Portfolio Career Podcast

In 2020, the world of work dramatically changed. Workers have adjusted and found it might be easier now to build a Portfolio Career than before. Investors like Virginie Raphael saw these shifts too. Through her own firm Full Circle, she is investing into companies that are building into a world with Portfolio Careers and firmless professionals being more common. In this episode, you will learn about emerging business models, leading companies, and how Virginie hired someone with a Portfolio Career. Excited for you to build and grow your Portfolio Career! As always, this episode with notes is available on my website.Connect with Virginie on LinkedIn!Connect with David on Twitter!

How have you decided how to live? Derek Sivers wrote a book called How To Live, which details 27 conflicting ways of living to hopefully help you decide. In this episode, you will learn common through-lines among the 27 conflicting ways, how you should think about the 27 ways, and how to think about your career. You will also learn actionable ideas from another one of Derek's books called Your Music and People and about his popular decision-making framework, "Hell Yeah or No." Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.You learn more about Derek on his website, where you can also email him.Connect with David on Twitter!

Need a new strategy or tactics for navigating in the current economic market? Nick deWilde has practical advice for you to navigate the downturn. His ideas are helpful if you are soloprenuer and/or if you are looking for a new job. Nick is the Cofounder of Invisible College and the creator of the Jungle Gym newsletter. You will learn how he has navigated the last 12 months as well, and why now could be a good time for you. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Nick on Twitter!Connect with David on Twitter!

What do Operations professionals do? How could you brand yourself in Operations and build a career out of it? Caro Griffin loves answering these questions. She has been working in Operations for 10 years. She is currently the VP of Operations at Tech Ladies and the Founder of Opsy, a community for Operations leaders working in tech. You will learn how to think about positioning yourself in the Operations field, freelancing, the power of low-code tools, and the growth of Operations roles. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Caro on Twitter!Connect with David on Twitter!

Emerging technology is creating new work opportunities for people. It also provides us new terms that we can apply to our existing work and how we think about it. In this episode, Ilana Ettinger shares how some practices that happen natively in Web3 can be applied to Web2. You will also learn other Portfolio Career trends like people negotiating to have a side hustle when starting a new job. Ilana also shares her recent career transitions and how she has been able to get referrals as well. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Ilana on LinkedInConnect with David on Twitter

Do you want to have a creative career? Lawrence Yeo is the Founder and Creator of More To That, a blog that has many deep dive essays. He is a consultant and course creator as well. In this episode, we talk about a recent post called The Arc of the Practical Creator. The post details three stages balancing the passion for creativity with the practicality of making money. If you are interested in having a creative career, this episode is for you. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Lawrence on Twitter!Connect with David on Twitter!

Do you want to have a career centered around relationships and helping people? Perhaps, the community industry is a good fit for you. Since 2007, Rosie Sherry has been working in this field. She is the Founder of Ministry of Testing and notably was the Community Manager at Indie Hackers. Rosie is a prolific tweeter and writer. In 2022, Rosie became a self-employed community builder offering a variety of products and services. In this episode, you will learn about Minimum Viable Communities, how to build a community-led business, and why conversation is at the heart of communities. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Rosie on Twitter!Connect with David on Twitter!

What could you do in two hours that could improve your quality of life? Nick Gray wants you to host a 2-hour cocktail party to build big relationships, which can help your career. When Nick moved to New York City, he tried organizing all types of events to build relationships. He realized that a 2-hour cocktail party was the best event for him to host. His new book, The 2-Hour Cocktail Party, is out in June 2022. In this episode, you will learn how to organize your own cocktail party and other life hacks. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Nick on TwitterConnect with David on TwitterLearn more about Nick's book on his website

Want to pivot into a new industry or field? Nora Ali has pivoted from finance to startups to media, while working at leading companies along the way. Each of these chapters gave her the experience, skills, and relationships to help her for her next chapter. Nora is building a new media company. While doing so, she is also the cohost of the Business Casual podcast produced by Morning Brew. In this episode, you will learn how Nora has attracted new opportunities, successfully reached out to people and pitched new opportunities, and how to pivot. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Nora on Twitter!Connect with David on Twitter!

