The Startup Ideas Podcast

Greg interviews Nathan Barry, founder of ConvertKit, which makes email, automation, and monetization tools for creators.  

They talk about how to be interesting online, and different ways to monetize online content.

  
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creators and commerce. You'll also find out when new and exclusive  
episodes come out from Where it Happens. And it's totally free.  
  
https://latecheckoutstudio.ck.page/
  
FIND ME ON SOCIAL:  
Twitter: https://twitter.com/gregisenberg  
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LINKS FOR THIS EPISODE:  
Production Team:  
https://PodFlow.com
Nathan Bary
https://twitter.com/nathanbarry
https://ConvertKit.com
http://nathanbarry.com
  
SHOW NOTES:  
00:45 How to be interesting online

02:30 Combining education and entertainment

04:00 Storytelling for mundane stories

06:00 Improving comedy/storytelling skills

15:00 Video content spreads well

17:15 Studying comedy

19:30 Blending journeys and storytelling

21:45 Hiring out comedians

24:15 Learning monetization skills

27:00 Considering scalable business models

29:15 Running companies long-term

31:15 Building "skyscraper" products

34:00 Blending agencies and software

I'm joined by investor and entrepreneur Anthony "Pomp" Pompliano. Pomp hosts The Pomp Podcast, with over 50 million downloads, and writes a daily letter read by 250,000+ investors.

We talk about Pomp's approach to building resilient media properties, thinking long-term, and his best book recommendations for internet business success.

►►Subscribe to my weekly newsletter for insights on community, creators and commerce. You'll also find out when new and exclusive episodes come out from Where It Happens. And it's totally free.

https://latecheckout.substack.com

FIND ME ON SOCIAL
Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
TikTok: https://tiktok.com/@gregisenberga

BOOKS POMP MENTIONED

Unreasonable hospitality by John O'Leary

The Successor by Lachlan Murdoch

The 50th Law by Robert Greene and 50 Cent

Zero to One by Peter Thiel

Suleiman Ollian by Anonymous

How to Get Rich by Felix Dennis

Losing My Virginity by Richard Branson

The Rise and Fall of American Growth by Robert J. Gordon

Hidden Genius by Polina Marinova

The Outsiders by Will Thorndike

Elon Musk by Walter Isaacson

Urgency by John P. Kotter

The War of Art by Steven Pressfield

Good Profit by Charles Koch

LINKS FOR THIS EPISODE

Production Team: https://podflow.com
Pomp on Twitter: https://twitter.com/APompliano
Pomp on YouTube: https://www.youtube.com/c/anthonypompliano
Pomp's newsletter: https://pomp.substack.com

SHOW NOTES

1. 0:15 - Anthony's provocative dinners for hidden beliefs
2. 01:45 - Climate change evidence not as compelling
3. 02:30 - Scarcity of unique perspectives in newsletters
4. 03:00 - Click rates over open rates for engagement
5. 03:45 - Media as repetitive software
6. 04:15 - Bay Area Times' visual newsletters
7. 05:15 - Unique Bitcoin perspective in Truth for the Commoner
8. 06:00 - Bay Area Times' rapid growth
9. 07:00 - Open rates for brand awareness, click rates for direct response
10. 08:15 - Agora's focus on ecommerce conversions
11. 10:15 - Monetization through hedge funds
12. 11:15 - Joe Rogan's podcast profitability
13. 14:00 - Bay Area Times' positive industry news
14. 15:00 - Profitability before monetization for Bay Area Times
15. 18:15 - Small teams and revenue for entrepreneurs
16. 20:15 - Small teams for greater profitability
17. 21:15 - Studying media greats like Rupert Murdoch
18. 26:15 - Podcasts for expertise sharing
19. 29:00 - Economic freedom and financial security
20. 32:00 - Impactful employment business
21. 33:00 - Small acts making the world better
22. 34:45 - Pomp's book recommendation  

Today Greg is joined by New York Times Best-Selling Author, and Instagram Celebrity Yung Pueblo, whose real name is Diego Perez. In this episode, Greg and Diego talk about building an audience through meaningful writing, turning it into books, and using that influence to build companies that expand the vision expressed in writing that got it all started. 

