The Pathless Path with Paul Millerd

Latest Episodes:

#122 Indie Life & The Future of Work - Venkatesh Rao Nov 22, 2022

Show notes

This episode was a delight. Venkatesh Rao is the creator of Ribbonfarm and has been writing about the internet, technology, and gig life. This conversation focuses on his recently published book, The Art of Gig.

If you are thinking about working independently, becoming a freelancer, or are interested in consulting, you should definitely buy his book:

WATCH ON YOUTUBE: https://youtu.be/KC63HrF8V4E

You can find Venkatesh:

on Twitter @vgr
on RibbonFarm (blog and substack)
His consulting website: venkateshrao.com

Links Mentioned:

How Karate Kid Ruined The Modern World (Cracked)
Lords of Strategy
What Theorising Is, Theorising Is Not
Tempo, by Venkatesh
Jim Keller
Squad Wealth

We talked about:
1:00 The scripts Venkatesh grew up with
5:05 Preparing for the leap, Dan Pink's books
10:48 Predictable income vs adventure
18:58 Is $100 enough to build confidence in a project?
21:08 Understanding the big consulting companies
27:18 The positioning vs people's school
33:34 "Avoid polished deliverables"
42:17 Helping the executives take a step back
47:54 Systematic doubt and systematic confidence
51:40 What is "the clutch class" and why does it matter?
59:34 "What the clutch class is doing on evenings and weekends everyone will be doing in 10 years"
1:01:54 Keeping a 10-foot pole between your public identity and freelance gigs
1:03:38 How does Venkatesh work with clients?
1:07:53 The Yak collective and the future of indie consulting
1:12:34 Why the gig economy will outgrow the paycheck economy?

📕Buy Paul’s Book (Published Jan 2022): The Pathless Path

📲Connect + Follow Paul

Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality video using Riverside: Sign Up Here
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial

#121 Carving Your Own Path In a "Vibecession" - Kyla Scanlon on leaving her job, writing online, TikToks as Poetry, and The Passion Crisis Nov 14, 2022

Show notes

I believe that Kyla Scanlon is one of the most talented all-around creators. She is transcending the assumptions about what people want, especially with things like short-form videos. Her TikToks are synthesized, thoughtful, and funny, setting a new bar for what people want in an information age.

We talked about her journey growing up in Kentucky, writing online, hacking into the finance industry from a non-target school, and ultimately deciding to become self-employed with less than two years of work experience. Someone at her company told her she wouldn't "make it"

🍿WATCH ON YOUTUBE

Kyla's Website: Educator, Creator, Investor
Follow Kyla: @kylascan on Twitter, Instagram, and TikTok
Path Role Model: Cody Ko

⌛TIMESTAMPS
1:09 The scripts that Kyla grew up with
2:26 Writing her first book
5:01 Finding out that people actually want deeper ideas
7:31 Kyla's mindest when she was graduating
9:24 Why Kyla didn't like her "cool" job in LA?
11:50 DMing Paul and quitting her job
16:05 Approach to work in Kyla's age cohort
17:19 Kyla's parents on her leaving her job
18:05 Pushback and skepticism
19:27 Positive surprises after going on her own path
20:27 "The passion crisis"
23:24 How to find things you care about?
25:26 Gatekeeping and aging out
27:27 Kyla's short vertical videos
33:09 AI and the future of writing
35:58 Doing, not doing, and bike riding
38:17 Remembering the good ideas
38:48 The vibes of the economy
41:20 Influence and responsibility
42:58 Favourite financial leader?
43:50 Why Kyla doesn't like what the Fed is doing?
45:33 Generations living in different realities
47:00 How did the "vibes" of Kyla's path change?
50:51 Kyla's biggest supporters
51:23 Putting herself out there
52:04 Fame, success, and imposter syndrome
54:03 Charts in Kyla's videos
54:50 Kyla's TikTok's as poems
55:48 What do people get wrong about short-form videos?
56:46 Going from TikTok to YouTube
57:27 Bread
58:32 "Money is not our moral compass".
59:15 What does Kyla need help with?

