#089 David Senra + Mitchell Baldridge #6 : Writing the Founders’ Book, Building Natural-fit Businesses, and Craft
Topics:
(00:00:00) - Intro
(00:03:52) - The Founder's book project
(00:04:06) - Effort and building relationships
(00:11:20) - The value of self-publishing
(00:24:00) - Bootstrapping a HoldCo
(00:46:05) - Finding natural fit in business
(00:47:48) - The role of trust in business
(00:49:07) - AI and changing perspectives
(00:50:26) - Daily use of AI tools
(00:55:49) - The value of deep research
(00:57:53) - The future of AI in business
(01:16:35) - Avoiding addictive apps
(01:18:27) - Collecting and using maxims
(01:20:45) - The power of lists
(01:24:40) - Collapsing organizational gaps
(01:28:05) - The role of AI in reducing friction
(01:29:59) - Closing remarks and recommendations
Links:
Andrew Wilkinson — https://twitter.com/awilkinsonDavid Senra — https://twitter.com/founderspodcastEric Jorgenson — https://twitter.com/ericjorgensonMitchell Baldridge — https://twitter.com/baldridgecpaNick Huber — https://twitter.com/sweatystartup
Eric Jorgenson — https://ejorgenson.com
Founders Podcast — https://www.founderspodcast.com
Better Bookkeeping — https://www.betterbookkeeping.comRE Cost Seg — https://www.recostseg.comScribe — https://scribemedia.com
To support the costs of producing this podcast:
>> Buy a copy of the Navalmanack: www.navalmanack.com/
>> Buy a copy of The Anthology of Balaji: https://balajianthology.com/
>> Sign up for my online course and community about building your Personal Leverage: https://www.ejorgenson.com/leverage
>> Invest in early-stage companies alongside Eric and his partners at Rolling Fun: https://angel.co/v/back/rolling-fun
>> Join the free weekly email list at ejorgenson.com/newsletter
>> Text the podcast to a friend
>> Or at least give the podcast a positive review to help us reach new listeners!
We discuss:
How extreme effort and agency created the opportunity to publish the Founders' book.
The economics, longevity, and cultural value of self-published books.
Bootstrapping and scaling a HoldCo with multiple service businesses.
Practical uses of AI for research, productivity, and creative leverage.
The importance of doing the work for its own sake and loving the process.
Quotes from David:
“You don’t handle the stress—you like it. Or else you wouldn’t be doing this.”
“If you want the ups, you have to endure the downs. That’s just a fact.”
“This is the best version of my life, whether it’s 300 people at a club or 3,000 in a theater.”
“Most people try to keep things even—no extreme highs or lows. But all the exciting shit is in the variance.”
“If you have something else you’d rather be doing, then you should go do that.”
“Books are so valuable because of how long they take to consume.”
“Effort is universal. Doesn’t matter if it’s a garden or a podcast—people respect work.”
“AI is going to wipe out the middle. If you’re average, you’re gone.”
“Sage remembers things I don’t—and that’s priceless.”
“Don’t rush it. Make something great. A good book can sell for 50 years.”
Quotes from Mitchell:
“I get frustrated at how long this takes—but I want to build something meaningful.”
“Turn everything into a car wash. Put the customer into neutral and pull them through.”
“The tax code is getting more complex, but the systems are getting better.”
“AI is going to destroy everything below the 95th percentile.”
“I’m bootstrapping a holdco—and it takes time.”
“Send me a customer, I’ll give you $1,000. Send me 1,000 and I’ll mortgage my house for you.”
“I don’t want 25 meetings a month—I want results.”
Topics:
(00:00:00) - Intro
(00:03:45) - Who are your heroes?
(00:05:16) - What is something you’ve had to teach yourself that’s become a core part of your identity?
(00:07:34) - Taking a sabbatical post-exit
(00:09:30) - Going back into entrepreneurship
(00:12:52) - How to kill two-factor auth
(00:14:34) - When to split a company into two companies
(00:18:04) - Who is the customer of iDeem?
