22' recap & 23' outlook

What a crazy year! My reflections this morning on 2022 were too long for a post, so I put them in article format.

Happy New Year, everyone!

My 22’ recap (wins & losses) and 23’ outlook across four categories:

1. Investing
2. Career
3. Personal life
4. Macro environment

(1) Investing

Wins:?

• Brought a new property, added equity to it with a full renovation, & rented out my old condo. This brought my Chicago real estate portfolio to 3 rental properties and 1 full time residence.
• Made 9% equity gains on my Arrived Homes portfolio consisting of 34 properties, as well as a 4.3% yield on those properties. This was an awesome hedge against the stock market collapse and I didn’t have to take out a loan to invest in these properties, which are a mix of medium term rentals and vacation properties all around the US.
• Made my first angel investment in a pre-seed round of a friend/mentor’s startup
• Sold stock of many of my favorite companies like $TSLA and $MSFT where I had huge gains and reallocated those funds to more defensive investments.?Massive profit erosion/losses avoided.
• Sports betting became a new income stream for me, and I ended the year up about 8%, which I consider a huge win if you benchmark those returns vs the S&P500 (-19.4%).
• I consider my brand on LinkedIn to be an investment. I saw my followers increase by over 300% and saw a 10x boost in impressions/engagement. The professional opportunities and networking opportunities that came from LinkedIn were some of the coolest things about 2022 for me.

Losses:

• Took huge losses on some speculative/aggressive investments like $BNKU and $TELL. I thought that banks would be good investments because of their arbitrage opportunity in a rising rate environment (make more $$ on their deposit bases)…but it seems that recession fears and the impact that would have on consumers/default rates/investment activity have trumped the arbitrage gains coming from the spread that banks make on deposits. I also thought that American liquified natural gas (LNG) would pop in light of the supply shortage in Europe. That thesis still seems directionally correct, but I should have diversified my bets in the LNG space instead of going hard in one ultra speculative play like Tellurian which has been decimated.
• Had a tenant break their lease after just 4 months, which has caused me to have to re-list a rental property in the middle of winter and drastically reduce the rent.?
• Wasn't consistent w/ investing in content creation.. If I didn't write down good ideas to share, many times I forgot about them and didn't post on LinkedIn. Didn't start a podcast or anything to monetize content.

23’ Outlook:

• After being a net seller of stocks during 22’, I plan to be a net buyer in 23’. I think we are closer to the bottom than we are to the top. Def will be buying slowly, though...I don't think the pain is done.
• I want to start investing in farmland. Bill Gates is a pretty successful investor, so if he’s doing it, I think we should be too. Acretrader is a company that I’ve found that looks pretty cool, but I’m still doing some diligence before investing. World population is rising, global wealth is rising, and productive farmland availability is declining. That is a recipe for appreciating prices for productive farmland acreage. Stock market & real estate are both negatively impacted during a recession…farmland is not (from most research that I see).?

(2) Career

Wins:?

• Learned more about sales, the tech market/landscape, and startup/VC life in one year than I did my entire career combined leading up to this year.
• Broadened my experience (transitioned from new business sales to managing clients). This increased my exposure to new executive personas, taught me more about how businesses operate in general, and more specifically how they purchase, renew, budget for, deploy/implement, train, and manage software investments.?
• Massively expanded my network and built meaningful relationships?
• Started going back to the office which had big benefits on my productivity, happiness, relationships, and internal professional brand building

Losses:

• Took some early bumps as I adjusted to post-sale life and the complexity/focus required for success
• Failed to execute on a daily framework and turn my business/process into a machine. This probably resulted in me leaving some meat on the bone in my book of business this year, despite having a good year overall.
• Could have been more aggressive in preparing for my next play…with the economic downturn I doubled down on focus for my current role perhaps at the expense of more thorough preparation for my next role.

23’ Outlook:

• Going to get my real estate license so I can more effectively help others buy/invest in real estate
• Operationalize a daily framework to maximize productivity
• Lots of cross-selling as my main revenue generation method into my client base. People aren’t hiring as aggressively, thus not as much organic license expansion, so I need to be proficient at cross-selling new products to hit my number
• Double down on value selling/realization as I do more selling to CFOs than ever before

(3) Personal Life

Wins:

• Planned a wedding
• Traveled a decent amount (favorite vacation was a catamaran cruise through the Exumas in the Bahamas.?
• Got back into reading and cranked out 1 book per month

Losses:

• Failed miserably with my fitness goals. Too many excuses, not enough planning and routine.
• Used busyness as an excuse too often. Lots of goals/initiatives took a backseat to my “busy schedule”.?
• Neglected some important personal relationships that I should have been more proactive about keeping in touch with
• Screen time continued to prove to me that my phone is an addiction. I missed my screen time reduction goal for 22’?

23’ Outlook

• Getting married on March 10th!?
• Implementing a stringent routine to make sure I maximize productivity
• Gotta find a way to physically separate myself from my phone during the day to reduce screen time
• Even more reading
• Back on my Peloton and weight lifting grind. Every day...no excuses. Plan my day around my workout(s), not the other way around.

(4) Macro environment

Wins:

• Companies seem to have adjusted to the new monetary environment the fed has implemented. Cost cutting, efficiency, and (hot take alert!) going back into the office are all wins IMO for businesses that are serious about their longevity.
• Unemployment remains fairly low broadly speaking, despite seemingly daily news about layoffs in tech. The worst recessions are typically when unemployment is high, so I think this bodes well for the country’s ability to absorb the quantitative tightening that will likely continue through 2023.?

Losses:

• Obviously the stock market and crypto market got smoked this year. Really tough year, and so much wealth was destroyed unless you were confident enough to consistently have short positions on/had hedges in place.
• Large-scale layoffs took place in several areas of the economy. Hate to see it…been through it myself…never easy situations to be in or have to put someone in.
• Interest rates made home ownership way more expensive. Yes, we've seen some pricing moderation in the overblown locations, but not to the extent that it cancels out your drastically higher monthly payment on a mortgage.
• Inflation made everything way more expensive. Gas, materials, food, you name it.

23’ Outlook:?

• We saw the valuation bubble burst this year, but next year will be the year that corporate earnings decline significantly. Typically the true economic impact of a rising rate environment lags behind the rate increases, so now that P/E ratios/valuations have rightsized I think the earnings hit will be in the subsequent next few quarters.?Once we see earnings destruction I think the final shoe will drop in the market and it will be the right time to start buying stocks again.
• We will see a financing trend where VC capital consolidates around the “best in breed” companies. David Friedberg brought this up on an All-In Pod episode earlier in the year and I think we see his prediction come true in 2023.?
• M&A will start to pick up. I think we will see a TON of private companies run out of money that will be gobbled up by bigger players, and PE will continue to makes moves on companies with great products that need more operational rigor.?
• Running out of money, bridge rounds, and down rounds will be commonplace for startups/private companies in 23'.