📕Buy Paul’s Book (Published Jan 2022): The Pathless Path

📲Connect + Follow Paul

Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality video using Riverside: Sign Up Here
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial

#120 How Do You Buy A Home While Self-Employed? Catherine Cusick on her path, acting, economics of Broadway, longreads, independent book sales, buying a home, digital media & how to navigate hostile US self-employment regulations, Nov 07, 2022

Show notes

The legible story is that Catherine is a writer, producer, and digital media consultant. She helps creative people connect with new audiences, usually writers, usually online. But she hasn't had a W-2 job since 2017. Before that she worked as an actor, worked at a company called Longreads, and then has done a bunch of solopreneur experiments over the past five years.

Her recent interest is writing and speaking about how to navigate systems that make self-employment harder in the United States, like housing, healthcare, taxes, and insurance.

🍿WATCH ON YOUTUBE

Links:

Her How To Get A Mortgage Course
Her Website
The Catastrophe of Success (Tennessee Williams)
Small Bets Community

📕Buy Paul’s Book (Published Jan 2022): The Pathless Path

📲Connect + Follow Paul

Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality video using Riverside: Sign Up Here
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial

Audio Timestamps:
0:00 Audio intro
2:10 What were the scripts Catherine grew up with?
8:46 The differences in the experience of work between generations
12:19 Applying to Emerson - the cold, unwelcoming Boston
16:02 How Vassar teaches acting
16:41 Auditioning in New York City after graduating
17:16 Becoming disillusioned with a career path as an actress
20:24 Producing her first play
23:34 The American Booksellers Association
30:24 Creating jobs for herself
33:15 Working at Longreads
38:00 Leaving Longreads
39:30 After Longreads - moving to Austin
44:17 Designing life with her husband
48:18 How the system is incompatible with the new ways of life
48:52 Leaving the US as a way to gain perspective
49:42 "I'm breaking some law right now, I just don't know which one"
50:37 Does work equal suffering? The IRS' definition of a hobby
51:44 Why Catherine doesn't think in long time horizons
52:59 Getting a mortgage as a self-employed person
59:12 Small Bets & Dan Vassallo
1:01:55 LLC vs. S Corp
1:12:24 Healthcare in different states
1:16:55 Catherine's course
1:17:20 Tennessee Williams - The Catastrophe of Success
1:23:24 Cathrine's path role models?

#119 Goosebump-inducing Waves of Knowingness - Jonny Miller on grief, friendship, living abroad, founding a company, remote work, Rolf Potts, David Whyte, poetry, and finding work that matters. Oct 27, 2022

Show notes

Enroll In The 5th Cohort of Nervous System Mastery: You can get $250 OFF using the code PATHLESS => nsmastery.com

Jonny Miller is a dear friend and I've had the privilege to get to know him closely over the past four years on our own journeys. We've lived in Japan, Indonesia, and Mexico together. When we met we were both single but now are both married in cross-country relationships and have navigated finding work that matters, getting married, and living in foreign countries together.

🍿Watch on YouTube

This conversation was really special.

Links:

My interview with Jonny on The Curious Humans podcast
Paul's Interview with Al Humphreys
The Three Marriages (David Whyte)
Jonny's TEDx Talk on Grief

----

📕Buy Paul’s Book (Published Jan 2022): The Pathless Path

#118 A Better Future for Healthcare - Andy Schoonover on Crowdfunding for Healthcare, Search Funds, Buying A Company, Work-Life Balance, Bitcoin & Problems With Healthcare Oct 24, 2022

Show notes

Andy Schoonover is the CEO of one of the sponsors of this podcast. After talking with him I actually thought he'd be a great guest on the podcast. He has a fascinating story from going from search-funder post-MBA grad to forming his own healthcare company. Can his company fix healthcare? Can anyone? Time will tell but I'm rooting for him.

Join CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here (Sponsored Link, Includes discount)

------------------

📕Buy Paul’s Book (Published Jan 2022): The Pathless Path

📲Connect + Follow Paul

Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe

Further Ways To Support The Podcast:

I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality video using Riverside: Sign Up Here
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial

#117 The Truth About Remote Work - Ali Greene on being a remote leader, leaving the default path, stories and taking breaks, living in different countries, & writing a book Oct 17, 2022

Show notes

🍿 Watch on YouTube

Ali Green has been a remote worker since 2014. It took her a couple of attempts to fully unpair from the office and even when she had a fully remote job it took her another year to lean into her freedom. Now she's writing a book about what she's learned leading teams, living in different countries, and working remotely.

