Episode summary
What’s the Best Time to Invest?
Ask The Compound
· · Hosts: Ben Carlson, Duncan Hill · Guests: Joey Fishman
Summary
The episode argues that the “best time” to invest is often during a weak or ugly market, especially for people who are dollar-cost averaging rather than sitting on a lump sum. Ben Carlson says a lost decade can actually improve long-run outcomes for net savers because lower prices create better entry points, while it is mainly dangerous for investors who are already fully invested. The discussion also revisits whether another lost decade is possible and ties the answer to recessions, policy mistakes, and financial crises.
Joey Fishman joins to break down incentive stock options, stressing that the tax rules, vesting windows, and liquidity constraints make the topic more complicated than it looks. He says the employee in the question should not assume borrowing is wise just because the shares trade at a discount, and he emphasizes checking the company’s administration platform and tax modeling before acting.
The show also covers an 84-month auto loan at 4.4%, which Ben thinks can make sense in context because of the large down payment and the option to pay it off early. Later, Ben lays out his current view on Bitcoin as a volatile but now more manageable portfolio sleeve, and closes with a practical framework for automating physical health through routine, planning, and boring consistency.
Key takeaways
- Ben Carlson says a lost decade can be a benefit for disciplined savers because volatility creates better entry prices.
- Joey Fishman says ISO decisions are tax- and liquidity-sensitive, so an advisor and platform modeling are essential before exercising.
- Ben Carlson is comfortable with an 84-month car loan here because the borrower put 40% down and can accelerate payments later.
- Ben Carlson says Bitcoin is now about 8% to 9% of his investable assets and he manages it with rebalancing rather than conviction alone.
- Ben Carlson argues health is harder to automate than investing, so discipline has to come from routines, planning, and repetition.
Notable quotes
“if you're young and have the stomach for it, dollar cost averaging into the market, you know, like most normal people do, a lost decade is not something to fear”
“A lost decade should only be scary to investors who are fully invested, right”
“this 84month auto loan actually makes a ton of sense to me because it's a lower payment. It gives them flexibility”
“crypto is still a higher percentage of my overall net worth than I ever would have expected when I first started investing”
How the episode opens
Welcome back to Ask the Compound. I'm your host, Ben Carlson. What is the best time to invest in the stock market?
Maybe during a bull market, you could buy the dip during a correction. What about a lost decade? I answer this question and more on today's show.
Dunham, let's play the music. Our email here is askshow@gmail.com. And we were talking this morning about how impressive it is that each and every week we get something like I don't know 10 to 12 questions straight from our audience every week.
Questions are always really well thought out and insightful. Um just a very high IQ audience here. Right Duncan?
Yep. On this week's show we answer questions about is it good or bad to start investing during a lost decade if we ever have one of those again. Should you borrow money to buy stock in your own private company?
Does it ever make sense to take out an 84month auto loan? I still can't believe that's a thing. Are retail investors propping the market up every time that it falls?
What are my personal views? Me, Ben Carlson, on Bitcoin as an investment, and what's the best way to automate your health like your wealth? I'm turning into a health uh influencer, I guess.
If you're live in the chat on YouTube or Twitter, hit us up with a question and I will do it live. All right. Today's show is sponsored by our friends at Public.
Public is the investing platform for people who take investing seriously. You can build a multiasset platform of stocks, bonds, options, crypto, and more. Uh you can al also access industryleading yields like 4.1% APY on your cash.
No fees, no minimums. Public also uses AI not just as a feature, but it's just woven into the experience.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- investing during a lost decade
- employee stock options
- asset allocation
- bitcoin allocation
- physical health optimization
Watch the episode
Watch “What’s the Best Time to Invest?” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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