In this book, Gartner argues that hypomania, characterized by heightened energy, creativity, and ambition, has been a driving force behind many of America's most innovative and successful individuals. He examines historical figures such as Christopher Columbus, Alexander Hamilton, and modern-day entrepreneurs like Ted Turner, suggesting that their hypomanic tendencies contributed to their remarkable achievements. Gartner also emphasizes the importance of managing hypomania to prevent it from escalating into full-blown mania, and advocates for recognizing and nurturing the positive aspects of this condition rather than stigmatizing it.
In this groundbreaking book, David Deutsch argues that explanations have a fundamental place in the universe and that improving them is the basic regulating principle of all successful human endeavor. The book takes readers on a journey through various fields of science, history of civilization, art, moral values, and the theory of political institutions. Deutsch explains how we form new explanations and drop bad ones, and discusses the conditions under which progress, which he argues is potentially boundless, can and cannot happen. He emphasizes the importance of good explanations, which he defines as those that are 'hard to vary' and have 'reach', and argues that these explanations are central to the Enlightenment way of thinking and to all scientific and philosophical progress.
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
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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
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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.
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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/
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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
How I Invest with David Weisburd 
