TKS: The Karnjanaprakorn Show

Stack Your Obsessions

Michael Karnjanaprakorn — Wed, 03 Jun 2026 13:56:39 +0000

I have an addictive personality. When I get into something, I go all in. Health, sports cards, running, Magic, UFC, and right now Muay Thai, jiu-jitsu, and AI coding. Then a few months later I move on to the next thing. For a long time I thought that meant I was scattered. That I could not commit. I do not think that anymore. Here is what I think is actually going on. The intense phase ends, but what you picked up stays. The skills, the habits, the taste, the people. It all stacks up into a kind of life portfolio. I also get into the other side of it. Not every obsession is worth keeping. Some are just procrastination. And quitting one, like I did with golf, is not the same as failing. You are not flaky. You are building a life, one obsession at a time.

#42 - How to Get a Job at a Tech Startup or Becoming a Content Creator with my MTG Coach Stanley2099

Michael Karnjanaprakorn — Mon, 19 May 2025 17:58:44 +0000

In this episode, I chat with my Magic: The Gathering coach Stanley Hartman (Stanley2009) about different career paths. I flip the script and share my own advice with Stanley as we explore how to land a job at a tech startup, build a career as a content creator, and brainstorm software ideas through vibe coding. For anyone interested in career guidance, content creation, or startup ideas, this episode provides practical advice and actionable tips.

FOLLOW STANLEY

Patreon: https://www.patreon.com/c/stanley2099

X: https://x.com/stanley_2099

Youtube: https://www.youtube.com/@stanley_2099

Spotify: https://open.spotify.com/show/7I6IFHdvYOLeIMHtlhbNsC?si=d86a108fb335494c

FOLLOW ME

Website: https://mikekarnj.com

CHAPTERS

00:00 Intro

01:21 Getting a Job at a Tech Startup

25:25 Content Creation

57:01 Vibe Coding

#41: Danya Shults - Career Pivots, Sabbaticals, and Navigating Life’s Transitions

Michael Karnjanaprakorn — Thu, 27 Feb 2025 09:00:00 -0100

How do you know when it’s time to make a change—whether in your career, personal life, or mindset?

In this episode, I sit down with Danya Shults, who shares her experiences from working at Skillshare and Patreon to becoming an executive coach. We also talk about her recent psychedelic therapy, sabbatical in Spain, and navigating changes as you get closer to 40.

We discuss:

The emotional and practical side of career pivots
Why Danya and her husband quit their jobs for a four-month sabbatical

How founders (and anyone in transition) can avoid anticipatory grief
The role of intuition, spirituality, and psychedelics in navigating life shifts

This conversation is perfect for anyone experiencing major life transitions.

Follow Danya: https://www.danyashults.com

CHAPTERS

0:00 Intro

07:30 Sabbatical

16:59 Life After

32:08 Entering 40s

36:52 Marriage and Milestones

42:28 Spirituality

50:44 Psychedelic Therapy

59:51 Advice

#40 - Safwaan Kay: AI Agents, Open Source Software, and Ambition

Michael Karnjanaprakorn — Thu, 30 Jan 2025 10:00:00 -0100

Safwaan Kay is working on a new (stealth) startup. He was previously at Founders, Inc.

LINKS

Safwaan's X: https://x.com/safwaankay

I’m rich and have no idea what to do with my life: https://vinay.sh/i-am-rich-and-have-no-idea-what-to-do-with-my-life/

HOST

Michael Karnjanaprakorn: https://mikekarnj.com/

CHAPTERS

00:00 Introduction

03:31 Post Exit Founder Essay

20:18 Open Source

29:47 AI Agents

46:56 Ambition

My 2024 Review

Michael Karnjanaprakorn — Tue, 21 Jan 2025 10:40:00 -0100

Reflecting on the year has always been part of my annual process — celebrating wins, learning from challenges, and planning ahead. In this essay and podcast episode, I’ll share my highlights, lessons, and goals for 2025, along with some unexpected takeaways from a year dedicated to having fun.

Lessons

Dropping the Mask: Letting go of the personas we build to meet others’ expectations is difficult but transformative. Living authentically allows for deeper connections and a more fulfilling life.

Redefining Success: Inspired by my conversation with Kevin Dahlstrom, I’ve embraced a new version of the American Dream: sabbaticals, financial independence, passion-driven identities, and quality family time are what success looks like to me now.

Health is Wealth: Navigating my heart health issues and running injuries reinforced a simple truth: everything else in life rests on a foundation of good health. Without it, nothing else is sustainable.

Simplify to Focus: Decluttering my physical and mental space has been transformative. By owning less and streamlining commitments, I’ve freed up time and energy to focus on what I truly care about, whether it’s hobbies, relationships, or personal growth.

Transitions take Time: Big life changes rarely happen overnight. Shifting priorities, evolving identities, and exploring new paths require patience. Dead ends are part of the process; what matters is continuing to take steps forward without rushing the process.

