Post Money

AI is moving faster inside enterprise software than most companies can handle, especially in coding, where development speed is now outpacing security. In this episode, Peter McKay, CEO of Snyk, breaks down how AI is changing software development, DevSecOps, and enterprise security, and what it actually takes to keep up.

We talk about how Snyk scaled from $2M to $350M ARR and what really drives that kind of growth. Peter talks openly about why he had to reinvent himself before he could transform the company, how to know when your team can’t scale with the business, and why making those decisions early is one of the hardest parts of being a CEO.

We also cover capital strategy, scaling teams, acquisitions, and what founders consistently get wrong about raising and spending money. And finally, we go deep on what it means to build in a market where competition is accelerating fast and why, in Peter’s words, you always have to be “swimming in front of the sharks.”

Inside the episode:

* How AI is accelerating software development faster than security can keep upand why this is becoming a critical enterprise risk

* The shift from internal AI tools to customer-facing AI applications and what breaks when you scale them

* How Snyk embedded security directly into the development lifecycle

* Scaling from $2M to $350M ARR: the real growth levers

* Redesigning workflows for AI instead of layering tools on outdated systems

* The hardest leadership challenge: knowing when your team can’t scale with the business

* How to make difficult team decisions before things break

* Capital strategy: when to raise, how much to raise, and why cash discipline matters

* Why Snyk kept $365M in the bank

* Managing boards and investor dynamics during high-pressure decisions

* The reality of being a CEO

* “Swimming in front of the sharks” — how to compete in a market dominated by OpenAI, Google, and Anthropic

Watch Full Episode on YouTube

About Peter McKay:

Peter McKay is a five-time CEO and one of the most experienced operators in enterprise software, with a track record of scaling and exiting multiple companies across cybersecurity and infrastructure.

He is currently the CEO of Snyk, where he led the company from just a few million in revenue to over $350M ARR, transforming it into one of the leading DevSecOps and AI security platforms. Before Snyk, Peter held CEO roles at companies including Veeam and Desktone, and has been involved in several successful exits to companies like VMware and IBM.

Known for his operator mindset, Peter focuses on execution, speed, and making decisive bets ahead of market shifts, including pushing early into AI while most companies were still experimenting.

Connect with Peter McKay: https://www.linkedin.com/in/pemckay/

Converge VC website: https://converge.vc/Connect with Nilanjana Bhowmik: https://www.linkedin.com/in/nilanjanabhowmik/

Cash runway determines whether a startup survives long enough to find product-market fit, navigate a market shock, or become a category-defining company. In this episode, Maia Heymann, Co-Founder and General Partner at Converge VC, explains why runway is not just a financial metric but a strategic asset, why dilution is often a smaller risk than founders think, and why early-stage venture debt can quietly destroy even strong companies. From fundraising in volatile markets to the psychological traps around ownership, Maia breaks down the capital decisions that separate startups that live to fight another day from those forced into weakness, distress, or premature exits.

Inside the episode:

* How founders should think about raising more capital than they think they need in uncertain markets

* How exogenous shocks (market crashes, banking crises, macro events) instantly change fundraising dynamics

* Why dilution is cheaper than death for venture-backed startups

* The hidden danger of venture debt, especially for early-stage companies without real financial flexibility

* Why startups often get forced into selling from a position of weakness

* What separates the startups that survive downturns from the ones that collapse

* Why some of the best companies are actually 20-year overnight successes

* When founders should listen to their investors, and when they absolutely should not

* How SaaS founders should think about today’s market reset and AI pressure

* The shift from pure growth to capital efficiency and strategic positioning

Watch full episode on YouTube:

About Maia Heymann:

Maia Heymann is Founder and General Partner at Converge VC, bringing over 25 years of experience investing in and financing B2B technology companies. Her career spans venture capital, structured debt, and technology banking, giving her a rare, full-spectrum view of how startups are built, funded, and scaled.

She has spent two decades in venture, partnering closely with founders and backing disruptive technology companies, with prior experience launching BancBoston Ventures’ West Coast office in Palo Alto. Across her career, Maia has been involved in more than 60 M&A transactions, 7 IPOs, and over 25 board and observer roles,shaping companies through critical moments of growth, inflection, and exit.