Do you want to think and act in your career like entrepreneurs do? Consider reading The Startup of You book. This episode is a summary of a 2022 updated version of this book written by Reid Hoffman and Ben Casnocha. The latest version includes how having a Portfolio Career is viable these days, and how to think about it. In this episode, I share and discuss Portfolio Career insights and other top ideas from the book. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with David on Twitter!

In 2018, Justin Gordon started the Just Go Grind podcast. And his life has not been the same since. That show has published over 320 episodes. In this episode, you will hear how one episode helped led to Justin getting his current job at Director of Marketing at Vitalize Venture Capital. Justin also hosts another podcast through Vitalize Venture Capital. If you are interested in how podcast can accelerate your career and help you build relationships, this episode is for you. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Justin on Twitter!Connect with David on Twitter!

We know that have a mentor or mentors in our life is a good idea. But how do we actually form relationships with mentors? Janice Omadeke is the Founder of The Mentor Method, a startup helping companies large mentorship programs. In this episode, you will learn how to find mentors, how mentors could help, and how Janice scaled her side hustle into the company that it is today. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Janice on LinkedIn!Connect with David on Twitter!

Podcasting has transformed my life. And I want to share my podcasting knowledge and process to hopefully help your podcast and Portfolio Career. To do so, I recently launched a new podcasting course called How To Start and Scale a Podcast. In this episode, I shared an overview on the 9 lesson email video course, the benefits of creating *anything*, and why now is a GREAT time to start a podcast. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website!Let's connect on Twitter!

Did your work and life dramatically change starting in 2020? For Katie Gatti, it did. When her in-person side hustle was no longer an option, she started taking her personal finance content much more seriously. As part of this, the Money with Katie brand and business was born. She recently sold her business to Morning Brew and is now a full-time creator with multiple income streams. In this episode, you will learn how she grew her side hustle and business, how you could collaborate with brands on content, and personal finance tips too. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Money with Katie on TwitterConnect with David on Twitter

Haley Bryant started teaching indoor cycling classes while working full-time in 2016. She used the savings from this to buy a condo. She has used other side hustles and personal projects like advising companies, blogging, and angel investing to build her Portfolio Career. She is currently the General Manager at Golden Wok and a Venture Partner at Hustle Fund. If interested in side hustles and angel investing, this episode is for you! Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Haley on Twitter!Connect with David on Twitter!

We typically think we need to wait 10+ years before taking a sabbatical from work. Amy McMillen decided to take one much earlier. During her sabbatical, she wrote a book called Reclaiming Control. In this episode, Amy talks about overcoming burn-out, the benefits of writing a memoir type of book, and why it's not your jobs job to make you happy. Excited for you to build and grow your Portfolio Career! As always, this episode with notes is available on my website.Connect with Amy on Twitter!Connect with David on Twitter!

Society wants you to believe that you should get good grades in, climb the corporate ladder, get married, buy a house, and then retire happily ever after. But, that is not the only life path. Paul Millerd has introduced a new path called The Pathless Path. This is also the title of his book. In this episode, I share key ideas from the book, including the differences between the Default and Pathless Path. And how you can define and create your own success with the Pathless Path. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is on my website.Learn more about The Pathless Path here.

