Trailblazers by Erica Wenger

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 Poi...

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 forgetta...

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 Direc...

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...

This week we chat with Brett Perlmutter! Brett is the founder of Bulletpitch. Bulletpitch is redefining venture through media. Their flagship product is a publication that highlights and performs high-level diligence on top-tier startups. The publication has become a staple for 1000s of investors and has helped companies raise millions of dollars by being featured. Bulletpitch also has an events a...

This week we chat with Nihal Mehta! At Eniac, they call Nihal the human Rolodex, thanks to the thousands of connections he has made with some of the world’s top companies and brands. He developed many of these connections (and scar tissue!) over the past 20+ years while founding five startups: Philly2nite -> UrbanGroove -> Chapter 7 bankruptcy; ipsh! -> acquired by Omnicom (NYSE: OMC); bu...

This week our host, Erica Wenger, takes a step back to reflect on the highs, lows, and lessons of 2024 while looking ahead to the opportunities of 2025. In this episode, she shares her personal process for year-end reflection, breaking it down into eight fool-proof buckets to help you identify what went well, what didn’t, and how to grow. From celebrating wins to recalibrating for the future, she...

This week we chat with Dennis Hegstad! Dennis is an experienced entrepreneur and founder, having co-founded LiveRecover, an SMS marketing company for Shopify merchants that scaled to thousands of users and drove over $100 million in additional revenue. He also founded OrderBump, a Shopify app for upsells, which he quickly grew and sold within just 100 days. Currently, Dennis is the co-founder of V...

This week we chat with Lisa Mayer! Lisa Mayer is the co-founder & CEO of Boss Beauties, a next gen tech company backed by Serena Ventures, the $100M+ venture fund founded by world class athlete Serena Williams. Boss Beauties inspires & elevates the next generation of women & girls to be everything they want to be through technology, content, and education. Boss Beauties was first born...

This week we chat with Mac Reddin! Mac Reddin is the Founder and CEO of Commsor. At Commsor he's focused on building tools to enable companies to embrace Go-to-Network, a more sustainable way to grow compared to traditional direct Go to Market motions. Prior to Commsor he bootstrapped and exited various businesses across gaming, fashion, and software. Follow us! Mac Reddin: TheTeaGuns Commsor:...

This week we chat with Ben Lang! Ben has spent his life hopping between New York, Tel Aviv, and San Francisco. He is a builder, former founder, and community guy, always in multiple places at one time. He was an early member of the Notion team, where he led community for nearly 5 years. He actively makes angel investments and advises a few select startups. He’s helping world-class talent discover...

This week we chat with Nik Sharma! Nik is the CEO of Sharma Brands, a strategic initiatives firm working with a wide range of brands to help grow and scale revenue across digital platforms. Nik is one of AdWeek’s Young & Influential, Forbes 30 under 30, Business Insider's up and coming Investors to Watch, and an investor and advisor to some of the fastest-growing brands in commerce. Follow...

This week we chat with Sieva Kozinsky! Sieva is a founder of Enduring Ventures, a long-term holding company that buys wonderful businesses and holds them forever. Sieva is a lifelong entrepreneur who started Enduring Ventures with Xavier Helgesen, taking inspiration from Warren Buffett's Berkshire Hathaway model. Together with investors, they own stakes in over 20 companies, including Somewher...

This week we chat with Liz Wessel! Liz Wessel is a Partner at First Round Capital, a pre-seed and seed venture fund, based in San Francisco. Prior to joining First Round, she was a Visiting Group Partner at Y Combinator, where she worked directly with over 110 early-stage startups. Liz has also been investing as an angel since 2016, backing over 60 startups, including Ramp, ScaleAI, Ro, Artera (fk...

This week we chat with Casey Lewis! Casey is a youth trends expert and brand consultant. Formerly an editor at Teen Vogue, MTV, and New York Magazine. She now writes After School, a trends newsletter read by 45,000+ people, and helps companies reach Gen Z. Follow us! Casey Lewis: @caseymlewis Erica Wenger:  @erica_wenger Dear Twentysomething:  @deartwentysomething

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, missi...

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 l...

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 a...

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: @agazdecki Acquire.com: @acquiredotcom Erica Wenge...

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...

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 b...

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 Pa...

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 transforma...

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 w...

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_wenger Dear Twentysomething:  @deartwentysomething