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 one day decide we're suddenly redundant. I know this path 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 Tips podcast, Domingo Guerra, didn't wait nearly as long as I did. He left at 27. And his story has a twist most people don't see coming. The biggest payday of his life also turned out to be the most miserable stretch of his career.
In this episode, I sit down with my friend and fellow school dad Domingo to talk about his journey from growing up in Monterrey, Mexico, to studying engineering at the University of Texas, to co-founding the mobile security company Appthority with my poker and softball buddy, Kevin Watkins, to selling it to Symantec. Then something else happened.
Today he runs a seed-stage fund backing the founders building security for the AI era. You can listen here by clicking the embedded player or listen on Apple or Spotify.
The Entrepreneur's Journey
I want to start interviewing more entrepreneurs, because AI has quietly handed all of us the ability to become one. The tools that used to require a team and a budget now cost $20 a month and a free weekend.
That's the good news. The bad news is that the same technology is eliminating jobs left and right. For a lot of students and working adults, taking a shot at entrepreneurship is becoming one of the few real ways out.
The other way out of the “permanent underclass” is to invest in the very companies making 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 reached financial independence yet, but ignoring it doesn't make it less true.
The problem is that most people have no idea where to start. So by walking through how different entrepreneurs actually built their paths, I'm hoping to give readers and our children a clearer sense of how to start being a creator of your own. There are so many different ways.
Growing Up In Mexico With An Owner's Mindset
Domingo grew up in Monterrey, a city known for its industrial roots and entrepreneurial culture.
Many California founder origin stories start in a Berkeley dorm or a Palo Alto garage. Domingo's started long before he ever set foot in California. He grew up in a place where starting a business wasn't a fantasy you whispered about. It was just a normal thing 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 wasn't a straight line. It rarely is.
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 apps nobody in IT had vetted. That created a brand new security problem, and Domingo built a company to solve it.
From the outside, startups look clean. Founder spots a problem, builds a product, raises money, exits rich.
The reality is years of uncertainty, recruiting, fundraising, pivoting, 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 looks, which is why I never did it that way. I preferred keeping a full-time job and building Financial Tips on the side, and I only took the leap once there was real traction. That leap came two years and eight months after I started, not on day one. Domingo bet first and looked for proof later. I wanted the proof before I'd bet. Both can work, but it helps to know which kind of person you are before you jump.
The Exciting Exit
In 2018, Symantec acquired Appthority.
For a founder, an acquisition is validation. Years of sacrifice, late nights, and hard decisions finally get a stamp that says it was worth it. It's the moment aspiring entrepreneurs fixate on. The announcement, the dinners, the wire transfer.
And then real life keeps going.
The Plot Twist
Here's where Domingo's story stops sounding like a press release.
In 2019, Broadcom acquired 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 peak. He was making the most money he had ever made in his life.
And he was miserable.
I'll let him explain that part himself on the episode, because it's the most jolting part of the conversation. Golden handcuffs are still handcuffs. They just chafe a little nicer.
I've long argued there's satisfaction in being your own boss, and Domingo feedback supports my belief. What he did next is the part I find most instructive, and it's where the episode goes from a startup story to something more useful for the rest of us.
My Biggest Takeaway
The lesson from Domingo isn't “go start a company.” It's subtler 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 just invest consistently for decades and quietly win.
What matters is choosing the path that fits the life you actually want, not the one that looks best on LinkedIn. Know thyself.
For me, freedom beat earning maximum income, which is why I left in 2012 at age 34. For Domingo, building beat staying comfortable, even when staying comfortable paid the most. Both of us bet on ourselves. Both of us gave up something certain to get something better.
The safe road feels safe right up until your employer reminds you that you were always optional. Betting on yourself feels terrifying right up until it becomes the most obvious decision you ever made.
Listen To The Full Episode
If you've ever wondered what it really takes to build a venture-backed company, raise capital, sell it, survive the corporate machine that buys you, and then have the guts to walk away and start over, this conversation 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 subscribe and leave a quick rating. Reviews are how new listeners find the show, and they take about 10 seconds.
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Thanks, Sam and Domingo. This is so relatable. Curious if the group would mind weighing in on my current situation:
28M, sold my marketing agency, ~$2.7M net worth, trying to figure out the next game
Looking for perspective from people who have been through a similar transition.
I’m 28 and recently sold my marketing agency. The business generated roughly $400k of EBITDA and sold for approximately $814k ($750k cash at close plus a consulting agreement).
Current situation:
Current assets are a mix of public markets, cash equivalents, and private lending opportunities. I’m also building relationships with local operators and business owners.
The challenge is that I’m struggling to determine what game I should be playing over the next 10-15 years.
I don’t want to:
I do want to:
I’ve been exploring:
The question I keep coming back to is this:
If you were 28 years old, had a recent liquidity event, ~$2.6M net worth, wanted to stay in a mid-sized market like Wilmington, and wanted to build toward $10M+ without returning to a 60-hour work week, what would you focus on over the next 5-10 years?
Would you:
Interested in hearing from people who have actually gone through the post-exit transition and what worked (or didn’t work) for them.
If you want to work less and enjoy life more, I would build a lifestyle business that gives you purpose and meaning while investing 80% of your assets in the S&P 500, 10% and alternatives, and keep 10% in low risk Investments.
I was burned out at 34 with about $3 million net worth in 2012, and about $2 million in Invest assets. The net worth figure has grown by multiples since by simply staying invested since the S&P 500 and real estate have done well since then.
Enjoy the freedom on the flexibility!
Domingo captures a lot I had honestly forgotten, probably because my brain deleted it for self-preservation. He also does the classic Domingo thing where he massively understates his own contribution. Without him, I don’t think I would have made the jump. Without him, I don’t think we raise funding. And without him, Appthority probably stays as one of my “great ideas” that I over-explain to people until they slowly back away.
You can have the best idea and product in the world, but the co-founder you trust when things get weird is what gives it a chance to actually become a company.
Highly recommend the listen. Great job Sam, and thank you for giving us the chance to tell the story.
You bet Kevin! Maybe you’ll go easier on me next time we play poker.
Good advice on agitating the market to let the incumbents know what you’re doing, but perhaps not going so aggressive that the incumbents one-shot your product and your company. What a fine line to walk.
Thanks for the chance to share my story, Sam. This conversation was part lessons, part therapy. I hope it helps a few people: founders who think they are not ready, would-be investors who only ever dreamed about backing startups, and employees still looking for meaning in the work. Your “know thyself” takeaway is spot on. The hardest part is being honest about which kind of person you are before you take the jump.
Awesome to have you Domingo and great lessons for everyone thinking about taking the leap of faith in entrepreneurship.
Wow what a great story! Thanks for sharing. I’m always inspired by the unique journeys entrepreneurs go through. It takes so much self motivation, patience and persistence. Very admirable traits that I hope my kids adopt.
Looking forward to checking out this episode! Enjoyed this post Sam!
-Chris (just-cg.com)