Change is happening all around us. Unfortunately, it can very hard when it is *us* dealing with change. People are changing jobs more and more these days, in addition to many other life changes. Rei Wang is the cofounder of The Grand, a new and innovative group coaching company. In this episode, you will learn how to better understand change. Rei is also an angel investor into companies that focus life transitions. If you are going through a transition and/or are building a community-centric business, this episode is for you! Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website!Connect with Rei on TwitterConnect with David on Twitter

Allison Esposito Medina has built Tech Ladies, the largest community of women in tech. It initially started as a coffee networking gathering in New York City in 2014. More than 7 years later, the community now helps 100,000+ women. When Tech Ladies started, Allison was also working another job. In this episode, you will learn how she grew the community, and when she decided to go full-time on it. In this episode, you will also learn about branding, consistency, community building, and job searching advice. Excited for you the build and grow your Portfolio Career!As always, this episode with notes is available on my website!Connect with Allison on Twitter!Connect with David on Twitter!

What is one of the important skills for your career? Your creativity. Maria Brito used to be a corporate lawyer in New York. After leaving law, Maria became an art advisor, creator creator, and more. She tapped into her creativity and created her own lane and path. She is the brand new author of How Creativity Rules The World. If you are look into learn more about your creativity, this episode is for you. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with David on TwitterConnect with Maria on Twitter

We are often told to believe that there is one path for us to follow. However, through my journey, I have taken many different paths. And sometimes, multiple ones at the same time! Rebekah Bastian is the author of Blaze Your Own Trail and the Cofounder of Own Trail. The book and her company help you see this too, and empower you no matter where you are. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Rebekah on Twitter!Connect with David on Twitter!

Three years ago, Daniel Vassallo quit working at Amazon. He was a very highly-paid software developer there. Without a job lined up, he wanted to create his own path. He currently has a portfolio of small bets (products, services and more) and wants to help you do the same. Daniel has over 110,000 Twitter followers. In this episode, you will learn how to use Twitter tips as well. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Daniel on Twitter!Connect with David on Twitter!

Sharing your ideas publicly and reaching out to people are two good things for your career. For Paige Finn Doherty, sharing on Twitter helped her get a job which then lead to more opportunities. She is the author of Seed To Harvest, a simple book to help you understand the venture capital business. She is currently the Cofounder Behind Genius Ventures and the host of the Seed To Harvest podcast. She is also passionate about cold email sharing actionable tips and stories here for you. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Paige on Twitter!Connect with David on Twitter!

Are you looking to improve your Zoom video meeting presence and effectiveness? Lorraine Lee was an early employee on LinkedIn's video product team. She is now on a mission to help people stand out more over video. In February 2022, she has a brand new cohort based course out called Engage Your Virtual Workforce. In this episode, you will learn actionable tips for your next video meeting and develop your brand on LinkedIn. Excited for you to Build and Grow your Portfolio Career!As always, this episode with notes is on my website.Connect with Lorraine on LinkedIn!Connect with David on Twitter!

When I started the podcast in the summer of 2018, two of my roommates then were Juvoni Beckford and Kean Gardner. For episode 200, I was able to celebrate it with them and share their insights for you. In this episode, you will hear their life updates, the transitions they are going through, what they are prioritizing in 2022, skills they want to learn, why a writing practice is important to both of them and more. Excited for you to build and grow your Portfolio Career! As always, this episode with notes is available on my website.Connect with Juvoni on Twitter!Connect with Kean on Instagram!Connect with David on Twitter!

One of the easiest ways to change your prospective and who you can become is by changing the people you are around. For Katya Stepanov, she was inspired by creatives and entrepreneurs who were creating their own paths in New York City. In addition to many person projects, Katya is the Cofounder of the Inheritance Project and Rebis Immersive, a storytelling advisory company. If you are a coach or a facilitator looking to learn how to sell-into companies and grow, this episode is for you. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is on my website.Connect with Katya on Instagram!Connect with David on Twitter!

It's been a hard 2 years in many ways for us. Some of us have dealt with burn out during this time and or are currently dealing with it. Morgane Michael is an educator, podcaster, and now an author with an overall focus on mobilizing kindness. Her new book is called from From Burnt Out to Fired Up to help people overcome burn out. In this episode, you will learn how Morgane's podcast and other creative practices led to this book and her book deal with a publisher. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website!Connect with Morgane on Twitter!Connect with David on Twitter!