Before founding Converge, Maia led BancBoston Ventures’ $340M portfolio following its merger with Bank of America, and served as Managing Director at Shott Capital, overseeing $2.7B in LP commitments to venture capital funds prior to its acquisition by Hamilton Lane. Earlier in her career, as a technology banker in Silicon Valley, she underwrote over $2.5B in structured debt facilities to finance acquisitions for technology companies.

Maia is known for her ability to build strong board dynamics, align stakeholders, and support founders through complex decisions.

Artificial intelligence is rapidly becoming the new interface for how we access information, shop online, and interact with the digital world. Entire industries built around the web as we know it, including media, search, e-commerce, and even logistics, are being quietly rewritten underneath us.

In this episode, Ben Lerer, Managing Partner at Lerer Hippeau, explains why AI agents could become the new front door to the internet and what that means for founders, investors, and incumbents. From the collapse of generalized content creation to the rise of AI-driven commerce and autonomous logistics, Ben breaks down the next generation of billion-dollar opportunities.

The conversation explores how companies like OpenAI could expand far beyond software into massive physical markets such as commerce, grocery, and logistics, why autonomous delivery networks like Zipline may become foundational infrastructure, and how AI-powered consumer platforms like Hungryroot hint at a future where intelligent agents manage everyday decisions such as meal planning and shopping.

Inside the episode:

* How AI agents could become the primary interface for commerce and online discovery

* The rise of autonomous logistics networks and why companies like Zipline have a decade-long advantage

* How AI-powered grocery and meal planning platforms are reshaping consumer behavior

* The collapse of SEO-driven content and the end of the listicle economy

* Why large technology companies such as OpenAI, Google, and Amazon are positioned to expand into entirely new industries

* How venture capital firms evaluate opportunities during periods of massive technological disruption

* Why distribution, infrastructure, and data advantages will define the next generation of category-defining startups

Watch full episode on YouTube:

About Ben Lerer:

Ben Lerer is Managing Partner at Lerer Hippeau, one of the most active early-stage venture capital firms in the United States, known for backing category-defining consumer and technology startups. The firm has backed companies that went on to become major global brands including Warby Parker, Allbirds, Zipline, and Hungryroot.

Before entering venture capital, Ben was an entrepreneur in the digital media industry. He co-founded Thrillist, which grew into one of the most prominent digital lifestyle media brands before merging with Group Nine Media, later acquired by Vox Media.

Through his work at Lerer Hippeau, he continues to back founders building companies that leverage emerging technologies to reshape industries ranging from logistics and consumer products to AI-native platforms and digital infrastructure.

Converge VC website: https://converge.vc/

Connect Ben Lerer: https://www.linkedin.com/in/benlerer/

Connect with Nilanjana Bhowmik: https://www.linkedin.com/in/nilanjanabhowmik/

When $300B gets wiped off SaaS market caps, it’s usually not just sentiment, it’s the market sensing a platform shift. AI agents are replacing per-seat SaaS software, vector databases are becoming the memory layer for large language models (LLMs), and knowledge infrastructure is emerging as the real foundation of enterprise AI. In this episode, Ash Ashutosh, CEO of Pinecone, explains why LLMs need a new database category, why traditional databases break in the age of semantic search, and how vector databases are powering the next generation of enterprise AI.

Inside the episode:

* Why production AI requires purpose-built memory infrastructure

* How Pinecone grew to 9,000+ paying customers and 800,000+ developers

* The shift from experimentation to enterprise-scale deployment

* How token costs and context management are becoming core design constraints

* Why the $300B SaaS wipeout signals a structural shift

* The death of per-seat pricing in an agent-driven world

* Why LLMs are powerful and yet fundamentally broken without memory

* The four defects of LLMs

* Why traditional SQL and document databases fail under semantic search

* Vector databases explained simply: storing meaning, not rows

* Why multi-agent systems make 96% accuracy dangerously insufficient

* Where the next $100B AI companies might actually be built

Watch full episode on YouTube:

About Ash Ashutosh:

