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The one thing I've learned from successful people

We’re all idiots.

Over the last 10 years I’ve done 800+ conversations with successful founders and read hundreds of books on the topic of “how to be successful.”

And after all that, there’s only one truth that I’ve learned: for any one piece of advice from a successful person, assume you can still win by doing the opposite.

Silicon Valley, as well as this little business bubble you and I are in, is famous for cute bits of advice. Do things that don’t scale. Build what the customer wants. Culture eats strategy for breakfast.

And mind you, I’m not just talking about business. But all facets of life. Health, relationships, or whatever else you have a guru for.

That advice can be great and oftentimes will increase the odds of success. But know this: you can do the opposite and still be successful.

So, what are some other conflicting bits of advice from people I’ve interviewed?

Doing one thing vs. do many things

• ​Ryan Smith: "I didn't do anything else... I was literally like Qualtrics for 20 years. Heads down." Co-founded Qualtrics, which SAP bought for $8 billion in cash in 2018. Bought the Utah Jazz in 2020.
• ​Chris Koerner: "I think focus is overrated because compounding doesn't care." Says he makes about $3 million a year from six or seven side businesses.
• ​Tom Freston: "We're going to be a niche network, do one thing all the time, do it really well, build up a relationship with our viewers." Founded MTV. Was CEO of Viacom.
• ​John Morgan: "Those people that tell you to focus, they're also doing a lot of this. Hunting, fishing, golfing." Co-founded Morgan & Morgan, the largest U.S. personal-injury firm, which says it brings in $2.4 billion a year. This is him saying he doesn’t focus on one thing.
• ​Joe Lonsdale: "my partners are allowed to work on up to six things at once… I think if you're just operating, you want to do like one or two at most." Co-founded Palantir. Runs 8VC, which manages $13.4 billion.

Raise VC vs. never raise

• ​DHH: "We never raised VC... We always had to earn the money we wanted to spend first." Co-founded 37signals (Basecamp, HEY), which has been profitable every year for 25 years and makes "tens of millions" in annual profit.
• ​Brian Halligan: "I think you should raise a lot so you can kind of make it through." Co-founded HubSpot, which is worth about $11.7 billion.
• ​Wade Foster: "I think the word people call it now is seed strapped. So, we did go through YC and we raised about a million in change." Co-founded Zapier, which is worth $5 billion.

Grind vs. a 40-hour week

• ​Dharmesh Shah: "you can outthink me, I think that's relatively easy to do, you will not out grind me, you will not outwork me because that's under my control. And so I've always believed that the kind of quality of the outcomes is almost directly always directly proportional to a number of iterations." Co-founded HubSpot.
• ​Mark Pincus: "I say I'm not stressed enough. I miss the level of intensity." Founded Zynga, which Take-Two bought at a $12.7 billion enterprise value.
• ​Rob Dyrdek: "I work less now than I've ever worked... about a 40 hour week." Created Ridiculousness and founded Dyrdek Machine. Puts his net worth at $350 million.
• ​MrBeast: "I just go as hard as I can, every ounce of my entire body until I just crash." Runs YouTube's most-subscribed channel, with about 522 million subscribers.
• ​Lloyd Blankfein, asked if he'd put in the hours again: "of course, I will say yes, but not not not enough that would be reasonable to most people." CEO of Goldman Sachs for 12 years.
• ​Jack Smith: "So for me, balance is important and not having tunnel vision." Co-founded Vungle, which Blackstone bought for a reported $750 million.

Big goal vs. no goals

• ​Me: "I had a goal to make $20 million liquid by the age of 30."
• ​Jason Fried: "I've never believed in goals. I just kinda do the best I can and see where it goes." Co-founded 37signals, which makes tens of millions in profit every year.
• ​Graham Weaver: "And so I literally would write down my goals every single day, multiple times a day in in high school." Founded Alpine Investors, which says it manages $18.7 billion.
• ​Dharmesh Shah: "I tend not to have explicit goals." Co-founded HubSpot. Forbes puts his net worth at $1.1 billion.

