Venture Debt – I invested $120,000 in my business school friend’s venture debt fund. He started his own after spending 8 years at one of the largest venture debt funds as a Managing Partner. I’m very focused on income generating assets in this low interest rate environment. The true returns are yet to be seen, as the fund has a 5-7 year life before it returns all its capital.
Do you want to earn $100, $1000 — or even more — on the side? You can start earning extra income today with the help of this list of ideas I’ve put together. Spend an hour or two each day working on items that are practical for you, and you can build alternative income sources to help you improve your financial situation  While many of the items on this list are passive income ideas, not all of them are. Some items require you to actively work for success.
Making legitimate passive income isn’t as difficult as you might think. Some of the best passive income ideas might take a little time to set up but can start cash flowing within a couple of months and will provide a consistent monthly income for years or more. The most important point is just to get started. You make exactly $0 on the passive income sources you never start.
So, armed with my real estate license and this desire to help physicians (and create a business at the same time), I started a real estate company called Curbside Real Estate. My goal was to help physicians buy and sell homes by connecting them to trusted realtors and lenders. It started organically, largely through word of mouth. Next thing you know, I was helping doctors from coast to coast. The business was great and I felt I was making an impact helping physicians, but I still wanted to own my own real estate investment properties.
I have not. While I am intrigued with the possibility of making online income, it seems to be less passive then how I want to spend my time. Regarding your blog / site, you have done quite well for yourself. However, you have to keep pumping out content or your site would eventually go out of business. That sounds like more of a commitment then I would want. Regarding your book sales, it is probably relatively passive now, but certainly was not when you were writing the book. Now if you love it, great. Just not for me.

I will share what we did, because it’s an incredible success story. We used an existing tax loophole where if you sell your primary residence (after having lived there at least two years) you get to keep your profit tax-free. So, we stair-stepped. We bought house after house, at least two years apart, used the profit money to pay down on the next house (so on and so forth, yadda yadda) building up equity as we went along… and now, we own a $600,000 house debt-free. And now we are using our paid-off home as leverage to borrow money to buy commercial buildings to rent out. I like commercial because it’s a BUSINESS transaction… kids, pets, other wear and tear that you see with residential rentals is nonexistent. People take care of their business space much better than residential. You have to be in a good area for renting out commercial – a thriving business community – to make this work. But that’s how we “made it”, and though it took 15 years, we will have residual income to take care of us when we’re old enough to retire. People made fun of us for moving so much, but who’s laughing now? 😉 Oh, and our child only had to change schools once (and we wanted to anyway) because we stayed in the same general area as we moved around. We were careful not to disrupt his life too much.
Because you’re publishing an eBook rather than a physical book, the costs are minimal. And you don’t have to print 1,000 copies of your book hoping someone will buy it. Instead, you can write your book, create a fancy cover for $5 using Fiverr and publish through services like Amazon Kindle Direct Publishing. Amazon will handle everything for you, then take a percentage of the revenue you generate.
Lending Club is a platform where you can lend your money to other people. You’re the bank. Each note is only $25, so you can invest $1,000 and lend money to 40 people. There are many grades of loan (from safest to riskiest) and investors earn, on average, between 5% and 7% annualized returns. For more information, check out Investing and Making Money with Lending Club Peer-to-Peer Lending and my real money Lending Club Portfolio.
For those of you who don’t want to come up with a $220,000 downpayment and a $900,000 mortgage to buy the median home in SF or NYC, who don’t want to deal with tenants or remodeling, and who wants to not do any work after the investment is made, check out Fundrise. They are my favorite real estate crowdsourcing company founded in 2012 and based in Washington DC. They are pioneers in the eREIT product offering and they’re raising an Opportunity Fund to take advantage of new tax favorable laws.
Crowdfunding is a newer way to invest, having emerged onto the scene just within the last few years. Most people have heard of sites like Kickstarter and GoFundMe, and a very similar concept exists for real estate. Developers are always looking to raise capital to fund their projects. Through the various online platforms, investors have access to these projects and can choose to invest in both residential and commercial properties. See the List of My Favorite Crowdfunding Sites.
Crowdfunding is a newer way to invest, having emerged onto the scene just within the last few years. Most people have heard of sites like Kickstarter and GoFundMe, and a very similar concept exists for real estate. Developers are always looking to raise capital to fund their projects. Through the various online platforms, investors have access to these projects and can choose to invest in both residential and commercial properties. See the List of My Favorite Crowdfunding Sites. https://www.listenmoneymatters.com/wp-content/uploads/2017/08/buy-online-business.jpg

