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A rabbit hole of entrepreneurial history, all sparked by one $20M mansion.

Setting the stage: millionaires as far as the eye can see (of course)

I’m fortunate enough to live in a seaside city of Southern California. Being an oceanside town, and one in California, it’s definitely among the more (most) expensive places you’ll find in the U.S. (maybe in the world). That simply means that neighborhoods full of multi-million dollar estates are not exactly unusual around here; they’re pretty much the norm.

However, that said, there are still some houses that are such architectural masterpieces they’ll take your breath away. These are the elite of the elite, typically owned by the uppermost echelon of society in terms of wealth, and of course, the price and unique, impressive architectural design reflects that.

While I am a bit of a real estate enthusiast (and would gladly pay a hefty fee to walk through every single mansion on shows like Selling Sunset), some houses raise more questions than simple curiosity about the layout and interior design. This was one of those houses. It was so massive, so impressive, so unique, so customized, so spectacular (far surpassing 99% of the already amazing houses I had seen here in these oceanside cities of Southern California), that my curiosity led me down a rabbit hole that proved very interesting.

Of course, I wanted to find the address*, see the listing (to determine the estimated price), and ogle over pictures of each room, floor, pool, and tennis court. But there was something I wanted even more: to know whose* house it was and how they acquired the massive wealth to afford a house like this in the first place.

*Just a heads up: I won’t be disclosing the identity of these owners or linking to the listing with the home address. This article isn’t about connecting a person to an address, but rather unraveling the impressive entrepreneurial history that led to such an incredible architectural masterpiece. That said, everything included in this article is entirely public information, freely accessible to curious people like you and me, just a few keystrokes away…I simply put the puzzle pieces together, culminating in the conclusion that is this post.

This question actually came up as I was on a hike with my fiance. We were hiking in the Pacific Palisades hills, among your typical four to seven million-dollar mansions. There was the odd eight-figure estate here and there, but nothing out of the ordinary.

Spotting the real estate unicorn and the ensuing bets

And then, across the way (separated by a green area, a non-hikeable hill, and one or two streets) was a new mountain of mansions. Smack dab in the middle of this green mountain was a palatial home so jaw-dropping we were stopped in our tracks. We took pictures. We admired. We googled (trying to locate the exact address on a map, to find the Zillow listing)…And, most importantly (to the rest of this article), we took bets.

We took bets on the type of person who probably lived there. My fiance thought famous athlete. Maybe some big shot in the entertainment industry. Both could have been possible, given that this was L.A…but I wasn’t convinced. Then, my fiance changed his tune a bit and decided celebrity athletes and entertainment icons typically prefer a bit more inland, more so in Bel Air, Beverly Hills, and West Hollywood. And he wasn’t wrong.

So, he decided it must have been finance money. Perhaps someone who worked their way up in banking, like a managing director at Goldman Sachs. I disagreed; it would take too long to amass that kind of wealth in that industry; the owner would be in their 50’s or 60’s and have less use for the many athletic amenities (pool, tennis court, basketball court, etc.).

He then thought hedge fund owner or partner, which is possible. They would most likely qualify from the wealth perspective, but I just didn’t think it was their style. It was too creative, too customized, and too intentionally jaw-dropping. This house was a carefully crafted masterpiece and whoever owned it and commissioned its building in the first place knew exactly what they wanted and was going to ensure they got it (or had it created).

That’s largely why my guess was entrepreneurship. I thought it had to be someone who made it big with a startup, sold their company, and finally got to enjoy those entrepreneurial millions*(*cough: tens of millions+).

Well, now that my wheels of curiosity had started turning, I couldn’t just leave it at that; an unsolved bet. I had to get to the bottom of it, and that’s just what I did.

First, I used the “satellite view” mode on Zillow’s maps to narrow in on the exact house and determine its address. This wasn’t as easy as it might sound. The house was not for sale, and what made it even more difficult is that while I guessed the house was worth at least $12 to $20 million, I also had an inkling that the owner may have had it custom built. That would mean the last Zillow sale price on the property might actually reflect the price of the lot (when purchased by the owner), not the adjusted price of the finished architectural masterpiece.

In fact, unless the house had changed hands since being built, I probably wouldn’t even be able to find a listing with pictures and relevant price history to confirm this was the right house…

Unfortunately, my suspicions were right. The owner had purchased a lot (for a small fraction of the house’s current value), and there were no pictures or relevant price history for this piece of architecture. Luckily, though, the unusual nature of the estate’s layout enabled me to find it in Zillow’s satellite view, as there are only so many mansions on that Palisades hill that boast a tennis court, basketball court, and rooftop pool. Address confirmed? Check.

