Episode 355 of The VentureFizz Podcast features Ben Maitland-Lewis, Director of Startup Banking & Founder Success at Silicon Valley Bank (SVB) and yes, this episode is also sponsored by SVB.

Ben and I go way back. His previous company, Pretty Instant, had a long-standing relationship with VentureFizz. This Y-Combinator company was an on-demand photography marketplace that did all of our office tour photoshoots on VentureFizz. It honestly was an amazing experience… such a great company.

But even when you work with someone for a long time and you have a great professional relationship, there is so much about the person that you don’t know and this is one of the reasons why I love this podcast.

I learned that Ben’s background story is very eclectic… from living abroad as a child, to being a street performer and being in the circus to playing music with an orchestra… and then being in a band playing the top clubs in LA to playing drums for other bands like Incubus, Dishwalla, and others… I could go on and on, so I’ll stop here and let him tell his story in this interview.

Today, Ben is still leveraging his experience as a founder but helping other entrepreneurs in lots of meaningful ways at SVB.

In addition to Ben’s background story, we also cover:

* A discussion about making the transition from founder to employee.

* Ben’s journey into entrepreneurship and the story of PressKit.

* All the details about Pretty Instant and how the company got started and scaled.

* His current role at SVB and the different ways he is working with founders.

* Some analysis and positive vibes from SVB’s State of the Markets report.

* And so much more.

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 354 of The VentureFizz Podcast features Paul Morville, Co-Founder & CEO of Parrot AI.

This episode was recorded live at Startup Boston Week at Suffolk University. I recorded two episodes at this year’s event, so stay tuned for the second episode in a couple of weeks.

Paul is a serial entrepreneur and as you’ll hear from our podcast, he is very successful but likes to fly under the radar. Case in point, while most companies can’t wait to broadcast a round of funding, I couldn’t find any press releases or media coverage about any outside investment for Parrot AI. Come to find out, the company raised capital in 2021 from Accomplice, Pillar, Legion Capital, and others. We discussed his reasoning as to why they decided against announcing funding which was very interesting.

Parrot AI is not just a meeting recorder, transcription, and note-taking tool. It is an AI-powered collaborative workspace that turns conversation into results because of its understanding of the full context of a business.

In this episode of our podcast, we cover:

* The 2 biggest lessons learned while building multiple companies.

* Paul’s background story and his work on building Barron’s online property which was one of the first financial websites.

* His professional journey as a Product Manager, including experience at Arbor Networks and how so many people have gone off to start other companies like Twilio.

* The founding story of Confer which was one of the first endpoint security solutions in the cloud that was acquired by Carbon Black which later went public & was acquired by VMware.

* His decision to pass on an opportunity to join a VC firm and continue down the entrepreneurial path.

* All the details about Parrot AI and how it differentiates itself from competitors.

* What makes a great Product Manager.

* And so much more.

Episode 353 of The VentureFizz Podcast features Giuseppe Stuto, Co-Founder & Managing Partner of 186 Ventures.

Did you know that the venture capital industry originated in Boston back in 1946 with the founding of American Research and Development Corporation (ARDC) which backed Digital Equipment Corporation and saw a 1200X return when the company went public.

Since then, Boston has been very fortunate to have a steady stream of VC investors at all stages to foster the local startup ecosystem and one of the newest firms is 186 Ventures.

Co-Founded by Giuseppe and Julian Fialkow, 186 Ventures is a pre-seed & seed stage VC firm investing broadly across technology. I kept hearing about the firm, so I was excited to interview Giuseppe for the podcast as they have been out there hustling and have been earning the respect from entrepreneurs and their peers in the VC industry.

In this episode of our podcast, we cover:

* A discussion around the importance of investor & founder alignment.

* How a conference at Stanford changed the trajectory of his career into entrepreneurship.

* The full background story of SmakHigh and how they evolved to Fam, the first live group video application for iMessage, including how Jeff Bussgang’s book - Mastering the VC Game - helped them raise venture funding from Jeff.

* The full story of how the acquisition by DraftKings came to fruition.

* The details about 186 Ventures and what they are targeting for investments.

* The 4 fundamental parts of a business that matter.

* The importance of building a repeatable sales model for not only your go-to-market strategy but also how it factors into raising capital.

* Why Boston is the best place to build an AI startup.

* And so much more.

Episode 352 of The VentureFizz Podcast features Mark Ghermezian and Manisha Shah, Founder of Tildei.

Mark is the Founder and General Partner of m]x[v Capital and he’s also the CEO of two companies that have spun out of his firm, that being Tildei and Gynger. Mark has been an entrepreneur pretty much his entire life and he shares lots of fun and interesting stories of these ventures, including the full story of Braze, a customer engagement platform that eventually went public in 2021.

