The Room Podcast

Welcome to the Room. A series interviewing your favorite tech founders and funders. Our guests were in the room where it happened and they’re sharing their stories. 

Latest Episodes

8

March 08, 2022 00:40:02
S5E8: Alexandra Wilkis Wilson, Co-Founder of Gilt Groupe, Is Sharing Her Experience With New Founders as the Co-Founder and Managing Partner of Clerisy

S5E8: Alexandra Wilkis Wilson, Co-Founder of Gilt Groupe, Is Sharing Her Experience With New Founders as the Co-Founder and Managing Partner of Clerisy

In The Room with Alexandra Wilkis Wilson, Co-Founder of Gilt Groupe, GLAMSQUAD, and Clerisy.  In our final episode of the season, and 50th episode of The Room Podcast, Alexandra shares her experience breaking into the online retail fashion world with her smash hit, Gilt Groupe, alongside her partner, Alexis Maybank. Alexandra explains how she had limited merchandising experience but took advantage of the consumer ‘FOMO’ by creating the early forms of fashion brand “drops.”  In this conversation, we cover themes such as the original “drop” model, what’s happening in Miami’s ‘Silicon Valley Beach’, and the adoption of Omni-channel 3.0. For The Room Podcast in your inbox every week, subscribe to our newsletter.  4:23 - Where did Alexandra grow up and how did that experience shape her view of the World?5:55 - Did Alexandra always think she would become a founder?7:35 - When Alexandra was at Harvard, were many people looking to become founders?10:03 - What was the retail climate like in 2007 when Alexandra started Gilt Groupe?13:05 - Did Alexandra realize she was creating the early stages of fashion brand “drops”?14:24 - What inspired Alexandra to structure Gilt Groupe in the way that it was?15:13 - Was it difficult pursuing larger purchase orders without having much retail fashion experience?18:32 - Who's the first person to say yes to Alexandra and Gilt Groupe?20:39 - What challenges did Alexandra face when building the robust catalog of items on Gilt?25:31 - Is Alexandra more or ...

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7

March 01, 2022 00:38:06
S5E7: Rathna Sharad, CEO and Founder of FlavorCloud is Unlocking International Supply Chains and Shipping for Startups

S5E7: Rathna Sharad, CEO and Founder of FlavorCloud is Unlocking International Supply Chains and Shipping for Startups

In The Room with Rathna Sharad, Founder, and CEO of FlavorCloud. With the constant growth of social media and the impacts of the pandemic, more businesses and brands are looking to export or import internationally. And since consumer expectations are only increasing, there is immense pressure on independent companies to unlock access faster. Enter, FlavorCloud, who takes care of the whole cross-border shipping process, including all customs requirements, wherever you’re shipping to. In this episode, CEO and co-founder, Rathna covers topics such as unlocking “anywhere to anywhere” shipping, the increasingly higher expectations of online consumers, and theories on how the supply chain issues will shape up this year. For The Room Podcast in your inbox every week, subscribe to our newsletter.  3:34 - Where did Rathna grow up and how did that shape her view of the world?5:24 - When Rathna was growing up did she want to be a founder?7:04 -  What did the logistics ecosystem look like in the early 2000s?9:31 - What challenges did Rathna face when switching from B2B to B2C?13:02 - How did Rathna’s first company, Runway to Street, inform what is now FlavorCloud?18:45 - Who was the first person to say yes to investing in FlavorCloud?19:41 - Who is the target customer of FlavorCloud?20:57 - Which international markets are growing the fastest and where would Rathna recommend retailers expand?25:25 - How will the supply chain shape up next year?29:09 - What advice does FlavorCloud have for businesses that manufacture and distribute in multiple countries?32:06 -  How has consumer expectation shifted the need for logistics to become faster ...

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6

February 22, 2022 00:40:06
S5E6: Mac Conwell of RareBreed Ventures is Serving His Community by Turning LP Relationships Upside Down

S5E6: Mac Conwell of RareBreed Ventures is Serving His Community by Turning LP Relationships Upside Down

In The Room with Mac Conwell, the Managing Partner and founder of RareBreed Ventures.  After founding a few of his own startups, Mac’s life changed when he learned about the world of VCs and funders. This inspired him to start RareBreed Ventures, a pre-seed fund that invests in founders outside of large tech ecosystems. Mac and RareBreed provide resources, capital, and financial education to new and underrepresented founders.  This episode discusses; strategies for bridging the gap between funders and marginalized founders, the unique uses of TEDCO, a state-sponsored VC that provides resources to early stage companies in Maryland, and how Mac is utilizing Rule 506(c) to publicly fund new founders.  For The Room Podcast in your inbox every week, subscribe to our newsletter.  0:17 - Where did Mac grow up and how did that shape his view of the world? 1:21 - How did Mac’s early career start put him on a path to entrepreneurship? 3:15 - At what point did Mac decide to quit his job and become an entrepreneur?5:06 - What resources are available now versus when Mac started his career?5:53 -  Who did Mac start his first company with?8:59 - How did Mac’s experience as a founder lead him to venture?12:27 - What is it like to be primarily investing in your home state?16:19 - Is there a “top of the funnel” issue when it comes to who is receiving funding and financial education?18:13 - What is TEDCO and how is it tying venture to state funding?20:13 - Why did Mac start RareBreed Ventures?21:31 - How and why does Mac have a ...

