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.
TFTSL Ep35 – Virginie Glaenzer
Today in the Sky Lounge we are joined by Virginie Glaenzer, fractional CMO at TechCXO and author of “”The Economy of Abundance.”” From landing in Silicon Valley with four suitcases during the height of the dot-com boom to building community-driven marketing strategies that outperform traditional branding, Virginie shares insights from 25 years of digital transformation. She explains why the AI revolution exceeds the internet boom in scope, how Gen Z is rejecting traditional business models, and why the future belongs to co-creators rather than controllers. Plus hear about her minimalist lifestyle, founding the Acorn Oak women’s community, and why Dubai’s mall-centric culture shocked this world traveler.
TFTSL Ep34 – Brantley Fry
Today in the Sky Lounge we are joined by Brantley Fry, Partner at TechCXO specializing in human capital management. Brantley shares her remarkable journey from environmental lawyer working on the largest spills in US history to political service as state director for a US Senator, and eventually to the startup world where she helped navigate a successful acquisition by Quest Diagnostics. Her philosophy of being a “”connector”” between people and policy has guided every career move, and she reveals the inside story of managing culture and communication during M&A. Plus, hear about her transformative 500-mile walk across Spain on the Camino de Santiago.
Takeaways
Brantley Fry emphasizes the importance of viewing people as fuel, not friction, in business.
Her career path has been shaped by a mix of luck and preparation, often finding herself in the right place at the right time.
Effective communication is crucial in legal practice, especially during complex cases.
Brantley highlights the significance of connecting people and policy throughout her career.
She believes in the value of recruiting for culture and the importance of aligning values during mergers and acquisitions.
The healthcare sector in Birmingham is evolving, with a focus on biotech and health tech initiatives.
Brantley advocates for the need for more good people in politics to bridge divides and address common issues.
She shares insights on the challenges and opportunities in startup legal needs and the role of fractional executives.
Brantley discusses the importance of understanding the business problem when hiring and the value of non-traditional candidates.
Her experience walking the Camino de Santiago taught her about the diverse paths in life and the connections we make along the way.
TFTSL Ep 33 – Alex Gafford
Today in the Sky Lounge, we are joined by Alex Gafford from BlueStreet Capital, who’s living proof that the traditional 40-hour work week is completely broken. Alex’s company discovered something remarkable nine years ago – an asset that increased their KPIs by 24%, boosted revenue by 30%, and dramatically improved retention without costing them a penny. That asset? Time itself. Through their revolutionary five-hour workday experiment, they’ve unlocked the secret that knowledge workers can only maintain peak mental performance for about five hours max, and everything after that is just diminishing returns dressed up as “dedication.” Alex breaks down the neuroscience of ultradian rhythms, reveals why multitasking wastes 28% of your day, and explains how his team finances everything from AI infrastructure buildouts to data center expansions while working just 25 hours a week. Plus, he shares wild stories about financing raw GPUs for AI companies and why the future of work isn’t about grinding harder – it’s about being strategically smarter with your energy.