Investing in Startups

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.  

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.

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.

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. 

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.

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.  

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.

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. 

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.   Other topics include:   The Bay Area fosters a unique culture of openness and innovation. Building a community is essential for networking and support in FinTech. Fundraising for venture capital can be challenging, especially for emerging managers. Talent in FinTech has significantly improved over the past decade. FinTech companies are increasingly taking market share from traditional banks. Vertical SaaS is a growing trend that could disrupt traditional banking. Mortgages may become a viable second product for FinTech companies. Early-stage investors can leverage their networks to help founders succeed. The series A market is evolving, with changing metrics for success. The LP ecosystem is slow to adapt, impacting venture capital dynamics.   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.