Ashish Gupta, founder and CEO of ScaleUp Exec, brings a unique perspective to pricing from his experience building and selling multiple companies across technology, e-commerce, and subscription businesses. Starting his career at Anheuser-Busch (as the company's only non-drinker), Ashish has led businesses from startup to eight-figure valuations, giving him deep insights into pricing across different business models and growth stages.

In this episode, Ashish shares unconventional pricing strategies that transformed his businesses, including how he convinced vendors to provide products for free by repositioning his company as a marketing partner rather than a traditional retailer.

Why you have to check out today's podcast:

• Discover how to identify and target the specific customer segments willing to pay premium prices for your unique value proposition.
• Learn the "influencer plus" strategy that transforms vendor relationships from cost centers into revenue-generating partnerships.
• Understand how subscription businesses create deeper customer relationships and the pricing implications of holding customer credit cards.

"Instead of trying to go to a general audience, which may or may not be interested in paying you more for something unique about your product, really try and understand who is that core set of people that will find real value and be willing to pay for that value."

– Ashish Gupta

Topics Covered:

01:48 — Ashish's entrepreneurial journey: From Anheuser-Busch to multiple successful exits.

03:42 — The psychology of subscription pricing: Why holding credit cards creates deeper customer relationships.

07:54 — Win, Keep, Grow framework: The often-overlooked "grow" component in subscription businesses.

11:03 — ScaleUp Exec's fractional COO model: Bringing enterprise talent to small and medium businesses.

13:45 — Revenue growth strategies: How COOs approach customer acquisition and diversification differently.

17:34 — The pricing audit revelation: Why PE firms consistently find underpriced acquisitions.

22:01 — The "off balance sheet CFO" positioning strategy for premium pricing.

22:58 — The vendor flip strategy: From paying wholesale to getting products for free.

24:04 — Building the "influencer plus" model: Combining audience and distribution for vendor value.

Key Takeaways:

"I think relationship and subscription are, they kind of go hand in hand. That means I have to always be getting value. I have to have this confidence that, if somebody has my credit card and I've given them authorization to charge it versus like, let's say an Amazon, I'm proactively going in and saying, yes, I want this item." – Ashish Gupta

"If we can build out our own audience, and grow that audience to be something meaningful and have a deep connection with that audience so that they really trust us, our brand as a retailer, then we can actually talk with our vendors and say, hey, we're no longer a retailer, we're really a marketing company." – Ashish Gupta

Resources and People Mentioned:

• Anheuser-Busch: https://www.anheuser-busch.com
• Shopify Shop Pay: https://www.shopify.com/shop-pay
• PayPal: https://www.paypal.com/
• Mark Stiving's book: "Win, Keep, Grow" about subscription businesses

Connect with Ashish Gupta:

• Website: https://scaleupexec.com/
• Linkedin: https://www.linkedin.com/in/ashish-gup/

Connect with Mark Stiving:

• LinkedIn: https://www.linkedin.com/in/stiving/
• Email: mark@impactpricing.com

This is an Impact Pricing Blog published on June 9, 2025, turned into an audio podcast so you can listen on the go.

Read Full Article Here: https://impactpricing.com/blog/why-pricing-ai-is-so-hard/

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/

Craig Wilson, Director of Pricing and Packaging at Moody's Analytics, brings extensive experience from major financial services companies including S&P and Experian. Starting his career in financial analysis at a Scottish car retailer after his soccer dreams didn't materialize, Craig discovered his natural strengths in numbers and analytical tools, leading him to specialize in pricing across subscription products, deal desk operations, and information technology services.

In this episode, Craig explores the dual challenge of AI in pricing: how to monetize AI-enhanced products and how to leverage AI tools for pricing decisions. Drawing from his experience at Moody's, he discusses why traditional pricing principles still apply to AI products while acknowledging the fundamental disruption AI creates for per-user models. Craig shares practical insights on using AI as a pricing coach and the critical importance of early involvement in product development.

Why you have to check out today's podcast:

• Learn why AI pricing follows traditional value-based principles but requires new approaches to pricing metrics and value capture.
• Discover practical ways to use AI tools like Microsoft Copilot for pricing strategy, stakeholder communication, and sales enablement.
• Understand the critical timing of pricing involvement in AI product development to influence monetization strategies from the ground up.

"Get involved in the product development process as early as possible, particularly in the era of Gen AI and agentic AI."

– Craig Wilson

Topics Covered:

01:30 — Craig's pricing journey: From Scottish car retailer to Moody's Analytics pricing leader

04:15 — Why AI pricing fundamentals haven't changed: Still about value creation and capture

06:30 — The consensus problem: No clear patterns yet in AI pricing

08:45 — Use case example: using AI to do pricing

11:15 — Using AI as a pricing coach: Daily conversations with Microsoft Copilot for strategy development

14:30 — Communication enhancement: Translating pricing concepts for different business personas

16:45 — Sales enablement evolution: AI-powered guidance for complex solution positioning

19:20 — Trust and validation concerns: The information vs. agentic AI distinction

21:45 — Economic value estimation: How AI can finally make this pricing holy grail practical 23:30 — The monetization investment gap: Companies building AI capabilities without pricing strategies

Key Takeaways:

On Early Involvement in Product Development:

"Get involved in the product development process as early as possible, particularly in the era of Gen AI and agentic AI." – Craig Wilson

On Per-User Pricing's Death:

"In the world of particularly agentic AI solutions, the per-user model is becoming obsolete. I can't see a place for it." – Craig Wilson

Resources and People Mentioned:

• Moody's Analytics: https://www.moodysanalytics.com/
• Tom Nagle: "Strategy and Tactics of Pricing" book: https://www.taylorfrancis.com/books/mono/10.4324/9781315266220/strategy-tactics-pricing-thomas-nagle-john-hogan-joseph-zale
• Steven Forth: https://www.linkedin.com/in/stevenforth/
• Kyle Poyar: https://www.linkedin.com/in/kyle-poyar/
• Stuart Wintertere: LinkedIn thought leader on AI value
• Microsoft Copilot: Daily AI coaching tool

Connect with Craig Wilson:

• LinkedIn: https://www.linkedin.com/in/craig-wilson-5857ba4a/
• Email: craig.wilson@moodys.com

Connect with Mark Stiving:

• LinkedIn: https://www.linkedin.com/in/stiving/
• Email: mark@impactpricing.com