Investing in Startups

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

Wed, 29 Apr 2026 09:00:00 +0000

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.

Future Titans, Authenticity, and Systems Thinking with Daniel Dart

Wed, 15 Apr 2026 11:00:00 +0000

Daniel Dart is the Founder and General Partner of Rock Yard Ventures. He is also the founder of the Future Titans summit, an amazing event he recently hosted in Austin for emerging managers and the LPs who back them. Daniel is a collaborative, Seed-focused investor focused on backing founders who are refunding core industries. We talked about Future Titans, ambition, authenticity, and the pursuit of Tier One status. We also explored:

Why Future Titans exists: Daniel built the Emerging Manager Summit as the room he wished existed—relationship-first, practical, and designed for funds I–III (not a conference-business play). He’s focused on creating the right environment vs. chasing early vanity metrics.

Anti-status design (no name tags / no pitch decks): He argues most events incentivize social stack-ranking and transactional behavior; removing those cues forces human-first conversations and lowers the “pitch” energy.

Core philosophy: “find believers, don’t convince skeptics.” Trust is his upstream variable for everything—LP relationships, founder support, community building. His “patron/believer” framing is about compounding a small set of true supporters over time.

Founder support system (real operator cadence): He shares a concrete post-check rhythm—every-other-week check-ins early, then monthly—aimed at building trust and creating a safe place for founders to think clearly when things get messy.

Building “tier-one” access via a “Voltron” network: Rather than pretending he can see everything, he wants a trusted brain-trust where high-signal peers effectively extend his coverage; Future Titans is partly a compounding mechanism for that.

Investing in Startups is hosted by Joe Magyer, founder and managing partner of Seaplane Ventures.

Momentum, Moats, and the New Rules of Pre-Seed with Gaurav Jain

Wed, 01 Apr 2026 11:00:00 +0000

Gaurav Jain is the Cofounder and Managing Partner of Afore Capital. Afore is one of the OGs of institutional pre-seed investing and runs the largest dedicated pre-seed venture fund in the world. We talked about momentum as a moat, how vibe-coding effects pre-seed investing, and the importance of great product and distribution. Here's a longer breakdown…

Gaurav explains why momentum has become more durable than traditional moats, especially in a world where AI is making it easier to build products quickly. Instead of relying on old ideas of defensibility, he argues that the best startups create constant forward motion through product improvement, user pull, and rapid execution.

We talk about what Afore Capital looks for at the pre-seed stage, when there may be very little company built and not much data to evaluate. Gaurav shares how he thinks about backing founders early, what signals matter most before traction exists, and why team quality often matters more than a polished market narrative.

Gaurav also breaks down how AI is changing startup formation, from reducing the amount of capital needed to build a company to speeding up the path from idea to product and customer feedback. The conversation explores what this means for founders, investors, and the pace of competition in the earliest stages.

A big theme in the episode is distribution and founder-led selling. Gaurav talks about why distribution can’t be treated as an afterthought, why technical founders still need to learn how to get in front of customers, and how the best early companies pair strong product instincts with a clear path to demand.

Finally, we discuss how pre-seed investing has evolved over the last decade and what Gaurav has learned from helping define the category. He shares lessons on market size, founder selection, and why early-stage investing is often less about predicting categories and more about recognizing the people most capable of creating momentum from nothing.

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

AI, Hot Deals, & Ownership: Joe Magyer Reflects on 50 Episodes

Wed, 18 Mar 2026 10:00:00 +0000

We're celebrating our recent 50th episode with a special conversation between host Joe Magyer and guest host Chris Hill of Money Unplugged. Chris interviews Joe about his lessons learned from the first 50 episodes, how AI is impacting startups and venture capital, what Joe has changed his mind about, and investing in startups, both the craft and the show. Joe and Chris also unpack how AI has reshaped venture in just two years—changing what it costs to start a company, how many people startups need to hire, how quickly they can build product, and why investors are again leaning into the category after a brutal post-2021 reset.

They revisit one of venture’s oldest debates: concentrated vs. diversified portfolios. Joe explains why some investors want as many shots on goal as possible, while others prefer to place fewer, higher-conviction bets so they can spend more time with founders and have a better chance of meaningful ownership in the winners. Another core tension in the episode is consensus vs. non-consensus investing. Joe talks through why the hottest deals often get hot for good reasons—great founders, fast growth, strong co-investors—but also why crowded rounds can compress returns and leave investors paying up for certainty that may already be priced in.

Finally, Joe also shares how hosting the podcast has changed his own investing style. Hearing other managers explain their frameworks pushed him to rethink rigid reserve strategies, become more flexible about follow-on investing, and focus more on doubling down when real conviction builds through direct founder relationships.

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

Live Episode! A Future Titans Collab and Solo GP Life with Zal Bilimoria

Wed, 04 Mar 2026 11:00:00 +0000

We're excited to share this interview with Zal Bilimoria, founding partner at Refactor Capital, recorded live at the recent Future Titans emerging manager summit. Zal is a high-conviction, hard-tech investor and solo capitalist who manages more than $225 million. He has a fascinating career, from building products at Netflix and LinkedIn to being an early employee at a16z to later forming Refactor. We talked about why Zal is solo, what he learned from a16z, why he invests with conviction, how he built a robust firm without any employees supporting him, and how he managed to lead a Series D round despite his firm being a Seed expert. We also discussed:

Why Zal chose the solo GP path (on purpose): after seeing large-firm partnership dynamics at Andreessen Horowitz, he optimized for speed, autonomy, and founder time—especially important at seed where decision velocity matters. Refactor started as a two-GP fund with David Lee (ex–SV Angel), then David retired earlier than expected—forcing Zal to rebuild the LP base and prove the strategy could work with a single decision-maker.

A “right-sized” fund strategy as an operating system: Zal explains why he’s stayed around ~$50M per fund, targets ~20 companies per fund, and focuses on ~8–10% ownership at entry to keep the model manageable and return-capable. He actively tracks how many portfolio companies “graduate” (to Series A and beyond) each year so his board/support load stays sustainable without adding headcount.

Robustness for LPs (the “hit-by-a-bus” plan): Zal shares a concrete solo-GP risk mitigation tactic—he carries a life insurance policy payable to the management company so LPs have resources to recruit a successor or wind down assets without crushing fund performance.

Hard tech example that feels sci-fi (with real traction): Solugen. Zal recounts leading Solugen’s seed ~9 years ago and watching it scale into a large revenue business—then pivoting into a high-demand defense chemistry product with major government pull.

How a seed lead ends up leading a Series D: during the 2022 market reset, Zal had an SPV ready (~$20M) to secure pro rata; when no one wanted to “stick their neck out” as lead, he wrote the first term sheet—unlocking the round and attracting co-leads/followers.

Reserve strategy shift: he describes moving from ~50% reserves to ~20% reserves—preferring more “shots on goal” at pre-seed/seed, and noting how hard it is to consistently pick Series A winners even when top firms lead the round.

Investing in Startups is hosted by Joe Magyer, founder and managing partner of Seaplane Ventures.