Pick your own stocks vs. stop trading

• ​Barry Ritholtz: "Put the phone down. Stop trading." Co-founded Ritholtz Wealth Management, which manages about $9.4 billion, on why index funds are best.
• ​Lloyd Blankfein: "10% are in ETFs and 90% are in single stocks because that's what I like to do." Ran Goldman Sachs as CEO for 12 years on his love of day trading.

Work remote vs. get everyone in one building

• ​Wade Foster: "the sort of remote work story is one where we've just never had an office way before anyone thought that that was normal." Co-founded Zapier, which a 2021 secondary sale valued at $5 billion.
• ​Alex Hormozi: "But in like the business Olympics, the people who are serious about it, they're going to be together. They're going to be co-located." Runs Acquisition.com, which says its portfolio companies do over $250 million a year in revenue.

Never risk ruin vs. not afraid to lose it all

• ​Jason Fried: "I'll take risks, but I don't take risks that put me at risk." Co-founded 37signals, a bootstrapped business with tens of millions in annual profit.
• ​Rohan Oza: "I think you have to be willing to lose if you're going to win." Was the marketer behind Vitaminwater at Glacéau, which Coca-Cola bought for $4.1 billion.
• ​Syed Balkhi: "you have to be very conservative to not lose it all because I came from nothing. I don't want to go back to that." Founded Awesome Motive, a +$100 million bootstrapped startup.
• ​Guy Spier: "set myself up such that when I miss really, really badly, I'm still going to be okay." Founded Aquamarine Capital. In the billionaire range.
• ​Craig Fuller: "And so I'm not afraid of losing it all. And I know that I can get it back." Says his media company Firecrown will finish the year at a $60 million revenue run rate.

Money buys happiness vs. it doesn't

• ​Scott Galloway: "So all this bullshit that money doesn't buy you happiness, oh, my God, that is a myth." Founded L2, which Gartner bought for $155 million.
• ​Andrew Huberman: "I would say money can't buy happiness, but it absolutely can buffer stress." Teaches neurobiology at Stanford as a tenured professor. Huberman Lab says it has over 1 million email subscribers.

Move faster vs. win by outlasting

• ​Grant LaFontaine: "If you have time to even think about it, you're moving too slow." Co-founded Whatnot, which raised money at an $11.5 billion valuation in 2025.
• ​Laird Hamilton: "mine is a patient thing. Like I my favorite term is "victory through attrition." Co-founded Laird Superfood, which raised about $62 million in its 2020 IPO.

Passion vs. talent

• ​Tony Hawk: "I never considered quitting skating cuz I never started skating for money."
• ​Scott Galloway: "Don't find your passion, find your talent and then commit to developing mastery." Founded L2, which Gartner bought for about $155 million.

Spend on ads vs. never spend $1

• ​Alex Lieberman: "my only regret is we couldn't figure out a way... to put more money into Facebook ads." Co-founded Morning Brew, which sold for hundreds of millions.
• ​Kevin Ryan: "Business Insider is at 300 million uniques today and never spent $1 in advertising." Founded Business Insider, which sold at a $442 million valuation.

The above are examples that I have on the record on My First Million. But there are so many more. Plus, the books that I’ve read.

If you like this series then next time I can show even more.

Speaking of advise, I'd be remise to not mention Hampton at this point. Its my company so I'm obligated to promote it. But the whole point of Hampton is to get good advice.

We're building Core groups in 18 cities. Particularly, Miami and Boston have Core groups that need a an additional member.

Obligatory plug done.

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Last week: 15,268 of you opened (out of 32,414). That’s a 47.1% open rate. 4.75% of you clicked (5,752 total). Most clicked: the YouTuber who explains fabric (492), the Hacker News thread on middle-aged men (433), and the 24,000 sq ft mega mansion (419). So, in summary: you people love fabric, existential dread and giant houses. Same.

