Most of us take the safe route. We go to college, get a job, and spend the next 30 years hoping our employer doesn’t one day decide we’re suddenly redundant. I know this road well because I walked it for 13 years before I finally worked up the nerve to do my own thing in 2009.
My guest on the Financial Samurai podcast, Sunday’s War, didn’t wait as long as I did. He left at 27. And his story has a twist that most people don’t see coming. The biggest payday of his life also turned out to be the most miserable period of his career.
In this episode, I sit down with my school friend and father Domingo to talk about his journey from growing up in Monterrey, Mexico, to studying engineering at the University of Texas, to co-founding mobile security company Appthority, to selling it to Symantec. Then something else happened.
Today he runs a seed fund that supports founders building security for the AI age. You can listen here by clicking the embedded player or by listening Apple OR Spotify.
The Entrepreneur’s Journey
I want to start interviewing more entrepreneurs because HE has quietly given us all the ability to become one. Tools that once required a team and a budget now cost $20 a month and a free weekend.
This is the good news. The bad news is that the same technology is eliminating jobs left and right. For many students and working adults, taking a shot at entrepreneurship is becoming one of the few realistic options.
The other way out of “in permanent class” is to invest in companies that make our skills obsolete. If you can’t beat them, at least own a piece of them. It’s a grim trade, especially for anyone who hasn’t yet achieved financial independence, but ignoring it doesn’t make it any less true.
The problem is that most people have no idea where to start. So by walking through how different entrepreneurs actually built their own paths, I hope to give you and the students a clearer understanding of how to start being your own creators.
Growing up in Mexico with the mindset of a landlord
Domingo grew up in Monterrey, a city known for its industrial roots and entrepreneurial culture.
Many origin stories of California founders begin in a Berkeley dorm or a Palo Alto garage. Domingo started long before he ever set foot in California. He grew up in a place where starting a business was not a whimsical fantasy. It was just a normal thing that people did.
That mindset followed him to the University of Texas at Austin, where he studied engineering, and into a career in technology. Like most founders, his path was not a straight line. It is rare.
Building Appthority on the Mobile Wave
Appthority was born just as smartphones were taking over the workplace. Suddenly every employee was walking into the office carrying a powerful computer in their pocket, loaded with applications that no one in IT had vetted. This created a new security problem, and Domingo built a company to solve it.
From the outside, startups look clean. Founder discovers a problem, builds a product, raises money, gets rich.
The reality is years of uncertainty, recruiting, fundraising, spinning and praying. Most startups never reach profitability, let alone an acquisition. What stood out to me was that Domingo and his co-founders were willing to keep going until the money ran out.
Sitting with that kind of uncertainty is harder than it sounds, which is why I’ve never done it this way. I preferred to hold down a full-time job and build Financial Samurai on the side, and only took the plunge when there was real traction. That jump came two years and eight months after I started, not on day one. Domingo bet first and asked for proof later. I wanted proof before I bet. Both can work, but it helps to know what kind of person you are before you jump in.
Exciting output
In 2018, Symantec acquired Appthority.
For a founder, an acquisition is validation. Years of sacrifice, late nights and tough decisions finally get a stamp that says it was worth it. It’s the moment aspiring entrepreneurs fixate on. Notification, dinners, bank transfers.
And then real life goes on.
Plot Twist
This is where Domingo’s story stops sounding like a press release.
In 2019, Broadcom bought Symantec’s enterprise security business for about $10.7 billion. Appthority went along for the ride. So Domingo, who had already sold his company once, suddenly found himself inside a massive corporation as part of a second acquisition.
On paper, this was the pinnacle. He was making more money than he had ever made in his life.
And he was miserable.
I’ll let him explain that part himself in the episode, because it’s the most shocking part of the conversation. Golden handcuffs are still handcuffs. They just fade a little nicer.
I have long argued that there is the joy of being your own bossand Domingo’s reactions support my belief. What he did next is the part that I find the most instructive, and this is where the episode goes from a starter story to something more useful for the rest of us.
My biggest takeaway
The lesson from Domingo is not “go start a company.” It’s more subtle than that.
There is no single correct path to financial success. Some people build venture-backed rockets. Some build lifestyle businesses. Some climb the corporate ladder. Others simply invest continuously for decades and quietly earn.
What matters is choosing the path that fits the life you want, not what looks best on LinkedIn. Know yourself.
For me, freedom won earning maximum incomethat’s why I left in 2012 at the age of 34. For Domingo, construction was able to stay comfortable, even when staying comfortable pays the most. We both bet with ourselves. We both gave up something safe to get something better.
The safe route feels safe until the employer reminds you that you were always optional. Betting on yourself is terrifying until it becomes the clearest decision you’ve ever made.
Listen to the full Episode
If you’ve ever wondered what it takes to build a venture-backed company, raise capital, sell it, survive the corporate machine that buys you out, and then have the courage to walk away and start over, this talk is for you.
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