Lessons from Failure: Embrace Setbacks

Is traditional valuation dead for the biggest winners of the AI era? Or have investors simply been looking in the wrong place? In this episode, I talk with Dan Ives, Managing Director and Global Head of Technology Research at Wedbush Securities, and one of Wall Street’s most followed tech analysts. Dan has covered the software and technology sector for 25 years, becoming known for his bold, high-conviction calls on Tesla, Nvidia, Microsoft, and Palantir long before they became consensus. We break down why Dan calls Tesla the world’s leading “physical AI” company, why he thinks AI is the largest tech transformation in 40–50 years, what investors miss when they rely only on spreadsheets, and how his pattern-recognition framework helps him spot multi-baggers years before the herd.

Highlights:

• Why he views Tesla far beyond autos; autonomy, robotics, robo-taxis, and multi-trillion-dollar upside.
• Why he believes AI is a 40–50 year mega-cycle with second- and third-order winners.
• Why do great companies look expensive every year until suddenly they don’t.
• On pattern recognition, global customer conversations, and signals that never show up in models.
• Lessons from 2008, 2022, and sticking with calls through volatility.
• Why Nadella, Musk, Karp, and Lisa Su are misunderstood and mispriced by Wall Street.
• His 1–10 conviction framework and how he sizes up when inflection happens.
• Where he’s looking for the next multi-baggers in the AI supply chain.
• How setbacks early in his career reshaped his investing worldview.
• His role as Chairman of ORBS (EightCo Holdings) and Worldcoin-aligned authentication.
• Why he partnered with Snow Milk on a fashion collaboration and how “owning who you are” fuels differentiation.

Guest Bio:

Daniel Ives is the Managing Director and Global Head of Technology Research at Wedbush Securities, where he has been a senior equity research analyst covering the technology sector since 2018. Dan has spent 25 years on Wall Street following software, cloud, cybersecurity, mobile, and the broader enterprise tech ecosystem.

He is also the Chairman of EightCo Holdings (ORBS), focused on authentication and digital identity infrastructure aligned with the emerging AI era.

Dan is one of the most sought-after tech experts globally, regularly appearing on CNBC, Bloomberg, BBC, Fox Business, ABC, NBC, Sky News, France 24, NPR, and many other global outlets. He is frequently cited in The Wall Street Journal, The New York Times, Financial Times, Barron’s, Time, The Telegraph, and other major publications.

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.

#venturecapital #vc #startups #openlp #assetmanagement

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Daniel Ives: https://www.linkedin.com/in/daniel-ives-542321a8/

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

(0:00) Preview (1:17) Dan Ives on the AI revolution, Tesla's market dominance, and valuation methodology (5:10) The importance of long-term vision and global insights in tech investing (10:52) The role of retail investors and the impact of market sentiment (14:25) The significance of true believers and early adopters in investments (16:13) Recognizing when an investment thesis is wrong and adjusting strategies (22:32) Investment sizing, portfolio construction, and utilizing customer feedback (26:16) Psychological biases and their effects on investor confidence (27:06) Leveraging social media and conferences for investment insights (28:31) Understanding power law returns and second/third order effects in the market (32:20) Evaluating investment success: hit rates and the role of outliers (34:09) Influencing stock narratives and decisions at the board level (37:21) Identifying mispriced founder-led companies and embracing failures (43:41) Dan Ives' personal background and approach to maintaining conviction (47:48) Future projects at Wedbush and personal ventures (49:19) Closing remarks