Here’s What Happened When I Made My First Ten Million Dollars


In 2005, I sold my first startup to a NYC-based company, Bolt Media, for mostly stock.  My ownership in Bolt was about 33%.

Prior to selling my startup, I was making a few hundred grand per year, for a few years.  I thought I’d be worth one hundred million dollars within 5 to 10 years. Hey, why not me?  The first thing I would do is retire my Mom and buy my parents a house.  Every son’s dream, right?

The Bolt team was badass.  These people invented homepage takeover ads, contest hubs and many other cool display sponsorship ads you’ve undoubtedly seen.

By mid 2006, I was the President of Bolt.  We grew from 900k monthly visitors to 20 million.  We were featured in AdAge, Mediapost, NY Times, Financial Times, and many others.

We were on top of the world; Nothing could stop us now!

What was Bolt?  We were a leading online video sharing website.  You know, like that other website, YouTube.  In fact, we actually had more traffic than YouTube for a short while.  That is until NBC sent YouTube a copyright takedown notice when a YouTube user uploaded the SNL skit “Lazy Sunday“.  The media attention that followed that copyright takedown notice sent YouTube’s traffic growth into the stratosphere.

It also made all video sharing websites the hottest thing on the planet at that time.  And Bolt was now the #2 video website on the internet, next to YouTube.

YouTube eventually sold to Google for $1.65 billion.  And my ownership in Bolt was now worth well over $10 million.

I was a paper million biatch!

A week after Google bought YouTube, Universal Music Group filed a lawsuit against MySpace, Grouper, and you guessed it, Bolt.

Shit, how much is my stock worth now?

Within a year, we signed a definitive agreement to sell Bolt for $30 million.  I would make about $10 million from the transaction.

The press covered our story, heavily.  Within days, we were contacted by and meeting with wealth management investment bankers from Goldman Sachs to JP Morgan to tell us how to invest the money we would make from the sale of the company.

Everyone I knew was congratulating me.  These investment bankers said everyone would come out of the woodwork though.  I became super skeptical and wondered, were they genuinely happy for me?  Did they resent me?  Did they want something from me?  These bankers were in my head…

Like Biggie said…


I was in my mid twenties at the time.  I thought I’d retire, buy a house on the water, and be on the boat everyday, for the rest of my life.  Could I really retire in my mid twenties though?  Is $10 million enough to live on for the rest of my life?  My grandfather kept telling me that in 30 years, I’d need a wheelbarrow of money just to buy a loaf of bread.  He’s crazy.

Wait, I’m getting ahead of myself.  We haven’t even closed the transaction yet, but what’s the likelihood that this deal doesn’t close?

A few months pass, and our buyer renegotiates the deal and now, I’m not worth $10 million anymore.

I went from thinking I’d be worth $100 million in a couple years, to being worth $10 million, to not being worth the paper the stock was printed on!

What happened?  What about Mom’s new house?  FML… “No Money, MO Problems”.

So let’s recap.  I made ten million bucks, lost it all, and had to go back to work.  Nobody was calling me now.  Pretty depressing, but that’s life.  Poor me.  So now what?

There’s a saying, “necessity is the mother of invention”.  So I started a new company called Yashi, immediately following Bolt.

Six years later, Yashi has generated tens of millions of dollars in revenue and profits since 2007.  It generated over $14 million in revenue in 2013 alone, which is up from $6.4 million in 2012.  Yashi has been profitable since inception too.  That makes my ownership in Yashi worth tens of millions of dollars on paper, but this time, I’ve made a few million bucks along the way too.

I’m now married with two kids, so my priorities have changed a bit.  I still want to retire my parents and buy them a house, but for right now, I’ve finally bought that house on the water and my dad docks his boat there.


So why haven’t I sold Yashi and retired?  Because we’ve built a really cool company and I really enjoy what we’re doing and the people I’m working with.  My co-founder is actually my wife Caitlin, and two of my best friends that I grew up with also work with me now!

Life is good.  However, for all I know, it will all evaporate again tomorrow.  Anything’s possible.

Oh yea, I also bought a wheelbarrow.

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Jay Gould

Jay Gould is the co-founder at Yashi. He also invests in tech startups with his wife through their fund, Gould Ventures.