Author Topic: Investing Lessons/"Mistakes" from 2020?  (Read 19663 times)


  • Sr. Member
  • ****
  • Posts: 491
Investing Lessons/"Mistakes" from 2020?
« on: February 14, 2021, 11:10:01 PM »
Wondering if any of you had any investing regrets? I've been in the game for almost 5+ years, and sometimes I'm baffled at how stupid I am and was wondering if anyone had a similar circumstance.

Wanted to start a thread on mistakes so maybe future members can learn from - here's mine.

Investing Regret#1: Digital Turbine APPS

Why? I was looking at this company from 2018. I understood the mechanics of it and had a friend who worked there and told me assets that the market which was the synergies from the acquisition  that they made. When it was trading at effectively 2-3x PE for a business growing 50% a year, it was incredibly stupid.

Why did I miss it? Possibly because I was distracted by my business, as I started one just before the pandemic, and I completely forgot the business existed. So much so that I invested in a basket of friggin Hotels, Cruises, Airlines, Subprime Lenders before transitioning into a long term portfolio.

What did I lose? 21x return.

Investing Regret#2: Wayfair

Why? I was invested already because I saw how much Amazon invested in furniture compared to Wayfair. Wayfair was investing 2x more. - sold because I was acting like a NAV investor than a value investor.

What did I lose? 10x return.

Investing Regret#3: Rubicon Project

Why? I invested when it was priced less than cash per share. I'm in the industry and knew that the business intimately and will turn around. Effectively priced single digit P/E. I sold again because I wanted to invest in a basked of FRIGGIN hotels, airplanes, subprime lenders, etc.

What did I lose? 30x returns


Not sure, I was plain stupid - completely forgot about one of these names and the other two were because I thought downside was not capped, but looking back that was completely due to irrationality. I don't know why I wasn't able to figure out that Wayfair will sell more furnitures during the pandemic, it was a matter of waiting another quarter. Rubicon Project was from 2018 and my cost basis was so low, I'm not sure why I sold either. Other than that I sold (embarrassingly to say) because I salivated over the $0.50 cent hard asset dollars versus $0.25 cent soft discounted cash flow dollars.

What would I do differently:

Get ready for it. It's something that's not said often. I realized working more doesn't equate to more success, especially if it's at the expense of your health. My attention was massively handicapped by my business, as I started it just before the pandemic (impeccable timing right?). I was panicking - hence I was working 60-70 hours a week. Now I work 36 hours on the business, but the other hours is towards working out, taking classes, and overall self-development.

Sometimes the requirement of success for a venture is beyond capital and resources, sometimes it's just a matter of time. A good chunk of my business came from purely waiting and being ready to take on work. Sales cycles are funny that way. My team works at home, don't really have a schedule, and for all intensive purposes paid on the value they bring to their customers. They can travel and work remotely, all I ask is send a postcard. As Uncle Warren said, just because you get X women pregnant, doesn't mean you'll get the baby X months faster.

Hence, if I took better care of myself by working out, eating well, sleeping, as well as not stressing, I would've gotten to these conclusion faster. However since I was more/less a zombie - I put myself in a position to miss some perfect pitches.

I could've gotten away working 40 hours per week and putting the rest into physical well-being and health. Not saying working more hours doesn't have it's benefits, but at the time, I really had no reason to work that much - other than fear.

Although, I did tremendously well investment wise and more importantly business-wise in 2020 and I'm healthy in a world where some are really decimated by the pandemic, hence I'm not kicking myself too much. However, I kind of realized that as an investor, especially a long-term investor, health is quite important. Not everyone can be as amazing as Warren and have a diet full of processed food and sugars and still have god-like focus.

Hence, health is going to be a priority to me going forward. It was before, but it hasn't resonated and I guess I have to thank COVID. You can't be a great investor if you don't live long. Secondly you can't be a great investor if you're mental acuity is impaired because you're a caffeine-fueled, sleep deprived, fear-ridden zombie. That one lesson cost me hundreds of thousands, if not millions of dollars worth of returns.
« Last Edit: February 15, 2021, 03:26:46 PM by valueinvestor »


  • Hero Member
  • *****
  • Posts: 520
Re: Investing Regrets from 2020?
« Reply #1 on: February 15, 2021, 06:03:50 AM »
Do you think there is anything about your process that you would have changed?

