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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
This dynamic episode features venture capital veterans Jason Lemkin and Rory O'Driscoll dissecting the biggest stories shaping the tech landscape today. (00:45) They explore how AI-native companies are burning cash at unprecedented rates while achieving remarkable growth rates, the challenges facing traditional B2B companies in securing funding, and the staggering energy requirements of OpenAI's ambitious plans. The conversation delves into the reality that venture capital has become increasingly binary - with massive investments flowing to AI leaders while solid but non-AI companies struggle to raise capital despite strong fundamentals.
Jason Lemkin is a prominent venture capitalist and founder of SaaStr, one of the largest communities for B2B software professionals. He's known for his deep expertise in SaaS metrics and has been investing in enterprise software companies for over a decade. Lemkin is recognized for coining influential metrics like the "magic number" for sales and marketing efficiency and is a frequent speaker on SaaS growth strategies.
Rory O'Driscoll is a seasoned venture partner with extensive experience in B2B software investments. He brings a analytical perspective to venture capital, having worked with numerous enterprise software companies throughout their growth stages. O'Driscoll is known for his thoughtful approach to valuation metrics and his ability to identify sustainable business models in the rapidly evolving software landscape.
AI-native companies under $100M ARR have terrible free cash flow margins at -126%, much worse than non-AI companies at -56%. (04:03) However, because these AI companies are growing at unprecedented rates, their burn multiple (dollars spent per dollar of ARR added) is actually much better than traditional SaaS companies. This creates a paradox where seemingly inefficient companies are actually the most capital-efficient investments for VCs. The key insight is that when companies are growing fast enough, even high burn rates can translate to exceptional capital efficiency when measured against revenue creation. For ambitious professionals, this demonstrates the importance of velocity over absolute efficiency - sometimes spending more to move faster creates better long-term outcomes than conservative approaches.
VCs are increasingly unwilling to fund companies that aren't breakout AI leaders, even those with strong traditional metrics. (14:13) Companies growing at triple-triple-double-double rates with good burn multiples are struggling to raise capital if they're not AI-native or market leaders. This represents a fundamental shift where a $15M revenue company with reasonable growth has "zero value to a VC" because investors are focused on the "upside option game." The advice for founders in this environment is stark: if you can get funding, take it immediately rather than optimizing for price. This teaches professionals that market timing and positioning matter more than perfect fundamentals - sometimes good enough numbers in the right market beats perfect numbers in an unfashionable space.
Classic SaaS metrics like burn multiple, while still useful, are becoming less reliable in the AI era due to hidden assumptions about churn, gross margins, and revenue quality. (08:08) Rory O'Driscoll explains that burn multiple worked well when all companies were similar - 80-90% gross margin, enterprise sales, low churn SaaS businesses. Now with AI companies having different cost structures, trial-based models, and varying gross margins, these metrics can be misleading. The lesson for professionals is to understand the assumptions underlying any framework they use. When market conditions change rapidly, you need to dig deeper than surface-level metrics and understand the fundamental drivers of business value.
The advantage of being the market leader in AI categories is creating unprecedented barriers for competitors, with VCs reluctant to fund anything that competes against a "kingmaker" company. (20:48) This is partly because nervous buyers in the AI space want to make safe purchasing decisions and will default to the recognized leader. Additionally, successful AI companies are attracting follow-on investment that creates "walls of money" - where a $20M initial round leads to $80M in follow-up funding, making competition nearly impossible. The strategic implication is that in rapidly evolving markets, establishing market leadership early is more valuable than perfect execution later. Speed to market leadership can be more important than technical superiority.
The stability that characterized B2B software from 2008-2023 has ended, with AI forcing unprecedented rates of product change and creating new risks for both investors and operators. (62:31) Jason Lemkin notes that products didn't change for a decade in traditional SaaS, with some companies taking four years just to launch a mobile app. Now, companies must continuously innovate or become obsolete within months. This creates challenges for private equity firms who relied on buying stable assets, and even for venture investors as companies can lock into and out of product-market fit as AI models evolve. For professionals, this means continuous learning and adaptation are no longer nice-to-have skills but essential for survival.