The Room Podcast

Claudia Laurie and Madison McIlwain
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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. For The Room Podcast in your inbox every week, subscribe to our newsletter. 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
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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. 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 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? 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
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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. 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 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? 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
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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. 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 “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? 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
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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. 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 in Ash’s life that had a profound impact on him and his 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
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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. 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 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? 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
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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. 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 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
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Jan 25, 2022 • 43min

S5E2: Scaling & innovating on CPG with Graham Fortgang of MatchaBar

In The Room with Graham Fortgang, Founder of MatchaBar. Season 5 continues with Graham Fortgang, co-founder, and CEO of MatchaBar. Graham runs MatchaBar alongside his brother, Max, whom he’s worked with for over 7 years. We asked Graham why he and Max fell in love with matcha and, to break down their mission of bringing matcha to the mainstream whether through grocery stores, online shipping, or wholesale offerings. From guerrilla marketing in the busiest grocery stores to flying to Japan to study the origins of matcha, Graham has dedicated his life to his cause of bringing more attention to the benefits of matcha over your regular caffeinated drink. This week’s episode explores insights and themes such as the thousand-year-old origins of matcha, the power of hustle in building a business, and tactical tips on being an omnichannel retailer in 2022. Let’s open the door. For The Room Podcast in your inbox every week, subscribe to our newsletter. 4:29 - What was Graham doing before MatchaBar?6:40 - What made Graham and his brother, Max, decide to take MatchaBar seriously?9:51 - What was it like owning and operating cafés?11:53 - How did guerrilla marketing become an integral part of the MatchaBar brand?13:08 - How did it benefit Graham to study the history of matcha?16:00 - Who were the early suppliers of matcha to MatchaBar?18:02 - How was the transition from real cafés to a CPG brand?20:37 - Who was the first retail partner that believed in MatchBar?22:30 -What brought the decision to capitalize MatchaBar?24:14 - What has been the added value of having household name celebrities as endorsers?25:14 - What is Graham’s favorite matcha drink?26:33 - Why direct to consumer has been successful for MatchaBar and how the company has incorporated E-Commerce?23:44 - What advice does Graham have for another founder planning to rebrand their business?30:10 - Graham discusses how customers are the most sensitive they’ve ever been.31:10 - Who is in Graham’s D2C tech stack?32:22 - What is the next tool or platform that will help brands connect with their customers?35:02 - Where does Graham think this current movement for brand and product transparency is going next?37:05 - What are other trends to look out for in the CPG category?38:19 - What is Graham looking forward to next in his life and career?39:35 - Who is a woman in Graham’s life that had a profound impact on him? 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
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Jan 18, 2022 • 41min

S5E1: Jeremy Cai and Italic are Changing the Game for Manufacturers and Merchants

In The Room with Jeremy Cai, Founder, and CEO of Italic. We start off season 5 of The Room with Jeremy Cai, the Founder and CEO of Italic. Jeremy and Italic are changing what it means to be a manufacturer by connecting directly to customers and consumers, breaking from the traditional path of utilizing a middle-man distributor. Jeremy details the evolution of Italic, expanding on the changes they’ve made to the business model. Plus, we ask him about the future of the E-Commerce space and any predictions he may have. For The Room Podcast in your inbox every week, subscribe to our newsletter. 3:21 - Who is Jeremy Cai and how has his family background influenced his interests?4:42 - Jeremy compares what he learned from his time as a Theil Fellow to his time running his two subsequent startups.8:02 - What inspired the start of Italic? 12:37 - Who was the first manufacturer to sign up with Italic? 15:41 - What was the first product Italic sold and how did Italic get consumers to join?18:01 - What is the design process of Italic’s product offering?22:45 - Was getting a VC the first step in getting Italic off the ground? 23:18 - Who was the first Venture that said yes to supporting Italic? 24:48 - What led Italic to step away from their original mandatory membership model?27:11 - What does Jeremy think the next innovation in E-Commerce is?30:24 - Italic is not a brand but, they can create an experience.32:56 - What is Jeremy’s favorite product on Italic?33:51 - How has the current supply chain crisis affected Italic?35:14 - What advice would Jeremy give to a new E-Commerce startup founder?36:30 - What’s new for Jeremy in 2022?38:29 - Who is a woman that has impacted Jeremy? 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
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Dec 7, 2021 • 37min

Movers & Shakers Ep 4: Ryan Mundy of Alkeme Health

Welcome to the last episode of our four-part mini-series Movers & Shakers! This week, Madison and Claudia sit down with Ryan Mundy, Founder & CEO of Alkeme Health. Any football fans? You may also recognize Ryan as the Super Bowl-winning safety for the Pittsburgh Steelers. After eight seasons in the NFL and playing across three teams, Ryan retired at age 31 and embarked on a self-discovery journey to find his identity outside of football. This led him to spend time both on the investing side at Techlete Ventures and starting his first company SWZLE, a sustainable CPG brand. That year, Ryan and his family faced an unfortunate number of personal health crises, ultimately shedding light on healthcare inequalities that millions of Black Americans must face. From this personal experience came Alkeme Health, a digital health platform that features content from black practitioners and respected experts in wellness, including psychology and mindfulness to tackle the issues that are historically unaddressed by health tech, such as intergenerational trauma, systemic racism, anxiety and microaggressions. The platform is set to launch in January 2022. This week’s episode of The Room Podcast explores insights and themes such as endurance on and off the field, building an ecosystem of culturally competent care, and healthcare's future in America. Let's open the door. Movers & Shakers is proudly sponsored by our friends at Silicon Valley Bank and Cooley.

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