Portfolio Career Podcast

In this episode, you will learn from Charlotte Jackson, Co-founder of the Candid card deck, Substack writer, and transitions coach, about transforming conversations through better questions. Charlotte explains why "What's the dream?" works better than "What do you do?" You will learn her “pebble vs. boulder" approach to asking specific, disarming questions that invite genuine responses rather than rehearsed answers. You will also learn about finding conversational "trailheads" and how intentional questions can deepen relationships and self-understanding. Excited for you to build and grow your Portfolio Career!

Misha Glouberman has turned his passion for bringing people together into a thriving consulting business, helping organizations transform their conferences, retreats, and gatherings into meaningful connection experiences. In this conversation, Misha shares how he evolved from co-creating the popular Toronto lecture series Trampoline Hall to building a full-time career improving corporate events. He reveals his four-step framework for successful events (starting with having a clear goal), explains practical techniques like helping attendees find their conversation partners, and discusses why most event organizers focus on entertainment instead of connection. Misha also opens up about overcoming the common aversion to sales that many community-focused professionals face. If you are looking to have a career in events and community building, this episode is for you!

What happens when you apply corporate strategic planning to your own life? After 12 years in finance and burning out at a high-growth startup, Michelle "Mimi" Casazza created her own strategic framework to design her dream portfolio career. What started as a two-month sailing gig turned into four years of building multiple revenue streams as a CFO consultant and executive coach. Mimi shares her "Matria Life Chart" approach to transitioning from corporate burnout to purposeful portfolio living. Whether you're stuck in corporate or already building a portfolio career, this episode shows how strategic thinking can help you design a life you actually want to live.

When Kevin Zych left his corporate job three years ago to become a full-time live event illustrator, he had just enough proof of concept from brand sponsorships to believe he could make it work.In this episode, Kevin shares his unconventional path from English major to Zen monk to professional street artist, revealing how he built a creative career around "reportage illustration". He discusses the practical realities of going full-time creative without a plan, why he believes art creates human connection, and how his time as a Zen monastic shaped his philosophy of embracing risk and immediacy in both art and career decisions and much more.

Bart Dziedzic and Max Zucker from MrBeast's strategy team share how they went from investment banking to working at one of the world's biggest YouTube channel and media company. In this episode, you will learn their unconventional networking strategies, how LinkedIn is underrated, and the importance of adding value before asking for anything. You will also learn about community building, the creator economy's anti-establishment culture, and why 1,000 true fans beat 10 million passive followers. If you are looking into working at creator companies or transform their career through authentic relationship building, this episode is for you!

Are you looking to start your own thing? Listen to this episode with Tish Dignam about her journey from corporate to entrepreneurship. Tish emphasizes the importance of adopting a business owner mindset, including marketing, operations, and product development. Tish also highlights her emergent strategy for business growth, using AI tools like ChatGPT for introspection and market segmentation. She also shares her success with TikTok, which has generated significant inbound leads. Tish's business has evolved from brand marketing coaching to clarity coaching, driven by client referrals and her ability to help founders communicate effectively. If you are looking to start your own service-based business, this episode is for you!

In a world that often feels chaotic and uncertain, how do we discover what truly matters? In this Hot Pod event episode, you will hear stories about people have been finding meaning through learning, community, service, and more. Whether you're navigating a major life transition or simply seeking deeper satisfaction, this conversation offers insights and ideas for you to hopefully find more meaning.

Are you looking to make work more enjoyable and meaningful? Listen to this episode with Bree Groff, the author of "Today Was Fun.” In this episode, you will hear Bree share her seven rules for better days. Bree advocates for being a "meets expectations employee and an exceeds expectations human," focusing ambition on relationships and personal fulfillment rather than solely on work success. In addition to some moments of personal stories, this episode concludes with Groff's daily journal prompt: asking "Was today fun?" and identifying one moment of joy, even on difficult days, as a way to actively seek and appreciate the happiness available in everyday life. Excited for you to build and grow your Portfolio Career!