Manisha is a Co-Founder and Chief Revenue Officer of Tildei. In this interview, she shares her professional journey into the tech industry and ultimately running customer success at Rebel which was acquired by Salesforce.

Tildei is changing how companies and customers communicate. The company’s AI-powered platform, which is initially focused on WhatsApp, enables brands to build deep relationships with customers through conversation at scale. The company has raised $6M in funding led by Susa Ventures with participation from Ludlow Ventures, Gradient Ventures, Lerer Hippeau, Vine Ventures, MXV Capital, Marcelo Claure, Jason Lemkin, and other angel investors.

In this episode of our podcast, we also cover:

* The importance of persistence and grit when building a startup.

* How Mark and Manisha came together to build Tildei and how it works.

* Building and investing into companies from m]x[v including the details on Gynger.

* Mark’s contrarian point of view of PLG sales models and why he favors a traditional outbound sales operation.

* Manisha’s biggest lessons learned as a co-founder.

* And so much more.

Episode 351 of The VentureFizz Podcast features Meredith McPherron, CEO & Managing Partner at Drive by DraftKings.

Legalized sports betting, NIL, transfer portals, college conference re-alignment, streaming, pitch clocks, new kickoffs, the explosion of pickelball, and so much more, there is no denying it, the sports industry is going through a rapid amount of transformation.

But the number one area that I’m the most excited about is the explosion of women’s sports… from college basketball, WNBA, NWSL, Olympic success, and more… there is so much going on!

Thus, I couldn’t pick a better person to have a conversation about how women’s sports are having a moment than with Meredith and this topic is exactly how we kick off our interview.

If you are not familiar with Drive by DraftKings, the firm invests in seed and Series A companies in the SportsTech and Entertainment industry specifically in Gaming, Fandom, and Human Performance.

In this episode of our podcast, we cover:

* Meredith’s background story including being a walk-on two sport Division 1 athlete at Harvard.

* Getting her career started in investment banking and consumer products at General Mills and how she made the switch to the tech industry.

* Running her own startup called Zipteva, which was early to market and would have been perfect in today’s world of NIL deals.

* Her role at The Arthur Rock Center for Entrepreneurship at HBS which was the segue into her role as a VC at Glasswing Ventures.

* All the details about Drive by DraftKings and what she is targeting for investments, plus its all-star network.

* Biggest challenges around building a startup in the sports industry.

* And so much more.

Episode 350 of The VentureFizz Podcast features Steve Papa, serial entrepreneur, mentor, and investor.

It is time for another milestone episode and I couldn’t be more excited about this interview.

Steve has accomplished so much throughout his career, so let’s just dive in. In this interview you are going to hear lots of amazing stories like:

* Steve’s background and how he got his career started in the tech industry, including his involvement in the early days of Akamai.

* The full lifecycle story of Endeca in terms of how the idea originated, to getting traction and raising funding, scaling, to a $1.1B exit to Oracle… plus so many amazing stories along the way.

* The Special Ops team at Endeca and how many of the members of this team have gone on to be founders & leaders of companies.

* Investing all of the money that he made from Endeca back into startups.

* The story of Toast and how its distribution channel innovation drove the company’s success and helped create the vertical SaaS category.

* The importance of Parallel Wireless and why it is such a passion project for him.

* The problem that Shoobx was solving for startups and its exit to Fidelity.

* How the tech industry repeats itself and his thoughts on AI.

* Plus so much more!

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 349 of The VentureFizz Podcast features Chris Gardner, Partner at Underscore VC.

One time, could be luck. Two times, ok… maybe you are on to something… but in the case of Chris, he has been part of several acquisitions, so there is something deeply there in terms of his ability to pick the right company to join or company to help co-found. There is no denying it, based on his track record as an operator, there is an obvious translation to his current position as a venture capitalist.

This episode is another fun walk down Boston tech memory lane, as we talk about some legendary companies that were acquired like edocs (an early e-billing and customer self-service applications), M-Qube (early mobile messaging and content services company), ExtendMedia (white label video platform), and Paydiant (an early mobile wallet tech company that powered payment apps for Subway, Harris Teeter supermarkets, Capital One, MCX, and many more).

What I also find really interesting is how Chris’ background spans across both product and marketing, where he led both entities at companies. Perhaps I’m wrong, but it is a skillset that I haven’t seen too often.

Chris is currently a Partner at Underscore, a firm that is investing in pre-Seed and Seed B2B software founders. The firm recently announced a new $58M Fund III.

In this episode of our podcast, we cover:

* Chris’ background story and how he got into the tech industry.

* The stories and his role in the companies previously mentioned including being a co-founder of Paydiant, their impact on mobile wallets, and the company’s acquisition by PayPal and what he learned there.

* How Chris became a VC and the details on what he is targeting in terms of investments at Underscore.

