The Pathless Path with Paul Millerd

Adam Braff grew up in a house where writing was always encouraged. His mother published a newsletter, and his father was a data analytics consultant. He started out as a lawyer, but after the dot-com boom led to a surge in demand for consultants, he decided to make the switch. He now runs his own consulting firm and writes regularly on a variety of topics.  Braff himself became interested in consulting during the first dot-com boom. He transferred from MIT to Brown in order to study linguistics, and eventually became a strategy consultant at McKinsey.

Relevant Links:

• Adam's Website and McKinsey Essay
• Tom Critchlow's Writing
• Venkatesh Rao's The Art of Gig

Timestamps
0:00 Audio Intro
0:48 The scripts Adam grew up with
3:54 Shifting from MIT to Brown
5:33 Becoming interested in consulting
7:25 What was it like from 1999 to 2002?
9:08 Adam's path to becoming a partner at McKinsey
11:56 Leaving McKinsey
14:05 What kept Adam at McKinsey for 10 years?
16:06 What do people get wrong about McKinsey?
18:49 Decentralization and the emergent order
21:46 The new ideas in customer experience Adam helped shape
24:06 Going into the finance industry in 2009
25:23 Turning data into insights
27:20 How to influence other executives to embrace the "hypothesis first" framing?
28:44 The 2 skills from the consulting world that are missing elsewhere
30:28 Teaching the importance of feedback
33:22 Development Group Leaders
35:21 Lessons from working at a hedge fund
42:01 Did the world of billions inspire Adam to go solo?
42:56 Becoming a freelancer
46:52 Should you clearly define the services you're offering as a freelance consultant?
50:18 The role of Adam's writing
51:44 Did the nature of Adam's projects shift over time?
53:14 The best part of the self-employed life Adam didn't expect
54:15 AI & The Future
58:10 The forecasting contest

📕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

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:

• The Art of Gig, Foundations
• The Art of Gig, Superstructures

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

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

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?

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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

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

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)

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📕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

🍿 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

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📕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

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

• Writing on Psychology Today
• His personal website 

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📕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

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

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📕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

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:

• Twitter
• Website

📕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