Over a campfire this weekend, my fiance told me the story of Robert Smalls. If you’ve never heard his story, prepare to have your mind blown…
Robert Smalls was born a slave in South Carolina in 1839. When he died 75 years later, he owned the home where he was born. At one point, he even allowed his former master’s wife to move back in as his tenant.
Here’s an insanely short summary of the life of a larger-than-life American.
Robert Smalls outsmarts the Confederate Navy
When Robert Smalls was in his early 20’s, the Civil War had just broken out. He was assigned to work on a confederate ship, the USS Planter.
The Planter was stationed in Charleston, just a few miles south from a blockade of Union ships.
To slaves like Robert Smalls, Henry Louis Gates, Jr. wrote, the Union blockade wasn’t a threat but rather “a tantalizing promise of freedom.”
If Smalls could get to the Union ships, he knew he stood a chance at gaining his freedom.
One day in May 1862, Smalls decided that he would steal the Planter from the Confederate navy and head north to freedom or die trying.
An insanely dangerous gamble
Late one night, he shared his plan with some of the other slaves on board while the white crew slept ashore. Within just a few hours, they decided to make their escape.
Smalls put on the white captain’s straw hat, ordered the crew to hoist Confederate and South Carolina flags, and left port — a black captain with an all-black crew, steering a Confederate naval ship towards freedom.
Smalls played the part of a white naval captain brilliantly and tricked a series of Confederate checkpoints on their way North.
Smalls blows the ship’s whistle while passing Confederate Forts Johnson and, at 4:15 a.m., Fort Sumter, “as cooly as if General Ripley was on board.” Smalls not only knows all the right Navy signals to flash; he even folds his arms like Capt. Rylea, so that in the shadows of dawn, he passes convincingly for white.
The Union navy nearly kills Small and his crew
By sunrise, Smalls and his crew had nearly reached the Union blockade. Freedom was mere yards away when it struck him:
Oh, s***.I just sailed a Confederate ship directly into enemy territory. These Union ships are going to blow us to bits.
His wife, who he had snuck on board, came up with a brilliant plan…
She frantically scrubbed some sheets with soap until they took on a white-ish color and then hoisted the improvised surrender flags within seconds of the Union opening fire and possibly killing everybody on board.
From an eyewitness account that day:
Just as No. 3 port gun was being elevated, someone cried out, ‘I see something that looks like a white flag’…
When [the crew of the Planter] discovered that we would not fire on them, there was a rush of contrabands out on her deck, some dancing, some singing, whistling, jumping… [one of the] men stepped forward, and taking off his hat, shouted, ‘Good morning, sir! I’ve brought you some of the old United States guns, sir!’
From slave to naval officer to U.S. congressman
Not long after the surrender of the ship, the Union Navy paid Smalls and his crew half of its appraised value — around $40,000 in today’s dollars.
The naval officers who got to know Smalls described him as “superior to any who have come into our lines — intelligent as many of them have been.”
The Navy appointed him captain of the Planter, where he fought the Confederacy for years. Smalls even helped convince Lincoln’s Secretary of War Edwin Stanton to let black Americans fight for the Union.
Following the war, Smalls bought his old master’s home in South Carolina. He launched a series of business ventures, including a small railroad company and a local newspaper.
He then turned his energy towards politics, eventually becoming a state senator and a U.S. Congressman.
This quote from an 1895 speech Smalls gave summarizes the central theme in his life’s work:
My race needs no special defense, for the past history of them in this country proves them to be the equal of any people anywhere. All they need is an equal chance in the battle of life.
I’m embarrassed I didn’t know about Robert Smalls until today.
He is as pure an American hero as any other towering figure from U.S. history.
I can’t help but wonder, earnestly, where is his statue?
In 2017, I spent a few days traveling through Ecuador and the Galapagos Islands with Richard Dawkins.
If you don’t know Dawkins, he’s a famous writer, atheist, and evolutionary biologist.
He’s written more New York Times Bestsellers than most writers have written books.
He’ll be remembered as one of history’s most influential thinkers.
So you can imagine my surprise when one afternoon he passed around a manuscript of his next book and asked a few of us on the trip for feedback.
What on Earth could I tell Richard Dawkins about how his next book could be better?
The book was a beginner’s guide to atheism written for kids and young adults who were having doubts about the Bible and religion in general.
It was meant to be a sort of guide to help them articulate their doubts.
And after I read the first couple chapters, I realized something…
Yeah, these chapters are absolute fire, but what’s the point if the kid never brings it up to their parents? If they’re going to build confidence in their new beliefs, they need to ask adults questions and then see how bad their answers are.