Read: https://mikekarnj.com/posts/2024-review

Chapters

00:00 Intro

02:45 Highlights

26:32 Lessons Learned in 2024

29:54 Random

33:26 2025

#38: Andrew Conner - Mastering Curiosity and Independent Thinking in the Age of Algorithms

Michael Karnjanaprakorn — Tue, 12 Nov 2024 05:36:00 -0100

In this episode of TKS, we explore how adult curiosity, independent thinking, and cognitive growth shape not only our careers but also our entire approach to life. Our guest, Andrew Conner, co-founder of Levels, shares insights from his 18-month sabbatical, where he stepped away from the day-to-day of building a startup to dive deep into unstructured learning and personal exploration. We discuss the mental frameworks and practical tactics that sustain lifelong curiosity, why wisdom is "the best predictor of life satisfaction," and how to cultivate cognitive ability in an algorithm-driven world. Guest https://andrewconner.com/ is the co-founder of Levels. He is a software engineer, amateur potter, and tinkerer. Chapters 00:00 Intro 01:19 Sabbatical 06:01 Guardrails 14:05 Adult Curiosity 20:10 Placebo Effect 24:55 Unstructured Learning 28:43 Framework 29:33 Navigating Algorithms 31:06 Intentional Content Consumption 40:37 Synthesizing and Connecting Ideas 49:31 Career Advice for Young High Performers The Karnjanaprakorn Show TKS features honest conversations with people who think differently. We explore unconventional ideas across life, work, and culture — expanding how you see the world. Each episode tackles a central question through personal stories and expert interviews. Host I am the founder of Skillshare and Otis. Learn more about me: https://mikekarnj.com

#37: Rick Foerster - Finding Meaning for Overachievers

Michael Karnjanaprakorn — Thu, 17 Oct 2024 10:00:00 +0000

I chat with Rick Foerster, who shares his journey from a fast-paced tech career to one focused on family, creativity, and fulfillment. After twelve years at Privia Health, Rick took a sabbatical when the company went public. He used that time to reassess his priorities and shift from a work-centric identity to a multi-dimensional one. We discuss diversifying your identity and finding fulfillment beyond career success. We also explore the concept of ‘total addressable meaning,’ how finding meaning is the ultimate form of wealth, navigating midlife crises and avoiding burnout. This episode is perfect for anyone going through a transition, curious about taking a sabbatical, or seeking a more meaningful life beyond work. Guest Rick Foerster is a former healthcare executive who now writes at https://www.thewayofwork.com/. https://x.com/MattEspoz Topics 00:00 Intro 01:43 Rick's Journey 03:38 Life After Privia Health 08:25 Identity Shift 12:40 Sabbaticals 25:10 Ambition 36:00 Scaling Down After Scaling Up 40:02 Meaning 48:24 Advice for Those Feeling Stuck 54:36 Rebalancing Life's Portfolio The Karnjanaprakorn Show I am the ex-founder of Skillshare, and I am now exploring what's next. The Karnjanaprakorn Show (TKS) follows my journey as I chat with others, taking unique approaches to business and life. Learn more about me: https://mikekarnj.com

#36: Heart Disease Risk - My Journey with Lipoprotein(a)

Michael Karnjanaprakorn — Thu, 03 Oct 2024 11:00:00 +0000

At 41, I learned I was at high risk for heart disease despite what I thought was a healthy lifestyle. When I was diagnosed with high levels of lipoprotein(a)—a genetic risk factor—I decided to document my year-long journey of understanding and managing the condition. In the episode, I share my biomarker test results, explore heart disease risks, and discuss my lifestyle and medication plans. This experience has underscored the importance of early detection and taking control of my health. Read the full essay https://mikekarnj.com/posts/tackling-high-lipoproteina-my-heart-health-journey. Chapters 00:00 Intro 00:30 My Genetic Risk 02:01 Background 03:15 Test Results 04:47 Breakdown 07:31 DEXA Scan 09:17 Taking Action 13:49 Treatment 17:09 Mindset Shifts 18:28 My Plan 20:00 Follow-Up Results 23:21 Reflecting Podcast I am the ex-founder of Skillshare, and now exploring what's next. The Karnjanaprakorn Show (TKS) follows my journey as I chat with others who are taking unique approaches to business and life. Learn more about me: https://mikekarnj.com

#35: Matt Espinoza — Building a Startup Studio at 22

Michael Karnjanaprakorn — Thu, 08 Aug 2024 13:18:48 +0000

I chat with Matt about his unconventional path to building a holding company. At just 22 years old, he has already had two successful exits. We discuss his approach to building his studio model holding company, Halation, where he focuses on creating one-of-a-kind software. Matt shares how he selects the ‘game’ he wants to play, why he chooses to work with friends, and the importance of having a 'cash cow' to fund other ventures. We delve into validating new ideas, finding the right operating partners, and his whale-and-barnacle approach. Lastly, we exchange advice on balancing work and life.

Guest

Matt Espinoza is a partner at Halation, building an empire of internet companies. Follow him on X.

