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!

Episode 408 of The VentureFizz Podcast features Matt Fates, Partner at Innospark Ventures.

Did you know that the first modern venture capital firm was started right here in the Boston area? It’s true. Back in 1946, Georges Doriot founded the American Research and Development Corporation (ARDC), marking the birth of an industry that has fueled the entrepreneurial dream for nearly 80 years.

Matt Fates entered the industry during the “Internet 1.0” era, a time when VC firms were just beginning to gain major visibility. Over the course of his career, he has invested in over 100 companies. Through those investments, he has developed a deep expertise in data-driven enterprise and infrastructure startups—experience that has perfectly positioned him for the current massive shift toward AI.

Innospark Ventures is an early-stage venture capital firm that invests in AI-native companies solving previously intractable problems across healthcare, life sciences, and the enterprise.

In this episode of our podcast, we cover:

00:00 Intro

02:22 VentureFizz OG

03:42 How to Land a Job in Venture Capital

07:49 Matt's Background

13:05 Getting into Investment Banking in the Tech Industry

16:22 Transition to Venture Capital

21:07 Dartmouth MBA

24:05 Experience at Ascent Venture Partners

28:59 Details of Innospark

30:39 Foundational Knowledge in AI and Machine Learning

32:41 Area of Focus for Investments at Innospark

37:04 Recent Investments for Innospark

43:36 The State of the Boston Startup Scene

46:51 The Anti-Portfolio - Missed Investments

49:04 Rapid Fire Questions

50:09 Personal Interests

Episode Sponsor: As a longtime champion of the local startup ecosystem, Silicon Valley Bank supports innovative companies with the solutions and financing they need through every stage of growth. With more than 1,500 bankers and relationship advisors, and $42B in loans as of Q2 2024 – SVB delivers the right people, service and resources to support your entire financial journey. Learn more at SVB.com.

Episode 407 of The VentureFizz Podcast features Seth Rosen, Founder & CEO of CustomMade.

A common theme that you’ll hear throughout this interview is the importance of resiliency.

Sure - the media loves the story of the latest company that has achieved $100M ARR in a month (I’m obviously kidding), but the overwhelming majority of businesses are a grind. It’s about taking a bunch of punches, getting back up and figuring it all out.

It’s not all rainbows and butterflies, which is why I was excited to interview Seth. The story of CustomMade has lots of twists and turns… from rapid growth… to later salvaging the company by structuring a deal with Wayfair to acqui-hire their employee base… to the insanely successful reboot!

Today, CustomMade is a leading online custom jeweler that specializes in creating personalized, one-of-a-kind jewelry pieces, such as engagement rings, wedding bands, and more. The platform simplifies the entire custom process, helping buyers create their vision and working with master jewelers to bring it to life.

Chapters:

00:00 Intro

00:11 Importance of Resiliency

01:20 The Right Business Model: Subscription vs Marketplace

02:52 Seth's Background

06:24 Meeting Mike Salguero While Working in Real Estate

12:51 Background Story of CustomMade

20:55 Raising Venture Capital for CustomMade

24:58 Building & Running an Online Marketplace

27:30 The Challenges of Running an Online Marketplace

29:24 Making a Deal with Wayfair

31:33 CustomMade Reboot

36:38 CustomMade Today - The World's Largest Online Custom Jeweler

40:10 What are Lab Grown Diamonds

44:24 SEO & GEO

49:20 Seth's Other Initiatives in the Gem Industry

50:46 Seth's Role as a Venture Partner at WTI

Episode 406 of The VentureFizz Podcast features Bill Simmons, serial entrepreneur and Co-Founder of Orbit.me and DataXu.

I’m going to use the cliché: Bill actually is a rocket scientist. His background is in aerospace engineering, he holds a PhD from MIT, and he worked on 13 space missions. In addition, he was part of a major Government competition for simulating options for space travel to Mars. His team simulated 35 billion possible options to generate 1,100 different Mars missions that were all feasible.

This groundbreaking technology that leverage Big Data, which we now recognize as AI and machine learning, launched his first company, DataXu, in 2008. DataXu became a pioneer in the programmatic ad platform category and raised over $87M in funding. The company scaled as a major player in the Boston tech scene, and was acquired by Roku in 2019.

Now, Bill is tackling a challenge we all likely face with his new startup, Orbit.me. Information is scattered across texts, multiple email inboxes, LinkedIn, WhatsApp, and social apps—it’s impossible to keep track of what matters. Orbit.me is a perfect use case for AI, organizing your scattered messages into “Orbits” which are dedicated spaces built around the real contexts of your life, like parenting, work, or other important matters.

Chapters:

00:00 Introduction

02:41 Current Status of Space Travel & Mars

08:34 Bill Simmons Background Story

10:21 Academic Experience

13:12 Space Missions including Mars Research

17:19 How DataXu Came to Fruition & Focus on AdTech

20:03 Scaling DataXu & Market Strategies

23:15 The Competitive Landscape of AdTech

26:20 The Technology Behind Real-Time Bidding

29:49 Building DataXu’s Culture During Growth

32:51 DataXu Acquisition by Roku

35:54 The Transition to Product Management & Experience at The Trade Desk

37:13 The Details of Orbit.me

43:07 The Team Behind Orbit.me

48:58 The Evolving Role of Software Engineers in the AI Era

52:01 Lightening Round Questions

Episode 405 of The VentureFizz Podcast features Ed Jennings, CEO of Quickbase.

The terms 'narrow' and 'growth' seem to contradict each other, yet in Ed’s mind, the two concepts go hand-in-hand. Based on his experience, true scaling doesn't always mean adding new products or wildly expanding into new industries.

It can be a huge challenge to say "no" to new opportunities when the goal is increased revenue. But as Ed explains, the key to sustainable success is to look deeply at your core customer and double down on your core value. This focus is what helps you win and retain customers—a factor often overlooked, but insanely important for long-term growth.

Quickbase is the AI operations platform used by more than 12,000 organizations worldwide to transform ordinary work into extraordinary impact. Combining powerful AI capabilities and the flexibility and ease of low code/no code technology, Quickbase boosts productivity, improves efficiency, and enhances employee safety for organizations managing large-scale projects and operations in industries like construction and manufacturing.

Chapters

00:00 Introduction

02:00 Core Foundational Elements for Scaling Companies

06:21 Ed's Background Story & Post College in Japan

13:01 Career & Executive Roles in Tech

15:26 Experience at PTC

18:04 First CEO Role

21:55 Time at ADP

24:44 Experience at Veracode

28:22 Lessons Learned as CMO

30:13 COO Role at Mimecast

35:55 Details About Quickbase

36:56 Narrowing the Focus and ICP at Quickbase

39:09 The Culture at Quickbase

41:00 Hiring at Quickbase

42:44 Quickbase's Customer Community

44:23 Advice for Building a Career Path to CEO

46:56 Advice on Hiring Executives

49:51 Lightning Round Questions