

The Room Podcast
Claudia Laurie and Madison McIlwain
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.
Episodes
Mentioned books

May 3, 2022 • 47min
Movers & Shakers S2E4: Naomi Shah, Founder and CEO of Meet Cute, Discusses the Future for Romantic Comedies
Season 2 of Movers & Shakers ends with another incredible guest, Founder and CEO of Meet Cute, Naomi Shah.
Meet Cute is a “rom-com incubator.” Audio, written video, short-form video, long-form video, etc. Meet Cute produces them all. Naomi tells us what inspired the idea for Meet Cute and what it was like for her to raise funding at the start of her founding journey. Naomi also speaks on balancing inspiring other underrepresented founders while not being stuck in the box of a “female founder.”
Other themes discussed in this episode include turning an investment thesis into a company, the “girl boss” trope and what it means for founders, and the future of the romance genre. Let’s open the door.
Watch Extracurricular Here!
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0:05 - Where did Naomi grow up and how did that impact her view of the world? 2:34 - Did Naomi always think she was going to be a founder?4:10 - How did a mechanical engineering degree specifically translate into Naomi’s work?7:50 - What was the initial aha moment for Meet Cute?11:37 - In a few words, what is Meet Cute?12:47 - What is Naomi’s favorite Meet Cute series that they’ve made?14:43 - How was the process of getting the first funding for Meet Cute, and what did Naomi learn?17:49 - What advice does Naomi have for new founders?22:00 - How does Naomi balance paving a wave for underrepresented entrepreneurs, while also removing the stigma of being a “female founder?”27:09 - How do we appropriately help make things more equal for underrepresented founders?29:49 - What is Naomi’s favorite rom-com moment? 32:46 - How has a data-driven approach to storytelling helped unlock unexpected insights on consumers?37:09 - What does the Netflix stock drop say about the volatility of the entertainment market?40:19 - What's next for Naomi and her team at Meet Cute? 42:31 - Who is a woman in Naomi’s life that has had a profound impact on her and her career?
The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.
WX Productions

Apr 26, 2022 • 34min
Movers & Shakers S2E3: Entering the Venture Capital Ecosystem with Rachel Goddard, Partner at Cooley LLP
Our mini-series, Movers & Shakers, continues with Rachel Goddard, a partner at Cooley LLP for over 22 years.
Rachel walks us through her path to becoming a lawyer before becoming a partner at Cooley. She explains why she loves her job and what she and Cooley do to assist emerging managers to start their funds. Rachel also shares some best practices on things new managers might now know, like management fees and GP commitments.
We also get Rachel’s perspective on the next five years for venture funds in light of the past few years being a very hot market and non-accredited investors investing in venture funds.
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0:14 - Where did Rachel grow up and how did that shape her view of the world?0:58 - Did Rachel always want to be a Lawyer?1:41 - What was the pivot that led Rachel into law?3:34 - How is Cooley focused on supporting venture capital?6:04 - What comes up in early conversations with emerging managers?8:43 - Rachel clarifies some of the terminology used to describe different stakeholders. 10:42 - What are the four documents that Rachel always starts with?12:15 - What are some best practices on things like management fees and GP commitments?16:31 - What is the definition of a smaller fund to Cooley?17:21 - What are Rachel’s thoughts on non-accredited investors investing in venture funds?20:25 - What do you think the next five years hold for venture funds in light of the past few years being a very hot market?22:00 - What advice does Rachel have for first-time fund managers and underrepresented fund managers?25:41 - What is coming up for Rachel, personally?27:35 - Who is a woman in Rachel’s life that had a profound impact on her and her career?
The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.
WX Productions

Apr 19, 2022 • 40min
Movers & Shakers S2E2: The Modern Method of Targeted Digital Advertising, a Crypto Bear Perspective and More with Zach Coelius, Co-Founder of Triggit and Coelius Capital
Season 2 of “Movers and Shakers” continues with a legend in the digital marketing ad space, Zach Coelius, Co-Founder of Triggit and Managing Partner at Coelius Capital. Zach and his sister, Susan, played an instrumental role in modernizing the way advertisers use targeted digital ads.
Zach deep dives into “retargeting,” a form of online advertising where the ads are targeted to consumers based on their previous internet behavior. The conversation progresses with the constantly changing legislation on privacy from large companies like Google and Apple. Plus, we further discuss Zach’s take on cryptocurrency, which is very different from the mainstream opinion.
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4:03 - Where did Zach grow up and how did this shape his view of the world?4:37 - Did Zach always think he was going to be an entrepreneur? 5:37 - Why did Zach attend five Olympic Games?8:52 - What is Triggit and how did Zach get started founding it?11:34 - What is the core product of Triggit and what was the competitive landscape like in the ad tech space?14:44 - How does Zach feel about the new privacy changes that Google and Apple are implementing?16:35 - Now in 2022, would Zach recommend entering the digital marketing ad space?18:05 - What are Zach’s thoughts on working within digital marketing on the paying side?19:41 - How is Coelius Capital structured? 22:31 - How would Zach describe his fund? 26:14 - Why is Zach not bullish on Crypto? Has his opinion changed in the last six months? See his mentioned User Manual here. 30:28 - What are some sectors that Zach is bullish on?31:36 - What advice does Zach have for founders looking for funding?36:12 - What’s next for Zach?37:25 - Who is a woman in Zach’s life that has had a profound impact on him and his career?
The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.
WX Productions

