Greg Skloot of Crystal: “Assume you are much more clueless than you are”

Deeply understand the financial and economic levers of your company. Understand where the money comes from, where it’s going, where the expenses are, and, in particular, what the impact of hiring a person is. When you hire someone, the idea is that they should provide at least as much value as they cost. You don’t […]

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Deeply understand the financial and economic levers of your company. Understand where the money comes from, where it’s going, where the expenses are, and, in particular, what the impact of hiring a person is. When you hire someone, the idea is that they should provide at least as much value as they cost. You don’t want to be in a situation where you hired too early or spend too much on salaries only not to have the ability to make it up.

As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company” I had the pleasure of interviewing Greg Skloot.

Greg Skloot is President and Co-Founder of Crystal, which helps you understand anyone’s personality and communicate better with DISC. In 2019 he was named Forbes 30 Under 30 with Crystal CEO and Co-Founder Drew D’Agostino in the enterprise technology sector. Greg is a serial entrepreneur, having previously co-founded (acquired to Event Farm) and has led teams across various successful technology companies. Greg is also co-author of Predicting Personality, a book published by Wiley in 2019 about using AI to understand people and win more business.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I’ve always been passionate about entrepreneurship and technology. When I was in high school, I started my first company fixing computers and building websites and continued pursuing entrepreneurship in college as our entrepreneurship club president. Afterward, I started my own business with my college roommate Drew D’Agostino, when we founded an event planning software company called

We raised venture capital money quickly, hired quickly, and then fell flat on our faces about two years later. We learned a ton from that experience and eventually got back to work with our current company Crystal.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Back at, Drew and I ended up in a crazy situation with our investors that eventually led to us being forced out of the company. At that time, we hired an executive coach with the intention that he’d help us navigate this dicey situation.

One of the things he did so well was understand everyone’s behavior in a given situation. He could predict what they would do next without even knowing them. It was unbelievable how spot on he was, and we were always thinking, how in the world does he do that?

In coaching us, he introduced us to this concept called DISC that he used to understand the personalities of the players in the room. He’d use this framework to know where we were going wrong and how other’s motivations and behaviors would influence their own decisions. Even though he couldn’t save us from our previous failure, afterward, his help was so impactful that Drew and I had this running joke of whether we could create a robot version of him. Can we build a piece of software that could give anyone that type of communication guidance and insight so they could avoid falling into the same pitfalls that we did? That’s how Crystal came to be.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

I would say the most challenging situation certainly was our experience at I don’t think I’d be where I am today without that experience, but at the time, it was a challenging period to overcome.

So, how are things going today? How did your grit and resilience lead to your eventual success?

It’s going very well! Looking at our company’s growth over the last few years, I can say we’ve learned a lot and have been continually growing. However, just as a broader point to this question, I think it’s all relative. I’d say we’ve made tremendous progress when compared to our benchmarks. However, compared to everyone else, we still have a lot of work and opportunities ahead of us.

What do you think makes your company stand out? Can you share a story?

Realistically what makes Crystal stand out the most is our product’s uniqueness — everybody is fascinated by our ability to accurately predict personality.

I think there are few software products that you can confidently talk about at a dinner party where you can confidently pique everybody’s interest. It does have this element of magic to it. And I think that we’ve tapped into this idea of people wanting to understand themselves and others better, which is just a fascinating human psychological phenomenon. That has led us to what is now extremely healthy product-led growth that is very different from other SaaS products.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

Early on at a previous company, I was on a call with a customer getting her set up with an event registration form. And as she was typing in the data, I noticed a bug where none of the fields were saving. So she kept adding fields, and I kept watching them go into the abyss. To make sure she didn’t have to do this work over again, I was texting our engineer during the meeting, telling him each field, and having him enter the data directly into our database.

I won’t forget that moment because it was like there was this veneer in front, but behind the scenes, we were running around patching it together with duct tape to make it work — that was pretty ridiculous! Many early founders probably have a similar story, and I guess it just goes to show you the lengths you have to go to make it work.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

I have found that people outside of your company often think that they know what to do with your product when they do not. I’ve gotten lots of advice from people who, even with positive intentions, try to match their experience to mine without knowing the underlying data.