Chapters

00:00 Introduction 01:43 Building a HoldCo 05:14 Bootstrapping 06:57 Partnering with Creators 12:22 Acquiring vs. Building 15:14 Validating Ideas 27:53 Importance of Operators 31:51 Lessons Learned 37:20 Balancing Work and Life 45:40 Calm Company 51:10 Fun

Host

I am the ex-founder of Skillshare, and I am now exploring what's next. The Karnjanaprakorn Show (TKS) follows my journey as I chat with others, taking unique approaches to business and life. Learn more about me: ⁠⁠https://mikekarnj.com

#34: Kevin Dahlstrom - Designing a Life You Don't Need to Escape

Michael Karnjanaprakorn — Thu, 27 Jun 2024 11:55:14 +0000

Kevin Dahlstrom might be the most balanced person I’ve ever met. He’s a 4x Founder, 3x CMO, and investor in over 55 companies. He also pursues rock climbing at an elite level — all while prioritizing his family.

He says it’s only possible because of his “ideal end state” exercise. It aligns his actions with his true desires, allowing him to design a life he never needs to escape. As a result, he’s reduced work to just 10% of his identity.

As I navigate my 40s, I wanted to get his advice on making the most out of this decade. I chatted with Kevin to get his perspective on work, identity, health, lifestyle design, and more.

Guest

Kevin Dahlstrom is a 4X founder, 4X CMO, 50X PE investor, and avid rock climber.

Chapters

00:00 Intro 02:27 The Text 05:39 Lifestyle Design 11:38 Ideal End State Exercise 18:19 Manifesting Goals 21:28 Compounding 22:25 Reflections at 50 26:59 Work-Life Integration 32:08 Retirement 33:16 Minimalism 35:40 Climbing 37:09 Identity Beyond Work 39:50 Curating Your Tribe 41:39 Hobbies 47:27 Giving Back 52:40 Mental and Physical Health 01:04:12 End Quote

Host

I am the ex-founder of Skillshare, and now exploring what's next. The Karnjanaprakorn Show (TKS) follows my journey as I chat with others taking unique approaches to business and life. Learn more about me: ⁠https://mikekarnj.com

#33: Dan Reich — Post-Exit Life as a 4x Founder

Michael Karnjanaprakorn — Tue, 11 Jun 2024 18:51:07 +0000

Dan has sold four companies throughout his career. We discuss what that was like and dive into what he’s doing next—building a venture studio. He shares his playbook and how he's leveraging his strengths, and I get his advice on navigating post-exit life. Plus, we discuss philanthropy and finding purpose and fulfillment beyond financial success.

Guest

Dan Reich is an entrepreneur, investor, and philanthropist. He has co-founded Spinback (acquired by Buddy Media), Tula (acquired by Procter & Gamble), Dibs Beauty, and Troops.ai (acquired by Salesforce).

Links

Chapters

00:00 Intro 02:14 Dan's Journey 09:47 Venture Studios 13:16 Creators 22:40 Financing 25:44 Why Again? 28:01 Daily Routines 29:31 Post-Exit Emotions 40:49 Philanthropy 43:07 Angel Investing 44:59 Final Thoughts

Podcast

I am the ex-founder of Skillshare, and now exploring what's next. The Karnjanaprakorn Show (TKS) follows my journey as I share what I learn along the way, and chat with others who are taking unique approaches to business and life. Learn more about me: https://mikekarnj.com

#32: Geoff Roberts - Designing a Company Around Life Profitability

Michael Karnjanaprakorn — Tue, 28 May 2024 18:25:29 +0000

I chatted with Geoff Roberts about how they designed the company at Outseta, where they do things differently. Everyone makes $210,000 and can choose to work one to five days a week. They operate without budgets, targets, or OKRs, maintaining a flat hierarchy with no bosses. The company prioritizes life profitability for both the team and customers. Geoff discusses the motivation behind these decisions and how a high-trust, fully transparent work environment facilitates this unique culture.

Guest

Geoff is the co-founder of Outseta, an all-in-one membership software that makes it easier to build SaaS products, membership sites, and online communities. Learn more about their unique culture here.

Chapters

00:00 Intro

03:57 Bootstrapping

05:21 Ambition & Lifestyle

06:45 Life Profitability

13:52 $210,000 Salary

19:37 Flat Hierarchy

23:42 Resolving Conflicts

27:42 Attracting Talent

29:36 Lessons

32:18: Living Abroad

38:38 Advice

Podcast

I am the ex-founder of Skillshare, and now exploring what's next. The Karnjanaprakorn Show (TKS) follows my journey as I share what I learn along the way. Learn more about me: https://mikekarnj.com/

#31 - Repeat Founder Cycle

Michael Karnjanaprakorn — Tue, 21 May 2024 08:00:00 +0000

In this episode, I share the cycle many former founders go through as they decide between starting another company or riding off into the sunset.

Chapters

00:00 Intro

01:28 Founder Cycle

07:59 Redefining Success

Podcast

I am the ex-founder of Skillshare, and now exploring what's next. The Karnjanaprakorn Show (TKS) follows my journey as I share what I learn along the way. Learn more about me: https://mikekarnj.com/

#30 - Lifestyle Design

Michael Karnjanaprakorn — Tue, 14 May 2024 15:59:52 +0000

In this episode, I explore lifestyle design, a philosophy centered around creating a life that aligns with freedom, work-life integration, purposeful living, and income autonomy. I question the conventional path to success and explore examples of people who are doing it differently. And share steps on how you can design your own lifestyle.

