Investing in Startups

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, Managing Partner and founder of Precursor Ventures, shares his expertise as a seasoned investor in over 400 startups. He emphasizes the importance of founder-centric investing, the challenges of liquidity in early-stage ventures, and the need for a resilient firm structure. Hudson also discusses how market forecasting can be tricky, advocating for focusing on founders instead. He provides insights on varying LP expectations and the potential pitfalls of early employee hires, highlighting the evolving landscape of venture capital.

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.