Early on, we tried to listen to anybody who seemed relevant, thinking we’re pretty young and inexperienced. Others who have been through similar situations must know better. However, I found that just because something worked at their company didn’t mean it would work at mine.

From that, I’ve learned a lot more about making sure that I’m matching the type of advice I’m getting to my business model and company’s stage.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  1. Work ethic: There are many times early on in a start-up where you need to go above and beyond simply because you have to iterate quickly, lean more heavily on customers and partners, etc. All of that requires an extra bit of hustle and work ethic.
  2. Management and organization: It’s not enough to just have a good product. If you have poor management and employees don’t know what they’re doing and don’t have a common goal, it won’t work. Focusing on this early on will alleviate so many issues down the line.
  3. People empowerment: This one boggles my mind in that it seems relatively easy to accomplish; however, it is often a missed opportunity in leadership. I think everyone at some level wants to know where they stand, how they’re doing, and how they can improve. Ensuring everyone in the organization feels empowered to accomplish the larger goal and has a sense of common purpose is tremendously important.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

I’d say humor. I have always said that a major goal of mine is to have fun with what I’m doing, and if it’s not fun, I’d rather not be doing it. Now that doesn’t mean every tactical task will be fun, but you’re much less likely to burn out when you’re interjecting an intense discussion with tons of jokes and general good spirits.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

One big one is ramping up too quickly before you know your product or before you know your product-market fit. If you bring on too many people too fast, you’ll back yourself against a wall if things go wrong, forcing you to cut people, which is never fun. Knowing when to put your foot on the gas pedal and when to hold up is a careful balance but one that’s important to get right.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

Especially early on, admin tasks begin to compile as you have more people. It ends up being this thing where there isn’t enough work for it to be someone’s full-time job, but it’s this nagging annoyance that someone needs to deal with. I think a lot of people underestimate that stuff and assume it just kind of works itself out. But the reality is that somebody has to figure out a bunch of these things.

Another thing is making the mistake of hiring a senior person too late or hiring a junior person when you should have hired someone more senior. As long as you’re careful that new hires are still tactical at early stages, it’s usually better to hire someone more senior. And I’ve certainly made that mistake too many times.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading My Company”? Please share a story or an example for each.

  1. Wait longer before you raise money.
    Don’t jump in and raise a ton of money quickly. Instead, spend more time figuring it out. When it’s venture capital, money is like pouring rocket fuel into your company. If you’re still fixing up the car, rocket fuel is going to explode it.
  2. Don’t just hire your friends or people you went to school with.
    Hire more senior people that are better than you. You don’t want to be coaching your functional leaders. At the core, they need to know how to run their function better than you do. Now, you want to make sure you know enough to be dangerous so you can gut check their decisions, but they should still be the expert for their role.
  3. Deeply understand the legal implications of everything you do.
    Read the legal document and have other legal experts read the document to help you understand it in plain English. This burned me and Drew at our previous company, so I’m always very cautious about signing papers.
  4. Deeply understand the financial and economic levers of your company.
    Understand where the money comes from, where it’s going, where the expenses are, and, in particular, what the impact of hiring a person is. When you hire someone, the idea is that they should provide at least as much value as they cost. You don’t want to be in a situation where you hired too early or spend too much on salaries only not to have the ability to make it up.
  5. Assume you are much more clueless than you are.
    Every year I look back and think about the pitfalls in some of my decision-making. If you’re more aware of your weaknesses, you’re less likely to be stupidly confident, more likely to seek advice, and more likely to ask the right questions. So assume you know less than you do and ask yourself if you have the full picture. If you do not, ask how you can dig a bit deeper.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I’d support a movement towards personal improvement and learning. If you spend more time bettering yourself a little bit every day by either reading a book, taking an online course, etc., you’ll set yourself up for success down the road. If you want to get some better results for yourself, better your status in life, or whenever it might be, it comes down to investing in personal growth and learning, particularly in your free time.

How can our readers further follow you online?

You can follow me on Twitter @GregSkloot or on LinkedIn and, of course, at!

This was very inspiring. Thank you so much for the time you spent with this!

Thank you!

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