The VentureFizz Podcast

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.

Episode 442 of The VentureFizz Podcast and today’s guest is Tess Michaels, CEO & Founder of Clasp.

When you look at several positions across the healthcare industry, clinical education is a strict requirement for the job… unlike business, where higher education is an option.

Yet, the cost of that education creates a massive barrier for students, while healthcare employers struggle with open positions and a very high annual turnover rate. According to a recent survey by Clasp, 70% of surveyed clinicians were turning to sports betting platforms like Kalshi, DraftKings, and FanDuel just to cover tuition and living expenses.

It’s a mess.

The good news is that Tess, who grew up in a family of healthcare professionals, saw this problem and did what any great serial entrepreneur would do: she built a solution.

Clasp is taking a unique approach to this situation. Think of them as the ROTC for healthcare, where Clasp connects large healthcare employers with clinical talent early while they are still in school. Employers commit to student loan repayment, and students commit to a multi-year retention period.

Clasp is one of those businesses that just makes sense, creating a win-win-win situation for students, schools, and employers alike.

The company recently announced a $20 million Series B round of funding to help accelerate the growth of its business.

In this episode, we cover:

* Tess’s background story and what helped shape her “non-quitting spirit.”

* What led her down the entrepreneurial path to starting a company while at Penn Wharton which was acquired.

* The foundational years she spent in investment banking and private equity.

* The inspiration behind Clasp and how its business model works.

* Details on their round of funding and how founders should conduct reference checks on investors.

* The story of landing the single-word domain, Clasp.com.

* Her biggest lessons learned while building Clasp.

* How she is using AI and detailed playbooks to prepare for maternity leave.

* And more!

Episode 441 of The VentureFizz Podcast features Assil Halimi, CEO & Co-Founder of Apollo Atomics.

Today we are diving into a topic that is way outside my typical comfort zone: nuclear energy. While fossil fuels still account for roughly 85% of global energy, nuclear power offers incredible energy density, yet conventional reactors take over a decade and billions to build.

Apollo Atomics is changing that. Through his research at MIT, Assil realized that existing designs for nuclear haven’t evolved in decades and he set out to change that with a breakthrough approach.

Apollo Atomics is an advanced reactor company developing compact pressurized water reactors designed to accelerate nuclear deployment. The company’s core breakthrough is a proprietary compact steam supply system that delivers approximately an order of magnitude higher power density than conventional designs, allowing Apollo to dramatically shrink the reactor while maintaining the same power output.

The key benefits for all of this is time and money. The resulting reactor platforms are designed to be factory built, transported by truck, and deployed in less than two years using commercially available fuel, established supply chains, and existing regulatory pathways.

The company recently announced an oversubscribed $31 million seed round of funding led by FCVC, with participation from Y Combinator, Alumni Ventures, Robinhood Ventures, and notable angels including Paul Graham.

In this episode, we cover:

* Advice on how to shift from academic research to an entrepreneurial mindset, plus advice on pitching Hardtech startups.

* Assil’s background story and how his interest in nuclear power originated.

* His time as an MIT Research Scientist and his process for working on this problem.

* How he met his co-founder, Drew Walker, and the origin story of Apollo Atomics.

* The breakthrough moment and all the details on how their technology works.

* Why nuclear is the safest way of making electricity.

* Their experience at Y Combinator, including a funny story about smoke in the parking lot.

* And, so much more!

Episode 440 of The VentureFizz Podcast features Eran Egozy, Professor at MIT and Co-Founder & CTO of Harmonix, the creators of Guitar Hero and Rock Band.

I love interviewing current entrepreneurs who are making waves in the platform shift to AI, but I am also a Boston tech historian with a passion for telling stories about the great tech companies of our past. And do I have an incredible one for you today.

Harmonix was a company that became a true cultural phenomenon in the late 2000s. It was an overnight success… well, not really overnight, but rather a 10-year journey of grit and iteration that resulted in video game franchises generating over $1B in revenue with more than 35 million units sold.

As you'll tell, I majorly geeked out on this interview. I am not a big gamer, but Harmonix hit massive product-market fit for me: music, gaming, rock star... sign me up! The song selection also struck a chord (pun intended), as it was pure gold.

