Journey of a Founder: Series B to Series C—Scaling Challenges and Leadership Imperatives
Every startup that reaches Series B has proven something, but sustaining growth, scaling teams, and building durable systems is a whole new test. What changes at this stage, and how do founders evolve to meet it? In this founder/operator roundtable, we dive into the next phase of the journey: from Series B to Series C. We cover what shifts in mindset, systems, and leadership.
Event 2—Part 2: Hosted by John Gauch and Jimmy Malik.
Journey of a Founder: Series A Is a Reckoning—Operator Imperatives for Getting to Series B
The Journey of a Founder series continues. You’ve raised a Series A. You’ve got early traction and capital to grow. But now the real work begins. What does it feel like to lead a company through this phase, and what actually helps you reach Series B? In this founder/operator roundtable, we explore what happens after the early wins, from hiring and trust-building to evolving your founder role and avoiding the ops pitfalls that can sink momentum. This is the messy middle, what I sometimes call “the reckoning.”
Event 2—Part 1: Hosted by John Gauch and Jimmy Malik.
Journey of a Founder: A Startup Story
Every startup faces pivotal moments—turning an idea into a product, finding early customers, securing funding, and scaling successfully. But what challenges arise at each stage, and how do you navigate them? Check out a recording or transcript of our roundtable with two experienced founders. This is an online event where we break down the founder’s journey from Inception to Series A—exploring key milestones, common challenges, and actionable strategies to move forward.
Event 1: Hosted by: John Gauch and Jimmy Malik.
Deadlocked? Use “Forced Empathy” to Resolve Conflicts and Strengthen Your Startup Team
Startup environments are high-stakes. Team deadlocks can undermine progress and morale. Make the wrong decision, and that could be the end of it all. This post discusses “forced empathy,” an active perspective-taking technique to break deadlocks by encouraging team members to advocate for each other’s viewpoints, fostering trust and collaboration, and guiding teams toward sounder decisionmaking.
Essential Leadership Skills for 2024: What They Are and Why Every Leader Needs Them
Building a successful startup is one of the hardest challenges you can take on. Read about and develop essential leadership skills for 2024 and beyond, including self-awareness, strategic thinking, and adaptability, to improve your odds of succeeding.
Key Strategies for Business Growth: 10 Steps to Expand and Thrive
This month I discuss effective strategies for business growth, with special emphasis on startups. I cover topics from market penetration to digital transformation. The content will help CEOs and founders develop their own plans to expand and thrive.
50 Top Apps, SaaS Solutions, Services and Sites for Startups
Founders and CEOs are very demanding when it comes to the tech they use to run their businesses. They have high expectations. They should, too. See how this list of apps, SaaS solutions, services, and sites lines up with your tech stack and hopefully get some new ideas for what to add or switch.
Updated September 17, 2026, including vetting for recent AI developments.