How I Make $3K/Month Off My Retirement And Personal Finance Blog As A Side Hustle

Published: May 13th, 2023
Josh Dudick
Founder, Top Dollar
Top Dollar
from New York, NY, USA
started June 2022
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Hello! Who are you and what business did you start?

I'm Josh Dudick, and I'm the founder of Top Dollar Investor. I started the company in 2022 as an extension of my own wealth management business, which I first launched in 2019.

After a successful career on Wall Street as a trader and market strategist, I had a proven track record of smart investing and market-beating returns. I decided that although everyone did not want to invest the way I did, I still had a lot of knowledge to offer.

Most individuals would like to improve their pinances and get closer to achieving financial freedom. I determined there was a lot of poor content on the internet, and there was still room in a crowded field to distinguish myself with higher quality advice and content.

At Top Dollar Investor, we focus on providing free content for everyone crossing multiple socio-economic brackets and geographic locations. Customers only have to be interested in financial education, and I make money through advertisers and affiliate companies that I pndorse and offer quality and reasonable products and services.

Top Dollar Investor is currently making between $1,000 - $3,000 per month.


What's your backstory and how did you come up with the idea?

I am a finance nerd. I spend way too much time reading, talking, thinking, and researching investment and money-saving ideas. My obsession has also proven to be profitable, not just from intelligent investment, but sound money management and tax saving techniques that I come up with on my own.

For example, I changed my accounting method for my brokerage accounts to a FIFO accounting method - which is allowed as long as you are consistent once you set a method. I determined that this would allow me to be more tax efficient when rebalancing and trimming positions. Over time stock prices rise, and your most recent purchases are usually higher priced than older purchases. This cuts realized capital gains and taxable events.

I uncover opportunities like these in my content and provide this information free for everyone.

In the media content business, you need grit and the ability to keep showing up and putting out content

When I mentioned the idea to friends and family that I would start sharing this content, people naturally thought it was a great fit and validated my ideas that this is a valuable and necessary business.

At the time of creating this side hustle, I was, and still am, managing a multi-million dollar investment portfolio. I try to find at least several hours per day to create content and manage the Top Dollar business.

Take us through the process of building the first version of your product.

The first version of my content was based on sound ideas but was written poorly. I am a quantitative personality, and my new business required certain writing skills which I didn't quite possess. I put out content that I felt contained high-quality ideas, but the writing itself was unimpressive and difficult for the reader to follow.

My original plan was to deeply cover personal finance, starting with basic content for beginners such as highlighting the value of retirement accounts and index funds. MI plannedto also cover more advanced concepts for readers interested in learning more sophisticated strategies such as portfolio building, tax loss harvesting, and tax-optimized rebalancing.

Originally I targeted very competitive keywords such as investing in funds, retirement accounts, 401(k), and Roth IRAs. I would write articles that were over two thousand words and build my graphics for articles and my website using Canva.

Learned later that I would have to target more niche terms and engage new readers by discussing less popular topics on which I had more unique expertise on such as specific differences between specific ETFs.

As I have gotten better at creating more content, which is the lifeblood of my business, I understand that people want to learn but also be entertained. I have mostly come to this understanding by networking with other successful bloggers and figuring out what is working successfully for them. I now spend more time making sure my content is both interesting and captivating. Entertaining your audience is never a bad idea.

Describe the process of launching the business.

I spent the first three months focusing on many aspects of the business that now seem silly. I wanted the website to look impressive but wasn't happy with several themes, logos, or even business names that I brainstormed. It took about two months of making virtually no progress on the business before I started to start writing and get going.

Entrepreneurs say the most important first step is to just get started. I originally spent too much time thinking and planning.

Original costs included buying a domain and renting web hosting, which is under $100 per year.

Then I started investing in search engine optimization (SEO) tools to help format my writing to perform better in search tools like Google. Overall initial investments totaled about $2000 for the first year. I think you can start this type of business with much less, but it will take longer to try things that do not work at all.

Since launch, what has worked to attract and retain customers?

SEO has taken about six months to kick in, and now I see organic traffic coming from Google as people find my content naturally. I have days where my site generates up to 2000 visitors and less busy days where the traffic is around 500.

Emailing my visitor to reengage and bring back visitors has helped in creating a regular following. Meanwhile, SEO is an important tool in finding and reaching new potential readers and subscribers.

I have tried some ‘digital PR’ type campaigns to drive awareness and traffic, but most of these efforts have not been too successful. Advertising using social media to reach my target demographic directly has been successful, with my favorite mediums being Twitter and LinkedIn.