Now the fun would begin: identifying the owner. These days, most of us may be self-proclaimed internet stalking aficionados (myself included), but few realize the power of a site like Whitepages. This is in no way sponsored or an affiliate link; I’m just saying, Whitepages has helped me ferret out my share of both personal and business connections, whether through reverse address or reverse phone lookup. I only have a premium Whitepages account because years ago, one of my startups had to verify the address of the talent and managers we were working with, so it really has been a business expense for me. This time, however, it would hopefully answer all my lingering questions…

Well, that was the hope, but not really the expectation. You see, having used Whitepages to confirm the address of high-profile talent and their managers, I was used to a very common problem among the mansion-owning elite: they often don’t like to have their names listed in Whitepages next to the house they own. This opens them up to the threat of real stalking, which could obviously be very frustrating and dangerous.

Therefore, many celebrities and prominent figures choose to list their estate planner or management company as the owner of the home (on sites like Whitepages), so the exact address can’t be traced back to the particular homeowner by rabbit hole dwellers like me. Sometimes when this happens, you’re SOL (out of luck). However, to my surprise and delight, these owners were not quite that elusive. In fact, one of them did have their names listed…so the journey would continue!

Once I knew the name of one of the owners, the next step was professional stalking. What had this woman done to amass such wealth to build the mega-mansion to top all mega-mansions?

The one owner I found (who was listed on Whitepages) had an impressive professional history, and initially, I thought she was the answer. She had an undergraduate degree in economics from a top public university, along with an MBA from the same school. Her career began in accounting, then transitioned to high-level finance, and culminated in her current role as the co-founder of a digital startup in the beauty and technology space. If we stopped right there, it would be plausible that she held the keys to the $20-million mansion. Of course, she does hold the literal keys, but there was one flaw to this theory. By Zillow’s current estimate, the house (with no accompanying pictures) was currently worth about $25 million.

When I dug a little deeper into the startup of which she was listed as a co-founder, the numbers are what threw me off. It showed $30 million as their highest annual revenue. The company had never been sold, and they weren’t necessarily profitable. They also had a few different co-founders, so this homeowner herself couldn’t be pocketing the $30 million. Plus, the $30 million in revenue was a recent milestone; in years prior, the startup had been climbing up the low-seven-figures…meaning this co-founder would likely not have amassed enough money from this startup alone to afford that house, especially not six years ago (in 2015) when she had it commissioned.

This was where things got interesting. If it wasn’t her, then who could it be? An inheritance, perhaps? Or maybe an even more successful spouse…? I did look into the inheritance, and while I do think this owner came from a well-to-do family that had a somewhat notable business presence, it still wasn’t likely the answer I was looking for. I was looking for at least $30M+ net worth, and likely a lot more, to splash out that much money on just one property…

Now it came time to Google the spouse — and I’m so glad I did. He was actually pretty hard to find. Even though these homeowners had clearly attained massive financial success, you wouldn’t very easily find them on Instagram or Facebook…in fact, the way I found him was pretty strange. You see, the woman sat on the board of a non-profit, and she also volunteered at her child’s school (which matched the district of the mansion). The child’s school had an event with the non-profit and mentioned the kids and parents involved, and both she (the woman on the board of the non-profit) and her elusive husband were listed. Perfect — I finally had a name.

And he was not quite as anonymous as he might have liked to be…it’s pretty hard to be anonymous when you’ve inked a $485-million dollar deal with a major multinational company and have been one of the glorified headlines to participate in a success of the dot-com-boom. Well, that’s exactly what he did. Oh, and by the way, once I figured out the major success (that bought the $20M mansion), I was also finally able to connect the dots to the tech and beauty startup (of which his wife was listed as a co-founder).

But here’s the interesting thing about this whole PriceGrabber situation, and proof that startups can be a winding road…and sometimes it all comes down to timing and taking money off the table when you have the chance. In 2005, Experian bought PriceGrabber for $485 Million (and Mr.$20M mansion pocketed his portion of the proceeds to fund his future estate).

So, of course — being the tech genius and successful entrepreneur that he is, and given the fact that his company was bought by a huge multinational corporation that’s still alive and well today, it must have appreciated significantly in value since then, right?

It must be a multi-billion-dollar company by this point…surely?

