Investing in Startups

Joe Magyer

Investing In Startups explores the strategies and stories of leading early-stage venture capitalists. The show is for VCs, LPs, angels, founders, operators, and the startup-curious. Whether you're a seasoned pro or just dipping your toes into startups, this podcast is your guide to navigating this dynamic ecosystem. The show is hosted by Joe Magyer, Founder and Managing Partner of Seaplane Ventures.

  1. Oct 28

    Hype Cycles, Consensus Investing, and the Venture Treadmill with Brendan Mathews of Motley Fool Ventures

    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.

  2. Oct 14

    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.

  3. Sep 3

    Data, AI, and Why Venture Firms Need to Act Like Startups with Gopi Sundaramurthy

    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.

  4. Jul 22

    Power Laws, Venture Math, and Changing Your Mind with Abe Othman

    Abe Othman has spent years digging into AngelList’s data to better understand how venture investing actually works, not just how investors say it works. In this episode, Abe joins host Joe Magyer to talk about portfolio construction, check sizes, valuations, and the relationship between price and returns. They discuss how much investors should put into each deal, why owning more of a company isn’t always better, and what the data can (and can’t) tell us about building a strong early-stage portfolio. They also get into contrarian thinking and the importance of changing your mind when the evidence changes. Abe shares some of the beliefs he has reconsidered over the past few years and explains why good investing often means letting go of ideas that once seemed obviously true. It’s a thoughtful, numbers-heavy conversation about making better decisions in an asset class where the outcomes are extreme, the sample sizes are small, and certainty is usually an illusion. Investing in Startups is hosted by Joe Magyer. The show is a Seaplane Ventures production.

  5. Jun 26

    From SaaS to Systems of Work: The Vertical AI Opportunity with Nick Tippmann

    Nick Tippmann is the Founder of TipTop Ventures where he invests in vertical AI and applied AI companies at the earliest stages. In this conversation, we talked about vertical AI, systems of work, and why distribution may matter more than ever in a world where software is getting easier to build. Nick explains why vertical AI is not simply the next version of SaaS. In his view, the unit of value is shifting from time saved to work delivered. That changes the buyer, the budget, the pricing model, and the size of the opportunity. Where traditional vertical software captured a slice of software spend, vertical AI can go after much larger labor and services budgets by doing the work itself. We also discuss what makes vertical AI companies defensible. Nick shares why the best companies are not just thin wrappers on top of foundation models, but systems of work that combine workflow, context, proprietary data, and domain-specific judgment. He explains why OpenAI and Anthropic moving up the stack may actually prove that intelligence alone is not enough. A big theme in the episode is go-to-market. Nick argues that many fundamentals have not changed: trust, domain expertise, tight ICPs, fast time to value, and distribution still matter. But in an AI-native world, pricing is being rewritten, revops and go-to-market engineering are becoming table stakes, and founders need to think earlier about brand, community, and how they stand out in crowded markets. We also talk about Nick’s journey from operator to investor, what he learned as CMO of Greenlight Guru, what he saw early in GC AI, and what VCs and founders often misunderstand about each other. It is a conversation about the future of software, the realities of early-stage investing, and how to separate durable vertical AI businesses from the noise. Investing in Startups is produced by Seaplane Ventures and hosted by Joe Magyer.

  6. Jun 8

    The Rapid Rise of AI with Niki Scevak [Encore Episode]

    This episode originally aired in September 2024 — and it's aged remarkably well. We're bringing it back with fresh context on why Niki's predictions have proven out.   Niki Scevak is co-founder and partner at Blackbird, Australia and New Zealand's most prominent venture capital firm. What started with a $29M AUD debut fund and 500 meetings to get 96 people to say yes has grown into a platform with six flagship funds, six portfolio unicorns, and a seed investment in Canva that became one of the greatest venture bets ever made.   In this conversation, Niki talks about writing a $250K check into Canva's seed round and investing $270M+ across the company's life. Since we recorded this, Canva has hit $4B in annual revenue and is reported to IPO on the Nasdaq in 2026.   We also dig into Niki's views on AI application software — the extraordinary growth rates, the premium pricing power, and the churn problem lurking underneath. Eighteen months later, the data has validated nearly everything he said here.   In this episode, we cover:   — How Blackbird went from a $20M USD fund to backing multiple unicorns — Why the best companies tend to be successes from the start — The case for investing before product, before revenue, before anything — Blackbird's approach to giving founders honest, specific feedback — Why AI application companies grow faster than anything Niki has ever seen — and why churn is the catch — How Australia's superannuation system became a venture capital superpower — Seed valuations post-COVID and what determines the "right" price — The biggest misconception about the Australian startup ecosystem   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

