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.
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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 entrepreneurs, emphasizing that being 'better' is often a trap that leads to commoditization. The conversation highlights the need for businesses to identify their unique strengths and create solutions that address unrecognized customer needs. In this conversation, Alex and Marcos explore the nuances of business strategy, emphasizing the importance of innovation, self-reflection, and understanding customer value. They discuss how companies can unlock new value by reframing weaknesses and finding their unique position in the market. The dialogue also touches on the challenges tech companies face in differentiating themselves and the pitfalls of overly complex pricing strategies. Ultimately, they advocate for a straightforward approach to strategy that focuses on generating meaningful value for customers.
CHAPTERS
00:00 Introduction to Strategy and Pricing
04:10 The Journey to No Bullshit Strategy
13:44 Understanding Market Positioning
20:34 Creating Unique Value Propositions
26:09 Unlocking Value Through Innovation
29:07 The Importance of Self-Reflection in Strategy
32:37 Navigating the Tech Landscape: Familiarity vs. Uniqueness
34:09 Crafting a Compelling Strategy
38:01 The Right to Exist: Generating New Value
42:25 Debunking Value-Based Pricing
49:34 Personal Touch: Music and Memories
TAKEAWAYS
Strategy is often overlooked by many entrepreneurs.
Most businesses operate reactively without a clear strategy.
Claiming to be the best is often a flawed strategy.
The market rewards uniqueness, not just superiority.
Many entrepreneurs fail to differentiate their offerings.
Customer service claims need factual backing.
Creating a need can lead to innovative solutions.
Understanding your unique value is crucial for success.
Most markets are well-served, making innovation challenging.
Strategy should be accessible and enjoyable for all entrepreneurs. Innovation can create new market opportunities.
Reframing weaknesses can lead to unique value propositions.
Self-reflection is crucial for identifying strengths.
Successful businesses balance familiarity with uniqueness.
Tech companies often struggle with differentiation.
A compelling strategy should be rooted in normalcy.
Strategy should be presented as a narrative argument.
Generating new value is essential for business survival.
Value-based pricing may overlook psychological factors.
Contextual pricing may be more effective than value-based pricing.
RESOURCES: Alex Smith LinkedIn: https://www.linkedin.com/in/alex-m-h-smith/ BasicArts Website: https://basicarts.org/ The Hidden Path Newsletter: https://basicarts.org/newsletter/ Marcos Rivera LinkedIn
Why Pricing Deserves a Seat at the Strategy Table
mercredi 14 mai 2025 • Durée 41:57
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, and the value of customer feedback in shaping product offerings. Ali emphasizes the need for alignment within management teams and the significance of removing friction in sales processes to enhance customer experience. In this conversation, Ali Mamujee and Marcos Rivera delve into the intricacies of sales processes, the critical relationship between strategy and pricing, and the importance of crafting a unique value proposition. They discuss the challenges faced by B2B SaaS companies in communicating effectively and the need for a streamlined sales cycle. The conversation also touches on the integration of technology in enterprises and the emotional aspects of sales proposals. Ali shares insights from his experience in entrepreneurship, emphasizing the importance of relationships and embracing the challenges of the 'messy middle' in business growth.
CHAPTERS 00:00 Introduction to Ali Mamoudji and His Journey 02:27 The Genesis of Mercatus and Its Evolution 04:51 Navigating Growth and the Importance of Pricing 09:54 The Role of Data in Pricing Decisions 14:59 The Power of Customer Conversations 19:58 Aligning Management Through Pricing Strategy 23:49 Streamlining Sales Processes for Efficiency 25:45 The Interplay of Strategy and Pricing 26:15 Crafting a Unique Value Proposition 30:43 The Sales Process as a Product 33:15 Communicating Effectively in B2B SaaS 35:26 Navigating Technology Integration Challenges 38:45 Embracing the Messy Middle of Entrepreneurship
TAGLINES
The $100K Mistake Most Founders Make
Sales Shouldn’t Own Pricing—Here’s Why
● Ali Mamujee has a background in B2B SaaS and investment banking.
