The Top 5 Most Half-Baked Ways I’ve Tried to Earn Money (And What I’ve Learned)

I’ve always had a tinge of entrepreneurial optimism, if not the business sense to back up my creativity. Though I always stopped short of schemes and scams, here the five most asinine ways I’ve tried to make a buck. What are yours?

I’ve always had a tinge of entrepreneurial optimism, if not the business sense to back up my creativity. Though I always stopped short of schemes and scams, here the five most asinine ways I’ve tried to make a buck. What are yours?

(Note: This article is part of the ProBlogger group writing project. Visit ProBlogger to read hundreds of other “Top 5″ articles by great writers from around the world).

1. Selling Cars – It’s funny; my one month stint as a car salesman inspired my last group writing project post “How to Beat the Car Dealerships at their Own Game”.

After I decided I didn’t like the starving lifestyle of an entry-level New York journalist, I moved back home and thought auto sales would be an easy way to make some good money.

The lesson? I wasn’t a complete failure at sales, so the money was there. But six 12 hour workdays a week made it far from easy.

2. Online Poker – Remember early 2005 when Texas Hold ‘Em was all anybody could talk about? I’ve always had a knack for cards and found most other players clueless.

So I played at night until I was winning a few hundred dollars a week. Of course I was eventually cleaned out by a stronger player.

The lesson? Anybody trying to “earn” money gambling deserves a big smack – myself included.

3. eBay – Though I never actually tried to start an eBay business, I count it here because I wasted so much damned time thinking about it.

At one point I was quite adroit at selling my old or unused stuff on eBay (actually a smart way to simplify your stuff and stash some extra dough). But of course I considered taking it to the next level and becoming a full-time eBay retailer.

The lesson? Without a relationship with a wholesaler (or a way to get one), making money on eBay would’ve been a much harder full-time job than I held.

4. Internet Bubble Start Ups – Today, if you know what you’re doing, the Web can be a perfectly sane place to make a fortune. 1999 was a different story.

As a freshman in college, a San Francisco start-up called approached me about editing a content site franchise for my college campus. The idea was strong, and the ridiculously inflated advertising revenue was supposedly on its way. With promises of a big monthly salary just down the road I toiled nearly 24/7 for weeks and got in trouble with deans for my marketing tactics only to watch the company fold shortly thereafter.

The lesson? Unless you’re actually a partner in a venture, never do work for free.

5. The Stock Market – Of course, I’m not talking about long-term investing – a truly smart way to earn returns and plan for the future. No, there was a time when I thought that more active trading would be a route to some quicker dollars.

The lesson? So-called “active trading” is one stop short of online poker. Sure, there are some with large bank accounts and nothing better to do all day that make it work. For the rest of us, it’s just a risky waste of time.

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About David Weliver

David Weliver is the founding editor of Money Under 30. He's a cited authority on personal finance and the unique money issues we face during our first two decades as adults. He lives in Maine with his wife and two children.


  1. I had a similar (and similarly embarassing) digression into sales after an (equally similar) stint as an underpaid writer. After kicking around as a freelancer who paid the bills by working retail, I decided that the journalism path was probably not going to pan out, and found that my degree was semi-worthless when applying to other jobs. So I decided to hop on the great real estate train of the mid-2000s, and sold houses in 2005. Sadly, the money was *not* there, largely because the field is so fiercely competitive and sales-based that the ones who take the cash are either the ones who are the most established or the ones who are most aggressive, and willing to make lots of cold contacts on a daily basis. Not actually for me; I thought that I’d be able to make money by acting as a trusted advisor and helping impart my knowledge of local communities and housing markets. Instead I went into marketing, where I’ve been much happier since.

  2. I actually had some luck on eBay until the fee structure changed. I could buy moderate sized lots of the product on the bay, break it up into smaller lots (usually singles) and sell each item for $1 – $5 profit. Now with the fee structure the way it is, it is just not worth the time and effort.

  3. Funny, love this article! Although I did know somebody who made a good few extra dollars selling on eBay, but trick is you have to have money to make money. He would make purchases at auctions we’re talking cars, motorcycles, etc and resale them after cleaning them and fixing them up.