Why You Should Be Terminally IRL with Ben Winn

Ben Winn, VP Community and Content, makes the case for going "terminally IRL." As AI floods the internet with slop and bots overtake human traffic, he argues the real edge is showing up in person. He breaks down how to spot quality events, why brevity wins in outreach, and why he wants to get on a texting basis with more people.

Annie Riley, CEO of Fort Light and Host of the Best Manager Ever podcast, talks about the vulnerability of putting yourself out there while building a business tied to your identity. You will also learn about a breakthrough blizzard video to rehabbing the word "manager" and choosing real over polished. You will also learn about how she bought the Fort Light business. Enjoy!

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!