Atlanta in 1981, the same year IBM announced the PC and opened its architecture to software developers. For 44 years, he’s represented tech companies through every stage of growth, from garage startups to some of the largest companies in the country. Gregg’s path ran through Arthur Andersen’s consulting division, executive roles in tech companies, and multiple entrepreneurial ventures. They’ve been friends and neighbors for 35 years. The driveway conversations finally led somewhere.
The problem they’re solving is as old as professional services itself. For centuries, the model has been apprenticeship: find a mentor, learn for years or decades, hope they retire and hand you their book of business. It’s slow, uncertain, and increasingly rare. “”There aren’t as many people who want to help the next generation,”” as the conversation acknowledges. Most professionals find themselves having to scramble and make their own destiny.
John’s insight, refined over four decades, comes down to a simple equation: prospects plus actions equals clients. The catch? It takes an average of 7 to 10 actions to convert a prospect into a client. Most professionals give up after two or three because they can’t think of what else to do. You can only invite someone to play golf or attend a football game so many times.
TractionBD emerged from recognizing what AI suddenly made possible. Gregg describes it as “”putting John Yates in a box””—taking expertise that previously required decades to develop and making it accessible through software. The platform is voice-enabled and mobile-first because professionals don’t want to come back to a desktop and type into a CRM. “”That’s been there for years. It’s called CRM, and it doesn’t work,”” Gregg notes.
The distinction matters. Traditional CRMs are repositories for data, designed for marketing organizations and professional salespeople. TractionBD targets professionals who don’t sell to make a living—lawyers, accountants, consultants—people who deliver a service where selling is a necessary component. The tool handles the grindy parts: scanning business cards, building ideal client profiles, suggesting contextually appropriate actions, maintaining persistence without being obnoxious.
“”Business development is not an automated process. It’s a human-to-human process,”” Gregg emphasizes. The technology accelerates and enhances, but the core hasn’t changed. It’s still about relationships. Relationships drive revenue. The difference is that AI can now help you stay top of mind with a hundred people instead of ten, and it can craft messages that sound authentic because it learns your voice over time.
The conversation extends to Atlanta’s opportunity. John is working to establish the city as a hub for Applied AI, bringing together Fortune 500 headquarters, venture capital, Georgia Tech’s research capabilities, and a mayor who cares about technology. The Southeast is probably the fastest-growing area for tech in the country, but it requires intentional community building—something John has been doing since 1981.
What makes this collaboration work is the combination of deep domain expertise with genuine technical innovation. John knows what business development requires. Gregg knows how to build it. They’re old enough to have extensive networks and young enough to be building something new. The tools available now—AI, social media, mobile platforms—create advantages that didn’t exist even two years ago. Experience finally has the edge.
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 Ep29—Teja Yenamandra
Joining us today in the Sky Lounge is Teja Yenamandra, founder of Gun.io — the dev marketplace built for engineers who don’t belong on job boards. From martial arts to macro trends, Teja breaks down why great hiring is about rhythm, not resumes; how AI is reshaping the shape of work itself; and what most startups forget after the match is made. This is a founder story built on cold calls, precision matching, and scaling trust — not headcount.
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 Ep26 – Matt Oess
“Joining us today in the Sky Lounge is Matt Oess, a seasoned leader in sales, marketing, and executive coaching at TechCXO. With over a decade of experience guiding C-suite executives, Matt shares invaluable insights on leadership coaching, AI-driven business transformation, and navigating the complexities of high-stakes decision-making.
We dive deep into AI’s game-changing potential, the evolving role of coaching in leadership, and how businesses can leverage AI for productivity, sales, and innovation. Matt also takes us behind the scenes of his work with the Krach Institute for Tech Diplomacy, where he’s helping shape global policies on emerging technologies like AI, semiconductors, and cybersecurity.
From early-stage startups to billion-dollar enterprises, Matt has seen it all. He reveals why vulnerability is a CEO’s secret weapon, how AI is revolutionizing business workflows, and why the next era of software might outgrow traditional SaaS models.
Join us for a thought-provoking discussion that bridges technology, leadership, and human potential—perfect for executives, tech enthusiasts, and emerging leaders preparing for tomorrow’s challenges.”
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 Ep24 – Alan Gold
Joining us today in the Sky Lounge is Alan Gold, a marketing and sales strategist with decades of experience in M&A, startups, and growth strategy. Alan has been on both sides of the table—helping companies scale, navigating acquisitions, and leading turnarounds. From being part of the launch team for Wi-Fi technology to working on speech recognition and AI-powered business tools, he’s seen how markets evolve and what it really takes to stay ahead.
We dive into:
M&A trends—why some companies are stuck while others are thriving
The hard truth about growth and why some businesses hit a ceiling
The real role of strategy in marketing (hint: it’s not just about SEO and PPC)
How AI is reshaping sales and marketing, and what’s next for the industry
Why most companies miss the mark when hiring sales leadership
Plus, Alan shares hilarious and wild travel stories, including a baboon with an attitude and getting detained in Colombia.
If you’re in startups, consulting, M&A, or just trying to grow a business, this one’s for you.
TFTSL Ep23 – Antonio Pagano
Joining us today in the Sky Lounge is Antonio Pagano, founder of Wawandco and co-founder of Symbol Security. Todd and Antonoio discuss the importance of cybersecurity, focusing on the human element and compliance, the evolution of phishing attacks, and the role of AI in crafting sophisticated scams. Antonio shares insights on real-world cybersecurity incidents, the trends in cyber insurance, and the dynamics of running a business with a remote co-founder. Antonio Pagano shares his journey as a founder, discussing the challenges, successes, and the constantly evolving landscape of entrepreneurship. While Antonio is always challenging himself to learn and develop new skills and understanding, he also highlights the importance of balancing ambition with personal well-being, and that a grounded approach fuels both creativity and success.
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!