Are you looking to know what is like to find work you want to do? Paul Millerd is the author of The Pathless Path and Good Work. In this episode, he talks about the art of staying in the game without chasing metrics, how to think about work without letting it define your identity, and a framework for designing dream projects that actually fit your life. You will also learn about podcasting on your own terms, curiosity conversations, and the importance of creating a new narrative when thinking about leaving a job. Excited for you to build and grow your Portfolio Career!

Carly Valancy, the Founder of The Reach Out Party, believes that you should take more agency over the people who are in your life. In this episode, she shares practical strategies for reaching out to people you admire and building sustainable connection habits. She thinks that networking doesn't have to feel icky when you do it your way. In this episode, you will also learn about the successful Anti-Networking Party that she recently hosted in New York City. You will also learn the highs and lows of hosting events. Excited for you to build and grow your Portfolio Career!

What is your definition of leadership? In this episode, Stephen Shedletzky also known as "Shed" shared his definition of leadership and asked for feedback from other people attending this Podcast Mixer event. You will hear about whether leaders are necessary, challenge conventional definitions of leadership, and discuss the balance between charisma and quiet leadership. If you are interested in leadership, this episode is for you. Excited for you to build and grow your Portfolio Career!

Ashwini Anburajan shares her journey from Chief Revenue Officer to CEO at Obi, a rideshare aggregator app. In this live episode recorded in New York City, Ashwini discusses the critical first 90 days of her new role, why the company pivoted before, and the challenges of scaling a startup. She also reveals why she's hiring a Chief of Staff , so that she can focus on revenue growth and product development. Whether you're interested in startup leadership transitions, transportation tech, or Chief of Staff roles, this conversation offers practical insights on career growth and company building.

Rina and David candidly discuss their parallel career transitions and the unexpected ways they've supported each other through the uncertainty. Rina shares her journey from leaving her first 9-to-5 role to launching a daily TikTok practice that unexpectedly built community and income. Together, they explore the difference between chasing opportunities that fall into your lap versus pursuing the dreams that truly scare you, the power of accountability partnerships during transitions, and why doing the thing you've been putting off might be exactly what you need. If you're navigating a career change and feeling alone, this conversation will remind you that transitions take time and you don't have to do it alone.

Erica Akitani-Bob is currently the Chief of Staff at All Places. This is not her first Chief of Staff role. In this episode, you will learn about how she got her current role, advice for job seekers, how she adds value in the role, and how she tries to understand the scope of projects. This episode was recorded at an event in NYC. During the episode, you will questions from people attending the event. If you are looking for a Chief of Staff role or how to become a better one, this episode is for you!

Will Mannon and I have a shared passion for bringing like-minded people together in-person. The conversations can be incredible and wildly generative. Will was the Cofounder of Write of Passage, a popular online writing school. Through the course, he hosted a bunch of in-person meetups. In 2025, he cofounded another company called Act Two. Connected to this company, he hosted a bunch of meetups around the world during the summer of 2025. After partnering on an event in Brooklyn, we decided to partner together on the Internet Serendipity World Tour powered by Circle in late 2025. Learn about how and where we are bringing in-person events and connection around the world in 2025!

Al Simon shares his journey from selling his prior company, Elude, to launching The Lab, a creative agency helping pre-seed and seed-stage founders with pitch decks and fundraising. Al discusses the power of network building, his philosophy on staying in touch with people, and why 90% of his 90+ clients came through word of mouth. The conversation also touches on his passion for travel, focusing on happiness, and his upcoming non-alcoholic beer brand. Excited for you to build and grow your Portfolio Career!

Morgan Brady, the Director of Community at Inc. and Fast Company, shares insights from her 10+ years building communities for entrepreneurs. She discusses the power of text message retention, hosting a 10-event road show, and why creating pre-conference connections helps introverts thrive at larger events. Morgan reveals her strategies for convincing busy founders that community is worth their time and emphasizes that transformative relationships, not just business connections, are what make community building meaningful. Excited for you to build and grow your Portfolio Career!

Zach Hughes, a Partner at Ascendancy, shares how he built a business around strategic relationship-building. From leaving consulting after reading "The 4-Hour Workweek" to creating "winfinity" partnerships where everyone wins, Zach reveals practical strategies for leveraging relationships to accelerate your career. In this episode, you will learn about why business success ultimately comes down to relationships and story, how to "punch above your weight" through warm introductions, and starting small with 5 key relationships to improve the strength of your network. Excited for you to build and grow your Portfolio Career!

Are you looking to level-up your events? Here are seven ways that I usually apply to my events. Hosting events has changed my life and hopefully these ways and tips help you and your events!

Yael Shemer was a community builder before she cofounded TULU. In this episode, she shares how she built her real estate tech startup from three buildings to over 400 globally in seven years. She discusses pivoting from B2C to B2B and managing the chaos of rapid scaling. You will also learn about her unconventional journey from environmental activist and waitress to tech founder, learning to leverage her authenticity and community organizing skills as strengths rather than viewing them as limitations.

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 insights about embracing uncertainty and finding support during life's biggest shifts.

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 community builder, looking to work in the field, or thinking about a work transition, this episode is for you.

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 learn about finding conversational "trailheads" and how intentional questions can deepen relationships and self-understanding. Excited for you to build and grow your Portfolio Career!

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 for successful events (starting with having a clear goal), explains practical techniques like helping attendees find their conversation partners, and discusses why most event organizers focus on entertainment instead of connection. Misha also opens up about overcoming the common aversion to sales that many community-focused professionals face. If you are looking to have a career in events and community building, this episode is for you!

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 transitioning from corporate burnout to purposeful portfolio living. Whether you're stuck in corporate or already building a portfolio career, this episode shows how strategic thinking can help you design a life you actually want to live.

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-time creative without a plan, why he believes art creates human connection, and how his time as a Zen monastic shaped his philosophy of embracing risk and immediacy in both art and career decisions and much more.

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 culture, and why 1,000 true fans beat 10 million passive followers. If you are looking into working at creator companies or transform their career through authentic relationship building, this episode is for you!

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 TikTok, which has generated significant inbound leads. Tish's business has evolved from brand marketing coaching to clarity coaching, driven by client referrals and her ability to help founders communicate effectively. If you are looking to start your own service-based business, this episode is for you!