Summary Chess.com has grown from being a simple chess service to a thriving 150 million ARR business. The company has focused on making chess accessible to everyone through services around a product that hasn’t changed in centuries. We touch on the challenges of scaling a company and the role of titles and leadership in an organization and how many times Erik wanted to give up in the process. Erik talks about the need for passion and love for the product, and the importance of hiring...

Motivation, forming habits, managing time, and why it’s important to know how much you enjoy solving problems with Jason Fried. Jason is really special to me and a 2nd time guest. Whenever we go at it, there are two worlds clashing in the best way possible. We are both never content with traditions and challenge the status quo; we just often disagree on how to challenge them while we agree on the first principles behind it all. Our fight about calendars and time management is one of my...

Summary The conversation with Mike Weir, former CRO of G2, focused on reducing churn and driving expansion revenue. At G2, they used a churn model with 14 highly correlated variables to identify at-risk customers and prioritize actions for the customer success team. We also discussed the importance of product and marketing in customer education and engagement and how to align sales, customer success, product, and marketing in a product-led growth (PLG) organization. The discussion also...

Anthony Pierry, partner at FletchPMM, focuses on messaging for early-stage B2B SaaS startups, and he brought a lot of actionable knowledge on how to do it right to the ProducTea. Summary I talk with Anthony about how to focus and narrow down your target audience and how to communicate it through your value proposition. How do we cross the chasm between the early-stage value proposition and the bigger market we want to reach? How do we use qualitative feedback in these high-risk and low-data...

Adam Robinson, CEO of Retention.com & RB2B, is the CEO who builds in public on LinkedIn and is crushing it by discovering the power of product-led growth as he is doing it. He’s very specific about what works and what doesn’t and how he got started. He explains the power of organic reach through LinkedIn and building a personal brand through social media, particularly LinkedIn, and how important it is to not be too rigid in your assumptions. Adam shares his experience with video content...

Casey Hill is a Senior Growth Manager at ActiveCampaign, Institutional Consultant, and Founder. More importantly, he’s incredibly actionable and smart on LinkedIn around B2B Email channels, and that’s why I wanted to have him on the podcast. Summary We talk about how to approach Email, how to use it from the ground up to drive meaningful business and how to measure it. How to balance different channels, such as influencers, podcasts, and newsletters. What IS good content and should you...

Julie Zhuo, Co-Founder @ Sundial, Author of THE MAKING OF A MANAGER, ex-VP Design @ FB Summary Intuition and hiring is an uncomfortable topic. We should be rational, have reasons for why we choose to work with someone or not. When should we trust our gut feeling? When is it time to step back and say, no. I go with the hard facts? In the end it’s all about building an honest relationship as a leader with our peers and what kind of person you want to be. Afterall, we spend a huge time with our...

Summary Jamie Gier, - CMO at DexCare and former Director of Product Marketing at Microsoft - and I talk about the importance of understanding the customer and the challenges of marketing in regulated industries. We also touch on the process of learning marketing, the concept of account-based marketing in B2B, and how to connect it to revenue through ROI cases for our customers. The conversation concludes with a focus on relevant outreach and communication concepts with the aid of...

Summary Peter Walker, Head of Data Insights at Carta discusses with me various aspects of startup funding and investment. We explore the value of small angel investments, the obscurity of startup funding letters, the selectivity of startup advisors, and the potential of angel investments as marketing assets. We also touch on the excitement for the future of startups, the impact of accelerators and venture studios, and the importance of distribution and growth and whether a downround really is...

Why is ruthless focus the most important skill in B2B, and why is it so hard to get right?  As the CEO of a banking service that focuses on the impact of cashflow mismanagement on small businesses, he knows what it means when people only focus on what’s fun to them in a business and the price they pay for that. We talked about the decision to seek VC funding and how he built resilience and dealt with negative emotions in tough times. What it means to him to deliver more value than just being...

Jeff Gothelf, one of the most critical voices around OKRs and being outcome-driven, sat down with me for an hour-long amazing conversation: We touch on why using OKRS is useless if you can’t admit when you are wrong and be open to feedback from your teams. How do you set outcome-driven goals for exploratory research and the role of humility in organizational success? Why shipping something does not mean you’re adding value. Finally, we discuss common failure points in organizations and the...

Summary Melissa Kwan, CEO of eWebinar and serial bootstrapper, discusses the challenges and benefits of bootstrapping a business versus seeking venture capital funding. She is the poster child for urging founders to focus on real customer feedback and paying customers without loading up on VC problems.  We discuss the importance of understanding the customer, personal goals and ambitions, the challenges of building and scaling a product, defining success and financial goals, the desire for...

