I really like startups and entrepreneurship. My obsession began once 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 companion 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 world 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 throughout the international monetary disaster, I’d as nicely construct a backup. I by no means did get laid off, so I burned the midnight oil after hours.
That is once I began writing about FIRE and my plan to flee, which I lastly did in 2012. Immediately the FIRE motion has grown worldwide, although as a founder I by no means totally capitalized on it.
I selected the bootstrapped way of life enterprise over the VC-backed route as a result of I now not had the required motivation to hunt most development and earnings. Leaping again into the fireplace 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 dangerous. I primarily needed to write down about life, so I did.
Dwelling in San Francisco since 2001, you may’t assist however catch the startup bug. I lived by means of the dot-com bust, the Fb and Google IPO period that minted 1000’s of recent millionaires and drove up actual property costs, 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 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 personal firms, is an LP in a number of enterprise funds, and has operated a non-public firm since 2009, I really like this convention. It’s best to go to the following one.
I often do not sit in on multiple presentation a day, preferring to talk with folks individually. However the lineup was so robust and the knowledge so compelling that I ended up attending 5 shows 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 need to be within the San Francisco Bay Space. The vitality 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 may meet. There isn’t a changing in-person relationship constructing. For those who’re not the place the motion is, your probabilities of breaking by means of are vanishingly small.
Second, I’m now firmly an “AI maximalist,” and it is best to think about turning into the identical. An AI maximalist believes AI will fully change the world. Though I have been investing in personal AI firms since early 2023, after realizing my editor father of 15+ years turned expendable after ChatGPT launched, I hadn’t been totally positive whether or not I used to be simply dwelling in a bubble. That is regardless of tons of of readers of FS giving me their views through the years.
Nevertheless, after attending Startup Grind, I am satisfied: the remainder of the nation is just not focusing almost sufficient on AI. Consequently, I am undecided 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 individuals are in all places. Excessive intelligence is commonplace amongst startup founders. However since AI is now probably the most clever device out there, what issues extra is investing in founders with the grit to get issues completed.
Those that refuse to take no for a solution, who take up suggestions and hold iterating, take advantage of progress. You’ll be able to by no means really fail when you by no means stop. Be keen to pivot or begin over when you hit a roadblock.
2. You must be the place the motion is.
Saving cash by dwelling in a low-cost metropolis is ok, however you may solely save a lot. You will need to concentrate on development, and development occurs the place firms, human capital, and monetary capital are already concentrated. It’s the identical idea of aggressively investing in development shares over dividend shares once you’re not but FIRE.
For instance, Gabe, the co-founder of Harvey AI, a authorized AI firm I am invested in by means of 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 condo 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. Nevertheless, you dramatically improve your luck by being the place all of the motion is.
3. The primary three to 5 seconds are every thing 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 probably misplaced them for good in response to 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 as a consequence 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 velocity of change. AI-native firms can construct quicker and pivot extra simply than legacy firms burdened with headcount and outdated techniques. Eoghan McCabe, CEO of Fin.AI, interviewed by Kleiner GP Ilya Fushman, held an identical view.
This has necessary implications for buyers. It is laborious to get enthusiastic about giant, publicly listed SaaS firms, regardless that valuations are extra compelling. It might take years for them to wash home, by which period AI-native firms may have lapped them. Please watch out for worth shares, as structurally, their terminal values have modified.
Sadly, it is laborious to get enthusiastic about any personal firm that is not AI-native. I’ve portfolio firms in a few enterprise funds which can be rising nicely, however I really feel zero enthusiasm for them. AI-native firms are merely rising far quicker, 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 workers. 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 “finest 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 development.
In case you are American and need to compete successfully, you want to be an American nerd with most grit. In any other case, you don’t have any probability. The neatest and hungriest folks from all over the world 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 firms was aggressive. On reflection, I ought to have put 60% into personal AI and the remainder into the S&P 500 and public firms as an alternative. I merely have not been bullish sufficient.
And to be honest, accessing personal AI firms is troublesome. You want to know somebody to get right into a spherical instantly or discover the proper enterprise fund with the fitting focus. Then when you commit capital, you may’t return and commit much more capital when you discover the GPs are investing in nice firms.
Fortunately, I invested in Fundrise’s enterprise product again in 2023, given I have been a companion of theirs since 2015. However like several funding that performs nicely, you at all times want you had put in additional. This is hoping they launch a brand new enterprise product sooner or later.
Immediately’s Founders Are Genuinely Inspiring
Seeing founders stuffed with vitality, keen to work seven days every week for 10-plus hours a day, is motivating. I labored 60-plus hours every week for 13 years and burned out.
Now I spend about 12 to fifteen hours every week on Monetary Samurai, which is a stroll within the park as compared. However I do know the correlation between laborious work and reward is actual. It is odd to listen to younger folks working solely 40 hours every week or much less complain that they can not get forward, when there are these sensible startup of us working 80 hours every week.
The entire addressable marketplace for AI is your entire U.S. labor drive, valued within the trillions. We do not know which firms will win, however the ecosystem will continue to grow, which is why actual property is a elementary manner play AI’s development.
I am an AI maximalist now, partly due to assembly the folks constructing the longer term. I plan to take a position extra aggressively going ahead, no less than for my youngsters’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 return?
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I am mailing signed copies of Millionaire Milestones to anybody who takes benefit of Empower’s free monetary check-up this yr. I’ve completed it 3 times over the previous decade and every session has sharpened my considering. Full particulars and directions are in this publish.
Monetary Samurai is a promoter of the Empower Advisory Group, LLC (“EAG”), and isn’t at present a consumer.
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