Romes Blog

Dividend Investing, Financial News, and my Personal Portfolio.


Jay – A Dollar a Day Dividends Interview

I recently met Jay and realized we are alike in some ways. He is a cool and down to earth guy who has a good financial head on his shoulders. He has all the good qualities an investor needs to succeed and I am looking forward to watching him grow his portfolio and achieve his dreams. Thank you for taking the time to interview with RomesBlog Jay, I enjoyed reading what you had to say. We appreciate the support and I am sure this post will help a new investor. If you haven’t already, give him a follow. Socials below!


X – @1DollarDividend
IG – @jiujitsu.jay

Tell me a little about yourself. Your age, hobbies, career, etc. Whatever you feel comfortable sharing.

Hello there! My name is Jay I’m a 36-year-old currently residing in Virginia, eagerly saving up for a new chapter in my life. I have my sights set on moving to Texas. By day, I work as a quality inspector for the aerospace industry.

Outside of my day job you’ll find me immersed in the world of competition Jiu Jitsu, seeking thrills at theme parks, and navigating the exciting realm of investments. Inspired by others on Twitter, I took the leap of faith in July of 2023 and founded my own pressure washing business Pristine Exteriors. My goal is to turn this venture into my full-time pursuit as soon as possible. Fueled by the passion for entrepreneurship and the drive to create something of my own.

How long have you been investing? In addition, what does your portfolio currently look like?

I began my journey in investing during the challenging times of the COVID market crash. It all started with the stimulus check, and though I made my fair share of mistakes along the way, each misstep served as a valuable lesson. Over time, I’ve leveraged these experiences to diversify my portfolio, creating a multifaceted approach.

Currently, my investment strategy spans across several portfolios. One is centered on dividends, offering a more stable and passive income stream. Another portfolio is dedicated to the dynamic world of day trading and swing trading, where I aim to capitalize on shorter-term market movements. Recently, I’ve ventured into the realm of futures and forex, seeking to explore new opportunities and broaden my investment horizons. The journey has been both challenging and rewarding, with every decision contributing to my growth as an investor.

Follow Up

Covid is where I began looking into investing as well. You mention futures and forex, have you had any good luck? I tried forex maybe three years ago and did not enjoy it. I lost money so that is probably why.

In my futures journey, I’m still building my account trading Micros like /MES, /MNQ, and /MCL but I have had some luck thus far. Keeping it simple with just three allows me to build and manage my account without feeling overwhelmed. As for Forex, I’m practicing what I preach – using a paper account to focus on a couple of pairs. Narrowing down helps understand reactions to different situations, boosting confidence in decision-making. Learning and growing everyday!

What made you get into investing? Do you remember your first trade?

Getting into investing was somewhat serendipitous for me. A colleague at my previous job, who had been in the investing game longer than I’d been alive, played a pivotal role. When we learned about the upcoming stimulus check, he suggested I consider putting it in the market. Given my affinity for a bit of risk, I thought “Why not? It’s essentially free money, right?” Little did I know, that decision would lead to some significant gains.

My first trade and a substantial portion of those early profits, revolved around $TSLA (Tesla). The volatile yet promising nature of Tesla’s stock prove to be a rewarding starting point. It’s fascinating how a simple suggestion and bit of willingness to take a chance can set the stage for a journey into the world of investing.

What kind of investments do you prefer? How do you feel about crypto?

When it comes to investments, I don’t have a specific preference. I find joy in exploring various avenues, from the excitement of options and day trades to the reliability of more conservative options like dividends. Each investment types offer its unique set of challenges and rewards, and I’m still in the process of discovering where I feel most successful.

Regarding crypto, I’ve been a believer since it’s early stages back in 2009/2010. Unfortunately, at the time, I didn’t quite grasp how to invest in it. Fast forward to today, and I’ve joined the crypto space, with investments in Bitcoin and various blockchains. The evolution of cryptocurrency has been fascinating, and I’m looking forward to seeing where it goes in the future.

What are your goals for your portfolio?  Is it a never ending process or do you have an end goal?

My portfolio goals are quite diverse, and I like to think of them as “micro goals,” each serving a specific purpose. In my dividend portfolio, my aim is for it to generate enough income to contribute towards covering a portion of my bills and utilities in retirement. Providing a sense of financial security and steady income stream during my later years.

On the other hand, in my day trading portfolio, the ultimate aspiration is to transition into a full-time day trader. This would not only provide the time and flexibility to nurture and grow my business but also open up new opportunities for financial growth and independence.