Chapters

00:00 Intro

01:25 Core Principles

02:57 Examples

08:44 Reflection

Podcast

I am the ex-founder of Skillshare, and now exploring what's next. The Karnjanaprakorn Show (TKS) follows my journey as I explore ideas related to life, business, and technology.

Learn more about me here: https://mikekarnj.com/

#29: Ryan Sneddon - Building a Local Empire

Michael Karnjanaprakorn — Tue, 07 May 2024 14:53:43 +0000

I had a conversation with Ryan Sneddon, who has built a successful local email newsletter in Annapolis, Maryland. We discussed the playbook for building a local business empire, and we both pitched different business ideas in real estate and YouTube.

Guest

Ryan Sneddon runs Naptown Scoop, a local newsletter serving Annapolis, Maryland. He's built an audience of over 18,000 (nearly half the town's population) and is building a local empire.

Links

Ryan's Twitter: https://twitter.com/lifeof_scoop
Naptown Scoop: https://www.naptownscoop.com

Chapters

00:00 Intro 01:31 Local Newsletters 09:53 Local Business Empire 22:58 Real Estate Newsletter 40:10 YouTube 51:32 Internet

Podcast

After working in tech startups, I'm now exploring what's next. The Karnjanaprakorn Show (TKS) follows my journey as I explore ideas related to life, business, and technology.

#28 - My Failure Resume

Michael Karnjanaprakorn — Tue, 30 Apr 2024 13:52:38 +0000

In this episode, I share three career failures: not getting into business school, the failure of my first startup, and the ten pivots we went through at Skillshare.

READ

Failure Resume

PODCAST

After working in tech startups, I'm now exploring what's next. The Karnjanaprakorn Show (TKS) follows my journey as I explore ideas related to life, business, and technology.

CHAPTERS 00:00 Intro 01:06 Business School 02:35 By/Association 06:06 Pivots 09:40 Learnings

#27 - Tarpit Ideas

Michael Karnjanaprakorn — Tue, 23 Apr 2024 05:00:00 +0000

Tarpit ideas seem promising but trap founders in companies that are hard to scale. The first version of Skillshare was trapped. I also share a list of common tarpit ideas. Stay away from these!

CHAPTERS

00:00 Intro

02:33 Skillshare

06:02 List of Tarpit Ideas

READ MORE

Tarpit Ideas

PODCAST

The Karnjanaprakorn Show (TKS) is a podcast in which I explore ideas related to life, business, and technology.

#26 - Life Decisions

Michael Karnjanaprakorn — Tue, 16 Apr 2024 19:54:09 +0000

I compiled a list of my ten most important life decisions. There are many more, but these were the top decisions I made before I turned 40. I also share some thoughts on how to best make those decisions.

LIFE DECISIONS

Who should I marry?
Should I have children?
Where should I live?
Which career should I pursue?
How should I manage money?
What healthy habits should I adopt?
What calculated risks should I take?
What values and beliefs should I uphold?
Which relationships should I nurture and maintain
What hobbies and interests should I explore?

CHAPTERS

00:00 Intro

00:41 Life Decisions

03:09 Being Right

04:02 The Click

05:47 Reflecting

BLOG POSTS

Life Decisions

Being Right

The Click

#25 - Some Ideas about Business

Michael Karnjanaprakorn — Tue, 09 Apr 2024 15:50:51 +0000

In this solo episode, I share three ideas about business: 1) how to get to your first $100K, 2) playing a different game, and 3) impact.

CHAPTERS

00:00 Intro

00:30 Investing in Yourself

02:38 Metagame

06:53 Legacy

#24 - Some Ideas About Life

Michael Karnjanaprakorn — Tue, 02 Apr 2024 10:08:00 +0000

In this solo episode, I share four of my favorite blog posts from the past month. This episode aims to inspire you to rethink your approach to life, creativity, and what it means to be successful.

CHAPTERS

00:00 Intro

01:53 Craftsmanship

05:52 Success Addiction

09:27 Parent Stories

14:27 Assets

PODCAST

The Karnjanaprakorn Show is where I explore ideas across life, startups, and technology. As the former founder of Skillshare, I am now following my curiosity. This show follows that journey, exploring topics like longevity, emerging technologies, living a fulfilling life, and more.

#23: Ben Tossell - What Happens After You Sell Your Startup

Michael Karnjanaprakorn — Tue, 26 Mar 2024 04:00:00 -0100

In this episode, we discuss what happens after you sell your company. Ben sold his company to Zapier in 2021 for an undisclosed amount, but it was enough for Ben to retire from working. We discussed why he sold the company, what he did in the first year, and the wave of emotions he felt after selling the company. We also talked about how he spent the money and what he’s investing in today. I also picked his brain on how he’s building an AI Assistant.

GUEST

Ben Tossell writes an AI Newsletter, Ben’s Bites, and invests in early-stage AI startups. He was previously the founder of Makerpad, a no-code education site, which was acquired by Zapier. He also just launched a new community called Acquired Founders.

LINKS

PODCAST

The Karnjanaprakorn Show is where I explore ideas across life, startups, and technology. As the former founder of Skillshare, I am now following my curiosity as I figure out my next thing. This show follows that journey, exploring topics like longevity, emerging technologies, living a fulfilling life, and more.

