Episodi
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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.
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Eli Weiss: @eliweisss
Yotpo: @yotpo
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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 arm, where they have hosted everything from intimate breakfasts, pitch events, and large gatherings of 500+.
Brett is also the GP and syndicate lead for Bulletpitch+, an investment syndicate, which offers deal-by-deal investment opportunities to hundreds of LPs.
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Brett Perlmutter: @brettperl
Bulletpitch: @bullet_pitch
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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); buzzd -> LocalResponse -> acquired by BlueCava.
Early in his career, Nihal honed his ability to spot top entrepreneurial talent by investing in Admob (acquired by Google), Swiftkey (acquired by Microsoft), Tapad (acquired by Telenor), Tala, and Uber, to name a few. Nihal and his wife are now angel investors and LPs in almost 100 underrepresented founders and fund managers.
Nihal is a co-founder of the non-profit “Project Ahimsa,” providing scholarships to disadvantaged youth in India, where his parents immigrated from in the early 1970s. Nihal also recently co-founded initiatives like Help Main Street to help restaurants survive the pandemic, and The 100k Pledge, a social justice tracker of economic empowerment to Black communities. You might catch him running down the Hudson River weekday mornings with founders and his #pitchandrun crew.
Outside of the office Nihal loves to spend time with his wife Reshma and is a big supporter of her non-profit Girls Who Code and her initiative “Moms First.” Around town, you will usually see him with his sons Shaan and Sai and beagle-bulldog Stanley. Nihal is the life of the party, which is why he always spearheads Eniac events.
Nihal graduated from the University of Pennsylvania with a BA in Philosophy and a BSE in Computer Science.
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Nihal Mehta: @nihalmehta
Eniac Ventures: @EniacVC
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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 provides actionable insights and tools to help you visioncast your best year yet.
Whether you're wrapping up the year or gearing up for 2025, this episode is packed with inspiration and practical steps to set your sights on 2025 with clarity and intention.
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Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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 Vigilance, and Internet Research Unit.
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Dennis Hegstad: @dennishegstad
Internet Research Unit: @IRU_DCE
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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 in emerging tech and they have had massive traction in the web3 space, launching multiple collections of digital collectibles that consumers have spent over $50M collecting and trading since 2021. They also partnered with Mattel & Barbie launching the first collection of digital collectibles celebrating the 250 careers Barbie has had since its inception.
Lisa’s work has impacted thousands of high school and college-aged girls all over the world spanning across 15 countries and over 400 educational institutions. In addition to Barbie, Lisa has grown the brand to highlight & celebrate women through live events and global collaborations with partners that include Rolling Stone, Marvel, and the New York Stock Exchange and her work has been featured by Forbes, Fortune, and Apple.
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Lisa Mayer: @lisacmayer
Boss Beauties: @BossBeauties
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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: @Commsor
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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 what’s next through next play.
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Ben Lang: @benln
next play: @nextplayso
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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.
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Nik Sharma: @mrsharma
Sharma Brands: @sharmabrands
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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 Somewhere.com, Scribe Media, and Abstract. 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 Somewhere.com, Scribe Media, and Abstract.
Follow us!
Sieva Kozinsky: @sievakozinsky
Enduring Ventures: @enduring.ventures
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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 (fka WELL Health), FreeWill, Snackpass and others.
Before becoming a full-time investor, Liz was the co-founder and CEO of WayUp, an early-career recruitment platform used by over 7 million candidates and thousands of companies. She launched WayUp in 2014 and ran it for seven years — during which time she raised over $40 million in venture and was with the company as CEO through its M&A exit in 2021.
Prior to WayUp, Liz worked at Google as a product marketing manager. She graduated from the University of Pennsylvania with a Bachelor’s in Political Science, Mathematics and Japanese.
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Liz Wessel: @lizwessel
First Round Capital: @firstround
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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.
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Casey Lewis: @caseymlewis
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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 Wild
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Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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: @jayyeh
Adamant: @adamantfounders
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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: @aunder
Adverb Ventures: @adverbvc
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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.
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Andrew Gazdecki: @agazdecki
Acquire.com: @acquiredotcom
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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 children
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Sara Mauskopf: @sm
Winnie: @winnie
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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.
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Steve Schlafman: @schlaf
Downshift: downshift.me
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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: @RachelRad
Haun: @HaunVentures
Erica Wenger: @erica_wenger
Dear Twentysomething: @deartwentysomething
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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_wenger
Dear Twentysomething: @deartwentysomething
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