Hugh Turned His Financial Losses into Profitable Lessons – and a 7-figure Sale on Flippa

Hugh Grossman, on a career path with a Fortune 500 company, entrusted his retirement savings to a financial advisor without paying much attention to where his money was being invested.

Regular statements from his advisor went unopened until one day, Hugh was shocked to discover that half of his capital was gone. He quickly called his broker and, as you can only imagine, exchanged a few choice words before ultimately seized control of his account. That is when he realized two important things: no one cares or should care more about his money than himself, and with the power of the internet, we all have the same information available at our fingertips as anyone else.

Hugh realized the need to manage his own retirement funds. He took many courses, learning all he could about direct investing in the stock market. Eventually, he discovered some very profitable strategies, garnering the attention of his friends and associates. They coerced him into teaching them how to trade and ultimately, Hugh found himself helping other traders how to make some serious money trading stock options.

This marked the beginning of DayTradeSPY and a lucrative 12-year journey for Hugh, his family, and thousands of others. One that would eventually end with a life-changing sale.

Learn how Hugh built DayTradeSPY, monetised his own knowledge, and then found the perfect buyer on Flippa, resulting in an impressive 7-figure sale.

The Early Days of DayTradeSPY

Hugh’s background was in corporate America as an internal auditor for an insurance company. He learned the stock market, started trading on his own, and developed a few successful strategies. 

After making money and recovering his losses, people began to ask him to show them what he was doing. This led to the creation of DayTradeSPY.

Initially, DayTradeSPY was an inner circle with a few subscribers. Hugh would post what he was trading every morning and provide a follow-up report later in the day. He would also hold a weekly meetup to discuss the stock market for an hour. 

Hugh would publish honest accounts of how he was trading with his readers.

The business grew steadily, mostly through word of mouth, and was monetised through subscription fees of $60-70 per month.

“We had a lot of different people sign up— NFL football players, doctors, lawyers, actors, even a mayor,” recalls Hugh. 

Responding to the demand, he expanded his offerings to include a trading room, e-books, and educational videos, which grew into a comprehensive 10-15 part webinar series. 

As part of the free trading resources, Hugh generously shares his trade knowledge in weekly web classes. 

“We kept our subscribers engaged and informed, which is how we sustained our sales momentum,” he said. 

This business model proved to be highly scalable, allowing Hugh to continue growing his business—with the help of his family. 

“My son was instrumental in running the trading rooms, and if I ever needed to step back from a training session, he would jump in and take over. Meanwhile, my wife and daughter were hard at work with marketing efforts,” Hugh said. 

“We were able to create the impression of a large, established company, which helped us attract more clients and expand our reach. In the end, it worked out better than we ever could have hoped.”

The Inflection Point: Enter Flippa

What began as a simple side hustle for Hugh unexpectedly transformed into a successful business that he never intended to sell. Trading options was initially just a way to earn extra income, but as his subscriber base grew, so did his profits.

 “I thought I’ll just keep this going until it fizzles out,” Hugh said. But the business never lost momentum—one year turned into two, four, and eventually, 12 and a half years.

Selling DayTradeSPY was never on Hugh’s radar. “What were we going to sell? How do I sell myself?” he thought.

Hugh received an email from Flippa. He was curious about how much his business was worth and initially thought nobody would be interested. Despite his hesitation, he signed up and met with his account manager, Fiona.

She presented him with a price/value that seemed too good to be true. “My first reaction was ‘ok, you’re just saying that to get me into selling. I get it’.” Plus, Hugh enjoyed the interaction with Fiona but admittedly, never expected much to come of it.  

THen one day, Fiona brought forward the perfect buyer who offered more than he ever dreamed possible. In fact, Hugh was stunned.  

“Seriously? I couldn’t believe it, I was in shock,” Hugh said, “I remember telling Fiona, ‘I’ve never been as impressed with anyone as I am with you.’ She was so professional, so friendly, and made the whole process so smooth.” He still ponders how she pulled this off!

Fiona introduced them via Zoom. As it turned out, they were planning to start their own trading room to complement their publishing business but didn’t know how to start. So when Fiona approached the buyer, the timing was perfect, and Hugh’s business turned out to be an ideal fit.

Hugh found himself staring at the initial deposit in disbelief. “It was hard to believe that this was actually for real.”

At the time of the sale, DayTradeSPY was firing on all cylinders. Not only was it generating a monthly profit of $29K, but it also had an impressive email subscriber list of 14K highly engaged users. Even better, the business was operating with a 94% profit margin.

Managing A Smooth Transition

Managing the transition with Hugh’s long-standing clients (some up to 10 years!) was a delicate process that required careful consideration. 

“One lady was in tears, so instead of just leaving, I introduced the new teacher and explained that we were expanding our team. And the aim was to gradually shift more responsibility to him,” Hugh said.

Hugh is working closely with Ahren in the transition.

“We’ll be working closely together to ensure a smooth transition. It’s like killing off a character in a TV show— you have to do it carefully and with the audiences’ emotions in mind.”

Despite initially planning to stay for only three months until the end of December 2022, Hugh is extending his help (pro-bono) with the transition process. He has been teaching and bringing the new team up to speed but he and the buyer agree they still require more time before he can fully step back.

“This is good for me. Mentally, this is all I did for the last 12 and half years so suddenly to have this void in my mind would be upsetting for me. So I’d like to step down gradually which is what we’re doing, and I’m putting more responsibility on them,” he said.

Advice From Hugh

Hugh’s sale of DayTradeSPY taught him a valuable lesson: always keep an open mind, as opportunities can arise when you least expect them.

“Even if you don’t want to sell, it’s still worth a chat. You might be shocked at the value and opportunity—like I was. And sell when you’re in your high, to get the most value. It seems like there is a buyer for everything!”

“I might find something else to buy and build, and sell it! That’s where the money is.” 

Hugh said he has nothing but praise for Fiona who found the perfect buyer and made sure the deal closed smoothly. 

“Everything Fiona Laidlaw and her team at Flippa have done has been beyond my wildest expectations. I highly recommend her for your online business buying and selling needs. She is professional, well connected, resourceful and a sheer pleasure to work with!” 

Inspired by this story? Read up on others who have successfully bought and sold their businesses here.

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Like this buyer and seller, you too can master proper buyer and seller communications etiquette. We’ll show you how to that here.