You’ll notice this episode is longer than my typical interview. I went long form because there were just too many amazing stories to tell, including:

* Eran’s background story and how he got his start playing the clarinet.

* Studying music and engineering at MIT.

* Meeting his co-founder, Alex Rigopulos, and how they landed Brad Feld as an early investor.

* The seven game iterations with modest success that eventually led to massive PMF with Guitar Hero proving the 8th time’s the charm!

* Blowing up and taking the market by storm, leading to their acquisition by MTV Games.

* Launching Rock Band with multiple instruments plus the behind-the-scenes story of The Beatles edition.

* His current role at MIT as Professor of the Practice in Music Technology.

* And, so much more!

Episode 440 of The VentureFizz Podcast features Eran Egozy, Professor at MIT and Co-Founder & CTO of Harmonix, the creators of Guitar Hero and Rock Band.

I love interviewing current entrepreneurs who are making waves in the platform shift to AI, but I am also a Boston tech historian with a passion for telling stories about the great tech companies of our past. And do I have an incredible one for you today.

Harmonix was a company that became a true cultural phenomenon in the late 2000s. It was an overnight success… well, not really overnight, but rather a 10-year journey of grit and iteration that resulted in video game franchises generating over $1B in revenue with more than 35 million units sold.

As you'll tell, I majorly geeked out on this interview. I am not a big gamer, but Harmonix hit massive product-market fit for me: music, gaming, rock star... sign me up! The song selection also struck a chord (pun intended), as it was pure gold.

You’ll notice this episode is longer than my typical interview. I went long form because there were just too many amazing stories to tell, including:

* Eran’s background story and how he got his start playing the clarinet.

* Studying music and engineering at MIT.

* Meeting his co-founder, Alex Rigopulos, and how they landed Brad Feld as an early investor.

* The seven game iterations with modest success that eventually led to massive PMF with Guitar Hero proving the 8th time’s the charm!

* Blowing up and taking the market by storm, leading to their acquisition by MTV Games.

* Launching Rock Band with multiple instruments plus the behind-the-scenes story of The Beatles edition.

* His current role at MIT as Professor of the Practice in Music Technology.

* And, so much more!

Episode 439 of The VentureFizz Podcast features Ben Katz, CEO & Co-Founder of HYBRD.

Did you know that Y Combinator originated right here in Boston back in 2005? It was a legendary cohort with names like Sam Altman, Alexis Ohanian (yes, Reddit started in Boston), and Justin Kan all working on startups in Cambridge for the summer.

While the accelerator decided to keep the program exclusive to Silicon Valley long ago, Ben Katz and his team at HYBRD are proving that Boston founders can still break through YC’s ultra-competitive admissions process and leverage that momentum, learnings, and network to build a high-growth startup in Boston.

Ben is a WHOOP alum and a lifelong athlete who realized that existing fitness apps were limited and didn’t tell the full picture. To solve this, he co-founded HYBRD, an AI-powered fitness coach that integrates with your wearable devices and apps like Apple, WHOOP, Garmin, and many others. It takes the data from all these sources to create personalized, adaptive training plans that automatically adjust around your life, recovery, and daily schedule.

In this episode, we cover:

00:00 Introduction to Ben Katz and HYBRD

03:35 Quick Details on HYBRD

04:43 Applying and Getting into Y Combinator

09:25 What the YC Experience Was Like

11:47 Ben's Background & Early Career

16:54 Working at WHOOP

17:45 Building Fitness Apps at Appex

20:22 The Founding Story of HYBRD

24:28 How HYBRD is Different in the Fitness Category

26:56 Boston's Fitness Tech Ecosystem

28:45 All the Details about HYBRD & How it Works

33:28 HYBRD's Acquisition Strategy

37:05 HYBRD Funding Details

38:07 Details on the HYBRD Team

38:47 Advice for Building a Consumer Company

39:45 What Makes a Great Product Manager

40:47 The Importance of Building a Personal Brand & Voice

44:09 Ben's LinkedIn Strategy

44:45 Building in Boston vs. San Francisco

47:42 Favorite Apps and Recommendations

48:32 Book / Podcast Recommendations

50:26 Hobbies Outside of Work