Why the Best Deals Aren’t Competitive with Alex Rubalcava of Amplify
Alex Rubalcava is a Managing Partner at Amplify. Alex joins Joe Magyer to discuss contrarian early-stage investing, how AI is reshaping software risk, and why some of the best venture opportunities attract little competition. They also cover greenfield markets, capital efficiency, lessons from public-market investing, expanding a circle of competence, and how to tell productive persistence from simply grinding on something that isn’t working.
The episode is now available on Apple Podcasts, Spotify, Amazon, and YouTube Music.
Why the Best Deals Aren’t Competitive with Alex Rubalcava of Amplify
00:49 – Why technology risk is overrated
03:31 – AI and the future of software defensibility
07:01 – Contrarian investing and lessons from public markets
16:44 – Fundraising risk and capital efficiency
20:53 – Why Alex prefers greenfield markets
24:41 – Secondary sales and returning capital to LPs
30:35 – How to break into venture capital
36:02 – Expanding your circle of competence
40:47 – When founders should stop grinding
47:47 – Why conviction beats competing for allocation
Why the Best Deals Aren’t Competitive with Alex Rubalcava of Amplify
Technology risk can create opportunity for early-stage investors. Alex explains why many VCs avoid startups tackling difficult technical challenges and how investors willing to underwrite those risks can find compelling opportunities. As AI reduces traditional software development risk, he sees opportunities shifting toward frontier technologies and physical-world applications.
AI is fundamentally changing what makes software defensible. Building software is easier than ever, forcing investors to reconsider traditional competitive moats. Alex is particularly interested in software operating in regulated, financially sensitive, or otherwise high-stakes environments where reliability, accountability, and human oversight remain essential.
The ability to sell and make smart product decisions matters more than ever. Alex revisits his framework for evaluating founders: Can they ship, sell, and hire? With AI accelerating product development, sales velocity and knowing what to build—and when—have become increasingly important differentiators.
Venture capital has a groupthink problem. Drawing on his background as a contrarian public equities investor, Alex discusses how consensus thinking influences venture investing. He argues that valuation discipline, independent judgment, and a willingness to pursue overlooked opportunities can provide an enduring investing edge.
Great venture returns don't require billion-dollar funds or trillion-dollar companies. Alex challenges the idea that the best investment opportunities are concentrated among the largest venture firms. He explains how smaller funds can generate outstanding LP returns through exits that barely register in the broader technology industry.
Capital efficiency is one of the best defenses against fundraising risk. Alex explains how higher interest rates, longer liquidity timelines, and increasingly consensus-driven follow-on investors shape his approach. He shares examples of fast-growing, profitable software companies struggling to attract investor interest simply because they lack a compelling AI narrative.
Greenfield markets offer some of the most attractive investment opportunities. Rather than compete in crowded categories, Alex prefers companies creating entirely new markets or serving customers without existing technology solutions. He explains why shipping real products, generating revenue, and demonstrating customer demand are critical to de-risking these investments.
Successful venture investing requires evolving your approach to liquidity, diligence, and expertise. Alex discusses the role of secondary sales in generating DPI for LPs, how Amplify leverages its network of portfolio founders during diligence, and why an investor's circle of competence should continuously expand without losing its focus.
Persistence is valuable only when founders are learning and adapting. Alex distinguishes founders who continually experiment with products and customer acquisition from those repeating unsuccessful strategies. He shares the story of a founder who worked tirelessly but ultimately shut down his company and returned half of the invested capital rather than continue pursuing a market that wasn't responding.
The best investments aren't necessarily the most competitive deals. Alex closes with a contrarian perspective: Startups attracting only one term sheet can be better opportunities than heavily contested rounds. At Stage VP, 42 of his 45 investments were not competitive, reinforcing his belief that developing independent conviction can be far more valuable than fighting for allocation.
The content here is for informational purposes only and should not be construed as investment, legal or tax advice. The opinions expressed by guests are their own and do not reflect the views of Seaplane Ventures. Our host, guests and clients may hold investments discussed in this podcast. Please invest responsibly.
