Made a few not sure they are classed as speculative/investment -
1. My wife and I had pretty good jobs when we first married - I had a ProShop business and she had a cosy nursing job.
Decided we wanted a change and decided to sell up, move to the Peninsula, start a B&B/Golf teaching resort.
Found a suitable property which needed to be developed to the state we needed to run the "dream", bought that (before selling the PPoR) and hocked ourselves up to "poosie's bow" and away we went - still kept the jobs up in town.
Renoed the property for about a year, got the driving range up to speed, then pulled the pin on the respective employment and started.
Two odd years later we found we were making no money for a lot of effort at the B&B/golf resort, still had to work full time and were having nervous breakdowns...sold the property to "get out" but managed to double our money in the process! Good investment in hindsight.
2. Bought 2 x IP's in Kalgoorlie in 2003. We sold one a couple of years ago due to financial probs, but both doubled in val during that time, and were pos geared from day 1. Good accidental investment.
3. Moved whole family to USA for 3 years so my wife could fulfil dream of O/S nursing work. I didn't work at all (Mr.Mom), and we managed to send some cash back for much-needed debt reduction. Speculation which turned out well.
4. Renoed previous PPoR to sell - pre-reno val was ~$650k (bought for $305k 7 years earlier), spent approx $70k on the reno and sold for $850k. Good accidental investment
4. Used PPoR equity to buy mechanical workshop - cost $420k including stock and equip. Five years later...no idea what the worth is (3/5ths of F/all), but the turnover is almost half first year turnover....a bomb so far.