In general, I caution against drawing too many strong conclusions about your investment process during this particular market swing because I think it made a lot of people look silly and some of those people wouldn't look silly in an alternative version of events, whereas some of my decisions to hold on might look smart now but could have been disastrous. 

I know I passed on some things in March/April thinking that we were going to be in for some rough times in the economy (and market).

I continue to try and spend less time worrying about the macro environment. It is paralyzing at times and makes everything look like a bad investment because it can always go lower. I have left a lot of money on the table and was unfortunately surrounded by a colleague in my earlier years who was even more cautious than I was already (holding 40% cash for 7+ years, etc.)

I don't know if this matches with your investment style, but I like the analogy Peter Lynch gave about investing and 7 stud poker in his book Good to Great. The information available is always evolving, so if you feel like you know a business well enough to invest and think the odds might be there, I have gotten in the practice of buying small positions with the intention to scale up either when prices become more reasonable for a business I like and understand well, or to scale up when a business I know less well begins to give more concrete signs of success.


  • Lifetime Member
  • Hero Member
  • *****
  • Posts: 859
Re: Investing Regrets from 2020?
« Reply #2 on: February 15, 2021, 06:08:30 AM »
Sold a position in BYDDY bought at $5 because in April 2020 the outlook for EV and their other businesses seemed to be negative.  Partly driven by wanting to raise cash.


  • Hero Member
  • *****
  • Posts: 2302
Re: Investing Regrets from 2020?
« Reply #3 on: February 15, 2021, 06:13:17 AM »
PINS is probably my biggest sin of omission. Early additions to Office as covid started heating up, was my biggest sin of commission.

I was guilty of viewing covid as a shock that would end and something that companies would simply have to bridge through (so I was very focused on things like contractual cash flow and debt structure), rather than thinking of covid as a catalyst for long term secular changes. obviously the degree of those changes is still up for debate, but it wasn't going on in my head in late Feb / early march when i made some stupid and greedy additions to things down only a little bit, which hampered my aggression during the fattest of pitches.

Not buying Pinterest in early April for a very reasonable price ($15 vs $80+ today)

I put it on my to do list and never really dug. Should have prioritized it over other things. At the very least, I think the big picture was compelling enough for a starter position.

6x on a 2-3% starter would have been nice.

I think it was hard for me to venture out of my comfort zone when I was in the trenches of real estate land and only just starting to recover from a 40% drawdown and giant change in fundamentals (and price) of everything i owned.

Sent this to a friend on 4/4
So this type of thing is not really my usual fare, but I have it on my list to get to know Pinterest.

PINS trades for $7.9 billion with $1.7 billion of cash for an EV of $6 billion.

Pinterest has over $1 billion of sales, grew 50% last year, is the country’s thirds largest social network, has MAU = to 14% of Facebook.

Do I get it? Not really, but $6 billion is not a lot of money. What interest me about Pinterest is that I can actually kind of sort of make financial sense of it. Optimistic Bloomberg projections get to a 20% EBITDA margin 4-5 years out. On current revenue that would be $200mm so 30x. At $4 billion of revenue (again optimistic Bloomberg projections), 7.5x.

What is also interesting is I imagine PINS has lots of exposure to travel and small businesses and is about to see its near term business decline significantly.

The confluence of a internet property of high potential strategic value, a net cash balance sheet, a roadmap to actually a reasonable multiple, and terrible near term fundamentals with respect to advertising, lead me to hypothesize this could get super interesting.

« Last Edit: February 15, 2021, 06:22:10 AM by thepupil »


  • Lifetime Member
  • Hero Member
  • *****
  • Posts: 3925
Re: Investing Regrets from 2020?
« Reply #4 on: February 15, 2021, 06:24:49 AM »
Just to throw some things out ....

Know what you want, and keep your eye on the prize. For most people it's family/community, business, other; and in that order. Over a 3-month period, log how many hours you are spending where, and how many hours within each bucket were 'quality time'. There is a reason why so many NA families are dysfunctional.

Passion. Managing the business (CEO) or managing the cheque-book (CFO)?  A key realization, because if you choose CEO; a great many livelihoods are relying on your ongoing acumen - and they deserve your full attention to the task. You may well be good at both, but you can only do one.

