What a time to be alive. I asked a machine to provide me with a template to reflect on the year, and now, I’ll do just that.
Personal Reflections: Our family grew to four with the addition of our son, Brayden. Our daughter Michaela is now three and a half years old, and the “time flies” cliche becomes emblazed in my skull a little more each day. I became an uncle, we moved to a new town, and the silver lining with Covid-19 became apparent: I could spend more time with my family and experience a work-life balance I never experienced before. And speaking of family, I was able to make another small dent in the universe by rededicating my childhood school, and renaming it in honor of my grandparents who were Holocaust survivors.
Professional Highlights: I achieved some of my financial childhood dreams with the sale of two of my companies, TULA and Troops, to incredibly iconic companies with Proctor & Gamble and Salesforce (and Slack). But the best part? The people that helped me build those businesses also had life-changing events. There is something incredibly rewarding about building a platform that lets other people do their best work, and seeing it come to fruition is one of the greatest gifts there is. This is one of the reasons I’m so drawn to entprenuership. And if that wasn’t enough, I went on a wild goose chase trying to free some crypto coins from a hard wallet, backed a bunch of amazing founders, and doubled down on beauty with another business I’m excited about called DIBS Beauty.
Challenges and things that keep me up at night: One of my grandfather’s best friends past away. He too was a Holocaust survivor, having survived Auschwitz. I used to think, “one day they won’t be here, and they won’t be able to tell their story.” That day is here. And as their voices diminish, the drum beat of anti-Semitism gets louder and louder with incidents and hate crimes being at an all-time high. Against this backdrop, we have a recession, a population with insufficient education and understanding of history, an economic environment that provides incredibly ripe conditions for scapegoating, and people with pulpits willing to use these conditions to their benefit at the expense of humanity, decency and democracy. We’ve seen this movie before. I’ve been warned about this movie before. Only now, I wonder to what degree my kids will experience this movie.
Looking ahead: I mix these things and more together and I’m still the most optimistic I’ve ever been. We have rockets launching into space and landing on floating barges, artificial intelligence driving cars for us and creating generative images on the fly, gene editing being commercialized, energy being created using nuclear fusion, and the list goes on. I believe that our political institutions will continue to erode, but I’m also confident that founders and innovation will outpace our self inflicted wounds. As one example, while politicians debate things like climate change for political theater, entrepreneurs will develop products and services that people will love (e.g. Tesla) and also produce benefits needed to combat climate change. In short, the spirit of American entrepreneurship will continue to win out.
Conclusion: Despite the hardships and global conflicts that exist, and yes, there are a lot, it’s never been a better time to bet on yourself and try to be a change agent for good. It’s easy to get hung up with the million and one broken things going on, but we each have an opportunity to make a difference in our own lives and the lives of others. The question we should all ask is, how do we do that? And with the year coming to a close, what will our New Years’ resolution be?
For me, I’ll continue to invest in myself, invest in my family, and be a change agent for good. Seems like an appropriate and simple list.
The recent controversy surrounding Twitter’s decision to permanently ban several high-profile accounts has sparked a renewed debate about free speech and the role of social media companies in upholding it. This issue is complex and multifaceted, with no easy answers.
On one hand, companies like Twitter are expected to act as guardians of free speech and uphold the principle of free expression. In this view, Twitter should be a “global town hall” where all voices can be heard and where people can engage in meaningful dialogue with one another. However, as companies operating in the private sector, they are also entitled to their own moderation policies and the right to decide who can participate in their community.
One way to think about this issue is to consider a local bar and restaurant. Everyone is welcome to come in, eat, drink, and talk among themselves. But what if someone stands up at the bar and starts yelling at other patrons? They might start screaming about how Fauci is a crook, how Jews are Satan, or how inflation is ruining our country. People start to yell back, dinner is ruined for some, and a fight might break out. As the bar owner, you have the right to free speech too. You also have the right to decide who can participate in your community and whether or not someone’s behavior is acceptable.
The challenge we face with social media companies is that they are more powerful than most countries. When the people who use these platforms, like scientists, journalists, or even presidents, cause a ruckus and spark a debate, and then get banned, the implications and consequences can be dramatic. We are seeing this play out in real-time and how these decisions impact the most important issues of our time.
Furthermore, our elected officials are often unable to keep up with the times and technology. This leaves us with a group of people, just like us, trying to do their best and make difficult decisions. However, these people also have their own biases and ideas of what is right and wrong.
Ultimately, the debate about free speech on social media is likely to continue for some time. While some may believe that these platforms should be bastions of free expression, others may argue that it is more important to protect users from harmful content.