How are you doing today and what does the future look like?

It has taken months of hard work, but today I am happy to have consistent traffic I can monetize through ads, affiliate marketing, and also with private coaching sessions. I am spending almost zero on customer acquisition currently and focusing my efforts on free customers through SEO and social media outreach.


75% of my traffic and revenue is from organic search, mostly Google. Therefore I am doubling down on what works and spending more effort on creating content that will rank well on Google.

My average sessions are about one hundred seconds, and I plan to try to increase that over the next six months with more engaging content and leading my readers to more related content.

Monetization is very competitive in the finance and money niche, so I think you have to differentiate yourself and offer something your competitor can not. For me, my hook is that I am an experienced and successful portfolio manager that has outperformed the markets for several years consistently. It is hard for other journalists, writers, and content creators to able to analyze companies and strategies without my 15+ year background on Wall Street.

Trying to make money off ads alone will prove extremely challenging, even with consistent content production and quality content. Differentiation is the most important factor in gaining and retaining an audience.

My long-term goals for the business are to reach 100,000 visitors per month. I hope to realistically achieve this goal within two more years using my same strategy. Additionally, I plan to release several courses over the next year selling more advanced techniques of investment and personal finance strategy.

Through starting the business, have you learned anything particularly helpful or advantageous?

I have mostly learned that you have to keep trying everything and be flexible. I had a vision for what this business would look like when I started, but some things seemed to work, and other things flopped. You have to move in the direction of what your audience and customers want, not what you want.

I think in the media content business, you need grit and the ability to keep showing up and putting out content. The business model is quite simple, but it does require continuous grinding and effort.

The entire SEO world is a black box outside of anyone's control. No one quite understands what is necessary to become important in the eyes of Google and the internet. TMany articles are outrankingme that are produced by non-experts pitching bad advice. I've learned you have to accept that there is no formula for success besides showing up at keeping at it.

What platform/tools do you use for your business?

I built my site and content off WordPress and would recommend the same for any new site owner building themselves. WordPress offers the most customization and flexibility when it comes to placing ads, controlling site speed, and customizing features to meet the needs of your customers.

Social media is imperative for any successful business in the 2020s, and I primarily focus on Twitter and LinkedIn. I like these platforms because they offer immediate engagement and feedback from your direct audience.

You can simply ask, "Would you rather learn about X or Y" and they will tell you in real-time. You can use this valuable line to your customer and audience to curate your content directly to their demands.

I use LinkedIn because I have a strong network within the finance and wall street community and target content that I know will interest the demographic I am targeting. I want to write pieces that investment professionals will find interesting and learn from and LinkedIn has proven to be the best form of social media to tap my professional network.

I use Twitter to reinforce the content I produce and make sure followers who have expressed previous interest but may not scan my site frequently, are aware of any new articles or studies I have been working on that may interest them.

I don’t specifically credit social media on its own for any success, but rather as a tool to help you stay in the frame of mind of your customers and readers. I don’t think these sites have driven a significant amount of new referrals, but rather keep my community aware of new content and coming back to stay informed.

What have been the most influential books, podcasts, or other resources?

I listen to a lot of podcasts. My favorite podcast in my niche is Authority Hackers, which discusses SEO marketing strategies and how to launch new content sites on the internet.

Within the finance space, I recently have been listening to 'Afford Anything' by Paula Plant. I think she brings on an interesting mix of expert speakers to discuss their pet projects and interesting ideas.

Advice for other entrepreneurs who want to get started or are just starting out?

As I mentioned previously, stop planning and start doing. You learn way more by starting the process and immediately getting feedback on what you enjoy doing, what works, and what ideas don't aeet the needs and wants of your audience.

You could write the best business plan, but most new businesses fail, and it's not because of a lack of organization or a bad idea. OAgood business idea is important, but the execution is key and what separates most successful entrepreneurs who have viable business ideas.

There is no one size fits all solution for every business. For me, Facebook has been a time suck and has not produced the community I have tried to build. So I reallocated my limited time and double down on the platforms that are showing more referral traffic- such as LinkedIn and Twitter.

Are you looking to hire for certain positions right now?

I am always looking for writers. I am currently experimenting with content outside the personal finance and money genres, so I am interested in writers for any niche.

The trend seems to be cross-niche all over the internet, with traditional finance sites putting out entertainment and lifestyle stories as well. I will take on any new writers and provide guidance and training.

Where can we go to learn more?

Please reach out to me and check out my content. I put out new articles every day.

Josh Dudick, Founder of Top Dollar
Pat Walls,  Founder of Starter Story
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