I like startups and entrepreneurship. My obsession began after I was reselling Nerds sweet in Taipei, bought from the U.S. commissary retailer. To acknowledge and exploit a pricing arbitrage as a nine-year-old felt like profitable the lottery each time a brand new batch arrived.
In 1998, a 12 months earlier than graduating from William & Mary, I used to be provided an opportunity to work at my father’s good friend’s eyeglass components manufacturing facility in Shenzhen, China. The proposal was to be its supervisor and companion to increase into the nation. China was lastly opening up, and I had seen the fast change firsthand as an change scholar in Beijing in 1997.
However I used to be nervous. I knew nothing in regards to the enterprise. As a substitute of taking the journey of a lifetime, I took the positive factor: a global equities job at Goldman Sachs in New York Metropolis. Ever since, I’ve carried a mixture of curiosity and delicate remorse. How would my life have turned out had I jumped on that entrepreneurial path in 1999?
Launched My Personal Startup In 2009
In 2009, I made a decision to cease stalling and begin Monetary Samurai. I figured if I used to be going to get laid off in the course of the global financial crisis, I’d as effectively construct a backup. I by no means did get laid off, so I paid some man $500 off Craigslist to get it up and working.
That is after I began writing about FIRE and my plan to flee, which I lastly did in 2012. At present the FIRE movement has grown worldwide, although as a founder I by no means totally capitalized on it.
I selected the bootstrapped lifestyle business over the VC-backed route as a result of I not had the required motivation to hunt most progress and earnings. Leaping again into the hearth and grinding for 12 to fifteen hours a day was not interesting.
Being actually FIRE makes you a bad entrepreneur. You left your job since you weren’t financially motivated, and that does not change. Turning Monetary Samurai right into a NerdWallet and aggressively pushing high-interest bank cards to maximise earnings felt unhealthy. I primarily wished to write down about life, so I did.
Residing in San Francisco since 2001, you’ll be able to’t assist however catch the startup bug. I lived by the dot-com bust, the Fb and Google IPO period that minted hundreds of latest millionaires and drove up real estate prices, and now the AI wave creating fortunes yet again.
Assembly Startup Founders Will Make You A Believer
Not too long ago, I attended the 2026 Startup Grind conference on the Fox Theatre in Redwood Metropolis. A golf buddy, James Gee, whom I met at a month-to-month Orrick/Vouch golf tech outing, was one of many organizers. James is Irish, can hit 320-yard bombs, and fell in love with startups, so we made a pure connection.
As somebody who invests in non-public corporations, is an LP in a number of enterprise funds, and has operated a non-public firm since 2009, I like this convention. You must go to the subsequent one.
I often do not sit in on multiple presentation a day, preferring to speak with individuals individually. However the lineup was so sturdy and the knowledge so compelling that I ended up attending 5 displays over two days. I additionally did not inform anybody I used to be going, wanting the liberty to maneuver at my very own tempo after dropping off the kiddos at college.
Two main takeaways stood out.
First, in case you are a builder or enterprise capitalist, you must be within the San Francisco Bay Space. The vitality is electrical and the connections are countless. From ready in line for an acai bowl to taking part in poker at a random networking occasion, you by no means know who you may meet. There isn’t a changing in-person relationship constructing. In case you’re not the place the motion is, your probabilities of breaking by are vanishingly small.
Second, I’m now firmly an “AI maximalist,” and it’s best to think about changing into the identical. Though I have been investing in private AI companies since early 2023, after realizing my editor father of 15+ years grew to become expendable after ChatGPT launched, I hadn’t been completely positive whether or not I used to be simply residing in a bubble. That is regardless of a whole bunch of readers of FS giving me their views through the years.
Nevertheless, after attending Startup Grind, I am satisfied: the remainder of the nation will not be focusing almost sufficient on AI. Because of this, I am undecided they’re prepared for what’s coming.
Key Takeaways From The Startup Grind Convention
Let me increase on the 2 factors above and share a number of extra.
1. Grit issues greater than intelligence.
Good and motivated individuals are in all places. Excessive intelligence is customary amongst startup founders. However since AI is now essentially the most clever instrument out there, what issues extra is investing in founders with the grit to get issues executed.
Those that refuse to take no for a solution, who take in suggestions and maintain iterating, take advantage of progress. You’ll be able to never truly fail if you never quit. Be keen to pivot or begin over for those who hit a roadblock.
2. You need to be the place the motion is.
Saving cash by residing in a low-cost metropolis is ok, however you’ll be able to solely save a lot. You need to give attention to progress, and progress occurs the place corporations, human capital, and monetary capital are already concentrated.
For instance, Gabe, the co-founder of Harvey AI, a authorized AI firm I am invested in by a fund, relocated from LA to San Francisco as a result of they wanted to be within the AI combine. With out that transfer, he would not suppose he would have grown the corporate to its present $11 billion valuation. Gabe talked about he nonetheless sleeps on the mattress on the ground of his condominium with no mattress body as a result of there wasn’t the correct insurance coverage when the movers got here.
