Why Most Companies Are Pricing Wrong: The Hidden System Behind Google's Million Daily Price Changes with Gary Bailey

Why Most Companies Are Pricing Wrong: The Hidden System Behind Google's Million Daily Price Changes with Gary Bailey

Gary Bailey is the founder at The Talent Capitalist, where he teaches monetization as a discipline, and serves as a finance and monetization consultant at FinTech Strategic Advisors.

With a background that spans from banking and derivatives pricing in the 1990s to coaching the rise of AI monetization product managers today, Gary brings a unique perspective to value capture and pricing strategy.

In this episode, Gary shares his insights on the distinction between pricing and monetization, drawing from his experience pricing hundreds of thousands of different financial instruments to help modern AI companies think about value capture. He explores the controversial topic of contextual pricing - why companies like Google and Facebook price millions of micro-transactions differently based on context, time, and user behavior.

Together with Mark, they dive deep into the Jobs-to-be-Done framework, debate whether it's different from problem-solution thinking, and tackle the thorny issue of when dynamic pricing crosses the line from smart segmentation to sleazy manipulation.

Why you have to check out today's podcast:

  • Learn the difference between pricing and monetization, and why value capture is the real game-changer for sustainable business growth.
  • Discover how AI companies can price thousands of different use cases without overwhelming customers or appearing manipulative.
  • Understand when contextual pricing is smart segmentation versus when it becomes unethically sleazy.

"Hire a pricing person, and that's it really, because they're going to throw some things that you hate, throw some things that you like in the same way that you wouldn't ordinarily try and clear your drain all the time on your own. Why would you not [have] someone clear your pricing issues?"

– Gary Bailey

Topics Covered:

01:32 – From banking derivatives to AI: Gary's pricing journey through 100,000+ financial instruments

03:28 – Monetization vs. Pricing: Why value capture matters more than price points

06:26 – The Jobs-to-be-Done debate: Are foundational problems the same as jobs?

12:14 – The umbrella test: Distinguishing core jobs from feature-level problems

15:32 – Why SaaS companies struggle: The 10,000 use cases pricing challenge

16:48 – Google and Facebook's secret: Pricing millions of micro-transactions contextually

18:00 – The factorial complexity problem: When features create exponential pricing opportunities

21:30 – When pricing becomes sleazy: The ethics of contextual price discrimination

23:27 – Airlines and Amazon: When dynamic pricing crosses the line

25:52 – AI for strategic moats: How Gary helps founders identify key monetization metrics

29:09 – Using AI as a pricing sounding board: Context + diagrams = better insights

30:19 – Final advice: Why every company needs a pricing person

Key Takeaways:

"Monetization is really how much of the value that you create are you capturing, and what is the system behind you consistently capturing that value." – Gary Bailey

"Most of the companies that we know, startups that talk about generating revenue, but very few talk about value capture." – Gary Bailey

"In reality, the most optimal pricing would be to price every single one of those problems individually." – Gary Bailey

"When it gets scammy... I think in some of the healthcare stuff, the PBM stuff and some of the other things do I think, well, that's a little bit risky with healthcare and stuff, but I think people are used to it because they experience it in everyday life." – Gary Bailey

Resources and People Mentioned:

Connect with Gary Bailey:

Connect with Mark Stiving:

Jaksot(300)

Blogcast: Tariffs Are a Second Chance

Blogcast: Tariffs Are a Second Chance

This is an Impact Pricing Blog published on April 7, 2025, turned into an audio podcast so you can listen on the go. Read Full Article Here: https://impactpricing.com/blog/tariffs-are-a-second-chance/ If you have any feedback, definitely send it. You can reach us at mark@impactpricing.com.  Now, go make an impact.   Connect with Mark Stiving: Email: mark@impactpricing.com LinkedIn: https://www.linkedin.com/in/stiving/

6 Kesä 2min

Stop Pricing Like Everyone Else: How to Become 10X More Expensive Than Your Competitors with Alastair Dryburgh

Stop Pricing Like Everyone Else: How to Become 10X More Expensive Than Your Competitors with Alastair Dryburgh