Are you looking into better understand yourself and the world around you? Listen to this new episode Mari Andrew about her new book, "How To Be A Living Thing," which explores lessons from animals. Mari discusses her cat Sunny, who taught her about unconditional love and autonomy. She highlights the sensitivity and emotional intelligence of horses, which mirror human emotions. Mari also reflects on rats, likening them to our societal shadows. She emphasizes the importance of embodiment and intuition, drawing parallels between human and animal behavior. She also touches on the connection between pregnancy and creativity, advocating for a devotion to embodiment. Here we go with Mari!Read Mari's book

Hosting good events is a life hack. You can meet incredible people, build your network, have fun, etc! In this episode, I detailed 7 tips for hosting a great event. After that, I shared about the events I have hosted since 2022 and what I have learned from them. Excited for you to build and grow your portfolio career! Happy hosting!

Are you looking to better understand yourself and take agency of your own life more? Lawrence Yeo, in his new book called The Inner Compass, suggests to follow your inner compass more. In this episode, you learn about how to navigate the tension between certainty and curiosity when facing uncertain decision, why removing societal conditioning is essential for finding contentment, viewing uncertainty as an asset rather than a liability, and the benefits of journaling. Excited for you to build and grow your Portfolio Career!You can pre-order the book, The Inner Compass, here!

Are you looking to stand out when building your business? Listen to this new episode with Phil and Xandie. You will learn about how Phil developed his unique selling point to clients by talking to them. You will learn about how Xandie decided to start her business and got her initial customers. You will also learn about the importance of relationships and building relationships when building your business. Excited for you to build and grow your Portfolio Career!

Jenny Rothenberg, Cofounder of Smooth Media, shares real strategies behind sustainable creator monetization. We dive into content-market fit—creating content your audience actually wants rather than chasing viral moments—and why events might be the most underutilized monetization strategy for creators today. Whether you're looking to monetize for the first time or diversify your income streams, this conversation offers actionable insights you can implement immediately.

Are you looking to date? Listen to this Podcast Mixer episode where three people share their stories, experiences, and interests on dating. There is a common theme around the importance of friendship and maintaining a friendship while dating. If you are interested in dating, this episode is for you!

Are you looking to date or find a partner? If so, how are you thinking about it? Ben Von Wong has created a dating framework to help him think about dating. In this episode, you will learn about the framework and the reasons why he created it. You will also learn about the importance of friendship and clear communication in dating.

Are you looking to build a service-based business? For Jess Goldberg, she initially started building her leadership and communication business on the side while working. Her clients loved her work and referrals started to come in, and keep coming in. She found even more success offering a course on Maven, and then the rest became history. In this episode, you will also learn some communication tips and frameworks. Excited for you to build and grow your Portfolio Career!Connect with Jess on LinkedIn!

This episode was special. Chris Schembra is a really good friend. And he is a really good question asker. I wanted to share an update with you and Chris made this happen. We covered a lot of topics that I may not have talked about before. You will learn about prior life chapters and how that has helped shaped who I am today. I hope this episode is interesting to you. Please let me know what you think! Excited for you to build and grow your Portfolio Career!

Are you looking to host dinner parties? Saba Ahmed is the Cofounder of Tiny Dinner, a company that hosts dinner parties in homes. In this episode, you will learn about how many people is good for a dinner party, the importance of curating an attendee list, where dinner parties should be held and so much more! Excited for you to build and grow your Portfolio Career!Connect with Saba on InstagramConnect with David on Instagram

Have you ever been frustrated with a situation? Amanda Pena, creator of The Rules of 30 Instagram account with over 130,000 followers, turned her frustration into impact. Amanda's account went viral, resonating with many women in their 30s. In this episode, you will hear more about her spiky point of view on societal pressures and the benefits of delaying life milestones, and much more. Excited for you to build and grow your Portfolio Career!Follow The Rules of 30 Instagram account hereFollow David's Instagram account here

Are you looking to level-up your life? Listen to this episode to hear Life Hacks from the three people. This episode was recorded at the Life Hacks mini-conference. You will learn about tech tools, ways to improve your email outreach, and so much more! Tune to level-up!

