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 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 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 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.