Episode 50! Venture Strategy, Real Work, & The Myth of Overnight Success with Seth Levine

Wed, 18 Feb 2026 11:00:00 +0000

Seth Levine is a Partner at Foundry Group, a longtime early-stage firm investing in both startups and emerging fund managers. We talked about the art of working with founders, short-term-ism, knowing your own competitive advantage, why AI will create more jobs than it disrupts, and the myth of overnight success. Here's the longer of what we covered:

Doing the real work with founders and GPs – Seth explains why his favorite part of Foundry is deep, collaborative problem-solving with CEOs and emerging managers, not formal board meetings, and why he sees himself as “in the influence game,” working for founders rather than controlling them.

Fund size is fund strategy – He walks through why Foundry chose not to become a perpetual, multi-generational platform, and how everything from check size to reserves, board work, and follow-on strategy has to flow from the true size and intent of the fund—not from chasing a bigger AUM number.

What LPs miss about emerging managers – Drawing on Foundry’s long history backing funds, Seth argues most LPs behave like asset allocators who over-weight pedigree, underwrite theses too superficially, and don’t dig hard enough into a GP’s real edge, philosophy, and personal “why” for running a firm.

Under-explored fund models he loves – Seth highlights niche yet powerful strategies: Arthur Ventures’ “under-the-radar” B2B SaaS approach, roll-ups of orphaned 2019–2020 vintage funds, and hybrid revenue-based vehicles that blend debt-style payback with equity upside for founders.

If he were starting fresh today – From a pure performance standpoint, he’d run a much more diversified early-stage book with lots of initial positions and minimal follow-ons—Taleb-inspired barbell thinking—and, in a wilder alternate life, maybe build a Series A or growth platform in Saudi Arabia to ride frontier-market upside.

Capital Evolution & fixing capitalism, not ditching it – Seth shares the origin story of his new book, his evolving view on when companies should (and shouldn’t) wade into politics, the shift from shareholder primacy toward broader stakeholders, and why medium- to long-term thinking and greater economic dynamism are essential.

AI, entrepreneurship, and why venture’s glamor is BS – He’s long-term bullish and short-term cautious on AI, seeing it as a huge unlock for productivity and entrepreneurship far beyond tech—but also a source of disruption that needs thoughtful retraining and policy.

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

E49: AI Agents, Unlocking Human Potential, and Not Giving Up with Hyperspell

Fri, 06 Feb 2026 13:00:00 +0000

Conor Brennan-Burke and Manu Ebert are the co-founders of Hyperspell. Hyperspell provides a memory and context layer to AI agents is one of our portfolio companies at Seaplane Ventures. I (Joe here) was trying to explain to some friends at a BBQ recently Hyperspell what did and learned pretty quickly that most people aren’t familiar yet with AI agents. Given that and the sudden explosion in interest in AI agents, I thought it would be great for listeners to have Conor and Manu to come on to talk about AI agents, the evolution of AI, context, Y Combinator, and how Manu once bought a .AI domain name via fax machine.

From chatbots to true agents – Conor breaks down where tools like ChatGPT stop and AI agents begin, and why the key shift is agents taking actions autonomously across your tools, not just answering questions.

Why context is the real bottleneck – Manu and Conor share how building their own “chief of staff” agent led them to Hyperspell, a memory and context layer that plugs into tools like Slack, Gmail, and Notion so agents can actually understand your customers, org chart, and tech stack.

The three bottlenecks to agent adoption – Manu explains why verification, capability, and context each limit what agents can do today, and why decoupling these layers (rather than relying on a single big lab) gives companies more flexibility and avoids platform lock-in.

Why workers aren’t using AI (yet) – Conor reacts to studies showing most desk workers rarely touch AI, and argues that fear, bad framing (“AI will replace you”), and lack of personalized context are holding back adoption despite models already outperforming humans on many benchmarks.

AI as global leapfrog, not just US office automation – Manu highlights under-discussed upside: primary care in Africa, McKinsey-grade advice for small businesses, tailored guidance for farmers, and always-on tutors that could reshape opportunity in developing markets.

Let machines be the cogs, not people – The pair paint a future where AI agents handle status updates, follow-ups, and information shuffling inside big orgs, freeing humans to do creative, high-leverage work instead of feeling like dehumanized “TPS report” machines.

Building SuperMe and all-star AI teams – Conor shares a favorite customer use case: cloning experts (or even yourself) as agents using your own docs, email, and notes, so a solo founder can effectively “hire” an AI team of world-class operators and advisors.

YC, rejection, and founder stubbornness – Conor and Manu talk about finally getting into Y Combinator after nine applications between them, why persistence is a superpower for founders, and how YC has shaped Hyperspell’s trajectory.

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

E48: Backing Emerging Managers Before They're Brand Names with Courtney McCrea

Wed, 28 Jan 2026 12:00:00 +0000

Courtney McCrea is the Cofounder and Managing Partner of Recast Capital. Courtney and I dove into the intricacies of investing in emerging managers and building those firms. We talked about why Courtney is so enthusiastic about emerging managers, the challenges emerging managers face and how to overcome them, how LPs can better evaluate emerging managers, and why LPs aren’t racing to adopt AI as fast as their VCs.

We also discussed:

How LPs really evaluate first-time fund managers: beyond pedigree, what creates conviction in sourcing, selection, and portfolio construction.

Fund I fundraising strategy: why “spray-and-pray” outreach fails—and how to identify the right-fit LPs instead of chasing every allocator.

Where to start if you’re raising your first venture fund: go “off the beaten path” rather than leading with mega-institutions and public pensions.

LP diligence that actually matters: Courtney’s framework for reference calls, risk lists, and finding the “fatal flaw” early.

Solo GP vs partnership risk: why “GP divorce” can be a bigger underwriting risk than the classic “hit-by-a-bus” concern.

AI in the LP workflow: what Courtney is seeing (and experimenting with) in diligence and decision-making as venture processes modernize.

Joe Magyer is the host of Investing in Startups, which is a Seaplane Ventures production.

E47: Gritty Founders, Weird Markets, and Vertical AI with Dan Teran

Wed, 14 Jan 2026 11:00:00 +0000

Dan Teran is a Cofounder and Managing Partner of Gutter Capital. Gutter is an early-stage firm based out of New York focused on founders tackling the world’s toughest problems. We talked about why Gutter invests with conviction, why they seek out founders with unique insights rather than Gutter trying to dream up their own, and how AI can solve problems in the real world, not just online. We also dug into:

+ Gutter’s core focus on vertical AI, vertical SaaS, and marketplaces tackling messy, real-world problems

+ Why Dan gravitates toward underestimated, “lived-experience” founders over polished, pedigreed profiles

+ Inside Elbow Grease, Gutter’s AI accelerator: structure, check size, and how they plan to keep backing winners

+ How Gutter turns talent into a product: embedded head of talent and heavy support on early hiring

+ The firm’s discipline on valuations, small fund sizes, and staying aligned with founders in a top-heavy market

+ Why Gutter insists on taking a board seat at seed and how that sets companies up for stronger Series As

+ Dan’s lessons from selling Managed by Q to WeWork and why founders should build acquirer relationships early

+ Two contrarian views: second-time founders are overrated, and the best founders do want real help from their investors

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

E46: Breaking Rules and Letting Winners Run with David Gardner of The Motley Fool

Wed, 31 Dec 2025 12:00:00 +0000

Our guest this week is David Gardner, Cofounder of The Motley Fool. David is one of the best stock pickers of his generation. While for many investors a single 100X investment would be a career-defining win, David has earned a 100X return on 6 companies including Nvidia, Tesla, Amazon, and Netflix. We talked about breaking the rules of investing, optionality, valuation, letting winners run, and much more. David is one of the investors I’ve learned the most from over the years, so I really hope you enjoy this one.

