Portfolio Career Podcast

The Community Led Growth "CLG" Conference on October 2nd 2026 was a big success. We had an over 95%+ attendance rate and got lots of great feedback. In this episode, we share our reflections right after the conference while it is fresh. You will learn about how CLG2 compared to CLG1 earlier this year as well. Enjoy and happy hosting!

Where you host an event matters. The people who attend are very important, but where you host matters too. Zach, Ruthie and David talk about venue selection for events and how they decided to pick Fabrik as the venue for The Community Led Growth conference on Friday October 2nd. They all are Founding Members and have hosted a bunch of events at Fabrik. You will also learn behind the scenes informa...

David Nebinski, Founder of A Chief of Staff, is interviewed by Kriti and Andrew who have attended his A Chief of Staff Mixers about starting and building A Chief of Staff. In this episode, you will learn about David’s prior Chief of Staff-like roles, his solopreneurship journey, and the starting the A Chief of Staff community and events in New York. This episode was originally published on the A C...

David reflects on how Community-Led Growth Conference 2 (CLG2) came together — from a spontaneous catch-up call with Ruthie Berber to Zach Hawtoff's immediate "let's do it" — and why he keeps coming back to the idea of compounding: building on projects, relationships, and momentum instead of starting from scratch each time. CLG2 happens October 2 in New York at Fabrik. More info at luma.com/clg2.

Cristina Ciaravalli, Founder and CEO of Valli Ventures, shares about building a community-first business — from fitness-focused Founder events to a growing recruiting and advisory practice. She shares how her recruiting arm grew out of casual favors for friends, what it took to scale from a solo operation to a team of seven, and about the flywheel she has built that fuels everything.

Melissa Wong returns five years after her first appearance to talk about her new book, The Fluid Career . She and David dig into why multi-hyphenates and portfolio careerists are best positioned to weather AI-driven job anxiety. They also reflect on David's own career transition over the past year. Enjoy!

An audit can be much more than an assessment, it can be the beginning of a great conversation. This episode explores how providing business owners with an audit creates something tangible to discuss, encourages collaboration, and helps uncover opportunities together. I did this last summer when I was transitioning, wanted momentum, and it went better than expected. Learn all about it here.

Taking chances can change the direction of our lives. In this episode, multiple voices share their perspectives on taking risks, embracing uncertainty, and saying yes to opportunities, even when you don’t know exactly where they’ll lead.

When I use social media, I am often projecting something. A story. A message. An event. Something. And at the same time, there is a lot more going on in my life that I often do not post about, or know where or how to do so. Insert: a Now page. It is a page on my website that I can communicate what is holistically top of mind to me. It is very handy when communicating with people digitally too. Lea...

Olivia Leavengood shares her journey from full-time Chief of Staff to bootstrapped Founder to fractional chief of staff, and she's now niched down into helping B2B founders master founder-led sales. She breaks down why niching down is key to building a fractional or consulting practice, why warm referrals drive most early-stage B2B sales, and how AI is shifting where founders should spend their sc...

In this episode, Nkem Oghedo and David Nebinski talk Chief of Staff transitions, the "identity economy," and why leaning into the unknown beats chasing certainty. Nkem shares the news that she's stepping away from fractional work to go full-time with one of her clients, and what that means for her portfolio career going forward.

Natalie Trotta used to be a Chief of Staff. Now she is building her own consulting business. She started off calling it fractional work and now it has grown. You will learn about how she positions herself, how she has found clients, the importance of conversation, and much more. If you are a Chief of Staff thinking about what is next or wanting to start doing consulting or fractional work, this ep...

In this episode, you will learn about how I am building my portfolio career, how it compares to the prior quarter and what I have learned through this. You will learn about what has been energizing me in my work and how I enjoy work that is compounding and growing. I also talk about a new project and what stood out to me about it. Enjoy!

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!