The VentureFizz Podcast

Episode 452 of The VentureFizz Podcast features Liam Donohue, Co-Founder and Managing Partner at .406 Ventures. I’ve had the opportunity to interview other partners at .406 Ventures like Payal, Kathryn, and Graham… but as .406 Ventures is celebrating a 20 year milestone for the firm, it was only fitting to interview Liam to discuss his career and reflect on the firm’s history and journey. Over the last two decades, the firm has raised more than $1.3 billion across five core funds and three opportunity funds, along with 100 investments. They’ve backed category-defining winners across cybersecurity, data and AI, and healthcare including iconic names like Carbon Black, CloudHealth, Veracode, Iora Health, and many others. But what I think helps to truly set .406 apart is that a third of their investments are with repeat .406 founders. In this episode, we cover: * Liam’s background story and how he got his career started. * How he discovered venture capital and ultimately founded Arcadia Partners, and backed early health innovators like HealthDialog. * The founding story of .406 Ventures and how Ted Williams’ approach to the plate inspired their disciplined investment focus. * A deep dive into the healthcare industry, plus use cases for AI. * The Series B funding landscape and why later rounds take on more a national flavor and what investors are expecting for growth metrics. * Why Boston remains an unmatched epicenter for startups. * And so much more! Podcast Sponsor First Citizens Innovation Banking serves innovative Tech, Healthcare and Life Science companies, including 50% of the Forbes 2026 Fintech 50, and 42% of the CNBC 2026 Disruptor List. With more than 1,500 bankers and relationship advisors and $48B in loans as of Q2 2026 – First Citizens Innovation Banking delivers expert guidance, specialized products and a team that knows the innovation economy inside and out. Learn more at innovation.firstcitizens.com. Where Silicon Valley Banks.

Episode 451 of The VentureFizz Podcast features Vinay Seth Mohta, CEO & Co-Founder of Manifold. Vinay has spent his entire career at the cutting edge of complex data and systems. He cut his teeth as employee #29 at Endeca, went on to co-found Kyruus - building the healthcare industry’s leading patient access platform using machine learning and then co-founded Manifold in 2017, launching with its AI mission the very same year the foundational Transformer paper was published. Manifold is the enterprise agent platform for life sciences. The company is on a mission to accelerate life-changing medicines to patients from early discovery to the clinic. Manifold has raised $40M to date from leading investors including Reach Capital, SilverArc Capital, Industry Ventures, TQ Ventures, and Calibrate Ventures. In this episode, we cover: * Essential advice for entrepreneurs building tech startups in the highly complex, regulated healthcare industry. * Vinay’s background story and his formative experience at Endeca. * Working alongside Paul English at KAYAK and the famous "red phone" customer obsession story. * His journey into entrepreneurship and co-founding Kyruus using machine learning to tackle the complex matching problem between patients and physicians. * All the details on Manifold’s AI platform and use case examples. * Advice on raising follow-on rounds of funding and growth expectations in today’s venture landscape. * The lessons learned transitioning from Co-Founder & CTO to the Co-Founder & CEO seat. * And so much more! Podcast Sponsor First Citizens Innovation Banking serves innovative Tech, Healthcare and Life Science companies, including 50% of the Forbes 2026 Fintech 50, and 42% of the CNBC 2026 Disruptor List. With more than 1,500 bankers and relationship advisors and $48B in loans as of Q2 2026 – First Citizens Innovation Banking delivers expert guidance, specialized products and a team that knows the innovation economy inside and out. Learn more at innovation.firstcitizens.com. Where Silicon Valley Banks.

Episode 450 of The VentureFizz Podcast features Ben Nye and Sage Nye of Venture Guides. Ben was a guest on The VentureFizz Podcast eight years ago for Episode 50, so it is only fitting that he is a 2nd time guest 400 episodes later. Perfect timing! https://soundcloud.com/venturefizz/episode-50-ben-nye-ceo-at-turbonomic Back then, Ben was the CEO of Turbonomic which was acquired by IBM in 2021 for a massive exit. Ben has gone on to launch Venture Guides along with Sage, who is a founding team member. The format of this podcast is very different for me. I was onsite at their offices at 100 Causeway in Boston and took a tour with Ben and Sage. Let’s just say, Boston needs more investors like Venture Guides. Yes, lots of VC firms have their lane for stage of investing and might be focused on a particular sector, but Venture Guides is different and I saw it first hand. There are many reasons, but here are two examples: First, their office includes a very large shared working space for their portfolio companies. On the tour, they shared details on several of them: Assail, VibeIQ, SpartanX, Memcyco, IO River, EON, Hoop.dev, env zero, Precog, Odigos, and Elastio. The best part… only 2 of the companies that are currently located at Venture Guides were started in Boston! Yes, Venture Guides is recruiting companies to Boston. Second, Venture Guides runs a sales training program for recent college graduates to support hiring for the Go-To-Market teams with ready-to-hire sales candidates for their portfolio companies. It is run by Dave Boffa, who was the GM of North American Sales at Rapid7 and in a small world moment, Dave and I actually worked together many, many moons ago. After our tour, we sat down in the Venture Guides’ podcast studio which is where they record their own podcast called Built Not Born, to do a deeper dive into lots of topics like: * Sage’s background and the early beginnings of her career in the tech industry at around 12 or 13 years old. * The story of the Turbonomic acquisition. * How Venture Guides came together and how they guide founders along the way. * Advice on storytelling and building a scalable go-to-market motion. * The firm’s progress to date and portfolio momentum. * And more!