We pitched to an angel investor group. They were very excited about the idea but wanted to know who amongst us (doctor, accountant, salesman) was doing the coding. When they heard we were outsourcing it, the wind went out of their sails immediately. They did want to meet with us again once we brought a coder on board but that person proved elusive to find. Coders in our area are looking for the steady paycheck, not willing to gamble on a startup.


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Vanguard: Vanguard has a minimum of $50,000 and a fee of 0.3%. Rebalancing is done automatically once every quarter and tax loss harvesting is done on a client-by-client basis. We included Vanguard because clients who invest between $50,000-$500,000 have access to a team of financial advisors. Those with accounts over $500,000 will have a dedicated advisor.
​Udemy is an online platform that lets its user take video courses on a wide array of subjects. Instead of being a consumer on Udemy you can instead be a producer, create your own video course, and allow users to purchase it. This is a fantastic option if you are highly knowledgeable in a specific subject matter. This can also be a great way to turn traditional tutoring into a passive income stream!
One great way to generate a passive income is through affiliate marketing. Now, this does depend on the size of your list. Yes, size matters when it comes to your list. Especially if you're looking to make some serious money and do it on autopilot. But, list-building takes time. It doesn't happen overnight. And you need to add value to your list or you become obsolete.
I will share what we did, because it’s an incredible success story. We used an existing tax loophole where if you sell your primary residence (after having lived there at least two years) you get to keep your profit tax-free. So, we stair-stepped. We bought house after house, at least two years apart, used the profit money to pay down on the next house (so on and so forth, yadda yadda) building up equity as we went along… and now, we own a $600,000 house debt-free. And now we are using our paid-off home as leverage to borrow money to buy commercial buildings to rent out. I like commercial because it’s a BUSINESS transaction… kids, pets, other wear and tear that you see with residential rentals is nonexistent. People take care of their business space much better than residential. You have to be in a good area for renting out commercial – a thriving business community – to make this work. But that’s how we “made it”, and though it took 15 years, we will have residual income to take care of us when we’re old enough to retire. People made fun of us for moving so much, but who’s laughing now? 😉 Oh, and our child only had to change schools once (and we wanted to anyway) because we stayed in the same general area as we moved around. We were careful not to disrupt his life too much.
Writing an e-book is very popular among bloggers, as many have noted that “it's just a bunch of blog posts put together!” You will not only have to make an investment of time and energy to create the e-book, but market it correctly. However, if marketed correctly (through blogging affiliates in your niche, for example), you could have residual sales that last a very long time.
In order not to succumb to that, Flynn says it’s important to know your motivation. “Passive income is important to me not just for the financial security but so I can spend time with my family,” he says. “I’ve been able to work from home and witness all my kids’ firsts. I have a one-year-old and a four-year-old, and that's what drives me and gets me pushing through those hard times and why I keep creating new products and why I want to help other people do the same thing.”
Ever find yourself humming a tune, or laying down tracks for yourself or friends? Your next catchy phrase might fetch you a solid passive income stream. On sites like ProductionTrax and Audio Network, musicians can license their compositions for background music in apps, commercials, and websites to earn more money. Read more about this strategy at The Guardian.

If you have a specific and in-depth expertise, like programming, coaching, or consulting, then having a well written sales page on your own website can be rewarding. I do this with my web design, SEO, Social media, and coaching services. If you want to become a highly-paid freelancer, I highly recommend you first build your own online platform so you can share your professional expertise, knowledge, and life story with the world. Here's how to start your first website in less than 24 Hours.

When I started building my architecture-related business in 2008, I made my first dollar through advertising. I’d spent a lot of time and money building the site and getting traffic. Then one day I threw an ad on the site one day, and I made $1.18. Sure, I could find that much under my couch cushions—but that’s not the point! The point is that I was able to build something online, put an ad up, and make money without having to do anything. I learned it was possible, and it motivated me to move forward.

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