Street Pricing with Marcos Rivera

AI Pricing: New Costs, Old Rules

Every SaaS company is racing to build with AI. Almost none of them have touched their pricing to match it. This episode pulls together the founders, operators, and pricing experts actually living through that gap — pricing tokens nobody's agreed a value for, replacing seats with performance-based revenue, and figuring out whether AI is making things cheaper or just more confusing. Along the way: a real story about an AI sales call that cost a company a customer, and an AI founder's honest answer to whether any of this replaces human judgment. These are the pricing lessons AI is forcing right now, whether you're ready for them or not. TAKEAWAYS AI can find pricing value you were too scared to test yourself. (George Boretos) If you're pivoting your business to build around AI, your pricing has to pivot with it. (Marcos Rivera) Nobody's agreed on what a token is actually worth — and your customers already know it. (Bill Wilson) Cutting a human for AI can look like savings and still cost you the customer. (Stephen Steers) AI costs are high today. Like every computing technology before it, they'll come down. (Cameron Barragan) If your revenue depends on seats, AI is already coming for that model. (Chris Brisson) Outcome-based pricing means getting paid for the result — not just for access. (Karan Sood) Every seismic shift threatens existing business models. SaaS will survive this one too. (Rob Walling) AI can recommend the price. A person still has to decide it. (George Boretos) The Street Pricing Podcast Welcome to Street Pricing, the only show where proven SaaS (Software as a Service) leaders share their mindset and mistakes in pricing so we can all stop guessing and start growing. Street Pricing is hosted by Pricing I/O CEO and Pricing Coach, Marcos Rivera, sought after slayer of bad pricing. With 20 years of pricing expertise, he has helped price over 200 SaaS products and coached over 100 SaaS CEOs and counting! From the streets of the Bronx to CEO, Marcos wants to take the guesswork out of pricing RESOURCES: George Boretos LinkedIn: https://gr.linkedin.com/in/georgeboretos Evan Munsing LinkedIn: https://www.linkedin.com/in/evan-munsing/ Bill Wilson LinkedIn: https://www.linkedin.com/in/wdrwilson/ Stephen Steers LinkedIn: https://www.linkedin.com/in/stephen-steers/ Cameron Barragan LinkedIn: https://www.linkedin.com/in/cameronbarragan Chris Brisson LinkedIn: https://www.linkedin.com/in/chrisbrisson Karan Sood LinkedIn: https://www.linkedin.com/in/soodkaran/ Rob Walling LinkedIn: https://www.linkedin.com/in/robwalling/ Marcos Rivera LinkedIn https://www.linkedin.com/in/marcoslrivera/ Pricing I/O https://www.pricingio.com/ Street Pricing Book: https://a.co/d/hlMzaM3 Want more information?: info@pricingio.com Chapters (00:00:00) - Intro (00:00:55) - George Boretos on The Company That Doubled Its Revenue Overnight: letting AI find the price you were too scared to charge (00:03:06) - Marcos Rivera on Change Your Business, Change Your Price: why an AI pivot means a pricing pivot too (00:06:10) - Bill Wilson on What Does a Token Even Cost?: pricing something whose cost changes every time you use it (00:07:32) - Stephen Steers on Dirty Revenue: the trust cost of replacing a person with AI (00:13:19) - Cameron Barragan on Is AI Making Things More or Less Expensive?: reading the signals before the pricing shift arrives (00:15:12) - Chris Brisson on Your Seats Are About to Become Worthless: what happens to seat-based revenue as AI eats the conversation (00:18:59) - Karan Sood on Outcome-Based Pricing, Explained: getting paid for the result, not just access (00:22:15) - Rob Walling on SaaS Isn't Dying. It's Changing.: why every seismic shift threatens the old model without ending it (00:25:38) - George Boretos on AI Can Price It. It Can't Decide It.: why the driver still matters more than the car (00:28:03) - Outro