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

E45: Access, Picking VCs, and Tough Love with Superclusters' David Zhou

Wed, 17 Dec 2025 12:00:00 +0000

David Zhou is an investor in emerging managers, an angel investor, a blogger, and the host of the Superclusters podcast. We talked about how LPs can size up emerging managers, how VCs can stand out, portfolio construction, and which of sourcing, picking, and winning is the most important. We also explored:

+ Why David thinks that “access beats picking (then winning)” for most emerging managers—and how check size changes that calculus.

+ Follow-ons: when “all or none” makes sense, how signaling risk compounds past Series B, and why selling by Series C can be clean for seed managers.

+ LP incentives in the wild: marks scrutiny for new managers vs. “ignorance is bliss” for existing ones—plus how TVPI vs. IRR targets shape decisions.

+ The tough-love playbook behind “Dear Emerging Manager” and “Dear LP,” and why sloppy valuation methods and survivorship bias mislead GPs.

+ Differentiation framework: sell the market → the strategy → then you; use “flaws, limitations, restrictions” to confront the elephants in the room.

+ Fund design realities: reserve strategy, fund size vs. dilution (esp. in hard tech), and why some LP minimums are a built-in constraint.

+ Context from fresh market data: median seed at ~$20M and AI capturing a huge share of early deals—what those trends mean for formation and pricing.

+ Plus: Abe Othman’s follow-on finding (funds that never follow on beat always-follow funds 63% of the time) as a jumping-off point for David’s take.

Investing in Startups is a Seaplane Ventures production hosted by Joe Magyer.

E44: Roundtable! Network Effects, Hustle, Raising Money, and More with Colin Gardiner and Sonia Nagar

Wed, 03 Dec 2025 12:00:00 +0000

We're trying something new with our first roundtable! Our guests are Sonia Nagar from SNAK Venture Partners and Colin Gardiner from Yonder Ventures. Sonia and Colin are both early-stage investors, friends of mine, and experts on marketplaces and network effects. We talked about AI’s role in marketplaces, why network effects aren’t more popular (even though they should be), how to make your own luck, what it’s really like to raise your first venture fund, and more. I hope you enjoy and thanks for listening.

Investing in Startups is produced by Seaplane Ventures.

E43: Trust, Paying Up, & Homebrew Forever with Hunter Walk

Wed, 19 Nov 2025 13:00:00 +0000

Our guest this week is Hunter Walk, Co-Founder of Homebrew and Screendoor. Hunter has a deep background in product, including from his time at Google and YouTube, but is best known for his investing. Homebrew’s big wins over the years include Chime, Plaid, Gusto, Cruise, and more. We talked about trust and context, product, funnel math, investing life after LPs, and why Hunter isn’t as fussy these days about valuation.

Here's a longer rundown of the episode:

Homebrew → “Forever.” Why Hunter and Satya moved from an LP-backed seed fund to a self-funded evergreen model—and why they accelerated the shift in 2022.

Ditching ownership targets. Early-stage “must-own X%” rules create artificial scarcity for founders; Homebrew now fits their check into whatever round construction serves the company best. Prioritizing alignment with founders and co-investors over leading every round.

Valuation: what it really signals. Price matters less as a target and more for what it reveals about the founder’s decision-making, who’s on the cap table, and the path to the next round—especially when you don’t hold reserves.

Trust + context > generic advice. Hunter’s operating model with founders: build trust to have honest conversations, and keep real context so advice is specific—not just a blog post link.

Meeting math & magnets. You can’t jump into every haystack—so create magnets (writing, references, approachability) to pull the right needles; historically ~1 investment per ~100 inbound companies.

Your company is a product. Hiring, comp, and cadence must cohere like a product system; inconsistency is the cultural anti-pattern.

Focus areas now. Still heavy B2B dev tools (increasingly AI/ML) and FinTech; comfortable as #2–10 on the cap table alongside specialists, which expands where they can help.

Against multi-gen for most firms. Hunter argues many venture franchises lose “fidelity” as AUM and headcount grow—like copies of a mixtape over time.

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

E42: From Public Markets to VC, AI, & Winning — Joe Magyer

Wed, 12 Nov 2025 14:00:00 +0000

Joe Magyer is the host of Investing in Startups, but his real job is running his early-stage boutique, Seaplane Ventures. In this episode, Joe is interviewed by his friend Owen Raszkiewicz, Founder and CIO of Rask Group and host of the Australian Investors Podcast. Joe talked why he made the move from public to private markets, how small firms can compete with big firms, the current venture landscape, putting AI to work as an investor, and why studying up on unit economics is a core part of early-stage investing. Please enjoy.

E41: Pre/Seed, Control Points, and Frenemies with Jackie DiMonte of Grid Capital

Wed, 29 Oct 2025 12:00:00 +0000

Jackie DiMonte is the Cofounder and General Partner of Grid Capital. We talked about power laws, investing with conviction, how to help founders in their earliest stages, small funds vs. big funds, and whether pre-seed valuations really are mental. We spoke in depth about:

- Why Pre/Seed (not just “pre-seed”). Jackie sees pre/seed as a continuum and optimizes for investing “before it’s obvious”—pre-PMF and before scale playbooks kick in.

- Concentrated by conviction. Grid leads rounds so every check matters; “party rounds” left no owner, unclear milestones, and shaky odds—so she backs fewer, deeper and sets explicit experiment plans.

- The pre-PMF playbook. Start with a market hypothesis, define the signals that prove or disprove it, and don’t hide from feedback—iterate fast on product, pricing, and business model.

- Control points > features. In crowded industrial/logistics AI, she looks for wedge use cases with fast time-to-value and durable leverage; otherwise it devolves into a customer-acquisition bloodbath.

- “Frenemies” in supply chains. Competitors often integrate and overlap; Grid underwrites only when the entry point creates credibility to crowd out others—important for a small, high-ownership fund.

- Founder archetype. Best fit: builders with industry roots and high-growth tech chops who show real customer empathy; solo vs. teams can both be superpowers.

- Marketplaces & vertical AI (reality check). Network effects are unmatched, but in industrials behavior change and trust make embedding hard; Jackie favors either core systems of record or AI-enabled services that deliver outcomes, not middling bolt-ons.

