Most of us take the safe road. We go to college, get a job, and spend the next 30 years hoping our employer doesn't suddenly decide we're out of a job. I know this path well because I walked it for 13 years before I finally got serious about doing my own things in 2009.
My guest on the Financial Samurai podcast, Domingo Guerra, I didn't wait nearly as long as I did. He left at the age of 27. And his story has a twist that most people don't see coming. The biggest payday of his life was also the biggest heartbreak of his career.
In this episode, I sit down with my friend and classmate Domingo to discuss his journey from growing up in Monterrey, Mexico, to studying engineering at the University of Texas, to co-founding the security company Appthority, to selling it to Symantec. Then something else happened.
Today he holds a seed stage fund that supports inventors building security for the AI era. You can listen here by clicking the embedded player or listen an apple or Spotify.
Entrepreneur's Journey
I want to start interviewing more entrepreneurs, because AI has quietly given us the ability to be one. Tools that used to require a team and a budget now cost $20 a month and a free weekend.
That's good news. The bad news is that the same technology is killing jobs left and right. For many students and working adults, taking a shot at business becomes one of the few real ways out.
One way out of the “permanent low” is to invest in the very companies that make our skills obsolete. If you can't beat them, at least have a piece of them. It's a bad trade-off, especially for anyone who hasn't reached financial independence, but ignoring it doesn't make it untrue.
The problem is that most people don't know where to start. So by going through how different entrepreneurs have built their own paths, I hope to give you and the readers a clear idea of how to start being your own creator.
Growing up in Mexico with an Owner's Mind
Domingo grew up in Monterrey, a city known for its industrial roots and business culture.
Many of the origin stories of California founders begin in a Berkeley dorm or a Palo Alto garage. Domingo started long before he came to California. You grew up in an environment where starting a business wasn't something you whispered about. 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 entered the field of technology. Like many inventors, his path was not a straight line. This is rarely the case.
Building Capacity in the Mobile Wave
Appthority was born just as smartphones were taking over the workplace. Suddenly every employee was walking into the office with a powerful computer in their pocket, loaded with applications that no one in IT had tested. That created a new security problem, and Domingo built a company to solve it.
From the outside, the startup looks clean. An inventor sees a problem, builds a product, raises money, and comes out rich.
The reality is years of uncertainty, recruiting, fundraising, traveling, and praying. Most startups never reach profitability, let alone acquisition. What impressed me is that Domingo and his founders are determined to continue until the money runs out.
Living with that kind of uncertainty is harder than it looks, which is why I've never done it that way. I preferred to keep a full-time job and build Financial Samurai on the side, and only took the plunge when there was a real result. That jump came two years and eight months after I started, not on day one. Domingo made a bet first and sought 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.
Happy Exit
In 2018, Symantec acquired Appthority.
For a founder, discovery is validation. Years of sacrifice, late nights, and tough decisions finally got the stamp of approval. It is a time when budding entrepreneurs prepare. Announcement, dinners, phone calls.
And then real life goes on.
Plot Twist
This is where Domingo's story stops sounding like a press release.
In 2019, Broadcom acquired Symantec's enterprise security business for approximately $10.7 billion. Appthority took him along for the ride. So Domingo, who had already sold his company, suddenly found himself inside a large company as part of a second acquisition.
On paper, this was a high price. He was earning the most money he had ever made in his life.
And he was sad.
I'll let him explain that part himself in the episode, because it's the most moving part of the conversation. Gold handcuffs are still handcuffs. They just get a little angry.
I have long argued that there is satisfaction in being your own boss, and Domingo's response supports my belief. What he does next is the part that I find most instructive, and that's when the episode moves from the original story to something more useful for all of us.
My Big Takeaway
The lesson from Domingo is not “go start a company.” It's more subtle than that.
There is no one right path to financial success. Some people build corporate-backed rockets. Others are building lifestyle businesses. Others climbed the corporate ladder. Others invest consistently for decades and win quietly.
The important thing is to choose the path that fits the life you really want, not the one that looks best on LinkedIn. Know yourself.
For me, freedom was more than getting a big salary, which is why I left in 2012 at the age of 34. For Domingo, building beats staying comfortable, even when staying comfortable comes at a premium. We both bet. We have both given up something to get something better.
A safe road feels safe until your employer reminds you that you have been making choices. Betting on yourself sounds scary until it becomes the most obvious decision you've ever made.
Listen to the Full Episode
If you've ever wondered what it really takes to build a venture-backed company, raise money, sell it, survive the rig you bought, and then have the courage to start over, this interview is for you.
Listen on Apple Podcasts or Spotify. And if you get something out of it, the single best thing you can do is hit the register and leave a quick rating. The review is how new listeners discover the show, and it takes about 10 seconds.
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