The echo chamber of social media turns nuanced issues into black-and-white issues, and this is one issue, that has a lot of nuance to it.
Qualified Small Business Stock (QSBS) is a critical topic that most founders are unaware of.
Instead of writing my own blog post about what it is and why it is important, I asked ChatGPT:
describe what qualified small business stock and why it is financially beneficial to people that have equity that qualifies as qsbs
And the answer:
Qualified small business stock (QSBS) is a type of investment in the equity of a small business that offers certain tax benefits to the investor. QSBS is generally defined as stock in a domestic C corporation that is acquired at its original issue, directly or through an underwriter, and that satisfies certain requirements regarding the corporation’s active business, gross assets, and length of time the stock is held.
One of the main financial benefits of QSBS is that it allows investors to exclude a portion of the gain from the sale of the stock from their taxable income. For example, if an investor buys QSBS at a cost of $100,000 and sells it later for $200,000, they may be able to exclude up to $100,000 of the gain from their taxable income. This can result in significant savings on taxes and make the investment more financially attractive.
Another potential benefit of QSBS is that it may qualify for a lower capital gains tax rate. Under certain circumstances, the gain from the sale of QSBS may be taxed at a maximum rate of 28% rather than the higher rates that apply to other types of capital gains. This can further reduce the tax burden on the investment and increase the potential return on the investment.
Overall, QSBS can be a financially beneficial investment for people who have equity that qualifies as QSBS, as it offers potential tax savings and may be eligible for a lower capital gains tax rate.
It missed an important point about how much tax exclusion you can benefit from so I followed up with:
What is the total amount of money an investor can exclude from the gain of the sale if the equity is treated as qualified small business stock?
And the answer:
The total amount of gain that an investor can exclude from the sale of qualified small business stock (QSBS) depends on several factors, including the amount of the gain, the length of time the stock was held, and the amount of the exclusion that was previously claimed on the stock.
Generally, an investor can exclude up to 50% of the gain from the sale of QSBS if the stock was held for more than five years. This means that if an investor buys QSBS at a cost of $100,000 and sells it later for $200,000, they may be able to exclude up to $100,000 of the gain from their taxable income.
However, the amount of the exclusion may be limited if the investor has previously claimed an exclusion on the same QSBS. In this case, the exclusion is limited to the greater of 10% of the stock’s adjusted basis (i.e., the cost of the stock plus any improvements made to it) or $10 million. For example, if an investor previously claimed an exclusion of $5 million on the same QSBS and the stock’s adjusted basis is $100,000, the exclusion would be limited to $10,000 (10% of the adjusted basis).
In summary, the amount of gain that can be excluded from the sale of QSBS depends on several factors and can vary depending on the specific circumstances of the investment.
Lastly, I needed an image for this post. So I asked Dall-e-2:
create an expressive oil painting of a dog in a suit, smiling, depicted as an explosion of a money flying all around them
So there are two really important and unrelated points here:
If you are a founder or early-stage employee, you should internalize QSBS and speak with your accountant about it.
It’s worth spending some time with OpenAI and ChatGPT. It’s wild and only took me 5 minutes to create this post.
Yes, I had $2 million dollars locked away on a crypto-hard wallet that I couldn’t access because of a forgotten password.
But let’s start from the beginning…
In 2013 I started to learn everything I could about the world of Bitcoin and cryptocurrency. It was clear that a new “internet of money” was being born.
I started reading, writing, buying, and experimenting with the world of Bitcoin and everything around it. I almost started a company with the premise of letting people more easily buy and sell Bitcoin. I’ll add that one to the woulda, coulda, shouda list.
As we now all know, a few years later the ecosystem started to pick up. More people were getting involved, including some of my friends.
One of those friends had been making a living as a professional poker player. Instead of only trading cards and chips on digital poker tables, he now also started to trade various cryptocurrencies on a number of exchanges.
I was however busy with my day job building startups and didn’t have time anymore to focus on the crypto world. But, I still wanted to get in early on some of the emerging, off-the-beaten-path technologies that most people hadn’t heard about yet.
So in 2018, my friend Jesse and I were chatting and decided we should make a larger, more concentrated bet on an alternative coin. I would transfer him the money and he would buy and hold the coins for us.
And that’s exactly what we did.
On January 18, 2018, I sent my friend 2 BTC, which at the time was about $12,500/BTC. And with my 2 BTC, and his 2 BTC, together, we bought about $50,000 of a different coin called Theta at about $0.21 per token. This seemed a bit crazy at the time since the logical, sensible part of our brains told us we were basically lighting money on fire.
