Intentional Life Design and Fractional Leadership with Rebekah Rombom

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!

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 wanted to share all about it in case you want to host something like this!

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, and why every launch is a starting line, not a finish line.

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 pitching. You will also learn about Justin's "ARC" framework for structuring sponsorship packages, the value of multi-format content strategies, and how to position yourself as a consultant-like partner to brands rather than just a vendor. We also discuss Justin's upcoming "anti-conference" called Sponsor Games, designed to make creator education more hands-on and community-driven.

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 Community-Led Growth conference in March in NYC. If you are interested in CLG, we hope this conversation is helpful! 

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 connection, and about the Chief of Staff role, as Simi is a former Chief of Staff. Excited for you to build and grow your Portfolio Career! 

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-building at an AI-powered relationship management startup, and why shared interests, like running, can be a more authentic way to strengthen connections than just grabbing coffee. Excited for you to build and grow your Portfolio Career!

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. Whether you're a founder looking to grow your network or someone curious about intentional community building, you will listen this episode with Lisa!

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 say you'll do (which remains surprisingly rare). For anyone considering fractional work, she offers practical insights on being self-directed by showing up ready to onboard yourself and delivering impact without hand-holding. Key takeaway: You can design your life, most barriers are self-imposed, and authentic clarity about your priorities opens more doors than you'd expect. Excited for you to build and grow your Portfolio Career!