- Valuation dispersion & speed. The “power law” now shows up in fundraising: a few rounds price mental and close overnight on relationships, while most processes remain slow and illiquid.

- Geo lens. Grid’s industrial thesis maps to Chicago/Austin and the Atlanta-to-NY corridor; LA is emerging in manufacturing—where domain roots meet tech talent.

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

E40: The Art & Science of Portfolio Construction Plus Valuation Realism with Morgan Flager

Wed, 15 Oct 2025 12:00:00 +0000

Morgan Flager is the Managing Partner of Silverton Partners. Silverton is an early-stage firm that has had more than 30 companies IPO or get acquired. We talked about the art and science of portfolio construction, when to bend on price, and which of team, product, or market is most important. We also dove into:

Silverton’s “early PMF” lane. Sweet spot is writing ~$3–7M checks into companies with a handful of customers and early revenue; ~70–80% fit this stage, with occasional earlier/later outliers. About 60% of deals in Central Texas, ~10% elsewhere in TX, balance nationwide—leveraging two decades of local reputation while staying opportunistic.

Follow-on edge = objectivity. They’re data-driven on reserves, but the real unlock is knowing when not to keep doubling down; partners anonymously rank each other’s companies to curb politics and fumes.

Secondary rules of the road. If a breakout round implies 5–10x+ on a small sell (10–20%), they’ll often take it—bank DPI, let the rest ride; in 2021 they even mandated trims in that range. Fund-life alignment matters. As vehicles near years 10–12, selling a majority (or all) via secondary is often the right call.

Owner mindset inside the firm. Silverton lends to team members so they can co-invest—shifts psychology toward prudent partial sales vs. “let it ride” with other people’s money.

Team > market > product (at maturity). Early it’s founder-led, later it’s team-led; great teams self-correct on market/product, and Silverton will back a stellar team in a merely “B” market over the reverse.

Why origin stories matter. He listens for authentic passion and connection to the problem—grit to push through the “dark, lonely days” shows up in the journey, not the pitch deck.

Valuation realism > unicorn fantasies. Morgan calls BS on “pay any price” at seed; most outcomes aren’t $10B, and mispriced seeds can trap founders and misalign with later-stage mega-fund incentives.

Austin culture advantage. Smaller, reputation-sensitive network rewards doing right by founders; openness and pay-it-forward energy were a positive “culture shock” vs. the Valley.

Investing in Startups is a Seaplane Ventures production hosted by Joe Magyer.

E39: Networks, Flywheels, and Why Fintech is Thriving with Rex Salisbury

Wed, 01 Oct 2025 12:00:00 +0000

Rex Salisbury is the Founder and General Partner of fintech-focused Cambrian Ventures. We talked about how Rex built a big community and following in the fintech world, why fintech startups are on a roll, disruption versus partnership, and how the venture world is evolving.

E38: Lessons from Investing in 400 Startups with Charles Hudson of Precursor Ventures

Wed, 17 Sep 2025 12:00:00 +0000

Charles Hudson is the Managing Partner and Founder of Precursor Ventures. Precursor is a generalist pre-seed firm based in San Francisco that invests in startups from all over. We talked about the importance of founder-centric investing, portfolio construction, and the balancing act of taking money off the table with winners. Charles has made over 400 investments at Precursor and has a lot of insights to draw upon as a result.

We also covered:

How fewer than one-in-five firms make it to fund five.
Why building a firm with staying power is crucial.
How fundraising can be stressful for various reasons at various stages.
Liquidity in early-stage investments is becoming normalized.
LPs have varying expectations regarding returns and liquidity.
Why market size forecasting is challenging; focus on founders instead.
Early employees may not always be the best hires.
Entrepreneurial talent comes in various forms and backgrounds.
Venture capital is maturing as an asset class.
Founders can reach out directly to Charles for opportunities.

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

E37: Bigger Isn't Better and Give First with Techstars' David Cohen

Wed, 03 Sep 2025 12:00:00 +0000

David Cohen is the CEO and Cofounder of Techstars. Techstars is one of the OGs of startup accelerators, investing in almost 5,000 startups since Techstars was founded in 2006. David himself is a serial entrepreneur who was the founding CEO at Techstars, later stepped back from that role, and then returned as CEO in 2024. We talked about the problems that Techstars solves for founders, how vibe-coding affects accelerators, why Techstars finally opened up in SF, and why bigger isn’t better – better is better. Please enjoy.

A few longer highlights:

Techstars was founded to create a supportive community for entrepreneurs.
The accelerator model has evolved, with many new players in the market.
Quality of support is more important than the number of companies funded.
Techstars is focused on improving the offer for founders to attract high-quality startups.
The network of mentors and alumni is a key asset for Techstars.
Founders often come in with hubris but learn to embrace feedback.
The experience of founders in the program can lead to significant transformations.
Market selection is based on capital availability and community strength.
Techstars aims to maintain quality while allowing MDs autonomy in decision-making.
AI is changing the landscape of startup development, emphasizing storytelling and long-term vision.

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

E36: Network Effects, AI Agents, & the Myth of "Product Is Enough" with NFX's Gigi Levy-Weiss

Wed, 20 Aug 2025 12:00:00 +0000

Gigi Levy-Weiss is a serial founder and a Founding Partner at NFX. NFX is an early-stage firm that has established itself as one of leading experts in network effects. We talked about network effects, AI agents, the importance of speed of exectuion, why first-mover advantages are overrated, and how NFX has built its own brand, systems, and network effects.

We also covered:

Going global without going local — Despite a 10-hour time gap between Israel and Silicon Valley, NFX partners rejected the easier path of separate regional funds, instead building a fully integrated, unified investment process based on trust, asynchronous communication, and individual founder meetings.
Content as a competitive weapon — Early, sustained investment in short-form, actionable founder content gave NFX outsized market presence. Articles like the “Network Effects Bible” turned content into a persistent competitive advantage, positioning NFX as the definitive voice on network effects.
AI's future is agent-to-agent, not agent-to-human — Gigi sees current AI implementations as merely transitional (agent-to-human workflows), predicting the true revolution lies in agent-to-agent interactions, cutting entire human-dependent processes from months down to minutes.
B2C is AI’s biggest opening — Contrary to many investors betting big on AI-driven enterprise SaaS, Gigi argues consumer and SMB markets offer more attractive opportunities. Large enterprises will adapt quickly, limiting disruption, while SMBs and consumer verticals are ripe for agent-first innovation.
First-mover advantage is overrated — Gigi challenges the widely-held VC belief in the inherent value of being first. Pointing to past failures, he argues that "being great is more important than being first," and successful fast-followers often become category leaders.
Great products rarely sell themselves — Founders mistakenly obsess over perfecting product details (“product delusion”), yet distribution and defensibility usually matter more. NFX advocates for “product-market-network-distribution fit,” highlighting cases like Craigslist where distribution outshone product polish.
VC needs its own disruption — NFX built internal VC tooling (“The Force”) and founder-focused products like Signal and BriefLink, seeing tech-driven innovation as essential for winning deal flow. They reject the outdated assumption that every industry except VC itself can be disrupted by technology.

