Trailblazers by Erica Wenger
Trailblazers is a business podcast hosted by Erica Wenger, a General Partner at Park Rangers Capital. Each week, she interviews top investors, founders, and business icons who have achieved success through unconventional paths. The show features stories of billion-dollar exits and early pivots, offering insights into how the next generation of firms and companies are built. New episodes are released every Tuesday.
Episodes
Marshall Sandman: What It Takes To Win In Venture Capital | Trailblazers Podcast Episode 47
In this episode, we sit down with Marshall Sandman, founder and Managing Partner of Animal Capital, a seed-stage venture firm whose first fund backed four unicorns and ranked in the top 1% of its vintage.We discuss how Marshall built a venture firm backed by some of the world's most recognizable celebrities and entrepreneurs, the reality of raising a fund in a down market, why most founders sh
Polina Pompliano: The Power Of Putting Yourself Out There l Trailblazers Podcast Episode 46
In this episode, we sit down with Polina Pompliano, founder of The Profile and author of Hidden Genius, where she studies the lives, habits, and minds of exceptional people.We discuss what drives some of the world's most successful people, how putting yourself out there creates unexpected opportunities, why flaws and insecurities can become an advantage, the role of vulnerability in storytelli
Rebecca Kaden: The Biggest Myth About Great Ideas l Trailblazers Podcast Episode 45
In this episode, we sit down with Rebecca Kaden, General Partner at Union Square Ventures, where she invests in the next generation of AI, software, and technology companies shaping the future.We discuss why AI is still dramatically underhyped, how venture capitalists identify world-changing technologies before everyone else, the future of open versus closed AI ecosystems, why the best investors t
John Hu: How I Built A $40M Business With 30 Employees l Trailblazers Podcast Episode 44
In this episode, we sit down with John Hu, the co-founder and CEO of Stan, the platform helping creators turn their audience into thriving businesses.We discuss how AI is changing entrepreneurship, why the best companies stay relentlessly founder-first, what it takes to build a $40M business with just 30 employees, the future of creator entrepreneurs, the importance of distribution and personal br
Nicole Behnam: Stop Asking Successful People for Advice l Trailblazers Podcast Episode 43
In this episode, we sit down with Nicole Behnam, an entrepreneur, investor, and podcast host known for interviewing some of the world's top founders, investors, and business leaders.We discuss how to build relationships with influential people, why traditional education leaves entrepreneurs at a disadvantage, the future of AI and entrepreneurship, the power of storytelling, how to build a cult
Geoff Woo: The Ugly Truth About Venture Capital l Trailblazers Podcast Episode 42
In this episode, we sit down with Geoff Woo, Co-Founder and Managing Partner of Antifund, an unconventional venture capital firm investing in the next generation of companies across technology, consumer, defense, and culture. Geoff is also the Founder and Executive Chairman of Ketone-IQ and has built businesses alongside creators like Jake and Logan Paul, giving him a unique perspective at the int
Ann Miura-Ko: Why Great Businesses Still Fail l Trailblazers Podcast Episode 41
In this episode, we sit down with Ann Miura-Ko, Co-Founding Partner of Floodgate and one of Silicon Valley's earliest investors in companies like Lyft, Twitch, Twitter, and Okta. After nearly two decades investing in founders at the earliest stages of company building, Ann shares how she identifies exceptional entrepreneurs long before the rest of the market. We discuss how Twitch almost never
Kate McAndrew Inside The Mind Of A $100M Investor l Trailblazers Podcast Episode 40
In this episode, we sit down with Kate McAndrew, Co-Founder and General Partner of Baukunst, a $100 million pre-seed venture fund investing in the next generation of founders. After spending more than a decade investing in over 100 early-stage companies, Kate shares how she evaluates entrepreneurs long before the rest of the market catches on. We discuss what makes a startup worth investing in, ho
Nas Daily: The Internet Tried To Cancel Me l Trailblazers Episode 39
In this episode, we sit down with Nas Daily, entrepreneur, creator, and founder of one of the world's largest creator brands. After building an audience of more than 70 million followers through nearly a decade of daily videos, Nas made the biggest gamble of his career by pivoting his content to AI. We discuss why he believes AI will create the next Walt Disney, how he built and manages a comp
Justin Welsh: How I Built A $15M Business Alone l Trailblazers Podcast Episode 38
