The Room Podcast

We cannot believe that we have concluded season 2, but are even more excited for season 3, airing next week! Thank you so much to all of our listeners for joining us on The Room! We have big plans for Season 3, launching Tuesday, May 4th, featuring international pop star & entrepreneur.... *drumroll please*.... Ciara Wilson! But before we enter the room where it happened with a whole new slew of entrepreneurs, we take a look back on Season 2, its guests, our biggest takeaways, and share some life updates.

Yesterday, Brex announced their Series D round, led by Tiger Global, which now valued them at $7.4 billion. Today, we share an episode of The Room Podcast that just couldn’t wait! Madison and Claudia sit down with Henrique Dubugras, Co-Founder and Co-CEO of Brex in late March. For those who don’t know, Brex is the unicorn fintech startup that provides the all-in-one money and banking solution for startups. Both Brazilian natives, Henrique and his co-founder Pedro Franceschi founded Pagar.me before both attending, then dropping out of Stanford to found Brex. We discuss the key themes of deciding what market you are built for, the multi-time co-founder experience, and Brex’s decision to remain fully remote in the future. Let’s open the door.

In the Season 2 finale of The Room, we sit down with Trae Vassallo, co-founder of early stage venture fund Defy.vc. Out of undergrad at Stanford, Trae worked for the iconic design and innovation firm IDEO, developing products for companies including the Palm Pilot and Dell. During her second year of business school at Stanford, Trae founded Good Technology, a mobile device company whose purpose was to connect islanded devices to the Internet. Good Technology sold to Motorola for $500 million. Through a relationship built with John Doerr and Kleiner Perkins backing Good Technology, she then spent 11 years at Kleiner Perkins. In 2016, Trae and fellow industry veteran Neil Sequeira founded Defy.vc where her paths intersected with our co-host Madison a few years back. On today’s episode we discuss the early days of the Internet, the pros and cons of venture funding, and how an opening of the venture ecosystem has fostered more equity and inclusion across the table. Let’s open the door.

In this week’s episode of The Room, we welcome Liz Meyerdirk, CEO of The Pill Club, a women’s telehealth platform that simplifies and personalizes the experience of prescribing and delivering birth control. Prior to joining The Pill Club Team, Liz was a founding member of the Uber Eats team, leading strategy and global business development for six years. As The Pill Club hit a $100 million run rate, Liz joined as chief executive officer, now leading the team into an exciting product line launch that we have the exclusive on! We talk knowing when to launch a new product line, transitioning CEOs in a growth-stage startup, and the future of women’s health care. Let’s open the door.

This week on The Room, we sat down with Zubin Koticha, co-founder and CEO of Opyn. Opyn is a decentralized finance platform for ethereum options, which recently raised their series A, lead by Paradigm only months after their seed. Zubin graduated from Berkley in 2018 after a Manu-year love and obsession with the crypto space. Post-graduation Zubin worked at Thunder researching blockchain but soon started open with his two co-founders Alexis and Aparna in 2019. Zubin has worked in the crypto space through highs and lows, but given today’s wildly hot crypto market, I think it's safe to say Zubin and the Opyn team are hitting product-market fit. Today we will learn more about fundraising during difficult times, navigating a pivot, and a lot about crypto, DeFi, and NFTs. Let's open the door.

In this week’s episode of The Room, we talk to Allison Barr Allen, Co-Founder and COO of Fast, a one-click, passwordless checkout platform. Allison started her career as tech consultant with PwC then joined Uber in its early days, eventually serving as Head of Global Product Operations on the Money Team. While launching Uber Money products including Instant Pay, Cash, and Wallets, Allison delved into the world of angel investing. In 2019, she met her Fast Co-Founder Domm Holland on Twitter, and within a few months had raised a Series A funding of $20 million. Less than a year later, the Fast team raised $102 million in Series B Funding led by Stripes this January. We discuss the early days of Uber, how Fast grew so fast, and why investing is for everyone. Let’s open the door.

Claudia and Madison welcome Sridhar Ramaswamy, CEO and Co-Founder of Neeva, into The Room this week. Sridhar immigrated from India for his PhD in Data Science at Brown, back in 1989. Today, Sridhar is a Silicon Valley legend, first growing Google’s search ad program to a $115 million business as the Senior Vice President of Ads and Commerce. After 15 years with Google, he joined Greylock as a Partner, a position he still holds today. Now, he’s also onto his newest venture called Neeva, an ad-free private search engine that just announced its Series B funding of $40 million led by Sequoia Capital and Greylock. Through Neeva, Sridhar is rebuilding trust within the Internet, reimagining the ways we can use data for value. We discuss information and privacy in serving your customer, rethinking pre-existing mental models, and leadership principles. Let’s open the door.

In this week’s episode, we welcome Jesse Draper, Emmy-nominated television star turned venture capitalist who founded Halogen Ventures, an early-stage venture firm focused on investing in female entrepreneurs. You’ve seen her on TV in The Naked Brothers Band and as the host of The Valley Girl Show, interviewing tech and business entrepreneurs like Elon Musk and Mark Cuban. As a fourth-generation venture capitalist, Jesse moved away from entertainment to build her own venture firm, Halogen Ventures, which invests entirely in female founding teams. Having recently closed her second fund, Jesse is just getting started on changing the technology ecosystem for the better. Jesse shared with Madison and Claudia the value of building a brand for yourself, her experiences on being an angel and an institutional investor, and her thoughts on the future for female founders. Let’s open the door.

This week on The Room, we sit down with Jane Metcalfe. Jane was the co-founder of the legendary Wired magazine and media company, TCHO chocolates, and now NEO.LIFE. In the early 1990s, Jane and her life partner and co-founder Louis Rossetto came to the Bay Area with the idea and passion to build a magazine and media company devoted to cutting-edge technology. This magazine is what we now know as the iconic Wired, home to some of the most futuristic, but also technology-defining stories. Jane and Louis launched Wired with a big story to tell: the internet becoming mainstream. Today we chat with Jane to hear about her three-time founding stories, from media to chocolates, to biotech, Jane has seen it all and has some deep wisdom to share. Let's open the door.

In this episode, co-hosts Madison and Claudia, interview Ajay Kori, co-founder and former CEO of UrbanStems. They find out more about his journey of founding and scaling this massively successful eCommerce flower delivery service business. He shares a few of his learnings about customer satisfaction and the best way to ensure the longevity of new customers. His inspiring story of failing during the initial phases of the business, but not letting that deter him or his team from making a huge success of the company, should be a great motivation for any aspiring entrepreneur. Ajay shares why he eventually decided to hand over the CEO reins of UrbanStems and start a new business that now has the potential to help millions of people find relief from migraines.