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: [email protected]