In this episode, we sit down with Justin Welsh, entrepreneur, writer, and founder of a $15 million one-person business. After helping build two billion-dollar companies and raising more than $300 million in venture capital, Justin chose a different path; one focused on freedom, leverage, and ownership. We discuss the power of writing, the future of entrepreneurship in the age of AI, why many found
Mark Cuban: How To Win When You're Broke l Trailblazers Podcast Episode 37
In this episode, we sit down with Mark Cuban to uncover the principles behind his success in business. From whether entrepreneurs should drop out of school to the toughest challenges he faced while building his companies, Mark shares the lessons that shaped his career. He explains why curiosity is a competitive advantage, how ego can hold people back, and what separates successful entrepreneurs fr
Leah Solivan: Founder of TaskRabbit and Precedent.vc
This week, we chat with Leah Solivan!Leah is the founder of TaskRabbit, the pioneering on-demand marketplace that helped redefine the future of work and laid the foundation for what we now know as the gig economy. As CEO for eight years, she scaled TaskRabbit into an international business operating in more than 40 cities before overseeing its successful acquisition by IKEA in 2017.Today, Leah con
Mariam Naficy: Founder of Minted and CEO at Arcade
This week, we chat with Mariam Naficy!A serial entrepreneur and visionary leader known for pioneering new ways to connect creativity, technology, and human expression. Mariam is the Founder and Chairman of Minted, and now the Founder and CEO of Arcade, a platform that uses AI to help people communicate visually — transcending geographic and language barriers to connect creators, artisans, and cons
Marlon Nichols: Co-Founder of MaC Venture Capital
This week, we chat with Marlon Nichols!Marlon is the co-founder and managing general partner of MaC Venture Capital, a leading seed-stage firm backing visionary founders who are redefining industries and shaping the future. Under his leadership, MaC has grown into one of North America’s largest seed-stage venture firms, with over $600 million in assets under management.He’s backed an incredible po
Paige Hendrix Buckner: CEO at All Raise
This week, we chat with Paige Hendrix Buckner!Paige is the CEO of All Raise, a nonprofit working to accelerate the success of women and non-binary venture capitalists and reshape the culture of the venture ecosystem. She previously served as All Raise’s Chief of Staff and Interim CEO before stepping into the role full time.Before joining All Raise, Paige was the COO of Founder Gym, the largest onl
Rob Schutz: Founder of Snagged
This week, we chat with Rob Schutz!Rob is a serial entrepreneur, operator, and growth expert who’s spent his career building and scaling technology businesses that challenge outdated systems. He’s the founder of Snagged, where he helps entrepreneurs, startups, and established companies acquire premium domain names—and he’s also the co-founder of Ro, the digital health platform that’s transformed h
Mayssa Chehata: Founder of Behave Candy
This week, we chat with Mayssa Chehata!Mayssa is the founder of BEHAVE Candy, the first low-sugar, clean-label candy designed not to spike blood sugar. Inspired by her love of sweets and her father’s diabetes, she set out to create a better alternative—partnering with chefs and food scientists to develop candy that delivers on taste while helping reduce sugar in the food system.In addition to buil
Satya Patel: Co-Founding Parter of Homebrew and Screendoor
This week we chat with Satya Patel! Satya is the co-founding General Partner of Homebrew, a seed-stage venture capital firm based in San Francisco. Through Homebrew, Satya has backed some of the most impactful startups of the past decade, including Chime, Cruise, Finix, Gusto, Habi, Honor, Plaid, and Shield AI.He’s also the co-founder of Screendoor, an investment platform designed to support emerg
Kipp Bodnar: CMO at HubSpot
This week we chat with Kipp Bodnar!Kipp is the Chief Marketing Officer of HubSpot, the #1 CRM platform for scaling companies, where he leads the company’s global marketing strategy—driving awareness, demand, and growth across one of the most influential software brands in the world.Before stepping into the CMO role, Kipp served as Vice President of Marketing at HubSpot, overseeing worldwide demand
Delian Asparouhov: Co-Founder of Varda
This week we chat with Delian Asparouhov!Delian is a Partner at Founders Fund and the President and Co-Founder of Varda Space Industries, one of the most ambitious companies redefining what’s possible in space and manufacturing. Varda is pioneering the orbital economy by producing pharmaceuticals and advanced materials in microgravity—unlocking breakthroughs that simply can’t be achieved on Earth.