While these goals seem more immediate, I view the process as an ongoing journey. I see it as a dynamic evolving process where new goals may emerge and my financial journey unfolds.

Follow Up

You mentioned you have a side business before. After your move to Texas, would you continue the pressure washing business or move straight into the day trading? Or do both? I think it’s cool you have the options. Day trading always fascinated me. Wolf of Wall Street probably had something to do with that.

I plan on building up the pressure washing business here in Virginia for the next year or so before the official move. Keeping the funds separate for a proper setup in Texas – branded truck, commercial-grade equipment, the whole deal. Then, transitioning into day trading gradually. Like I mentioned earlier I’m guilty of making mistakes such as letting greed take over during the $GME and $AMC squeeze while I made a lot of money, I ultimately ended up blowing up my first account losing my PDT status. So brick by brick I’m rebuilding to that status again.

If married, does your partner invest with you? Together or separate?

While my wife initially had no interest in investing, I introduced her to the world of finance last year. To make it engaging for her, I set up an account on M1 Finance, allowing her to select stocks of companies she likes and uses such as Target, Starbucks, Apple, and Procter & Gamble. Alongside her choices, I added some of my own suggestions.

We started with a modest $25 per week last year, and this year, we increased it to $30. I’m proud to share that her all-time returns have exceeded 20% and continue to grow. It’s been a rewarding experience not just financially, but also in fostering a shared interest and involvement in our financial future.

Follow Up

That is awesome you and your wife invest together.  I’m hoping to convince my wife to do it with me. Did this help your relationship? Do you two butt heads on any investments?

Not at all, investing hasn’t caused any disagreements between us. My wife zero interest in it, but she trust my decisions completely. Whether I decide to hold or switch investment she’s on board. While it hasn’t drastically impacted our relationship, it does provide us with another interesting topic to discuss. It’s helped her understand a little more of what I’m talking about when I explain things, she’s past the smile and nod phase on to learning about support and resistant levels.

The market has been on the upswing, is it still a good time to buy in your opinion or should people wait?

I believe it’s still a great time to get into the market! Waiting for the perfect moment can be challenging, and timing the market is notoriously difficult. I recommend not delaying any further. If the idea of diving into individual stocks seems intimidating consider using a broker that offers fractional shares. For the who prefer a more hands-off approach, platforms like M1 Finance allow you to set up automatic investments each week – It’s like the old infomercial saying “set it and forget it.” This way, you can steadily build your portfolio without the stress of timing the market.

What are some characteristics you feel an investor should have if they are to succeed?

Patience, discipline, and risk management. These characteristics when combined form a solid foundation for navigating the complexities of the financial markets and working towards long-term investment success.

What advice would you give to a new investor right now? Is there a stock or stocks you would recommend for their first buy?

For new investors starting out, my advice would be to find a broker that allows for fractional share buying. This approach enables you to invest in partial shares of higher prices stocks, making it more accessible, especially if you’re working with a smaller budget.

Consider beginning with index funds such as $VOO (Vanguard S&P 500 ETF), which tracks the performance of the S&P 500. Index funds provide diversification across a broad range of stocks and have a proven track record of long-term success.

Additionally, I recommend opening a paper trading account. This allows you to practice trading with virtual money in a simulated environment. It’s an excellent way to learn how specific stocks move without risking real capital. Once you’ve gained confidence and built a level of success through paper trading, you can apply that knowledge to your real-money account, branching off into individual stocks.

Lastly, what was your biggest mistake when it came to investing?

My biggest mistake in investing has been a series of challenges rather than a single misstep. One prominent issue has been my struggle to consistently follow my established rules, a habit that persists to this day.

Another mistakes I’ve encountered is relying on someone else’s advice without conducting thorough research. Additionally, I’ve found that letting greed influence my decisions, particularly in the realm of day trading, has been a significant challenge.


Hello, my name is David and I have a passion for making money. But then again, who doesn't? I love the stock market because it gives you a chance to better yourself and your situation. My goal is to be financially free by the age of 55 so I can enjoy myself. Join me on my journey and learn a little bit along the way. Thanks for reading! DISCLAIMER – I am not a licensed tax advisor, lawyer or stock broker. I am simply a person who loves investing. Please consult a professional.

2 thoughts on “Jay – A Dollar a Day Dividends Interview

  • Thanks for featuring me Rome. Much appreciated I enjoyed it.

    • No, thank you my friend. Thank you for helping the blog.

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