Episode 449 of The VentureFizz Podcast features Doug McNary, CEO of commercetools. 11 exits as a CEO or board member. That is an incredible and extraordinary number, and that is Doug’s track record. You would be hard-pressed to find another executive with the same history of success, not only in the Boston tech scene, but also beyond. He came up through the sales ranks to leading go-to-market organizations at high-flying tech companies like Tivoli and Motive before taking his first position as CEO of Onaro and he has been a magnet for success ever since. Fast forward across multiple CEO roles and board seats, today Doug is the CEO of commercetools, the global digital commerce AI company that helps enterprises transform commerce for the AI era. More than 500 global brands, retailers, and enterprise companies rely on commercetools to power their digital commerce.  In this episode, we cover: * Key advice on building a vertical AI company and why you must know your customer well enough to do their job. * Advice for operators with aspirations to become a CEO and how boards evaluate candidate readiness. * Lessons learned scaling software companies through major inflection points to successful exits. * The evolution of eCommerce and AI’s impact. * All the details about commercetools and how its API-native architecture positioned it for the AI era. * The primary responsibilities of an effective board member and how to get on the radar for board seats. * Crucial advice on building a repeatable enterprise GTM function, mastering outbound sales, and hiring top sales leadership. * And more!

Episode 448 of The VentureFizz Podcast features Benj Cohen, Founder & CEO of Proton AI. The wholesale distribution industry in the US is a massive $9 trillion-a-year market yet one that most tech founders know very little about. Benj’s connection to distribution runs very, very deep. His family’s history in the industry spans four generations, going back 100 years to his great-grandfather selling dental supplies out of a suitcase and starting a dental supply company that still exists today. He was engrained in the family business to the point that he actually made his first sales attempt when he was just four years old, while tagging along with his dad on sales calls. While studying applied mathematics and rowing crew at Harvard, Benj realized that while wholesale distribution runs on massive amounts of transaction data, the core systems running these multi-million dollar businesses were 30-year-old green-screen mainframes. He saw an opportunity to leverage machine learning to help distributors modernize, cut through manual friction, and drive sales. This led to him star the company while still in college and fast forward to today, Proton is the first industry cloud for distribution. Its growing suite of modular products connect on one AI-powered platform, so distributors can grow revenue, protect margins, and give their people time back. The company is backed by Felicis and Battery Ventures. In this episode, we cover: * Key advice on building a Vertical AI company and why you must know your customer well enough to do their job. * Benj’s background growing up in Pennsylvania and what he learned from the family business. * Building on top of legacy green-screen mainframes and pulling multi-source data into an AI native stack. * How Proton expanded from their original CRM application to other products and the decision around the timing to do so. * The importance of having core company values that actually have meaning and how it translates to an effective hiring straregy. * Proton’s GTM strategy. * And so much more! Podcast Sponsor First Citizens Innovation Banking serves innovative Tech, Healthcare and Life Science companies, including 50% of the Forbes 2026 Fintech 50, and 42% of the CNBC 2026 Disruptor List. With more than 1,500 bankers and relationship advisors and $48B in loans as of Q2 2026 – First Citizens Innovation Banking delivers expert guidance, specialized products and a team that knows the innovation economy inside and out. Learn more at innovation.firstcitizens.com. Where Silicon Valley Banks.

