Enough is enough. Lemmings no more. The blind quest for cash is a fool’s errand.
True freedom is much more than having enough income and time to do what you want.
If you can free your time and location, your money is automatically worth 3-10 times as much.
The majority of my finances come from early-stage startup investing.
For me, money is not a prime motivator. It’s one criterion that I can use to filter out opportunities. My high is the eureka moment when I find, or I am taught, a non-obvious way of solving a problem.
Where can you trade money for time? Where can you spend money that creates more time tomorrow or next week? That is almost always a good investment.
1 000 000$ in the bank isn’t the fantasy. The fantasy is the lifestyle of complete freedom it supposedly allows.
Being financially rich and having the ability to live like a millionaire are fundamentally two very different things.
Money is multiplied in practical value depending on the number of W’s you control in your life: what do you, when you do it, where you do it, and with whom you do it. I call this the “freedom multiplier”.
I’m not averse to making a lot of money. But where does that end? I hang out with people with hundreds of millions of dollars. Is that the standard by which I should measure myself? Where does that take you if you’re in my business? I think it takes you to pretty dark, corrupt places.
I have plenty of money to do what I want to do, and I have the relationships.
Your network is your net worth.
In the beginning of your career, you spend time to earn money. Once you hit your stride in any capacity, you should spend money to earn time, as the latter is nonrenewable.
If you find yourself saying, “But I’m making so much money” about a job or project, pay attention. “But I’m making so much money,” or “But I’m making good money” is a warning sign that you’re probably not on the right track or, at least, that you shouldn’t stay there for long. Money can always be regenerated. Time and reputation cannot.
“If only I had more money” is the easiest way to postpone the intense self-examination and decision-making necessary to create a life of enjoyment- now and not later. By using money as the scapegoat and work as our all-consuming routine, we are able to conveniently disallow ourselves the time to do otherwise.”
Money doesn’t change you; it reveals who you are when you no longer have to be nice.
The more we associate experience with cash value, the more we think that money is what we need to live. And the more we associate money with life, the more we convince ourselves that we’re too poor to buy our freedom.
The goal of “investing” has always been simple: to allocate resources (e.g. money, time, energy) to improve quality of life.
I am willing to accept a mild and temporary 10% decrease in current quality of life (based on morale in journaling) for a high-probability 10x return, whether the ROI comes in the form of cash, time, energy, or otherwise.
People don’t want to be millionaires — they want to experience what they believe only millions can buy.
An investment that produces a massive financial ROI but makes me a complete nervous mess, or causes insomnia and temper tantrums for a long period of time, is NOT a good investment.
I don’t typically invest in public stocks for this reason, even when I know I’m leaving cash on the table. My stomach can’t take the ups and downs, but—like drivers rubbernecking to look at a wreck—I seem incapable of not looking. I will compulsively check Google News and Google Finance, despite knowing it’s self-sabotage.
A large guaranteed decrease in present quality of life doesn’t justify a large speculative return.
One could argue that I should work on my reactivity instead of avoiding stocks. I’d agree on tempering reactivity, but I’d disagree on fixing weaknesses as a primary investment (or life) strategy.
I get 50-100 pitches per week. This creates an inbox problem. […] I’ve had to declare email bankruptcy twice in the last six months. It’s totally untenable.
From 2008 to 2009, I began to ask myself, “What if I could only subtract to solve problems?” when advising startups. Instead of answering, “What should we do?” I tried first to hone in on answering, “What should we simplify?”
I don’t want to hire staff for vetting, so I’ve concluded I must ignore all new startup pitches and intros.
I’m tired of unwarranted last-minute “hurry up and sign” emergencies and related fire drills. It’s a culture of cortisol.
I’m in startups for the long game. In some capacity, I plan to be doing this 20+ years from now.
Most of my best investments were made during the “Dot-com Depression” of 2008-2009 (e.g. Uber, Shopify, Twitter, etc.), when only the hardcore remained standing on a battlefield littered with startup bodies.
To get rich beyond your wildest dreams in startup investing, it isn’t remotely necessary to bet on a Facebook or Airbnb every year.