This is what lighting money on fire looks like.
“Someone’s sitting in the shade today because someone planted a tree a long time ago” – Warren Buffet
That was my plan.
To buy and hold, and not look at it for a very long time.
A few weeks go by…
We get a notice from the exchange where we had purchased and been storing our Theta coins. The exchange was about to shut down because the Chinese government was putting them out of business. Apparently, the Chinese government was working to ensure they had much more control over Bitcoin and the ecosystem. If we didn’t pull our coins and tokens out of the exchange by a certain date, we’d lose it all. I guess that’s China for you.
So we had to move the coins. We asked…
“Should we keep them?”
We decided to keep them. HODL!
Jesse bought a Trezor One hardware wallet and moved the coins onto the device for safekeeping. A hardware wallet is sort of like a digital lockbox for cryptocurrency, where the private information is stored within a physical electronic device. It looks a bit like a USB stick. We managed to move our coins mere minutes before the exchange disappeared.
Life went on.
I forgot about the coins and really the rest of my crypto holdings for that matter and just got back to work on my business.
Prices crashed. It was a nuclear winter in crypto land.
My $25k was now probably worth a few pennies on the dollar and at that point in my life, I just didn’t want to deal with the emotional roller coaster of big swings in the crypto markets. I had enough on my mind with work and didn’t want to be distracted and stressed with these insane markets. I wanted to sell off all of my positions and just ignore the crypto world for a bit.
So I asked Jesse to transfer me my coins so I can sell them and be done with it.
“I can’t do that.”
I asked, “What do you mean you can’t do that? Just send them or sell them.”
And then he said something that would set us off on a wild adventure:
“I forgot the password!”
You see, this is remarkable for two reasons. First, Jesse remembers everything. He remembers all of our friend’s license plate numbers from high school. After all, he plays poker for a living playing 8 tables at a time, knowing the odds, and remembers how probably dozens of different players play the game. In fact, one of the first places we heard about Theta was from another poker player!
Secondly, if you guessed the password incorrectly too many times, the device self-destructs. I mean, it doesn’t actually blow up, but the entire contents erase and our coins would be lost forever! The good news however is if you forget the password, you can always restore the device using a recovery seed which is basically a 24-word passphrase. Jesse wrote this down on a piece of paper while originally setting up the Trezor, but it got thrown away by accident along the way.
We were screwed!
At this point, I was almost relieved. After all, the investment basically went to zero and in many ways, it made living with that shitty investment decision a little bit easier to stomach.
I forgot about the coins and went on with my life again.
The nuclear winter in crypto land was over. Prices started to go up again.
Our $50k was back to about half.
Prices went up again….back to $50k.
Now we figured we should really try to get this wallet open.
“Dan, you’re an electrical engineer. You can figure it out!” I should have paid more attention in class because there was no way I would figure this out. And even if I did, I had absolutely no time to even try.
At this point, I had convinced myself I would never see the money again so I ignored it.
Prices went up again!
At this point, we decided to get a bit more active to figure this out. Jesse started googling the earth to find people that could help.
We found engineers that allegedly hacked this wallet before, but they weren’t interested in helping.
We found a few engineers who seemed like they could pull it off but they either flaked, weren’t interested or ran into obstacles quickly. Some of those engineers were even engineering professors from my school.
Finally, we found some guys in Switzerland who claimed they had done this before. They seemed like they could actually pull it off. The problem now was that I needed to meet them in Paris at their secret lab and Europe was shut down due to COVID. For a few weeks, we went back and forth trying to figure out how we could rendezvous in Europe to pass off the wallet but the combination of the shutdown and not being able to physically go to the lab to watch them hack the wallet made the prospects of this working a bit grim.
Group chats with our friends were becoming ridiculous. I told Jesse if we couldn’t find a technical way to free the coins, we’d find a chemical way to free the coins. As in, we’d go away for a weekend and I’d feed him hallucinogens until he remembered the password.
We found another engineer in Portland. He was a part of a famous hacker group back in the day and testified on the Senate floor saying, “Yes, we can take down the internet in 30 minutes.” We had been exchanging emails to see if he could be our guy to figure this out and free the coins.
He bought some hardware and special devices, made a few calls to some friends in the hacking world, and off he went, trying to hack an exact make and model of our Trezor to prove he could do this.
Over the next few weeks, he went to work and would update us on his progress.
I said as soon as he could prove success, I’d book a ticket out the next day to come to meet him in person with the wallet. We also talked about the fact that if he could actually pull this off, he could offer these services to many more people like us that are locked out of their wallets. In addition, we agreed that we’d have to film this hack because one way or the other we would have to tell this story.