CHAPTERS

00:00 Intro 12:49 Why Sell 19:16 First Year 25:07 Stay or Leave 35:19 Money, Spending, Investing 45:53 AI Executive Assistant

#22: Safwaan Kay - AI Hardware, Polyamory, and Buying Internet Brands

Michael Karnjanaprakorn — Tue, 19 Mar 2024 09:00:00 -0100

In this episode, we bring back Safwaan Kay to discuss trends in technology, culture, and business. We cover polyamory, AI wearables, and buying iconic internet brands.

GUEST

Safwaan Kay invests and incubates in emerging tech at Founders, Inc.

PODCAST

CHAPTERS

00:00 Intro

00:52 Polyamory

11:19 AI-Enabled Hardware

27:24 Buying Iconic Companies

#21: We Made It

Michael Karnjanaprakorn — Tue, 12 Mar 2024 04:00:00 -0100

We reached a big milestone today. We reached the top 1% of podcasts by publishing our 21st episode. In this episode, I'll share some lessons learned, along with the future direction of the podcast.

PODCAST

The Karnjanaprakorn Show is where I explore unique ideas across life, startups, and technology. As the former founder of Skillshare, I am now following my curiosity and going down intellectual rabbit holes. This show follows that journey, exploring topics like longevity, investing, emerging technologies, living a fulfilling life, and more.

HOST

#20: Herbert Lui - Designing Your Own Creative Process

Michael Karnjanaprakorn — Tue, 05 Mar 2024 05:00:00 -0100

My guest is Herbert Lui. I brought him on the podcast to talk about the creative process and developing a creative habit.

There is no one-size-fits all approach but there are common frameworks that everyone can follow. We cover a lot of topics including the four-step creative process, capturing ideas, quality vs quantity, and promoting your own work. We also dive deep into the inner working of his note-taking process that was inspired by Ryan Holiday.

Herbert has a very organized chaotic process which I can relate to and I’m sure many of you. If you can take one idea or tactic to apply to your own process then this will be worth you time.

GUEST

Herbert is the author of Creative Doing which is a collection of exercises, mental models, and true stories from artists to help you find your own unique creative process.

He is a writer an an editorial director. His editorial studio Wonder Shuttle works with companies such as Shopify, Twilio, and Skillshare, which is where I originally met him.

He is prolific and has many creative projects including the book The World According to Kanye which was featured in Hypebeast. And the host of Prologue where he talks with artists like Post Malone to talk about the early days of their creative journeys.

Links

CHAPTERS

00:00 - Intro 03:28 - Creative Process 10:07 - Quantity Over Quality 20:16 - Note-Taking Process 35:43 - Daily Blogging 44:51 - Promoting Your Work

PODCAST

The Karnjanaprakorn Show is a podcast where I explore novel ideas on the fringes. As the former founder of Skillshare, I am now following my curiosity while I figure out my next thing. This podcast follows that journey as I go down intellectual rabbit holes, exploring topics like longevity, philosophy, futuristic technologies, and more.

HOST

#19: Emi Gal — Reducing Cancer Risk

Michael Karnjanaprakorn — Tue, 27 Feb 2024 09:00:00 -0100

In this episode, I chat with Emi Gal who is the Founder/CEO of Ezra, which offers affordable MRI screenings to detect cancer. We talk about early cancer detection, longevity protocols, annual challenges, and technology advancements within healthcare. GUEST Emi Gal is the CEO/Founder of Ezra, an AI startup focused on creating a new way to screen for cancer using MRI & AI. LINKS For the Ezra story, go here. For the longevity protocols, go here CHAPTERS 00:00 - Introduction 02:47 - Ezra 20:38 - Longevity Protocols 29:06 - Exercise Routine 32:02 - Optimizing Biomarkers 48:56 - Annual Challenges 53:11 - Technology Trends PODCAST The Karnjanaprakorn Show is a journey into living a fulfilling life across all areas. I'm known to many as the founder of Skillshare or Otis. As I approached my 40th birthday, I experienced a mid-life transition and took a year-long sabbatical. This period led me to reassess my priorities. I realized that aspects I once valued — success, status, wealth — weren't as fulfilling and were detracting from other areas of my life, such as health and relationships. This insight prompted me to explore my passions and interests beyond work, including running, philosophy, and exploring the unknown, whether in the form of new ideas, people, or experiences. I look for novel ideas and share them through this podcast so join me on this journey! HOST ⁠⁠⁠⁠⁠⁠⁠⁠Michael’s newsletter⁠⁠⁠⁠⁠⁠⁠⁠ ⁠Twitter

#18: Yong-Soo Chung — Building a Personal Holding Company

Michael Karnjanaprakorn — Tue, 20 Feb 2024 05:00:00 -0100

In this episode, we discuss Personal Holding Companies (PHCs) that center on your personal interests, passions, and lifestyle. Yong-Soo shares his experiences and provides practical advice on how anyone can take a similar path. We also cover trends like AI and the development of healthy habits. The main takeaway from this discussion is that aligning your personal and business interests is very possible.

GUEST

Yong-Soo is a serial entrepreneur bootstrapping his business from $0 to $20m in over 8 years.

