First-Ever Investor Meeting: 4 Takeaways from a New Startup Employee

I’d rather be a fly on the wall then not be on that wall at all.

Working in the startup world, I’ve always heard so much about investor meetings (whether that might be with prospective investors or those who have already invested in your company). Investor relations is something I’ve wanted to learn more about for a long time. But unfortunately, I’ve never had the opportunity.

Until now!

Last week, I was lucky enough to have a seat at the table with one of Gilded’s leading investors Kelly LeValley Hunt – who is an investor at Pearl River Venture Capital and a sales mastermind. She came to New Orleans from New York to meet with our team for 2 days and dive deep into all aspects of our business, but most importantly our sales process. 

Heading into the meetings, I wasn’t really sure what to expect but knew I didn’t want to miss out. It far surpassed my expectations. If nothing else, it was an incredible experience to bond with the Gilded team for a couple of days and hear what everyone’s working on. On top of that, I learned more about what every individual employee at Gilded does on a day-to-day basis than I ever have. It was a great reminder that sometimes you need to take a step back and work on your business instead of in your business.

I think Kelly set a perfect precedent for how an active investor should use their expertise to push a company forward.

As someone who is still new to the company and not as “in-the-weeds” as the rest of the team, it gave me a unique perspective on the meetings. It felt like we were meeting with a shark from Shark Tank for 2 days in a row, having our business be poked and prodded from all angles.

Think of this article from the perspective of a fly on the wall (which is essentially what I was during these meetings). I won’t get into the nitty gritty details for privacy reasons but I will try my best to distill my 4 biggest takeaways. 

1. Cultivate a beginner’s mindset

Credit to Isaac Quesada on Unsplash

“You’re new. That’s your biggest challenge. It takes 6 months for a full-time employee to get the swing of things and fully understand a business. If you’re part-time, it will probably take even longer. Stay the course and keep learning.”

That’s what Kelly told me on the first day of meetings. She really doesn’t hold back.

For context: on the first day of meetings, ever Gilded team member talked about what they were working on and what their biggest challenges were. This was fascinating for me to hear from everyone on the team since I’ve been remote the past few months.

When it finally got around to me, I told about my story and what I’ve been working on, and then struggled to come up with my biggest challenges. I couldn’t really pin them down exactly. That’s when Kelly interrupted me and said the aforementioned quote.

Cultivating a beginner’s mindset, especially in a disruptive industry like blockchain, is a skill that is overlooked a lot of times. But it’s essential if you really want to become an expert in a field. And in my opinion, it’s way more exciting. I’d rather be the dumbest person in the room in an industry that could change the world than be the smartest person in the room for an industry that I don’t care about at all.

If you want to learn more about how to cultivate a beginner’s mindset from an expert beginner, you should check out “Learn to Unlearn”, a podcast episode from Masters of Scale. In the episodem Reid Hoffman (co-founder of LinkedIn) interviews Barry Diller, the chair and executive of InterActiveCorp and an absolute legend (he’s the mastermind behind the launch of Fox and subsequently The Simpsons and Married… with Children.).

“I always think nobody knows anything about anything, including me.”

Barry Diller

Actionable advice: No matter how old you are, you should read more, consume more, take more notes, and dive down the rabbit hole of your industry so you can fully understand the space that you’re working in. This is how you can truly become dangerous in any field. And it proves to yourself (and potential employers) that you’re adaptable.

2. Become a Thought Leader

We were told over and over again that we need to become the thought leaders in our space of crypto accounting. Kelly really drove home that we are already subject matter experts, so we should show that to the world.

It reiterated my belief that you should learn and write publicly. For people who are experts in a field, it’s important to show the world that you are an expert and that you’re a human behind the keyboard. For beginners like me, you should be putting yourself out there and learning publicly. You should be putting in the reps so that you can become that subject matter expert one day.

Actionable advice: don’t be afraid to put yourself out there and position yourself as a thought leader. You’re probably an expert in something and don’t even realize it.

3. Ask Qualifying Questions

Emily Morter on Unsplash

From the sales perspective (and also a life perspective), I learned that you need to ask qualifying questions when presenting to prospects. It’s something I learned in my college sales class, at my sales job at Launch Pad, and even as a journalist, but it was a good reminder to spend more time asking questions and listening rather than talking.

No one wants to be spoken to for 30 minutes without having a chance to talk about themselves and their problems. The most important aspect of sales is to figure out what is hurting the person the most and really learn how you can best help that person or company with their problems. If you ask the right questions, you will learn whether this person is a fit for your solution or if they are not. But you will never know unless you ask.

Actionable advice: be more interested in the other person and their problems rather than being interested in yourself and your problems.

4. Tell stories to get your point across

Kelly was a master storyteller. When she was giving us advice, she almost always started off with a personal story to give context and credibility to what she was saying. This is something I noticed, and I think it’s a very admirable trait for anyone to have. Well, I guess I wouldn’t be writing this if I didn’t think that.

Along with asking qualifying questions, you need to be able to tell interesting and compelling stories that resonate with people, help build your case, and most importantly entertain, inspire, and/or educate your audience.

Actionable advice: tell interesting stories so you don’t bore your audience to death.


I’m truly thankful to Kelly and Gilded for allowing me to have a seat at the table for these meetings. To summarize what I learned from my first investor meeting, you should (1) cultivate a beginner’s mindset, (2) become a thought leader in your industry, (3) ask qualifying questions, and (4) tell stories to get your point across.

If you’ve met with investors before, what have your experiences been like? I’d love to hear about them in the comments or at my email

Cheers to having a beginner’s mindset and continuous learning,


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Published by Jonah Baer

Florida State student | Memphis, TN native

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