5x there, 10x to go
12 min read

5x there, 10x to go

5x there, 10x to go

I’m someone who enjoys reading new-year predictions. Some industry-specific examples include: Tech in 2020: Standing on the shoulders of giants from Benedict Evans, What Will Happen in the 2020s from Fred Wilson, 2017 Predictions by Howard Lindzon, Fintech Prediction Palooza from Howard Lindzon, US Fintech Predictions from Charlie Ma, and Fintech in 2020 from Alex Cohen.  I enjoy them because they’re thought-provoking. That’s it– nothing more. I don’t use them to make investment decisions or anything else. They’re food for my brain and fuel my curiosity. And while I rarely write my own, I’m always thinking about the future.

So I thought it would be fun to identify a few themes that I think have a lot of room for growth in the 2020s.


  • Of personal interest
  • Evergreen
  • Big space
  • Has come a long way in the past 1-2 decades
  • Room & demand for significant improvement

Themes that fit

The Buying/Selling of Homes & Cars

These are 2 of the most expensive things you’ll ever buy and sell in your life, and they’re infrequent events. It’s highly unlikely that you’ll have an information edge over the market. So it’s no wonder why there are significant inefficiencies and imperfections in the transaction process. The entire process is filled with an overabundance of fee-seeking sales-people. And they’re backed by marketing budgets intended to encourage impulsiveness instead of educating you.

It’s gotten better…
Image a world where you had to rely 100% on a realtor– someone who you may not know but wears slick clothes, drives a sweet car, and touts how many houses they sold last month. Imagine visiting house after house, in-person, without being able to glance and weed some out first. Well, you don’t need to thanks to Zillow, Redfin, Trulia, Realtor, and all the others. Some locales even have Knock and Opendoor now. And you no longer need to call or go into bank branches to inquire about mortgage rates. You can check out Bankrate or go straight to Quicken Loans or Better.com. For cars, we’ve got Carmax, Carvana, and Vroom. The process of buying and selling homes and cars has gotten a lot better in recent years.

But it’ll get even better
Fees – phew. Real estate transactions are expensive. And that made some sense in the old world but not in one where the transaction process is significantly more efficient. The costs need to come down, and they will. And how about the speed and confidence in both the product you’re getting and the likelihood it’s the right decision based on the uncertainty in your future beyond the next two years? It’s a complicated purchase. And while finding a house has gotten more efficient, the rest of the process still needs to improve– especially in the case of homeowners who need to sell their current house before they can buy a new one (which is the majority of home buyers). When it comes to automobiles– it’s unsettling purchasing a used car which is unfortunate given it’s the most economical way to buy. It shouldn’t feel like a guessing game as to whether you’re buying a lemon or not, or if it’s been in an accident that wasn’t reported to insurance. The process of buying and selling homes and cars will get a lot better in the future.

Identity, Reputation & Ratings

I’ll always consider eBay to be one of the most fascinating and impactful creations of all time (I covered my interest with marketplaces and networks in the post, What eBay, Napster, and Banks have in common). But not just because it allowed buyers and sellers on opposite ends of the country to transact crap like laser pens. I mean, yes, that was awesome. But it never would have scaled without tackling reputation early on with its peer-based rating system. You can’t have a thriving marketplace or network without trust. And that transpires to all applications on the internet, which has significant implications as all devices and people become connected in the future. Identity and reputation are hard. After all, I’m a privacy advocate (not ‘freak,’ but advocate within reason), so at face value, one might think these things are at odds. And they usually are, but they still need to be solved creatively. A world can’t operate without order. The same goes for a marketplace like eBay, your corner store, or anywhere in between.

It’s gotten better…
Yelp, Health Grades, Care.com, Angies List, eBays peer rating system, Amazon user reviews, WireCutter product reviews, and so on, are all rudimentary. But imagine if they didn’t exist. It is way better today than ever before.

But it’ll get even better
While these services help, they’re also easily and often gamed. There’s a reason the inbound sales process of a B2B SaaS product includes an entire team and tech stack geared at scoring intent and identifying legitimacy and identity. Is someone visiting my site? Who might they be? What company might they work for? What can we learn about their IP address? How long has their email address been in service? Can we look up her LinkedIn profile to see her background from her address? Does she seem legit? Is she a decision-maker? Although this is a very specific example, it shows the length at which organizations and people go to ultimately figure out who someone is, or if they are who they say they are, and a little bit about them. It’s ultimately showing the length at which we go to figure out if someone is trustworthy. Take the Facebook marketplace. I love it, especially for selling things like sporting equipment (I sold a mountain bike and snowboard on it, in no time). You can at least try to stalk the person on the other side of the transaction a bit since they’re within the Facebook ecosystem. That can help give you a slight sense of who they are and if you may be able to trust them. But it’s not enough. The internet, entities, and organizations on it and people want to know who is trustworthy and who isn’t. And in the case that both parties give consent, they should be able to identify the true identity of the other party.