LINKS

CHAPTERS

00:00 - Intro 01:25 - PHC Philosophy 03:13 - New Playbook 05:43 - Audience Building 13:53 - Trends 18:19 - Habits

PODCAST

The Karnjanaprakorn Show is a journey into living a fulfilling life across all areas. I'm known to many as the founder of Skillshare or Otis. As I approached my 40th birthday, I experienced a mid-life transition and took a year-long sabbatical. This period led me to reassess my priorities. I realized that aspects I once valued — success, status, wealth — weren't as fulfilling and were detracting from other areas of my life, such as health and relationships. This insight prompted me to explore my passions and interests beyond work, including running, philosophy, and exploring the unknown, whether in the form of new ideas, people, or experiences. I look for novel ideas and share them through this podcast so join me on this journey!

HOST

⁠⁠⁠⁠⁠⁠⁠Michael’s newsletter⁠⁠⁠⁠⁠⁠⁠

Twitter

#17: Henrik Werderlin — Pursuing Interestingness over Goals

Michael Karnjanaprakorn — Tue, 13 Feb 2024 05:00:00 -0100

I chat with Henrik Werdelin (co-founder of Barkbox) about pursuing interests rather than goals for starting companies, based on the idea of open-endedness. We also talk about how Henrik using AI to crystalize his ideas, longevity protocols, and his 8+1 framework for life planning.

GUEST

Henrik Werdelin is an entrepreneur and author best known for co-founding Bark / Barkbox (NYSE Listed $BARK). As well as starting Prehype, a venture building research and development group headquartered in New York.

LINKS

CHAPTERS

00:00 - Intro

02:34 - Open-endedness

13:00 - Longevity

19:13 - 8+1 Framework

24:52 - Personalized Bedtime Stories

#16: Justin Duke — Buying Software Businesses

Michael Karnjanaprakorn — Tue, 06 Feb 2024 05:00:00 -0100

I was curious about buying software-based businesses so I reached out to Justin Duke who started Third South Capital. We talk about his journey from working at Stripe to starting his own company to acquiring five software companies.

GUEST

Justin Duke runs Buttondown and invests at Third South Capital. Before that, he spent four years at Stripe building data products. Here's his article on buying software businesses.

CHAPTERS

00:00 - Introduction

05:44 - Buying

16:27 - Challenges

22:45 - Advice

27:48 - Code

41:41 - Operations

42:24 - Sustainability

52:29 - Media Consumption

#15: Kevin Lee — Founder Operating System (OS)

Michael Karnjanaprakorn — Tue, 30 Jan 2024 14:50:06 -0100

I chat with Kevin Lee, Founder of immi, discussing everything from healthy ramen to productivity in both business and personal life. We delve deep in Kevin's journey of creating a low carb, high protein ramen, addressing health concerns within Asian communities, and personal productivity processes. GUEST Kevin Lee is a co-founder of immi, which invented the world's first low carb, high protein, and 100% plant based instant ramen. He previously led better-for-you food & beverage investing at Pear VC and is an angel investor in 40+ companies. He grew up working alongside his grandparents on their produce farms in Taiwan. Follow Kevin on ⁠Twitter⁠ Check out immi HOST Watch on ⁠⁠⁠⁠⁠⁠⁠⁠Youtube⁠⁠⁠⁠⁠⁠⁠ Subscribe to ⁠⁠⁠⁠⁠⁠⁠Michael’s newsletter⁠⁠⁠⁠⁠⁠⁠ Learn more about ⁠⁠⁠⁠⁠⁠⁠⁠Michael⁠⁠⁠ CHAPTERS 00:00 - Introduction 05:25 - Asian Culture and Nutrition 17:55 - Company OS 33:57 - Personal OS 44:44 - Life Dinner Concept 50:14 - Coffee Sobriety

#14: "One and Done" Round

Michael Karnjanaprakorn — Tue, 23 Jan 2024 05:00:00 -0100

Let's talk about startup fundraising. Why are startups so hard? What's the game that you play when you raise from a VC? What I would do if I were to start a company today?

CONNECT

Watch on ⁠⁠⁠⁠⁠⁠⁠⁠Youtube⁠⁠⁠⁠⁠⁠⁠
Subscribe to ⁠⁠⁠⁠⁠⁠⁠Michael’s newsletter⁠⁠⁠⁠⁠⁠⁠
Learn more about ⁠⁠⁠⁠⁠⁠⁠⁠Michael⁠⁠⁠

CHAPTERS

00:00 - Intro

00:48 - Why Startups are Hard

04:45 - The VC Game

09:55 - The One and Done Round

13:13 - Taking Money Off the Table

16:36 - Recap

#13: Myles Snider — Finding Purpose in the Kitchen

Michael Karnjanaprakorn — Tue, 16 Jan 2024 05:00:00 -0100

I chat with Myles Snider on finding your purpose or ikigai. We also explore his unique approach to cooking instruction that focuses on principles rather than recipes. We also talk about seed oils, ways to detoxify your kitchen, and why you shouldn't use plastic cutting boards. We end the show brainstorming a business idea around creating a healthier American burger joint.

