When to take wins versus holding forever

What if your family office could invest like a founder and a VC at the same time? In this episode, I sit down with Shane Neman, founder of a multi-entity family office with $850M AUM, to explore how he approaches venture investing, deep tech, and portfolio construction. Shane shares how his two decades as a SaaS founder shape his edge as an investor, why transparency and founder relationships matter more than fund mandates, and how he balances high-conviction bets with a rational family office lens. He also dives into frontier tech, co-invest structures, and building a diversified yet opportunistic portfolio.

Highlights:

• Why being a founder gives him insight most VCs lack
• How investing personal capital changes risk appetite and alignment
• The case for radical transparency in co-investing and syndicates
• Why he focuses on emerging managers for outsized exposure and insight
• How he structures “barbell” portfolios across deep tech and durable businesses
• Lessons from early crypto, AI, and frontier tech investing
• How portfolio construction balances spiky alpha with long-term growth
• Why founder relationships often trump pro rata rights in venture deals

Guest Bio:

Shane Neman is the founder of a multi-entity family office investing across venture, crypto, frontier tech, and real assets. Formerly a SaaS founder, Shane leverages his operational experience and technical background to identify exceptional companies, co-invest with emerging managers, and structure high-conviction, founder-aligned investments. His portfolio combines early-stage moonshots with resilient businesses, reflecting a thoughtful approach to alpha generation and family office growth.

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 AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

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Stay Connected with Shane Neman:

LinkedIn: https://www.linkedin.com/in/shaneneman/

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 (1:50) Radical transparency and differences between family offices and VC co-investing (3:25) Institutional investors, direct deals, and liquidity trends (5:11) Scaling single deals to nine figures (9:32) Portfolio construction: Balancing deep tech and stable investments (14:27) Example of late-stage investments: Paradromics (15:24) Growth vs. capital preservation in family offices (19:14) Diversification and portfolio optimization strategies (21:23) Psychological challenges in venture capital (22:01) Early investments and recognizing potential in crypto (27:05) Scaling to 850 million AUM and associated challenges (28:24) Evolution of investment strategy: Seed vs. later-stage (31:13) Importance of founder relationships and pro rata rights (32:11) Advice to younger self on capturing potential outcomes (34:13) Selling investments: Balancing holding and liquidating (36:14) Illiquidity as a virtue and its decision-making impact (37:17) Tax considerations and investment management strategies (39:33) Emotional challenges of holding or selling large gains (40:20) Thoughts on transformative investments: SpaceX and Figure (42:07) Closing remarks