The Founder Video You're Avoiding Is Probably The One That Would Work Best
The founder video you keep avoiding, about a real failure or an unpopular opinion, is often the one that works best, because safe content blends in and candor stands out. Record it if it passes one filter: you'd be comfortable discussing it calmly with anyone it involves.
There's a video you keep not recording. The failure that cost you real money. The opinion half your industry will hate. The mistake you still haven't fully processed.
You tell yourself it's not the right time. I'd bet it's the video that would work best. That discomfort is usually a signal the content matters, not a reason to skip it.
Before you ask for money, know you're ready.
Your number, your terms, your system to find investors and your answers. One checklist, built by a founder who has been on both sides of the table.
SEND ME THE CHECKLIST →Why does uncomfortable content perform better?
Safe content blends in. Generic advice and polished wins look like everything every other founder in your space already published. Uncomfortable content stands out because most founders won't publish it, which makes the one who does more memorable and more trusted.
Viewers read discomfort as authenticity. A founder visibly working through something real comes across as more credible, not less, even when the video is rougher around the edges.
There's a practical reason too. Your audience is dealing with the same problems you are. A video about the thing you got wrong is often the most useful thing they'll watch all week, because it's the part everyone else leaves out.
What should a founder make videos about?
Start with the list you've been avoiding. Most founders have some version of the same four:
- A costly mistake, with what it cost and what changed after.
- An unpopular opinion about how your industry works.
- A decision you got wrong and how you'd make it today.
- Something you're still figuring out, told as a work in progress.
These are the pieces nobody wants to publish, which is exactly why they work.
How do you keep it honest without being reckless?
There's a real difference between uncomfortable-and-honest and reckless-and-unfiltered. Use one filter: would you be comfortable discussing this, calmly, with anyone it involves, if they watched it?
| Passes the filter | Fails the filter |
|---|---|
| Your own mistake, told with what you learned | A former partner's mistake, told to settle a score |
| Naming a pattern in your industry | Naming and shaming a specific client |
| Numbers from your own business | Private details someone shared in confidence |
If it passes, it can still feel uncomfortable to publish. That's usually where the strongest content lives. If it fails, you don't have a video yet. You have a grudge, and that stays off camera.
Find out what an investor will ask before they ask it.
The Raise Readiness Checklist walks you through everything you need before you ask for money.
GET THE FREE CHECKLIST →The objection: "Won't publishing a failure hurt my credibility?"
If the point of thought leadership is expertise, why advertise a mistake? Because a specific failure, examined plainly and paired with what it taught you, usually builds more credibility than another polished success story. It shows judgment that only comes from being wrong and learning from it.
Structure matters. Lead with the stakes, show the decision, then show what changed. That's the same logic behind the case study format most founders get backwards.
A hypothetical: one video, a year of avoiding it
Picture a founder who avoids recording a video about an expensive early mistake for almost a year, worried it'll look unprofessional. When they finally record it, with real numbers and a real account of what changed, it becomes one of their best-performing pieces. The comments thank them for the candor, and several come from viewers in the middle of making the same mistake right now.
What to do this week
Name the one topic you've been avoiding because it feels too exposed. Run it through the calm-conversation filter. If it passes, record it this week, in one take if you have to. Keep it short: what happened, what it cost, and what you do differently now. The safe content is already crowded. The honest version is the one nobody else will publish.
Key takeaways
- The video you're avoiding is often the one your audience trusts most.
- Filter it: would you discuss it calmly with anyone it involves?
- A failure plus what it taught you builds more credibility than another win.
Frequently asked questions
Should founders talk about their failures on video?
Yes, when the story includes what the failure taught you and what changed afterward. A specific, candid account of a mistake shows hard-won judgment and usually builds more trust than another polished success story.
What video content should a founder make?
Start with the topics you've been avoiding: a costly mistake, an unpopular opinion about your industry, a decision you got wrong, or something you're still figuring out. Those stand out because most founders won't publish them.
How do I share something personal without hurting my business?
Apply one filter: would you be comfortable discussing it calmly with anyone it involves if they watched it? Share your own mistakes and numbers. Leave out other people's private details and anything aimed at settling a score.
Mike Nathan
Founder & CEO, Impero Ventures · Founding Partner, Exit 156 Capital
20+ companies. $170M revenue. $55M raised. 3 exits. 2 VC funds. 1M+ YouTube subscribers.
He doesn't just pitch investors. He founded two venture capital funds.
More about Mike →Got a real business and never raised?
The Raise Academy takes founders from frustrated and floundering to fundable and raising. Four weeks with Mike Nathan. Investor-ready, GUARANTEED.
The guarantee covers getting you investor-ready. No one can guarantee a raise.