In 2012, Experian attempted to sell PriceGrabber at 25% of the cost…so seven years later and down 75% in value? I’m guessing that wasn’t the plan when they purchased it…

About that homeowner…

Oh, and perhaps I forgot to mention one key thing…the actual tech genius behind PriceGrabber and all the success to follow? It actually wasn’t this $20M homeowner at all. It was his business partner, a more experienced veteran entrepreneur (nearly two decades his senior).

In fact, the only reason this homeowner had the opportunity and funding to participate in PriceGrabber’s origins in the first place was due to his business partner and senior mentor, who had already exited a prior startup of his own and pocketed a nice little nest egg for himself. Between this business partner’s recent cashout and the startup credibility that success afforded him, he raised a modest $1.5 million, which was enough to get PriceGrabber off the ground.

What all can we learn from this?

• Things aren’t always what they seem. By the pure looks of it and a cursory, superficial search of homeownership, we could easily assume the wife’s career in finance and her current beauty and tech startup were the answer behind the $20M+ estate. Digging deeper, it seemed it was her husband’s earlier startup success, and digging even deeper, it seems he was offered a (necessary) helping hand in that success from the get-go. Plus, the $20M+ estate owner didn’t even buy the house for that price. They bought the lot for $3.9 million in 2010 (according to Zillow’s price history), then hired the architects and had the mansion custom-built to perfection sometime between then and 2015. The build is estimated to have cost about $7 Million (according to PropertyShark), taking them to about $11 Million in value, and price appreciation in the area has resulted in a current Zestimate (Zillow price estimate) of about $25 Million today, as of this article.
• Networking and professional connections may matter more than you know. The husband never would have had the opportunity to hop aboard PriceGrabber’s founding team (and be granted a fistful of valuable equity) if he hadn’t worked with and met his business partner and senior mentor, who was actually listed as the CEO of PriceGrabber at the time of that $485 Million exit. In fact, his entrepreneurial career may never have begun at all, without that one incredibly valuable connection (that easily changed the trajectory and success of his career and future endeavors forever).
• Timing is everything in business. PriceGrabber was purchased for $485 Million in 2005, six years after its founding. However, in 2012, Experian (the company that bought PriceGrabber for $485 Million) agreed to sell it to Ybrant Digital, at a quarter of the cost. That’s a huge loss, seven years after they should have seen the startup continue to climb in value. What happened to the billion-dollar valuation for which it was on track? The sale fell through (also probably not a great sign, if they couldn’t even get rid of it for a quarter of the cost), and Experian sold the business back to the management team at the time (for an undisclosed amount). Three years later, in 2015 — the same year the PriceGrabber co-founder and his wife had the mega-mansion built — the management team sold PriceGrabber to Connexity, also for an undisclosed amount. By this time, by the way, both the $20M homeowner and his senior business partner and mentor were a decade out of PriceGrabber, so they had already taken their gains and absolved themselves of future risk…and that proved to be a pretty smart move.
• Yes, those mansions on the hillsides of Los Angeles may be owned by a wider variety of successful people than athletes, celebrities, and finance professionals. In fact, I’d venture to guess that many more than we know are. That’s probably the coolest thing about living in L.A. While the immense wealth and conspicuous consumption can be seen as a materialistic, money-hungry culture that poisons the minds and hearts of its inhabitants, I would tend to disagree. I think the massive wealth offers something else: a myriad of inspiring case studies of success that we can investigate and learn from. If I didn’t think it was inspiring, I would have moved away long ago. And some people do. Some people find wealth like this offputting. Others find it intimidating or possibly even discouraging. I find it teachable, and I believe there’s a lot we can learn if we dig deeper into the outliers that populate Southern California’s seaside hills (or anywhere full of extraordinary, in many cases self-made, successful entrepreneurs).

For those curious to see inside the house, I’ve linked below to the feature story on its architect’s website (which does not include the address, but rather focuses on the immaculate design, and states the house was completed in 2018, which would imply a three-year build time from the 2015 commission date). This 17,000-square foot estate is truly a one-of-a-kind masterpiece, and it has won awards for being just that.

In case you’re wondering why I went all the way down this rabbit hole…

Am I an investigative journalist? No. Private investigator for hire? Nope. Professional spy? Definitely not, though it could be fun…

At the end of the day, I’m just a girl with a real estate addiction and a startup obsession, putting my curiosity and technology to work for all of our benefits (or so I hope).

Final thoughts on the mega-wealth and extreme success behind seaside mansions and homeowners like these?

If you can’t beat them, join them.