The rest of the group chimed in with suggestions, but it was mostly just one form of praise or another.
Dawkins politely nodded along…
“You should add questions at the end of each chapter that a kid can ask their parents at the dinner table,” I told Dawkins.
He lit up.
“That’s a wonderful idea. Yes, I love that,” he said. He asked his girlfriend to write down the suggestion.
It was the only one he wrote down.
“Damn,” I thought to myself. “I guess I can pretty much always add value if I just try.”
Neither opportunity is “easy” (you have to put in work over a long period of time) and you’ll need to be pretty enthusiastic about your ideas, but the upside is huge.
Also, these opportunities basically did not exist for all of human history…until now. Lucky us.
1. One-person media companies
A one-person media company is exactly what it sounds like: it’s a profitable media company built around the ideas of a single person with at most one or two full-time employees, and often none at all.
This only became possible relatively recently.
Why Today Is Special
It’s now pretty much free to distribute media thanks to the internet
Smartphones, tablets, and e-readers (i.e. always-on and always-online media devices) are affordable and most people have one on them at all times
Because the internet and internet-connected devices have been widely adopted, it’s now possible to reach nearly any niche on Earth (lots of new audiences!)
Production software and hardware have become wildly affordable and accessible
The internet has created an opportunity to build a media company powered by the ideas of a single person, a payroll smaller than a convenience store, and revenues large enough that the company could trade on the NASDAQ.
It’s not easy to do. There’s a lot of competition. It can take a long time. But this is a post about possibilities, not probabilities.
Let’s have some fun and look at the upside potential of one-person media companies.
The podcast that could trade on the NASDAQ
In 2007, a relatively unknown Tim Ferriss published The 4-Hour Workweek.
The book sold well and, year after year, Ferriss continued to blog and publish books and amassed “a monthly audience in the millions or tens of millions.” (source)
In 2014, he was burned out from writing books and decided to launch a podcast as an experiment.
He was able to acquire an early enthusiastic following thanks to the audience he had spent years building, but it didn’t take long before the podcast reached far beyond his existing blog and book fans.
Today, The Tim Ferriss Show is one of the most popular podcasts on iTunes.
What you might not know is that The Tim Ferriss Show generates enough revenue from advertising that, were it to make a few structural and governance changes, it would be eligible to trade on the NASDAQ as a stand-alone company.
In the last three years alone, his podcast has generated nearly $17 million in revenue.
Here’s a detailed breakdown of The Tim Ferriss Show’s estimated revenue over the past few years:
Absolutely buck wild.
And it still costs next to nothing to produce the show…
It costs tens of thousands of dollars to get him to show up to your next event — a fee that he’s been able to increase in lockstep with his audience growth.
If there’s a formula here, it goes something like:
Use the internet to build an audience and momentum around your ideas
Roll that momentum into a book deal
Use your book to make money and build your credibility
Use your credibility to increase your speaking fees and help grow your audience even more
The one big drawback of the book/speaking and advertising models are that they typically need a big audience before they start working well.
There’s a third business model, though, that doesn’t require an army of enthusiastic fans and is filled with success stories…
3. Paid content and online courses
The internet is filled with people you’ve never heard of who are making a living, and in many cases a killing, sharing their expertise on a narrow, deep topic.
They’ll likely never make as much as a Tim Ferriss, but I mean who cares? There are some stunning success stories of no-name people striking gold within a niche.
Adam Wathan is one. He’s built a one-person media company around his programming tutorials, online classes, and e-books.
Check out his sales over the past 4 years (the 2nd tweet below):
He did not hire legions of full-time employees to help him hit $4 million in sales. He just kept pushing out educational videos and PDFs that he produced and distributed himself.
And, by the way, he’s no Steven Spielberg. Many of his videos are him just recording a screencast for 30 minutes as he debugs some obscure programming issue.
Another well-paid expert is Ben Thompson, whose paid newsletter Stratechery brings in over $2,500,000 each year from tech investors and entrepreneurs who pay for a subscription. (source)
The headcount for his multi-million-dollar-per-year business?
Himself and a personal assistant.
Here’s the rough playbook:
The internet gives you an unprecedented opportunity to turn your knowledge into information products that you can sell to nearly any company or person on Earth who needs it.
4. The swiss army knife approach
In reality, many one-person media companies use a combination of business models.
Despite shunning advertising, James Clear embeds affiliate links for any books he recommends. He also sells an online course about habits.
But therein lies the beauty of the one-person media company…
There are tons of creative ways to turn your ideas into money. You can use whichever ones make the most sense for your particular goal or situation.