How Charlie AI Priced Its Way to $5.5M a Month

Iggy Odighizuwa, founder of Charlie AI, built an AI-powered sales tool that's now producing $5.5 million a month in cash collected — but getting the pricing right took some real adjustments along the way. Marcos and Iggy trace how an early flat $2,000/month fee didn't account for usage costs, and how that shaped Charlie AI's move to a performance-based model, where clients cover their own usage and hand over a small percentage of the upside the product creates for them. They also get into where Iggy's confidence around pricing and negotiation comes from — being born in Ohio, sent to live in Nigeria as a kid, and learning early that boundaries have to be set and held. A real look at how a growing AI company rebuilt its pricing model around the value it actually delivers. TAKEAWAYS If your costs scale with usage, a flat fee will eventually eat your margin. Price the variable cost, not just the value. Performance-based pricing only works once you've built enough trust for a customer to believe in the outcome. Real conviction means you don't defend your price — you just point at the results. As clients scale with you, the pricing has to scale too, or the incentives fall out of alignment. Get in the right room, get the right information, and don't waste your suffering. The confidence to hold a boundary in business often traces back to the first time you learned to hold one at all. RESOURCES: Iggy Odighizuwa LinkedIn: https://www.linkedin.com/in/iggy-odighizuwa/ Charlie AI.io: https://www.charlieai.io/ Marcos Rivera LinkedIn https://www.linkedin.com/in/marcoslrivera/ Pricing I/O https://www.pricingio.com/ Street Pricing Book: https://a.co/d/hlMzaM3 Want more information?: info@pricingio.com The Street Pricing Podcast Welcome to Street Pricing, the only show where proven SaaS (Software as a Service) leaders share their mindset and mistakes in pricing so we can all stop guessing and start growing. Street Pricing is hosted by Pricing I/O CEO and Pricing Coach, Marcos Rivera, sought after slayer of bad pricing. With 20 years of pricing expertise, he has helped price over 200 SaaS products and coached over 100 SaaS CEOs and counting! From the streets of the Bronx to CEO, Marcos wants to take the guesswork out of pricing Chapters (00:00:00) - Intro (00:01:31) - His Upbringing: From Ohio to Nigeria and Back (00:04:52) - The Boundary-Setting Lesson That Shaped How He Negotiates (00:08:57) - From Personal Trainer to Founder: Learning to Sell (00:10:55) - Why He Built Charlie AI (and the SDR Problem It Solved) (00:16:19) - The Pricing Mistake: Betting on a Flat $2K/Month Fee (00:18:03) - The Wake-Up Call: When Usage Costs Ate the Margin (00:20:57) - The Fix: Moving to Performance-Based Pricing (00:21:54) - Aligning Incentives as Clients Scale (00:29:07) - The Competitor Question: Why He Never Has to Defend His Price (00:33:52) - The Biggest Lesson: Knowledge, Proximity, and Not Wasting Your Suffering (00:35:27) - Where Charlie AI Goes From Here

The Only 8 Pricing Rules You Need | The Best Of Season 1

Most founders don't have a pricing problem, they have a confidence problem. Marcos Rivera brings together the sharpest pricing lessons from founders, operators, investors, and pricing experts. Together, they tackle two of the biggest challenges in pricing: how to know your value and actually charge for it, and how to hold that price once a buyer pushes back. Consider this your cheat sheet for pricing with confidence. TAKEAWAYS Never justify or apologize for your price. The price is the price. (PJ Jackson) You don't have to feel ready to raise your price for it to work. (Rob Walling) Know your total economic value before you set what you'll actually charge. (Karan Sood) Spend most of your time on packaging, not the price number itself. (Peter Cohen) Good friction in your entry tier pushes customers to upgrade when they're ready. (Bill Wilson) Price variability trains buyers to keep squeezing. Consistency builds trust instead. (Michael Shields) Brand does the emotional convincing before pricing ever gets discussed. (Kevan Lee & Shannon Deep) If you want the truth from customers, change your price and listen. (Evan Munsing) RESOURCES: Paul “PJ” Jackson LinkedIn: https://www.linkedin.com/in/pjsayswedontridekangaroos/ Rob Walling LinkedIn: https://www.linkedin.com/in/robwalling/ Karan Sood LinkedIn: https://www.linkedin.com/in/soodkaran/ Peter Cohen LinkedIn: https://www.linkedin.com/in/peter-cohen-8a8b4859/ Bill Wilson LinkedIn: https://www.linkedin.com/in/wdrwilson/ Michael Shields LinkedIn: https://www.linkedin.com/in/shieldsmichaeld/ Shannon Deep LinkedIn: https://www.linkedin.com/in/shannon-deep-34997983/ Kevan Lee LinkedIn: https://www.linkedin.com/in/kevanlee/ Evan Munsing LinkedIn: https://www.linkedin.com/in/evan-munsing/ Marcos Rivera LinkedIn https://www.linkedin.com/in/marcoslrivera/ Pricing I/O https://www.pricingio.com/ Street Pricing Book: https://a.co/d/hlMzaM3 Want more information?: info@pricingio.com The Street Pricing Podcast Welcome to Street Pricing, the only show where proven SaaS (Software as a Service) leaders share their mindset and mistakes in pricing so we can all stop guessing and start growing. Street Pricing is hosted by Pricing I/O CEO and Pricing Coach, Marcos Rivera, sought after slayer of bad pricing. With 20 years of pricing expertise, he has helped price over 400 SaaS products and coached over 100 SaaS CEOs and counting! From the streets of the Bronx to CEO, Marcos wants to take the guesswork out of pricing. Chapters (00:00:00) - Intro (00:00:44) - Paul "PJ" Jackson on The $500 to $5,000 Price Hike: having the courage to charge what you're worth (00:07:51) - Rob Walling on The Fear of the Price Increase: moving before you feel ready (00:13:08) - Karan Sood on The $10 Million Question Every Founder Gets Wrong: understanding value creation (00:18:20) - Peter Cohen on Stop Obsessing Over the Number: packaging correctly (00:22:29) - Bill Wilson on The Friction You SHOULD Add to Your Pricing: designing upgrade paths (00:26:15) - Michael Shields on The Wet Towel Theory of Negotiation: why buyers push (and how to stop giving them a reason to) (00:34:37) - Shannon Deep & Kevan Lee on Brand Is the Heart, Pricing Is Just the Excuse: building brand preference (00:37:56) - Evan Munsing on The Fastest Way to Learn What Customers Really Think: using pricing as market feedback (00:42:03) - Outro