Alastair Dryburgh is the Chief Pricing Architect at Intelligent Pricing Architecture and the author of the book “Pricing Genius.” With a background in commercial direction for a marketing consultancy in the pharmaceutical industry, Alastair has spent years honing his expertise in pricing strategies, particularly for creative agencies and consultancies. He believes in the power of value capture and the importance of differentiation in a competitive market. In this episode, Alastair shares his insights on the significance of value over pricing, the necessity of focusing on unique offerings, and how consultants can effectively communicate their value to clients. Together, they discuss the challenges of pricing in a crowded marketplace and the impact of AI on consulting practices.   Why you have to check out today’s podcast: Discover how to capture value effectively in your pricing strategies. Learn the importance of differentiation in a competitive consulting market. Explore the relationship between pricing, value, and client outcomes.   “Consider seriously the possibility that you are ten times as good as your competitors in at least part of what you do, and you should not rest until you have found a way of getting paid in accordance with that.” – Alastair Dryburgh   Topics Covered: 01:16 – Meet Alastair Dryburgh, a pricing expert with a unique background in the pharmaceutical industry. 01:55 – Discover the pivotal moment in the pharmaceutical sector that reshaped Alastair's career. 05:22 – Learn why successful pricing hinges on value capture rather than value creation. 05:52 – Understand the oxygen vs. coffee analogy that clarifies the pricing dilemma. 07:37 – Explore the consultant's dilemma of "Will I" vs. "Which one" decisions. 09:33 – Find out why many consultants appear the same and how to differentiate yourself. 11:04 – Uncover the proprietary process strategy inspired by McKinsey that can set you apart. 13:45 – Understand why specialization simplifies your business and enhances your appeal. 16:43 – Learn how to position yourself as the only choice for potential clients. 24:17 – Examine the impact of the AI revolution on consulting pricing models. 28:18 – Get final advice on recognizing and leveraging your 10x advantage in the market.   Key Takeaways: "It's about value capture, not value creation - you may be creating vast amounts of value but capturing only a tiny fraction of it." – Alastair Dryburgh "Every time I got more specialist, things got easier - your marketing becomes clearer and clients know immediately if they're your target." – Alastair Dryburgh "If you're using AI to reduce costs with a cost-plus pricing model, it will kill you - you're just saving your way out of business." – Alastair Dryburgh   Resources and People Mentioned: Intelligent Pricing Architecture: https://www.linkedin.com/company/intelligent-pricing-architecture/  Pricing Genius (book): https://www.amazon.com/Pricing-Genius-Getting-Properly-Advice/dp/1908770783 McKinsey & Co.: https://www.mckinsey.com/    Connect with Alastair Dryburgh: LinkedIn: https://www.linkedin.com/in/alastairdryburgh/  Free resource: http://alastairdryburgh.com/guide/   Connect with Mark Stiving: LinkedIn: https://www.linkedin.com/in/stiving/ Email: mark@impactpricing.com

2 Kesä 30min

Blogcast: Price Segmentation at National Parks

Blogcast: Price Segmentation at National Parks

This is an Impact Pricing Blog published on March 31, 2025, turned into an audio podcast so you can listen on the go. Read Full Article Here: https://impactpricing.com/blog/price-segmentation-at-national-parks/ If you have any feedback, definitely send it. You can reach us at mark@impactpricing.com.  Now, go make an impact.   Connect with Mark Stiving: Email: mark@impactpricing.com LinkedIn: https://www.linkedin.com/in/stiving/