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5

February 15, 2022 00:28:28
S5E5: Early Stage, Go-To-Market Strategies with Ash Rust of Sterling Road

S5E5: Early Stage, Go-To-Market Strategies with Ash Rust of Sterling Road

In The Room with Ash Rust, Managing Partner at Sterling Road. Since moving to Silicon Valley in 2008, Ash Rust has become an experienced mentor to startup founders and funders. Ash realized that he didn't like the traditional Silicon Valley approach of meeting someone for a small amount of time before making a decision on a large check, as fast as possible, because “that's the cool thing to do.” Instead, he chooses to spend a lot of time with founders early on to build an organic and more valuable relationship. This allows a better perspective on how Ash can properly assist the project.  This episode includes insights on making an enterprise sale as an early or first-time founder, the right time to implement a sales team and who should be on it, and the current and future impacts of developing technologies on enterprise sales. For The Room Podcast in your inbox every week, subscribe to our newsletter.  3:57 - What interested Ash about becoming a founder and sales coach?7:48 - What is important when making your first enterprise sale?11:38 - When is the right time to bring a dedicated sales person to your team?13:41 - How do you balance asking for a sale while managing an overcritical internal mindset?17:00 - How has the landscape changed over time for making a sale?18:44 - As technology continues to develop, what will the future of optimizing the sales funnel look like?21:36 - What are some indicators or metrics of sales success?24:51 - Are there any overlooked tips in mastering enterprise sales?26:04 - Who is a woman ...

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4

February 08, 2022 00:31:06
S5E4: Kelly Graziadei and Joanna Lee Shevelenko of F7 Ventures Create an Inclusive Space for Women In Ventures

S5E4: Kelly Graziadei and Joanna Lee Shevelenko of F7 Ventures Create an Inclusive Space for Women In Ventures

In The Room with Kelly Graziadei and Joanna Lee Shevelenko, General Partners of F7.  For this episode of The Room, we chat with the women who lead the investments and operations of F7. F7 is a seed investment fund, composed of seven senior female operators. With their combined 16 years at Facebook, Kelly and Joanna explain what they learned from their time there and how they want to use their experience, relationships, and capital to make a difference. Kelly and Joanna manage F7 because they see a huge issue with the number of women that have “a seat at the table” in the investment industry and they want to encourage more women to be founders.  This conversation describes some of the barriers to entry as a woman in the investment world and the importance of giving everyone an equal starting place in the industry. Plus, Kelly and Joanna reveal some common mistakes that new founders make and explain how the women of F7 can be beneficial at any stage in the startup process. For The Room Podcast in your inbox every week, subscribe to our newsletter.  3:55 - Joanna left Facebook after 9 years to pursue F7, how did her time there shape her career?5:57 - How did Kelly get involved with VCs, and why did she see the need for F7?7:32 - How did Kelly first make the transition into Venture? What was the aha moment that venture was next for her career?12:02 - What is the initial mission and investment thesis of F7?13:55 - What stage in a startup is the right ...

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3

February 01, 2022 00:27:23
S5E3: How Faye Keegan of Dipsea is Empowering Women Using Audio-First Content with Sex-Positive Narratives

S5E3: How Faye Keegan of Dipsea is Empowering Women Using Audio-First Content with Sex-Positive Narratives

In The Room with Faye Keegan, Co-Founder, and CEO of Dipsea.  Consumers are leaning more and more into audio as their primary medium for receiving content. Faye describes how Dipsea is the first of its kind by using the new consumer love of personal audio to empower women. “Sexy audio stories and intimate wellness sessions to help you find joy and confidence in and out of the bedroom.” This episode covers concepts such as good practices when partnering on a startup with a friend, the current state of audio platforms creators, and advice for fundraising in a non-traditional space. Bonus in time for Valentine's Day, Faye explains why it’s so important to sexually empower women and create a safer environment for sexual education.  USE CODE: “THEROOM” on Dipsea's Website to get a free 30-day subscription to Dipsea and have access to over 500 stories, hot & heavy content, dreamy bedtime stories, wellness sessions, and an ad-free experience. Plus, you can cancel at any time. For The Room Podcast in your inbox every week, subscribe to our newsletter.  0:08 - Where did Faye grow up and did she always want to be a founder? 1:06 - What did Faye think of her time at Bridgewater and how did it affect her leadership style?2:06 - What was a lesson that Faye learned at Bridgewater that she has taken with her into the Dipsea culture? 3:16 - What inspired Faye’s career shift from investing to software engineering?4:40 - What was the initial a-ha moment that sparked the creation of Dipsea?6:19 - How did Faye meet Gina?6:54 - What is ...

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