● Mercatus aimed to fill a gap in managing complex renewable energy assets....
Good, Better, Broken: Why Most SaaS Pricing Fails SaaS Pricing Tiers Are a Trap—Here’s How to Fix Them
mercredi 30 avril 2025 • Durée 14:43
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 plans, and the significance of add-ons. He concludes with a guide to five key principles for successful pricing strategies.
TAKEAWAYS
Good, better, best is a popular pricing model in SaaS.
Understanding your total addressable market (TAM) is crucial.
Avoid overstuffing your entry-level plan with features.
Add-ons can help create stair steps for customers.
Focus on solving the first few jobs in the customer journey.
Keep pricing tiers simple and clear.
Aim for two to four pricing tiers for effectiveness.
Differentiate plans with clear value propositions.
Charge significantly more for the best plan.
Regularly review and adjust your pricing strategy.
CHAPTERS
00:00 Introduction to Good, Better, Best Pricing
06:10 Common Mistakes in Pricing Models
12:10 The Guide to Five: Key Principles for Pricing
Pricing I/O https://www.pricingio.com/ Street Pricing Book: https://www.amazon.com/Street-Pricing-Playlist-Leaders-SaaS/dp/1737528010 Want more information?: info@pricingio.com
How to Scale Your Cold Email Campaigns Effectively | Nikita Bykadarov (Maildoso)
mercredi 16 avril 2025 • Durée 37:06
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 offerings, growth metrics, and the value of customer education. The conversation emphasizes the need for startups to focus on solving core problems and adapting to customer needs.
Takeaways
Maildoso helps ensure cold emails land in inboxes, not spam.
Pricing strategies evolved from annual to quarterly based on customer feedback.
Customer acquisition cost is low due to effective cold email strategies.
Maildoso has grown to over 3,000 customers in under a year and a half.
Deliverability is the core value proposition of Maildoso
Customer education is key to improving email marketing success.
Nikita emphasizes the importance of managing stress as a startup founder.
The company focuses on solving the core problem of email deliverability.
Maildoso’s growth is driven by a commitment to value and customer success.
Iterative improvements in pricing and offerings are essential for growth.
Chapters
00:00 Introduction to Cold Email Solutions
03:03 Pricing Strategies and Customer Acquisition
05:55 The Evolution of Maildoso's Offerings
09:10 Growth Metrics and Customer Success
12:05 Challenges and Future Plans
15:02 Deliverability and Customer Education
17:46 Reflections and Advice for Future Entrepreneurs
Don't Procrastinate on Pricing | Rob Walling (TinySeed)
Épisode 41
mardi 25 mars 2025 • Durée 38:41
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 reveals the psychological hurdles he faced before implementing the change and the expansion revenue that followed, emphasizing that pricing is "the biggest lever in SaaS."
Beyond pricing, Rob unpacks his framework for diagnosing and breaking through SaaS plateaus, offering his "Big Five" marketing approaches for B2B growth. The conversation concludes with Rob's perspective on AI's impact on SaaS—predicting short-term challenges but long-term opportunities for founders who adapt as business models evolve from traditional interfaces to APIs and agent-based interactions.
In this episode:
(00:00) Introduction to Rob Walling, renowned entrepreneur and investor, highlighting his contributions to the SaaS and startup ecosystem. Rob shares his mission to empower independent startups through his work with TinySeed, MicroConf, and the podcast "Startups for the Rest of Us."
(11:55) Overcoming Pricing Anxiety in Startups - Rob shares personal experiences with pricing strategy development, focusing on the importance of overcoming fear to unlock growth potential. The conversation explores the impact of expansion revenue and the necessity of clear communication during pricing changes.
(21:02) We delve into strategies for navigating growth challenges in SaaS businesses. Rob stresses the importance of regular pricing strategy adjustments and the role of strategic marketing in driving business expansion.
(27:42) Effective marketing strategies for B2B SaaS companies - known as the "big five": content, SEO, cold outreach, integrations and partnerships, and ads. Rob shares insights into tailoring these strategies to specific business contexts and stresses the importance of adaptability and quick execution to avoid stagnation.