GUEST

Myles Snider runs an online cooking school called 80/20 Cooking.

Follow Myles on Twitter
Follow Myles on Instagram
Follow Myles on TikTok

CONNECT

Watch on ⁠⁠⁠⁠⁠⁠⁠Youtube⁠⁠⁠⁠⁠⁠
Subscribe to ⁠⁠⁠⁠⁠⁠Michael’s newsletter⁠⁠⁠⁠⁠⁠
Learn more about ⁠⁠⁠⁠⁠⁠⁠Michael⁠⁠⁠

CHAPTERS

00:00 - Introduction

04:20 - Finding Purpose

20:45 - Salt

24:50 - Seed Oils

27:58 - Detoxifying Your Kitchen

32:01 - Unsolicited Advice

44:10 - Burger Joint

#12: Living Near Friends

Michael Karnjanaprakorn — Tue, 09 Jan 2024 11:14:00 -0100

I wrote my most viral tweet about the trend of friends moving next door to each other. In the tweet, I explore why I think this idea went viral, why more people aren't doing it, and different models of how you can live near your friends.

CHAPTERS

00:00 - Introduction 02:11 - Impact on Happiness 03:24 - Challenges 06:36 - Different Models 10:06 - My Thoughts 12:09 - Why Don't More People Do This?

CONNECT

Watch on ⁠⁠Youtube⁠

Subscribe to ⁠⁠Michael’s newsletter⁠⁠

Learn more about ⁠⁠⁠Michael⁠⁠

#11: System10: Upgrade your Personal OS

Michael Karnjanaprakorn — Tue, 02 Jan 2024 11:15:00 -0100

Rather than just setting goals, I’m trying something new this year around building a system.

It's called System10:

• One keystone habit per month • Each month builds on top of the previous one • Add 10 new habits and routines into my personal OS

I discovered this approach when I stopped drinking alcohol. It had such a positive ripple effect in so many others areas of my life. Goal now is to incorporate new habits and routines that create a lifestyle change.

CHAPTERS

00:00 - Introduction

00:54 - System 10

05:14 - Examples

06:05 - Flexibility

#10: 2023 Review & Lessons Learned

Michael Karnjanaprakorn — Tue, 26 Dec 2023 11:16:00 -0100

I review my year where I took sabbatical, quit drinking alcohol, and share my biggest unexpected surprise. I also share some important lessons that anyone can apply in their own lives, including collecting memory dividends.

00:00 - Introduction 03:37 - The Decade Goal 06:53 - Wisest Decision 08:06 - Lessons Learned 14:26 - 2024

#9: Kane Kallaway — Reaching 1B Views as a Creator

Michael Karnjanaprakorn — Tue, 19 Dec 2023 23:02:00 -0100

Kane Kallway is a content creator who has reached 1B views in less than a year. We thought it would be fun to do a "dual coaching" episode where we talk through challenges of building a personal holding company. I helped him think through monetization and he helped me think through content strategy. This episode is packed with the nitty gritty of what it's like to build a company.

GUEST

Instagram: / kanekallaway
Tiktok: / kanekallaway
YouTube: / @kallaway
Twitter: / kanekallaway
Blueprint (newsletter): https://www.espressoletter.com

CONNECT

Subscribe to ⁠⁠⁠⁠⁠Michael’s newsletter⁠⁠⁠⁠⁠
Watch on ⁠⁠⁠⁠⁠Youtube⁠⁠⁠⁠
Learn more about ⁠⁠⁠⁠⁠⁠Michael⁠⁠

CHAPTERS

00:00 - Introduction

01:30 - Personal Holding Company

07:58 - Challenges of Monetization

08:56 - Building a Content Engine

21:20 - Finding a Niche

40:15 - Rethinking Courses

48:59 - Exploring Business Ideas

AI Friends, Longevity Clinics & Living near Friends w/ Safwaan Kay

Michael Karnjanaprakorn — Tue, 12 Dec 2023 17:27:26 -0100

Episode #8: In this special edition of the show, we host our very first live episode with Safwaan Kay. We talk about what 20 year olds in SF and what 40 year olds are into right now.

CHAPTERS

00:00 - Introduction

01:23 - AI Friends

11:32 - Longevity Clinics

26:12 - Choosing Where to Live

CONNECT

Subscribe to ⁠⁠⁠⁠Michael’s newsletter⁠⁠⁠⁠
Watch on ⁠⁠⁠⁠Youtube⁠⁠⁠
Learn more about ⁠⁠⁠⁠⁠Michael⁠⁠

Ever wonder what it's like to have $100M?

Michael Karnjanaprakorn — Tue, 05 Dec 2023 23:02:00 -0100

Episode #7: In this episode, we dive into the life and lessons of 'Hector', a software engineer who accumulated a net worth over $125 million after his company went public in the 2010s. By summarizing a series of Hector's Reddit posts, we distill five key life lessons from his experiences.