When Lisa Cuesta first got involved with the cryptocurrency sector in 2017, the sector mostly contained whitepapers and ideas compared to companies and real projects. Since then, the sector has grown and matured, especially in the last 18 months. In June 2021, Lisa published a blog post sharing why she was transitioning full-time into the sector. In this episode, we discuss her transition, crypto and web3 industry trends, and how she is also investing on the side. Being an investor and an operator is a trend that she thinks will continue to grow. Excited for you to build and your Portfolio Career! As always, this episode with notes is available on my website.Connect with Lisa on Twitter!Connect with me on Twitter!

How was your 2021? I wanted to share 20 reflections from my year. Many of the reflections are related to my Portfolio Career. Some include stories and insights into how I am thinking about my Portfolio Career now. In 2021, I had 3 different jobs and gigs and I talk about that journey in hopes that it helps you. Thank you for being part of the show in 2021, and I am excited to build and grow our Portfolio Careers together!As always, this episode with notes is on my website.

Annika Lewis had been writing about web3 and cryptocurrencies for some time. After a conversation with a friend, she decided to leave the venture capital industry to work at Gitcoin, a DAO. Her journey to this role is filled with interesting stories and actionable insights. If you are looking to learn more about how work and Portfolio Careers are changing because of cryptocurrency and web3 technologies, this episode is for you. Excited for you to Build and Grow your Portfolio Career!As always, this episode with notes is available on my website.Learn more from Annika on Twitter!Learn more from me on Twitter!

Writing a book is hard. With two people writing it together, there are synergies and accountability benefits. For Ashika Kalra and Jade Chen, they decided on writing a book profiling personal stories of 25 female leaders in New York City. By connecting with these leaders over cold email, they completed interviews and the beautiful book together. They did so while both working busy and impactful full-time jobs. Behind Her Vision was released in December and this episode discusses their journey and how you could write a book. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website. You can learn more about my Twitter as well!

Emerging technologies are changing the world of work. In 2021, there has been a growth in popularity in DAOs (Decentralized Autonomous Organizations) has an organizational structure. Kinjal Shah cofounded an investment DAO called Komorebi Collective. Kinjal is also an investor at Blockchain Capital. In this episode, you will about how to get involved with DAOs, the benefits of them, and how its possible that you could participate in multiple DAOs for a combined full-time job.As always, this episode with notes is available on my website.You can learn more from Kinjal on Twitter!You can (hopefully) learn from me on Twitter too!

In 2021, there has an explosion of interest, activity, and investment in the Web3 sector. Dror Poleg is an author and also teaches a new cohort-based course called Hype-Free Crypto. In this episode, you will learn how to think about Web3, how to potentially get started, and why there is a lot of interest in the space. On a high-level, Dror shares why he is super bullish on the power and possibility of the internet to build relationships, become more anti-fragile, and spark professional opportunities. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Dror on Twitter!Connect with David on Twitter!

Arlan Hamilton is first non-celebrity Black women to be featured on the cover of Fast Company. She is the Founder of Backstage Capital, author of It's About Damn Time, has her own educational academy, and is recently the Founder of Runner. In this episode, you will learn how Arlan started building these complimentary ecosystems, why information is valuable, and how it only takes one "yes" for you to find your next big opportunity. Excited for you to build and grow your Portfolio Career! As always, this episode with notes is available on my website.Connect with Arlan on Twitter!Connect with me on Twitter!

Growing a coaching business is hard work. For Nikki Goldman, she has been able to grow her B2B coaching business, I/O Coaching, by producing great work. She has been able to grow it largely without using social media. You also learn about how to have hard conversations and the future of Portfolio Careers. Excited for you to Build and Grow your Portfolio Career!As always, this episode with notes is available on my websiteLearn more about Nikki and I/O Coaching here.Connect with me on Twitter!

