

Trailblazers
Erica Wenger
Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger, GP at Park Rangers Capital. Each week, Erica sits down with founders, operators, and investors who’ve found conventional success in unconventional ways.From billion-dollar exits to scrappy early pivots, Trailblazers brings you unfiltered stories of how the next generation of companies are really built. Guests share the hardest moments, the surprising wins, and the lessons that don’t make it onto LinkedIn.This podcast is presented by Brex. New episodes every Tuesday.
Episodes
Mentioned books

May 9, 2023 • 46min
Margaret Wishingrad: Founder of Three Wishes Cereal
This week we chat with the innovative and creative, Margaret Wishingrad!Margaret is the Co-founder and CEO of Three Wishes, a "healthy-while-delicious" cereal. Margaret has grown Three Wishes from an idea to a national brand, with retailers including: Whole Foods, Sprouts, Erewhon and many more. Before founding Three Wishes, Margaret was Chief of Staff at BigEyedWish, an ad-agency where she worked with Fortune 100 to seed-round startup businesses. After welcoming her first son, Ellis, Margaret discovered a space in the market for a nutritional cereal she wanted to feed her son...On this episode, the pair trace back to Margaret's upbringing as an immigrant child in Brooklyn, NY and the experiences of her youth that fostered an independence to carry her for years. Conversations on the passion for working, the intrinsic drive for success, and the make or break experiences of an entrepreneur are just the beginning!Twentysomethings, get ready for an hour with the clever, Margaret Wishingrad!Follow Us!Margaret Wishingrad: @mbwishThree Wishes: @threewishesErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

May 2, 2023 • 39min
Maika Isogawa: Founder of Webacy
This week we chat with the ambitious Maika Isagowa! Maika is the founder and CEO of Webacy, a platform for securing digital assets for the unexpected. Webacy began by exploring ways to protect blockchain-based assets with smart contracts. The team created infrastructure that could securely move assets in the event of an emergency, like death, all without the use of keys. With this foundation, Webacy began to expand into wallet safety, conditional-trigger products, and more. In this episode, the pair jump to the start of Maika’s entrepreneurial journey, uncovering the passion and drive that underlies it all. Maika is a Stanford graduate and former engineer at Microsoft who has compiled her experience and assets into the formation of her own company. Twentysomethings, if you’re looking for a motivation boost in your week, listen now to this new one hour episode featuring the ambitious Maika Isagowa!Follow Us!Maika Isogawa: @maikaisogawaWebacy: @mywebacy (and website here)Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

Apr 25, 2023 • 48min
Mady Maio, Host of "36 Questions Later," Interviews Erica
This week we chat with “36 Questions Later” Podcast host, Mady Maio.Mady is the co-founder of Camber, co-host of Okay Sis Podcast, and the host of the new video podcast series, 36 Questions Later. The series features four blind dates, where strangers ask each other the “36 questions that lead to love.” The questions date back to a 1997 study and went viral in a New York Times article. In this new series, Mady finds out how the experiment holds up today; you can follow along by checking out 36 Questions Later on YouTube, Apple Podcasts, or Spotify.In this episode, Erica switches roles from host to interviewee. Long term friends who have crossed paths in different walks of life before are rejoining again for the episode of the season! Mady mirrors the format of her “36 Questions Later” podcast this week on Dear Twentysomething as she interviews Erica. Conversations of depth and weight concerning both personal and professional thoughts, goals, and perception are all uncovered this week!! Twentysomethings, get ready for an episode like no other with this week’s swapped host, Mady Maio!Follow Us!Mady Maio: @madymaio36 Questions Later Podcast: (Youtube, Apple Podcast, and Spotify)Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

Apr 18, 2023 • 52min
Christina Wallace: Serial Entrepreneur, TED Speaker, & Author of "The Portfolio Life"
This week we chat with the successful serial entrepreneur, Christina Wallace!A self-described "human Venn diagram," Christina Wallace has crafted a career at the intersection of business, technology, and the arts. After a decade as a serial entrepreneur, she joined the faculty of Harvard Business School where she is the course head of the first-year entrepreneurship class and runs the HBS Startup Bootcamp. Her latest book is The Portfolio Life: How to Future-Proof Your Career, Avoid Burnout, and Build A Life Bigger Than Your Business Card (Hachette, April 2023).On this episode the pair go back to the start of Christina's journey and breakdown motivation and challenges along her way to success. A frequent public speaker on topics including entrepreneurship, failure, and women in tech, Christina is also known for her viral TED talk on using a sales funnel for online dating and her TEDx talk about portfolio careers and the future of work. Conversations on failure, startup businesses, and the spirit of entrepreneurship at its core is just a glimpse into this week's episode. Twentysomethings, get ready for an hour with the inspiring and creative, Christina Wallace!Follow Us!Christina Wallace: Instagram @cmwalla // Twitter @cmwallaThe Portfolio Life: (website here)Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

