Strategic Investing and Portfolio Management

Random Observation/Comment #693: Managing your finance should be a habit, but not an obsession. Re-evaluate quarterly and not daily.

Why this list?

Use your money as an asset to make more money. Any salary is good for maintaining, but once you reach your 30s and 40s and hopefully become debt free, you will eventually make more than your salary if you manage your investments properly. At the same time, there’s no such thing as free lunch, so don’t forget to invest in yourself and diversify.

NOTE: I am not a portfolio manager or financial advisor. This is not investment advice. I am merely sharing my personal philosophy on investment distribution.

How do I holistically look at my portfolio?

This is NOT an article on financial freedom or how to save money. I am writing this assuming the reader has a large cash position (e.g. hypothetically winning $100k post tax lottery) or has seen gains in certain areas and would like to rebalance their portfolio to diversify their exposure.


Cash needed for recurring bills (usually in your commercial bank account with FDIC insurance) – I personally calculate up to 4 months of run costs to keep as cash in my Checking account. There’s some benefits to a higher yield savings account with tax exemptions, but it’s almost too small of a percent to look at. You’re better off paying for premier status features and buying a high dividend stock than just keeping money in a savings account.


Updated to be more mobile friendly and added a zoom in of the mindmap. Also note that the stock market is currently overvalued and I always set my limit sells.

Long time horizon (5-10 years)
Low risk / low yield (but compound interest impact)

  • High overhead
    • Real Estate (requires setup and effort for flipping) – One can hire out a property management team to provide passive income via Airbnb to offset the mortgage. There are some tax benefits here, but I find it too troublesome to take care of. I rather be a renter and have freedom to choose my next destination than go to the same ski resort every year because I feel guilty I have property there. That being said, if there are still low interest rates and a dip in the next 2-3 years, I will consider an investment property.
    • High Value / Illiquid Assets (e.g. Artwork, cars, watches, guns) – Usually requires some middle-person to advise on value and take fees for changing hands. I’d buy to enjoy it and hopefully maintain value over time. There’s some risk of fakes here, that makes it something to consider. I tend to avoid things that can be physically stolen or damaged, but these are definitely nice superficially or needed to join these communities.
  • Low overhead
    • 401k diversification (Stocks, Index & Mutual Funds) – I’m mostly in growth stocks and Asia. Luckily didn’t reallocate too much off of the initial covid crash.
    • 529 college savings – I had opened this for directly saving towards Evie’s tuition. It’s a small percent, but only slightly attractive for tax purposes. Should have bought more ETH with it instead.
    • Private banking services – You can always pay a portfolio manager, but fees are high. I personally do not do this because I think I make better returns.
    • FX diversification – I do have international accounts that hold CNY and CHF. There’s some upside here in the long run.
    • Prosper – Super low yield, but it’s still there with some robo-investment allocations.
    • CDs and Bonds – I like the taxes on these for a number of reasons, but I haven’t bought anything connected to the government.

Long time horizon (5-10 years)
High risk / High yield

  • Low overhead
    • Cryptocurrency in cold storage – This could be worth a lot or a little. Either way, I don’t really touch it and make sure the hardware doesn’t crap out.

Short time horizon (<6 months)
High risk / high yield

  • High maintenance – I consider anything I spend time staying updating on news and actively placing weekly bets high maintenance.
    • Options and Stock Trading – I spend a lot of time watching analysts provide short term strategies off of technical analysis. I consider this gambling, but I do enjoy looking at companies and latest tech. They will also provide some compelling cases for red flags and blow-off tops. Since I see this as gambling, I do not manage more than a $100k portfolio here and never YOLO without covering.
    • Private Markets – If you’re an accredited investor, you can evaluate exposure to some interesting deals for 15-20% return assets. Platforms like YieldStreet provide access to Illiquid assets. There’s usually a one year vesting period, depending on the type of investment.
    • Crypto Markets – I spend a lot of time reading about the space because I’m it’s a part of my job, but I rarely trade ALTs. There’s still massive upside in bull runs with yield farming and I feel like memes and narratives are more powerful than products.

Short time horizon (<6 months)
High risk / usually low yield in $, BUT great connections

  • High maintenance
    • Start up investing through crowdfunding apps like SeedInvest or WeFunder – Honestly, I just like reading up on new company ideas and still follow a lot of software through ProductHunt.
    • Advisory – I haven’t officially been on a board, but I’m open to it. I have advised plenty of companies on the tech side. Upside here is stock options or at the very least a full repayment of invested funds. I’d evaluate this every 6 months. Do this to join the community conversations.