Solo Episode: The Bucket Method (7-Step Time Management System)
Welcome back to Trailblazers by Park Rangers Capital!In this week’s solo episode, Erica Wenger breaks down her powerful 7-step time management framework called “The Bucket Method.”If you’ve ever felt overwhelmed, stretched too thin, or constantly busy but not actually productive, this episode is your reset. Erica walks through a simple, practical system for organizing your priorities, protecting y
Eric Newcomer: Founder of Newcomer
This week we chat with Eric Newcomer!Eric is the founder and writer behind Newcomer, which is a deeply reported newsletter on the inner workings of the startup industry. He’s widely regarded as one of the sharpest independent journalists and observers of power, money, and ambition in tech. He’s built Newcomer from a Substack newsletter into a must-read publication with over 100,000 subscribers.Aft
Jason Feifer: Editor in Chief at Entrepreneur Magazine
This week we chat with Jason Feifer! Jason is the Editor in Chief of Entrepreneur Magazine, where he’s spent nearly a decade studying and telling the stories of the world’s most successful entrepreneurs. He’s also a startup advisor, keynote speaker, and a nonstop optimism machine.He’s the author of the best-selling book Build For Tomorrow, host of the hit podcast Help Wanted with over one million
Felix Levine: Partner at Bulletpitch
This week we chat with Felix Levine!Felix is an entrepreneur, investor, and media operator who began his career in podcasting back in 2019—recording interviews straight out of his freshman-year dorm room at UC Santa Barbara.After transferring to Boston University, where he earned a dual degree in Business Law and Management, Felix spent his college years traveling the country interviewing everyon
Terri Burns: Founder of Type Capital
This week, we chat with Terri Burns! Terri is the founder of Type Capital, an early-stage venture firm focused on being the first check for ambitious founders at pre-seed and seed. Most recently, she was a partner at GV, where she made history as the firm’s youngest partner and its first-ever Black female partner, with a focus on digital consumer and emerging technology.During her time at GV, Terr
Solo Episode: 10 Pieces of Advice for Ambitious Twenty-Somethings!
Welcome back to Trailblazers by Park Rangers Capital!In this week’s solo episode, host Erica Wenger breaks down 10 pieces of advice for ambitious twenty somethings! Drawing from her personal experiences in the business world, Erica covers topics like building a strong personal brand, making smart career choices, and other key strategies for growth and success. Whether you’re just starting out or l
Shomik Ghosh: Newest Partner at Sierra Ventures!
