Hey @shannon.peel - I hope the bottom isn’t TMI. It’s mostly examples to drive a point home.
Most of my entrepreneurial challenges come from: ‘am I doing the most optimal thing to maximize my time?’
Hard work does not equate money, nor success. You have to combine hard work with optimal moves to make a lot of money.
But the hardest thing about business is that it’s not like schoolwork where they give you the answer. Something you’ve thought long and hard about that you thought is the best thing to do – and you go hard on it – might turn out to be a dead end / waste of time and you’ve wasted months. And then you gotta keep trying hard, with 100% effort until you figure it out.
I started driving Lyft to side hustle along with my main job to raise extra funds so I can buy real estate many years ago. Realized it’s a very bad use of my time. Strangers are danger, and I need something that could eventually scale without my time.
Then I started buying single family rentals with money I saved up from my jobs. I did that for ~4 years and then sold my properties because 1) my assumption that cash-flowing rentals = passive income is wrong. And 2) Returns are lower than just buying S&P 500. TLDR rentals didn’t work for me because risk and time is too high for the rewards.
Then I did some MLM stuff because they convinced it wasn’t an MLM.
I love real estate and hate the aspect of an active management with lower returns. So I turned to investing in syndications instead. Same real estate exposure, with more professional teams, and 100% passivity / 0 decision-making. Only “work” is reading their financial reports once every 3mo, if I want.
Then I looked into flipping real estate in the SF Bay Area. But after 1000+ cold calls later and consulting with veterans in the industry, it wasn’t for me: getting a deal flow going is a lot of luck/work. And even if you get a deal, the results seem quite volatile and even veterans that’ve underwrote deals for decades still lose money on deals. In other words, it seems like profits are based mostly on luck and not skill. But I also know a few outliers that do extremely well on almost all deals and come out very profitable over all. But I can only screw up a deal once and I’m completely bankrupt. So this doesn’t work because digging much deeper, I realized the risk is almost infinite for flipping houses.
Then I started selling stuff on Etsy – more specifically digital goods. This was nice because of 1) scale without putting more time in, and 2) it’s very low risk. The problem is, I made so many PDFs after 30-days sprinting this I got carpal tunnel. And the results were too slow for my taste. Though I still profit maybe like $10 every week from this without every touching it lol. So I guess that’s good. At scale: I probably would need to make a thousand more PDFs (across a few years) to earn a passive income of $2-5k/mo. But that’s not so great, because making PDFs is exhausting and I’m greedy so I don’t want to hire out making PDFs. $2-5k/mo passive income is great for some, but for my fortunate position from my W-2, it’s not enough returns. So I wasted a month here. Namely, the problem here is you have to spend a lot of time creating a product before testing it out.
After all of the above, I moved onto Dropshipping. Here you can directly test out a product without creating/inventing it. So you cut a lot of time out in your entrepreneurial process when you do Dropshipping vs. making stuff on Etsy to sell. Donated a ton of money to Facebook before I realized Facebook ads just do not work. And all the people say it works are just trying to make money from me by selling courses to me. That’s how they make their money, not via selling goods via Facebook ads. So I transitioned to Google ads. But the dropshipping supply chain is bad due to extremely high competition + high shipping costs = low margins.
So then instead of dropshipping, I actually started taking inventory risks and buy inventory in bulk to reduce costs. I interviewed a bunch of 3PL companies to see who can store / help ship out these goods in the States and a lot of them would just lose thousands worth in inventory and not claim responsibility. After that mistake, I transitioned to just using Amazon to shipping my stuff out. There’s a lot more things going wrong with this currently, but it’s currently converging to a long-term, profitable solution.
And then for ~5 years, I realized rental real estate isn’t good because the risk comes from low income vs. high expense. So I turned into Airbnb Arbitrage, where you’d rent out a place and sublet it back out on Airbnb for a profit. This yielded a much higher return and everything looked great. But the risk is also very high because after someone installed a hidden camera in a bedroom, and the same (or different) tenant complained about it, we got banned from Airbnb and bled out money to the tune of $1000/day. OK, so this didn’t work either.
Because my e-commerce business is currently slow, I decided to write a bot that can arbitrage crypto. The return of $ for my efforts + risk far exceeds everything above. By an extraordinarily large factor. Turns out my engineering skills are actually useful to write a money printer, and it turns out after 7 years of entrepreneurial exploration, this crypto opportunity + my skillset = the most optimal use of my time. I spent probably 2+ years on all the opportunities above to lose money / not turn a profit. I spent a month writing code and I wrote a money printer that’s quite profitable. It goes to show it’s not just ‘hard work’ that makes success. It’s ‘hard work + work that fits your skillset + choosing the right work to do’ that yields success.
The extremely condensed version of my entrepreneurial journey above to drive this point home:
Except for the MLM one, I’m not sure how I could have reasoned out that those were dead-ends without trying them out. Unless I’m just really, really dumb (which is probably true). As an example: there’s a lot of false information out there and things that work for others won’t work for you. In real estate rentals – I know a lot of folks that do well with them via meeting investors through Meetups. But I didn’t do as well, nor do I want to continue taking that risk. So it didn’t fit me.
So the most difficult thing is really self-awareness. What skills can you do / willing to learn? What risks are you willing to take, and for what amount of return? Everyone’s situation is different. Some are happy at $5k/mo passive income. Some greedy folks like me would like to have a million a year in passive income. And even how one defines ‘passive income’ is completely different. Nothing’s ever 100% passive.
Having to consider all those factors above, and then coming up with a plan to say ‘I think executing and going with is the best use of my time.’
And often times, it’s not and you lose money and time.
Notice none of the above is me talking about procrastination/mindset/laziness/etc. That’s because for me I really don’t think those are actual hurdles to business. Those are super entry level problems. Like without hard work and hustle, you’re not even in the race to even have a chance to lose in entrepreneurship, let alone win.