Partners. Better decisions, division of labour, shared successes, ability to take vacation; all kinds of net benefits, but you have to be able to share leadership. With lots of other strong minded people, across genders, cultures, and demographics. You have a tribe, even if sometimes you might wonder!

Sustainability. Every business textbook known to man, advocates that bigger is better; but sadly it's only true in the short-term. The reality of course, is that ultimately -  the business just dies faster; yeast in a sugar solution, being the everyday example. There's a sweet spot for every business - know what it is, and whether it is for you.

Most people will come to investing, either from the finance world (CFA, etc), or the business world (MBA, CPA, etc); and often they will be a hybrid of both. Great bones upon which to build something, but you have to make a decision.

Choose well, and you will have both a rich and very long life.





  • Hero Member
  • *****
  • Posts: 1971
Re: Investing Regrets from 2020?
« Reply #5 on: February 15, 2021, 07:06:26 AM »
Honestly, if the 2020 episode worked out like 2008/2009, you would not be having these regrets.  The guys who bought Carvana at the lows might have to suffer massive dilution like the banks did in 2008/2009 because the Fed took their time to rescue the banks back then.  Now you have a bunch of youngers guys running around thinking they are geniuses because they are up 100-300% in 2020.  Ask yourself what does the alternative might have look like?  Also you will always miss some incredible bargains during a selloff.  You are not going to catch all the amazing deals or all the Pokemons.  This is simply a part of life.  In 2008/2009, SL Green had dropped from $150 to under $10 and I walked around all over Manhattan going door to door and looking at SL Green buildings.  I couldn't buy because I did not understand how bankruptcy works and how equity can retain value in a bankruptcy.  That was a 10 bagger that I missed out on.  But back then I probably would have gotten a bigger ego and would have winded up doing something dumb with that money anyway. 

The stuff that I regret is not buying more Ashtead.  Now that's a really good company with a long runway to grow.  It traded as low as 10 British Pounds and is now at 40.  But it will probably be another 5-10 bagger from here given 5-10 years.  That's the one that I regret not buying at the low and not in bigger size.  I regret not buying more Berry Global and DuPont at the low.  Because I know those companies.  They were existing portfolio companies that I knew were going to be 3-4x in 3-4 years.  No balance sheet issues, good cashflow, etc.  But I decided to diversify into a bit of growth.  Frankly, I have done pretty well there as well.  Now my portfolio is more diversified and the stuff that I bought are up 30-200%.  Overall, I am just happy I didn't blow up and I reallocated pretty well.  Clients are happy.  Sure I don't have the 100% return that a few managers reported.  But I also wasn't the one getting angry phone calls in March and April.  The clients are genuinely happy with what I did last year.  Like Jake Taylor from the Value After hours says "I'm not designed for optimization, I am designed for resiliency and survival" or something like that. 

Can't look at what you know today.  Need to remember how you felt in the moment and don't forget that.  The world in March/April was not as clear cut as it is today with vaccines that are 90% effective. 


  • Guest
Re: Investing Regrets from 2020?
« Reply #6 on: February 15, 2021, 08:55:48 AM »
learning from mistakes? si. regrets? non!

"if all you've got to live for, is what you left behind, get yourself a powder charge and seal that silver mine"

Garcia Jerome J / Hunter Robert C


  • Full Member
  • ***
  • Posts: 144
Re: Investing Regrets from 2020?
« Reply #7 on: February 15, 2021, 09:03:10 AM »
Putting on my market timing hat in March and thinking I could just wait until it dropped further. Missed out of Facebook and Uber below my target buy prices.


  • Full Member
  • ***
  • Posts: 206
Re: Investing Regrets from 2020?
« Reply #8 on: February 15, 2021, 09:07:00 AM »
Purchasing my fathers parents  cottage with 5 acres on Georgian Bay Ontario in 1989 for $850K now worth over $10 million plus or more next door to Eatons summer residence and my place of birth Ugh!


  • Sr. Member
  • ****
  • Posts: 491
Re: Investing Regrets from 2020?
« Reply #9 on: February 15, 2021, 10:48:49 AM »
Purchasing my fathers parents  cottage with 5 acres on Georgian Bay Ontario in 1989 for $850K now worth over $10 million plus or more next door to Eatons summer residence and my place of birth Ugh!

How’s this a regret? Sounds great! Georgian Bay is beautiful!  ;D