30 Touko 3min

Adoption Over Retention: The New AI Pricing Game with Marcos Rivera

Adoption Over Retention: The New AI Pricing Game with Marcos Rivera

Marcos Rivera is the founder of Pricing I/O and author of "Street Pricing." He brings 25 years of pricing experience, including a three-year tenure as an operating executive at Vista Equity Partners where he worked on pricing strategies across multiple portfolio companies. He's been running Pricing.io since 2019 and is passionate about the intersection of pricing and AI. In this episode, Marcos shares his insights on the evolving landscape of pricing in the age of AI, the importance of capturing value, and how companies can differentiate themselves in a competitive market. Together, they discuss the shift from traditional pricing models to outcome-based pricing and the role of AI in enhancing pricing strategies.   Why you have to check out today’s podcast: Discover how AI is changing the pricing landscape and what it means for businesses.  Explore the relationship between pricing, value, and customer outcomes. Learn about the importance of low-friction entry points in pricing strategies.   “AI forces you to walk the walk versus talk the talk.” – Marcos Rivera   Topics Covered: 02:48 – The evolution of pricing in SaaS where the system gets credit for capturing more value using AI. 05:36 – The significance of capturing value quickly and efficiently. 08:09 – Differentiation in a competitive market and the role of pricing power. 12:16 – The importance of entry points and reducing friction for customers. 14:44 – How product design and pricing design are interconnected. 17:07 – The challenges of pricing in the AI landscape. 18:59 – Marcos's approach to using AI in pricing strategies. 28:56 – Pricing advice from Marcos.   Key Takeaways: “Pricing is about capturing value, and AI opens up new opportunities for that.” – Marcos Rivera  “Entry points matter; make them as low friction as possible.” – Marcos Rivera  “Understanding how to differentiate your offering is crucial in a crowded market.” – Marcos Rivera   People and Resources Mentioned: Steven Forth: https://impactpricing.com/podcast/691-pricing-in-the-agent-economy-the-future-beyond-subscriptions-with-steven-forth/ Vista Equity Partners: https://www.vistaequitypartners.com/ Pricing.io: https://www.pricingio.com/ Finn AI: https://www.glia.com/ Zendesk: https://www.zendesk.com/ Cursor: https://www.cursor.com/ HubSpot: https://www.hubspot.com/ Salesforce: https://www.salesforce.com/ Snowflake: https://www.snowflake.com/en/ Netflix: https://www.netflix.com/ Slack: https://slack.com/ 99designs: https://99designs.com/ DeepSeek: https://www.deepseek.com/en ChatGPT: https://openai.com/ Claude: https://claude.ai/ Grok: https://grok.com/ Perplexity: https://www.perplexity.ai/   Connect with Marcos Rivera: LinkedIn: https://www.linkedin.com/in/marcoslrivera/ Website: https://www.pricingio.com/    Connect with Mark Stiving: LinkedIn: https://www.linkedin.com/in/stiving/  Email: mark@impactpricing.com

26 Touko 31min

Blogcast: Reasons Why B2B Salespeople Discount

Blogcast: Reasons Why B2B Salespeople Discount

This is an Impact Pricing Blog published on March 24, 2025, turned into an audio podcast so you can listen on the go. Read Full Article Here: https://impactpricing.com/blog/reasons-why-b2b-salespeople-discount/ If you have any feedback, definitely send it. You can reach us at mark@impactpricing.com.  Now, go make an impact.   Connect with Mark Stiving: Email: mark@impactpricing.com LinkedIn: https://www.linkedin.com/in/stiving/