Stop Creating the Boogeyman: How SaaS Sellers Undermine Their Own Pricing | Michael Shields (Tropic)

In this episode of the Street Pricing Podcast , Marcos Rivera talks with Michael Shields, VP of Procurement at Tropic, to get the buyer’s perspective on SaaS pricing. Known as the “boogeyman” to sales teams, Michael pulls back the curtain on how procurement sees variability, discounts, and trust. They unpack why end-of-quarter discounting has created a vicious cycle, how optionality differs from flexibility, and why inconsistent pricing erodes credibility. Marcos and Michael explore the structural fixes—from comp plans to enablement—that help companies sell on value instead of price. The episode closes with Michael’s concept of the “trust dividend”: when buyers believe in your integrity, sales cycles shorten, margins improve, and negotiation disappears. CHAPTERS 00:00 Introduction – Marcos welcomes Michael Shields from Tropic 00:42 Michael’s background: from manufacturing to SaaS procurement 02:52 What buyers really see in SaaS pricing 06:33 The end-of-quarter discount trap 09:58 The wet towel analogy – why sellers get squeezed 12:09 How sellers created the boogeyman 14:05 Optionality vs. flexibility in pricing 16:32 Discipline and enablement in pricing strategy 18:40 Fixing comp plans and quota pressure 21:34 Negotiation as a crutch for poor value framing 24:47 Training and cross-functional alignment in enablement 26:00 Using AI and conversational data to improve deal discipline 28:30 The trust dividend: transparency as a competitive edge 31:33 How great sales reps get procurement to say “yes” 34:16 Michael’s surprise pick: Les Misérables and the power of story 37:24 Marcos’s wrap-up: discipline, trust, and the remix of Street Pricing TAKEAWAYS Price variability signals weak discipline—and buyers will exploit it. End-of-quarter deals and last-minute discounts destroy long-term trust. Structure your discounts with logic (volume, term, bundles), not desperation. Incentives drive behavior—design comp plans that reward early, clean deals. Enablement and negotiation training should be ongoing, not one-off. Review discount patterns with data to uncover value leaks. Optionality builds trust; flexibility breeds chaos. The “trust dividend” is real—credibility shortens cycles and raises prices. Transparency is coming whether sellers like it or not—embrace it as a strength.

