Charlie O'Donnell on Building Trust and Relationships

Grace Clarke went viral for her annual planning template, then left her job, moved, and became a teacher running AI for Normal People classes in NYC. She and David talk about why your plan should go off the rails, building your own AI "board of directors," and the messy open questions about personal IP, jobs, and what it means to own your career in the age of AI.

Charlie O'Donnell, a 20+ year NYC tech venture veteran and author of Founder Unfriendly, joins David to talk about the art of staying genuinely connected. They dig into "heartbeat emails," why trust is really just information, and how showing up as a three-dimensional person (not just a LinkedIn profile) is the real secret to fundraising, career growth, and community building. Charlie shares community building tips as well! Enjoy!

What if you took your time and built a business at your own pace? That's what Brian Helfman, the Founder of Third Nature has been doing. He has been building his Adult Summer Camp business for 10+ years. He is building this in addition to working on other things. He is also a recent father as well, and you will learn about how he thinks about work as a Dad now. If you are a community builder, this episode is for you!

Tarlon Khoubyari, San Francisco Events & Community Lead at Rho, shares how she approaches events as a product — iterating on formats, curating rooms intentionally, and turning in-person gatherings into a real revenue driver for her company. If you are a community builder or want to build community, this episode is for you!

Hannah Zhang is building a “5-to-9” business alongside her day job at a startup. In two years, she has built a six-figure business as a creator. She has over 170,000 followers on Instagram and writes a newsletter. In this episode, you learn about why nonlinear careers are the future, structuring brand partnerships, and the importance of creating a direct relationship with your audience with something like a newsletter. Excited for you to build and grow your Portfolio Career!

Ben Bradbury, Co-founder and CEO of Reading Rhythms, returns to share how a rooftop book reading event with 10 friends became a thriving community business with nearly 700 reading parties around the world. We cover brand partnerships, community building strategy, and their new app, and much more! If you are looking to build a community-based business, this episode is for you!

Clare Purvis, the Founder of WELL, a community for women in digital health, joins the show to discuss how she pulled off her first-ever ticketed Summit. The conference had 70+ women and was focused on peer-to-peer learning. She built the conference similar to the programming in her online accelerator program. Clare has been building her business for a few years. If you're building a community business or thinking about hosting your first big in-person event, this episode is for you.

LinkedIn strategist and community builder Molly Godfrey shares how she's generated $5M for clients using LinkedIn. She shares what types of posts actually work, how to think about top vs. bottom of funnel content, and why consistency (not perfection) is the key to building a business and brand on the platform. Enjoy!

Nicole Kelner shares how a Substack post about finding quiet in NYC became a Rizzoli book deal called Quietest Places in New York City. You will learn more about the book and the ideas in it, in this episode. You will also learn about Nicole built a habit-tracking app called Free Time recently too. She is taking action on her ideas and you can too!

Are you looking to be more self-employed or self-funded? Listen to this episode where I talk about how my portfolio career has evolved over the last six months of working on my own. I am currently kind of paralell pathing two similar work streams. You will learn about the two, three month chapters and how things feel more durable and compounding now compared to a few months ago. Hosting events, connecting with friends, and loose ties have all been helpful too. Thank you for being part of this journey! Excited for you to build and grow your Portfolio Career!