The Fastest Way to Lose a Deal Isn’t Your Product
Entrepreneur Office Hours - Issue #318
Inside the Office
I was halfway up a hill on my bike when my friend, riding next to me, said, “I need your advice. I had a situation with a startup founder this week that I don’t feel good about.”
This friend works in the innovation function of a multinational equipment manufacturer and is exactly the kind of person founders want to find on the inside of a big company.
He genuinely roots for startups. He loves scrappy teams with sharp ideas. And because he sits at the intersection of innovation, operations, and corporate venture, he knows how hard it is for an early-stage company to translate excitement into a real partnership.
He plays the role of champion. He’ll take extra meetings. He’ll explain the internal maze. He’ll pull together feedback from multiple business units and package it into something usable. In short: he goes out of his way to help a startup succeed inside a system that was not designed for startups.
In this case, he’d been evaluating a company for a paid pilot. He’d gathered input from the teams that would have to adopt the product. Then he did what most internal champions don’t have time to do: he synthesized the feedback and sat down with the founder to walk through it carefully.
And the founder’s reaction quietly shifted everything.
The founder responded with point-by-point rebuttals. Every concern came back with an explanation. Every suggestion got countered. The tone signaled: “Let me tell you why you’re wrong.”
My friend told me, “I could feel myself shutting down in real time.”
He didn’t get angry. He didn’t argue back. He just stopped wanting to be the person pushing this forward internally. And later, when the corporate venture team asked for an update, he stayed professional, but the founder’s defensiveness was now part of the story.
That’s the part founders miss.
Your reaction to feedback becomes feedback about you.
At the early stage, most people are not betting on your product as it exists today. They’re betting on your ability to learn faster than the world changes around you.
Investors call it “coachability.” Operators call it “easy to work with.” Customers call it responsiveness. Potential hires call it leadership maturity. But they’re all scanning for the same signal. They want to know if, when reality pushes back, you get curious… or if you get defensive.
Defensiveness communicates you think speed is having the answer rather than finding the truth, you treat feedback as a threat rather than a gift, and you’re optimizing for being right instead of building trust.
Curiosity communicates the opposite. It signals you’re here to learn, you’re trying to understand the constraints you’re walking into, and you can take input, synthesize it, and turn it into forward progress.
So instead of responding with answers, the most effective founders respond with questions. And not performative questions. Real questions that signal you’re trying to understand. Questions like:
“Say more about why that matters on your side.”
“What would success look like in your world?”
“What’s the risk you’re trying to reduce?”
“If we could solve one thing first, what would make the biggest difference?”
Curiosity versus defensiveness is the difference between a startup with upside or a startup with too much friction. Because feedback — like the kind my friend was giving — isn’t meant to test startups. It’s meant to help them win.
-Jamie
Worth Your Time
This Product Picnic essay makes a simple but important point that strategy often goes wrong long before execution. It goes wrong at the moment the problem is defined.
The essay argues that when teams frame problems too narrowly, or in terms of a preferred solution, they unintentionally limit the range of strategies available to them. What follows can look like focus and decisiveness, but is often just early misguided conviction.
This is especially relevant right now. Building and shipping are faster and more accessible than ever. Clear problem framing remains slow, ambiguous, and hard to shortcut.
If you’re thinking about product direction, strategy, or what to prioritize next, this is a useful lens.
Tools We’re Tinkering With
Editor’s note: All resources suggested in this section are based on our opinions. These aren’t affiliate promotions and we don’t generate commissions.
Today, I’m gonna reveal one of my favorite lead prospecting tools from back in the days when I was constantly trying to hunt down contact info for potential sales leads, investors, and even guests for my podcast.
The tool is RocketReach. There’s a full web interface you may or may not find useful, but the part I always loved was the Chrome extension. It basically adds a little button to LinkedIn that lets you get the email of just about any LinkedIn profile you’re looking at.
I realize other platforms can do something similar. And some of them can cost less (last time I checked, Apollo is a good option). But, for me, RocketReach’s data has always been the best. Specifically, RocketReach has always been great about surfacing personal email addresses. And emailing someone’s personal Gmail is usually a much better way of reaching them than their corporate email.
However, I should mention, RocketReach isn’t great for high volume, non-targeted sales prospecting. There are other email tools better for that. You also might not want to email someone’s personal Gmail if you’re trying to sell an enterprise deal into their company. But RocketReach is great for getting the email address of that one potential investor, one potential entrepreneur, or one potential partner you want to send a personalized email to and be sure they’ll see it.
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