It would either be a triumphant story or a miserable and expensive story, but either way, we were going to document the whole thing.
And sure enough, I eventually get an email with something to the effect of…
“I did it!”
The next day, I drove to Jesse’s apartment, picked up the wallet, and booked my flight to Portland to meet the hacker, Joe Grand.
The rest they say is history…
After two days in Portland, spending a few hours in his lab performing the attack on the wallet, he freed the coins!
At the time the wallet was officially hacked and unlocked, the total value of the wallet was about $2.5 million dollars.
At the lowest point, it was about $20k. At the highest, it was just over $3 million.
Joe is now making his services available to anyone that is locked out of their wallets with a new company called offspec.io.
Did we sell the coins? Yes, we sold some.
The rest? We put on another Trezor and locked it away.
And that’s my story about how I had $2mm locked on a crypto wallet.
And you can see the whole thing go down in this video.
Every morning I use a basic journaling routine to start my day.
When I fire up my computer, the first thing I do is open my note-taking tool and copy/paste in my daily template.
That template looks like this:
Today’s Date – November 30th, 2021
The first thing I’m grateful for today. This could be something small like..
I’m grateful for this hot cup of coffee to start my day, or something bigger like..
I’m grateful to be able to celebrate the holidays in-person with my friends and family after a lousy year with Covid-19. It doesn’t matter if it’s big or small. This routine just helps to build the gratitude muscle and grounds myself with positivity and healthy perspective to start the day.
To Do List
What’s the next action I need to do? I update that here
and sometimes, it adds to the to-do list from days before and reminds me that I need to get focused and burn down my to-do list. Sometimes I also realize I had to-dos that weren’t in fact important or just resolved themselves on their own.
Idea Of The Day
Is there any stroke of genius or ridiculous idea I want to write down and revisit later? If so, I’ll jot it down here.
Or maybe it’s some quote I heard or read, that just seems like a great idea to ponder and think about.
Throughout the day, I’ll just log my notes in this section. If I have a call, I’ll add a bullet point like…
Call with Batman to discuss the new Gotham City Building
And then I’ll add notes about that call here
I use Roam Research and templates to make it easy to link and group ideas together over time, but really any note-taking tool should work here. You can see a snapshot of that below. Another new one to look at is called Reflect App.
I’ve found this to be a pretty simple and effective way to start my day.
When people start asking questions like, “what are you doing for New Years?” it brings into focus the fact that the year is almost over.
And then, inevitably, I think…..How did the year go? How do I feel about the year ahead?
Whenever I zoom out and ask those more macro questions…I keep zooming out…I think about my life and my work compared to other parts of life, to other people, and other situations…
I think about the homeless person living on the corner of 30th and park, a few feet away from our NYC office…
I think about my grandfather that had to drive 2 hours each way from southern New Jersey to New York City, seven days a week to sell eggs from his farm…just a few short years after fleeing the Holocaust and war in Europe…
I think about the headlines in the news…people losing their kids to gun violence…
I think about people being silenced and “disappeared” for sharing their thoughts publicly…
I think about the people that thought they’d have a wonderful morning out skiing with friends but don’t ever make it home…
At times it can be hard to see all that we are thankful for and to appreciate all of the good things happening in our lives. This can be especially hard when scrolling through Instagram, Facebook, or Twitter and comparing your life to the few glorious minutes someone spent perfecting their ‘gram’ and public display for the world.
Or it can feel depressing when reading posts on LinkedIn about how people are crushing it with record-breaking numbers, promotions, and everything in between.
We’re all guilty of this and it could lead us to some dark and interesting thought exercises.
I’ve been there. I get it.
But the reality is this…
Whatever you may be going through or feeling, just try to have the perspective that no matter the situation you’re in, things can likely be a lot worse.
The power of this perspective has been one of the most important and impactful mental models for me throughout my life.
On November 11th, 1947, on the heels of World War II, after the fabrics of government and society were torn to shreds in Europe, Winston S Churchill went on to say this:
‘Many forms of Government have been tried, and will be tried in this world of sin and woe. No one pretends that democracy is perfect or all-wise. Indeed it has been said that democracy is the worst form of Government except for all those other forms that have been tried from time to time.…’
Today is election day. As we know, things are far from perfect.
This can be said about most anything.
Our work and Business, our relationships, our finances, our health.
We all want to do better. We all strive for more.
Today, we have the fortunate opportunity to do more for the country that we live in. We are able to make our voices heard, and counted.