Ash Ashutosh is a multi-time founder who has repeatedly built and defined entirely new data categories. He founded AppIQ in 2001, pioneering storage resource management before its acquisition by HP. He later built Actifio, creating the copy data management category, which was acquired by Google. Today, as CEO of Pinecone, Ash is leading one of the most important infrastructure shifts in AI, building the vector database layer powering enterprise large language models and agentic systems. Few operators have shaped as many foundational layers of the data stack and fewer still are doing it again at the dawn of the AI era.Converge VC website: https://converge.vc/Connect with Ash Ashutosh: https://www.linkedin.com/in/ashashutosh/Connect with Nilanjana Bhowmik: https://www.linkedin.com/in/nilanjanabhowmik/

When software leaves the screen and starts controlling the physical world, the venture playbook changes. For the last decade, venture capital has concentrated in asset-light SaaS businesses where growth is measured in dashboards and defensibility is defined by retention curves. Sunil Nagaraj has built his firm around a different premise: that the next wave of venture-scale outcomes will come from embedding software and AI into the physical world. From programmable dairy farms to modular satellites and digitized school transportation systems, Sunil’s thesis “software beyond the screen” focuses on companies that combine hardware substrates with software control loops to modernize large, historically underserved markets. In a world where AI compresses development cycles and traditional SaaS moats face pressure, he argues that disciplined, capital-efficient deep tech may offer stronger long-term defensibility than pure software alone.

Inside the episode:

* Why investing off the beaten path allows you to define the fundraising rubric

* Why Sunil is not looking for “bold” founder, but careful, surgical operators

* How Halter turned dairy cows into programmable systems and built a billion-dollar company

* The biggest mistake technical founders make when selling into traditional industries

* Why $2–3M should be enough to get a deep tech product into customers’ hands

* How AI enables closed-loop control in physical systems

* Why intuitive, no-manual interfaces will unlock the next wave of adoption

* Why space investing became viable once it became modular and predictable

* Why you must underwrite for IPO, not M&A, in overlooked markets

* How Sunil runs a concentrated solo GP strategy with board seats and founder flywheels

Watch full episode on YouTube:

About Sunil Nagaraj:

Sunil Nagaraj is the Founder and Managing Partner of Ubiquity Ventures, a seed-stage venture capital firm managing approximately $200 million across three funds and built around a “nerdy and early” investment philosophy. Ubiquity backs founders at the earliest stages, often pre-incorporation, who are embedding software, AI, and sensors into the physical world through what Sunil calls “software beyond the screen.” Over 15 years in venture, he has led seed and Series A investments in companies that have grown to a combined market capitalization of over $40 billion, including six unicorns, returning more than $2 billion to LPs. Prior to founding Ubiquity, Sunil spent nearly a decade at Bessemer Venture Partners, where he led early investments in Auth0 (acquired by Okta for $6.5B), Zapier, Rocket Lab (NASDAQ: RKLB), and Twitch (acquired by Amazon for $1B). Earlier in his career, he was founder and CEO of Triangulate, a venture-backed machine learning dating startup, and worked at Bain & Company, Cisco, and Microsoft.

If you’re trying to predict the next unicorn by pattern-matching the last one, you’re probably already behind. In this episode, Anne Dwane of Village Global explains why predicting startup outliers has never been more difficult, how AI is quietly reshaping venture capital strategy, and why diversified 100-company seed portfolios may outperform concentrated conviction bets.

Drawing on her journey from founding Military.com through the dot-com crash to serving as Chief Business Officer at Chegg and now General Partner at Village Global, Anne breaks down the logic behind broad portfolio construction, scout-driven deal flow, disciplined entry valuations, and why capital efficiency often beats mega rounds.

Inside the episode:

* Why every startup journey is “like driving a Humvee across the desert” and what the dot-com crash taught about durable business models

* Why the next trillion-dollar company probably won’t look like the last one

* How Village Global builds a diversified seed portfolio of ~100 companies using 30+ operator scouts

* What “narrative engineering” means and why storytelling now differentiates founders

* Why private markets can “hide sins” but public markets expose weak fundamentals

* How agentic tools, usage-based APIs, and collapsing transaction costs are reshaping the theory of the firm

* Why leadership now matters more than management in an AI-driven world

Watch full episode on YouTube:

About Anne Dwane:

Anne Dwane is a venture capitalist and former tech founder, venture-backed CEO, and public company executive with over 20 years of experience scaling companies from startup through IPO. She has managed full P&Ls, built high-performance teams, and developed products and services used by tens of millions of customers. Anne led two companies to successful acquisitions by Monster and Chegg, identified and integrated more than six acquisitions, and held P&L responsibility before and after Chegg’s IPO, when the company reached a valuation exceeding $1B.