In this episode, we explore the creative process from initial spark to finished work. Discover how creators across all disciplines develop their ideas, use AI, balance structure with spontaneity, and develop resilience. Whether you're a seasoned artist or just beginning your creative journey, join us for practical insights on transforming your ideas into art. This episode was recorded during a Hot Pod Podcast Mixer with 8 or so people. Excited for you to build and grow your Portfolio Career!

Valerie Chapman shares her journey from being laid off twice to becoming a LinkedIn creator, achieving over 120 million impressions in 90 days. Valerie shared how she is leveraging AI to build powerful personal brands on LinkedIn. She also often posts about AI on LinkedIn, and how she saw a gap in the market to do so. Valerie also stresses the need for people to use AI for strategic planning and to brainstorm a bigger life for themselves. If you are looking to level-up and learn about AI, cold email, creating content and video content and more, this episode is for you!Connect with Valerie on LinkedInConnect with David on LinkedIn

Bethany Crystal discusses her transition from a fractional worker to an AI founder. She shares her experience of using AI often in her role at a dev shop and how it saved her life during a near-death experience. Bethany highlights her new app, MuseKat, designed to help parents explain museum exhibits to their kids using AI-generated audio stories. Bethany also reflects on the evolving job market and the need for individuals to adapt and leverage AI tools to stay relevant. She shared how she is building this app as a way of creating a container that works for and excites her while wanting to be part of the growing AI sector. Excited for you to build and grow your Portfolio Career!Connect with Bethany on TwitterConnect with David on Twitter

Can our thoughts truly shape our reality? In this episode, we explore manifestation through many different lenses. Is it the same as goals or something else? In this episode, you will hear 7-8 people discuss this and more. Tune in and maybe you will manifest something :)Connect with David on Instagram!

In this episode, you will hear from Wen-Jay Ying, Founder of Local Roots, a modern CSA that recently ended its core operations after 14 years. Wen-Jay discusses her journey, starting from her passion for local food and her decision to create a business that supports organic and sustainably grown ingredients. She highlights the challenges faced during the pandemic, including increased demand and operational stress. Despite the success, Wen-Jay decided to pivot and is now focused on new business ideas. If you are looking to pivot or start a new chapter, this episode is for you!Connect with David on InstagramConnect with Wen-Jay on Instagram

Are you looking to grow your impact, influence and income? This episode was recorded during the Strategic Storytelling Summit that I cohosted with Terry Rice. In this episode, you will hear three people share about how they are using stories and storytelling as a way to grow. For many of us, telling our story is very important. Listen to this episode to hear about how three people tell their story and more! Excited for you to build and grow your Portfolio Career!Connect with me on IGLearn more on my Substack

In this episode, we dive into the power of collaboration and how communities have grown through with other organizations and communities. During this Podcast Mixer episode, you will hear multiple stories from people sharing real-world stories, practical strategies, and lessons learned. This conversation will give you valuable insights on building and sparking meaningful connections and amplifying your impact. Tune in and discover how working together can make our communities stronger!Let's connect on InstagramLearn more about my work on Substack!

When was the last time you had a hard conversation? What did you learn from it? What did you wish you would've done differently. In this episode, you will hear stories about people having a hard conversation. I hope this episode makes future hard conversations easier. Excited for you to build and grow your Portfolio Career!

In this episode, you will learn from Anne-Laure Le Cunff, Founder of Ness Labs and the author of a new book called Tiny Experiments, about the power of personal experimentation. Anne-Laure shares how she crafted an experiment to write a book on experiments, and explains practical methods for designing your own life experiments. She emphasizes the importance of setting deadlines and embracing uncertainty. She also touches on the emotional aspects of letting go of desired outcomes and her own definition of success. Excited for you to build and grow your Portfolio Career!Learn more about the book Tiny ExperimentsConnect with Anne-Laure on Instagram!Connect with David on Instagram!