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

E35: The Pitch, Democratizing Startup Funding, and Non-Consensus Investing with Josh Muccio

Wed, 06 Aug 2025 11:00:00 +0000

Josh Muccio is the Founder of The Pitch and The Pitch Fund. The Pitch is a show that features startup founders pitching a panel of VCs and getting live-fire feedback. The Pitch Fund invests in Josh’s favorite startups that appear on The Pitch. We talked about the behind-the-scenes of how the show works, pitching, whether the market matters more than the founder, and the dangers of consensus investing.

We also dove into:

– Josh shares how selling an iPhone-repair startup and falling in love with Gimlet’s Startup podcast led him to create The Pitch to “democratize access” to startup investing and storytelling.

– Why The Pitch is “like Shark Tank for tech” but with real, check-writing VCs. Less ego, more thoughtful questions, and founders who actually get funded.

– Inside the funnel: ~1,000 companies apply each season; venture partner Peter Liu screens hundreds before Lisa Muccio and Josh decide who records—only after all three have met the founder to curb bias.

– The backstory of The Pitch Fund and Josh’s investing rubric: market > founder > product—he weights market roughly 60 % and warns that even great founders struggle in weak markets.

– Railing against “consensus chasing,” he argues that investing purely for quick mark-ups hurts returns and founders; instead, he hunts non-consensus deals—like a snack-chip startup he backed at a $4 million valuation.

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

E34: Conviction, Cheating, AI, and (Not) Predicting with Shawn Merani

Wed, 23 Jul 2025 11:00:00 +0000

Shawn Merani is the Founder and Managing Partner of Parade Ventures. Parade is a seed stage venture firm with an affinity for enterprise software. We talked about the state of seed investing, relationships, observing vs. predicting, cheating, AI and a huge win Shawn had recently with the acquisition of Moveworks. Shawn is a sharp guy and this was a really fun conversation. Please enjoy.

We also covered:

The story behind Shawn’s early bet on Moveworks — and what made the founders stand out
Why Shawn isn't big on predicting market trends
How Shawn thinks about building high-conviction, concentrated portfolios
The rise of secondary sales and what they mean for early-stage investors
Why Shawn still believes in the power of enterprise software despite the hype cycles
How he balances being relationship-driven with moving fast in today’s competitive seed market
Shawn’s candid take on AI: opportunity, overuse, and what actually matters
Why he tells his Berkeley MBA students that cheating only hurts themselves (and how he really feels about grades)

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

E33: Y Combinator, Open Source, and Lifting Founders Up with Jason Freedman

Wed, 09 Jul 2025 11:00:00 +0000

Jason Freedman is a serial founder and General Partner at Orange Collective. Orange Collective is a Y Combinator-focused venture fund that aims to invest in the most promising YC companies before Demo Day. We talked about YC, exits, AI, open source, raising founders up, and why ownership percentages are overrated. We also discussed:

YC’s radical candor + optimism
Orange Collective’s super-power: “use the product” diligence
Early, relationship-first checks beat ownership math
Real-world example: Mastra AI
Doubling down on AI infrastructure
Why open-source wins long-term
Exits require as much craft as fundraising
“Raise founders up” in practice
Ownership percentages are overrated

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

E32: Money Unplugged with Joe Magyer

Mon, 30 Jun 2025 11:00:00 +0000

Host Joe Magyer is on the other side of the microphone in this episode as we share a recent interview he did with Chris Hill on Money Unplugged. The conversation explores Joe's earliest experiences with money, including his first hustle, and his thoughts on compounding, debt, Warren Buffett, charity, and the timeless business lessons from Narcos: Mexico.

We also discussed:

The importance of early financial education and experiences.
Influence of family, especially grandparents, on financial perspectives.
Character-driven investing: the significance of doing business with good people.
Debt aversion shaped by personal experiences and family lessons.
The value of open conversations about money in families.
Understanding the long-term benefits of compounding and investing early.
The impact of Warren Buffett on the investing community and future of Berkshire Hathaway.
Personal spending should align with what brings joy and happiness.
Charitable giving can significantly improve quality of life for others.
Media can provide valuable business lessons, even in unconventional formats.

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

E31: Unlocking the Secrets of Startup Secondaries with Jamie Melzer

Wed, 25 Jun 2025 11:00:00 +0000

Our guest this week is Jamie Melzer, Managing Partner at Altra Venture Partners. Altra invests in late-stage and pre-IPO venture-backed startups via secondaries. Jamie took us on a behind-the-scenes tour of the secondary market, how it works, why it is relevant to early stage investors and founders, and where the market is heading. This was the first time we’ve talked about secondaries on Investing in Startups but it probably won’t be the last because it is becoming more important as startups stay private for longer. Please enjoy.

We also covered:

The nuts and bolts of a secondary deal—finding a seller, agreeing on price with scant data, and getting past ROFRs or outright company blocks that kill roughly a third of transactions.
Why the late-stage secondary market now looks like public-equity investing, with the top 10 U.S. unicorns (SpaceX, Stripe, OpenAI, etc.) representing more than a third of all private-tech value—a true power-law.
Common shares trading at premiums to fresh preferred rounds, and how hidden liquidation stacks can wipe you out if you don’t model the waterfall.
The surge of giant institutional funds and private-wealth vehicles buying $100-300 M blocks—versus retail SPVs chasing “Birkin-bag” names like Anduril or SpaceX, often at double the institutional price.
Lessons Jamie brought from distressed credit: pricing risk, valuing businesses bottom-up, and why share-class selection matters as much as entry multiple.
Rethinking portfolio construction: focus on position size and access, not “own 10 %,” and accept that 15-30 late-stage names can give better exposure than hundreds of seed bets.
How evergreen, index-style funds could let employees and early VCs tap liquidity every 6-12 months while letting new investors hold compounders indefinitely.
The coming “secondary-of-secondaries” wave, when today’s growth-stage and secondary funds will themselves need liquidity from even later buyers.

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

E30: AI, Anti-Patterns, and the Dangers of Elephant Hunting with Itamar Novick

Wed, 11 Jun 2025 11:00:00 +0000

Our guest this week is Itamar Novick, Founder of Recursive Ventures. Itamar is a solo capitalist with a focus on pre-seed startups built around data and AI. We talked about the opportunities and challenges that AI presents, anti-patterns to avoid in startups, winning deals, and why Itamar thinks that most VCs do NOT add value to startups. Itamar has been a founder, executive, and investor, so this was a really thoughtful, nuanced conversation.