►►Subscribe to Greg's weekly newsletter for insights on community,
creators and commerce. You'll also find out when new and exclusive
episodes come out from Where It Happens. And it's totally free.

https://latecheckout.substack.com

FIND ME ON SOCIAL
Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
TikTok: https://tiktok.com/@gregisenberga

LINKS FOR THIS EPISODE
Production Team:
https://podflow.com
Diego Perez / Yung Pueblo:
https://yungpueblo.com
http://instagram.com/yung_pueblo

SHOW NOTES
02:45 - What compassionate venture means.
06:01 - How he thinks of each of his businesses - books, social media and venture capital
09:19 - How he thinks about building on other social platforms versus email?
12:45 - Comparing his business's structure to other writers' structures.
16:00 - Social media entrepreneurs he looks up to.
18:47 - Should I write a book?
21:54 - A comparison of getting published and self-publishing.
25:04 - The importance of the pen name Young Pueblo.
40:00 - How to learn meditation.

Today Greg is joined by Jay Clouse of Creator Science. In this episode, Greg and Jay talk about the upsides of cohort-based courses and what strategies Jay uses to achieve his 95% retention rate. 

►►Subscribe to Greg's weekly newsletter for insights on community,
creators and commerce.You'll also find out when new and exclusive
episodes come out from Where it Happens. And it's totally free.

https://latecheckout.substack.com

FIND ME ON SOCIAL:
Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
TikTok: https://tiktok.com/@gregisenberga

LINKS FOR THIS EPISODE:
Production Team:
https://www.bigoceanpodcasting.com
Jay Clouse
https://twitter.com/jayclouse
https://creatorscience.com/

SHOW NOTES
0:00 - Intro
5:40 - How Jay studies top creators 
12:10 - Courses vs. Membership Community
19:30 - How Jay attracts audiences
24:20 - The secret dividends of viral posts
30:40 - Being a distributor vs. being an artist
43:30 - Why retention is the golden metric

Today Greg is joined by Julien Smith, the CEO of Practice, bestselling author of The Flinch, and executive coach. In this episode, Greg and Julien talk about the podcasts, books, and x/twitter feeds that entrepreneurs should be reading and following. They also explore why you should think of your life in seven-year increments. 

►►Subscribe to Greg's weekly newsletter for insights on community,
creators and commerce.You'll also find out when new and exclusive
episodes come out from Where it Happens. And it's totally free.

https://latecheckout.substack.com

FIND ME ON SOCIAL:
Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
TikTok: https://tiktok.com/@gregisenberga

LINKS FOR THIS EPISODE:
Production Team:
https://www.bigoceanpodcasting.com
Julien Smith
https://twitter.com/julien
http://juliensmith.com/

SHOW NOTES:
0:00 - Intro
7:27 - The Silicon Valley info diet
13:47 - The network multiplier of high quality content
20:35 - How to play the content long-game
30:56 - Think of you life in 7-year increments

Today Greg is joined by Michael Girdley--who's spent the last 30 years building a $100M+ holding company. In this episode, Greg and Michael talk about whether holding companies should take sexy VC money and how to be a decades-long player in a world of base hitters. 

►►Subscribe to Greg's weekly newsletter for insights on community,
creators and commerce.You'll also find out when new and exclusive
episodes come out from Where it Happens. And it's totally free.

https://latecheckout.substack.com

FIND ME ON SOCIAL:
Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
TikTok: https://tiktok.com/@gregisenberga

LINKS FOR THIS EPISODE:
Production Team:
https://www.bigoceanpodcasting.com
Michael Girdley
https://twitter.com/girdley
https://girdley.com/

SHOW NOTES:
0:00 - Intro
4:32 - Finding great businesses to buy
7:22 - Does Michael think Greg made a mistake by turning down $30M?
15:15 - Do this one thing before making a big decision
25:27 - Scalepath, EverthingMarketplaces.com, Reforge and other companies doing communities right
33:15 - The story behind Alamo Fireworks
44:58 - How Michael Girdley is playing the long game

Today Greg is joined by Phil Toronto, a Partner at Vayner/RSE. In this episode, Greg and Phil share their biggest cheat codes for saying 'yes' to the right kind of events and why being the person who brings others together is the biggest value add of all. 