(00:22:37) - Verified Credentials
(00:28:31) - Fighting fraud with technology
(00:30:14) - The story of eyeVerify
(00:49:09) - The new technology trends pushing iDeem
(00:52:01) - The build process of a global start-up from Middle-America
Links:
Ideem - https://www.useideem.com/
Toby on X - https://x.com/TobiasRush
Toby on LinkedIn - https://www.linkedin.com/in/tobiasrush/
To support the costs of producing this podcast:
>> Buy a copy of the Navalmanack: www.navalmanack.com/
>> Buy a copy of The Anthology of Balaji: https://balajianthology.com/
>> Sign up for my online course and community about building your Personal Leverage: https://www.ejorgenson.com/leverage
>> Invest in early-stage companies alongside Eric and his partners at Rolling Fun: https://angel.co/v/back/rolling-fun
>> Join the free weekly email list at ejorgenson.com/newsletter
>> Text the podcast to a friend
>> Or at least give the podcast a positive review to help us reach new listeners!
We discuss:
Why tying your identity to your company can be both a strength and a liability
The critical decision to shut down a beautiful but unused blockchain product—and return investor money
How trusted digital IDs could change how we prove who we are—from checking out online to entering a secure facility
Why simply having a trusted device could be a stronger way to log in and why invisible two-factor might be the future
What it’s like to run a global fintech startup from Kansas City and the cultural learnings that come with it
Quotes from Toby:
“When the company is dying, that doesn’t mean I’m dying. And when it’s thriving, that doesn’t mean I’m a good person.”
“You should absolutely take a window of time when one chapter ends—just having time to yourself is all the justification you need.”
“Two-factor authentication is alive and well—it’s just invisible now.”
“We reduce friction for the user, fraud for the merchant, and cost for everyone.”
“If you’re serving two totally different customers with one product, you probably have two companies.”
“The magic moment is at checkout—remove friction there and everything gets better.”
“Passwords are terrible. If I can just look at my phone and log in, that’s a win.”
“You need friends who can sing your soul’s song back to you when you’ve lost the melody.”
“From almost out of money to a $100 million term sheet in five weeks—that’s the startup rollercoaster.”
“Authenticity, credibility, and trust are incalculable in value.”
“If the thesis is right but the timing is off, you can build something beautiful that no one uses.”
“Stop with the techno-babble. We won’t call them NFTs—we’ll just call them useful.”
Important Quotes from the podcast on Business and Entrepreneurship
There is no skill called “business.” Avoid business magazines and business classes. - Naval Ravikant
You have to work up to the point where you can own equity in a business. You could own equity as a small shareholder where you bought stock. You could also own it as an owner where you started the company. Ownership is really important.
Everybody who really makes money at some point owns a piece of a product, a business, or some IP. That can be through stock options if you work at a tech company. That’s a fine way to start.
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1:02:52
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1:02:52
#087 Nat Eliason: From Blogging to Sci-Fi Novels, Writing Books That Last, and Owning Your Audience
Topics:
(00:00:00) - Intro
(00:00:45) - Introducing Nat Eliason
(00:01:27) - Nat's Diverse Career and Writing Journey
(00:01:47) - The Transition from Nonfiction to Fiction
(00:02:13) - The Seven Act Structure and Writing Process
(00:02:44) - Publishing with Scribe and Launching Husk
(00:03:24) - The Rewards and Challenges of Writing
(00:04:29) - Building an Audience and Marketing Strategies
(00:06:54) - Balancing Writing with Other Ventures
(00:09:09) - The Reality of a Writing Career
(00:10:49) - The Importance of Consistency and Commitment
(00:22:37) - Navigating Traditional and Self-Publishing
(00:23:05) - The Journey to Becoming an Author
(00:40:56) - Exploring the Shift from Nonfiction to Fiction
(00:41:40) - The Joy of Storytelling in Fiction
(00:44:00) - Challenges and Rewards of Writing Fiction
(00:47:44) - Outlining and Structuring Fictional Works
(00:57:38) - Marketing and Selling Self-Published Books
(01:10:38) - The Future of an Author's Career
(01:18:18) - Conclusion and Recommendations
Links:
Nat on X
Nat’s Website
Crypto Confidential
Husk
To support the costs of producing this podcast:
>> Buy a copy of the Navalmanack: www.navalmanack.com/
>> Buy a copy of The Anthology of Balaji: https://balajianthology.com/
>> Sign up for my online course and community about building your Personal Leverage: https://www.ejorgenson.com/leverage
>> Invest in early-stage companies alongside Eric and his partners at Rolling Fun: https://angel.co/v/back/rolling-fun
>> Join the free weekly email list at ejorgenson.com/newsletter
>> Text the podcast to a friend
>> Or at least give the podcast a positive review to help us reach new listeners!