We also covered:

Common startup mistakes that feel smart but kill companies
Lessons from a failed $50M strategic deal with ADT at Life360
What actually creates defensibility in generative AI startups
Why valuations in AI aren't a full-blown bubble—yet
Building a solo VC firm with AI as leverage (“Portfolio GPT”)
The new era of lean, high-output startups—and what it means for VC
Itamar’s go-to founder question: Why will you stay ahead five years from now?
Why most “value-add” from VCs is overhyped

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

E29: Insights From the World's Most Active Seed Investor with Antler's Tyler Norwood

Wed, 28 May 2025 10:00:00 +0000

Our guest this week is Tyler Norwood, Managing Partner for Antler in the US. Antler is the world’s most active seed investor backing founders at the inception stage from all over. We talked about the impact of vibe coding, the traits that Tyler sees in Antler’s most successful founders, why timing matters, and the value of surrounding yourself with other builders. Please enjoy.

Here are some bullets about today's show:

- Antler’s origin story and global footprint: launching in Singapore (2018) and scaling to 27 offices as the world’s most active seed investor
- The Residency model: six‑week, community‑driven program backing founders at “day ‑1” with ~US $500k checks
- U.S. expansion strategy: why New York and Austin came first and San Francisco’s “Death Star” was saved for last (plus Austin’s steep growth curve)
- Founder superpowers—aspiration + agency: how Tyler tests for them (the “strange hobby” question) and why timing‑misaligned founders struggle
- Vibe coding and generative‑AI tooling: 95 % AI‑generated codebases, faster product‑market‑fit loops, robustness can wait
- Operator‑to‑investor realities: the hard math of a first 2 & 20 fund, living on fees for ~12 years, and why VC isn’t a quick win
- Myth‑busting: the “ideas don’t matter” fallacy and the case for rigorous idea selection / founder‑market fit
- Advice for aspiring VCs and founders: patient idea formation, exposing yourself to diverse problems, and how to connect with Antler

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

E28: Han Shen on Unsexy Startups, Consumer Trends, and Investing Slightly Early

Mon, 12 May 2025 10:00:00 +0000

Our guest this week is Han Shen, Founding Partner of iFly.vc. iFly is an early-stage firm with a non-consensus, high-conviction approach to investing. Han himself is a very successful investor but also matches that success with equal levels of modesty and empathy. We talked about investing in non-consensus startups in an industry that is very consensus-driven, the vibe shift, investing with conviction, and how Han was turned down by hundreds of investors for his first fund and still lived to tell the tale. Please enjoy.

Takeaways

+ Unsexy parts of the market can yield the best opportunities.
+ Non-consensus investing allows for unique insights.
+ Consumer spending is a massive market with evolving trends.
+ Tech enablement is crucial for driving consumer innovation.
+ Listening to customers is essential for success.
+ Fundraising can be an emotional journey filled with challenges.
+ Building relationships is key in venture capital.
+ Diversity in investing goes beyond just ethnicity.
+ Concentrated investing can lead to better outcomes.
+ Continuous learning is vital for founders and investors alike.

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

E27: Should Investors Befriend Founders and Solo GP Life with Ethan Austin

Mon, 28 Apr 2025 10:00:00 +0000

Ethan Austin is the Founder and General Partner of Outside VC. Outside is a Boulder-based firm with a focus on pre-seed startups, outsider founders, and financial inclusion. We talked about why Ethan whether investors should be friends with founders, fintech, what it was like running Techstars Boulder during Covid, and life as a solo GP. We dove further into the following topics:

Origin Story is Everything: Grit and personal motivation trump polish.
Friendship = Honest Feedback: Real relationships demand tough truths.
Running a Good Fundraising Process Matters: Smart process beats a perfect pitch.
Pre-Seed Valuations Remain High: Founders must focus on momentum, not benchmarks.
Solo Doesn't Mean Slower: Solo founders and GPs can move faster without decision bottlenecks.
Financial Inclusion as a Driving Mission: Real impact over surface-level fintech hype.
Consumer Startups Reawakening: Thanks to AI, the consumer space is interesting again.

Investing in Startups explores the strategies and stories of leading early-stage VCs. The show is hosted by Joe Magyer and produced by Seaplane Ventures.

E26: The Art of Picking, Geopolitics, and Why Ideas Still Matter with Mark Peter Davis

Mon, 14 Apr 2025 10:00:00 +0000

Mark Peter Davis is the Managing Partner of Interplay Ventures. Interplay is a venture capital firm, but also an incubator and family office. Mark himself is a serial entrepreneur and also the host of the Innovation with Mark Peter Davis podcast, which is a great listen for founders. We talked about the mix of geopolitics and startups, what Mark needs to see from startups to invest, why ideas still matter, and advice on how to break into venture capital. Please enjoy.

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

E25: Tough Questions, Hustle, and Investing in Hilariously Early Startups with Elizabeth Yin

Mon, 31 Mar 2025 10:00:00 +0000

Elizabeth Yin is a General Partner at Hustle Fund. Hustle Fund invests in “hilariously early” startups in the US and beyond. We talked about Elizabeth’s favorite questions to ask founders, navigating disagreements in a healthy way, AI, the art of pitching, and why VCs should be a little more patient with founders. I really enjoyed this one and hope you do as well.

Takeaways:

Transparent Pitch Process: Hustle Fund publishes the questions they ask founders to reduce the “inside baseball” nature of VC pitching and level the playing field.

Zoom-First Approach: The fund avoids in-person meetings to ensure geographic and socio-economic equity for founders pitching them.

Favorite Founder Question: Elizabeth’s go-to question is “What is your burn rate?”—a straightforward yet revealing probe into financial discipline.

Healthy Disagreements: Disagreements within Hustle Fund’s partnership are frequent but productive, grounded in trust and transparency.

Unfair Advantage: Hustle Fund’s edge lies in ecosystem building—supporting founders through community, content, events, and distribution.

Hilariously Early Investing: Hustle Fund backs companies pre-revenue, often before product—but with a clear and nuanced understanding of the customer problem.

High Velocity Strategy: The firm backs ~250 companies per fund, mostly with a “one-and-done” strategy, occasionally following on through SPVs.

Angel Squad as a Force Multiplier: A 2,000-person global community designed to train, connect, and co-invest with emerging angels.

Founders Need to Create Urgency: Elizabeth emphasizes the importance of generating urgency in a raise—being a “great opportunity” is not enough.

Execution Speed is King: Hustle Fund prioritizes hustle—rapid experimentation and iteration—as a key signal for founder quality.

AI Investing Shift: While crowded, vertical-specific AI applications (especially in under-explored industries) still hold promise.

Patience is Under-Appreciated: Great companies like Webflow and NerdWallet often look like duds for years before compounding takes hold.

Path Flexibility Matters: Elizabeth encourages founders to evaluate what they want—venture-scale is not the only valid path to success.

VC Conventional Wisdom Challenge: She pushes back on “growth at all costs” and the notion that digital ads never work—they can, but must be used with discipline.

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

E24: Venture Alpha, Seed Investing, and Climate Volatility with Rick Zullo

Mon, 17 Mar 2025 10:00:00 +0000

Rick Zullo is the Founder and Managing Partner of Equal Ventures. Equal is a New York-based early stage venture capital firm that takes a concentrated approach with investing themes around climate, insurance, retail, and supply chain. We talked about why Rick invests with conviction, the state of seed investing, what climate volatility means for insurers and investors, and why being kind is more important than being nice. Enjoy.