Do you know your enneagram type? Have you ever considered how your type impacts your connect with other people. In this episode, Jon Wu talks about the enneagram personality test, why he loves it, and how it can help you better understand yourself. In this episode, we talk about our enneagram types and how they show up in the world, and how to potentially navigate hard conversations. If you are looking for a way to better understand yourself and your relationships, this episode is for you!Connect with Jon on TwitterConnect with David on Twitter

Have you ever made a mistake? Probably, right? Building community is hard and mistakes happen. Listen to this episode where 10 or so community builders shared stories of mistakes, learnings, and how they are thinking about these situations now. Maybe if you aren't making mistakes, you aren't trying hard enough. Excited for you to build and grow your Portfolio Career!

Are you looking to building a community-focused business? Listen to this episode with Emily Chertow, the Founder or Journaling Classes. She has been hosting journaling classes for over 6 years. Since early 2024, she has been full-time on building her business. In this episode, you will hear about starting her community, inflections, and learnings from going full-time. Excited for you to build and grow your Portfolio Career!Learn more about Journaling Classes!Learn more about me!

What does it mean to live an A+ life? Katy Atherholt and I both explored this topic and chatted about it in this podcast episode. After a separate conversation, we both decided to write an essay on this topic and then we discussed it on this podcast. Interestingly, we both had different points of view and could see each other's prospective. Your point of view is likely different too, which is amazing. When you know what A+ looks like, hopefully it means it is easier to live it.Connect with Katy on TwitterConnect with David on Twitter

Kameron Monet is an attorney, content creator, and entrepreneur with over 60,000 Instagram followers and nearly 100,000 YouTube subscribers. She began creating YouTube videos in 2014, initially for fun, and later monetized her content. Kameron posted videos while she had a traditional job as a lawyer and many of them became very popular. She talked about leaving her job, becoming a consultant, and now how she works on her own as a lawyer for content creators. In this episode, you will learn about the power of niche content and how it only takes one video to change your life. We also talked using YouTube and Instagram stories to create community and more. Excited for you to build and grow your Portfolio Career!Learn more from Kameron on InstagramLearn more from David on Instagram

Join us as we explore the art of bouncing back from life's challenges in this powerful episode. This episode was recorded among 8 or so people at a dinner table. You will hear stories from people who turned their setbacks into springboards for growth and learnings. Whether you're dealing with career hurdles, personal struggles, or unexpected detours, this conversation offers valuable insights to help you not just recover, but emerge stronger from life's setbacks.Connect with David on InstagramRead my newsletter here!

In this episode, meet Remington Davenport, who left her career in sales to pursue her passion: creating the world’s backgammon club in NYC with the NYC Backgammon Club. Remington shares how she moved to NYC and didn’t see any backgammon events that really resonated with her - so she started hosting her own. The word began to spread, and her events started growing in popularity and frequency. So, she decided to go full-time on this. You will learn about her decision to do this, about partnering with venues, and what she has noticed about building her community and more. If you are interested in community building or following your passion, this episode is for you.Learn more about the NYC Backgammon ClubConnect with David on Instagram

Did you build community in 2024? How are you thinking about it in 2025? In this episode Veronica Kaulinis, the Founder of Vulnerable AF, and I discuss the answer to these questions and more. You will learn about the momentum of hosting good events, the benefits of curation, why more time spent upfront is helpful later on, and so much more. If you are interested in community building, this episode for you!Connect with Veronica on IGConnect with David on IG

Are you looking to work professionally as a community builder? Listen to this episode with Jessica Lowenstein who has been working professionally in the field since 2016. She is currently Head of Community and Events at Hampton, a community for founders and CEOs. She has had numerous other community roles. In this episode, you will learn about how the profession has evolved, what she loves about the work, what she looks for when hiring for community roles, and what Hampton's community team looks like. Excited for you to build and grow your Portfolio Career!Connect with Jess on LinkedIn!Connect with David on LinkedIn!