Sahil Lavingia's new book, The Minimalist Entrepreneur, provides a roadmap for a different path compared to the one painted by Silicon Valley. A few pillars are starting, creating content, and being active in community. These pillars can be viewed as foundational to building a Portfolio Career. In addition to being the CEO of Gumroad, Sahil is a painter, course creator, investor, and now an author. His company, Gumroad, hires quarter-time executives to allow for them to work on other things and build out their Portfolio Career. In this episode, you will also learn how working remote has opened up space and potential opportunities for you. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Sahil on Twitter! Connect with me on Twitter!

The world of work is changing. New roles and paths are being created daily. For Steph Smith and Calvin Rosser, they have decided to not pursue corporate ladder, but instead create their own path. They cohost The Shit You Don't Learn in School podcast and also work on other projects. If you are looking for proven approaches idea, frameworks, and how you could be more anti-fragile in your career, this episode is for you! Excited for you to Build and Grow your Portfolio Career!As always, this episode with notes is available on my website.Connect with Steph on TwitterConnect with Calvin on TwitterConnect with David on Twitter

Freelancing is a great way to do work that you actually made. In this episode, you will learn how it can happen in a few different ways as a business owner, employee or soloprenuer. Jen Waldman and Peter Shepherd both consider themselves freelancers, while approaching the work with a different lenses to provide you multiple ideas and approaches to understand. They co-host The Long and The Short of It podcast together making this conversation action-packed and engaging for you. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my website.Check out The Long and The Short of It podcast.Let's connect on Twitter!

In 2017, Paul Millerd left working for a consulting firm in New York. He has since been on the Pathless Path and designing his life around other things like writing and freelancing. Paul is now writing a new book called The Pathless Path to help normalize the path of going off the traditional or historical script. If you are looking to better understand your current or possible relationship to work, this episode is for you! Paul is a consultant, course creator, podcaster, and newsletter writer. Excited for you to build and grow your Portfolio Career! As always, this episode with notes is available on my website.Connect with Paul on Twitter.Connect with David on Twitter.

Are you looking to jump-start your Portfolio Career? Podcasting has changed my life. It has helped me build and grow my Portfolio Career. In this episode, you will learn 30 reasons how podcasting could help your career. This episode is a follow-on to an earlier episode when I shared 15 reasons. Excited for you to build and grow your Portfolio Career!As always, this episode with notes is available on my websiteLet's connect on Twitter!

We often told to find a job that looks good on paper. Unfortunately, many of those jobs are leading to a lack of fulfillment and excitement. Jen Glantz is the creator of the Odd Jobs newsletter, which profiles how you can find an "odd job." One that could be more exciting and rewarding for you. Her main business, Bridesmaid for Hire, is a service that led national fame including Good Morning America and The New York Times. She is a 3x author and podcast host as well. In this episode, you will learn:- why Jen wants to help you find an odd job- the importance of figuring out who you want to be the hero too- why consistency is important for creators- why understanding what fascinates you is a great question to ask yourselfAs always, this episode with notes is available on my website! Excited for you to Build and Grow your Portfolio Career!

Do you Google people before you met them? Turns out, pretty much everyone does that for you as well. Kim Kaupe is the creator of the brand new cohort-based course called Career Capital. In her course, Kim aims to help you improve how you show up when you are Googled. Kim is also an expert on using LinkedIn and Kim shares actionable tips for you in this episode. You will also learn how Kim has created a portfolio of online courses. Excited for you to Build and Grow your Portfolio Career!Learn more about Kim's Career Capital course that starts in October HEREAs always, this episode with notes is available on my website HEREConnect with Kim on Instagram!

When we seek support, we can open ourselves to new opportunities. For Victoria Song, she has worked over 25 coaches. She learned the coaching ins-and-outs and is now an advisor and coach to leading technology company entrepreneurs. After starting her career as a venture capitalist, she had an epiphany and want to help people be more heart-centered and aligned with their work. She is the new author of Bending Reality. Excited for you to Build and Grow your Portfolio Career!As always, this episode with notes is available on my website!Connect with Victoria on her website and Instagram!

