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 States, in a $10 million deal.Since then, Ali has helped founders and companies raise more than $20 million in venture funding, secure profitable exits, and close major sponsorship and partnership deals. She’s also the author of How to Build a Goddamn Empire, and her most recent fiction project, The Raise, which pushes the boundaries of traditional publishing by blending storytelling with cinematic, social, and direct-to-consumer elements to create an immersive brand experience.Ali has been recognized as a Forbes ‘30 Under 30’ honoree and one of Fast Company’s ‘Most Creative People in Business,’ and her work has been featured in The New York Times, The Wall Street Journal, Entrepreneur, Refinery29, The Today Show, and more✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by Gusto, OpenPhone & Athena.Gusto: gusto.com/trailblazersOpenPhone: openphone.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Ali Kriegsman: @alikriegs@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger🐘 Learn more about Park Rangers Capital!

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 unexpected ways.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by Gusto, OpenPhone & Athena.Gusto: gusto.com/trailblazersOpenPhone: openphone.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger🐘 Learn more about Park Rangers Capital!

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 discovered the show, this episode is the perfect way to celebrate how far we’ve come and where we’re headed next!Follow Us!Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

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. Mel started angel investing and advising early stage founders in 2017, and left Nike to co-found venture capital firm Next Ventures in 2019. There she's focused on innovative technology investments across health, wellness and sports in companies like Oura ring and Outside. She serves on the boards of Outdoor Afro and USA Cycling, and most weekend you can find her riding her mountain bike on the trails where she lives in Hood River Oregon.Follow Us!Melanie Strong: @girlstrongNext Ventures: @nextventuresErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

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 this problem and intention behind the company is deeply personal. She welcomed her daughter into the world after three challenging years filled with heartbreak, misinformation, and failed treatment. Conceive is the solution she wished she had. Prior to Conceive, Lauren was VP, Global Head of Strategy and M&A at WW (formerly Weight Watchers), a Senior Partner at Andreessen Horowitz (a16z), and Strategic Product Partnerships lead at Google. Lauren is an active angel investor and advisor. She also serves as a board member for the JCCA, a child welfare agency in NYC.Follow Us!Lauren Berson: @LaurenBersonConceive: @conceiveErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

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 people.Whether you're in business or not, the lessons shared here are widely applicable. Erica talks about the importance of staying curious, being proactive, and finding clarity in the midst of the uncertainty that often defines your 20s.If you're figuring out what you want to do or how to make the most of where you are, this episode is filled with real, thoughtful takeaways to help you move forward with intention.Follow Us!Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

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