The VentureFizz Podcast

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

Episode 417 of The VentureFizz Podcast features Rob Hughes, Co-Founder of Koo Capital.

If you haven’t met Rob yet… you should. He is one of the personalities behind the Boston tech scene and he is doing his part to bring the extra energy and buzz that is brewing in addition to initiatives like the Massachusetts AI Coalition.

We need more Rob’s, as he has a big personality and it’s only fitting that he is one of the faces behind Pitch Lift, along with angel investor, Steve Walsh. Pitch Lift is a Shark Tank style elevator pitch event that literally happens in an elevator. Founders get 30 seconds to grab the attention of an investor and make an impression before the doors open. It’s a fun but high pressure environment and you can see it in action on Instagram and TikTok.

In addition to Pitch Lift, Rob is a co-founder of Koo Capital, a private credit advisory platform built by bankers for founders to help high-growth companies unlock non-dilutive capital to scale faster.

In this episode of our podcast, we cover:

00:00 Introduction

02:05 Details on Pitch Lift & How it Got Started

07:20 How Pitch Lift Creates Social Content

09:26 Common Pitch Mistakes & Advice

11:59 Rob's Background & Early Career

18:13 Pivoting from Sales to Banking

22:27 Early Focus Servicing AI and ML Companies

24:45 Transition to Citizens Private Bank

29:00 Starting Koo Capital

30:58 His New Year's Resolution to Minimize Regret

31:58 Details on Koo Capital

33:24 Alternative Funding Advice for Entrepreneurs

36:17 What qualifications does Koo Capital look for?

38:24 Lessons Learned from Running his own Company

41:29 Reviving the Boston Tech Ecosystem

45:40 3 Essential Apps

46:43 Details on an Instagram Trail Reel

48:38 The importance of short video

49:50 Podcast & Book Recommendations for Entrepreneurs

50:54 Rob's other passions and hobbies

Episode 416 of The VentureFizz Podcast features Colin Raney, Co-Founder & CEO of Ray.

Here’s a "did you know - fun fact” for you. Studies show that 90 minutes of strength training a week adds four years to your lifespan! Who knew??? At least I didn’t, until I was doing research for this podcast.

I have to admit, I have a pretty good workout routine while I’m home between cardio and lifting dumbbells, but when I’m traveling… forget about it. For whatever reason, I just have a mental block where I’m just not motivated to work out.

This is just one of the many great use cases for how Ray helps. It is an AI native fitness app that behaves more like a personal trainer as it changes and adapts based on what the consumer needs by continuously learning from your feedback, preferences, and performance.

Ray’s co-founders are Colin and Rich Miner, who is a serial entrepreneur, investor, and co-founder of the Android operating system. The company is backed by Founder Collective, True Ventures, and other angel investors.

In this episode of our podcast, we cover:

* Colin’s background story growing up in Texas and how he got his career started in software engineering and then product management.

* Going back to business school at Carnegie Mellon and how he fell in love with design.

* How he landed at IDEO and later ran the firm’s Cambridge studio.

* Joining Formlabs as CMO in the early days of the company and the story of the launch of the Form 2 printer.

* Meeting TJ Parker and Elliot Cohen, the founders of PillPack and later joining as the company’s CMO… plus the full story to their acquisition by Amazon for a reported $1B.

* All the details about Ray and a demo of the product.

* His thoughts around branding and consumer marketing in the era of AI.

* And so much more!

Episode 415 of The VentureFizz #podcast features Parker McKee, Partner at Pillar.

“When you work really hard… good things come out on the other side.” - Parker McKee.

Parker is a perfect example of this mindset - a mantra that I firmly believe in. When Parker has a goal in his sights, he’s going to put in the time to get there. He’s proven this time and time again, and the results speak for themselves. In athletics, he spent countless hours in his parents' backyard honing his lacrosse skills, which ultimately led him to the D1 level at the University of Michigan, where he served as a co-captain.