This is a huge, vague theme. “Payments” – what’s that mean? Well, a lot, and it deserves its own post. But in short, I’ll limit the discussion to inefficiencies and access of generically sending money, receiving money, and paying. I won’t get into the details of credit or payment types. There are a lot of players involved in a transaction and they all take their cut. I’m not saying they’re not deserving. They all serve a purpose in the current system, so they should get paid. But maybe the current system isn’t the best and most efficient. Perhaps other themes that I’ve identified in this post (like Identity & Reputation) will improve eventually, and that will render some of the components in the current system irrelevant.

It’s gotten better…
Wow, the past 10 years has been incredible. Remember when there wasn’t Shopify, Stripe, Square, Venmo, Zelle, Cash App, or Bitcoin? It wasn’t that long ago. Stripe and Square were both founded in 2009. Sending money to friends or landlords has never been easier. Standing up a small omnichannel business and accepting your first payment has never been faster. Oh– and the networks like Visa and Mastercard. These businesses are incredible. Their scale is unparalleled. Their networks are marvels.

But it’ll get even better
Crossborder remittances are remarkably broken and have a tremendous amount of room (and need) for improvement. They’re often slow and expensive– 2 things that are at odds with the needs of the use case. I’m not bashing Western Union, Moneygram, or Transferwise. It’s better to have them than to go back in time and not have them at all. But things need to get a lot better. Here at home, we couldn’t even distribute stimulus $$$ to everyone who needed it (perhaps the most) in a timely manner. And when you think about the types of things that can help cross-border remittances, you start to realize that the solution(s) are applicable here at home for most payments and transaction types. There’s something magical about cryptocurrencies like bitcoin, especially if it’s possible to create wallets in privacy-conscious ways. It’s super fast and super cheap to transact. I’m not saying ‘crypto’ is the answer. I’m just saying that it’s thought-provoking and seems like you’re getting a glimpse into the future when you learn about it. You start to recognize that there’s room for a 10x improvement from where we are today. But it’s more complex than the tech (regulations, onramps/offramps, governance). The payments ecosystem will undoubtedly continue to improve and could potentially look very different in 20 years.

Distribution of News…. Finding the Facts

Never in my life have I watched the news on TV more than in recent months. The Coronavirus Taskforce media briefings were the ultimate refuge of up-to-date information and the place to go to see some authoritative figures (Dr. Fauci, Dr. Birx, and Dr. Giroir). But holy shit, both Fox and CNN are dumpster fires. We should have access to a single, trustworthy source of news – the facts without opinion and unnecessary commentary. Where do we go for the facts?

It’s gotten better…
We’ve got Twitter. It’s often noisy and filled with shit, but if you keep up with it and stay organized, then it can be a treasure trove compared to other mediums. Fortunately, we’re in the US, and we’re not censored like other places. We have it pretty good. It’s just noisy.

But it’ll get even better
Axios and NPR are pretty good. It has to get better. We need a news station and media outlet that focuses on facts.

Privacy Tooling for the Non-Privacy Conscious

The need to protect our digital information increases as more of our life moves online. Operational Security (and good digital hygiene) are more important today than ever. Unfortunately, it’s nearly impossible to protect your information that others hold (think your healthcare provider, or Facebook, Google, your bank, etc.). But there are things everyone can and should do to help limit the impact of a breach, as well as to decrease the chance of being personally attacked.

It’s gotten better…
Consumer-friendly VPNs, privacy.com, MFA, TOTP, encrypted chat & email apps, etc. It’s to a point where any computer-literate person can cover their basics with little disruption to their daily life, especially thanks to content like this security guide. But most people don’t know that they should.

But it’ll get even better
For every MySudo, there’s 10 TikTok’s. It starts with education and unfortunately, nobody teaches this stuff to any age group. You don’t learn about this stuff in school, and you barely learn about it for most jobs. While some groups want to patronize Apple and Google, it’ll mostly come down to them for helping protect people from themselves and others. I think companies are just scratching the surface on consumer-friendly privacy-protecting tools and that the need for them is exploding.

Financial Education

I personally believe that Personal Finance is the most important topic for people to learn about and be fluent in. I think it’s true for everyone, regardless of their financial situation. But who is responsible for doing the teaching? Schools? The government? Your parents (who are likely uninformed themselves)? Banks/financial services companies? I think that this is the crux of the issue– most of the players in the system are incentivized against promoting financial literacy. Consumer spending (vs. saving) fuels the economy and is actually a sign of a healthy economy. We live in a debt-driven society. We live in a world where we congratulate someone who buys a house (aka borrows hundreds of thousands of $ from a bank) or a fancy car (again, with a loan). If someone buys one with cash then I get it– congratulate the shit out of them. But I’ll never understand congratulating someone for taking out a monster loan. There’s a lot of noise out there and social media often hurts more than it helps. We idolize lavish spenders. DDTG and r/wallstreetbets – they’re heroine.

It’s gotten better…
Perhaps there’s nothing that will help someone save more money in life than perfecting their credit score. We’re lucky to have Credit Karma and Credit Sesame. They’re incredible tools for learning about credit, a largely counter-intuitive system. We’ve got Personal Capital. We’ve got the bogleheads. Hell, we’ve got plenty of people blogging and tweeting with personal finance tips (like mine) with no goal other than to help educate others.

