Negotiating with Existing Investors

Why do some venture-backed companies struggle to survive despite strong technology and teams? In this episode, David Weisburd speaks with Trey Ward about the structural differences between software and hard-tech businesses, the predictable “Death Valley” many startups face, and what recent data suggests about the future of venture funding. Trey shares how capital intensity is often misunderstood, why graduation rates are declining, and how profitability can create a path forward when fundraising stalls.

Highlights:

• Why strong conviction matters most when the market disagrees
• How hardware and software revenue curves fundamentally differ
• The misconception around capital intensity in deep-tech businesses
• What “Death Valley” looks like for hard-tech startups
• How investors distinguish failed companies from those with unmet potential
• Data showing declining Series A–to–Series B graduation rates
• Why a post-2022 venture funding hangover is accelerating failures
• Acquiring venture-backed assets at a fraction of historical R&D spend
• Using profitability as a strategy to give founders more time

Guest Bio:

Trey Ward is the Founder of Rook, an investment firm focused on acquiring venture-backed technology companies that have strong fundamentals but lack access to continued venture funding. He has spent his career investing in and operating across hardware, software, and deep-tech businesses, with a focus on capital discipline, long-term value creation, and paths to profitability outside the traditional venture model.

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.

Stay Connected with David Weisburd:

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

Stay Connected with Trey Ward:

LinkedIn:linkedin.com/in/thomasvwardiii

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 (4:04) Challenges and differentiators for hard tech startups (7:46) Venture capital downturn and strategies for struggling assets (14:07) Investment structures and management retention in acquisitions (16:17) Closing remarks