18 Companies with 50–200 Employees
Learn from founders and CEOs who have built successful businesses with teams of 50–200 people

Paul Copplestone
Co-Founder & CEO
In this interview, Paul Copplestone, Co-Founder and CEO of Supabase, outlines the architectural shift occurring as generative artificial intelligence democratizes software development globally. He analyzes the evolution of developer platforms, the rising demand for personal databases, and scaling open-source Postgres infrastructure to over thirteen million users. Copplestone delivers essential strategic lessons on designing agent-first developer experiences, maintaining transparent developer pricing, and fostering an egoless engineering culture through rapid operational scaling.

Jason Cozens
Founder & CEO
In this interview, Jason Cozens, founder and CEO of Glint Pay, joins Andy Schectman on Little by Little to discuss the resurgence of physical gold and silver as legal tender currency across the United States. He explains how state-level constitutional initiatives in Texas and Florida are revitalizing sound money, how fintech bridges allocated vaulted bullion with everyday debit card transactions, and why global debt pressures are driving economic resilience.

Anton Oika
Co-Founder & CEO
In this interview, Anton Osika, co-founder and CEO of Lovable, explains why the era of vibe coding is over and the era of serious AI-powered business building has begun. He shares how Lovable grew to a 13 billion USD valuation in under two years, why domain expertise and closeness to a problem matter more than technical skills, how to validate a business idea with ten customers, and why creativity is now the most important differentiator as execution becomes easier for everyone.

Paul Graham
Co-Founder
In this interview, Y Combinator co-founder Paul Graham reflects on twenty-one years of startup acceleration and forty-seven YC batches. Graham explores the nature of founder ambition, defines the elusive quality of formidability, and discusses why day-to-day motivation stems from fear of failure rather than wealth. He also analyzes whether lean startups remain viable, shares his perspective on the jagged artificial intelligence frontier, and explains how early-stage batch networks accelerate company growth.

Jake Karls
Co-founder & Chief Rainmaker
In this interview, Mid-Day Squares co-founder and Chief Rainmaker Jake Karls describes the unconventional journey of building a disruptive snack brand. Karls shares insights on defining the Rainmaker role, transitioning away from weak management positions, and using weekly mediated therapy to preserve family partnerships. He also details the operational decisions to build custom manufacturing, the strategies for retail placement in Walmart and Costco, and the lessons learned from managing burnout and raw material price shocks.

Krissy Cela
Founder & Creative Director
In this interview, Oner Active founder Krissy Cela shares her journey from waitressing and compiling workout PDFs on a student laptop to building a bootstrapped activewear brand generating over two hundred million dollars in annual revenue. Cela discusses the challenges of early business partnerships, the importance of cycle-based female product design, the transition to a global brand presence, and the necessity of assertive leadership and operational structure for company scalability.

Garry Tan
President & CEO
In this interview, Y Combinator President and CEO Garry Tan outlines the new paradigms of software development driven by vibe coding and AI agents. Tan shares lessons from his early career regrets, recounts Peter Thiel's attempt to recruit him for Palantir, and discusses how Y Combinator democratizes access to Silicon Valley. He also details the transition from traditional SaaS to agentic workflows, the role of security tools like Crab Trap, and San Francisco civic reforms.

Harjot Gill
Co-founder & CEO
In this interview, CodeRabbit co-founder and CEO Harjot Gill discusses the evolution of AI-powered code reviews and automated validation tools. Gill shares insights from his past entrepreneurial exits, details the engineering challenges of managing token usage and ensemble model costs, and explains how CodeRabbit achieved rapid market adoption through open source communities. He also outlines the company's future vision for team-based collaborative intelligence across tools like Jira and Slack.

Chris Best
Co-founder & CEO
In this interview, Substack co-founder and CEO Chris Best discusses the challenge of AI slop, the premium on human attention, and Substack's new transparency tooling. Best shares insights on the rise of generated long-form content, the integration of Pangram text detection, and the dynamics of co-writing with large language models. He critiques platforms that automate authorship, applying economic models like Baumol's cost disease to predict how value shifts when content production becomes free.

Cathie Wood
Founder, CEO & CIO
In this interview, ARK Invest founder and CEO Cathie Wood discusses Bitcoin bottoming and emerging into a broad multi-year uptrend. Wood details critical macroeconomic metrics, including token spending drops, auto delinquency trends driven by ride-sharing adoption, and housing market affordability challenges. She outlines how converging technologies like artificial intelligence, public blockchains, and robotics act as structural deflationary forces, boosting global economic productivity while lowering national budget deficits.

Collin Kettell
Founder & CEO
In this interview, Palisades Goldcorp founder and CEO Collin Kettell discusses their unique warrant-centric resource investment strategy at the Rick Rule Symposium. He details the transition from managing New Found Gold to building a diversified portfolio of 330 companies holding 1.7 billion warrants across gold, silver, copper, and critical metals. Kettell explains the leverage of long-dated warrants during a mining bull market and highlights key holdings like Made in America Gold and Radio Fuels.

Cobi Blumenfeld-Gantz
Co-Founder & CEO
In this interview, Chapter co-founder and CEO Cobi Blumenfeld-Gantz discusses the company's rise to a $3 billion valuation in the senior health navigation market. He outlines their transition to an AI-native infrastructure, the power of an unbiased advisory model, and how they tripled revenue with flat headcount. Blumenfeld-Gantz also shares insights on strategic wealth management partnerships, legislative advocacy in Washington, and Chapter's ultimate vision to become the comprehensive super-app for retirement.