‘Happy vs. Crappy’ Data to Winning Pricing Strategies | The Data Ninjas (Pricing I/O)
Épisode 40
mardi 11 mars 2025 • Durée 46:47
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 how to transform "crappy" data into actionable insights by unifying fragmented datasets, tracking feature usage patterns, and analyzing lost deals.
You’ll hear practical survey guidance with specific recommendations on sample sizes, survey length (keep it under 15 minutes!), and when to use methodologies like conjoint analysis versus Van Westendorp. For SaaS leaders struggling with packaging decisions, the experts explain how to identify value patterns in usage data and leverage AI for real-time competitive analysis while maintaining human oversight. This episode delivers concrete frameworks for moving beyond pricing guesswork to data-driven strategy.
In this episode:
(00:00) Marcos introduces six data leads from Pricing I/O who collectively analyze massive amounts of pricing data. Each team member shares their background, from strategic finance and investment analysis to market research and biotech.
(04:05) Navigating the data landscape - “Happy vs. Crappy” - Critical aspects of data quality for pricing analysis, emphasizing the importance of unified data with consistent account IDs, tracking both absolute and relative feature usage, and collecting lost deal information to understand what products aren't selling well.
(19:09) Tips on creating effective pricing surveys, including keeping surveys under 10-15 minutes to avoid respondent fatigue, using neutral language in questions, and adjusting survey methodology based on expected sample size.
(29:11) Examining different pricing survey methodologies, focusing on conjoint analysis for determining feature value.
(36:00) Benefits of customer surveys versus expert interviews, insights on how customer surveys force companies to think from the customer's perspective, while expert surveys provide deeper, more invested responses.
The Dark Side to Simple | Peter Bonney (FastbreakRFP)
Épisode 39
mardi 25 février 2025 • Durée 30:32
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 with opaque, usage-based pricing models in the RFP space, Peter built Fastbreak RFP to introduce predictable, user-based pricing that scales with customer success.
We unpack key insights into RFP pricing models, including:
- The hidden costs and challenges of usage-based pricing in RFP software
- How the shift from usage-based to user-based pricing impacts customer retention
- Real-world examples of simplifying compliance workflows through pricing structure
Peter shares his framework for building pricing tiers that align with procurement workflows, demonstrating how Fastbreak RFP reduced sales friction through transparent pricing architecture. For pricing leaders wrestling with the complexity of enterprise RFP solutions, Peter reveals his playbook for packaging AI capabilities without creating pricing anxiety.
Whether you're rethinking your pricing strategy or seeking insights on monetizing AI features in enterprise software, this discussion offers actionable frameworks for modern SaaS pricing architecture in complex markets.
In this episode:
(00:00) Introduction of Peter Bonney, Founder and CEO of Fastbreak RFP
(03:46) Rewind story, Peter's entrepreneurial journey and evolution of Fastbreak’s pricing strategies, the chaotic nature of enterprise RFPs and Fastbreak RFP's automation solutions
(16:21) Resolving pricing misalignment, pricing models in AI-driven businesses and the transition from usage-based to user-based pricing
Top Pricing Recommendations for 2025 | The Pricing I/O Experts
Saison 1 · Épisode 38
mardi 11 février 2025 • Durée 36:30
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 transportation, and tech. Each of my talented colleagues shares their unique insights into the art of pricing. We engage in a dynamic roundtable discussion, unraveling the intricacies of delivering just the right amount of value without overextending, a vital strategy for maximizing utility in SaaS pricing. Our conversation reveals how to effectively capture value and tackle the complexities of pricing across different sectors, guiding SaaS companies toward optimal pricing models.
The discussion begins with a deep dive into why software packaging deserves more attention than pricing itself, with the team advocating for an 80/20 split in favor of packaging considerations. They explore why providing the right amount of value, rather than maximizing features, is crucial for customer satisfaction and revenue growth in SaaS businesses.