Launching a Cohort-Based Course for the first time could be very scary. When you are working full-time as well, it could seem even harder. For Sara Sodine Parr, she had thinking about creating a course in 2020. Her background and expertise is in customer research to help companies build products that users want. In the summer of 2021, she launched her new course, Build The Right Thing. In this episode, you will learn:- how she was able to do so while working- how teaching sharpens your thinking- how it opened up new opportunities for herAs always, this episode with notes is available on my website.Connect with Sara on Twitter

Writing one book is good for your career. But how about publishing 7 and writing 10? For Luca Dellanna, he likes the idea of having a portfolio of books and work to help different people in different ways. He also likes how this makes his career more antifragile. He is an expert on this topic and teaches an Antifragile Organizations Cohort-Based Course. In this episode, we talk about career antifragility and one of Luca's recent books, 100 Truths You Will Learn Too Late. Excited for you to Build and Grow your Portfolio Career! In this episode, you will learn:- the benefits of creating a not to-do list- 4 factors that disproportionally affect your career- how the 80-20 can be applied to your career and life- why many benefits come from compounding work and relationshipsAs always, this episode with notes is available on my website!Connect with Luca on Twitter!

When did you realize that could be a community builder? Laís de Oliveira believes that everyone has the capacity to do so, if we choose to do so. Professionally, the opportunities to do so are growing by the day. Laís is the author of the book, Hacking Communities, after she learned frameworks after somewhat stumbling into the community building field. Today, she is the Program Director for the On Deck Community Builder Fellowship helping community builders grow professionally. In this episode, you will learn:-how everyone can be a community builder-frameworks and mental models to apply immediately -how a professional community builder can grow professionally As always, this episode with notes is available on my website.You can connect with Laís on Twitter!

If you knew that change was the constant, what would you do differently? April Rinne's new book called Flux: 8 Superpowers For Thriving in Constant Change helps you discover and adopt a new mindset and compass to move forward. One of the Superpowers is "Creating Your Portfolio Career." April was a prior podcast guest on the show also. In this episode, I summarize the book for you. Excited for you to Build and Grow your Portfolio Career! As always, this episode with notes can be found on my websiteLearn more about the book here!

The tables were turned and Carly Valancy interviewed me to share some updates on my end! Recently, I got a new job and I wanted to tell you about it. Currently, Carly is the Director of Community at NuMarket and the Cofounder of The Reach Out Party. We talk about reaching out, staying in touch, and the benefits of podcasting. Excited for you to Build and Grow your Portfolio Career! As always, this episode with notes is available on my website.Learn more about Carly on her websiteLearn more about The Reach Out Party

Have you ever wanted to launch a side hustle? It can be really hard to learn about ways to make some extra money with your ideas, interests, and skills. Insert: Side Hustle Stack. While on a gap year from Stanford, Lila Shroff co-created the Side Hustle Stack for people to learn ways to make some extra income and build out their Portfolio Career. Lila is also a Research Analyst at Atelier Ventures, a venture fund focused on the passion and creator economy. Excited for you to Build and Grow your Portfolio Career!As always, this episode with notes is on my website.Connect with Lila on TwitterConnect with me on Twitter

In 2018, I created my podcast through a Cohort-Based Course created by Seth Godin by Alex DiPalma. Since then, the growth of Cohort-Based Courses has only accelerated. In the summer of 2021, Katherine Roan, JP King, and myself were honored to be three of the 14 freelance coaches in Maven's How To Build A Cohort-Based Course course. In this episode, you will hear our experience, how we think about coaching in a CBC, the different types of coaches in a CBC, the skills we developed, and more. You can learn more about Maven and incredible courses now available here.As always, this episode with notes is available on my website.