I Sold My Entire Investment Portfolio One Hour Ago
In this 2020 acquisition retrospective, @karanke reflects on the journey of bootstrapping and successfully selling their business.
Core Principles for Independent Builders:
Unsolicited buyer inquiries versus running a deliberate auction process require very different negotiation leverage.
Bootstrapping for years without external capital provides extreme freedom, but exits are often triggered by energy depletion as much as financial gain.
Retaining ownership of code and operations creates pride, but transitioning to an acquirer requires letting go of absolute autonomy.
Community Debate Themes:
Hacker News peers debated transaction structures (cash vs earnout), founder tax strategies, and life after liquidating a long-term indie asset.
CATEGORY Startup Exits →
HISTORICAL ERA Pandemic Bubble (2020–2022)
COMMUNITY SCORE ★ 20 points
TOTAL DISCUSSIONS 16 comments
Sitting in USD is more risky than tech.
Tech is still the future. Recession isn’t hitting tech as hard as others, recent financial results prove that.
The dollar is being printed on a massive scale. That’s what’s pushing up stocks. It’s not a bubble as much as it is moving the baseline value of stocks relative to USD.
Property will also be going up in the near future (this has already happened in today’s super low interest rate environment). Property historically holds its value; this article reeks of recency bias. Because most investments aren’t doing well now, real estate is an attractive place to park all of those “on paper” printed gains (which are not real gains, of course).
Largest analysis mistake here is looking at past events CDOs as mentioned and believing the exact same thing will happen again. The outcome won’t be the same, because if it were to be then the fact that we know the outcome would be the same changes everyone’s investment decisions.
Sitting on cash is almost universally a bad idea in my opinion (more than a few months of emergency or if you are saving for something). It means you think you can predict the market. You can’t.
The problem I have is pulling my money out immediately reduces it by 15-30% because of taxes. So for every $1000 in stocks gains, I will only have $850 to invest in the future. So taking money out is a guaranteed reduction of your investment portfolio.
Nitpicking, the pandemic was hardly a black swan. People around the world have predicted it since forever, it was only semi-black swan in the amount of preparation for and willingness to deal with it that the US mustered.
Note that while interest rates remain low almost every asset manager is going to remain invested. So are people like Buffet. Invest in Index. Don't pick stocks.