Important Quotes from the podcast on Business and Entrepreneurship
There is no skill called “business.” Avoid business magazines and business classes. - Naval Ravikant
You have to work up to the point where you can own equity in a business. You could own equity as a small shareholder where you bought stock. You could also own it as an owner where you started the company. Ownership is really important.
Everybody who really makes money at some point owns a piece of a product, a business, or some IP. That can be through stock options if you work at a tech company. That’s a fine way to start.
Quotes from Nat:
“Writing is the one thing I love doing enough to commit to for the next 30 years.”
“Traditional publishing taught me how to make a really good book, but I wouldn’t do it again.”
“Holding your book for the first time—and shipping it yourself to your first readers—is pure magic.”
“The best marketing for your book is writing the next one—that’s the fiction game.”
“I used to chase whatever was interesting… now I’m building something I want to last 30 years.”
“Fiction lets me explore big ideas without pretending to be an expert.”
“The self-pub stigma is fading… especially when the book looks and reads like a trad pub hit.”
“Characters start doing things I didn’t plan—then I realize, oh, that’s why they’re here.”
“There’s no product in the world like a book—you can sell the same file for 50 years.”
“My dream is to have a warehouse full of books I wrote. That’s the romantic version of success.”
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1:20:14
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1:20:14
#086 Jim O’Shaughnessy: Learning to Learn, AI Disruption, and the Future of Publishing
Topics:
(00:00:00) - Intro
(00:03:30) - What’s the most important thing you’ve ever learned?
(00:07:23) - Learning to Learn
(00:11:20) - How learning changes as you age
(00:18:51) - How do you think about your circle of competence?
(00:22:21) - The future of book publishing and how authors adapt
(00:35:29) - AI disruption in book publishing
(00:47:56) - Jim’s inaugural book: Two Thoughts
(00:56:46) - LLMs for authors, and UBI
Links:
Jim on X
Infinite Loops Podcast
Infinite Books
O’Shaughnessy Ventures
Margins: Book Tracker
To support the costs of producing this podcast:
>> Buy a copy of the Navalmanack: www.navalmanack.com/
>> Buy a copy of The Anthology of Balaji: https://balajianthology.com/
>> Sign up for my online course and community about building your Personal Leverage: https://www.ejorgenson.com/leverage
>> Invest in early-stage companies alongside Eric and his partners at Rolling Fun: https://angel.co/v/back/rolling-fun
>> Join the free weekly email list at ejorgenson.com/newsletter
>> Text the podcast to a friend
>> Or at least give the podcast a positive review to help us reach new listeners!
Here’s what we explored in the episode:
"The most important thing I learned was how to learn and unlearn... most people are never taught it. It is something that, almost by definition, you have to do yourself."
It’s important for leaders to admit when they are uncertain, and lead a culture of open-mindedness.
It’s important to adapt to new environments, not cling to outdated practices.
There’s an upcoming shift toward AI-driven, author-friendly publishing models that reduce inefficiencies and empower writers.
Jim predicts AI will allow a “tsunami of slop” content and open huge opportunities in curation.
In a world of abundant content, good taste and effective curation will be very profitable.
Jim shares his evolving views on Universal Basic Income (UBI), arguing for experimentation to address societal shifts caused by technological advancements.
Understanding opposing viewpoints to refine one's perspectives helps make better decisions. Jim uses AI to force him to debate and understand his own opinions better.
Jim credits his success to a lifelong commitment to curiosity, whether through broad reading or questioning established norms.
"Curiosity is a shit starter. It ignited my curiosity to the point where I just voraciously read everything."
Important Quotes from the podcast on Business and Entrepreneurship
There is no skill called “business.” Avoid business magazines and business classes. - Naval Ravikant
You have to work up to the point where you can own equity in a business. You could own equity as a small shareholder where you bought stock. You could also own it as an owner where you started the company. Ownership is really important.
Everybody who really makes money at some point owns a piece of a product, a business, or some IP. That can be through stock options if you work at a tech company. That’s a fine way to start.
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1:07:49
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1:07:49
#085 Ben Reinhardt: How to Discover New Technology, Playing the Longest Game, and Philanthropy in Technology
Topics:
(00:00:00) - Intro
(00:05:25) - Studying both Medieval History and Engineering
(00:09:48) - Founding Speculative Technologies
(00:11:25) - Defining “Useful” in Science and Technology
(00:13:46) - Building the roadmap of discoveries to unlock futuristic tech
(00:17:24) - The need for new institutions
(00:25:22) - Why focus on material science and manufacturing technologies
(00:46:57) - The day-to-day work and impact of Speculative Technologies
Links:
Speculative Technologies
Ben on X
Ben’s website
To support the costs of producing this podcast:
>> Buy a copy of the Navalmanack: www.navalmanack.com/
>> Buy a copy of The Anthology of Balaji: https://balajianthology.com/
>> Sign up for my online course and community about building your Personal Leverage: https://www.ejorgenson.com/leverage
>> Invest in early-stage companies alongside Eric and his partners at Rolling Fun: https://angel.co/v/back/rolling-fun
>> Join the free weekly email list at ejorgenson.com/newsletter
>> Text the podcast to a friend
>> Or at least give the podcast a positive review to help us reach new listeners!
Here’s what we explored in the episode:
How studying history helps us see the present and the future more clearly.
Ben’s vision is to work with founders who are not just chasing profits but are driven by the desire to solve meaningful problems.
Most successful concepts emerge from multiple rounds of experimentation.
As institutions evolve, gaps formed around important research that used to be funded by universities or R&D labs of corporations. Ben is building a non-profit to fill that gap.
Ben shared why he chose to invest in startups rather than founding his own.
Ben invests in "physics-enabled" startups that apply scientific principles to solve tough problems.
For startups to be successful, there needs to be an alignment of motivations between investors and founders.
Founders should approach investors with clarity about their vision and expect honesty and support in return.
There are significant global issues that aren't being addressed by startups and opportunity abounds.
Leaders must build complementary teams where members fill each other’s gaps, particularly in technical and strategic expertise.
There’s a need for effective communication to bridge gaps between technical experts and the broader public. (hopefully some of what we’re doing here!)
If you’re looking for non-profit causes for your philanthropic donations, SpecTech may be among the highest-leverage ways to advance human civilization through donations.
Important Quotes from the podcast on Business and Entrepreneurship
There is no skill called “business.” Avoid business magazines and business classes. - Naval Ravikant
You have to work up to the point where you can own equity in a business. You could own equity as a small shareholder where you bought stock. You could also own it as an owner where you started the company. Ownership is really important.
Everybody who really makes money at some point owns a piece of a product, a business, or some IP. That can be through stock options if you work at a tech company. That’s a fine way to start.
Casual conversations with founders, technologists, investors, and artists about building a brighter future, together. Welcome to our digital living room.
With science, technology and entrepreneurship we can *continue* to create unfathomable leaps in quality of life. We show you how to find, apply, build, and invest in technologies to change your life and the world.
When we have smart friends, we do smart things. When we do smart things, we save the world.
No matter who, where, or when you are – now you have smart friends, too.
Outside this podcast, I’m the author of The Almanack of Naval Ravikant and The Anthology of Balaji. Connect at ejorgenson.com
Laugh and learn with people like Balaji Srinivasan, Naval Ravikant, Andrew Wilkinson, Austen Allred, David Senra, Josh Storrs Hall, Ashley Rindsberg, Zach Pettet, Bret Kugelmass, Omar ElNaggar, Grace Guo, Brett Kopf, Max Olson, Chris Williamson, Shane Mac, Tim Hwang, David Perell, Jason Hitchcock, Natalia Karayaneva, Sebastian Marshall, Taylor Pearson, Mitchell Baldridge and more.
Join conversations with my partners in early-stage tech investing, Bo Fishback and Al Doan. Our Rolling Fun Episodes cover our investments and escapades as angel investors and startup helpers. We invest in startups creating the *next* industrial revolution. Learn more at rolling.fun
“Surround yourself with people who remind you more of your future than of your past.”
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