One big decision a year investing philosophy

What if the most powerful investment strategy isn’t optimization but making one truly great decision each year? In this episode, I talk with Joshua Browder, Founder and CEO of DoNotPay and a solo pre-pre-seed investor, about how momentum, conviction, and first-belief investing create outsize outcomes. Joshua shares how DoNotPay became a profitable, dividend-paying AI consumer company with a team of 14, why he focuses on backing founders before they look credentialed, and how acting decisively on binary choices can matter more than years of incremental improvement. We also explore why grit beats IQ, how momentum keeps startups alive, and what it really takes to be a founder’s first believer.

Highlights:

• Why “one big decision per year” matters more than constant optimization
• How DoNotPay scaled to millions of users with a tiny team
• Why profitable companies can still be venture-scale
• Grit vs. IQ in predicting founder success
• The power of being the first believer, not the fastest follower
• How momentum determines survival at pre-seed
• Why binary decisions beat marginal improvements
• How Joshua creates momentum for founders operationally
• Why founders should build for meaning, not resumes
• How portfolio construction changes at pre-pre-seed

Guest Bio:

Joshua Browder is the Founder and CEO of DoNotPay, an AI consumer rights platform that has automated over 200 legal and financial processes and won more than two million cases for users. He founded the company while studying computer science at Stanford before leaving to join the Thiel Fellowship. Joshua is also an active early-stage investor, backing first-time founders before they become obvious, and has invested in over 150 companies including Figma, Mercury, and Owner.com. His work focuses on helping people fight institutional friction while building profitable, mission-driven businesses.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Joshua Browder:

LinkedIn: https://www.linkedin.com/in/joshua-browder-b0b573116/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (0:39) Business model, profitability, and startup myths (2:56) Transition to venture capital and Thiel Fellowship experience (6:02) Reflecting on investment decisions and philosophy (9:47) Evaluating founders and the one-person accelerator approach (14:23) Traits of successful entrepreneurs and startups as momentum machines (18:16) Founders’ roles and commitment evaluation (23:43) Portfolio construction and key decision-making in early-stage investing (27:22) Productizing tasks and balancing tactical vs strategic thinking (30:36) Closing remarks