2. Pour gasoline on your career
Maybe you don’t want to quit your job to start podcasting, blogging, or recording videos for 40 hours each week.
Thankfully, there’s a much more practical reason why some of us might want to start sharing our ideas online (and you can do it in your spare time):
Sharing your ideas online is one of the fastest ways to gain visibility as an expert or leader in your industry.
I’m not talking about crappy “thought leadership” content…
I’m talking about sharing good ideas that will earn you the respect of your peers and will make other people want to work with you.
Your public writing (or podcast or YouTube videos) are like a calling card for like-minded people to find you.
There are mountains of success stories here…
Holly Whitaker leveraged her blog to close a $10M round of funding for her sobriety school, Tempest.
Alexandria Ocasio-Cortez used Twitter to help go from bartender to the youngest woman ever elected to Congress.
Fred Wilson routinely points to his blog as paving the way for his success as New York City’s leading venture capitalist.
Nick Caldwell, an executive at Looker (recently bought for $2.6 billion), recently tweeted that not writing publicly sooner in his career was a mistake:
And while it typically takes a while to start gaining visibility online, I’ve seen plenty of exceptions… including a few up close.
When my friend Dan Li started writing a newsletter about venture capital in the pacific northwest last year, it only took a few months before other VCs and entrepreneurs began obsessively reading his work.
From the CEOs of local companies:
To other local entrepreneurs and investors:
He now has over 1,000 high-profile people in his industry waiting to hear from him each week.
You’ve already done the hard work to learn some important stuff. Why not invest some extra time to share it?
Your knowledge becomes exponentially more valuable when other people know you have it. Take it from this 19-year-old who just landed a dream internship after the CEO of Zoom saw one of his tweets:
Oh, and there’s one other thing: by forcing yourself to commit your ideas to paper, you’ll inevitably learn much quicker than your peers who don’t.
It’s a beautiful one-two punch: you become more knowledgeable and you become known as somebody with that knowledge to the people you want to connect with most.
Forget a big audience. You can pour gasoline on your career by building a small, targeted following made up of people who can help catapult you ahead.
Less lucrative (but still valid) reasons to share your ideas online
There are two less lucrative, but still-very-valid reasons to share your ideas online.
Both are worth a quick honorable mention.
3. Sharing your ideas online makes you accountabletocreate
I launched Stew’s Letter primarily as a way to keep myself accountable to write more in general.
I needed a creative outlet and this blog has been a wonderful way of keeping myself accountable to produce something every week.
There is something about having an audience at the other end of this that keeps me more productive than other creative outlets where I’m only accountable to myself.
Publicly commit to share your ideas, start building a small audience, and you’ll produce more than you could have ever imagined.
4. Sharing your ideas online helps you stay in touch with interesting people
Another big benefit of sharing your ideas online is that you get to keep in touch with interesting people at scale.
Every weekend, I sit down, huff and puff and write blog posts about god knows what, and then send my thoughts directly to people that I like and want to stay in touch with.
Some of them inevitably hit reply.
These aren’t people I plan to work with immediately, they’re just interesting people who I would normally run the risk of falling out of touch with.
Maybe there are more efficient ways of keeping in touch with people, but I haven’t found one better than sending out an email to all of them at once every single week.
So… now what?
If you like sharing your ideas, you picked an unbelievable time to be alive.
If you’re willing to put them online, you’ll have access to enormous opportunities.
From building a profitable, low-overhead media company to getting ahead in your career by attracting the people who can help you most… the upside is just silly.
The costs are mostly just your time.
So… open up Twitter, Medium, WordPress, iMovie, TikTok, or whatever, and get to work.
In the mid-1980’s, Richard Hamming, a retired Bells Lab scientist, delivered his famous “You and Your Research” lecture, which summarized his 40-year-long career and attempted to answer the question:
“Why do so few scientists make significant contributions and so many are forgotten in the long run?”
The entire talk is packed with wisdom, but one idea in particular has always stuck with me:
I notice that if you have the door to your office closed, you get more work done today and tomorrow, and you are more productive than most.
But 10 years later somehow you don’t know quite know what problems are worth working on; all the hard work you do is sort of tangential in importance.
He who works with the door open gets all kinds of interruptions, but he also occasionally gets clues as to what the world is and what might be important.
Now I cannot prove the cause and effect sequence because you might say, “The closed door is symbolic of a closed mind.” I don’t know. But I can say there is a pretty good correlation between those who work with the doors open and those who ultimately do important things, although people who work with doors closed often work harder.
Somehow they seem to work on slightly the wrong thing – not much, but enough that they miss fame.
