The VentureFizz Podcast

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

Episode 404 of The VentureFizz Podcast features Ben Sesser, CEO & Co-Founder of BrightHire. Well this is a first… It’s common to time my podcast interview around a milestone for a company like a funding announcement. But, this is the first time that in the span between my interview with the founder to the publishing date that the company announced its acquisition. Last week, BrightHire announced that the company has entered into an agreement to be acquired by Zoom. It certainly is a combination that makes a lot of sense. BrightHire is an interview intelligence platform. We saw its influence firsthand this past summer when VentureFizz hosted a series of AI job searching events. Talent acquisition leaders consistently mentioned BrightHire as the most-adopted application—a signal that immediately led me to reach out to Ben for this interview. As Ben shares, when they started, "interview intelligence" was a brand new category in hiring, and they faced plenty of doubters. But fast-forward to today, and much like the success of companies like Gong for sales teams, BrightHire's value is now obvious. But isn't that the case for all great companies in hindsight? BrightHire's investors include Flybridge, Index Ventures, 01 Advisors, Zoom Apps Fund, and others. Chapters 00:00 Intro 02:48 State of Hiring in the AI Era 06:51 Ben's Background Story 19:40 Getting Started in the Tech Industry 25:26 Origin Story of BrightHire 33:06 Creating a New Category 35:31 The Value of Video in the Hiring Process 41:17 BrightHire Screen - New AI Screening Platform 45:51 Experience of Raising Capital 48:36 Biggest Lessons Learned 50:22 Common Mistakes Companies Make When Hiring 51:57 Lightening Round Questions 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 403 of The VentureFizz Podcast features Nick Ornitz and Shannon Kay, Co-Founders of Topline Pro. Make something people want is the motto behind Y Combinator. It sounds simple, yet so many founders miss this fundamental requirement. Topline Pro is a perfect case study in getting it right. They didn't fall victim to early false positives; instead, they listened, experimented, and successfully pivoted to solve a true, massive problem for an underserved market. Topline Pro is building AI that empowers local home service pros to grow and scale their businesses. They provide a critical platform to help with the marketing, sales, and operations of running a business in the trades, allowing these business owners to focus on their craft. The company recently announced a $27M Series B funding round led by Northzone, with new participation from Tactile Ventures, and Industry Ventures, alongside continued support from existing investors Forerunner Ventures, Bonfire Ventures, TMV, Flybridge, and BBG Ventures. In this interview, we dive into: * The inspirational backstory of Nick and Shannon and how they decided to build a company together after meeting at HBS. * Their initial concept called Dwelling, the "false positive" they experienced, and the strategic pivot. * Their time at Y Combinator and how early access to GPT opened their eyes to the potential of AI. * The value that Topline Pro is providing customers and the exciting opportunities ahead following their Series B. * Growth plans, hiring goals, and the culture they're building at Topline Pro. * Advice for non-AI native companies that are starting to build out their own AI strategy. * 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 402 of The VentureFizz Podcast features Aaron Sekhri, CEO & Co-Founder of Le Walk. Most apps are trying to get you to stare at your phone and create a stickiness factor for doomscrolling. Yet, Le Walk wants you to look up and take in the world. If you have ever experienced a group tour for a museum or some other historical location, it can be a crap shoot and for me, even with the best tour guide, I have a hard time focusing and taking it all in. This is where Le Walk comes to the rescue. It is your personal tour guide, right in your headphones. The company uses AI to enhance, not replace, human creativity. Every tour still relies on real guides, editors, and storytellers — AI just helps amplify their reach. Le Walk recently announced a $4.1M seed co-led by Adverb Ventures and Lerer Hippeau, with participation from Origins Fund and Point72 Ventures. In beta, Le Walk has reached 110k downloads, 160k+ social followers, and 20k+ tours taken. In this interview, we cover: * Aaron’s experience growing up in Hong Kong and how he landed at Stanford to study Symbolic Systems. * Getting his career started in Product Management while at Uber. * His experience at TikTok and what he learned there. * All the details about Le Walk and the plans ahead. * Their content playbook for customer acquisition and why content is king when it comes to building traction for a startup and their strategy around content. * And so much more.

