The VentureFizz Podcast

David Fialkow, co-founder and managing director of General Catalyst, is an entrepreneur, investor, philanthropist, and Oscar-winning documentary producer. He discusses how storytelling from filmmaking helps founders, Boston’s entrepreneurial culture, building a travel empire with long-term partners, launching General Catalyst during the post-dotcom winter, and the firm’s founder-focused, intergenerational approach to investing.

A wide-ranging conversation about building a coastal VC presence and how a west-coast firm expands to Boston. Stories about founding and exiting a company and lessons learned along the way. Practical networking tactics and a look inside a selective pre-seed accelerator program. Reflections on the Boston tech scene and career pivots from finance to startups.

Megan Lanham, CEO and co-founder of Rithmm and former Division I basketball coach turned life sciences CEO. She discusses the surge in sports betting, how predictive models and AI power Rithmm, building product features like model-building and line shopping, user acquisition strategies, and advice for women founders. Short, energetic conversation about tech, analytics, and scaling a startup.

Chip Hazard, General Partner at Flybridge and longtime investor behind MongoDB, shares wild anecdotes like being linked to a Small Soldiers character. He traces platform shifts from internet to cloud to AI. Short, punchy stories cover Flybridge’s early applied-AI thesis, longform blogging, seed-stage investing, and building big tech outside Silicon Valley.

Episode 418 of The VentureFizz Podcast features Jeff Glass, Co-Founder & CEO of Hometap. Jeff’s track record is pretty amazing, yet he is incredibly humble. As both an entrepreneur and an investor, he has…in my opinion… earned a spot as one of the top builders in the Boston tech ecosystem. While success always requires the right market timing and a great team, you also need a leader who truly thrives in the full lifecycle journey of building a startup and that is exactly what Jeff has done throughout his career. Listen to this track record. Back in the Internet 1.0 era, he co-founded Transactive Solutions. This tech company included a web property called Zooba which scaled and had very forward looking technology. The company was acquired by a joint venture between Bertelsmann and AOL Time Warner. Then, in the early days of mobile, he led m-Qube through each company phase from figuring out product market fit to the hypergrowth years and eventually an acquisition by VeriSign. Beyond the exit, m-Qube is legendary for its "alumni network," having produced a generation of founders and executives who have gone on to build many successful companies in Boston and beyond. Jeff also spent years as a VC with Bain Capital Ventures, where he sat on the board of LinkedIn for three years leading up to their IPO. He later joined a portfolio company as the CEO of Skyhook Wireless which was acquired by Liberty Media. Today, Jeff is the CEO and Co-Founder of Hometap which has a very meaningful mission: making homeownership less stressful and more accessible. Hometap allows consumers to access the equity in their homes without taking on a loan or sell their home. Think of it like a startup, where an investor is taking equity as a percentage of ownership in a company for a future return. The same idea applies here for consumers and their home. It’s just one of those ideas that makes a world of sense. Chapters: 00:00 Introduction 03:40 Building Extraordinary Teams 07:38 Jeff's Background & Early Career 15:15 Learning How to Sell 23:27 Early Career 28:30 Building Zooba to an Exit 39:49 m-Qube and the early days of mobile 44:33 Powering the Voting System in American Idol and Deal or No Deal 47:15 VeriSign's Acquisition of m-Qube 50:41 The amazing alumni of m-Qube 54:27 Joining Bain Capital Ventures 58:30 Joining Skyhook Wireless as CEO 01:01:15 The Early Beginnings of Hometap: A New Approach to Home Equity 01:06:28 Building Hometap: Raising Capital and Growing Initial Customer Base 01:12:43 The Scale of Hometap 01:16:08 How Hometap Works 01:20:17 What's Next for Hometap? 01:22:09 Jeff's Interests Outside of Work

Rob Hughes, co-founder of Koo Capital and co-creator of Pitch Lift, is a Boston connector who helps founders access non-dilutive private credit and creates viral founder content. He discusses how Pitch Lift was born and turned into short-form social media, common pitch mistakes and fixes, building Koo Capital to match lenders with startups, and reviving Boston’s tech scene.

