2021 Predictions
Did anyone have global pandemic on their bingo board? Ok lets move on…

Last year I decided to do my first ever public predictions for 2020 and the decade ahead. What a fun exercise and wow was I wrong! As mentioned at the top I do not know anyone that predicted the global pandemic of COVID19, despite the writing on the wall and the cases growing in China at the time of this post last year.
So first – how did I do? Here is my made up emoji scoring system for scientific purposes.
π‘ = -1 π = -.75 π
= .5 π = .75 π = 1
1/ Personal security as a service will emerge as a hot topic/app/service people pay for. | π‘ This did not end up happening at all but there are a few startups working in this space which I think have a shot |
2/ NFTs (non-fungible-tokens) will emerge as a killer use case inside an incredibly fun game at a scale. | π Nope! |
3/ A new consulting/freelancing category will emerge. | π Sort of – companies like Wingspan are out there and encouraging progress has been made*. |
4/ Taboos become more normal. | π Companies like Lantern are making this a reality*. |
5/ Alternate use case for a withered technology. Constraints are a virtue β someone will use βoldβ technology to make something βnewβ (see the emergence of Nintendo) β interesting thinking for older tech that introduces constraints that end up being benefits. | π‘ Nope! I had high hopes for this but perhaps the next 9 years. |
6/ The macro economic environment turns. The 13 year bull run ends, and we go into a decline/recession scenario. | π Money printer goes brrrrr |
7/ Microsoft buys Slack. With the stock price off since IPO and the need to βrollupβ enterprise chat + video MSFT takes a swing at solving a huge b2b problem with a startup friendly platform. | π No, but Salesforce bought slack. |
8/ Deep Fakes become a huge problem for the 2020 elections. | π No, but close. |
9/ MR (mixed reality) finds a killer use case. | π‘ Nope. In fact, my prediction on Magic Leap was dead wrong. |
10/ Community is a moat. | π Yes, but it turns out physical spaces lost out this year and virtual spaces and communities won the day (year?). |
Final score = .5
50% is not terrible but I think some of these may come true in the future. I have a long term view and thats how I will justify this years scoring. I also think if I had to predict my outcomes I would have said 25% π
Now onto my predictions for 2021
1/ Twitter builds out payments into the product – launches a new creator chapter. This is more of a hope and a dream, but I think Twitter is well setup to own identity and payments.
Twitter has long been a place of pseudonymity, but also a place of verified identify. They could easily become the worlds largest home of verified payment tags (ostensibly overnight) and give creators with brands, people, and even personalities a place to transact and exchange. The idea of Twitter reincarnating the “verified” program under the launch of a creator economy support system would re-invigorate developers, be an easy way to start to KYC people and integrate with payment gateways (hello Square – they know people over there π
2/ Fractional ownership of a professional team, stadium, or individual player will be possible. This is a play on the existing token infrastructure and NFT thesis I had last year (which did not come true).
Fractional ownership has grown in recent years. Powered by platforms like Otis have ushered in owning a piece of culture by the masses. I think this will extend to a major stadium, player, or team. This may happen sooner in the esports world vs. the professional sports teams in the US. Folks like Russell Okung in the NFL are converting their paycheck into Bitcoin automatically, and paving the way for acceptance from others. I am bullish on this area in general, and genuinely excited to buy a piece of a team.
3/ Bitcoin will break $30k. Bullish in this space since 2015 I see the air cover in place for institutions and private wealth managers to now take the plunge. Since there just isn’t enough to go around, I see the price moving up.
I have been bullish about the crypto asset space for years and I like having some skin in the game on where the price will be (or will at least touch) in the new year. This is a fun area for me as there are founders and companies I am supporting in the space, and its great to see how they have grown during the “crypto winter” of the last few years.
4/ Streaming equity – venture funds + employee stock becomes more liquid. With the advent of programs like CartaX and what I call streaming venture funds, the liquidity in private markets is going to get the foundation to grow significantly in 2021.
5/ The rise of operator angels + micro VCs explodes in 2021. This is already happening, but there will be an explosion of rolling funds, operator angels, and micro investors who want to co-invest in friends, companies, and cohorts they are a part of.
6/ I don’t get the vaccine for COVID19 (but want too!). I think the infrastructure and operational complexity get in the way of massive rollouts for the longtail of 350mm Americans, and I don’t get it until 2022 π¬
7/ SaaS roll-ups and micro-private equity become huge. Funds and people are looking to take a set multiple on SaaS companies and provide liquidity to founders and VCs and run the underlying companies for profit with their own infrastructure. This has been done in the past but I think its set to boom in 2021.
8/ A proper accelerator is setup for GPs. Operating as a sort of fund-of-funds model there is an economy of scale program for figuring out the GP/LP structure, working out the services providers like legal, audit, and tax handling. There is also a network effect of portfolio companies with early GPs. Bonus: Maybe I do this π
9/ Hubs vs. Offices. Deep work continues at home, while “culture days” become norm. Startups pave the way for in person only monthly, quarterly, or bi-annually and large corps have 2 day a week in offices. Many switch to the hotel or hot-desk model.
10/ The try before you buy job economy booms. Startups are more likely to pay mercenaries with expertise (like me!) cash + stock vs. FTEs. The calculus is that if the stock is going to be worth a fortune, they are better off paying for expertise early vs. take a risk on early full time employees risking option pool, culture fit, and ramp time.
I almost bailed on 6 predictions this year and glad I didn’t. Its fun to try to predict the future because you can be so wildly wrong – just like I was in 2020. Now onwards to 2021!
Tags: predictions 2021