CHAPTERS

00:00 - Introduction

00:33 - Background

01:59 - Lesson 1: Luck

03:37 - Lesson 2: Investment

04:56 - Lesson 3: Novelty

06:21 - Lesson 4: Time

07:26 - Lesson 5: Purpose

CONNECT

From Homeless to Multi-Million Dollar Sports Card Collection with Erik Myers

Michael Karnjanaprakorn — Tue, 28 Nov 2023 09:36:00 -0100

Episode #6: In this interview, Erik Myers takes us through his journey from experiencing homelessness to building a multi-million dollar sports card collection. He reveals how his past experiences, resilience, and mindset have shaped his success. He shares valuable life lessons and emphasizes the importance of continuous learning, self-belief, and service to others.

CHAPTERS

00:00 - Introduction 04:49 - Early Life and Challenges 09:26 - Struggles and Turning Point 20:42 - Growing the Card Collection 29:42 - Pivotal Moments and Big Moves 33:20 - Power of Self-Belief and Determination 38:08 - Importance of Self-Mastery 48:19 - Joy of Helping Others and Personal Growth 48:34 - Impact of Material Possessions on Character 52:59 - Plan for Future

CONNECT

Tech Optimism, AI Tutoring & Olipop (Tings Newsletter #16)

Michael Karnjanaprakorn — Tue, 21 Nov 2023 10:00:00 -0100

Episode #5: Every month, I write a newsletter called Tings. It consists of 20 bulleted points on random ideas. In this episode, I decided to provide some commentary behind each point.

Here's the AI-written description: "A new episode of The Karnjanaprakorn Show where the host explores his latest newsletter. He shares thoughts on a variety of topics, and gives some backstory and commentary about why he included certain links and bullet points. Key topics include 'tech optimism', potential of AI-based tutors, new productivity tools, a critical review on a popular health drink ID'd as 'Olipop', book recommendations, and discussions on the concept of manhood. The host also shares his perspective on global progress, his belief in universal basic income and the need to optimize time. The overall conversation balances productivity hacks, health tips, future trends, and philosophical discussions."

CONNECT

Subscribe to ⁠⁠⁠⁠Michael’s newsletter⁠⁠⁠⁠
Watch on ⁠⁠⁠⁠Youtube⁠⁠⁠
Learn more about ⁠⁠⁠⁠⁠Michael⁠⁠

Protocol Daddies with Johnny Bowman

Michael Karnjanaprakorn — Tue, 14 Nov 2023 22:41:21 -0100

Episode #4: We talk about “protocol daddies” like Andrew Huberman, explore the archetype for the right male role model, and how emotional intelligence fits into that.

GUEST

Johnny Bowman is the co-lead the Brooklyn Chapter of All Kings, a men's group focused on supporting formerly incarcerated men.

CHAPTERS

00:00 Intro

01:53 Physical Health

11:03 Protocol Daddies

25:00 Men’s Groups

41:45 Creating a Life Mission

57:00 Active Listening

LINKS FROM THE SHOW

Johnny’s ⁠newsletter⁠:
Johnny’s ⁠course for men’s emotional intelligence⁠ ($50 discount)
⁠Summary of Health Stuff⁠

CONNECT

Creativity

Michael Karnjanaprakorn — Tue, 07 Nov 2023 22:56:00 -0100

Episode #3: I asked AI to write this episode’s description. Here it is! “My journey grappling with societal labels and feeling pigeonholed into certain roles due to these labels. I stress the importance of not allowing societal labels to dictate who you are, embracing your creative side, and carving out your own unique path. I use the analogy of the 'Second Mountain' to explain my shift from focusing on self-definition to nurturing my creative expression. I also share my vision for creating a personal holding company focused on creative projects that balance personal expression with societal benefit.”

CHAPTERS 00:00 Introduction 00:47 Labels and Societal Expectations 02:52 Balancing Creativity and Business 04:56 Repressing Creativity 05:23 First and Second Mountain 06:18 Personal Holding Company 10:14 Lessons Learned

LINKS Subscribe to ⁠Michael’s newsletter⁠

Learn more about ⁠Michael⁠

Midlife Transition with Ryan Vaughn

Michael Karnjanaprakorn — Tue, 31 Oct 2023 18:24:25 -0100

Episode #2: I chat with Ryan Vaughn about midlife transitions, letting go of externally created identities, and the role of psychedelics in self-discovery.

GUEST

Ryan Vaughn is a founder/executive coach at ⁠Inside Out Leadership

CHAPTERS

00:00 - Introduction

01:27 - Motivation

02:52 - Midlife Transition

03:45 - Identity Shifts

11:32 - Phases

15:34 - Transitions

20:39 - Ego

24:09 - Psychedelics

36:36 - Relationships

LINKS FROM THE SHOW

Ryan's article on the ⁠Midlife Reorientation⁠

CONNECT

Subscribe to ⁠Michael’s newsletter⁠

Watch on ⁠Youtube

Learn more about ⁠⁠Michael⁠⁠

Sabbatical

Michael Karnjanaprakorn — Mon, 23 Oct 2023 11:53:51 +0000

Episode #1: Over the past 365 days, I've been on a sabbatical. Intentionally doing absolutely nothing. That was really hard for me. But taking time off to do nothing was also one of the best things I ever did. I reflect on the year and talk about reprioritizing my life and going through an identity shift.

00:00 Intro

04:32 Five Regrets of the Dying

05:41 Second Mountain

09:49 The Karnjanaprakorn Show