A lot about constructing a profitable firm and growing outsized wealth is due to luck. Nevertheless, you dramatically enhance your luck by being the place all of the motion is.
3. The primary three to 5 seconds are all the things for capturing consideration.
Consideration spans are shrinking. Whether or not it is video or writing, if you cannot hook the viewer or reader within the first three to 5 seconds, you have doubtless misplaced them for good based on James Dumoulin. That is one thing I have to work as I have a tendency towards long-form content material with a lot deeper evaluation.
4. Rent for company and style, not pedigree.
Their background would not matter as a lot, mentioned Amjad, CEO of Replit. Company and real style are what stand out. Because it’s a lot simpler to construct now as a result of AI, rent individuals with an entrepreneurial spirit.
5. Construct AI-native or do not hassle.
Ashton Kutcher, actor and GP at Sound Ventures, was onstage with Warp CEO Ayush Sharma discussing the velocity of change. AI-native corporations can construct sooner and pivot extra simply than legacy corporations burdened with headcount and outdated programs. Eoghan McCabe, CEO of Fin.AI, interviewed by Kleiner GP Ilya Fushman, held an identical view.
This has vital implications for buyers. It is laborious to get enthusiastic about giant, publicly listed SaaS corporations, although valuations are extra compelling. It may take years for them to scrub home, by which era AI-native corporations could have lapped them. Please beware of value stocks, as structurally, their terminal values have modified.
Sadly, it is laborious to get enthusiastic about any non-public firm that is not AI-native. I’ve portfolio corporations in a few enterprise funds which can be rising effectively, however I really feel zero enthusiasm for them. AI-native corporations are merely rising far sooner, and I believe different buyers really feel the identical. The bar has modified.
6. Worldwide builders are driving the AI wave.
At poker and networking occasions in San Francisco, I’ve observed the overwhelming majority of attendees are foreigners and technically-oriented workers. The Startup Grind convention mirrored the identical, however they’re the founders.
These are the founders who naturally rent individuals much like themselves, and if these are the “finest and brightest,” it is no marvel high universities persistently admit a big share of worldwide college students: roughly 38% at Columbia, 24% at Stanford, and 18% at Berkeley. We should settle for this pattern.
If you’re American and need to compete successfully, it’s essential to be an American nerd with most grit. In any other case, you don’t have any likelihood. The neatest and hungriest individuals from world wide are coming to the SF Bay Space to construct.
7. Most individuals have not invested sufficient in AI.
I believed allocating as much as 20% of my investable capital to non-public AI corporations was aggressive. On reflection, I ought to have put 60% into non-public AI and 40% into the S&P 500 and public corporations as a substitute. I merely have not been bullish sufficient. Once more, this goes again to how FIRE dampens the revenue motivation.
And to be truthful, accessing non-public AI corporations is tough. That you must know somebody to get right into a spherical or discover the right venture fund with the best focus. Then when you commit capital, you’ll be able to’t return and commit much more capital for those who discover the GPs are investing in nice corporations.
I acknowledged and invested in Fundrise’s venture product again in 2023, given I have been a companion of theirs since 2015. However like several funding that performs effectively, you all the time want you had put in additional.
At present’s Founders Are Genuinely Inspiring
Seeing founders stuffed with vitality, keen to work seven days per week for 10-plus hours a day, is motivating. I labored 60-plus hours per week for 13 years and burned out.
Now I spend about 12 to fifteen hours per week on Monetary Samurai, which is a stroll within the park compared. However I do know the correlation between laborious work and reward is actual. It is odd to listen to younger individuals working only 40 hours a week or less complain that they cannot get forward, when there are these good startup of us working 80 hours per week.
The whole addressable marketplace for AI is your entire U.S. labor pressure, valued within the trillions. We do not know which corporations will win, however the ecosystem will continue to grow, which is why real estate is a fundamental way play AI’s growth.
I am an AI maximalist now, partially due to assembly the individuals constructing the long run. I plan to take a position extra aggressively going ahead, no less than for my kids’s sake. As a result of if I do not make investments for them, no one will.
Readers, anyone else an AI maximalist? Do you suppose the SF Bay Space resides in an AI bubble? Or do you suppose the remainder of the world resides in an AI bubble, not prepared for what’s about to return?
Get a Free Monetary Evaluation From Empower
Constructing or investing in startups means nothing if your personal funds aren’t so as. Use Empower, the online’s #1 free monetary app, to trace your money move, x-ray your portfolio for extreme charges and hidden threat, and plan for the long run with their retirement calculator. The extra readability you’ve gotten in your funds, the higher positioned you may be to benefit from the AI wave forward.
I am mailing signed copies of Millionaire Milestones to anybody who takes benefit of Empower’s free monetary check-up this 12 months. I’ve executed it thrice over the previous decade and every session has sharpened my pondering. Full particulars and directions are in this post.
Monetary Samurai is a promoter of the Empower Advisory Group, LLC (“EAG”), and isn’t at the moment a consumer.
In case you loved this publish, you’ll be able to join my free weekly newsletter. My objective is that will help you obtain monetary freedom sooner, relatively than later.
