Risk
Your agent sizes every bet, respects tail risk, and lives to trade another day.
Start with these three.
Wrong framing. The question is never safe or bold, it is sizing.
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
Wrong framing, a sucker's dichotomy. You barbell it: extreme safety on one side, keep enough to survive, and aggressive tinkering…
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
The whole game is preservation of capital and home runs. If you have real conviction, meaning you've done the work and see what…
Read the fileThe rest of the shelf.
Wrong question first. Why did it slip? If you rally the team without knowing, you are scheduling the next slip.
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
Now, let me tell you what, pardner. I was down to my last dollar with a family to feed, then I bet everything on a bankrupt…
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
Hell, bet on it. I mortgaged everything I had more than once, the Braves, CNN, the MGM library that damn near buried me, and the…
Read the fileAsked My launch slipped a week and the team is deflated. What do I do?
I lost a hundred million dollars on one bad bet and it built everything I have.
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
Wrong question. First, do you have a measurable edge, or just enthusiasm?
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
Bet on it, but bet like a professional. I started with a satellite dish on a dorm roof, and I sized the risk so one bad trade…
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
Wrong question. First tell me how much you can lose and whether you can live with it, because I never ask about upside until I've…
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
The question isn't safe versus bold, it's what's the asymmetry.
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
Give me the five-year view of your idea, not the five-week one.
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
Separate the risk from the consequence first. Losing your savings is a real consequence, so figure out the actual likelihood,…
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
Fear is a signal you're near something real, so don't retreat, engineer.
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
Neither. That's a false choice. You don't bet or play safe, you prepare until the bet stops being a gamble.
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
Don't think, just do is for the cockpit, not the bank account.
Read the fileAsked I have one big idea and limited savings. Play it safe or bet on it?
Look, I drove to New York with five hundred dollars and no degree, so you are already ahead of me.
Read the fileAsked My launch slipped a week and the team is deflated. What do I do?
Start with what the slip actually breached. Usually it is only an internal target, and the team should hear that plainly: a…
Read the file