AI Turbulence: What Delta’s Pricing Experiment Means for SaaS

In this episode of the Street Pricing Podcast , Marcos Rivera reconnects with Evan Munsing of Corbel Capital Partners to explore the art (and pain) of pricing pivots. From his days as a Marine Corps officer to roles as consultant, operator, and now investor, Evan brings a rare multi-angle perspective on how pricing shapes value creation. He recounts a company’s evolution from sneaker resale to B2B SaaS, highlighting the shifts from buy/sell arbitrage to transaction fees, revenue share, and finally SaaS licensing. Along the way, Evan and Marcos unpack why revenue share models often break, why certainty is worth paying for, and how investors sniff out pricing problems in the boardroom. The conversation ends with hard-earned lessons for SaaS leaders: pricing must lead the pivot, not follow it, and nothing reveals the truth about your product faster than charging for it. CHAPTERS 00:00 Introduction – Marcos welcomes Evan Munsing 01:01 Evan’s background: Marine, consultant, operator, investor 03:59 Pivoting a sneaker resale startup through multiple business models 07:16 From consumer resale to tech-enabled services 09:39 Transaction fees to revenue share 12:32 Pivoting again into B2B SaaS 13:44 The pitfalls of revenue share and value capture 16:11 Raising upfront fees, reducing revenue share 17:26 Growth vs. customer commitment in SaaS pricing 21:17 Why seat pricing misaligns with value 22:47 The CFO’s need for predictability 26:25 Scenario planning, true-ups, and true-forwards 31:18 Pricing as a core part of any pivot 34:45 Pricing as truth: feedback loops from customers 35:57 Boardroom tells that pricing isn’t working 39:17 Evan’s music pick: Jason Isbell, and life lessons from “If We Were Vampires” 40:34 Closing thoughts: value every moment TAKEAWAYS Pricing is strategy, not an afterthought—bring it forward in any pivot. Transaction fees, revenue share, and SaaS licensing each come with trade-offs—know when to evolve. Value share models create disputes and working capital strain; upfront fees drive customer commitment. CFOs crave predictability—companies should structure pricing around certainty, even if it costs more. True-up and true-forward models balance flexibility with financial clarity. Changing your price reveals real customer value faster than surveys or feedback. Investors watch for disappearing KPIs and “too-good-for-too-long” stories as red flags.

Don’t Fear the Algorithm: AI, Trust, and the Future of Pricing

In this special episode of the Street Pricing Podcast , host Marcos Rivera is joined by Pricing I/O teammates Emily Sanz and Steve Inman to unpack Delta Airlines’ headline-making decision to roll out AI-powered ticket pricing. With deep backgrounds in airline revenue management, Emily and Steve separate fact from fear, explaining why AI is less about “personal price gouging” and more about sharper segmentation and inventory optimization. The trio also explore what SaaS leaders can learn from the airline industry—particularly around segmentation, plugging revenue leaks, and the importance of transparent communication when rolling out pricing changes. CHAPTERS 00:00 Introduction – Delta’s AI pricing controversy 01:00 Emily & Steve’s airline pricing backgrounds 02:48 Why AI is just “revenue management on steroids” 05:09 Inventory, demand, and unit economics 07:14 Busting pricing myths (cookies, Tuesdays, etc.) 10:37 AI and special events (Mardi Gras, Super Bowl, hurricanes) 13:11 Price gouging panic and PR fallout 16:01 Plugging leaks and preventing revenue loss 17:41 Segmentation lessons for SaaS 18:59 Communication: getting it right with customers 20:30 Closing reflections and SaaS takeaways TAKEAWAYS AI in airline pricing is about better segmentation and demand forecasting—not spying on customers. Myths like “clear your cookies” or “book on Tuesdays” are folklore, not fact. Events, seasonality, and supply/demand shifts are where AI creates the most value. Poor communication can undermine even the smartest pricing strategies. SaaS leaders should learn from airlines’ mastery of segmentation and apply it to packaging and pricing tiers. Knowing and measuring your North Star KPIs is essential for making AI work in pricing. Transparency builds trust—without it, customers fill the gap with fear and assumptions. RESOURCES: Emily Sanz LinkedIn: https://www.linkedin.com/in/emily-sanz/ Steve Inman LinkedIn: https://www.linkedin.com/in/inmansteven/ Marcos Rivera LinkedIn https://www.linkedin.com/in/marcoslrivera/

Don’t Build on Seats: Why AI Demands a New Revenue Model | Chris Brisson (Salesmsg)

In this episode of the Street Pricing Podcast, host Marcos Rivera speaks with Chris Brisson , CEO and co-founder of Salesmsg. They discuss Chris's entrepreneurial journey, the evolution of pricing strategies in SaaS, and the transition from transactional to subscription revenue models. Chris shares insights on customer behavior, the importance of triggers in pricing, and the impact of AI on business models. The conversation culminates in reflections on triumphs and traps in business growth, emphasizing the need for innovation and adaptability in a rapidly changing market.