As somebody who cherishes their heads down time, this was a reminder to occasionally get out of my own head and allow for more serendipity and “interruptions.”
Here are two big ideas I’ve revisited since being under quarantine.
The World Is A Malleable Place
Many of us are way too cynical.
We think that the world is the way it is and there just ain’t that much we can do about it.
But in my more lucid moments I’ve heeded this wisdom from Silicon Valley legend Marc Andreessen:
The world is a very malleable place. If you know what you want, and you go for it with maximum energy and drive and passion, the world will often reconfigure itself around you much more quickly and easily than you would think.
And this from entrepreneur and former Y Combinator president Sam Altman:
A big secret is that you can bend the world to your will a surprising percentage of the time—most people don’t even try, and just accept that things are the way that they are.
People have an enormous capacity to make things happen. A combination of self-doubt, giving up too early, and not pushing hard enough prevents most people from ever reaching anywhere near their potential.
We Accept Crappy Circumstances Out Of Pride And Fear
I picked up my old copy of the kind-of-scammy-but-totally-brilliant The 4-Hour Workweek last night and immediately got hit with this truth-seeking missile:
Don’t confuse the complex with the difficult. Most situations are simple — many are just emotionally difficult to act upon.
The chapter was mostly about how our fragile, prideful egos invent clever rationalizations to justify our previous bad decisions.
And whenever we ignore what is true and obvious, we deny ourselves a chance to actually improve our situation.
Just because you are embarrassed to admit that you’re still living the consequences of bad decisions made 5, 10, or 20 years ago shouldn’t stop you from making good decisions now.
If you let pride stop you, you will hate life 5, 10, or 20 years from now for the same reasons.
The passage ends on a zinger quote from British author Colin Wilson:
The average man is a conformist, accepting miseries and disasters with the stoicism of a cow standing in the rain.
Stay juiced and see you on the other side.
When the COVID-19 lockdown ends and you’re legally permitted outdoors again, may you burn bright with the fire of somebody ready to change the world or, at least, themselves.
I am not proud of how many opinions I have about bumper stickers. It’s embarrassing, really.
But may I share one more?
“Coexist” bumper stickers are unbelievably stupid.
And, in my kind-of-obnoxious opinion, it’s obvious why…
Each religion makes truth claims about the nature of the universe. Those claims are the foundation of the religion. And the difference between those claims is what defines the boundaries of each religion.
In particular, religions make truth claims about the important stuff:
What the nature of reality is
How humans should behave
So when billions of people split into groups that have different belief systems for how we should live and what the nature of reality is… doesn’t conflict seem inevitable?
It sounds nice to say “coexist,” but isn’t that a pretty unlikely outcome in a system like that?
Why not just put a picture of a lighter next to a can of gasoline with the subtitle “Don’t Ignite”?
Thankfully, many religious folks are good people and respect their neighbors with different beliefs. They don’t take the divisive language and war-mongering in their scriptures too seriously.
But that doesn’t mean it’s not there. It means that they can exercise their best judgment and choose to ignore the dangerous parts of their chosen holy texts. I.e. they can become less religious for everybody’s safety.
I want mankind to live in peace and find a way to cooperate at scale, but if we do so it will be in spite of our obviously-in-conflict religious beliefs.
Instead of making an empty and mindless request for us to all “coexist,” maybe we should continue to put unrelenting critical pressure on our most troubling and divisive beliefs, wherever they may come from.
If you believe “God is energy” or “we all believe in a god, but maybe just have different names” or “I think we’re all after the same thing,” it may be too late to save you.
Consider for a moment that your use of language may be so fuzzy as for nothing to mean anything.
When entrepreneurs don’t know how to get from A to B, they take the smallest step in that direction that is available to them and then see if they can figure out the next one from the new starting point.
“I want to write a New York Times bestseller,” might make you feel impossibly far behind. But opening up a new Google Doc is pretty easy.
And War And Peace, like every bestseller before it, was written One. Word. At. A. Time.
Similarly, if you want to start a company that will revolutionize the food industry but you’re spinning your wheels trying to figure out the “perfect” strategy, maybe you could start small instead:
Why this matters for generalists
Generalists take a cross-disciplinary and unique approach to taking advantage of opportunities.
In the absence of a playbook to copy, the next move can often seem unclear.
We can fight this resistance by thinking like an entrepreneur and taking the smallest possible next step toward our goal.
Question for us
What’s something that’d take us 10 minutes to do today but get us one step closer to something we care about?
Thank you to Chris Sheffield for feedback on an early draft of this. And thank you to Loserthink for the inspiration for this mental model.