We get to vote, and decide who will represent us and help shape our country and the world for a better version of itself.
And in that effort or any effort to grow and improve, there will be pain, there will be stress, there will be disagreements, there will be failure.
Whatever happens today or this week, it’s important to remember that this perfect union called America is far from perfect, and frankly, it will never be. But as long as we keep putting in the work in our own way like voting, by creating new jobs and opportunities, by making our voices heard, by being decent, by being honest, by doing the right thing, and anything else that perpetuates ‘good’ and the values we hope to live by, we should rest assured that things will indeed get better, as tough as they may seem in the moment.
As a comparison, remember that just years ago the world was in a much worse place compared to today.
Political grievances were settled with gun duels
Mothers and fathers were sending their 18 year olds off to the beaches of Normandy
The average life expectancy from 1500s to 1800s was between ages 30 and 40 years old
Poverty, hunger and child labor are at the lowest levels they’ve ever been
Child mortality is the lowest it’s ever been
Homicide rates are the lowest they’ve ever been
More people in the world live in a democracy than ever before
The literacy rate in the world is the highest its ever been
Moore’s law, which describes the empirical regularity that the number of transistors on integrated circuits double every two years, is still tracking since inception in 1971
Access to the internet is increasing
Solar energy is the cheapest its ever been
By mostly all accounts, the world is in a much better place than it has ever been and I take solace in this fact.
But I also recognize that we must continue to play a role to maintain this forward progress.
So today, please take the time to vote and reflect on what more you can do, regardless of the outcome.
Whatever happens, I’m still the most optimistic I’ve ever been about what’s ahead.
Sometimes you experience something in life that’s rocks your core and makes you take stock of the short time we have here.
Today was one of those days.
My wife and I took our almost 8 month old daughter to see a specialist. I say “almost 8” because at month 8, the doctor wouldn’t see her.
Our pediatrician told us that after month 8, it really doesn’t make sense to get your baby checked out for having “flat head syndrome.”
That’s what the check up was for…
We simply wanted to know if our daughter would grow to resemble her parents with decently shaped human heads or that of an alien.
In my case, maybe both!
We asked our pediatrician and he seemed to think it would be fine. After all, he’d seen countless babies over the years and had seen our daughter grow up since her very first day on earth.
He gave her the first check up, her first shots and vaccines, and so on.
He also shared with us a sort of “go with the flow” philosophy on parenting I could get on board with…and a “no TV policy” that was far less exciting.
“Her head is fine” he said.
“She’s perfectly healthy. But if you really want to get her checked out I have a good friend and specialist that you can see.”
A week goes by…
“Dan, our daughter is going to look like an alien!” my wife said.
I replied, “But aliens have big heads because their brains need the space.”
You can guess who won the debate.
So today we went to see the specialist.
“So what brings you here today?” said the specialist, Dr Peter.
“We are concerned our daughter’s head may becoming too deformed and could present some developmental issues. Our pediatrician said it probably wasn’t a big deal but we figured we’d come in anyway especially now that we think her head has gotten a little worse” said my wife.
He took a quick look and her head was fine.
He asked, “Who’s your pediatrician?”
“Dr. Cammerman”, my wife responded.
“O he’s great. He was my kids pediatrician their whole lives. They are teenagers now but they’ve been seeing him forever.”
As a new parent, it felt pretty great to know another doctor shared the same pediatrician as us. We told him how much we liked him and how great he was with our daughter.
“We saw him 3 weeks ago and will be going back soon for another check up.”
He asked, “you’re going to see who?”
“Dr. Cammerman,” I said.
And then another question….
I said, “Yes, the same pediatrician your kids use. The one that sent us here.”
“I don’t know how to tell you this but Dr. Cammerman died two weeks ago in a biking accident.”
“He was riding from his home on the upper west side across Central Park to his office, he slipped on a patch of ice and was hit by a school bus.”
He was only 50 years old with two kids.
But he really had more like hundreds if not thousands of kids over his career.
My daughter was one of them.
And now a good soul and good man is gone. In such a short period of time he imparted wisdom, kindness and care on me and my family.
I wish my daughter would have gotten to know him better.
I’m sure his family wishes for a lot more than that.
I do too.
I can only hope with time they appreciate and cherish the impact he’s made on so many children and families. His kindness and caring will stick with me forever and act as another reminder of how important it is to be kind and be in service of others, wherever and however we can. Life is too short to do otherwise.
He knew that and became a doctor.
He will be missed.
Please do something good today. Make a dent in the world in a positive way.