Eytan Bensoussan, CEO of a banking service, discusses the importance of ruthless prioritization to achieve productivity and success. He highlights the problem of cashflow mismanagement in small businesses and the challenges of financial management in early stages. He also talks about the decision to seek VC funding, managing negative emotions, and the value of creating valuable content like a podcast for businesses.

Jeff Gothelf, an expert on OKRs and being outcome-driven, discusses humility and accountability in executives, setting outcome-driven goals for exploratory research, the role of humility in organizational success, common failure points in organizations, and the future of impactful startups.

Melissa Kwan, CEO of eWebinar, discusses bootstrapping vs. venture capital funding. Topics include understanding customers, challenges of building a product, determining financial goals, personal branding, self-serve options, and vertical SaaS businesses.

Chris Tottman and Richard Blundell discuss their operator's perspective on investing in successful businesses. They highlight the importance of being customer-focused in a narrow market and the dangers of going too broad. They also explore the metrics to evaluate businesses and the significance of where customers communicate and recommend.

Former CPO of Eventbrite, Casey Winters, shares insights on career transitions, organizational alignment, and the future of technology. Topics include: dealing with misalignment, the impact of company strategy, taking care of OKRs, planning the return to work, technology and distribution changes, and the future of advertising and SEO.

John Cutler, best systems thinker discusses the misconceptions of efficiency and productivity, the challenges of scaling businesses, the complexity of knowledge and expertise, the importance of consistency, the influence of random rewards on habit formation, and tracking habits and behaviors in business.

Jason Fried, CEO of 37signals, shares his contrarian approach to business: don't overcomplicate decisions, be confidently wrong, double down on what works, and trust your intuition. They discuss the significance of self-discovery, cutting and editing in business, and the importance of long-term value, customer success, and employee satisfaction in creating a better product. They also challenge traditional evaluation methods and emphasize the unpredictability of businesses and markets. Overall, the podcast focuses on simplicity, customer success, and making progress in business.

Adam Fishman, Expert in yearly planning and leadership perspective, joins Leah to discuss rolling planning, managing risks and human component, typical planning mistakes, understanding direct manager's goals, and what to do if you don't agree with company's strategy.

Andrew Davies, CMO at Paddle, on the latest learnings on monetization and pricing. A topic that is still underserved because almost no one has good, conclusive data about it. Paddle does, and Andrew is sharing a lot of actionable advice on:- Willingness to pay- Changing monetization often- How to not incentivize anyone the wrong wayOne of my favorite episodes to date!Timestamps:06:20 Insights from the latest pricing report, analyzing outliers that “make it”09:00 Having access to one of the biggest data stacks about monetization and how Paddle structured itself as a PLG business step-by-step12:45 How to figure out how much you should charge for your product?19:45 How to figure out “willingness to pay”. Cuddling with Chaos24:00 Between Acquisition, Retention, and Monetization…  Few companies are getting pricing right. Those that change it often have an 82% better ARPU30:40 How do you get sales on board to play along to be okay with changing monetization36:00 “We make sure there is no incentive for anyone in the company to get a customer on the phone over self-serving, including sales”40:55 Getting payment methods, currency, and regional acceptance right.44:30 We are moving away from the “VC funded or dead” dream.50:15 What does it feel like to be really “successful” and not to spiral “getting there”54:00 Having no clue what you are doing is an opportunity, not a weakness to cover58:45 Trends: Customers want everything faster and cheaper.Leah on Linkedin / Twitter / Youtube

Brian Donohue, product executive at Intercom, discusses the challenges of building AI products and the unpredictability of outcomes. They explore the importance of customer service, tying business and technology together, and creating artificial micro-markets. They also delve into the uncertainty of AI displacing jobs and the future impact of AI advancements.