* Pitch advice for startups and the importance of storytelling.

* How you need to think about compensation structure as a company scales.

* And so much more.

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 348 of The VentureFizz Podcast, sponsored by Silicon Valley Bank, features Jonathan Bensamoun, Founder & CEO of Fi.

It’s crazy to think that The VentureFizz Podcast has been around since 2018 and I believe that I’ve only had one repeat guest and that founder was talking about a new company.

Thus, this is the first time I am doing a follow up episode and Jonathan was my guest for Episode 110 back in 2019.

I ran into Jonathan at the Lerer Hippeau summer party in NYC and as we were chatting about his business, it seemed very obvious that we needed to do a new interview.

What’s cool about this episode is the format, as it is different from most of my interviews. Since we already discussed his background story in the original episode, we were able to go deeper into Fi’s business and what has happened over the past 5 years.

If you are not familiar with Fi, they are the creators of the Fi Smart Dog Collar which not only has real-time location tracking, but the device also includes activity, sleep, and behavior monitoring.

In this episode of our podcast, we cover:

* A brief overview of Jonathan’s background story and what was the inspiration behind Fi.

* The latest about the Series 3 product line, plus a demo and all the cool features.

* The importance of sleep tracking for your dog and how the movement to health tracking is a key piece of Fi’s strategy.

* Lessons learned from retail and why a straight direct-to-consumer model is the right fit for them at this point in time.

* Building out a company’s leadership team and Board of Directors.

* What the fundraising process has looked like through Fi’s journey.

* Creating a category and why more competition in the industry would be a good thing.

* And so much more.

More about our 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 347 of The VentureFizz Podcast features Joe Caruso, Investor & Mentor.

Lots of people know of Joe as an angel investor, but when I think of Joe… I think of a mentor to so many entrepreneurs and a major supporter of the Boston startup ecosystem.

If you go through Joe’s portfolio of investments from his Bantam Group website, it will give a strong perspective to the depth of his connection to the Boston tech scene.

This podcast interview is a bit different. We start off by talking about his role as a mentor and during that conversation, we weave in his background like leaving high school before getting his diploma and enrolling into Northeastern. He shares lots of great advice throughout the conversation.

What I found to be incredibly fun was the talk down memory lane and getting to hear the inside story of some of his investments in companies like HubSpot, Constant Contact, Carbonite, and LevelUp, plus the missed opportunity with DraftKings.

And one of my favorite stories actually has nothing to do with tech… he was on the board of the company that invented the Frappuccino. Oh, you think that was Starbucks? You’ll have to listen to find out…

Episode 346 of The VentureFizz Podcast features Scott Weller, CTO & Co-Founder at EnFi.

The formula for a thriving tech ecosystem ideally looks something like this:

* Entrepreneurial-minded person works for startups and learns a ton. Perhaps they even witness success at scale to an exit.

* Said person takes lessons learned and builds their own company to an exit.

* Said person then starts to mentor and invest back into the ecosystem to fund the next generation of companies.

* Said person eventually finds an idea that they can’t get out of their head and launches another company.

This is the case for Scott, as he was involved in tech from an early age and connected with a talented group of entrepreneurs who were building the first generation of online gaming where he witnessed a couple of exits.

He then co-founded and was the CTO of SessionM which led to a successful exit to Mastercard. He was angel investing and advising companies when he and another successful entrepreneur, Josh Summers, saw a problem which was a perfect opportunity to disrupt an industry using AI.

Josh has the same startup founder pedigree as he was part of the WHERE team that was acquired by PayPal and then went on to found Clypd which was acquired by Xandr.

The two have come together to build a company called EnFi which recently announced $7.5M in seed funding led by Unusual Ventures with participation from Boston Seed, Argon Ventures and Impellent Ventures. EnFi is accelerating complex credit analysis and risk monitoring with AI Assistants for bank and private lending origination, underwriting, and portfolio management teams.

In this episode of our podcast, we cover:

* A discussion about the AI landscape in the Boston tech scene.

* Scott's background story and his early involvement with one of the very first Internet Service Providers called Intelecom Data Systems as a teenager.

* Working at an early stage web gaming startup called Gamesville which was acquired by Lycos.

* GameLogic and the early innovation of working with regulated games and the level of innovation in terms of patent creation which was acquired by Scientific Games.

* Being early to market with an online video product for SMBs called SnapYap that he started with others.

* The founding story of SessionM with Mark Hermann & Lars Albright and how the company evolved through the years, plus its acquisition by Mastercard and how things materialized post-acquisition.

* SessionM’s involvement in building the very successful mobile app for Starbucks and its bonus & loyalty campaigns.

* The background story and all the details about EnFi and how they are disrupting the market.

* Common startup mistakes that he sees entrepreneurs make over and over again.

* And so much more.