Seed-stage venture capital is often described as a people business, but very few firms are structurally built around that reality. In this episode, Brad Svrluga, co-founder of Primary, explains why his firm deliberately rebuilt the seed VC model to operate more like an execution platform than a traditional investment partnership. Instead of optimizing for GP economics, Primary reinvests management fees into a large, senior operating team that supports founders on talent, go-to-market execution, customer development, and capital strategy from day one.

The conversation goes deep into seed-stage governance, including why boards often add friction too early, what productive board involvement actually looks like, and how focus and prioritization matter more than formal control at the earliest stages. Brad also shares lessons from 25 years in venture capital, why investing is fundamentally an apprenticeship business, and why learning to make money in venture first requires losing it.

Inside the episode:

* Why most seed-stage venture firms are structurally misaligned with founder success

* How Primary built one of the largest operating teams in seed investing and why scale matters even before product–market fit

* The real reason early hiring mistakes kill startups

* Why the best founders actively seek operational leverage instead of “staying lean” or avoiding help

* Why being a founder’s “first call” requires infrastructure, not just experience or good intentions

* What a 25-deal fund with nine unicorns reveals about breadth vs. single-outlier portfolio construction

* Why founder quality consistently outweighs product and market at the seed stage

* What venture boards should never spend time on

* How AI is compressing both success and failure timelines for startups

* How portfolio scale becomes more important when failure rates rise but outliers get bigger

Watch Full Episode on YouTube:

About Brad Svrluga:

Brad Svrluga is a co-founder and General Partner at Primary Venture Partners. He began his career in venture capital at the very end of the internet bubble and invested through the difficult market cycles of the early 2000s. His investment focus spans vertical SaaS, healthcare, and financial services, and he has partnered with multiple companies in each of these sectors that have gone on to exceed $1B in valuation.

Together with co-founder Ben Sun, Brad helped scale Primary into what is now the world’s largest standalone seed-stage venture firm. He currently serves as Managing Partner and co-leads the firm’s investment team.

If you’re waiting for clean metrics before trusting product-market fit, you’re probably already behind. In this episode, Kent Bennett explains how early product-market fit actually shows up in the real world, why customer behavior matters more than spreadsheets, and how some of the most successful venture-backed companies were recognized before the data looked obvious.

Kent draws on nearly two decades at Bessemer Venture Partners, sharing lessons from companies like Toast, Shopify, Twilio, and Wix. He breaks down why traditional venture metrics often lag reality, how AI is reshaping early signals, and why investors who start with teams or trends often miss what matters most.

Inside the episode:

* Why real product-market fit often shows up through customer behavior, not revenue charts

* How Toast quietly proved demand when coffee shops and restaurants replaced “working” systems

* Why most early-stage metrics are lagging indicators and misleading at seed and Series A

* How Kent evaluates startups before ARR, payback periods, or clean dashboards exist

* Why AI has increased both the strength of early signals and the number of false positives

* How founders and investors should think about companies that won’t become venture-scale outcomes

* Why stopping, selling, or changing course can be the most rational decision

* Why the “death of SaaS” narrative is overblown

* Final advice for founders: don’t build “AI for X”

Watch full episode on YouTube:

About Kent Bennett:

Kent Bennett is a partner at Bessemer Venture Partners, where he focuses on B2B application software and consumer “earthquakes”, categories where shifts in behavior create entirely new markets. His investing lens is shaped by a deep interest in how products earn real adoption before they earn headlines.

Before venture capital, Kent followed an unconventional path. He worked as a creative executive at an entertainment production company, developing and selling original projects including a network television pilot and a feature film, before beginning his professional career at Bain & Company across sectors such as IT, retail, consumer products, healthcare, and biotech. He holds an MBA from Harvard Business School, where he was a Baker Scholar, and graduated summa cum laude in systems engineering from the University of Virginia as a Jefferson Scholar.

