How I made $2 Million in Side Hustles and Passive Income
I have netted over $2 million dollars through a variety of side hustle investments over the previous 15 years including stock market investing, internet site income, real estate rental property, and flipping a business. This income does not include my primary work income (day job) or primary home ownership (residence appreciation).
My definition of “side hustle or passive income” is income or profit generated outside of your primary job income or appreciation in your primary residence.
In this blog post I will list out the details of the side hustle, my investment, my approach, why I sold, and my net profit or loss.
I will include my active side hustles which include:
- Stock Market, ETF, and Dividend Income
- Internet BLOG income
- Internet Software Business
- Passive Investments
I will then document my “closed” side hustles including my investment, my approach, why I sold, my profit / loss, and lessons learned.
So let’s jump in.
Past Side Hustles and Passive Income = $2 Million
Side Hustle: Blog Site $72k Profit
Online Website Directory
What is it? I bought an online directory in 2019 for $55k, earning ad revenue.
Why did I buy it? I saw an opportunity to buy an online business for $55k generating $3k monthly, so it would pay for itself under 2 years. It would then generate nice side income over time.
Why did I sell it? Running an online directory was not very interesting to me, so that wasn’t good. Then the business was 100% dependent on Google rankings, which changed constantly so it was very stressful for a side business.
How did I sell it? I was very fortunate to have a competitor make an excellent offer to buy me out, so I did it.
What did the revenue return look like? Here’s the summary below:
- Amount Invested: $55k
- 2020 Income: $35k
- 2021 Sold for $96k
- Running Costs: $4k
- Profit: $72k
Passive Investing: Stock & Bond Investment Portfolio $1.8 million Profit
Passive Investments: Stock, Bond, & REIT Appreciation
What is it? I’ve invested savings from my primary income into a mix of stocks, bonds, and REIT. In my early investing days I lost money by attempting to buy individual stocks. However in 2010 I found bogleheads.org which helped me to learn the boglehead way of investing.
While its slow and boring, it has generated almost $2 million dollars in wealth over 10 years. Here’s a link to the Boglehead way of investing that taught me.
Passive Investments: Portfolio Annual Dividends
What is it? The annual dividends on my investment portoflio generate $85k of annual income.
Why do I continue to invest? Generating and collecting dividends is one of the greatest feelings in the world. However the problem is its only a few % of the total portfolio so it takes years to accumulate. This is why I am building multiple side hustles to supplement income.
College Investment Property: $75k Profit
What is it? I a duplex at a university that I rented to students over a 5 year period.
Why did I do it? I had friends who were buying rentals in college towns, so I learned from them. There is always demand for student rentals if the location is good.
Why did I sell it? While it only took a few hours a month to manage, I began to get concerned about the liability. Plus the appreciation was slow, so it would take me 15+ years before I saw a nice return. I was very busy in my personal life, so decided to sell for a profit.
What does the revenue profile look like? Here’s the summary below:
- Purchase Price: 250k
- Amount Invested: $25k
- Annual Income: $1k
- Sold Price: $300k
- Profit: $75k
Active Side Hustles and Passive Income
What is my objective?
I’m looking to generate $100k annual side hustle and passive income from the Blog and AssetRise internet sites.
I’m looking to generate a $400k profit from the investment property in the next 24 months.
I have a seperate blog post tracking the progress of the Internet sites on my journey to $100k annual side hustle and passive income.
Blog Sites
Bogleblog.com
What is it? Bogleblog is a Blog site focused on the Boglehead investment methodology.
Why did I create it? I created the site to generate Google Ad Sense revenue, affiliate revenue from links to products, and to link back to my SaaS site assetrise.com.
What does the revenue profile look like? Here’s the summary below:
- Amount Invested: $150
- Date Started: Dec 2023
- 2023 Income: $0
- 2024 Expected Income: $500
Hustlemoneyhacks.com
What is it? Hustlemoneyhacks.com is a Blog site focused on side hustle ideas and passive income for individual investors to retire early.
Why did I create it? I created the site to generate Google Ad Sense revenue, affiliate revenue from links to products, and to link back to my SaaS site assetrise.com.
What does the revenue profile look like? Here’s the summary below:
- Amount Invested: $150
- Date Started: Dec 2023
- 2023 Income: $0
- 2024 Expected Income: $500
Dividend Income
Stocks, Bonds, and REIT
What is it? This is passive income I’m collecting on my investment portfolio.
What effort does it take? I’ve been self managing my investment portfolio for over 15 years, so at this point I spend about an hour a week monitoring and adjustment my portfolio allocation.
What does the revenue profile look like? Here’s the summary below:
- Amount Invested: $3.6 million
- 2023 Income: $85k
- 2024 Expected Income: $90k
Florida Investment Property
What is it? I bought land in a popular Florida community for $400k where I am building a home to rent or flip.
Why did I do it? I have invested into my ETF portfolio heavily, so I wanted to diversify outside of stocks and bonds with real estate.
What does the revenue profile look like? Here’s the summary below:
- Amount Invested: $400k
- Date Started: Sept 2023
- 2023 Income: $0
- 2024 Expected Income: $0
- 2025 Expected Income: $450k
Online Software Tool
What is it? Assetrise.com is an online portfolio tool designed for investors to track their portfolio asset allocation, rebalance tools, dividend, and portfolio return in a single dashboard.
Why did I do it? I have spreadsheets to track my portfolio, and I have developed spreadsheets for many others as well. So creating an online tool to fill the void makes sense.
What does the revenue profile look like? Here’s the summary below:
- Amount Invested: $25k
- Date Started: July 2023
- 2023 Income: $0
- 2024 Expected Income: $500
- 2025 Expected Income: $8k
In Conclusion
I’m very fortunate to have success in my investments. In hindsight, I have also missed MANY opportunities that I wish I could have taken back. However that’s the past, what I can control is what I’ve learned from it then drive forward.
The Internet and Digital Media creates enormous opportunities to create wealth through side hustles, passive income, then there’s stock market investing.
I hope you are taking something from my learnings to apply to your own wealth building strategy.