Professionally, once he discovered a passion for investing and startups, he set his sights on venture capital. Through relentless networking, he landed an internship at .406 Ventures. Later, after pitching his own startup idea to Jamie Goldstein, he stayed on the radar and eventually joined the team in the early days of Pillar, where he has risen to the role as a Partner in the firm.

Pillar is a pre-seed and seed-stage VC firm that invests in technical breakthroughs to overcome the world’s greatest challenges. Last year, the firm announced their latest fund that being a $175M Fund IV.

In this episode of our podcast, we cover:

* The current state of venture investing in the AI era.

* Parker’s background and what playing D1 lacrosse at Michigan taught him about the rewards of hard work.

* How he broke into the industry with an internship at .406 Ventures.

* The story of how he pitched an app idea to Jamie Goldstein while still in college, and how that relationship eventually led to his role at Pillar.

* An inside look at a "junior-level" role in venture capital and how he learned the ropes by simply "being in the market."

* His current investment focus and the details behind his investment in OpenHands, alongside Menlo Ventures.

* What he expects out of a first meeting and his best advice for a successful pitch.

* The biggest lesson he’s learned so far in the world of venture capital.

* 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.

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

Episode 412 of The VentureFizz Podcast features Nick Leonard, CEO & Co-Founder of VoiceRun.

Is voice finally having its moment? For years, it felt like the "promised land" that never quite arrived. But things are different in 2026, in many ways, and from what I’ve noticed is a shift in consumer behavior where voice is becoming the primary interface.  Maybe it’s because the technology is so much better for basic commands like speech-to-text, but the next wave of voice AI startups are looking to completely revolutionize the game with agentic voice AI systems that don’t just talk, but listen, reason, and take action in real-time.

Voice is hard, though. A lot goes into building a platform that truly does voice right and if you don’t get it right, whatever app or platform you are building will fail. That’s exactly the gap that Nick and his team are bridging.

VoiceRun is a developer-first platform for enterprise voice agents. Unlike the low-code, visual tools that often break under the weight of complex business logic, VoiceRun offers a code-first "Foundry" that gives developers the control they need to build secure, reliable, and scalable voice infrastructure. The company recently announced a $5.5M seed round led by Flybridge, with participation from RRE Ventures and Link Ventures.

In this episode of our podcast, we cover:

* Nick’s perspective on the strategic decision for AI startups to build broad platforms versus niche industry solutions.

* His journey from Muncie, Indiana, to being a track athlete at MIT and competing in the decathlon.

* Getting his start working on F-135 Joint Strike Fighters at Pratt & Whitney, and the lessons learned from his previous startup and leadership roles at Jobcase and Posh Technologies.

* The background story of how he and co-founder Derek Caneja landed on a developer-first platform for building enterprise voice agents.

* Why they intentionally chose not to put "AI" in the company name or branding.

* What truly makes a great Product Manager

* And so much more!

Episode 411 of The VentureFizz Podcast features Madeleine Smith, CEO & Co-Founder of Civic Roundtable.

We all know that building a startup is incredibly hard. But building a startup for the government sector? Many would say that’s insanely hard. The reputation of slow-moving bureaucracies, limited budgets, and legacy tech is enough to scare off most founders.

However, where others see obstacles, entrepreneurs like Madeleine see a massive, untapped opportunity. True disruption often comes from those who come into the equation with a fresh look and a different perspective.  The result, an underserved industry that is hungry for modern tools to help them with their day to day workload.

That is the origin of Civic Roundtable, a government operations platform purpose-built for federal, state, and local agencies. Emerging from the Harvard Innovation Labs, the company is already trusted by public servants at over 1,500 agencies across all 50 states. With funding led by General Catalyst, they are modernizing how millions of government workers across 90,000 agencies collaborate and achieve their mission.