Colin Raney, Co-founder and CEO of Ray, is a designer-turned-founder who led marketing at PillPack and Formlabs. He discusses building Ray, an AI-native personal trainer that adapts to your feedback. Short segments cover Ray’s demo, tech choices like computer vision, retention and acquisition strategies, and how branding and creators fit into an AI fitness product.

Parker McKee, Partner at Pillar and former D1 lacrosse co-captain, rose from internship to lead early-stage bets on technical breakthroughs. He discusses AI’s impact on venture, how athletic grit shaped his path, pitching and sourcing deals, and the story behind investing in OpenHands. Quick, candid takes on what early VC work actually looks like.

Episode 414 of The VentureFizz Podcast features Lou Shipley, CEO, board director, lecturer, investor, and now author. Every company has an entrepreneur behind it. It sounds obvious, but we often fall into the trap of thinking those founders are all 20-somethings building tech startups. The data says otherwise. Research from MIT Sloan found that the average age of a successful, high-growth founder is actually 45 years old. For most, it takes decades of “real-world” reps to build the grit and experience necessary to take that leap of faith. That’s why Unlikely Entrepreneurs, the new book that Lou co-authored with Patricia Favreau is such an essential read. It includes local entrepreneurs like Bill Warner of Avid or the founders of Spoiler Alert, alongside truly unexpected success stories, ranging from a sustainable sausage brand and an online casket company to Katie Couric Media. In this episode, we cover: * What led Lou and Patricia down the path of writing Unlikely Entrepreneurs. * Lou’s background story and what athletics taught him about being a CEO. * How a cold call to Bill Warner, the founder of Avid, changed his career trajectory. * His journey through various leadership roles at startups like WebLine, Reflectent, and Turbonomic. * How he helped build Black Duck Software into a market leader by repositioning the product and the company’s culture. * The importance of teaching sales and his advice around building out your GTM function. * Why relationships are the ultimate form of currency for your success. * And so much more! Purchase Unlikely Entrepreneurs on Amazon: https://www.amazon.com/Unlikely-Entrepreneurs-Lou-Shipley/dp/1394345895/ref=sr_1_1 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 413 of The VentureFizz Podcast features Scott Savitz, Founder and Managing Partner of Data Point Capital and Founder & former CEO of Shoebuy.com which is now known as Shoes.com. In my opinion, Boston doesn’t give itself enough credit, especially when it comes to consumer brands. It’s the home to consumer icons like Bose, SharkNinja, Dunkin, TJX, and many more. But if you look at the footwear category, it is a powerhouse with leading brands like New Balance, Converse, Sperry, Keds, Rockport and next generation companies like NoBull, Oofos, and BRUNT. So, maybe it comes as no surprise that one of the first companies to sell footwear online was headquartered in Boston and yes, that is Shoebuy. This was back in 1999, when buying shoes online wasn’t a thing and even Zappos was just getting started. Thus, I was excited to break down this major eCommerce success story that completely disrupted an industry on so many different levels. Today, Scott is a Venture Capitalist and his firm, Data Point Capital, invests in revenue-stage technology companies across both B2B and B2C categories. The firm’s portfolio includes DraftKings, Rent The Runway, Resident, Black Kite, Jebbit, and others. In this interview, we cover: * Scott’s background story and early professional experience in the mortgage and banking industry. * What it was like building a company in the early days of eCommerce and ignoring the naysayers. * How Shoebuy won over the brands and the details about their - at the time - innovative virtual inventory model. * Strategies around customer acquisition combined with a focus on capital efficiency to scale the business. * The story of the acquisition to IAC. * What led Scott down the path of starting Data Point Capital and what they are targeting for investments. * And more