Episode 401 of The VentureFizz Podcast features Nicole Phillips-Bastian of Qatch. This episode was recorded live at Startup Boston Week at Suffolk University which is the third year that I’ve hosted it onsite. Thank you to Stephanie Roulic for the invitation, as it’s a lot of fun and great to be involved in such a meaningful conference. And, since it was hosted live, this episode is audio only and my apologies for the background noise. Personalization isn’t a new term in the world of tech but as a consumer, it often fails. It could be a failure around the data, the actual tech powering the experience, or executional challenges. For Qatch (which stands for Quick Match), they have been able to overcome these challenges by establishing trust with consumers in one of the most coveted spots for obtaining first party data… no, it’s definitely not email, but through text messaging. Qatch is a personalized shopping platform that allows user preferences to dictate what products they see next. Their platform enables the company to capture user engagement to a degree other brands are not, which gives them incredibly valuable insight into what products a specific shopper would buy, so they can recommend it to them in real-time. It all falls under that trust factor which is so important, because if Qatch is not delivering value, it’s easy to block that text message and it is this level of trust that has been so key to their success. Two interesting points to note: 1. Nicole’s co-founder for Qatch is her sister Raquel. 2. They have built a very capital efficient company, as they have raised just under $2M in funding. In this interview, we cover: * The importance of founder-led sales. * Nicole’s background story and her journey into law as a retail attorney with a focus on fashion law and regulations. * All the details about Qatch and why they decided on text messaging as their primary method of communication. * How the platform works and their use of AI. * Sales and getting brands to join their platform, plus how they evolved their pricing strategy. * The competition and how they differ from companies like Stitch Fix. * Her experience raising capital as a female founder and why sales is the best form of funding. * And so much more.

Episode 400 of The VentureFizz Podcast features Rylan Hamilton, CEO & Co-Founder of Blue Water Autonomy. Episode 400! It’s another milestone episode. On November 2, 2017, I published the first episode of The VentureFizz Podcast. My first 11 episodes were an experiment where I interviewed talent acquisition leaders. Christina Luconi was my first guest. Thank you Christina! After seeing the potential, I pivoted to interviewing mainly founders & investors in Boston and NYC. I want to send out shout-out to all the people who have taken the time to share their stories with me and the VentureFizz audience. It has been a pleasure to interview all of you. For Episode 400, I wanted to interview someone who not only has had extraordinary background but someone who is also still building. Interviewing Rylan for this milestone episode was a no-brainer. Rylan’s professional career has been one of exploration and not just one linear path. From graduating from Harvard to enlisting in the Navy as an Engineering Officer for surface warfair, to Harvard Business School, to being the first employee at RunMyErrand which later became TaskRabbit, to learning warehouse robotics at Kiva Systems which ended up being the 2nd largest acquisition by Amazon at the time, to starting his own warehouse robotics company called 6 River Systems which was acquired by Shopify for $450M… to now… working on his latest startup, which no doubt is his biggest swing which is Blue Water Automony… a startup building autonomous ships for the open ocean. The company recently announced a $50M Series A round of funding led GV. This is shortly after announcing a $14M seed round of funding earlier this year back in April. In this interview, we cover how Rylan’s service in the armed forces helped shape his career, his full background story, plus all the chapters along the way, to all the details about Blue Water Authonomy and how this company is disrupting and re-energizing the ship industry in the United States, 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 399 of The VentureFizz Podcast features Luisa Herrmann, Founder & CEO of AINovva. This episode was recorded live at Startup Boston Week at Suffolk University which is the third year that I’ve hosted it onsite. Thank you to Stephanie Roulic for the invitation as it’s a lot of fun and great to be involved in such a meaningful conference. And, since it was hosted live, this episode is audio only and my apologies for the background noise. Entrepreneurs take different paths when it comes to finding ideas to start a business and how they go about funding it. Her company, AINovva was born out of her own need. After working in AI for several years and learning how to code, she built the product to solve her own content-switching exhaustion called AIFred. It handles email prioritization, meeting prep, and relationship management so busy professionals can focus on what matters. And to fund the company, she has bootstrapped it through consulting revenue. Not every company needs an outside investment and if it does, the longer an entrepreneur can hold out… the better situation they will be in when it comes to negotiating the terms. In this interview, we cover: * Advice on attending networking events. * Luisa’s background story in terms of how she got involved in the tech industry and her journey into product management. * Her experience in product roles at ZoomInfo, Validity, and other startups. * All the details about AINOvva. * Advice for hiring your first Product Manager. * And so much more.