The U.S. Department of Defense is one of the largest buyers of technology in the world and yet most founders and venture investors still don’t understand how defense spending actually fuels startup growth. In this episode, Alexander Harstrick explains how government capital quietly de-risks early-stage technology, why dual-use startups are gaining an advantage, and how shifts inside the Pentagon since 2014 have reshaped venture capital, defense tech, and early-stage investing.

Alex shares his unconventional path from consulting and corporate investing to military service, Pentagon acquisitions, and ultimately founding J2 Ventures. He explains how shifts inside the DoD since 2014 have opened the door for startups to work with the government faster, earlier, and with far less friction than most founders and investors realize.

Inside the episode:

* Why the U.S. government has historically been the largest and most overlooked source of early technology risk capital

* How dual-use companies can use government dollars to de-risk product–market fit without sacrificing commercial focus

* Why most founders misunderstand how DoD procurement actually works and who really controls billion-dollar budgets

* The barbell strategy for startups: using defense as early validation or as a scaled enterprise customer

* Why many defense-focused funds are likely to fail and what investors consistently get wrong about this market

* How companies like Aura, Palantir, and other dual-use businesses quietly unlocked massive government contracts

* Why building products only for the Department of Defense is almost always a strategic mistake

Watch full episode on YouTube:

About Alexander Harstrick:

Alexander Harstrick is a Managing Partner at J2 Ventures, investing in dual-use and deep-tech companies at the intersection of defense, government, and commercial markets. He brings an operator’s perspective shaped by experience in venture investing, military intelligence, and national security innovation.

Before J2, Alexander worked in corporate venture investing at Horizon Blue Cross Blue Shield, served as a U.S. Army Military Intelligence Officer with deployments to Afghanistan and Iraq, and led early-stage technology investments inside the Department of Defense through the Defense Innovation Unit and National Security Innovation Capital. He has also worked with KKR and supported strategic finance initiatives for the U.S. Air Force via AFWERX.

Most venture capital stories start with wins, but this one starts with bankruptcy.

In this PostMoney Podcast episode, Nihal Mehta, co-founder and managing partner at ENIAC Ventures, recounts how failing publicly in his early 20s, including filing for Chapter 7, shaped his view of founders, risk, and what actually matters in the zero-to-one stage. From meeting his partners as engineering students at the University of Pennsylvania to building ENIAC over 16 years into its sixth fund, Nihal explains why survival, not hype, is the real compounding advantage.

Drawing from his experience as a serial founder before becoming an investor, Nihal breaks down why ENIAC was deliberately built as a founder-led, “anti-VC” firm, why resilience and grit are earned only through failure, and why staying lean and close to customers matters more than polished strategy decks. He shares how ENIAC helps founders through product-market fit, why shipping fast beats perfection whether you’re B2B or B2C, and what it really takes to earn the right to raise a Series A in today’s market.

Inside the Episode

* Bankruptcy, Chapter 7, and the founder scars that shaped ENIAC

* How four founders met at UPenn and built a firm over 16 years

* Why ENIAC was designed as a founder-led “anti-VC”

* “Just stay alive”: why survival is the most underrated startup strategy

* Product-market fit: shipping fast, staying lean, and listening to customers

* Seed vs Series A today: check sizes, valuations, and rising expectations

* Why many strong companies are overlooked in a growth-obsessed market

* Human unicorns, repeat founders, and execution over ideas

* How AI is changing who can build companies

Watch Full Episode on YouTube:

About Nihal Mehta

Nihal Mehta is a co-founder and managing partner at ENIAC Ventures, a founder-led seed-stage firm he’s helped build over 16 years. Before venture capital, Nihal was a serial founder who experienced both exits and failure, including a Chapter 7 bankruptcy in his early 20s, followed by acquisitions of ipsh! by Omnicom and buzzd/LocalResponse by BlueCava. He began investing early, backing companies such as AdMob (acquired by Google), Alloy, Brightwheel, Tala, and Uber. Alongside his wife Reshma, he is an active angel investor and LP supporting underrepresented founders, and is deeply involved in philanthropy through initiatives like Project Ahimsa and Help Main Street.