Episode 447 of The VentureFizz Podcast features Steve Kaufer, serial entrepreneur & tech CEO - The Definitive Story of TripAdvisor. People often ask me how I land guests for my podcast. After 8 years of podcasting and over 450 episodes, I’m fortunate to get a lot of amazing inbound requests. But another key way I land guests is at events, and this episode is a perfect example. Back in July, I was fortunate to attend Founder Collective’s summer party and spotted Steve in the crowd. I had never met him before, but I knew this was my chance to land him as a guest and record the definitive story of TripAdvisor. Needless to say, I was thrilled when he said yes to my invite. Similar to my recent interview with Eran Egozy, co-founder of Harmonix, creators of the Guitar Hero and Rock Band franchises.., we went long-form, Joe Rogan style. This interview is almost two hours long, but we obviously had a ton to cover. TripAdvisor is one of the greatest consumer success stories to come out of Boston, but I don’t think we give the company enough credit for its sheer scale and impact. While TripAdvisor didn’t invent user-generated content or online reviews, it basically institutionalized both well ahead of the pack. Their marketing strategy is absolutely brilliant, as you see their brand everywhere, and hotel operators regularly ask guests to leave reviews. What’s also remarkable is that the company raised just over $4 million in capital, and only four years later exited for over $200 million to IAC before later spinning out as its own public ticker. It’s extremely rare to have the same co-founder serve as CEO through every single phase of a company from its origins as a B2B model (yes, originally a B2B model) through hypergrowth and navigating a global pandemic. Steve shares incredible stories and hard earned advice from across that journey. In addition to the full lifecycle story of TripAdvisor, we also discuss his previous company, Centerline Software – which ended up not being the return that investors had hoped for, plus his current mission driven venture, Give Freely, a browser extension and charitable giving platform. #startups #tripadvisor, #entrepreneurship #consumer #podcast

Episode 446 of The VentureFizz Podcast features today’s guest is Jack O’Brien, Co-Founder & CEO of Subconscious. AI agents are rapidly transforming knowledge work, especially in sectors like software engineering, law, and finance. However, inference costs for AI agents present a massive challenge, as agentic workloads love chewing up tokens which in return ends up costing companies lots and lots of money. And context limits or rate limits are not the answer either. Subconscious was built to solve this exact challenge. Based on research out of MIT, Subconscious has built a specialized inference platform designed specifically for long-horizon AI agents. Using dynamic context compression and efficient caching, the platform allows developers and enterprises to run open-weight models faster, longer, and up to 80% cheaper. It reminds me of another company that was based on research out of MIT back in 1997: local tech giant Akamai, who helped speed up the internet based on distributed computing and intelligent routing. Subconscious recently announced $5.1 million in funding led by MassVentures, with participation from Foothill Ventures, Underscore VC, E14 Fund, Oakseed Ventures, and the Agent Fund. In this episode, we cover: * Jack’s background story, including being the nation’s top-ranked face-off specialist in lacrosse, his career in D1 lacrosse at Princeton, and his early entrepreneurial experience running Tiger Bed Rentals as a student through its acquisition. * His time as a software engineer at Google and what this experience taught him. * His serial startup journey, including building OnePager and its acquisition by Stonks. * The origin story of Subconscious and meeting his co-founder, Hongyin Luo. * How Subconscious’s inference runtime uses dynamic context compression to slash token costs while maintaining or even improving model performance. * Details on their newly announced $5.1M round of funding. * The rise of open source LLM’s versus closed frontier models. * His personal passions outside of work, including kite surfing. Podcast Sponsor: This podcast is brought to you by one of the strongest longtime supporters of the local startup ecosystem, Silicon Valley Bank, a division of First Citizens Bank. With more than 1,500 bankers and relationship advisors and $44B in loans as of Q4 2025 – SVB delivers expert guidance, specialized products and a team that knows the innovation economy inside and out. Learn more at SVB.com.

Episode 445 of The VentureFizz Podcast features Roi Carmel, Co-Founder & CEO of Spotlight.ai. When the shift to AI happened, it created a market dynamic with three distinct types of software companies: 1. Ones that were already inmarket and suddenly found themselves in catch-up mode. 2. New startups built as AI native platforms right from the jump. 3. Companies that were already working on AI driven technology and had a massive head start, even if they weren’t using the term “AI” yet, but rather natural language processing, machine learning, or something comparable. Spotlight.ai fits squarely in that third bucket, having spent years building their platform. It was a problem that Roi experienced firsthand while in leadership roles at Cybereason and Perfecto Mobile. He saw that companies were struggling to operationalize their value proposition within the go-to-market team, making it extremely challenging to run an effective sales process. The team at Spotlight.ai spent two years interviewing over 50 CROs from top tech companies to understand their friction points and figure out how to solve the value-sales problem using NLP (natural language processing) or what the market now calls AI. Fast forward to today: Spotlight.ai is the deal-autopilot AI platform built on a proprietary sales knowledge graph with millions of correlated signals. It integrates across daily seller workflows to autonomously drive MEDDICC qualification (a sales methodology that originated at PTC). Other key benefits for their platform include fact-checking deal status based on hard evidence, auto-generating customer-facing assets, and delivering reliable, bottom-up forecasting. In this episode, we cover: * Roi’s thoughts on how established software companies should think about integrating meaningful AI features into their platform. * His background story including being a nationally ranked Judo competitor and how that helped to shape his entrepreneurial mindset. * A walk through his rapid rise to leadership roles across the tech industry. * The origin story of Spotlight.ai and how the platform works. * Why they chose to bootstrap the company and how they built a culture with zero turnover. * And so much more!