Apr 11, 2023 • 25min
Solo Episode: Bootstrapping vs Raising Venture Capital
This week we’re talking all about Bootstrapping vs. Raising VC Money for a start-up with our host, Erica Wenger! Having established three successful start-up businesses of her own and now entering the world of venture capital, Erica offers an inside scoop into the world of raising money for start-up businesses. While there are several different routes concerning this topic, Erica is here to share her tips, tricks, advice, and solutions with us this week! In this episode, Erica shares her experience with bootstrapping as an aid in her own start-up companies and her take on this method. While reflecting on the benefits of bootstrapping, Erica compares pros and cons to the raising venture capital method. Not only does Erica emphasize the importance of the weight that borrowed money holds, but she offers insight into the brainstorming that comes with venture capital investments. Conversation on smart profit investments, building and learning over time, and establishing the right to borrow money.Twentysomethings, if you’re starting a business and navigating bootstrapping vs. raising venture capital funds to build your business, this is the episode for you! Featuring our host, Erica Wenger!Follow Us!Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

Apr 4, 2023 • 45min
Yasmin Moaven: CMO of Pipe
This week we chat with the ambitious, Yasmin Moaven!Yasmin is the Chief Marketing Officer (CMO) of Pipe, one of the fastest growing fintech's in history. Leading all marketing, communications, partnerships, and investor-relation efforts, Yasmin builds and establishes recurring revenue as a new asset class.In this episode, Yas shares her decade of experience managing and running marketing, communications and investor relations for both publicly traded and emerging private technology companies. Prior to joining Pipe, she was one of the first employees at Fair.com, the car subscription app, spearheading investor relations, communications, and marketing, and raising over $1.4 billion in debt and $500 million in equity. Conversations on daily stoicism, University of California (USC) experiences, and her journey towards the CMO title are just the beginning. Twentysomethings, listen now for an hour with the inspiring, Yasmin Moaven!Follow Us!Yasmin Moaven: @yas_moavenPipe: @pipe (website here)Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

Mar 29, 2023 • 28min
Solo Episode: Angel vs. LP Investing 101
This week we’re talking all about Angel & Limited Partnership (LP) Investments with our host, Erica Wenger! Having worked on several successful start-up businesses of her own and now entering the world of venture capital, Erica has experienced both sides of the coin and is here to talk all about it. If you’re curious about investing your money in any capacity, this is the episode for you! In this episode, Erica breaks down the similarities and the differences between Angel (start-up business) Investing and Limited Partnership (funding) Investing. Why invest at all? How to invest? Which investments are right for you? Erica is here to answer all of these questions and more while also including us in on some tips and tricks of the trade this week.Twentysomethings, if you’re curious about financial investments and ready to have a new experince with money, listen in for an episode that has all the answers with our host, Erica Wenger!Follow Us!Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

Mar 21, 2023 • 51min
Siff Haider: Founder of Arrae
This week we chat with the ambitious, Siff Haider!Siff is an entrepreneur, host of Dear Media's The Dream Bigger Podcast and Co-Founder + CEO of Arrae, a holistic wellness brand that features 100% Naturopathic Doctor-formulated Bloat + Calm Alchemy Capsules, designed to supercharge your digestion and relax your mind. Prior to launching Arrae in March 2020, Siff spent her time in the publishing industry working for ELLE Canada, and then moved on to launch a successful blog titled Icing & Glitter, which she launched in 2016.Siff founded Arrae after struggling with many different health issues for years and found that natural remedies were able to cure many of her day-to-day issues. With that intention of bridging the gap between finding natural, organic, high-quality supplements that solved targeted problems, Siff created and expertly-formulated Arrae Bloat + Calm capsules. Arrae is the only bloat pill that has undergone 3rd party clinical trials and is beloved by celebs and influencers, such as Hailey Bieber, Melissa Wood Health, Hannah Bronfman, and more!Originally from Bangladesh, but grew up in Toronto and Dhaka, Siff graduated from the University of Toronto in 2013 and Conde Nast College in 2014. She currently resides in Los Angeles with her husband and Arrae co-founder Nish Samantray, where they spend their free time cooking, reading, and traveling the globe together. Twentysomethings, get ready for our first interview of season three with the inspiring Siff Haider!Follow Us!Siff Haider: @siffhaiderArrae: @arrae.coErica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

Mar 14, 2023 • 10min
Solo Episode: Welcome to Season 3 & Life Update
Twentysomethings, we are so excited to have you back for a third season and what better way to get started than with a solo episode with our host, Erica Wenger!In this episode, Erica reflects back throughout the seasons and touches on bits of progress and the personal growth that has been achieved since then. There is a lot of hard work going on behind the scenes, and the countdown for Erica's big announcement regarding her next business venture has begun...Dear Twentysomething is an experience-sharing platform at its core, we want to thank our listeners who have been with us on this journey from the start and also offer a warm welcome to all of our new listeners as well! We are so happy to have you guys here, listen in now for a sneak peek into Season 3 and stay tuned for new episodes every Tuesday!Follow Us!Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething

Jan 17, 2023 • 34min
Solo Episode: Season 2 Recap & Season 3 Sneak Peek
This week we’re wrapping up season 2 of your favorite podcast; bringing you a finale of reflection and excitement with our host, Erica Wenger! Highlighting some of the best moments of season 2, Erica reflects on explained episodes, special guest interviews, and her own personal growth looking back on this season! Listen in for a sneak peek on what's to come as she ventures into season 3... Twentysomethings, it's been quite the season! Be sure to follow us on Instagram for updates as we count down to Season 3 where we'll be bringing you more episodes that we hope continue to inspire and educate you as they have for us! We can't wait to have you back soon, and a special thanks to our host, Erica Wenger!Follow Us!Erica Wenger: @erica_wengerDear Twentysomething: @deartwentysomething