Podcast Summary: How I Invest with David Weisburd

Episode 242: Gen Z, Dopamine, and the New Investing Playbook

Date: November 14, 2025
Host: David Weisburd
Guest: Steven Jiang, Founder & CEO of Dubb

Main Theme

This episode explores how the rise of Gen Z, the dopamine-driven culture of investing, and platforms like Dubb are reshaping retail investing. Steven Jiang, who dropped out of Harvard at 18 to build Dubb—a regulated copy-trading platform—discusses the cultural, technological, and psychological factors creating a new investing playbook. The conversation covers meme stocks, intergenerational wealth shifts, the mechanics and culture of Dubb, and broader philosophical lessons for founders and investors.

Key Discussion Points & Insights

1. Genesis of Dubb & Copy Trading

• What is Dubb?

  • Dubb is a regulated copy-trading platform, allowing users to automatically follow and copy the portfolios and trades of proven investors, including former hedge fund managers and influential traders.
  • "Most retail investors will never get good at investing… There’s no better thing than just following what proven experts are doing in the markets." – Steven Jiang [00:06]

• Democratizing Wealth Management:

  • The model mimics what wealthy individuals do (hire experts), making it accessible to anyone with $100.
  • "We want to enable anyone with $100 to do that same experience." – Steven [00:44]

2. Rise of Retail & Cultural Shifts in Investing

• Explosion in Retail Trading

  • Retail’s share of trading volume has doubled in 10-15 years, driven by brokerages like Robinhood and the gamification of finance, with social media amplifying trends and memetic behaviors.
  • "Now we're able to invest for the very first time and streamline... That accessibility Cambrian explosion was one of the first parts." – Steven [01:01]

• Gen Z & Dopamine Investing

  • COVID-19, stimuli, and meme stock euphoria catalyzed a generation to invest like entertainment, driven as much by FOMO and social trends as fundamentals.
  • "The memetic desire and FOMO where… your dumbest friend was now making $100,000 in Dogecoin. Who's not going to give that a shot?" – Steven [02:36]

• Downside Realities

  • Choppiness post-2021 revealed losses for the majority—80% of GameStop investors lost money overall despite hype.
  • "80% of people who invested in GameStop actually lost money in totality." – Steven [03:15]

3. Founder Journey & Building Dubb

• Dropping Out, Building Grit

  • Steven left high school to build his first startup (which failed but taught him resilience).
  • "My first time leaving… was in high school. So I left high school when I was 16 to do my first company." – Steven [03:53]
  • Prior investor relationships de-risked the decision to leave Harvard and build Dubb.

• Scaling & Leadership Evolution

  • Early leadership mistakes included over-micromanaging and using fear-based motivation, inherited from a strict upbringing.
  • "What got me here is not going to get me to where I want to go… I was the worst micromanager." – Steven [07:28]
  • Transitioned to hiring experienced executives and trusting teams, leading by inspiration rather than fear.

• Culture at Dubb

  • Culture prioritizes intrinsic motivation, personal agency, and high expectations.
  • "My policy now… I don't inspect first. I expect greatness out of you." – Steven [09:31]
  • Anti-selling in interviews to filter for true grit and buy-in.

4. Gen Z & The $100 Trillion Wealth Transfer

• Behavioral and Psychological Changes

  • Gen Z sees investing as the primary path to wealth, with higher risk appetites and desire for agency and the “dopamine hit.”
  • "Gen Z believe that the fastest way to become a millionaire is through investing." – Steven [12:23]

• Risks & the Onus of Platforms

  • Access alone isn’t enough; education and smarter decision-making tools are critical to avoid repeated cycles of losses.
  • "You're giving people the keys to the casino, but you're not teaching them how to play poker." – Steven [13:41]

5. How Dubb Works: Mechanics & Value Proposition

• Portfolio-Centric, Transparent Copy Trading

  • Users deposit, browse verified managers or “creators,” and copy their portfolios in one click.
  • Full trade histories are visible, removing the ability to “fake” track records.
  • "With the tap of button you can follow everything they do in their portfolio automatically." – Steven [14:36]

• Social Dynamics and Influencer Economy

  • Investing is now intertwined with influencer trust—just like Yelp or Instagram for product choices.
  • Pushes more people into owning stocks, countering the wealth gap.

6. The Nancy Pelosi Meme-Trade Phenomenon

• Operationalizing Viral Trading Strategies
  • Users can copy U.S. politicians’ disclosed trades, e.g., the “Nancy Pelosi Portfolio” (based on required filings under the STOCK Act).
  • "Nancy Pelosi… since inception… up 188%. We made our customers tens of millions of dollars through copy trading Nancy Pelosi’s picks." – Steven [21:10]
  • These viral strategies drove immense early traction, but Dubb is focused on long-term marketplace diversity.