  7. May 20

    Hot Seed Deals, Quitting, and Liquidity with Peter Walker of Carta

    Peter Walker is Head of Insights at Carta, where he tracks some of the most important data shaping venture right now. In this conversation, we talked about hot seed deals, quitting, liquidity, and what the latest market data really says about valuations, exits, and the changing structure of venture.   Peter explains why the most expensive seed deals may be more rational than they look, especially if your goal is to back the tiny handful of companies that could become massive outcomes. But he also makes clear that the real challenge is not just getting into great companies. It is figuring out how those companies actually generate liquidity in a world where IPOs are rarer, secondaries are concentrated in a few names, and many private companies are staying private longer than investors once expected.   We also discuss how the venture market is splitting in two. At the very top, consensus companies in the “golden circle” are attracting extraordinary prices and attention. Outside that inner ring, founders are still facing a much tougher environment, where expectations are high and capital is harder to win. Peter shares why common fundraising heuristics like a single ARR benchmark for raising a Series A are often misleading, why growth and momentum matter more than any fixed revenue number, and how AI is making revenue quality harder to judge than it used to be.   A big theme in the episode is what venture gets wrong. Peter talks about why some founders probably should quit sooner, why solo founders may deserve more credit than they often get, and why concentration is not the only way to build a great fund. It is a conversation about market structure, incentives, and how investors and founders can think more clearly in a venture environment that is getting more extreme at both ends.   Investing in Startups is produced by Seaplane Ventures and hosted by Joe Magyer.

  8. Apr 29

    B2B in the Age of AI and Services as Software with Ariel Winton-Jones

    Ariel Winton-Jones is the founder of The Aligned Fund, where she invests in B2B software companies at the earliest signs of product-market fit. We talked about services as software, what B2B looks like in the age of AI, and why intentional investing can be a real edge. Ariel explains how her thinking evolved from traditional B2B SaaS into what she calls “services as software.” In a world where AI is changing what software can do, she’s most excited by businesses that don’t just give users tools, but actually deliver outcomes that once required human labor. Instead of software as a DIY layer, she argues that the next wave of great B2B companies will solve the problem itself. We also talk about Ariel’s investing style and why she operates with unusual intention in a market that often rewards speed. She shares why she likes to meet founders early, spend real time understanding how they think, and build conviction through deep diligence rather than just pattern matching from a deck. A big part of the conversation is her focus on early product-market fit and why she believes that stage is more knowable than many investors assume. Ariel also breaks down why she remains so committed to B2B software. We discuss why B2B has proven resilient, how AI is expanding the kinds of markets that can support venture-scale outcomes, and why there is no single right way to price or sell software. What matters most, she argues, is fit between the product, the customer, and the value being delivered. Finally, we discuss concentration, reserves, and what venture often gets wrong. Ariel explains why she prefers a low-velocity, high-conviction approach, why she keeps reserves low, and why the best early-stage investing often comes from going much deeper on fewer opportunities. It’s a conversation about software, judgment, and how to invest thoughtfully when both technology and venture are changing fast. Investing in Startups is produced by Seaplane Ventures and hosted by Joe Magyer.

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5
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23 Ratings

About

Investing In Startups explores the strategies and stories of leading early-stage venture capitalists. The show is for VCs, LPs, angels, founders, operators, and the startup-curious. Whether you're a seasoned pro or just dipping your toes into startups, this podcast is your guide to navigating this dynamic ecosystem. The show is hosted by Joe Magyer, Founder and Managing Partner of Seaplane Ventures.

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