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

E23: Betting Big on B2B Marketplaces with Sonia Nagar

Mon, 03 Mar 2025 11:00:00 +0000

Sonia Nagar is the Founder and Managing Partner of SNAK Venture Partners. SNAK is a Chicago-based firm that invests in Seed stage marketplace startups. We talked about why SNAK loves marketplaces, what surprised Sonia about starting a new firm, why SNAK prefers B2B to B2C, first-mover advantages, and how AI has and hasn’t changed marketplaces. Please enjoy.

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

E22: Small Funds, Big Impact: Graham Pingree on Early-Stage Trends, Portfolio Design, and the Pre-Seed Advantage

Mon, 17 Feb 2025 11:00:00 +0000

Graham Pingree is a Partner at Cendana Capital, a fund of funds firm that invests in small venture funds investing at pre-seed and seed. We talked about why Cendana is focused on small funds, why it has a concentrated strategy, what the firm looks for in emerging managers, how to think about reserves and recycling, and why big venture firms are surprisingly hard to kill.

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

E21: Venture Everywhere, Pre-Seed, and Why Venture Doesn't Scale with Jenny Fielding

Mon, 03 Feb 2025 11:00:00 +0000

Jenny Fielding is a Cofounder and General Partner of Everywhere Ventures. Jenny is a pre-seed investor with a fascinating background. She’s a founder, lawyer by training, has lived in 12 countries, and ran Techstars New York for many years. She’s also the author of Venture Everywhere, a book which comes out in March. We talked about Jenny’s strategy, why venture doesn’t scale, why everywhere doesn't use follow-on capital in its funds, and how Everywhere is navigating the Seed and AI markets.

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

Investing in Startups: https://www.investinginstartups.com/

Joe Magyer: https://www.linkedin.com/in/joemagyer/

Seaplane Ventures: https://www.seaplaneventures.com/

E20: 17 Contrarian Takes About Startups and Venture Capital

Mon, 20 Jan 2025 11:00:00 +0000

We're celebrating our 20th episode with a super cut of 17 contrarian takes on venture capital and startups. Our guests talked about AI, SF, false signals from coinvestors, why venture isn't an access game, network effects, emerging managers, portfolio construction, and more. Special thanks to the following guests for their contributions to this episode:

Niki Scevark, Blackbird Ventures

Martin Tobias, Incisive Ventures

Mike Cardamone, Forum Ventures

Nick Moran, New Stack Ventures

Mac Conwell, RareBreed Ventures

Rajiv Bala, Clutch VC

Peter Walker, Carta

Eric Golden, Canopy Capital

Colin Gardiner, Yonder Ventures

Zach Coelius, Coelius Capital

Jerry Neumann, Neu Ventures

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

Investing in Startups: https://www.investinginstartups.com/

Joe Magyer: https://www.linkedin.com/in/joemagyer/

Seaplane Ventures: https://www.seaplaneventures.com/

E19: Essential Industries, Angels, AI, and Proprietary Deal Flow with Amber Illig

Mon, 06 Jan 2025 11:00:00 +0000

Amber Illig is the Founding General Partner of The Council, an early stage venture firm focused on essential industries like supply chain and healthcare. Amber has a deep operating background having worked at Apple, Cruise, Snap, and Eli Lilly. We talked about why Amber loves essential industries, how she built a proprietary network of operator angel investors, how she and that network help support founders, and her nuanced take on AI. Please enjoy.

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

Investing in Startups: https://www.investinginstartups.com/

Joe Magyer: https://www.linkedin.com/in/joemagyer/

Seaplane Ventures: https://www.seaplaneventures.com/

E18: Sizzle, Substance, and Scaling with Winter Mead of Coolwater Capital

Mon, 23 Dec 2024 11:00:00 +0000

Winter Mead is the Founder and CEO of Coolwater Capital. Coolwater is an accelerator for emerging venture capital fund managers aimed at helping them to launch, build, and scale their firms. We talked about what investors should look for in emerging VCs, how VCs can build durable platforms, and how VCs are using AI to do their jobs better. Winter is one of the most thoughtful LPs in the venture space so it was great to have him on the show.

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

Investing in Startups: https://www.investinginstartups.com/

Joe Magyer: https://www.linkedin.com/in/joemagyer/

Seaplane Ventures: https://www.seaplaneventures.com/

E17: Spotting Winners, Platform Risk, and Why Weird is Good with Zach Coelius

Mon, 09 Dec 2024 11:00:00 +0000

Zach Coelius is the Managing Partner of Coelius Capital. Zach is a 4-time entrepreneur and now solo GP who invests in early stage technology companies. We talked about why ideas are meaningless, demo day investing, platform risk, sniffing out product/market fit, B2B2C business models, and why Zach thinks ownership is overrated. This was a really fun, candid conversation.

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

Investing in Startups: https://www.investinginstartups.com/

Joe Magyer: https://www.linkedin.com/in/joemagyer/

Seaplane Ventures: https://www.seaplaneventures.com/

E16: Syndicates, Angel Investing, and Founder-First Investing with Alex Pattis

Mon, 25 Nov 2024 11:00:00 +0000

Alex Pattis is the General Partner of Riverside Ventures. Riverside is an early stage firm that operates both a traditional venture fund but also a syndicate with more than 6,000 LPs. Alex and I talked about the rise of syndicates, how they work, why he thinks most VCs oversell the value they add to founders, and what he’s excited to invest in today. Please enjoy.

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

Investing in Startups: https://www.investinginstartups.com/

Joe Magyer: https://www.linkedin.com/in/joemagyer/

Seaplane Ventures: https://www.seaplaneventures.com/

E15: The Future of Marketplaces and Network Effects with Colin Gardiner

Mon, 11 Nov 2024 11:00:00 +0000

Colin Gardiner is the Founder and General Partner of Yonder Ventures. Colin is a marketplace geek with a fascinating career that began at the Federal Reserve, veered into startups, and now he runs his own venture firm focused on pre-seed marketplaces. We talked about the qualities that set winning marketplaces apart at the early stage, why network effects are so hard to kill, and the future of marketplaces. Please enjoy.

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

Investing in Startups: https://www.investinginstartups.com/

Joe Magyer: https://www.linkedin.com/in/joemagyer/

Seaplane Ventures: https://www.seaplaneventures.com/

E14: What's Hot in Venture with Peter Walker

Mon, 28 Oct 2024 10:00:00 +0000

Peter Walker is the Head of Insights at Carta. Peter is a self-professed data geek who publishes some of the most interesting insights and research on venture and startups today. We talked about which pockets of the venture market are going strong, why San Francisco is still the leader in venture, and why speed matters in venture capital.