Shomik is the newest partner at Sierra Ventures! A longtime venture investor and an inception-focused fund backing technical founders at day zero. He supported companies like Cloudquery, Kiln AI, and Ask-Y, and played a role in many other early investments.Shomik was an investor at Top Tier Capital, where he focused on growth-stage companies including CircleCI, Anaplan, Remitly, Shape Security, an
Haseeb Qureshi: Managing Partner at Dragonfly
This week we chat with Haseeb Qureshi!Haseeb is the Managing Partner at Dragonfly, a multibillion-dollar leading crypto VC firm, and is a longtime technology-focused crypto investor.He was previously a General Partner at Metastable Capital (now acquired by Dragonfly). Earlier in his career, Haseeb founded a stablecoin startup, worked as a blockchain engineer at Earn.com (acquired by Coinbase), and
Nicolas Cary: Co-Founder and Vice Chairman at Blockchain.com
This week, we chat with Nicolas Cary! Nic is the Co-Founder and Vice Chairman at Blockchain.com! He is responsible for bringing new adopters into the crypto ecosystem. A fascination with tech, money and politics led Nic to become deeply passionate about helping people reinvent their relationship with money.After an international upbringing, Nic worked as a teacher in India before becoming a foundi
Paige Finn Doherty: Founding Partner at Behind Genius Ventures
This week we chat with Paige Finn Doherty!Paige is the Founding Partner of Behind Genius Ventures, an early-stage venture firm managing nearly $14 million in AUM. Behind Genius makes concentrated investments in pre-seed and seed-stage companies led by technical storytellers across applied AI, frontier tech, and what’s next.A writer and former engineer, Paige first broke into venture capital in a t
Claire Hughes Johnson: Corporate Officer and Advisor at Stripe
This week we chat with Claire Hughes Johnson!Claire is the former COO of Stripe, where she played a critical role in scaling the company from 160 employees to more than 7,000 during its period of rapid global expansion. Before Stripe, she spent over a decade at Google, leading large international teams across multiple high-growth products and operations.She now serves on the boards of HubSpot, The
Solo Episode: 7 Things I Wish Founders Knew Before Raising Their First Check!
Welcome back to Trailblazers by Park Rangers Capital!In this week’s solo episode, host Erica Wenger breaks down 7 things she wishes every founder knew before raising their first check. The honest, unfiltered truths that can dramatically change the way you approach fundraising.Drawing from the countless lessons she’s learned while raising for her own firm, Erica unpacks the realities behind investo
Nikhil Basu Trivedi: Co-Founder & General Partner at Footwork
This week, we chat with Nikhil Basu Trivedi! Nikhil is Co-Founder & General Partner at Footwork, an early-stage focused venture firm in San Francisco. Footwork leads Seed and Series A rounds in companies with early signs of product-market fit, across both consumer technology and the consumerization of enterprise technology.The firm was founded in 2021 and is investing its second fund, with $40
Jeffrey Bussgang: GP and Co-Founder of Flybridge Capital Partners
This week, we chat with Jeffrey Bussgang! Jeff has spent his career at the intersection of startup experimentation and transformative technology. For over a decade, he has taught one of Harvard Business School’s most popular entrepreneurship courses, Launching Tech Ventures, where he's helped thousands of founders build and scale successful companies. As co-founder of Flybridge Capital Partner
Solo Episode: Starting a VC Fund 101
Welcome back to Trailblazers by Park Rangers Capital!In this week’s solo episode, host Erica Wenger dives into Starting a VC Fund 101, breaking down the real reasons why you might want to start a fund, what it actually takes to launch one, and the lessons she’s learned from being in the trenches herself.From structuring your first fund to navigating LP conversations and finding your unique edge, E
Ankur Nagpal: Founder of Carry
Ankur is a serial entrepreneur, investor, and the founder of Carry, a modern platform helping business owners build durable wealth through smarter tax strategies and long-term financial systems.He’s also the founder of Vibe Capital, a $100M venture fund backing bold founders across the U.S., India, and beyond, and the creator of Silly Money, a fast-growing newsletter and community helping people b
Amber Atherton: Partner at Patron
This week, we chat with Amber Atherton!Amber is a British entrepreneur and investor based in San Francisco. She’s a Partner at Patron, an early-stage venture capital firm shaping the future of gaming and online communities, and the Founder of The Atherton Award, which honors young women pursuing careers in STEM and entrepreneurship.A lifelong builder, Amber began coding as a kid in Hong Kong befor
Des Traynor: Co-Founder of Intercom
This week, we chat with Des Traynor! Des is the Co-founder and Chief Strategy Officer of Intercom, the company behind Fin.ai, and he also sits on Intercom’s board of directors. Over the years, Des has led teams across Product, Marketing, Customer Support, and Content, playing a key role in shaping Intercom into one of the most influential customer communication platforms in the world. Today, he ov
Amanda Goetz: Exited Founder and Author of "Toxic Grit"
This week, we chat with Amanda Goetz! Amanda Goetz is a 2x Founder, CEO and 4x CMO. She is an inspirational writer and content creator captivating millions of people every month through her social insights and newsletter “Life’s a Game”. Amanda graduated Summa Cum Laude from the University of Illinois at Urbana-Champaign and went on to lead marketing teams at Ernst & Young, The Knot and still
Rex Woodbury: Founder and Managing Partner of Daybreak!
