I really 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 yr earlier than graduating from William & Mary, I used to be supplied an opportunity to work at my father’s buddy’s eyeglass elements manufacturing unit in Shenzhen, China. The proposal was to be its supervisor and accomplice to broaden into the nation. China was lastly opening up, and I had seen the fast change firsthand as an change pupil in Beijing in 1997.
However I used to be nervous. I knew nothing concerning 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 through the world monetary disaster, I’d as effectively construct a backup. I by no means did get laid off, so I burned the midnight oil after hours.
That is after I began writing about FIRE and my plan to flee, which I lastly did in 2012. At present the FIRE motion has grown worldwide, although as a founder I by no means absolutely capitalized on it.
I selected the bootstrapped life-style enterprise 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 really FIRE makes you a foul 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 needed to write down about life, so I did.
Dwelling in San Francisco since 2001, you possibly can’t assist however catch the startup bug. I lived by the dot-com bust, the Fb and Google IPO period that minted hundreds of recent millionaires and drove up actual property costs, and now the AI wave creating fortunes another time.
Assembly Startup Founders Will Make You A Believer
Not too long ago, I attended the 2026 Startup Grind convention 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 really like this convention. You must go to the subsequent one.
I normally do not sit in on a couple of presentation a day, preferring to speak with folks individually. However the lineup was so robust 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 power is electrical and the connections are limitless. 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 will meet. There isn’t a changing in-person relationship constructing. In the event 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. An AI maximalist believes AI will fully change the world. Though I have been investing in non-public AI corporations since early 2023, after realizing my editor father of 15+ years grew to become expendable after ChatGPT launched, I hadn’t been solely positive whether or not I used to be simply residing in a bubble. That is regardless of a whole lot of readers of FS giving me their views over time.
Nonetheless, after attending Startup Grind, I am satisfied: the remainder of the nation is just not focusing practically sufficient on AI. Because of this, I am unsure they’re prepared for what’s coming.
Key Takeaways From The Startup Grind Convention
Let me broaden on the 2 factors above and share a number of extra.
1. Grit issues greater than intelligence.
Good and motivated persons are all over the place. Excessive intelligence is commonplace amongst startup founders. However since AI is now essentially the most clever software accessible, 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 hold iterating, take advantage of progress. You’ll be able to by no means really fail for those who by no means stop. Be prepared to pivot or begin over for those who hit a roadblock.
2. It’s a must to be the place the motion is.
Saving cash by residing in a low-cost metropolis is okay, however you possibly can solely save a lot. You will need to deal with progress, and progress occurs the place corporations, human capital, and monetary capital are already concentrated. It’s the identical idea of aggressively investing in progress shares over dividend shares whenever you’re not but FIRE.
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 does not assume 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 house 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 rising outsized wealth is because of luck. Nonetheless, you dramatically enhance your luck by being the place all of the motion is.
3. The primary three to 5 seconds are all the pieces 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 must 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 does not matter as a lot, stated Amjad, CEO of Replit. Company and real style are what stand out. Because it’s a lot simpler to construct now on account of AI, rent folks with an entrepreneurial spirit.
5. Construct AI-native or do not trouble.
Ashton Kutcher, actor and GP at Sound Ventures, was onstage with Warp CEO Ayush Sharma discussing the pace of change. AI-native corporations can construct sooner and pivot extra simply than legacy corporations burdened with headcount and outdated methods. Eoghan McCabe, CEO of Fin.AI, interviewed by Kleiner GP Ilya Fushman, held the same view.
This has necessary implications for buyers. It is onerous to get enthusiastic about giant, publicly listed SaaS corporations, regardless that valuations are extra compelling. It might take years for them to wash home, by which era AI-native corporations can have lapped them. Please watch out for worth shares, as structurally, their terminal values have modified.
Sadly, it is onerous 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 seen the overwhelming majority of attendees are foreigners and technically-oriented staff. The Startup Grind convention mirrored the identical, however they’re the founders.
These are the founders who naturally rent folks much like themselves, and if these are the “greatest and brightest,” it is no surprise prime universities constantly 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.
In case you are American and wish to compete successfully, it is advisable to be an American nerd with most grit. In any other case, you don’t have any probability. The neatest and hungriest folks from world wide are coming to the SF Bay Space to construct.
7. Most individuals have not invested sufficient in AI.
I assumed allocating as much as 20% of my investable capital to non-public AI corporations was aggressive. Looking back, I ought to have put 60% into non-public AI and the remainder into the S&P 500 and public corporations as a substitute. I merely have not been bullish sufficient.
And to be honest, accessing non-public AI corporations is tough. You might want to know somebody to get right into a spherical straight or discover the proper enterprise fund with the appropriate focus. Then when you commit capital, you possibly can’t return and commit much more capital for those who discover the GPs are investing in nice corporations.
Fortunately, I invested in Fundrise’s enterprise product again in 2023, given I have been a accomplice of theirs since 2015. However like several funding that performs effectively, you all the time want you had put in additional. Here is hoping they launch a brand new enterprise product sooner or later.
At present’s Founders Are Genuinely Inspiring
Seeing founders filled with power, prepared 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 onerous work and reward is actual. It is odd to listen to younger folks working solely 40 hours per week or much less complain that they cannot get forward, when there are these sensible startup people working 80 hours per week.
The full addressable marketplace for AI is all the 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 actual property is a basic manner play AI’s progress.
I am an AI maximalist now, partly due to assembly the folks constructing the longer term. I plan to speculate extra aggressively going ahead, at the very least 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 assume the SF Bay Space resides in an AI bubble? Or do you assume the remainder of the world resides in an AI bubble, not prepared for what’s about to come back?
Get a Free Monetary Evaluation From Empower
Constructing or investing in startups means nothing if your individual funds aren’t so as. Use Empower, the online’s #1 free monetary app, to trace your money circulate, x-ray your portfolio for extreme charges and hidden danger, and plan for the longer term with their retirement calculator. The extra readability you may have in your funds, the higher positioned you will be to make the most of 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 yr. I’ve executed it thrice over the previous decade and every session has sharpened my pondering. Full particulars and directions are in this submit.
Monetary Samurai is a promoter of the Empower Advisory Group, LLC (“EAG”), and isn’t at present a consumer.
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