Apr 12, 2022 • 33min
Movers & Shakers S2E1: Optimizing SaaS and Cloud Software Companies with Mary D’Onofrio of the Bessemer Venture Partners
We are kicking off our second entitlement of “Movers and Shakers” with a bang!
In The Room with Mary D’Onofrio, partner and co-founder of the growth investment practice at Bessemer Venture Partners.
Topics this week include the very active investing climate of 2022 and how to be proactive when searching for businesses to partner with, how to find, obtain, and retain skilled, specialized new hires, and the difference between growth-stage and early-stage investing.
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3:34 - Where did Mary grow up and how did this shape her view of the world?5:05 - Did Mary always think her career would be in Venture?7:28 - What lessons in “deal-making” did Mary learn during her time at Morgan Stanley?8:15 - What initially brought Mary to Bessemer in 2018?10:10 - What are some of the key characteristics you look for when searching for “the next big thing?”11:52 - How did Mary level up in that way to be able to really effectively evaluate these technical businesses?13:41 - How do you weigh valuing a company and its team versus the growth of the customer and the metric data?15:58 - What will continue to evolve within the cloud ecosystem for enterprise SaaS and software companies?17:34 - What is one company that is changing the way cloud is used or changing the technical ecosystem? 19:02 - How does Mary work with businesses she invests in? 21:10 - Is there a common stumbling block or something that is particularly tricky for new businesses? 24:10 - What advice does Mary have for post-B-level businesses who are struggling to retain talent and hire?25:50 - How is Mary thinking about 2022 and this current very accelerated pace of investing?28:53 - What does the future hold for Mary?29:32 - Who is a woman in Mary’s life that has had a profound impact on her career?
The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.
WX Productions

Mar 8, 2022 • 40min
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.
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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 less bullish on the gig economy than she was when she founded Glamsquad in 2014?26:56 - What is the investment strategy of Clerisy? 29:44 - How is the technology ecosystem evolving in Alexandra’s new home city of Miami?32:07 - What do the next five years hold for commerce?33:54 - How is Alexandra thinking about the evolving tech world, especially in regard to Web3?36:38 - Who is a woman in Alexandra’s life that had a profound impact on her and her career?
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Season 5 of The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.
WX Productions

Mar 1, 2022 • 38min
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.
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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 and faster? And how have the supply chain constraints stunted e-commerce growth?34:40 - What’s next for Rathna?35:00 - Who is a woman in Rathna’s life that has had a profound impact on her and her career?
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Season 5 of The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.
WX Productions

Feb 22, 2022 • 40min
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.
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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 “become an LP” button on his website? 26:46 - Who are some of Mac’s favorite companies that he works with?30:46 - How will access to capital change for new founders in the future?33:32 - What’s next for Mac?34:30 - Who is a woman that has had a profound impact on Mac and his career?
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Season 5 of The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.
WX Productions

Feb 15, 2022 • 28min
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.
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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 in Ash’s life that had a profound impact on him and his career?
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Season 5 of The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.
WX Productions

Feb 8, 2022 • 31min
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.
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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 time to call F7?16:43 - What are the barriers to entry on founding a fund and what was the process like for Joanna, both tactically and emotionally?18:17 - What are some common mistakes that founders make?19:55 - What are some tips for a founder whose idea is not clicking and may need to start thinking outside the box?21:58 - What are some examples of a really good executor and what are things to look for when hiring executors into your business?22:52 - Who is a company in F7’s portfolio that has really knocked their socks off based on their execution?24:15 - Where does Kelly see the investment industry in 10 years? 26:19 - Who is a woman in Kelly’s life that has had a profound impact on her?25:58 - Who is a woman in Joanna’s life that has had a profound impact on her?
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Season 5 of The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.
WX Productions

Feb 1, 2022 • 27min
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.
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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 Dipsea’s core product?7:41 - How was the fundraising journey for Faye? Who wrote the first check?9:08 - What advice would Faye give founders who are just starting to think through an idea with a friend?11:19 - What was the process like finding a product-market fit for this unconventional user experience? 13:09 - Has there been any issues marketing these sensitive subjects?15:25 - How does Dipsea utilize their ability to empower women? 18:00 - How does Dipsea feel about the future of audio platforms and audio creators? 19:10 - What is Faye’s take on social audio platforms?19:42 - What things can people get excited about for the future of Dipsea?20:20 - What’s next for Faye?20:52 - Who is a woman in Faye’s life that has had a profound impact on her and her career?
Be the first to know when new episodes drop - Receive Our Newsletter
Season 5 of The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.
WX Productions