Unlocking the Secrets of Pricing Strategies

In this episode of the Street Pricing Podcast, Marcos Rivera and Mark Stiving delve into the complexities of pricing strategies, emphasizing the importance of understanding customer value and the role of AI in shaping pricing models. They discuss the challenges of defining customer problems, the significance of context in pricing, and the evolving landscape of AI-driven pricing solutions. Mark shares insights from his experiences in pricing education and the development of effective pricing strategies, highlighting the need for businesses to adapt to changing market conditions and customer perceptions. CHAPTERS 00:00 Introduction to Pricing Insights 01:43 The Power of Pricing Strategies 06:06 Understanding Value and Customer Problems 11:49 Navigating the Challenges of Problem Definition 15:56 The Role of AI in Pricing 21:53 Future of Pricing in an AI-Driven World 24:26 The Importance of Pricing Strategy 28:07 Navigating AI Product Pricing 35:05 Context-Driven Pricing Insights 42:34 Understanding Customer Value TAKEAWAYS Teaching pricing is about bridging the gap for clients. Pricing is often more complex than it seems. Value is derived from solving customer problems. Understanding customer value is crucial for pricing. Willingness to pay is influenced by context. AI can enhance pricing strategies but requires careful implementation. Identifying customer problems is a challenging yet essential task. Effective pricing requires understanding market segments. Perfection in pricing is unattainable; focus on improvement. Context-driven pricing can help align pricing with customer needs. RESOURCES: Mark Stiving LinkedIn: https://www.linkedin.com/in/stiving/ Impact Pricing LLC: https://impactpricing.com/ Marcos Rivera LinkedIn https://www.linkedin.com/in/marcoslrivera/ Marcos Rivera X https://x.com/PRICINGIO Pricing I/O https://www.pricingio.com/ Street Pricing Book: https://a.co/d/hlMzaM3 Want more information?: info@pricingio.com The Street Pricing Podcast Welcome to Street Pricing, the only show where proven SaaS (Software as a Service) leaders share their mindset and mistakes in pricing so we can all stop guessing and start growing. Street Pricing is hosted by Pricing I/O CEO and Pricing Coach, Marcos Rivera, sought after slayer of bad pricing. With 20 years of pricing expertise, he has helped price over 200 SaaS products and coached over 100 SaaS CEOs and counting! From the streets of the Bronx t...

From Guesswork to Growth: How AI is Rewriting the Pricing Playbook

Dirty Revenue Is Killing Your Business | Stephen Steers (Steers Consulting)

In this episode of the Street Pricing podcast, Marcos Rivera and Stephen Steers delve into the intricacies of sales, focusing on how founders can transition out of day-to-day sales roles while enhancing conversion rates. They discuss the importance of reducing friction in sales processes, the necessity of proper discovery to understand client needs, and the innovative approach of qualifying out potential clients to ensure a better fit. The conversation emphasizes the value of listening to sales calls and utilizing frameworks to improve sales effectiveness. In this conversation, Stephen Steers and Marcos Rivera discuss the importance of building trust in sales through clear deliverables and patience. They explore the role of AI in sales, emphasizing that while it can be a useful tool, it should not replace the human element in building relationships. The discussion highlights key strategies for increasing conversion rates and the significance of maintaining a strong reputation in business. CHAPTERS 00:00 Introduction to Sales Mastery 03:01 The Art of Firing Yourself from Sales 06:01 Reducing Friction in Sales 09:00 The Importance of Discovery in Sales 12:05 Qualifying Out: A New Approach 15:05 Listening to Your Sales Calls 18:01 Frameworks for Increasing Conversion Rates 20:57 Building Trust Through Deliverables 24:31 The Importance of Patience in Sales 29:07 AI in Sales: A Double-Edged Sword 34:10 Key Takeaways for Sales Success TAKEAWAYS Firing yourself from sales allows founders to focus on growth. Reducing friction in the sales process increases conversions. Trust is built through consistent actions and communication. Proper discovery is essential for understanding client needs. Qualifying out clients can lead to better business relationships. Listening to sales calls provides valuable insights for improvement. Sales objections can be categorized into three main types. Packaging offers in a low-risk manner boosts initial engagement. Sales frameworks can streamline the selling process. Continuous learning from past sales interactions is crucial. Instead of going straight for a retainer, start with a smaller project. Clarity in what clients will receive increases conversion rates. Building trust takes time and patience. AI can be a useful tool but should not replace human interaction. Sales success relies on understanding client needs and delivering value. Recording and reviewing sales calls can improve performance. Establishing a clear process helps clients understand the journey. Long-term thinking is essential for sustainable business growth. Trust is built through consistent and reliable interactions. Patience is a skill that can be developed over time. RESOURCES: Stephen Steers LinkedIn: https://www.linkedin.com/in/stephen-steers/ Steers Consulting Group: https://www.stephensteers.com/ Marcos Rivera LinkedIn https://www.linkedin.com/in/marcoslrivera/ Marcos Rivera X https://x.com/PRICINGIO Pricing I/O