This week, we chat with Rex Woodbury! Rex is the Founder and Managing Partner of Daybreak, an early-stage venture capital firm based in New York. Daybreak is a first-check firm built on the belief that the companies shaping the future will be those improving the lives of the next generation.Before starting Daybreak, Rex was a Partner at Index Ventures, where he invested in consumer technology and
Solo Episode: Hot Takes on Venture Capital
Welcome back to Trailblazers by Park Rangers Capital!In this week’s solo episode, host Erica Wenger shares her hot takes on venture capital the unspoken takes that many in the industry quietly know but rarely say out loud.From fundraising dynamics to investor-founder relationships, Erica unpacks the realities that shape how VC really works behind the scenes beyond the headlines and polished pitch
Avni Barman: Founder of Gen She!
This week, we chat with Avni Barman! Avni is the CEO and Founder of Gen She, a media company and fund empowering a community of over 700,000 women across Instagram, TikTok, a newsletter, a podcast, and a job board. Through Gen She, Avni writes $50K–$100K checks into ventures that directly help their audience rise to the top 1%, driving real impact for the next generation of women leaders.Before la
Solo Episode: Why Every Founder Needs to Write a Manifesto
Welcome back to Trailblazers by Park Rangers Capital!In this week’s solo episode, host Erica Wenger dives into why every founder should have a manifesto a clear, written declaration of what they stand for and where they’re headed.Erica breaks down three key benefits of writing one and walks you through five actionable steps to get started. She also makes a compelling case for the power of thoughtf
Maya Bakhai: Founder of Spice Capital!
This week, we chat with Maya Bakhai! Maya Bakhai is the founder of Spice Capital, a first-yes fund investing at pre-seed and seed. Maya's Fund II is a $25M Fund that will invest in ~40 companies with check sizes ranging from $250k-$750k. Spice Capital has over 50 companies in the portfolio including Beehiiv, MUBI, Prosper Health, Hype, Skej, and more.In the last 8 years, Maya has backed 100+ f
Katie Stanton: The Woman Behind Moxxie VC!
This week, we chat with Katie Stanton!Katie is the Founder and General Partner of Moxxie Ventures. Katie is an investor, operator, board member, and proud mom of three kids and two “poorly-trained” dogs. She has built her career leading teams at Yahoo, Google, Twitter, and Color, and also served in the Obama White House and Clinton State Department.As Founder and Managing Partner of Moxxie Venture
Ali Kriegsman: 8-Figure Exited Founder and Author of "The Raise"
This week, we chat with Ali Kriegsman! Ali is a writer, entrepreneur, and business strategist whose work lives at the intersection of brand building, storytelling, and sales. At just 24, she co-founded Bulletin, a retail technology company that reimagined how premium brands and retailers connect. Bulletin went on to be acquired by Emerald [NYSE:EEX], the largest B2B events company in the United St
Solo Episode: Trailblazers Official Launch!