Investment Hypotheses

My current investment hypothesis can be summarized as:

  • Money printer go brrr… – I’m nervous about the infinite money printing on a long term strategy. USD in the FX market is not great. I don’t want to see hyperinflation or deflation, so I keep a minimal cash USD position where possible.
  • Market correction in 2021 – I personally think all stocks are over-valued and pumped by retail options plays. It’s an interesting balance between dollar value and stocks. I’m not a long stocks or bonds investor and always set my limit sells for current exposure. This volatility is great for short term options trading.
    • What are you long? (I’m not buying more positions now though)
    • I’m long Renewables ($TSLA, $NIO, $PLUG, $BEP) because of the EV and battery multi-sell.
    • I’m long Genomics ($ARKG, $CRSP, $BNGO, $PACB) because of ARK.
    • I’d also conservatively always buy the dip for the big tech companies in FAANGM ($FB, $AMZN, $AAPL, $NFLX, $GOOG, $MSFT) especially if anti-trust laws go through and companies split into AWS and YouTube.
  • Cryptocurrency growth, but not forever – Everything goes through cycles. I think we’re in a bull market sentiment even with a pull back (hopefully to 30k or so and breaking the 40k resistance for continued bull market sentiment). I don’t see a reverse sentiment until Sept/Oct based on fundamentals. I treat it like retirement funds so I only move to cash what I would pay as a personal salary to hopefully not get destroyed on taxes.
    • Do you advise anyone to start buying now? It’s a great diversification asset class that hedges against the traditional finance markets, so I’m bullish. It also takes time to get verified on exchanges like Gemini and Coinbase due to KYC, so at least get started to have the option.
  • Always Invest in Yourself and Prune what you Ingest – We have full control of our digital circle as well as our social one. Make sure you’re consuming content that’s thoughtful and engaging with people. Most people join MBAs for the connections. Join some of these conversations for insight and learning directly from the source. People are surprisingly approachable.

Things I really pay attention to:

  • Regulations on Crypto – Regulations killed Crypto adoption in 2018. So far only seeing good things coming from OCC and SEC. I am still bullish based on institutional investments.
  • Sentiment and $SPY breakout patterns for a blow-off top – There’s some leading indicators showing the replication of the dot com bubble crash. I will be concerned if everyone becomes bullish. Maybe off of vaccination news or sooner with change in political power – the markets will eventually reflect the economic situation.
  • Macro world events – I’ve been studying a lot of economic emerging patterns for adoption for fun. It’s all fascinating and makes me feel more in touch with true impact.
  • Industry diversification – Industries and assets are correlated. You can very easily see a large upside swing if you also bought blockchain-based stocks during the wave, but you’d be unevenly leveraged. I’ve personally had a very tech heavy portfolio because I know the companies, but I’m hoping to at least even out with pharmaceuticals.
  • Personal Time Management – Your time is more important of an investment than anything else. Unsubscribe to noise. Keep track of which communities you care about and what role you want to play. Upcoming post on this next week.


I changed my long term strategy around March 2020 when the lockdown first started. It was a readjustment for the next year or so of movement. To be one step ahead, I am considering the first stock market bubble pop, then crypto bubble pop, then dollar diversification.

My personal balance in my investments are:

  • 75% long term strategic – It may be less liquid and I mostly keep it for savings with tax benefits.
  • 25% short term diversification – I may get lucky with some calls/puts or ALT coin bets, but it’s something to keep me busy. I try not to obsess too much over it because it’s very easy to waste a day just reading and processing without taking action.

I would first take money out of my short term bets in terms of retail exchanges and crypto exchanges to pay for personal spending and taxes before touching anything that’s already a long term capital gains tax. Interestingly, Crypto is First in First Out (FIFO) tax calc so after a few years, it can all be a long term capital gains tax.

A more mature investor (especially institutional) would leverage debt a lot more and accrue more physical assets. I do not consider myself sophisticated enough to borrow money on margin for investing (even though I know it’s the way millionaires are 10x-ing and taking advantage of low interest rates).

I’m personally happy being financially free and at peace with a solid strategy than losing sleep over risky exposures. Pay careful attention this year because it will only get more volatile.

~See Lemons Diversified