SUMMARY
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.

• (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

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.

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.