Chapters:

00:00 Intro

02:17 How Entrepreneurs Should Think About Adding AI Into Their Platform

04:37 Madeleine's Background & Early Career

05:24 Working at Mark43

07:38 Transitioning to Product Management

09:47 The Journey to Civic Roundtable

12:03 Customer Discovery and Validation

14:49 Initial Proof of Concept

17:04 Building the Government Operations Platform

20:14 Creating a Successful Company in the Government Sector

22:01 Achieving Compliance and Security Standards

23:25 The Benefits of Working with Past Colleagues

24:42 Funding Details from General Catalyst

25:42 The Latest at Civic Roundtable

26:47 Sales Strategy and Market Positioning

28:32 Fast Company Recognition

29:12 Looking Ahead

30:25 Advice for First-Time Founders as CEO

31:31 Building a Company as Non-Technical Founders

33:29 Advice & Encouragement for Female Founders

34:54 Involvement in Charitable Organizations

37:24 Personal Interests and Hobbies

Episode 410 of The VentureFizz Podcast features Paul Holder, CEO & Co-Founder of OnRamp.us.

I’ve been working with startups since 1998—that’s nearly 28 years now! Since the beginning, I’ve noticed the massive impact that startups can have on one's career.

Take Paul… who joined an early-stage startup called Troops, which was later acquired by Salesforce. During his tenure there and at a software company prior (VTS), he didn't just experience the rocket-ship growth and accelerated career path that comes along with a successful startup—he also identified the massive challenge that led to OnRamp. It’s a challenge that faces every company, not just software companies: Customer Onboarding.

Founded in 2020, OnRamp is the intelligent, AI-enabled customer onboarding and engagement platform that helps companies accelerate adoption, strengthen customer relationships, and unlock revenue growth. The company recently announced its $15M Series A round of funding led by Koch Disruptive Technologies, with contributions from existing investors like Contour, Javelin, Pear, and others.

In this episode of our podcast, we cover:

* Advice on taking the entrepreneurial "leap of faith" and why you have to commit to a decade-long vision to build something meaningful.

* Paul’s background studying Finance at Boston College and his early career in strategy consulting.

* His time at HighTower (where he met his co-founder Ross Lerner) and leading customer success and post-sales revenue at Troops.

* How the friction of onboarding customers led to the original idea behind OnRamp.

* Building their first version using Bubble (a no-code solution) long before "Vibe Coding" became a buzzword, and how they landed those crucial early adopters.

* How OnRamp stays disciplined with their product roadmap while integrating AI to solve real-world customer pain points.

* How they’ve successfully moved upmarket to land some of the world's largest companies and their philosophy on hiring the first sales leader.

* And so much more!

Episode 409 of The VentureFizz Podcast features Ilia Papas, serial entrepreneur and co-founder of Band and Blue Apron.

Do you know what the enchilada factor is? Probably not… unless you were part of the Blue Apron team that created a national brand and one of the pillar companies in the meal-kit food delivery category that ultimately went public.

In this interview, Ilia shares the inside look at those hypergrowth years, including the company’s use of machine learning for planning labor and food ordering, so they could fulfill those enchilada orders (also known internally as the enchilada factor) which always caused a spike when it was offered on the menu.

Ilia’s latest company is Band—and no, it’s not the musical kind. Instead, the company is focused on a massive, underserved sector where trillions of dollars flow between businesses, yet technical innovation has been severely lacking. Band has built the smart operating system for B2B trade agreements, providing AI-powered rebate and incentive tracking for distributors, manufacturers, and purchasing groups.

In this episode of our podcast, we cover:

* Ilia’s background story, plus the details on his siblings and their collective success in the tech industry.

* Interning at his brother Art’s company, Bullhorn, and then building the foundation of his career at web consulting firms like Molecular and Optaros, where he worked on the original version of Rue La La.

* How he met his co-founder, Matt Salzburg, and why they pivoted from a “Kickstarter for science” idea to food delivery in 2012.

* Bringing on a third co-founder, Matt Wadiak, who brought the culinary expertise and why they names the company Blue Apron.

* Their approach to growth marketing to compete against HelloFresh & Plated and scaling to millions of meals a week.

* The story of the IPO in 2017 and the unique challenges of running a publicly traded company

* All the details about Band and why Ilia chose this underserved industry, plus how his approach to building a company is different this time around.

* And so much more!