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Lesson one: Just ask the damn question.

I meet a lot of entrepreneurs creating their very first venture.

Lesson one: Just ask the damn question.


I meet a lot of entrepreneurs creating their very first venture. My job is to listen to them, to understand their business and, ultimately, connect them with the right people who can help them succeed.

During the conversation, I get to see their eyes light up when they talk about how they came up with the idea, where the product roadmap is going to take them and how they’ll become profitable (okay, that last point rarely comes up). But almost every single person makes the same mistake as they come in for the home stretch of the conversation. They never ask for what they need the most.

Let me give you an example of what happened while I was pitching my last company. Not only did this investor like what we were working on but he had even expressed interest at one point in investing in our first round:

Sheepish First-Timer: Thanks so much for your time! I’m so excited to continue the conversation with you and to show you how we’re growing. Do you mind if I keep in touch and share updates and ask for feedback and invite you to try new features and come by to say hi and friend you on Facebook and connect with you on AngelList?
Potential Investor: Jesse, sure thing. This all sounds really great and it looks like you’re heading in the right direction. Feel free to send me updates along the way and let me know how I can help.

Besides the run-on sentence, do you see what I did there? Or worse yet, what I didn’t do? I asked him for everything under the sun except but left out the scariest and most important part — asking him for the investment.

I was scared to hear a “No”. I know, as a budding entrepreneur, it’s scary to get a “No” but it’s a necessary evil while building a business. If you don’t ask the burning question, the odds are pretty good it won’t get answered. And you won’t get what you need.

Lucky for me, on my way out the door, I thought that this investment was a lost cause. I turned around and said:

Sheepish First-Timer: I get that you don’t want to invest but would you mind telling me what you’d need to do the deal?
Potential Investor: You could ask.
Sheepish First-Timer: Ummm, uhhhh, ermmm, would you like to invest in our company?
Investor: Sure. Would it be okay if I did $50k?

I hear this story over and over while people are trying to raise capital, make their first hire or close their first partnership deal. If there’s one thing you do at the end of every conversation it should be that you ask the burning, most important question on your mind.