But it’ll get even better
I think Credit Karma and Credit Sesame are just scratching the surface when it comes to education. I think they’ve set an amazing example of how to create an engaging, informational, valuable service that keeps users coming back weekly. But we need it for more than just the credit system. Savings, investing, budgeting, etc. And we need to hook people from a younger age. And we need to drown out the DDTG’s of the world who are competing for their mindshare.

Job Hunting

Finding a new job often sucks for most people. Compound that with finding a job that someone likes and/or is a good fit for, and it’s nearly impossible. And it’s equally hard for most companies on the other side of the transaction. It’s hard finding good, qualified candidates who will fit in well and produce. From searching to screening to interviewing to hiring– it all leaves a lot to be desired.

It’s gotten better…
Glassdoor, LinkedIn, Career Builder, Lever, Angel List… yeah– it’s a lot better than searching individual websites for their career listings or perusing newspaper listings. View-ability and accessibility is there. But everything kind of falls short after that.

But it’ll get even better
IncredibleHealth is a service I heard about that I think is on the right track. The need from both parties (job seeker & hiring company) is there for better tooling. Maybe more than ever in a remote-first world for knowledge workers.

Health Tracking & Insights/Quantified Self

Every month I gather data from a bunch of sources and publish a recap of how I did (sleep, activity, weight, blood pressure, heart rate, etc.). After losing my in-laws to cancer a few years ago, my wife and I committed ourselves to focus on ourselves more, and on self-improvement. Life’s fragile. Caretaking and losing them was an awakening for me. And I learned how much I hate hospitals so it was a kick in the ass to get in shape so I could at least try to avoid the self-induced killers as I age.

It’s gotten better…
I was an early lover of the Jawbone UP (I wrote this review all the way back in 2011). That thing was incredible. Now we’ve got Apple Watch, FitBit, and Garmin. We’ve got Training Peaks, Zones App, Peloton, Eight Sleep, and rings that will eventually do who knows what.

But it’ll get even better
What’s lacking are insights. We’ve got tracking and information, but then it falls short. I want Apple to draft my monthly series automatically for me so I don’t have to think about it. I want to be told why my resting HR was lower in April than May, or if my sleep pattern for March impacted my weight. I want to know why I may have smashed 3 Peloton PRs this month after not being able to get a new one for 45 days. I want insights! I want to be told that it’s time to go to a specialist for some sort of checkup, and why.


Well, filing taxes sucks. So does paying them but that just is what it is.

It’s gotten better…
TurboTax is better than no TurboTax.

But it’ll get even better
The best UX is often no UX. I don’t get all the reasons why 80% of people need to proactively file taxes each year. Doesn’t the IRS have access to all of the information already… from my employer, from my investment and savings companies, etc.?

Gray Area

Web/Mobile Analytics

Anyone who has worked on a digital product knows the importance of web analytics. They also know how difficult they are to instrument, maintain, make proper use of, and trust. And in 2020, you just wouldn’t think that to be the case. This thread started by Tyler Hogge last night asking “Mixpanel vs Amplitude vs Heap vs ______” was actually the catalyst for this entire post.

I originally had this in the previous section but my friend Mike said, “Web Analytics could actually get worse for companies, better for privacy concerned consumers with regulation, VPNs, and ad /analytics blockers on the client-side.” It was a really good point, so now it sites in this Gray area. Analytic capabilities need to get better but there are forces that may prevent that from happening.

By the way, this article is very loosely related but I’m including it because it’s pretty good – The Best Web Analytics Tool on Satchel.

Notable Exclusions

Mental health support

Anyone that has had to deal with a mental health issue (either themselves or with a loved one) knows how fucked the system is. It’s extremely hard to diagnose and treat. It’s just as hard to find good help, from someone who is competent and cares. I wish I could include this in the top section but unfortunately, I don’t think it’s come far enough along to fit the gating criteria of, ‘has come a long way in the past 1-2 decades.’ At least from what I’ve observed.

Death Procedures

This one is also in the notable exclusion section due to being disqualified because of not coming far enough along in recent times. Anyone who has had to deal with the death of a close loved one knows what I’m talking about. In my case, I had to help deal with the death of my wife’s parents due to cancer (6 months apart from each other). Real estate, cars, bills, bank accounts, pets, social media accounts, cell phones, clothing, furniture, funeral planning, communication with friends and family– it ALL needs to be dealt with, and usually relatively quickly. There’s no playbook and everyone’s situation is unique. It’s hard and the entire process could be improved, but nobody thinks about it until they go through it, and it’s an infrequent event.


There’s a lot of chatter about Email on the twitter-verse today, driven by hey.com. Personally, email has never been a problem for me. Maybe I just don’t get as many emails as others. Or perhaps it’s because I’m extremely organized and stay on top of things. I don’t know why, but email seems like a largely solved problem that can’t get 10x better.