►►Subscribe to Greg's weekly newsletter for insights on community,
creators and commerce.You'll also find out when new and exclusive
episodes come out from Where it Happens. And it's totally free.

https://latecheckout.substack.com

FIND ME ON SOCIAL:
Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
TikTok: https://tiktok.com/@gregisenberga

LINKS FOR THIS EPISODE:
Production Team:
https://www.bigoceanpodcasting.com
Phil Toronto
https://twitter.com/philtoronto

SHOW NOTES:
0:00 - Intro
5:16 - Say 'no' to networking events
11:06 - Greg says 'yes' to a Tony Robbins event
23:06 - The power of proximity to a big cultural events
27:00 - Be the host

Today Greg is joined by Nick Huber. In the last 9 months, Nick has co-founded 6 companies in addition to Bolt Storage. In this episode, Nick and Greg break down the inner workings of a personal holding company and how to grow it at max speed with minimal risk. 

►►Subscribe to Greg's weekly newsletter for insights on community,
creators and commerce.You'll also find out when new and exclusive
episodes come out from Where it Happens. And it's totally free.

https://latecheckout.substack.com

FIND ME ON SOCIAL:
Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
TikTok: https://tiktok.com/@gregisenberga

LINKS FOR THIS EPISODE:
Production Team:
https://www.bigoceanpodcasting.com
Nick Huber
https://sweatystartup.com/

SHOW NOTES:
0:00 - Intro
3:23 - Twitter as a network accelerant 
8:15 - Personal Holding Companies 101
12:10 - Buy vs. Build
20:22 - Nick asks Greg for constructive feedback
26:39 - Avoid mental overload as a multipreneur
30:27 - Substack vs. ConvertKit

Today Greg is joined by Chris Hutchins, the host of All the Hacks, a podcast to upgrade your life, money, and travel. In this episode, Greg and Chris talk about the best reason to start a podcast and how to grow it way beyond sponsorship revenue. 

►►Subscribe to Greg's weekly newsletter for insights on community,
creators and commerce.You'll also find out when new and exclusive
episodes come out from Where it Happens. And it's totally free.

https://latecheckout.substack.com

FIND ME ON SOCIAL:
Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
TikTok: https://tiktok.com/@gregisenberga

LINKS FOR THIS EPISODE:
Production Team:
https://www.bigoceanpodcasting.com
Chris Hutchins
https://www.allthehacks.com/

SHOW NOTES:
0:00 - Intro
4:15 - How to launch a successful podcast
14:00 - How to think about listener data
21:03 - How to "hack" a profitable media company
37:19 - Social strategies for podcasters

Today Greg is joined by Nicolas Cole, the co-founder of Ship 30 for 30, a daily writing challenge. In this episode, Greg and Nicolas talk about how much money it really takes to be free and why it's better to be anonymously rich than it is to be internet famous with no customers. 

►►Subscribe to Greg's weekly newsletter for insights on community,
creators and commerce.You'll also find out when new and exclusive
episodes come out from Where it Happens. And it's totally free.

https://latecheckout.substack.com

FIND ME ON SOCIAL:
Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
TikTok: https://tiktok.com/@gregisenberga

LINKS FOR THIS EPISODE:
Production Team:
https://www.bigoceanpodcasting.com
Nicolas Cole:
https://www.ship30for30.com/
https://twitter.com/Nicolascole77

SHOW NOTES:
0:00 - Intro
4:37 - Someone somewhere is working harder than you
12:48 - A mental model for competition
20:32 - How much money does it take to be "rich"?
30:51 - Status games