7. Meme Stocks, Social Media, and Retail Power

• Social-Driven Market Movements

  • Platforms like Reddit and Dubb are letting individuals collectively move markets (e.g., GameStop, OpenDoor), sometimes overpowering major hedge funds.
  • "The little guys finally come to the table… individuals are many ways eating the institutions." – Steven [24:33]

• Momentum & Intrinsic Value

  • Meme stocks sometimes translate momentum into real capital: buybacks, new business lines, creative capitalization.
  • "When your stock goes up so high… you can leverage that stock price to do a lot of things." – Steven [26:33]

8. Where Is the Real Alpha?

• Top Traders’ Edge

  • Edge comes from focusing on less-followed small/micro caps, leveraging intuition, and using social influence to drive collective action—akin to “crowdsourced activism.”
  • "There will always be alpha in smaller cap companies because there’s just less attention." – Steven [28:04]
  • "When you can do something like OpenDoor… galvanize them behind your views." – Steven [29:03]

• Skill vs. Marketing

  • Dubb separates marketing ability from investing skill by making performance transparent.
  • "On Dubb, you can’t fake your track record. It’s fully transparent." – Steven [23:52]

9. Personal Networks, Information Diet & Fulfillment

• Building Advisory Networks

  • Steven built his network via curated dinners, prioritizing deep relationships over broad ones.

• Continuous Learning

  • Utilizes ChatGPT, audiobooks, and philosophy (“The Myth of Sisyphus” by Camus) to synthesize new ideas, embrace struggle, and stay grounded.
  • "You’re the average of five people you spend the most time with." – Steven [31:41]
  • "One must imagine Sisyphus happy." – Myth of Sisyphus quoted by Steven [33:44]

• Gratitude & Mindfulness

  • Practices walking meditation, Sam Harris' Waking Up app, and advocates operationalizing gratitude.
  • "Your words are the house you live in." – Steven [35:19]

10. Lessons for Founders & Investors

• Reinvention & Feedback

  • The necessity of evolving management style, embracing feedback, and recalibrating ambitions.
  • "What got you here will not get you to where you want to go." – Steven [36:31]

• Decisionmaking Under Pressure

  • The importance of patience, emotional control, and cooling down before big decisions.
  • "You feel it in the gut… Wait an hour, wait 20 minutes… you’re going to make a better decision." – Steven [37:57]

• On Ambition & Reality

  • Over-ambition can be self-defeating; compounding simple actions wins long-term.
  • "The beauty of compounding… probably the most powerful thing you can do." – Steven [41:49]

Notable Quotes & Timestamps

• “Most retail investors will never get good at investing… There’s no better thing than just following what proven experts are doing in the markets.”
  — Steven Jiang [00:13]

• “The memetic desire and FOMO where… your dumbest friend was now making $100,000 in Dogecoin. Who's not going to give that a shot?”
  — Steven Jiang [02:36]

• “You’re giving people the keys to the casino, but you’re not teaching them how to play poker.”
  — Steven Jiang [13:41]

• “My policy now… I don’t inspect first. I expect greatness out of you.”
  — Steven Jiang [09:31]

• “On Dubb, you can’t fake your track record. It’s fully transparent.”
  — Steven Jiang [23:52]

• “You’re the average of five people you spend the most time with.”
  — Steven Jiang [31:41]

• “What got you here will not get you to where you want to go.”
  — Steven Jiang [36:31]

• “One must imagine Sisyphus happy.”
  — Steven quoting Camus [33:44]

Key Segments (Timestamps)

• [00:06] – Dubb’s purpose, copy trading explained
• [01:00] – Rise of retail and the “accessibility Cambrian explosion”
• [02:36] – The COVID boom & dopamine investing
• [07:28] – Lessons from scaling and management style
• [12:23] – Gen Z, wealth transfer, and new attitudes toward risk
• [14:36] – Step-by-step Dubb user experience
• [21:10] – Copy trading Nancy Pelosi’s public trades: market impact
• [24:33] – Meme stock phenomenon and social media’s role
• [28:04] – Where real alpha lives in today’s market
• [31:41] – Building a deep advisory network
• [33:44] – The Myth of Sisyphus and meaning in founder life
• [35:19] – The power of gratitude and self-talk
• [36:31] – Timeless advice for founders: continuous reinvention

Tone & Language

The conversation is fast-paced, witty, and frank, with a blend of technical, cultural, and psychological insights. Steven is candid about his failures and growth, openly discusses mental health and mindfulness, and brings a philosophical depth to the standard fare of fintech entrepreneurship.

Conclusion

This episode provides a dynamic lens into the changing retail investing landscape, driven by Gen Z psychology, social media, and technology like Dubb. Steven Jiang’s journey—marked by boldness, self-reflection, and community-building—offers tactical lessons for both investors and entrepreneurs navigating this new era.