E164: How I Built a Billion Dollar Company by Failing Fast w/Howard Lerman

Howard Lerman has founded six companies and taken one public—he's a relentless builder with an obsession for speed, innovation, and execution. Currently the Founder and CEO of Roam, Howard is reimagining what the modern workplace looks like by building the “Office of the Future,” where AI agents work alongside humans to accelerate output. In this episode, Howard joined me in How I Invest Podcast to share the frameworks and mental models behind how he leads teams, scales product-market fit, recruits S-tier engineers, and instills an almost maniacal level of urgency and creativity across the organization. We talk about what it means to enter "founder mode," why professional managers may soon be obsolete, and how cultural memes shape everything from product design to company mission. If you’re building, investing in, or simply curious about the future of work and AI-native companies—this episode is a must-listen. Highlights: Why being a "cockroach" founder is a superpower in company survival How Roam is using AI agents to automate workflows and enable 24/7 productivity The "Office of the Future" and why presence matters—even virtually How to spot S-tier talent (and why they might be a pain to manage) Why product-market fit should be the last thing a founder gives up Howard’s nightly “founder mode” ritual and obsession with speed The evolution of memes and how they shape product adoption The dirty secret about obsession: it’s more about the people than the mission -- Guest Bio: Howard Lerman is a serial entrepreneur and currently the Founder and CEO of Roam, a startup building the "Office of the Future" by integrating AI deeply into the work experience. Previously, he was the Founder and CEO of Yext (NYSE: YEXT), which he led from startup to IPO. He is known for his strong views on founder-led companies, speed as strategy, and hiring only the best—what he calls "S-tier" talent. Howard is also an early adopter and evangelist of AI agents in the workplace. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @JuniperSquare for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Howard Lerman: @howard LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Howard Lermar: https://www.linkedin.com/in/howardlerman/ Links: Roam: https://www.linkedin.com/company/roam-hq-inc/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:55) Applying cockroach principles and pivoting at Yext (3:38) Company structures, founder authority, and employee empowerment (6:16) Instilling speed and operating at warp speed in a company (10:01) Delegating and recruiting top talent (17:10) Building urgency and an obsession for success in teams (21:11) Howard Lerman's formative experiences and co-founder relationships (24:12) The role of memetics and memes in business (28:31) Closing remarks