Welcome to the very first episode of Trailblazers by Park Rangers Capital!In our very first episode, our host, Erica Wenger sets the stage for what’s ahead redefining what it means to be a trailblazer and introducing the bold, unconventional voices you’ll hear on this show.This is the starting point for conversations with contrarian tech leaders who challenge the norm, break barriers, and build in
Solo Episode: Season 4 Recap
This week, our host Erica Wenger wraps up an incredible Season 4 of Dear Twentysomething! 🎉Join us as we reflect on some of the most memorable guests and standout moments from the season. Erica shares her takeaways, favorite conversations, and the wisdom we’ve gathered along the way. Plus, a sneak peek at what’s in store for Season 5!Whether you’ve been with us since the beginning or just discover
Melanie Strong: Founding Partner at NEXT VENTURES
This week, we chat with Melanie Strong! Mel started her career as a first grade teacher and journalist. A fateful interview with her running hero Joan Benoit Samuelson led to a long-shot interview for an entry level job at Nike. She spent 17 years there, where she led several businesses including Nike Women and Nike Skateboarding, and worked on the launch of the Nike Running and Training Club apps
Lauren Berson-Sugarman: Founder and CEO at Conceive
This week, we chat with Lauren Berson-Sugarman! Lauren Berson is an executive turned entrepreneur with 20 years of experience building brands, products, and communities across a diverse set of industries.Lauren is the founder and CEO of Conceive, a digital health platform aiming to change fertility outcomes and experiences through community, evidence-based education, and coaching. Her focus on thi
Solo Episode: Tips for Navigating Career in Your 20s
This week, our host, Erica Wenger, shares practical and honest advice on how to navigate your career in your 20s—drawing from her own journey through college, her first job, working in VC, podcast hosting, and more!In this episode, Erica breaks down the big things that helped her build momentum early in her career—from actively absorbing information to putting herself in rooms with the right peopl
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-Rahm
TJ Taylor: Founding General Partner at Hobart Ventures
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 a
Solo Episode: Fundraising 101 for Early Stage Founders
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
Siqi Chen: Founder of Runway
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 Zyng
Troy Osinoff: Co-Founder of JUICE
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. Phi
Solo Episode: My "Getting Off The Alphabet Train" Essay Deep Dive
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 prior
Jacqueline Blackburn: Principal at Decisive Point
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
Solo Episode: Tips for Throwing a Curated Tech Event
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 forgettab
Grace Clarke: Founder of GGC Consulting
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 Direct
Eli Weiss: VP Retention Advocacy at Yotpo
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 Cu
Brett Perlmutter: Founder of Bulletpitch
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
Nihal Mehta: Founding General Partner of Eniac Ventures
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
Solo Episode: Reflections from 2024 & Hopes for 2025
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 p
Dennis Hegstad: Co-Founder of Vigilance and Internet Research Unit
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 Vi
Lisa Mayer: Founder and CEO of Boss Beauties
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
Mac Reddin: Founder and CEO of Commsor
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: TheTeaGunsCommsor: @Com
Ben Lang: Founder of next play
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 wha
Nik Sharma: CEO of Sharma Brands
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 us
Sieva Kozinsky: Founder at Enduring Ventures
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.
Liz Wessel: Partner at First Round Capital
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
Casey Lewis: Youth Trends Expert and Brand Consultant
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: @caseymlewisErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething
Solo Episode: My "Elephants in the Wild" Essay Deep Dive
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
Jason Yeh: Founder of Adamant
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
April Underwood: Co-founder and Managing Director of Adverb Ventures
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 ange
Andrew Gazdecki: Founder and CEO of Acquire.com
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: @eri
Sara Mauskopf: CEO and Co-Founder of Winnie
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 an
Steve Schlafman: Founder of Downshift
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 bei
Rachael Horwitz: Chief Marketing Officer of Haun Ventures
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 Part
Solo Episode: Welcome to Season 4!
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 transformativ
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