The Revenue Dilemma

What if you were leaving 20% of your revenue on the table? Hosted by a four-time CRO Tony Capasso who has scaled growth-stage companies to $1B+, The Revenue Dilemma unpacks the hard truths behind revenue growth. The untapped opportunities, the invisible psychological roadblocks, and the real strategies that separate stalled companies from soaring ones. If you're ready to move beyond the obvious and solve the real problems blocking your next wave of growth, this podcast is for you.

The Revenue Dilemma is a business podcast hosted by Tony Capasso, with 7 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Tony Capasso hosts The Revenue Dilemma, a business show with 7 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #6

  #6: Breakthrough Brief: AI Isn’t Replacing Your Sales Team (And It Shouldn’t) with Matt Dornfeld

  Mar 5, 20269 minS1

  <p>AI SDRs are everywhere — but are they actually working? In this episode, we unpack the growing hype around AI-driven outbound sales and why simply increasing activity won’t fix a broken pipeline. Instead of replacing humans, our guest argues for augmenting them — and explains why most organizations are solving the wrong problem. From market readiness and product-market fit to messaging and data infrastructure, this conversation explores what actually drives revenue growth — and why orchestration, not automation alone, may be the real AI opportunity in sales. If you’re leading a revenue team, building AI workflows, or trying to figure out where...

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  Episode #5

  #5: The Hidden Drag on Growth No One’s Naming with Allie Garfinkle

  Feb 19, 202641 minS1

  <p>What if the biggest growth constraint in your business isn’t your product, pricing, or pipeline — but the unspoken shifts in how people work, buy, and build after Covid?</p><p>In this episode of The Revenue Dilemma, Tony sits down with Allie Garfinkle (Fortune Senior Writer) for a masterclass in perspective from one of the sharpest pattern-recognizers in tech. The conversation starts with Allie’s idea that “everyone has a grand opera inside of them” — and unpacks how deep listening, presence, and thoughtfully-applied tension can unlock truth in interviews, leadership, and company-building.</p><p><br></p><p>You’ll hear:</p><p...

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  Episode #4

  #4: Love Over Fear: Leading Through the Biggest Tech Shift with Brett A. Hurt

  Feb 12, 20261h 15mS1

  <p>In this episode, Brett A. Hurt joins us for a wide-ranging masterclass on what’s about to break in go-to-market — as AI agents begin to replace web browsers, rewrite “search,” and fundamentally change how companies reach customers.</p><p>Drawing on decades building and scaling category-defining software companies — and most recently leading data.world through its acquisition by ServiceNow — Brett explains why enterprises are stuck in fear and inertia, how to rebuild customer acquisition for an agent-driven world, and why “leading through love” is a competitive advantage in periods of massive change.</p><p>You’ll hear stories and frameworks — inclu...

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  Episode #3

  #3: The Revenue Algorithm: How Great Operators Build Enterprise Value in Software with Sam Monti

  Jan 28, 20261h 29mS1

  <p>In this episode, Sam Monti joins us for a masterclass on building enterprise value in software businesses — from scaling recurring revenue and structuring sales compensation to executing disciplined M&A and shaping high-performance cultures inside private-equity-backed companies.</p><p>Drawing on decades of operating experience across industrial, SaaS, MarTech, legal tech, and supply chain software — and leadership roles at companies like Epicor, Lithium/WP Engine, and Vista-backed platforms — Sam breaks down his simple but powerful “revenue algorithm,” explains why most companies leave millions on the table, and shares hard-earned lessons from more than 30 acquisitions.</p><p>You’ll hear stories from...

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  Episode #2

  #2: The Hidden Signals That Drive Growth with Jim Stoneham

  Jan 21, 202659 minS1

  <p>In this episode, Jim Stoneham joins us to unpack what product-led growth really looks like in practice — and where human intervention still matters most. Drawing from his experience at New Relic, Stripe, Yahoo, and now SignalFire, Jim shares how deep product instrumentation, trigger-based engagement, and focused ICPs create outsized impact across sales, marketing, and customer success. We also explore where AI is genuinely adding leverage today, how to avoid waiting for “perfect” data, and why focus — not scale — is often the missing ingredient for founders and revenue leaders.</p><p><br></p><p>You’ll hear stories from his work across...

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