Why the Best Deals Aren’t Competitive with Alex Rubalcava of Amplify

Alex Rubalcava, Managing Partner at Amplify, 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.

Here's a longer breakdown of the conversation:

Why technology risk may be overrated. Alex explains why technically ambitious startups have historically scared off many early-stage investors—and why being willing to underwrite that risk can create an edge. Today, as AI makes software easier to build, he sees more meaningful technical risk shifting toward hardware, physical products, regulated markets, and other areas where reliability matters.

How AI is changing what investors should look for. Shipping features is becoming easier, so simply asking whether a team can build is less informative than it once was. Alex argues that investors increasingly need to understand whether founders know what to build, in what order, and how quickly they can adapt as technology and competition change.

What public-market investing taught Alex about venture. His background as a contrarian, value-oriented investor made him unusually sensitive to valuation and trained him to ask: Why am I seeing this opportunity? That mindset helps him avoid groupthink and focus on situations where he has a differentiated reason to develop conviction.

Why Alex prefers greenfield markets. Some of his favorite companies enter markets where there is no incumbent software vendor, Gartner category, or existing technology budget. Rather than competing against dozens of venture-backed startups, he prefers opportunities where a startup can create an entirely new market—or where incumbents are structurally unable to respond.

How capital efficiency protects non-consensus companies. Being early and different only works if a startup has enough time to prove the thesis. Alex explains why he works backward from the milestones future investors will need to see and why AI-enabled efficiency can give companies more runway to remove product, technical, and market risk before raising again.

Why a circle of competence should never be static. Alex traces his progression from enterprise software into robotics, space infrastructure, physical AI, and eventually space lasers. The goal isn’t to suddenly jump into unfamiliar sectors, but to expand expertise through adjacent investments until new categories become underwritable.

Productive persistence versus grinding in place. Alex shares the story of a founder who worked relentlessly but never found meaningful customer adoption. The distinction, he says, is often the velocity of experimentation: productive founders continually test new products and go-to-market approaches, while unproductive persistence means repeating the same motion despite continued evidence that it isn’t working.

Why conviction may matter more than allocation. Alex closes with one of his strongest contrarian views: companies that attract only one term sheet can sometimes be better investments than heavily contested rounds. Many of his strongest investments faced little competition, reinforcing his belief that investors should spend less time chasing hot deals and more time building independent conviction.

Investing in Startups is hosted by Joe Magyer.