Street Pricing with Marcos Rivera
You’re listening to the Street Pricing podcast - The only show where proven SaaS leaders share their mindset and mistakes in pricing so we can all stop guessing and start growing. Enjoy, subscribe, and tell a friend. Now, let’s break it down with your host and sought-after slayer of bad pricing, Marcos Rivera.
Episodes
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...
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 per...
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
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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 wh...
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...
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, ex...
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 mo...
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...
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 en...
In this episode of the Street Pricing Podcast, host Marcos Rivera speaks with Alex Smith, founder of Basic Arts and author of 'No Bullshit Strategy.' They discuss the importance of strategy in business, the common pitfalls entrepreneurs face, and how to create unique value propositions that stand out in the market. Alex shares his journey from being a strategy consultant to democratizing strategic thinking for entrepr...
In this episode of the Street Pricing Podcast, host Marcos Rivera speaks with Ali Mamujee, a growth and strategy advisor in the B2B SaaS space. Ali shares his journey from being an early employee at Mercatus, a platform for managing complex renewable energy assets, to becoming a solo advisor for startup growth. The conversation delves into the importance of pricing strategies, the role of data in decision-making, a...
In this episode of the Street Pricing Podcast, Marcos Rivera discusses the popular pricing model of good, better, best, particularly in the SaaS industry. He emphasizes the importance of understanding your total addressable market (TAM) and the common mistakes companies make when implementing this pricing strategy. Rivera provides insights on how to effectively structure pricing tiers, avoid overstuffing entry-level p...
In this episode of the Street Pricing Podcast, host Marcos Rivera interviews Nikita Bykadarov, CEO of Maildoso, a startup focused on improving cold email deliverability. They discuss the challenges of cold email marketing, pricing strategies, customer acquisition, and the importance of deliverability in email campaigns. Nikita shares insights from his journey, including the evolution of Maildoso's off...
Why does Rob Walling call pricing "the biggest lever in SaaS" and how often does he recommend revisiting your pricing strategy?
In this value-packed episode of the Street Pricing Podcast, Marcos Rivera interviews Rob Walling, founder of Drip and TinySeed accelerator, who shares how changing his SaaS pricing model from "new subscribers" to "total subscribers" transformed his business. Rob reveal...
Is your pricing metric actually tracking what delivers the most value to customers—and could a misalignment be causing hidden churn?
Join me for a data-driven conversation with Pricing I/O data ninjas Sam Blumenfeld, Matthew Duncan, Kyle Eustaquio, Nishita Katere, Jack LoGrasso and Brenden Murden. We demystify what "good data" actually means for SaaS pricing decisions. The team unpacks ho...
Why did Peter Bonney decide to pivot from usage-based pricing to a flat, user-based model, and how has this shift impacted Fastbreak RFP's growth and customer satisfaction?Join me for a candid conversation with Peter, who's transforming how enterprises handle RFPs (Requests for Proposals) through intelligent pricing architecture. After seeing enterprises struggle ...
How can SaaS companies benefit from the seasoned insights of the Pricing I/O team to navigate complex market dynamics and achieve pricing excellence?
Today I’m speaking with Peter Cohen, Steve Inman, Mario Pereda, Emily Sanz and Amit Saraf - a special lineup of pricing experts from the Pricing I/O team. These experts have vast knowledge across various industries like airlines, freight tr...
How can entrepreneurs unlock exponential growth by understanding and leveraging “discovery-led growth” in their pricing strategies?
Today, Street Pricing listeners are treated to Marcos’ discussion with Eric Weiss, CEO of Chaos to Clarity. Eric delves into the intricacies of entrepreneurial growth with an emphasis on understanding customer value....
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