Trailblazers

This week our host, Erica Wenger, chats about her most recent essay: Elephants in the Wild!On this episode Erica dives into her newest essay which draws a parallel between the Ironman Triathlon and successful startups, focusing on the qualities that create strong, long-lasting brands.Using the Ironman community as an example, Erica highlights how Elephants—those built on social attraction, mission-driven growth, and public transparency—foster deep loyalty through identity, community, and shared culture.Read the essay here: Elephants in the WildFollow Us!Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week we chat with Jason Yeh!Jason Yeh is the Founder of Adamant, a fundraising strategy and investor relations firm dedicated to making capital raising less painful for founders and fund managers around the world.As a formal and informal advisor to startups, he’s helped companies raise over $300MM in capital - first as an investor at Greycroft Partners and afterwards as a founder where he led multiple fundraises. His previous company Tape sold to Hustle in 2020.Jason is a graduate of the University of Virginia and Harvard Business School.Follow Us!Jason Yeh: @jayyehAdamant: @adamantfoundersErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week we chat with April Underwood!April Underwood is co-founder and Managing Director of Adverb Ventures, a venture capital firm investing in early-stage technology startups launched in 2023. In addition, April is a member of the boards of directors for Zillow Group and Eventbrite, and a co-founder of the #ANGELS angel investing collective through which she backed over 50 companies as an angel investor. April brings 20 years of experience building software to her role as an investor. Until 2019, April was the first Chief Product Officer at Slack Technologies, Inc, where she led Product, Platform, Design, and Research as the company scaled 10X to IPO-ready in less than 4 years. Prior to joining Slack in 2015, April was director of product at Twitter from 2010 to 2015 from through its IPO.Previously, April has held product, partnerships, and engineering roles at Google, Travelocity, and Intel. April has also been a founder: in 2020, She founded Nearby, an e-commerce marketplace composed of local retailers backed by GV, Obvious Ventures, Redpoint, and many prominent operator angel investors, and her team was acquired by Twitter in 2021. April holds a B.B.A. in Management Information Systems and Business Honors from The University of Texas at Austin (2001), and an M.B.A. from The University of California at Berkeley (2007). Follow Us!April Underwood: @aunderAdverb Ventures: @adverbvcErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week we chat with Andrew Gazdecki!Andrew is a 4x founder with 3x exits, former CRO, and founder of Acquire.com. Gazdecki has been featured in The New York Times, Forbes Wall Street Journal, Inc. Magazine, and Entrepreneur Magazine, as well as prominent industry blogs such as Mashable, TechCrunch and VentureBeat.Follow Us!Andrew Gazdecki: @agazdeckiAcquire.com: @acquiredotcomErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week we chat with Sara Mauskopf!Sara Mauskopf is the CEO and Co-founder of Winnie, a leading marketplace for daycare and preschool helping millions of parents across the United States. Parents use Winnie to discover high-quality local daycares and preschools and learn all about their programs including detailed descriptions, photos, tuition information, licensing status, availability data and more.Child care providers use Winnie to get the tools and support to grow their business. Sara has a background in consumer technology and product management and is also a mom of 3 young childrenFollow us!Sara Mauskopf: @smWinnie: @winnieErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week we chat with Steve Schlafman!Steve is a Professional Transition Coach based in New York. He helps high performers navigate transitions with clarity and intention. He is the founder of Downshift, the world’s first decelerator for high performers in transition.He is also the creator of Where the Road Bends, a newsletter exploring personal evolutions and life transitions. In addition to being a girl dad, this is my life’s work.Follow Us!Steve Schlafman: @schlafDownshift: downshift.meErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week we chat with Rachael Horwitz!Prior to joining Haun Ventures as the Chief Marketing Officer, Rachael served as an Operating Partner at a16z crypto, where she led marketing and communications.Previously, Rachael served as Vice President of Communications at Coinbase. Rachael has served as Communications Director at Google, Facebook, and Twitter, and as a Marketing & Communications Partner at Spark Capital.Rachael began her career at Greer, Margolis, Mitchell, Burns & Associates, a communications firm that provides political consulting and issues management services.Rachael holds a B.A. in Political Science from the University of Washington.Follow Us!Rachael Horwitz: @RachelRadHaun: @HaunVenturesErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

This week, our host, Erica Wenger, welcomes us to the 4th season of Dear Twentysomething!In this season opener, Erica sets the stage for what's to come—real conversations, inspiring stories, and the honest reflections that every twentysomething needs.Get ready to dive into another season filled with wisdom, growth, and the occasional laugh as we navigate the ups and downs of this transformative decade together.Follow Us!Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

Welcome to Season 4 of Dear Twentysomething! The Dear Twentysomething podcast started because we wanted to create a space for ambitious and curious twentysomethings to connect with the successful changemakers they most look up to.A bit about me (your host!)... I'm Erica Wenger, a twentysomething entrepreneur and investor, and I'm so grateful for this badass community of twentysomethings who are here to get knowledge and be inspired!While the twenties can be a time full of questions and doubts, we’re here to humanize the whole thing. You’ll hear from successful trailblazers who come on to share the highs and lows of their 20s and on occasion, it’ll just be me on the mic hosting an episode where I share a recent reflection or story from my own life as I too am navigating this wild decade. Thank you for being here!Follow us!Erica: @erica_wengerEmail us!deartwentysomethingpod@gmail.com//Royalty Free Music from Bensound

This week our host, Erica Wenger, recaps Dear Twentysomething Season 3! On this 100th episode of Dear Twentysomething, we look back on the 3 most popular solo and guest episodes of this season! Stay tuned for Dear Twentysomething Season 4! Follow Us!Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething