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Deep Learning: Get Ahead by Taking Calculated Risks

It's common knowledge that people learn by doing. Aristotle was quoted saying, “for the things we have to learn before we can do them, we learn by doing them.” I have no doubt that doing is the best way to learn. Too many times I did the endless reading, listening, and viewing about a subject without the most critical "doing" component of the learning process.

Business and investing is a lot like sports in this way. Imagine a person who wants to surf doing endless reading about the subject without paddling out into the ocean with a surfboard. Would you call this person a surfer? You can't gain the knowledge or perspective of a surfer just by merely reading about the subject. In business and investing it's the same.

I never gain deep understanding until I actually step forward and start doing. I've found that the 3 "doing" tips below are critical in establishing deep learning and understanding.


Join a group of other people who have the same interest as you. You would be amazed how many special interest groups are out there. I like to first read all the relatively recent posts around questions and answers the group members are engaging in and then, the most important part, say something! Engage in the community by asking questions and answering the questions that you have a position on. Be honest about your primitive understanding. Remember that joining the conversation is the "doing" we are looking for in the deep learning process.

Some sources you could check out to find the niche you are interested in can be found within groups on Linkedin, Facebook, MeetUp, and Messaging Boards (these communities may be harder to find; however, they could possibly be the truly hardcore thought leaders you are looking for).

I personally used this approach when diving into the app startup world. I wanted to find a group of like-minded entrepreneurs looking to build successful apps. I would answer questions on marketing, SEO, and surveys. Then, when I had an app, the community was receptive to give feedback in return.

Put some skin in the game

Some people (myself included) do more effective deep learning when something is on the line. I learned how to manage a stock portfolio this way. I had many college and graduate courses in business and finance. I found that none of those courses had the same impact as investing my own money into stocks. By opening a brokerage account and then doing the research into determining which stocks to select, I forced myself to come up with a thesis around individual stocks and the market as a whole. Then, I put some money on the line and invested into some shares of a small diversified portfolio. The amount of skin in the game is determined by your individual risk tolerance. I find when I don't have enough riding on my research and decision-making, I'm less likely to follow through. To me it's important that there is enough money (or other asset) put on the line that there will be some consequence if I make lazy half-baked decisions. Remember that you are investing in deep learning. If you don't follow through, you are likely to lose something.

Share what you learned

A fun part of doing these deep learning activities is it makes you more interesting to talk to. Share and teach based on your learnings. This is very important because it feeds the deep learning process and helps you to gain the wisdom you are looking to gain.


Shallow understandings of complex concepts are too common. Differentiate yourself by gaining deep understanding that only experience can give.

About me: I’m mostly focused on internet growth, culture, and startups and am the COO at Wafer Inc. When I can find time between being a co-founder and life I enjoy writing, mostly here and occasionally on Linkedin. If you enjoy my writing, subscribe or follow me on LinkedIn to see more in the future.


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