Chris Tottman and Richard Blundell joined me for a fantastic conversation about how they think from their own operators’ perspective when it comes to investing in successful businesses and their people. Why you should not talk to investors who never went through the personal pain of failing and why it most of the time comes down to the basics of running a successful business: Being obsessed with customers in a narrow marketProduct Market Fit is not just having a great product in a great...

A Journey I’m in the middle of as well: How to transition from senior leadership to taking care of yourself to the moment where you enter again. Casey Winters, ex-CPO Eventbrite, walks through the entire journey and how he thinks about our current markets; our technology is drastically changing while the new distribution channels have not developed yet. Why he is waiting before making high-conviction bets for his career in 2023 Timestamps: 08:10 Why Casey is stressed out and scared of...

John Cutler is the best systems thinker I know. Whenever we talk, there’s a beautiful meta-analysis around systems happening. Why do we work the way we do? Why can we not figure out how to run businesses efficiently if we do it so often? Why do inexperienced, brilliant people constantly get into trouble, and how do they get out of it?Individual vs. team habitsHow much of our decisions is gut vs. objectivityLeadership porn and its connected biasesTimestamps: 6:50 How people throw words like...

Jason Fried, Co-founder and CEO of 37signals (Basecamp with a valuation of 100 billion, no really ;D), is one of the most positive, successful, forward-looking people that I got to know. He doesn’t care about retros and dwelling on the past and constantly pulls forward without looking too much at what others might think. This amazing episode ended up being a look into the mind of a successful contrarian who appreciates the beauty of simplicity in business. * Don’t overcomplicate decisions...

Adam Fishman and I elaborate on how we look at the inevitable yearly planning exercises from an operative and leadership perspective. How to do a rolling planning instead of doing the depressing exercise of wasting everyone’s time for a month at the end of each year: Managing risks and the human component in planningThe typical mistakes you should avoidWhat to do if you don’t agree with a company's directionTimestamps: 04:20 Leah’s take: The operator’s perspective of yearly planning, fuzzy...

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 way One 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...

This episode gave me a lot of peace of mind. Intercom is dealing with the exact same problems that we all have when building around and with AI. Estimations are impossible and things that are feeling impossible are possible the day after. Brian sat together with me to talk about it all including Intercom’s coming-of-age story and how they look at customer service through this new distorting lense of AI and Machine learning that is rocking our boat. It’s a great learning piece on anything...

Season 3 of the ProducTea: We spill the tea on how to Go to Market through Product-led Sales and Product-led Growth in B2B and the realities of senior leadership. Mike used to be my manager and quickly became one of my most important mentors through the years. In this very personal episode with a lot of inside stories, we talk about it all. From experiences at Smallpdf where rapid scaling pains set in and how we experienced them from the perspective of the CPO - him, and me - the core...

Season 3 of the ProducTea: We spill the tea on how to Go to Market through Product-led Sales and Product-led Growth in B2B and the realities of senior leadership. Carilu’s wheelhouse starts where mine usually begins to end. She’s an accomplished advisor to big-scale hypergrowth companies and has a way with words. How do we think of problems at different stages? How do we set ourselves up so we have a chance of experiencing different stages if nobody hires us for them? Why is storytelling so...

Season 3 of the ProducTea: We spill the tea on how to Go to Market through Product-led Sales and Product-led Growth in B2B and the realities of senior leadership. I followed David’s succinct learnings as a Gartner Analyst around PLG for quite some time and you’ll get to know why. He has a way with words. Talking about PLG in a B2B context usually lacks nuance and tactical tips. Not with David, we touched on so many different topics from interactive demos to the most common misconceptions when...

Season 3 of the ProducTea: We spill the tea on how to Go to Market through Product-led Sales and Product-led Growth in B2B and the realities of senior leadership. This episode is very difficult to summarize, we touch on highly tactical methods on how to combine offline and online methods to drive communities. Why they are key to breaking into difficult markets and how Lobo did it in detail. The first half of the podcast is an inspiring origin story from Lobo from the slums he came from to the...

Season 3 of the ProducTea: We spill the tea on how to Go to Market through Product-led Sales and Product-led Growth in B2B and the realities of senior leadership. Benjamin Lamson had a great exit and no more sleep due to having a baby at home. His insecurities with rising success, how he manages to deal with it day by day, and how Jobs-to-be-done can be brought into an early-stage company. A great conversation with a sales leader turned product-led growth lover! Timestamps: 05:00 Are you...