23 Touko 3min

Pricing in the Agent Economy: The Future Beyond Subscriptions with Steven Forth

Pricing in the Agent Economy: The Future Beyond Subscriptions with Steven Forth

Steven Forth is the Co-founder & CEO of Ibbaka and a recognized expert in generative AI in pricing. With extensive experience in the intersection of artificial intelligence and pricing strategies, provides valuable insights into how agents are transforming the pricing landscape. In this episode, Steven discusses the concept of AI agents, their role in pricing, and how they can deliver value in various contexts. Together, they explore the implications of AI-driven agents on user interfaces, pricing strategies, and the future of business interactions.   Why you have to check out today’s podcast: Understand what agents are and how they differ from general-purpose AI. Discover how pricing strategies for agents can be structured around value delivery. Learn about the future of agent-to-agent interactions and their impact on pricing.   “Understanding what job your agent is going to do is critical for pricing.” – Steven Forth   Topics Covered: 02:07 – Definition of agents and their functionality.  03:17 – Differences between agents and general-purpose AI like ChatGPT.  05:11 – User interface simplicity and complexity in agent design. 08:16 – The AI agent layer cake and its implications for pricing.  11:12 – Access and usage-based pricing for agents.  14:03 – Outcomes-based pricing and its challenges.  16:16 – Tokenization. 20:27 – The importance of understanding the job an agent performs for pricing.  24:31 – Steven’s insights on the evolving landscape of pricing strategies. 31:28 – Steven’s pricing advice around agents. 31:53 – How to connect with Steven.   Key Takeaways: “Agents make it easier to do things, and if those things are valuable, we’re going to do them a lot more.” – Steven Forth “Pricing agents will require a shift in how we think about value delivery.” – Steven Forth   Resources and People Mentioned: Jakob Nielsen: https://en.wikipedia.org/wiki/Jakob_Nielsen_(usability_consultant)  OpenAI: https://openai.com/  Zilliant: https://zilliant.com/  Perplexity: https://www.perplexity.ai/  Salesforce's Agent Force: https://www.salesforce.com/ap/agentforce/  Marc Benioff: https://en.wikipedia.org/wiki/Marc_Benioff  AI Agent Layer Cake: https://www.ibbaka.com/ibbaka-market-blog/how-to-price-ai-agents   Connect with Steven Forth: LinkedIn: https://www.linkedin.com/in/stevenforth/  Email: steven@ibakka.com   Connect with Mark Stiving: LinkedIn: https://www.linkedin.com/in/stiving/  Email: mark@impactpricing.com

19 Touko 32min

Blogcast: Practical Pricing in a World with Tariffs

Blogcast: Practical Pricing in a World with Tariffs

This is an Impact Pricing Blog published on March 17, 2025, turned into an audio podcast so you can listen on the go. Read Full Article Here: https://impactpricing.com/blog/practical-pricing-in-a-world-with-tariffs/ If you have any feedback, definitely send it. You can reach us at mark@impactpricing.com.  Now, go make an impact.   Connect with Mark Stiving: Email: mark@impactpricing.com LinkedIn: https://www.linkedin.com/in/stiving/

16 Touko 3min

Pricing as Language: How It Influences Valuation and Market Perception with Mike Blake

Pricing as Language: How It Influences Valuation and Market Perception with Mike Blake

Mike Blake is the founder of High Score Strategies, with over 26 years of experience in business valuation and M&A markets. He specializes in advising small to medium-sized businesses (SMBs) on increasing their valuations. Mike is passionate about the relationship between pricing and value, and how effective pricing strategies can significantly impact a company's worth. In this episode, Mike shares his insights on how pricing affects valuation, the importance of differentiation in a competitive market, and the shift from growth to profitability in business models. Together, they explore the concept of context-driven pricing, the significance of signaling in pricing strategies, and how companies can leverage their unique data to enhance their market position.   Why you have to check out today’s podcast: Discover how pricing communicates a company's brand and market position. Explore the relationship between pricing, profitability, and business valuation. Learn about the importance of differentiation and how to create a competitive moat.   “Pricing is language. It communicates to the market what kind of brand you are.”  – Mike Blake   Topics Covered: 01:37 – The relationship between pricing and valuation.  02:30 – The importance of pricing in determining profitability and cash flow. 03:39 – Differentiation and competitive moats in pricing strategies.  04:53 – The shift from growth to profitability in business models. 08:36 – Signaling in pricing and its impact on investor perception.  11:17 – How to differentiate in a market dominated by larger players.  13:23 – The relevance of pricing strategies for SMBs, and how service-based companies offer consulting as value-ad. 17:04 – What Mike does. 19:36 – Why businesses that don't know their business model. 20:53 – Why value-based pricing is excruciatingly difficult. 25:53 – Mike’s advice on pricing and negotiation.   Key Takeaways: “Pricing is the stem cell for all of that. [Cash flow, revenue, and profitability]” – Mike Blake “Companies that get pricing right are the most valuable.” – Mike Blake “If you're selling 100% of your deals you're probably not optimizing your revenue because you're selling too cheaply.” – Mike Blake “Understanding your unique data can create alternative revenue streams.” – Mike Blake   Connect with Mike Blake: LinkedIn: https://www.linkedin.com/in/unblakeable/ Email: mblake@highscoresstrategies.com   Connect with Mark Stiving: LinkedIn: https://www.linkedin.com/in/stiving/  Email: mark@impactpricing.com

12 Touko 27min

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