TFTSL Ep45—John Church
Today in the Sky Lounge, we are joined by John Church, lead product manager at Nethermind and adjunct professor at Duke University. John has been deep in the blockchain world since 2017 — from speculative ICOs to running treasury management for a 20,000-person decentralized autonomous organization, to now working on zero-knowledge cryptography and AI agent infrastructure.
In this conversation, John breaks down what stablecoins actually are and why their adoption matters far beyond the crypto-native crowd. He explains why Ethereum’s decentralization gives it an edge over faster competitors, and what it means that AI agents are already building wallets and executing trades on their own. He also shares his take on how he’s preparing engineering students for a world where AI compresses timelines — and creativity matters more than syntax. Plus, a survival school story from the Utah desert involving a wanted poster, stolen macaroni casserole, and a well-timed lie.
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 Ep42 — Chris Thomajan
Today in the Sky Lounge, we are joined by Chris Thomajan, a CFO who’s spent 35 years with startups and has worked with over 100 companies—mostly in biotech, mostly venture-backed, always as the steady hand while everyone else loses their minds.
Chris didn’t start in finance. English major, disco worker in London, law firm (hated it), Columbia Business School, then three decades of pattern recognition in the startup world. He’s developed a particular skill: knowing which CEOs will make it and which won’t. He’s even categorized them like wine—from Beaujolais Nouveau (enthusiastic first-timers) to Port (dictators you really don’t want to work for).
We explore what makes Boston’s biotech ecosystem unique, why nine out of ten boards need to be “managed away,” and what it really takes to prepare a company for IPO. Chris breaks down the current VC landscape (“too many capital calls, not enough distributions”), why he’d never personally invest in early-stage biotech, and the one quality that separates great CEOs from the rest: the ability to delegate.
Plus: hitchhiking 5,000 miles across America in an era when that was still possible.
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 Ep40 – Steve Subar
Today in the Sky Lounge, we are joined by Steve Subar, COO/CEO at TechCXO, who’s spent three decades building, guiding, and growing companies. His latest venture? The world’s first fully automated yoga mat cleaning machine.
It’s not exactly cocktail party material, Steve admits. But the story behind MatFresher reveals something more interesting than the product itself: what happens when an experienced founder decides to design the business model before the company.
After selling Open Kernel Labs to General Dynamics in 2012 and spending 13 years consulting for tech companies, Steve started his next venture with three non-negotiable constraints. He wanted recurring revenue. He wanted high gross margins. And he was done—completely done—with B2B sales friction. His entire career had been large systems, complex sales, long cycles. At this stage, he wanted something different.
The yoga mat problem emerged from Steve’s own 20-year hot yoga practice. Here’s a discipline built on the Sanskrit concept of Saucha (cleanliness of spirit, mind, and body), practiced on mats that smell like the inside of old hockey equipment. But before investing in product development, Steve did what experienced entrepreneurs do: he tested whether anyone actually cared.
He bought a folding table, rubber gloves, antiseptic spray from Whole Foods, and a Square reader. He showed up at yoga studios and asked people if they’d pay two bucks to get their mat cleaned. They would. But something more valuable happened during those 50-minute gaps between classes when he had nothing to do but talk to studio owners and staff.
He learned that the bigger problem wasn’t hygiene—it was unit economics. Only 10% of yoga studio operators net more than $100,000 annually. They’re not in it to get rich; they’re in it to help people. But cleanliness is the number one factor affecting their Net Promoter Score and churn rate. If Steve could reduce their labor costs while visibly improving hygiene, he’d solve two problems at once.
This is the kind of insight you can’t get from market research or surveys. “Information is not the same as wisdom,” Steve says. You can look up anything online, but “you can’t Google for experience.” True wisdom comes from combining information with experience—and that’s what leads to good decision-making.
Steve’s career bears this out. At Open Kernel Labs, his team figured out how to apply virtualization software to power-constrained devices like mobile phones. They started by targeting the most paranoid customer: the NSA. Thousands of people couldn’t bring cell phones into Fort Meade. The agency was stuck with the “ObamaBerry”—essentially two BlackBerrys glued together, one for classified and one for unclassified communications.
Open Kernel Labs became the first method for the NSA to enable standard smartphones for their employees. That stamp of approval opened commercial doors. By the time General Dynamics acquired the company, their software was in 1.6 billion phones.
Steve calls this approach “in through the out door”—finding the entrance nobody else is using. While everyone lines up at the obvious door, he looks left and right for the legitimate entrance that’s wide open but overlooked.
Now with MatFresher, he’s applying those same principles to a hardware-as-a-service business in an industry where most VCs say “we don’t do hardware.” But that’s the point. Thirty years in, Steve isn’t looking for the crowded entrance. He’s still finding out doors nobody else sees.
TFTSL Ep39 – Neal Miller
Today in the Sky Lounge, we are joined by Neal Miller, partner emeritus at TechCXO and one of the firm’s earliest members. Neal shares stories from 19 years working with over 70 companies, including the legendary Cloud Sherpas journey that started with a Monday morning Starbucks meeting in 2008 and ended with an Accenture acquisition. He reveals the simple napkin drawing that transformed Boomtown from chaos to clarity, why the 1983 IPO market let an $8 million revenue company go public, and his unusual career path from KPMG auditor to software sales to CFO. Plus, hear about his transition to Costa Rica, lessons from owning a microbrewery, and why uncertain economic times actually strengthen the fractional executive model.
TFTSL Ep38 – Louis Gump
Louis Gump joins us in the Sky Lounge to explore a question every founder and executive faces eventually: what happens after the acquisition? In this candid conversation, Louis shares how he helped build the mobile business at CNN.com, led digital transformation at The Weather Channel, and became the steady hand guiding post-acquisition innovation at startups and growth-stage companies alike.
We unpack the differences between entrepreneurs and intrapreneurs, what makes someone thrive inside a big company post-acquisition, and how timing and self-awareness shape every meaningful career move. Louis also discusses the importance of clarity in strategy, the value of not rushing change, and why keeping founders involved after a deal often leads to better outcomes.
Louis is also the author of The Inside Innovator, a practical guide to driving innovation from within established companies — ideal for leaders navigating post-acquisition roles or scaling without the founder title.
Whether you’re scaling, selling, or staying to build the next chapter — this episode will meet you at the crossroads.
TFTSL Ep37 – Mike Martin
Today in the Sky Lounge we are joined by Mike Martin, fractional CMO at TechCXO and creative veteran behind some of advertising’s most impactful campaigns. Mike shares the inside story of creating the legendary Truth anti-smoking campaign, producing million-dollar Super Bowl spots that ran only once, and why he believes vanilla content is the biggest risk brands can take. From dealing with maniacal bosses who threw storyboards down hallways to accidentally creating viral moments with ice cream trucks at elementary schools, Mike’s career spans the evolution from traditional advertising to AI-powered creativity. Plus, hear his travel adventures including swimming with 400-pound pigs in the Bahamas and getting rewarded for government success by having his program cancelled.
TFTSL Ep36 – Ted Stone
Today in the Sky Lounge we are joined by Ted Stone, a 72-year-old fractional CFO at TechCXO who’s living proof that experience beats age in the business world. Ted shares insights from four decades of private equity deals, including rollups, spinoffs, and integrations that taught him every strategy in the playbook. He explains how the “silver tsunami” of baby boomer business exits is creating unprecedented opportunities for private equity firms, why ESOPs are emerging as attractive exit strategies, and how fractional executive work lets veterans stay in the game past traditional retirement. Plus, hear his incredible travel story about surviving not one but two helicopter incidents on a single business trip.