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.
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.
When You Need a Fractional COO and Don’t
It’s usually a bad sign if a product claims that it can do everything for everyone. Swiss Army Knives aren’t really great knives at all, but they do have a Job to be Done—they make great gifts even if they’re barely ever used afterward. I try not to fall into this trap. This blog posts lays out some of the signs that you don’t need the help of a fractional COO at all.