Libsyn Directory

Evolution of Pricing Strategies in Business with Gary Bailey

Lifeselfmastery's podcast I Startups I Venture Capital

Release Date: 10/30/2025

Why Silicon Valley Still Wins with Lars Leckie of AspenWood Ventures

Lifeselfmastery's podcast I Startups I Venture Capital

I am thrilled ot have , a Partner at Aspenwood Ventures, bringing a rare founder-turned-investor perspective to early-stage investing. He co-founded AutoFarm (now Novariant), pioneering GPS and robotics in agriculture, where he built sales teams across three continents In this conversation, Lars Leckie shares his unique journey from coding and gaming to becoming a partner at AspenWood Ventures. He discusses the critical lessons learned from his early experiences in sales and strategy, emphasising the importance of understanding customer needs and the divide between engineering and sales...

Courageous Marketing: How Udi Ledergor Scaled Gong from Zero to Unicorn

Lifeselfmastery's podcast I Startups I Venture Capital

I am thrilled ot have the Chief Evangelist at Gong, where he spent nine years helping build the company from zero to a multi-billion-dollar valuation. A five-time B2B marketing leader, bestselling author of Courageous Marketing, angel investor, and board member In this conversation, Udi Ledergor, Chief Evangelist at Gong, shares his journey from product management to leading marketing at a billion-dollar company. He emphasizes the importance of human-centric marketing, the need to challenge traditional best practices, and the significance of creating valuable content that resonates with...

Railsware's Journey from Agency to SaaS Powerhouse with Sergiy Korolov

Lifeselfmastery's podcast I Startups I Venture Capital

I am excited to have Sergiy, who is the Co-CEO of Railsware and co-founder of multiple products In this conversation, Sergiy Korolov, CEO of Railsware, discusses his journey from software developer to entrepreneur, the evolution of his products like Mailtrap and Coupler, and the challenges faced in the tech industry. Sergiy shares insights on transitioning from service to product, the importance of understanding user segments through surveys, and the role of AI in enhancing productivity. He also reflects on the complexities of email delivery and strategies for competing against larger...

Rise of Defence Tech from Brad Harrison from Scout Ventures

Lifeselfmastery's podcast I Startups I Venture Capital

I am thrilled to have , a former Army Ranger turned venture capitalist, and the founder and Managing Partner of Scout Ventures. Brad invests at the intersection of national security and critical technology innovation, backing companies like Unite Us, ID.me, Voyager Space, and Tomahawk Robotics — which was recently acquired by AeroVironment. In this conversation, Brad Harrison, a former Army Ranger turned venture capitalist, shares his journey into the world of venture capital and the founding of Scout Ventures. He discusses the importance of mission-driven investments, particularly in the...

Emerging Market Lessons That Make Better Investors with Elias Mufarech from Collide Capital

Lifeselfmastery's podcast I Startups I Venture Capital

I am thrilled to have who is a Senior Associate at Collide Capital, a pre-seed to Series A venture fund investing in fintech, future of work, and supply chain software. In this conversation, Elias Mufarech, a senior associate at Collide Capital, shares his insights on venture capital, the importance of operational support for founders, and the evolving landscape of startup expectations. Elias discusses his journey from building fintech software in Latin America to investing in startups, highlighting the critical lessons learned along the way. He emphasizes the need for founders to have strong...

Ankur Patel from Multimodal on Building Agentic AI for the Enterprise

Lifeselfmastery's podcast I Startups I Venture Capital

I am excited to have who is the founder and CEO of , where he's automating the most complex workflows in finance and insurance. He has 15+ years of work experience across companies like J.P. Morgan and Bridgewater In this conversation, Ankur Patel, founder and CEO of Multimodal, traces his path from JP Morgan and Bridgewater to building AI agents that automate complex workflows in finance and insurance. He explains how early exposure to data science and macro trading convinced him that AI would reshape enterprise work. He discusses why agentic AI is fundamentally different from...

How Vivek Krishnamurthy from Commerce Ventures Thinks About Venture, AI, and Markets

Lifeselfmastery's podcast I Startups I Venture Capital

I am thrilled to have , who is a Partner at , where he's spent over 8 years investing in commerce infrastructure and fintech. Before Venture, he was an Investment Banking Analyst at Financial Technology Partners. He's particularly bullish on AI's transformation of insurance, backing companies like Kin Insurance, Liberate, and Authentic. In this conversation, Vivek Krishnamurthy, a partner at Commerce Ventures, discusses his journey into venture capital, the evolution of investment strategies, and the intersection of commerce and fintech. Vivek shares insights on the impact of AI on business,...

Dallas Price from Forum Ventures on Venture Studios, Founder-Market Fit, and What Actually Wins in AI

Lifeselfmastery's podcast I Startups I Venture Capital

I am excited to have , a Venture Builder at , where he helps launch and scale six B2B SaaS startups every year through their AI Studio. His work centres on turning early-stage concepts into real companies, guiding founders across product, go-to-market, and fundraising In this conversation, Dallas Price, a venture builder at Forum Ventures, discusses his journey into the startup world, the workings of a venture studio, and the current landscape of AI startups. Dallas shares insights on navigating chaos in startups, the importance of defensibility, new distribution channels, and evolving pricing...

Capital Evolution: A New Era of Capitalism with Seth Levine and Elizabeth McBride

Lifeselfmastery's podcast I Startups I Venture Capital

I am excited to have , venture capitalist and co-founder of Foundry, and , international business journalist and founder of Times of Entrepreneurship. Together, they co-authored The New Builders and now their latest book, , explores how American capitalism is shifting—and why businesses, not government, may hold the keys to building a more inclusive and prosperous future. In this conversation, Seth Levine and Elizabeth McBride discuss their new book, 'Capital Evolution,' which explores the shifting landscape of American capitalism. They delve into the challenges posed by neoliberal...

Art and Science of Pricing Strategies with Marcos Rivera of Pricing I/O

Lifeselfmastery's podcast I Startups I Venture Capital

I am thrilled to have , the founder and CEO of , where he helps B2B SaaS companies capture the value they've built. Former Head of Pricing at Vista Equity Partners, he's priced over 400 SaaS products and has authored Street Pricing. In this conversation, Marcos Rivera, founder and CEO of Pricing.io, discusses the intricacies of pricing strategies in B2B SaaS. Marcos shares his journey from product management to pricing, highlighting common mistakes companies make, especially in underpricing their products. He emphasizes the importance of understanding customer needs, the blend of art and...

More Episodes

I am thrilled to have Gary Bailey, founder of Strategim, a monetisation & pricing expert with a deep background in financial services, accounting, pricing, and AI.

In this conversation, Gary Bailey, a monetisation and pricing expert, shares his journey from accounting to product management and pricing. He discusses the importance of pricing as a core discipline in business education, the evolving role of finance in pricing strategies, and the impact of AI on SaaS pricing models. Gary emphasizes the need for training the next generation in pricing and the role of a monetization architect in modern businesses. He also highlights common pricing mistakes, the importance of starting the monetisation journey with a feature list, and the need to redesign business education to adapt to the changing landscape.

Timestamps

06:00 The Importance of Pricing in Business Education

09:17 Balancing Certainty and Uncertainty in Pricing

13:17 The Evolution of SaaS Pricing with AI

16:50 Training the Next Generation of Pricing Professionals

20:35 The Role of a Monetization Architect

22:26 The Architecture of Pricing Strategies

23:37 Evolving Pricing Models in SaaS

25:58 The Impact of AI on Job Markets

29:19 Preparing for an AI-Driven Future

32:17 Learning from Pricing Mistakes

33:48 Rebundling Features for Better Monetization