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

Investing in Startups: https://www.investinginstartups.com/

Joe Magyer: https://www.linkedin.com/in/joemagyer/

Seaplane Ventures: https://www.seaplaneventures.com/

E13: Crypto, the Fed, and Venture Competition with Eric Golden

Mon, 14 Oct 2024 10:00:00 +0000

Eric Golden is the Founder of Canopy Capital and host of the Making Markets podcast. Eric was a portfolio manager and intrapreneur at Fidelity prior to setting up Canopy so he has great perspective on both markets and life as a venture-backed founder. We talked about those experiences, his current views on the Fed, markets, and crypto, and how Eric's view of venture capital has evolved over time.

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

Investing in Startups: https://www.investinginstartups.com/

Joe Magyer: https://www.linkedin.com/in/joemagyer/

Seaplane Ventures: https://www.seaplaneventures.com/

E12: Startup Accelerators, SaaS, and Helping Founders Run Faster with Mike Cardamone

Mon, 30 Sep 2024 10:00:00 +0000

Mike Cardamone is the founder and managing partner of Forum Ventures. Forum is a New York-based firm with a structure that layers together an accelerator, studio, and pre-seed fund. We talked about why Forum likes B2B SaaS, how Forum helps startups run faster, how Mike sizes up AI opportunities, and why new investors into startups might be making a mistake by following Big Brand VCs into early stage deals. We also talked about the state of play in startup accelerators and Mike's views on the direction of the space and business model. Please enjoy.

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

E11: The Rapid Rise of AI, Global Startups, and How to Treat Founders with Niki Scevak

Mon, 16 Sep 2024 10:00:00 +0000

Niki Scevak is the Co-Founder of Blackbird Ventures and a multi-time startup founder. Blackbird is the largest venture capital firm in Australia and has backed massive winners such as Canva, Zoom, and Culture Amp, among others. We talked about the power of investing early, how AI companies solve problems for customers and why they're interesting to investors, and how world-beating companies can come from anywhere. Please enjoy.

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

E10: Investing Early and Making Your Own Luck with Mac Conwell

Mon, 02 Sep 2024 10:00:00 +0000

Mac Conwell is the Founder of RareBreed Ventures, a Baltimore-based firm that invests in pre-seed and seed startups with dope founders. We had a great conversation about the types of investments that excite Mac, how the regulatory environment affects startups, and Mac’s experience of taking 4,000 meetings to get his firm off the ground.

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

E9: Founder vs. Investor, AI, and Venture Portfolio Construction with Jerry Neumann

Mon, 19 Aug 2024 10:00:00 +0000

Jerry Neumann is a wildly successful early stage investor and one of the best writers and thinkers about the craft. The founder of Neu Venture Capital talks about how he thinks about whether AI is a consensus trade in venture, the theory and reality of portfolio construction, and the origin story of an investment that returned 5000X. We also talked about the reception to a book that Jerry coauthored with Elizabeth Zalman, Founder vs. Investor.

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

E8: A Primer on Angel Investing with Rick Timmins

Mon, 05 Aug 2024 10:00:00 +0000

Rick Timmins delivers a primer on angel investing. Rick is a veteran angel investor and financier with a fascinating career. He served in senior roles with Motorola and Cisco at the height of their powers, was a semi-pro poker player, and today sits on 5 boards including the Angel Capital Association. We talked about the craft of angel investing, the potential rewards and pitfalls, and some of the lessons Rick learned from his decades of experience as a tech executive.

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

E7: Fintech and Israeli Venture with Adi Levanon

Mon, 22 Jul 2024 10:00:00 +0000

Adi Levanon is the Founder of Selah Ventures. Selah is a Tel-Aviv-based firm that is a first-check investor into fintech startups that are building in the US. We talked about fintech, why Israel has more unicorns per capita than the US, the state of the Israeli venture scene today, and the advantages of being a solo GP.

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

E6: SaaS and Seed Investing with Rajiv Bala

Mon, 08 Jul 2024 10:00:00 +0000

Rajiv Bala is the Co-Founder of Clutch VC. Clutch is an Austin-based firm that makes Seed investments in B2B software. We talked about the importance of staying true to your investment thesis, the strategy that enabled Clutch to raise a strong first fund despite a terrible environment, and whether it’s true that you have to be in a billion dollar deal to produce a great venture fund. Please enjoy.

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

E5: Nick Moran on Investing in Outsider Founders

Mon, 24 Jun 2024 10:00:00 +0000

Nick Moran is the Founder and General Partner of New Stack Ventures. Nick is also the host of The Full Ratchet, the first VC podcast that started back in May 2014. We discussed how New Stack adds value, why Nick is focused on deals outside the Bay area, and why access is overrated. Please enjoy.

Investing in Startups is produced by Seaplane Ventures. You can follow host Joe Magyer on LinkedIn or on X at @Magyer.

E4: Avlok Kohli on the State of Play in Venture

Mon, 10 Jun 2024 10:00:00 +0000

Avlok Kohli is the CEO of AngelList. Avlok is a serial entrepreneur who came on to lead AngelList in 2019. The platform has grown massively since then and now has $124 billion in assets. We explore AngelList's strategy, the state of play in venture, why GPs shouldn't get their hopes up for a liquid secondary market, and Avlok's approach to angel investing.

Investing in Startups is produced by Seaplane Ventures. You can follow host Joe Magyer on LinkedIn or on at @Magyer.

E3: Morgan Housel on What Never Changes in Investing

Mon, 27 May 2024 10:00:00 +0000

Our guest this week is Morgan Housel. Morgan is a partner at Collaborative Fund and the best-selling author of The Psychology of Money and his new book, Same As Ever. He is an award-winning columnist from his days of writing for The Motley Fool and The Wall Street Journal. We discussed what you can and can’t learn from studying great investors, what surprised Morgan about moving from public to private markets, and what Morgan has changed his mind on over the years. It was a really fun conversation. Please enjoy.

Investing in Startups is produced by Seaplane Ventures. You can follow host Joe Magyer on LinkedIn or on X at @Magyer.

E2: Chris Douvos on Backing Emerging Managers

Mon, 13 May 2024 10:00:00 +0000

Our guest this week is Chris Douvos, the Founder and Managing Director of Ahoy Capital. We explore why Chris is focused on emerging managers, what led him to a concentrated strategy, what he has changed his mind on over the years, and what keeps him up at night. Please enjoy this fun conversation.

Investing in Startups is produced by Seaplane Ventures. You can follow host Joe Magyer on LinkedIn or on X at @Magyer.

E1: Martin Tobias on Pre-Seed Investing

Mon, 29 Apr 2024 10:00:00 +0000

Our guest this week is Martin Tobias, the Founder of Incisive Ventures. Incisive is a Seattle-based firm that invests in pre-seed software startups in the US and beyond. Prior to starting Incisive, Martin was a highly successful angel investor and a serial entrepreneur who served as the CEO of 3 venture-backed startups.

We discuss why Martin loves pre-seed investing, valuation trends, the challenges and opportunities that come with investing abroad, and why investors should be careful to not put too much weight on the reputations of their coinvestors.

Investing in Startups is produced by Seaplane Ventures. You can follow host Joe Magyer on LinkedIn or on X at @Magyer.