Five hundred LinkedIn likes can still tell you nothing about whether anyone wants what you’re building.
Charlie O’Donnell learned that from the founder side after years in venture capital. His network was supportive and angel investors wrote cheques because they trusted him and his co-founder. Looking back, Charlie says that support gave them confidence the business itself hadn’t yet earned.
The warning signs were there. Product decisions were under-tested, getting to market was harder than expected, and the people least excited by the idea were exactly the people Charlie needed to hear from. The useful feedback usually required going out and asking for it.
That experience now sits behind much of Charlie’s work as founder of Brooklyn Bridge Ventures and his book Founder Unfriendly. He has spent about 20 years around startup investment, and his advice to founders is deliberately uncomfortable at times: if a well-connected adviser believes in the business, why haven’t they invested? If your network loves the idea, why haven’t customers signed up?
In this episode, we get into how to test demand with people who don’t know you, what repeated investor objections can tell you, and how to work out whether you’re pitching the wrong investors. We also look at why the right investor can understand a business that dozens of others reject, and how Charlie is using AI to pressure-test pitches before they reach a real person.
🔗 Find Charlie on LinkedIn
🗞️ Charlie’s newsletter: This is Going to Be BIG
📖 Charlie’s book: Founder Unfriendly
💰 Charlie’s business: Brooklyn Bridge Ventures
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Key takeaways
1️⃣ Easy money can delay the hard questions
Early funding can feel like proof that the business works, especially when the cheques come from people who already know and trust you. Charlie’s angel investors backed him and his co-founder before the product and business model had faced much scrutiny. A tougher fundraising process could have exposed weak assumptions much earlier.
2️⃣ Use your network to test the message
People who know you can tell you whether an email makes sense or where a pitch is confusing. They’re much weaker evidence of whether someone will actually buy, because the relationship can make them more encouraging or more willing to give you a chance. Use your network to improve the message, then test the offer with strangers.
3️⃣ Distribution means nothing without attention
Access to a large audience is useless if that audience never sees your offer. Before spending months chasing a distribution partnership, work out exactly how people will encounter the product through that channel and whether they already pay attention there.
4️⃣ The wrong customer can give you the wrong answer
A no only tells you something useful when it comes from someone who actually has the problem you’re trying to solve and could realistically buy. Test with the wrong people and you can end up rejecting a good idea because the audience was wrong.
5️⃣ Not every investor no means the same thing
An investor rejection only becomes useful when you know why they said no and whether they were a credible fit in the first place. If three to five relevant investors keep rejecting the same assumption, that’s worth investigating. A pile of noes from investors who were never right for the deal tells you far less.
In this episode
00:00 Intro to Charlie O'Donnell
01:17 Sponsor message
02:12 A good idea isn't enough
06:47 When funding comes too easily
09:14 False confidence from your network
18:07 Distribution without attention
20:20 Ask the right customer
24:29 Turn investor noes into data
29:11 AI as a pitch critic
32:36 When AI misses the obvious
34:54 Keep your best contacts live
