Bad Ideas Do Not Introduce Themselves
Perspective is priceless
Earlier this year, I set out to write a book about the frustrations and failures of startup founders. The idea felt like a no-brainer — juicy failure stories, lessons learned, cautionary tales. I even added the book to my website, convinced it would be a hit.
Nope.
It flopped before it started. But this was not my first misjudgment. As a founder, I chased plenty of ideas that turned into dead ends. My board and employees often reminded me of that.
Not that they had better ideas.
Andrew Blows a Billion
Alongside writing, I do technical due diligence (TDD) for investors, evaluating startups and their technology. I have seen my fair share of red flags. But one project stands out.
An investor hired me to assess a cybersecurity company they were considering acquiring — for billions. Everything looked solid. The tech demos were impressive. The documentation checked out. I was ready to give it a thumbs up.
Then I stumbled on a Reddit post outlining a major flaw in the product. That one post shifted my perspective. I started digging — and quickly found shoddy architecture, insecure configs, and overhyped features. The entire pitch fell apart.
That Reddit post killed a billion-dollar deal.
You Are No Woodward
Afterward, I realized that problems do not like being found. They hide in plain sight until someone honest and uninvested points them out.
Back to my book: the interviews were flopping. Founders clammed up. Then one of them gave it to me straight:
“I’d love to tell you stories, but you can’t publish them. I’d lose my job. And no offense, but you’re not exactly Bob Woodward.”
Oof.
Suddenly, I saw it clearly. I was not just writing a book — I was asking people to risk their careers for my content. Even stories of redemption carry risk. No founder wants their dirty laundry aired, even if the ending is uplifting. Investors bail. Customers vanish. People gossip.
I had been so focused on the idea that I ignored its impact.
Get Perspective
I often advise founders to get outside feedback. Leave your bubble. Stop talking only to your team or board. Talk to people who have zero stake in your success. They are more likely tell you the truth.
When I was building my startup, I was fortunate to have people in my corner who were brutally honest. I heard “that’s a terrible idea, Andrew” more times than I can count.
But, it made me better. It also made me want to be better.
Stress Test Everything
Good ideas, like good people, products, or companies, can withstand scrutiny. Bad ones hide from it. They do not wave red flags. You must aggressively seek out problems.
And truth can come from anywhere. A Reddit comment. A passing remark. A minor incident.
Kind of like how Woodward and Bernstein unraveled the entire Nixon presidency after poking at around a seemingly minor burglary.
Never take things at face value. Question everything: the motives, the numbers, the logic. If something falls apart under pressure, it was never solid to begin with.
This includes your own ideas. Especially your own ideas.
If something feels right, stress test it. Tear it apart. Find the flaws. That is how good ideas get even better. That is how you get better.
As for my book? I have a new idea, that is good. I think.