Are you a community builder looking to build a portfolio career? Listen to this podcast episode with Mallory Contois, the Founder of the Old Girls Club (OGC) and Head of Community at Mercury. In this episode, you will learn how Mallory launched OGC and how she built it to be async-focused and how it was helpful for her to get her current role. Mallory is also passionate about portfolio careers and emphasizes the importance of having a clear investment thesis to guide career decisions and advocates for monetizing passions. Excited for you to build and grow your Portfolio Career!Connect with Mallory on LinkedInConnect with David on LinkedIn

What are you excited about? What are you inspired by? Hearing stories about these two topics.... can be inspiring! For episode 350, I hosted an event and invited people to share these stories. Thank you for being part of my podcasting journey, even if this is just for your first episode. Excited for you to build and grow your Portfolio Career!Connect with David on InstagramLearn more in my newsletter

Yena Kim has built the Menswear Dog brand and business for 10+ years, which is crazy and inspiring to think about. You will learn about how her dog, Bodi, first went viral and then how Yena quickly responded on this fame through partnerships and more. In this episode, you will learn about working on things you love, making it easier to work with press, how the creator economy is growing, why online marketing on your own is becoming increasingly important. Unfortunately, Bodi passed away a few days before this podcast recording and Yena talks a little bit about this. This was a special and powerful episode and I hope you enjoy it!Learn more about Meanswear Dog on IGConnect with David on IG

Are you looking to build community? Jaclyn Pascocello is the Founder of Fabrik, a home for community builders. They currently have a physical space open in Tribeca for community builders to host gatherings. I am a member and have hosted a few events there. In this episode, we talk about launching Fabrik, event insights for community builders, and so much more!Connect with Jaclyn on LinkedInConnect with David on LinkedIn

Are you looking to live a life with relationships and friendships at the center of it? In this episode, my good friend Lani Assaf and I walked and talked about our lives and how we are both living like this. We also talked about the challenges and joys of maintaining friendships, the impact of working remotely, and the need for spontaneity and intentionality. Lani emphasized the value of containers for freedom, joy, and play, while I highlighted the significance of repeated interactions and shared experiences. We both reflect on the changing seasons and their impact on their lives, and what else has been on our minds living in Brooklyn. Hope you enjoy it!Connect with Lani on InstagramConnect with me on Instagram

Are you looking to build or grow a community? Listen to these 5 hot takes from community builders. These mini-clips were recorded at my Community Builders and Creators mini conference aka C3 in November. If you are interested in community building, this episode is for you!Connect with me on InstagramLearn more in my newsletter

In this episode, you will hear stories of when people were scared and afraid of something. Through inspiring stories, actionable tips, and a few laughs along the way, we’ll show you how to be scared and brave —at the same time. Whether you’re facing a career pivot, a big life decision, or just a new personal challenge, this episode will give you the tools to push past your fear and go for it anyways.Connect with David on InstagramRead David's newsletter

What does it mean to truly feel alive? In this episode, we dive into the moments, choices, and emotions that awakened a deeper sense of vitality. Whether it’s connecting with people, connecting with music, or a general sense of safety, we discussed stories when people felt alive. Tune in, and let’s discover together what makes us feel most alive.Connect with David on InstagramRead David's Substack

In this episode, you will hear the origin story of a community, my Hot Pods, a business, and much more. You will hear about these key moments, what we learned from them, and how things are going now. Tune in to hear stories of creativity, inspiration and passion from those who dared to take the first step. If you've ever wondered how great things begin, this is the episode for you!Connect with David on InstagramRead David's Substack newsletter

Being a community builder is hard. You may want to grow your community but also want to do it thoughtfully. You may want to scale its intimacy but not if it is going to hurt the quality of the community. And then there are business model considerations and challenges. In this Podcast Mixer episode, 10 or so community builders discussed these kind of challenges. If you are a community builder or want to be, this episode may definitely be for you! Connect with David on InstagramRead David's Substack

What is something that has changed you? In this episode, you will hear short stories and discussion on this topic. You will learn how projects, relationships, cities and more changed people. You never know what the next thing will be that changes you. Listen and enjoy this episode!Connect with David on Instagram

What is something that you have overcome? In this episode, you will hear short stories from people about overcoming something in their lives. Hopefully it helps you realize that whatever you are going through today that it can get better. For me, it was overcoming shyness. I am not shy anymore and this has greatly improved my life. Listen to hear amazing stories!