Courtney Powell: COO & Managing Partner at 500 Global

This week, we chat with Courtney Powell! Courtney is COO and Managing Partner at 500 Global, tasked with helping the firm scale globally and explore new opportunities across markets. She is responsible for operations across the team to pursue 500 Global’s mission of uplifting people and economies through entrepreneurship.She is also on the advisory council of Harvard Kennedy School’s Mossavar-Rahmani Center for Business and Government supporting more effective interactions between the public and private sectors for the public good. Her ties to 500 Global go back to 2012, when she founded PublikDemand, a member of Batch 4 in 500’s Global Accelerator Program. She went on to become CEO of Agent Pronto, one of the largest real estate agent referral services in North America, which was ultimately acquired by Fidelity National Title Group.Most recently, Courtney was the Head of Corporate Development at Keller Williams, the largest real estate franchise in the world. During her tenure, she established the company’s first corporate innovation program, and worked with Keller Capital to invest and acquire tech companies in the real estate space.Courtney was named to the Forbes 30 Under 30 list in 2012, received the Twilio Doer Award in 2013, and became a Google Business Leader in 2015. She attended the University of Texas at Austin, where she studied French and Corporate Communication.Follow Us!Courtney Powell: @CourtneyPowell500GlobalVC: @500GlobalVCErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week, we chat with TJ Taylor! TJ has spent over a decade as an early stage consumer operator—most recently Employee #1 at Raya and founding team member at Dispo. His areas of focus has been GTM and Growth (product, marketing, and community led).Currently, he is running consultancy and advisory company for consumer startups. Additionally, he’s serving as a Venture Scout for the consumer team at Headline (looking at early stage consumer tech companies). Follow Us!TJ Taylor: @tjtaylrErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week, our host, Erica Wenger, shares a number of practical and unconventional tips on how to fundraise effectively as an early-stage founder!In this episode, Erica breaks down the fundraising process beyond the typical advice, offering insights on how to approach investors, craft a compelling narrative, and stand out in a crowded market. She challenges common misconceptions about fundraising and highlights creative strategies founders can use to secure capital—whether through unconventional networking, alternative funding sources, or leveraging unique market positioning.If you're an early-stage founder navigating the fundraising landscape, this episode is packed with actionable insights to help you raise capital with confidence!Follow Us!Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomethingRead less

This week, we chat with Siqi Chen!Siqi is the founder and CEO of Runway, a next generation FP&A platform that makes finance actually understandable and accessible to the entire team.As an operator and founder, he served as the CEO of Sandbox VR (a16z), VP of Product and Growth at Postmates (later acquired by Uber), CEO of Hey, Inc (Google-funded, acquired by Postmates), Head of Product at Zynga (IPO 2011) and CEO of Serious Business (funded by Lightspeed, acquired by Zynga). In addition to his operational roles, Siqi is an investor in nearly a hundred companies, including notable names like ElevenLabs, Amplitude, Pipe, and Mercury.Prior to his entrepreneurial ventures, Siqi made significant contributions at NASA JPL, where he achieved the distinction of being the sole recipient of a Congressional Space Act award while still in school. This recognition was a result of his contributions to machine vision technology on the Mars Exploration Rovers.Follow Us!Siqi Chen: @bladerRunway: @runwaycoErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week, we chat with Troy Osinoff!Troy is the Co-founder of JUICE, a digital marketing agency credited by Facebook as being a top 1% agency with clients such as L’Oreal, Super Coffee, Solidcore & Bartstool Sports. Prior to JUICE, Troy helped a bankrupt shoe company reach profitability, grew a Grammy-winning recording studio, created a viral media site called Make A Dare (featured on Dr. Phil), co-founded a media company with 1.7M visitors daily ($0 paid promotion), and created a viral Tumblr that was turned into a nationally sold book (published by Penguin, sold to FOX). Troy also lead digital marketing for the largest HVAC company in the world ($4.2B annual sales), created a group of eCommerce stores grossing 7 figures of revenue, and was Head of Customer Acquisition at BuzzFeed. In 2021 Osinoff became a partner at Magic Fund, an early stage VC fund.Follow Us!Troy Osinoff: @yoJUICE: /thinkjuice.comErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week our host, Erica Wenger, chats about her most recent essay: Getting Off The Alphabet Train!On this episode Erica dives into her newest essay which challenges the traditional VC funding model. Getting off the Alphabet Train explores the shift away from traditional VC funding, where startups chase valuations through seed and Series rounds.Instead, a new wave of “elephant” companies is prioritizing profitability, community-driven growth, and long-term sustainability over constant fundraising. The essay highlights how changing market conditions and new funding models are reshaping the startup landscape.Read the essay here: Getting Off The Alphabet TrainFollow Us!Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week, we chat with Jacqueline Blackburn!Jacqueline is a Principal at Decisive Point and leads the acceleration portfolio. Jacqueline graduated from the United States Naval Academy and led forward-deployed teams in the Naval Explosive Ordnance Disposal Community. She was responsible for training and building small teams for no-fail missions in the Middle East and Africa.Prior to Decisive Point, she spent several years at J.P. Morgan working closely with founders and building out their early-stage Technology and Disruptive Commerce practice.Follow Us!Jacqueline Blackburn: @therealistjacDecisive Point: @decisivepointvcErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week, our host, Erica Wenger, goes solo to break down the secrets to hosting a standout curated tech event.From timing it just right to crafting the perfect guest list. Erica shares insider tips on how to create an event that’s both high-value and high-impact. You’ll learn what makes a great tech gathering, how to foster meaningful conversations, and the key elements that separate a forgettable meetup from an exclusive must-attend experience.Whether you’re planning your first event or looking to elevate your approach, this episode is packed with expert insights to help you curate a tech event that people will be talking about long after it’s over.Follow Us!Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week we chat with Grace Clarke!Grace Clarke is the founder of GGC Consulting, redefining how brands grow by building community-powered flywheels, not funnels, growing brands like Graza, Madewell, Jones Road, Estee Lauder, Target, Google. She is also the founder of GraceAI, a marketing strategy and calendar generator (basically an AI clone of her brain). She also runs the Gen Z Board of Directors, an insights network of young people, is an artist, and splits her time between New York and Paris.Follow us!Grace Clarke: @graceclarkeGGC: grace-clark.comErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week we chat with Eli Weiss!Eli has spent the last decade building and operating early-stage startups. He is particularly known for his work around the convergence of Customer Experience and Customer Retention at DTC brands such as Jones Road Beauty, OLIPOP, and many more. After years of building brands that put the customer first, he’s switched to the tech side to help build the future of Customer Retention at Yotpo.Follow us!Eli Weiss: @eliweisssYotpo: @yotpoErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething