What if the fastest turnaround move isn’t a strategy deck—but a calendar full of one-to-ones?
Dylan Serota didn’t start as CEO. After co-founding Terminal inside the Atomic venture studio and serving as Chief Strategy Officer, he stepped into the top job during a brutal reset—RIFs, salary cuts, and a near refounding. His first act: meet every single employee one-on-one to rebuild trust, alignment, and momentum.
In this conversation, Dylan shares the inflection points of moving from “influencing strategy” to owning the call, how he eliminates low-stakes battles to focus on conflict where it matters, and why he runs the business by focusing on inputs over outcomes—execute the right plays, and “the score takes care of itself.” He also breaks down his cadence with the board (metrics pre-reads + a 2-page memo) to maintain high-trust governance and low-tax oversight. And as a father of three, he reflects on how his family has reshaped his time, humility, and approach to listening at work.
Why it matters: If you’re leading through uncertainty, Dylan’s team-first playbook—skip-levels, time-boxed debates, clear CEO decisions with rationale, and relentless focus on controllables—helps you earn commitment and move faster with fewer regrets.
What we cover: co-founder dynamics inside a venture studio, leading in “wartime,” turning conflict into alignment, triggers and information flow, and building a board relationship on transparency rather than window dressing.
About the guest:
Dylan Serota is the Co-Founder and CEO of Terminal. Before becoming CEO, he served as Chief Strategy Officer and helped build the company after formative years at Eventbrite. Dylan led Terminal through a major reset by putting the team first, operating with decisive, data-driven focus, and rebuilding for profitable growth.
About the Host:
Dave Osh is a transformation catalyst dedicated to evolving leadership potential, creating a ripple effect of unity in our divided world. He leads large-scale leadership transformation programs that drive meaningful change for individuals, teams, organizations, and society.
Company website: https://www.varlinx.com/
Personal website: https://www.daveosh.com/
LinkedIn: https://www.linkedin.com/in/daveosh/
Book: https://www.amazon.com/CEO-Potential-...
TEDx: Overcoming Bias to Unite Our Divided World
