Brendan Mathews is the Managing Partner of Motley Fool Ventures. Brendan joined the show to discuss how public-market thinking translates to early-stage venture, why raising too much capital can leave startups trapped, and how investors should navigate an increasingly consensus-driven market. They also explore technology hype cycles through the lens of autonomous vehicles and AI, the dangers of averaging down, why missing a huge winner can hurt more than taking losses, and Brendan’s contrarian view that most venture funds should charge lower management fees.

Here's a long rundown of the episode:

How to invest in a market dominated by consensus deals. Brendan explains why investors need to understand their own position in the venture ecosystem rather than blindly compete for the hottest rounds. Smaller funds may be better served by focusing on capital-efficient companies, reasonable valuations, and opportunities that can survive without constant access to large follow-on rounds.

Why raising too much money can hurt founders. Brendan walks through how oversized rounds and liquidation preferences can trap otherwise healthy companies. A startup may grow substantially and still struggle to produce an attractive outcome for founders if it raised more capital than its eventual exit value can support.

The venture capital treadmill. Founders who build high burn rates can put themselves in a position where they have no choice but to keep fundraising. Brendan argues for preserving optionality: raise enough capital to make progress, but avoid creating a company that dies if the next financing doesn’t arrive on schedule.

What Progressive taught Joe and Brendan about technology hype cycles. Looking back at work they did together more than a decade ago, they revisit fears that autonomous vehicles would quickly disrupt auto insurance. Brendan connects the experience to the idea that investors often overestimate a technology’s short-term impact while underestimating its long-term consequences.

Why obvious trends can still produce extraordinary returns. Amazon, Apple, Visa, digital advertising, mobile, and e-commerce were hardly secret trends by the time many investors bought into them. Brendan argues that investors don’t necessarily need to identify a technological shift first; enormous value can still be created by recognizing a durable trend and staying with it for a long time.

A gardener’s approach to portfolio construction. Brendan has moved away from trying to engineer a portfolio precisely by sector, stage, and conviction. Instead, he prefers to spread initial bets, diversify across time, and let the winners organically become larger parts of the portfolio.

Why missing the biggest winner can be worse than taking losses. Venture and public markets are both driven by power laws. Brendan points to missing Nvidia as an example of how failing to own one enormous winner can matter more than several investments going to zero, which has pushed Motley Fool Ventures toward a broader portfolio.

Why venture fees may be too high. Brendan closes with his contrarian view that management fees have failed to adjust for larger fund sizes and lower operating costs. He argues that many firms should run leaner, put more capital into portfolio companies, and rely more heavily on carry—while a small number of highly sought-after managers might actually be better off charging higher fees rather than continually raising larger funds.

Investing in Startups is hosted by Joe Magyer.

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.

Gopinath Sundaramurthy is a Partner at Ensemble VC, where the firm uses data and software to systematically identify promising founders and investment opportunities at the earliest stages.

In this conversation, we talked about how AI is changing venture capital, why data may become one of the few durable advantages between firms, and what happens when investors apply the same operating discipline they expect from startups to themselves.

Gopi explains how Ensemble uses data to improve sourcing and diligence without trying to replace human judgment. The goal is to automate the work of finding and understanding companies so investors can spend more time building relationships, evaluating founders, and developing conviction.

We also discuss how Ensemble evaluates founding teams, why Gopi believes most startup ideas are evolutionary rather than revolutionary, and why following where exceptional talent is moving can be more useful than starting with a fixed investment thesis.

Gopi also shares his views on portfolio support, follow-on investing, and why many VC firms have been surprisingly slow to adopt the technologies and processes they encourage their founders to embrace.

Investing in Startups is produced by Seaplane Ventures and hosted by Joe Magyer.