Portfolio Career Podcast

Neil Yeoh, Founder and CEO of OnePointFive, shares lessons on bootstrapping his company through six brutal years to build a 20-person team and and his community-led growth playbook of flywheels, LinkedIn, and building a minimum viable audience along the way. Enjoy!

Are you building a company, community, or a movement? What have you learned? In this Hot Pod podcast mixer episode, you will hear from a handful Founders and Community Builders about lessons from building their project, movement and /or company. You will learn about tactical approaches and mindset approaches well. Enjoy!

Olivia O'Sullivan, Partner & COO at Forum Ventures, joins David Nebinski to talk community-led growth: why community roles are so hard to get buy-in for, how to translate "soft" community metrics into the numbers leaders actually care about, and how Founders are thinking about community-led growth in 2026. If you are a community builder or Founder, this episode is for you!

Carly Cassidy thinks a lot about friendship. She has a podcast called Core Friends and wants to have a group of core friends herself and cultivate close friendships. In New York and maybe other cities, this is hard. She wrote a Substack post about this topic. While being a soloprenuer, I have been thinking more about friendship and wanted to talk with Carly about this. You will learn about both of...

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 comm...

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...

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 someth...

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 busi...

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, co...

I cohosted the first-ever Community Led Growth Conference (CLG) with Zach Hawtof on Friday March 13th. On Monday March 16th, we chatted about it in this podcast episode. We talked about how the conference came together in two months, how it was sold-out, our programming choices, and how a few serendipitous things came together for the conference to happen. The conference was a big success and we w...

Avital Knoller is the Head of Ecosystem at Orchid Security. In this episode, she shares her 10 years of hard-won community building wisdom. You will learn about growing Wiz's community to a Google-acquisition exit, B2B community building, and why she believes we're in the golden age of community building.

Miri Buckland never planned to be a Founder, until a Stanford class project turned into Landing, a social app that grew to over a million downloads without spending a dollar on marketing. After six years of pivots, community building, and ultimately shutting it down, she's back at zero-to-one with Extra, a new email app launching this spring. We talk community-led growth, committing to the pivot,...

In this episode, I talk with Justin Moore, the author of Sponsor Magnet , about how creators can successfully land and manage brand sponsorships. Justin shares insights from his experience running sponsorship challenges and coaching creators, emphasizing that mindset, particularly overcoming money-related fears and childhood financial baggage, is often a bigger barrier than the tactical side of pi...

What does community-led growth look like? A group of founders, marketers, and community builders unpack community-led growth from every angle: why human connection beats performance marketing, how communities create multiple business entry points, and why earning organic growth is slow but worth it. Zach Hawtof, the Founder of Tightknit, and I cohosted this podcast mixer in advance of the Communit...

Simi Shah, the Founder of South Asian Trailblazers, shares how she turned a pandemic-era podcast into a thriving community with live podcast events. Simi shares how she also discovered her "reverse product-market fit” with her agency when people asked her for media strategy advice. You will also learn about personal branding fundamentals, why storytelling is ultimately about empathy and human conn...

Alex Chung, Founding Head of Growth at Goodword, shares her approach to building meaningful professional relationships. She discusses the power of follow-up and follow-through, how she connected with entrepreneur Andy Dunn by offering value first, and why being "a little unhinged" is sometimes necessary to make things happen. Alex also talks about her role blending marketing, sales, and community-...

Lisa Skye is the Founder of SkyeCo and is a prolific community builder. In this episode, she shares her unconventional path from BNI chapter President, to WeWork early employee, to launching SkyeCo, a structured networking community for mostly for business owners. Lisa discusses the outsized impact of being "dangerously consistent” and the benefits of consistently showing up in networking groups....

Rebekah Rombom shares how she transitioned from a nearly decade-long role at Flatiron School to building a fractional executive practice—not by design, but by staying busy with consulting until she realized she didn't need a traditional job. Rebekah emphasizes two powerful principles: clearly articulating what you actually want (so people can help you get there), and consistently doing what you sa...