[TBD: best reader replies to last week’s PS (the most expensive “productivity” purchase that really just bought you time), if you want to share them here]

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Cool stuff I’m consuming:

Cell phones are cigarettes (chart): In 1963 Americans smoked enough cigarettes for every adult to have more than half a pack a day, about 4,300 per person. Smoking climbed almost every year from 1900 to the peak in 1963, then fell to less than half of it by the early 2000s. What will cause the drop for cell phones and what year are we in?

Montana Knife Company (article): I'm hearing people talk about this knife company. They're 6 years old. Bootstrapped. Doing well over $100 million a year in revenue. Founder Josh Smith: "I registered the name Montana Knife Company when I was 19 years old, and I didn't launch it until I was 39."

What is the average net worth by age? (article): Average U.S. household net worth by age, from the Fed's new 2025 survey: under 35 is $136,000, 35 to 44 is $670,000, 45 to 54 is $1.24 million, 55 to 64 is $1.87 million, 65 to 74 is $1.87 million, and 75+ is $1.95 million.

"Let me not then die ingloriously and without a struggle, but let me first do some great thing that shall be told among men hereafter." (tweet). This gets me jacked up.

Is it finally time to expect lower stock returns? (chart): Annual S&P 500 returns: 3 years +22.9%, 10 years +15.3%, 15 years +15.7%, 30 years +10.3%, 50 years +11.9%. The longrun norm is !0% to 12% a year, so this is rare. The last time they ran this hot was the late 1990s, right before the dotcom crash.

"There's so much pressure to make money" (reel): Robert Greene, the guy who wrote The 48 Laws of Power, says most writers get a $20,000 to $50,000 advance and have to finish the book in a year just to pay rent. Life got too expensive for artists to take their time, and he thinks the work is suffering for it.

The psychology of where you live (reel): Five rules for being happy where you live: Your 10-minute radius matters more than your city. A bigger house can mean a smaller life, because you just go house to car to work and back. Moving won't change who you are, but it changes what feels normal. And where your friends live should decide where you live more than we admit.

Gales of November (book): Read this last week. 9/10. The Great Lakes, during the 1950-70s, controlled American commerce. Enough iron ore to make 50 million cars a year went through the Great Lakes. In the '70s, the most famous ship sank. this is the story of the history of commerce in the Great Lakes, as well as the sinking. I realize my description doesn't make it sound interesting, but holy hell, this was a page-turner

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I want to be someone that you admire

I want the record to show that I’m a cool dad. This past weekend we had a 1 and 3 year birthday for my kids.

I fetched the cake and balloons from a store down the street with my skateboard. My mother was visiting from St. Louis and took this video of me arriving home skating and carrying balloons.

In my 20’s I became obsessed with the idea that I should put the work in today that will make my future self proud. That idea motivated me to be successful.

But now that I have a family, I often think to myself: what can I do today that will make my future family proud.

It can be small dumb stuff like taking a photo to remind them when they’re older that I was silly and skated on their birthday.

But all of this has made me think a lot about admiration and how that’s a wonderful quality to look for in people you do life with.

I admire my wife. That’s how I knew I wanted to marry her. She was/is formidable. Very capable. On our 3rd date I got a kidney stone while we were out and she rushed me to the hospital and took care of business.

My co-founder Joe is like that, too. I admire him. On certain topics, not only do I trust him but I feel bad for the person he’s going against because I know he’ll win.

I want people to feel admiration for me like I do the people I admire. On certain topics, I want them to think to themselves: “this guy’s a f*cking animal!”

Ted talk over.

I love you,

Sam

PS: Last night I met a founder at a Hampton event who does $20m a year for his app with 5 employees. What a world. Reply back with some crazy "I met a guy who..." business stories and I'll mention 'em in next week's email.