Portfolio Career Podcast

Two weeks after leaving his job, David and close friends have an honest conversation about navigating career transitions in real-time. From job search struggles to unexpected opportunities, this candid discussion captures the reality of being "funemployed" while friends brainstorm potential business ideas like event design and authenticity consulting.

Whether you're in transition or considering a change, this episode offers real ins...

After 4+ years as a community builder at the Chief of Staff Network, David opens up about transitioning to an advisor role. Taylor Harrington interviews him about helping build the membership-based community business mainly through events and content. His role focused on growth and member experience. David shares the emotional complexity of leaving something you're known for and how he is thinking about what is next. If you are a c...

In this episode, you will learn from Charlotte Jackson, Co-founder of the Candid card deck, Substack writer, and transitions coach, about transforming conversations through better questions. Charlotte explains why "What's the dream?" works better than "What do you do?" You will learn her “pebble vs. boulder" approach to asking specific, disarming questions that invite genuine responses rather than rehearsed answers. You will also l...

Misha Glouberman has turned his passion for bringing people together into a thriving consulting business, helping organizations transform their conferences, retreats, and gatherings into meaningful connection experiences. In this conversation, Misha shares how he evolved from co-creating the popular Toronto lecture series Trampoline Hall to building a full-time career improving corporate events. He reveals his four-step framework f...

What happens when you apply corporate strategic planning to your own life? After 12 years in finance and burning out at a high-growth startup, Michelle "Mimi" Casazza created her own strategic framework to design her dream portfolio career. What started as a two-month sailing gig turned into four years of building multiple revenue streams as a CFO consultant and executive coach. Mimi shares her "Matria Life Chart" approach to trans...

When Kevin Zych left his corporate job three years ago to become a full-time live event illustrator, he had just enough proof of concept from brand sponsorships to believe he could make it work.In this episode, Kevin shares his unconventional path from English major to Zen monk to professional street artist, revealing how he built a creative career around "reportage illustration". He discusses the practical realities of going full-...

Bart Dziedzic and Max Zucker from MrBeast's strategy team share how they went from investment banking to working at one of the world's biggest YouTube channel and media company. In this episode, you will learn their unconventional networking strategies, how LinkedIn is underrated, and the importance of adding value before asking for anything. You will also learn about community building, the creator economy's anti-establishment cul...

Are you looking to start your own thing? Listen to this episode with Tish Dignam about her journey from corporate to entrepreneurship. Tish emphasizes the importance of adopting a business owner mindset, including marketing, operations, and product development. Tish also highlights her emergent strategy for business growth, using AI tools like ChatGPT for introspection and market segmentation. She also shares her success with TikTo...

Are you looking to make work more enjoyable and meaningful? Listen to this episode with Bree Groff, the author of "Today Was Fun.” In this episode, you will hear Bree share her seven rules for better days. Bree advocates for being a "meets expectations employee and an exceeds expectations human," focusing ambition on relationships and personal fulfillment rather than solely on work success. In addition to some moments of personal s...

Are you looking into better understand yourself and the world around you? Listen to this new episode Mari Andrew about her new book, "How To Be A Living Thing," which explores lessons from animals. Mari discusses her cat Sunny, who taught her about unconditional love and autonomy. She highlights the sensitivity and emotional intelligence of horses, which mirror human emotions. Mari also reflects on rats, likening them to our societ...

Are you looking to better understand yourself and take agency of your own life more? Lawrence Yeo, in his new book called The Inner Compass, suggests to follow your inner compass more. In this episode, you learn about how to navigate the tension between certainty and curiosity when facing uncertain decision, why removing societal conditioning is essential for finding contentment, viewing uncertainty as an asset rather than a liabil...

Are you looking to stand out when building your business? Listen to this new episode with Phil and Xandie. You will learn about how Phil developed his unique selling point to clients by talking to them. You will learn about how Xandie decided to start her business and got her initial customers. You will also learn about the importance of relationships and building relationships when building your business. Excited for you to build ...

Jenny Rothenberg, Cofounder of Smooth Media, shares real strategies behind sustainable creator monetization. We dive into content-market fit—creating content your audience actually wants rather than chasing viral moments—and why events might be the most underutilized monetization strategy for creators today. Whether you're looking to monetize for the first time or diversify your income streams, this conversation offers actionable i...

Are you looking to build a service-based business? For Jess Goldberg, she initially started building her leadership and communication business on the side while working. Her clients loved her work and referrals started to come in, and keep coming in. She found even more success offering a course on Maven, and then the rest became history. In this episode, you will also learn some communication tips and frameworks. Excited for you t...

This episode was special. Chris Schembra is a really good friend. And he is a really good question asker. I wanted to share an update with you and Chris made this happen. We covered a lot of topics that I may not have talked about before. You will learn about prior life chapters and how that has helped shaped who I am today. I hope this episode is interesting to you. Please let me know what you think! Excited for you to build and g...