Quitting her job and inventing a "story"
Experiences working remotely since 2014
Working full-time remotely for Duck Duck Go
What people get wrong about remote work
Individual preferences & desire for freedom
Why she's writing a book
Productivity & remote work

Learn more:

Ali's Book "Remote Works" (Feb 2023)
LinkedIn

-------------

📕Buy Paul’s Book (Published Jan 2022): The Pathless Path

📲Connect + Follow Paul

Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality video using Riverside: Sign Up Here
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial

#116 From The "Holler" to Therapist to Creator Coach - Corey Wilks Psy. D. On Helping People Thrive Oct 11, 2022

Show notes

Dr. Corey Wilks is a Licensed Clinical Psychologist and Executive Coach with over 15 years of psychological experience.

In 2020, he stopped practicing therapy and ventured into entrepreneurship. Now, he coaches entrepreneurs and creates content to help people be more intentional with how they live, work, and create.

His latest project is Intentional Life Design, a 5-week live cohort-based course focused on helping people overcome limiting beliefs, think bigger, and do work that matters.

Find More About Corey

------------------

📕Buy Paul’s Book (Published Jan 2022): The Pathless Path

📲Connect + Follow Paul

Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality video using Riverside: Sign Up Here
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial

#115 Creativity as a Compass - Anne-Laure Le Cunff on Leaving Google, Freelancing, and Combining Creativity & Neuroscience, Oct 03, 2022

Show notes

In this episode, I talk with fellow creator and curious human Anne-Laure Le Cunff. She left her job at Google and embarked on an entrepreneurial journey about one month before I did in April 2017. We compare the lessons we have learned over the past five years as well as talk about:

How her mother's experience as an immigrant influenced her work scripts
Her creative interests vs. practical career choices
Getting into google and getting sucked into the tech world
Quitting her job and thinking she needed to found a company
Shifting to freelancing and creating space in her life
Creating and writing online and building an audience
Creating in a second language
Hiring employees vs. hiring contractors
Pursuing an academic path at the same time as a solopreneur path

Her personal site: Anne-Laure Le Cunff | Wellness, Creativity & Culture
Her newsletter & community: The Maker Mind Newsletter by Anne-Laure Le Cunff (nesslabs.com)

🍿 Watch on Youtube

-------------

📕Buy Paul’s Book (Published Jan 2022): The Pathless Path

📲Connect + Follow Paul

Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality video using Riverside: Sign Up Here
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial

#114 Training Elite Wall Street Traders - Michael Steiner on his time at SIG, using games to train market makers & becoming a high school teacher Sep 26, 2022

Show notes

Mike Steiner found himself on Penn’s campus at a young age not really knowing what he was supposed to do next. Thanks to helpful roommates, he started to figure out how to take advantage of the opportunities around him. He started getting more interested in math, statistics, and finance. He eventually ended up interviewing in New York and ending up at the famous training firm Susquehanna Investment Group (SIG). As a part-time trainer at first and then in a more central role, Mike started to experiment with different ways of teaching things like market making, probability, thinking in bets, and the behaviors needed to "make it" in the trading pits.

This conversation was a delight and I think you'll enjoy it. We cover:

Ending up at Penn and not really knowing what he was going to do
Figuring out he enjoyed math and finance
Getting a job at SIG
Joining the training team
Leaving finance to spend more time with his kids
Becoming a high school teacher
How he thinks about teaching & mentorship
His 20-year journey in creating his game "Stockslam"

Prefer Video? 👉 Watch on Youtube

Learn more about stockslam:

📕Buy Paul’s Book (Published Jan 2022): The Pathless Path

📲Connect + Follow Paul

Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality videos using Riverside: Sign Up Here
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial

#113 Beyond Hustle Culture & Helping Creators Make Money - Justin Moore from Creator Wizard on his journey as a Youtuber, creator, brand agency founder, musician, and now Sponsorship Coach Sep 19, 2022

Show notes

Today I’m talking with Justin Moore - he and his wife was what he calls “OG Youtubers.” From creating content to landing sponsorships to building his own agency, he’s seen every angle of the creator economy. a lot over the last ten years. In the past couple of years, he walked away from the agency and has stumbled into a new path, one he’s finding a lot of joy following - helping other creators getting paid as a sponsorship coach.

He turned down a buyout offer for his course and newsletter because he enjoys it so much. Check out this convo as we explore: