The Roundabout Entrepreneur

Lately, three materials have been filling my free time. These three materials have one theme tying them together, although ironically, for some of the materials, in a roundabout way. This theme is the idea of the roundabout as Mark Spitznagel calls it in The Dao of Capital.

The gospel of this book, which should be obvious by now, is the strategic advantage gained in the roundabout way

The Berkshire Hathaway Annual Letters

I spent the last few months reading every annual letter Warren Buffett wrote for Berkshire Hathaway going back to 1965. The reasons I did this were two-fold.

The first is that there is a lot of talk surrounding what Warren Buffett did, does, says, and said in investment circles, and I figured I’d get it straight from the horse’s mouth given how often his verbiage is quoted. I’d also been watching all the previous annual meetings that had been recorded on YouTube so I was already a follower and to some mild extent a practitioner.

While I’m on this point, I’ll mention that since reading his letters I’ve seen a great deal of misinformation spread from people who don’t know anything about Buffett’s approach. I often see things he stated in letters years ago taken out of context to support an investment thesis that Buffett would not approve of. As an aside, this is one of the most underrated advantages of learning. The more you learn, the more you realize how full of shit other people can be. Smelling bullshit is imperative to success, but I digress.

The second is, Warren Buffett is a legendary investor. It seems reasonable that if you want to achieve an even remote amount of his success, learning everything you can from him would be beneficial. As they say, “shoot for the moon, land on the stars”. This same approach is what led me to be accepted to the Berklee College of Music when trying to be accepted to Juilliard or to accept an offer from Amazon when trying to get into Google.

One of the important things you’ll uncover in these letters is Buffett’s patient, methodical, and disciplined approach to his early insurance business. Year after year in the early letters he states that other insurance businesses are chasing returns and that Berkshire’s insurance business will not write business that doesn’t make financial sense just because the other firms are doing it. Berkshire’s insurance business was more than willing to sit and do nothing for some years while in business.

It is our policy not to lay off people because of the large fluctuations in work load produced by such voluntary volume changes. We would rather have
some slack in the organization from time to time than keep
everyone terribly busy writing business on which we are going to
lose money.

Let that sync in, Buffett was willing to pay a staff of insurance personnel to do nothing all year if the business they would have been writing would not compensate them for the risks they were taking. Like most risk-based markets, Buffett knew that the insurance industry was cyclical and that the insurance businesses currently underwriting poor business and driving down margins for the rest of the market would go bust, the margins would then return to normal, and in some cases abnormal in the patient practitioner’s favor.

The Dao Of Capital

This idea of the roundabout investor was explicitly stated in Mark Spitznagel’s book The Dao of Capital. In it, he outlines the advantages of a roundabout strategy that can be found through history, from Coniferous trees to Laozi and Clausewitz. The idea here is that the most direct and obvious route to victory is seldom a route to victory at all. Laozi called it Shi vs. Li.

Simply stated, li goes for the immediate outcome of every battle, while shi seeks first the positional advantage of the setup.

Often the surest route to victory, surprisingly, is through indirect means and patience. This is similar to Buffett’s approach of letting the insurance business come to him when the time was right, rather than chasing future losses in a frenzy. Spitznagel would call this roundabout investing. When taking this approach it becomes imperative to understand the second and third-order effects of events, to capitalize on these indirect effects when the time comes.

The Indie Hackers Podcast

This leads me to the final set of material I’ve been consuming. I’ve been on a tear listening to every Indie Hacker’s Podcast I can get my hands on. I’m currently over 2/3rds of the way through all the podcast episodes and have learned an absurd amount from all of the entrepreneurs that have been on the podcast. However, the most topical to this post is the idea of what I’m calling the roundabout entrepreneur.

What has been most eye-opening to me about so many of these successful entrepreneurs is how long their businesses have been in operation in order to achieve the success they have. Prior to listening to the podcast, I was one of the sorry souls who thought you either had an overnight success viral mobile app or you had nothing, and since a few of my odd side projects hadn’t gone viral they weren’t worth pursuing further and were abandoned altogether.

Some of the entrepreneurs who’ve been on the podcast have made the off-hand comment similar to “yeah, we launched on product hunt and after the initial traction had to follow it up with content-marketing”. Courtland himself mentions a number of times that these one-off stunts usually don’t maintain growth and you typically can’t build a sustainable business around them.

To build a defensible sustainable business takes time, patience, determination, and discipline. If you are an overnight success, the chances are that you will not continue to be a success far into the future if you haven’t built the business chops to continue to operate correctly. Businesses take time (or capital) to grow. It’s as simple as that, and no amount of gimmicks or features is going to change that.

Once you accept that building a sustainable business takes time, and there isn’t anything you can do about that,* it becomes imperative to understand the second and third-order effects of events, to capitalize on these indirect effects when the time comes. Shi vs. Li. Because time is so important to the entrepreneurial process you have to be sure that what you’re working on has the ability to grow and be of worthwhile value far into the future and not just now. This is the idea of the roundabout entrepreneur.

*aside from diluting your equity, raising a round of funding, and throwing money at the business to speed the growth of course. However, if you haven’t steered the boat in a roundabout way, you may be steering it full steam ahead into a cliff.

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Startups – Rapid Growth and Innovation is in Our Very Nature!

This Trio of 30 Under 30 Founders Turned Early Rejections Into Hidden Blessings

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[Beyond Meat in Vegan News] Beyond Meat Giving Away Over 1 Million Burgers To Feed Healthcare Workers

Beyond Meat has announced that they will be giving away over 1 million Beyond Burgers to feed healthcare workers during the ongoing crisis as well as providing jobs to the workers of restaurants closed due to the pandemic.

Read more here.

The post [Beyond Meat in Vegan News] Beyond Meat Giving Away Over 1 Million Burgers To Feed Healthcare Workers appeared first on OurCrowd.

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Peer Support and Self Management Saturday’s – A Safe Place to Vent, Seek Emotional Support, Share Self Management Techniques and Experiences, or Just Rant

Welcome to this week’s Peer Support and Self Management Thread.

This is a Safe Place to Vent, Seek Emotional Support, Share Self Management Techniques and Experiences, or Just Rant.

The goal for this thread is to help one another manage mental and physical health so we can more easily find success.

We all struggle sometimes and it is important to recognize that the struggle is part of the journey. The important thing is to learn how to overcome that adversity to grow and succeed.

Be tactful and classy in how you vent your feelings and share your frustrations. Act in a mature manner.

Ask questions, share experiences, and be there for one another. Practice empathy in giving advice and remember that what worked for you isn’t guaranteed to work for others. Make suggestions, not demands of others.

#Because this is meant to be a safe place to support emotional and physical health there is a zero tolerance policy in effect. Be KIND. Be sure to report any conduct that is in violation of that key tenet.

You can also find more support using instant chat on the /r/startups discord.

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Startups – Rapid Growth and Innovation is in Our Very Nature!

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Treating Your Customers The Same Is Bad For Business; Do This Instead

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10 Life-Changing Books Every Side Hustler Needs to Read

As an entrepreneur, I’m a big advocate of using books to level up my game for one simple reason: a $ 20 business book is one of the least expensive crash-course educations you can get today. For the cost of a decent dinner, you can get a book that may change your life.

The following books were curated specifically because they’re great for anyone looking to start (and grow) a business on the side. This means you need to maximize your effectiveness and efficiency with the very limited free time at your disposal.

Now, pulled straight from my list of the best business books of all-time, here are my picks for the essential books you should read if you want to grow your side hustle into a full-time business.


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10 books to help grow your side hustle

1. Crushing It: How Great Entrepreneurs Build Their Business and Influence-and How You Can, Too by Gary Vaynerchuk

Four-time New York Times best-selling author, Gary Vaynerchuk, is back and on a mission with his brand new book, which already hit Amazon’s #1 best-seller list in social media before launching earlier this year.

In the book, Vaynerchuk offers up new lessons, strategies, tactics and advice that draws from both his own intensified business experience and that of many other entrepreneurs. Topics covered include how to build a powerful personal brand on all the major social networks, building a podcast presence and how to take advantage of other emerging platforms.

2. Deep Work: Rules for Focused Success in a Distracted World by Cal Newport

A Wall Street Journal best-seller, this book argues that one of the most valuable skills in the world is becoming increasingly rare: the ability to focus without distraction on a demanding task. Author Cal Newport explains that by mastering this skill, you’ll be able to more effectively process information and deliver better results in less time.

For that reason, this book will help you significantly with doubling down on growing your side hustle, by giving you focused rules to follow and not allowing yourself to get distracted by chasing the wrong opportunities or spending time in ways that don’t help you achieve your most meaningful goals. If you’re spreading yourself too thin and are ready to learn how to eliminate distractions, Deep Work is guaranteed to help you accomplish that.


Related: 15 Quotes That Will Motivate You to Start a Side Hustle

3. What If It Does Work Out? How a Side Hustle Can Change Your Life by Susie Moore

Author Susie Moore has written this book as a motivator for readers to get pumped up about pursuing the life they really want to live. We all have hobbies, talents and skills which we enjoy, but usually don’t go as far as turning them into a money-making ventures.

In her episode on my podcast, a key point she made about this book is that it’s so easy to think about all the possibilities and then shut yourself down with the question, “What if it doesn’t work out?” Moore asks us to instead consider, “What if it does work out?” Moore wrote this book to motivate you to overcome your fear of failure and doubts about whether or not pursuing your side hustle is the right decision, and gives actionable steps to begin building a profitable side hustle.

4. Tribe of Mentors: Short Life Advice from the Best in the World by Tim Ferriss

This new book from renowned business author, Tim Ferriss, comes as the culmination of everything he’s worked on over the past decade. From writing some of the most popular life advice books of all time, to launching Apple’s consistently number one-ranked business podcast, Tim has always been a mentor from afar for me.

Tribe of Mentors takes a different approach than most of the books on this list, as this one tackles a wide-range of topics and pulls insights and advice instead from people who’ve been influential mentors to Tim, from the likes of Ray Dalio to Maria Sharapova, Kelly Slater, Tony Hawk, James Altucher, Noah Kagan and others.

5. Side Hustle: From Idea to Income in 27 Days by Chris Guillebeau

“Side Hustle” comes as the fifth wildly successful book for the bestselling author of the seminal “$ 100 Startup,” Chris Guillebeau. Over the past couple of years, Guillebeau has been researching, connecting with and compiling side hustle stories from hundreds of entrepreneurs who’ve built impressive companies around their day jobs—and this book shares all of the most impactful lessons he’s learned.

Following a step-by-step plan of action, this book is perfect for those just beginning their side hustle journey today. In it, you’ll learn everything from how to brainstorm the right ideas for your own unique interests, to actually getting started with building a product or selling a service, mastering the art of selling and accelerating your progress once you’ve laid a solid foundation for the business.

6. The Motivation Myth: How High Achievers Really Set Themselves Up to Win by Jeff Haden

Debut business author, Jeff Haden, has long been Inc. Magazine’s most popular columnist, and a veteran ghostwriter of dozens of books for high-ranking executives over the years. In this highly counterintuitive (but practical) guide to finding and maintaining real lasting motivation, Haden explains how motivation as we know it is a complete myth.

Haden argues that motivation isn’t a magical formula that we need at the outset of any major change, challenge or endeavor. Rather, that motivation is a result of process, not a cause. If you’ve ever felt let down by self help books and “proven” success strategies, then this book is a must-read that’ll bring you practical advice to stop stalling and start actually working toward your dreams.

7. Extreme Ownership: How U.S. Navy SEALs Lead and Win by Jocko Willink and Leif Babin

Through their experiences with a SEAL unit in the battlefields of Iraq, authors Jocko Willink and Leif Babin learned firsthand that SEAL team leadership training is the best in the world, whether that’s in combat or in business. As an entrepreneur, developing your leadership skills is one of the most important factors in determining the success or failure of your venture—even while you’re running a one-person side hustle that still requires disciplined leadership.

This book takes the lessons these authors learned on the battlefield, and applies them to real-world business situations. Their belief is that the key to successful leadership is taking ownership for everything that happens in the business. There’s nobody else to blame; you take personal responsibility for your failures and reap the rewards when you succeed.

8. The Tipping Point: How Little Things Can Make a Big Difference by Malcolm Gladwell

This book from renowned author, Malcolm Gladwell, lays out his argument that there’s a magic point at which a business idea or movement crosses a threshold of adoption and begins to spread like wildfire. This could be an iPhone app that skyrockets to the top of the App Store charts in one weekend or a brand new shoe company that suddenly takes the world by storm. Why do things like this happen? They cross a tipping point.

Gladwell argues that there are particular personality types that deliberately work to push ideas to this tipping point, and it lays out how you can work to create your own tipping points—or surround yourself with people who are more naturally suited to help make that happen.


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9. Startup Opportunities: Know When to Quit Your Day Job by Brad Feld and Dr. Sean Wise

I’m a big believer in never quitting your full-time job to start a business without first validating your idea and having a sustainable income already coming from your business. Authors Sean Wise and Brad Feld elaborate on this conviction in this phenomenal book that teaches you how to validate your idea, then grow your revenue and continue building your business at a manageable pace.

The reality these entrepreneurs and authors have come to see, is that few businesses survive to make it five years, so it’s foolish to risk everything right at the beginning before you have definitive proof that customers are willing to pay for your solution. This book provides realistic advice on which businesses are likely to succeed and which aren’t.

10. The Power of Habit: Why We Do What We Do in Life and Business by Charles Duhigg

Bestselling author Charles Duhigg is a Pulitzer Prize-winning reporter that’s used this book to take us to the edge of scientific discoveries, explain why habits exist and how they can be proactively changed to create positive results in our lives. There’s a reason why it spent more than 60 weeks on the New York Times best-seller list—because its takeaways are incredibly practical and easy to implement toward creating habits to help grow your side hustle in the hours outside of your day job.

Duhigg emphasizes how important habits are to our success, and why they’re the essential keys to achieving meaningful goals. It’s our habits that give us the structure and discipline to exercise regularly, be more productive and continue making progress towards larger life goals. Without good habits, it’s all too easy to give up on your side hustle when the going gets rough.

If you want even more book recommendations to fuel your side hustle growth this year, check out my extensive list of the best business books I’ve ever read.

The post 10 Life-Changing Books Every Side Hustler Needs to Read appeared first on StartupNation.

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