Episode 444 of The VentureFizz Podcast features Laura Rippy, Managing Partner and Board Member at Alumni Ventures. When you see the rankings of the top VC firms, you often hear the big brands out there like Andreessen Horowitz, General Catalyst, Sequoia, Accel, and others… but did you know that one of the top 20 VC firms, as determined by CB Insights, is based in Manchester, NH? Yes – Manchvegas, where I grew up, so I find that stat of particular interest. Founded in 2014, AV’s mission has always been to provide individual investors with professional-grade access to elite venture capital investing opportunities. It is a category that they pretty much created and it is not only working, but it is thriving. AV is continuously listed as one of the most active VC firms with thousands of investments made and over $1.6B in committed capital. Portfolio companies include Groq, the buzzing AI chip startup; Oura, the smart ring wearable company that recently filed for an IPO; Mercor, which was most recently valued at a decacorn status; and Apollo Atomics, a company that you might recognize, as I just had their CEO on The VentureFizz Podcast a few weeks ago. Laura comes to venture capital with a deep background as a former CEO and operator. In addition to serving on the board, Laura oversees multiple fund families at Alumni Ventures, including their Dartmouth fund called Green D Ventures, their Harvard fund called The Yard Ventures, their Women’s Fund, and US Strategic Tech Fund. In this episode, we cover: * Laura’s background as an operator and how she made the transition into venture capital. * The story and model behind AV, and how they built a $1.6B+ platform that democratizes VC access for accredited investors. * The current state of the markets in terms of trends in private vs. public markets, and high-profile portfolio stories like Oura and Northwood Space which is founded by Bridgit Mendler. * Deep dives into the various sectors that Laura concentrates on in terms of making investments. * How AV leverages its massive network and AI back office to add tangible value to its portfolio companies. * What she looks for in early-stage founders and the specific deal dynamics that signal a winning investment. * And so much more!

Episode 443 of The VentureFizz Podcast features Allison Byers, Founder & CEO of Scroobious. There is a lot that goes into raising venture capital. You have to have the right idea, market size, traction, and it’s incredibly helpful to be networked with VCs ahead of your fundraise. Plus, it’s very important that entrepreneurs are aligned with an investor’s expectations and motivations for funding a business because they are ultimately trying to provide returns for LPs. However, venture capital isn’t the only option for financing a company. There are lots of other avenues and some are non-dilutive like bootstrapping, revenue-based financing, traditional loans, and more. It was Allison’s own experience of leading a medical device company that was trying to raise its Series B round of funding after hitting every milestone, paying customers, and an FDA registration that opened her eyes to the challenges of raising capital. It led her to start a company and author a book to demystify the fundraising process and build a more equitable innovation economy. Through her company, Scroobious, she’s building a capital access platform where founders, investors, mentors, and advisors meet to build real relationships that unlock opportunity, innovation, and growth. Her recently published book, Fundraising for the Rest of Us, is a practical guide for raising capital on your own terms. In this episode, we cover: * Allison’s background growing up and how she got her career started. * Her personal story of being forced out of her job after returning from maternity leave, which ultimately led her down the entrepreneurial path. * The story of Digital Cognition Technologies, a neurodiagnostics product, and its attempted Series B fundraise and ultimate asset sale. * The inspiration behind Scroobious and how its platform helps founders. * The details of the Core 10 Pitch Deck Framework. * Her experience writing the book and what it was like recording the audiobook. * And so much more! Podcast Sponsor: This podcast is brought to you by one of the strongest longtime supporters of the local startup ecosystem, Silicon Valley Bank, a division of First Citizens Bank. With more than 1,500 bankers and relationship advisors and $44B in loans as of Q4 2025 – SVB delivers expert guidance, specialized products and a team that knows the innovation economy inside and out. Learn more at SVB.com.