The conversation then shifts to analyzing Salesforce's recent move to conversation-based pricing for their AI agent service, charging $2 per conversation instead of traditional user-based licensing. The team debates the implications of this shift and whether it would work for smaller companies without Salesforce's data advantages and established customer base. The episode concludes with team members sharing their key advice for SaaS leaders in 2025, including the importance of customer feedback, service differentiation, careful discounting practices, and implementing effective pricing committees.
In this episode: (00:00) Team Introductions - Pricing I/O team members including Peter Cohen, Steve Inman, Mario Pereda, Emily Sanz and Amit Saraf - each bringing different pricing expertise across industries
(05:09) “A-ha” moments, packaging vs pricing, why software packaging deserves more attention than pricing levels, with the recommendation to spend 80% of time on packaging and 20% on price points, why giving customers the right amount of value (no more, no less) is crucial for SaaS success
Behind Docker's No-Brainer Bundle | David Caughman (Axia Consulting, Docker)
Saison 1 · Épisode 37
mardi 28 janvier 2025 • Durée 35:16
Crushing Competition with Customer Insight | Eric Weiss (Chaos to Clarity)
Saison 1 · Épisode 36
mardi 14 janvier 2025 • Durée 40:41
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. Drawing from his extensive experience, Eric highlights the transformative power of human-centered design through compelling case studies, such as differentiating an email marketing platform in a crowded market. Marcos and Eric also explore how companies can leverage customer feedback to enhance user experience and retention, advocating for a ‘discovery-led growth’ mindset.
Later in the episode, Eric provides valuable insights into the challenges and potential of AI in product development. Incremental integration is key to ensure reliable user experiences. You’ll hear the importance of empathy, strategic design, and continuous learning to achieve product-market fit and unlock market potential. This episode is a must-listen for entrepreneurs seeking to harness innovative strategies for growth and value capture.
In this episode:
(00:00) Guest intro of Eric Weiss, CEO of Chaos to Clarity
(04:10) Rewind story, the importance of customer value as a driver for pricing strategies and growth, free master classes
(15:26) Creating better interfaces, how companies can enhance user experience and retention through customer feedback, simplified onboarding, maintaining a discovery-led approach with continuous customer engagement
(20:43) How you can start your discovery-led growth - talk to your customers! Speak their language, ask the right questions, find the custom solution for them
(29:30) What’s going on today - Delving into the challenges of AI integration, the importance of balancing innovation with consistent user experiences, and avoiding customer churn, AI “Agency” - allowing to take steps for you
(41:37) Know your customer better than they know themselves - empathy in understanding customer needs and crafting elegant solutions, aiming to be the best in the market, value of knowing your customer and being a master in your field
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.
(36:34) The transformative impact of AI on the SaaS industry, drawing parallels with past technological revolutions. Rob expresses some of the challenges and opportunities AI presents for existing business models and underscores the importance of adaptability for future success.
(38:32) Rob shares his favorite jam by Third Bass, an unexpected musical choice
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 guessing out of pricing.
(40:30) “Get out of my way-I” - How AI is transforming pricing analytics by accelerating insights and putting data at the forefront of decision-making.
(44:44) AI applications for competitive data analysis, real-time price adjustments, and processing large datasets, while addressing data privacy concerns when utilizing AI systems for client information.
(45:55) Favorite current jams from the team!
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 guessing out of pricing.
(20:41) Challenges in simplifying pricing models for large companies and the benefits of tiered seat models, transitioning to user-based pricing for clarity and predictability
(26:00) Future of pricing models, leveraging AI for “magical” RFP responses and CRM integrations to create tailored responses
(31:05) Closing remarks, favorite jam by Living Colour
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 guessing out of pricing.
(17:41) Salesforce's move from user-based licensing to charging $2 per conversation for their AI agent, the pros and cons of this pricing strategy and its implications for the industry
(31:38) Team members share their top pricing recommendations for 2025, including:
- Getting customer and employee feedback regularly
- Focusing on services as a differentiator
- Being careful with discounting
- Implementing a pricing committee
(37:16) Closing remarks, favorite jams
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 guessing out of pricing.
(44:38) Closing remarks, favorite jam from Metallica
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 guessing out of pricing.
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