BTU #163 - Army to Season 2 Apprentice Winner (Kelly Perdew)

“These are four people who are brilliant at what they do. I’m very impressed with all of you. To start the evening, Kevin - you’re fired. Sandy - you’re fired. Jennifer - you’re fired. Kelly - you’re hired.”
-Donald Trump

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Kelly Perdew is the Co-Founder and Managing General Partner of Moonshots Capital, which he founded with a fellow West Point grad, and exists to invest in exceptional entrepreneurs with world-changing ideas. He started out at West Point, after which he served in the U.S. Army as an Intelligence Officer. Since then he has worked as a Founder, Board Member, CEO, COO, CFO, as well as in Business Development, and Sales. He has raised institutional financing, grown businesses, down-sized businesses, and sold businesses for 8-figure exits. Perhaps most uniquely, he is the Season 2 Winner of The Apprentice, after which he apprentice to Donald Trump and was involved in multiple real estate projects with Donald Trump. He holds both an MBA and JD from UCLA.

Why Listen: 

Kelly has such a unique background and has had so many different aspects to his civilian career. In this interview we talk about what it is like to be an investor, and advice for Veterans wanting to pursue this path. We also talk about entrepreneurship, and advice to Veterans who want to start their own company. We talk about work life balance, recovering from failure, what those final moments were like on The Apprentice, and so much more.

Our Sponsor: 

  • StoryBox - People trust each other more than advertising. StoryBox provides the tools and supports businesses need to take the best things customers say about them, and use them to drive more sales and referrals. StoryBox offers a 10% discount to companies employing veterans of the US Armed Forces.
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Selected Resources: 

Transcript & Time Stamps:



Kelly Perdew is the co-founder and managing general partner of Moonshots Capital which he founded with a fellow West Point grad. The company exists in order to fund exceptional, world-changing ideas. He started out at West Point and then served in the US Army as an Intelligence Officer. Since then, he has served as a founder, board member, CEO, COO, CFO, as well as working in finance and sales. He has grown businesses, downsized businesses, and sold businesses for eight figure exit points. Perhaps most interestingly, he is the Season 2 winner of The Apprentice. After which he apprenticed and worked on multiple real estate projects for Donald Trump. Kelly holds an MBA and a JD from UCLA.



Joining me today from Los Angeles is Kelly Perdew. Kelly - thanks for being here. What advice do you have for people on active duty regarding what they might be interested in doing after the military?


That’s a great question and I think it’s something a lot of veterans think about. It comes back to trying to tie together what you functionally like to do and what you have capability for. There’s a place for everyone so it’s about finding out what you’re good at and what you like to do. And then a large part of it is information gathering. Leaving the military and heading into the business world is at best daunting and for many people, very scary.


I read a Huffington Post article in which you talked about the traits you learned in the military that have served you most in the business world. You named leadership, discipline, and integrity. Is there a flipside to this? Are there any common weaknesses veterans may possess when leaving the military?


Personally, I think my personality fit well inside the military. Some of the requirements for niceties weren’t always absolutely necessary because you’re more aiming for efficiency of communication and speed. But in the civilian sector, those things mean a lot more. So I had to retrain myself in that. Also timelines as in the time in which you tell people you are going to get things done. There are many groups of people and skills that don’t lend themselves to hitting exact timelines. The creative department, for example, might not think about deadlines in the same way you do. So it's important to think about the message you are delivering and how you’re delivering it.


Do you have any advice for successfully selling yourself?

Whether you realize it or not you had millions of dollars of leadership training spent on you in the military. That doesn't happen anywhere else. Nobody else walks you through how to delegate, give orders, take orders, or structure operations. Business school is more technical and nobody other than the military really focuses on leadership. So that’s something that’s something that’s really valuable. My partner in my current company is also a West Point grad who served 17 years in the military. Our assessment of all of early stage tech companies that we’ve invested in is based around leadership. All things being equal, I’m going to pick the team with a veteran because they’re going to show up on time, move fast, follow directions, solve the problem. For the most part,integrity has been beaten into them. Military members coming into the civilian world should understand this value. And also have the humility to understand that there is still a lot they need to learn on the civilian side.


What type of work does Moonshots Capital do?

There’s a term to describe hot shot, young startups - “unicorn”. Unicorns are invested in by venture capitalists. Venture capitalists take money and put it into a company,  risking that the company will eventually succeed. If company grows in liquidity, they will give the investment back to us. So it’s really about identifying great leadership and then helping those companies grow.


What do you typical day-to-day activities look like?

One of our big work efforts is sourcing deals. The companies that want you to invest in them come and present to you. There’s a process that startups will go through - initially they’ll talk to you and give you a brief overview. If we’re still interested, it goes a little bit more in depth. Then you conduct a customer survey and background check of the company to make sure everything is good there. Then you go back-and-forth and see if you can come to agreement in terms of investing in the company. So in a typical month we’re communicating with up to 200 startups. Usually about 12 we actually have meetings with and a couple more we follow-up with.


I read that a large percentage of your investments are made into company’s with a veteran connection. What advice to you have for veterans that want to start their own company?

Being an entrepreneur sounds sexy but it’s definitely not for everyone. My best advice would be to talk to entrepreneurs and not just those that are super successful but to a broad spectrum of entrepreneurs. And talk to them about their experiences. It really is a life choice. You’re foregoing what a lot of people look at as high security and shared responsibilities in a more established company. Entrepreneurship can be like a lone wolf experience. But you do have more control. That stress and also excitement can be like a narcotic but it can also have a great detriment on your finances and personal relationships.


I read an article in which you talked about a failure with your first company. Do you have any advice for veterans around the idea of failure?

There’s a lot of tension for me surrounding many of these ideas. There’s been so much written about how you need failure and how failure pushes you ahead. But it’s something you really have to think about too. If you’re an entrepreneur and you're hiring people, you’re pretty much responsible for their lives. The loss of a job for a civilian due to your poor leadership as the head of a company can be very challenging. So I don’t downplay at all the importance of leadership to make a company succeed. These companies are battling to succeed. So you have to be a little crazy to be an entrepreneur.

In those early days it’s only you and your co-founders. Everyone enters that phase with a good idea that there could be a bad outcome. So it’s the people with leadership and resilience who outlast the dips and will eventually succeed. Exhibiting those leadership characteristics - that’s what really sets companies apart.


Do you have any advice about work/life balance?

I was living in Los Angeles when I was working on my first company. Many of my clients were on the East Coast so it was a really early morning. I found myself at 2PM not having eaten all day. I had no time to date or spend time with family. So I vowed to myself after that first foray into entrepreneurship that I would do it differently in the future. So now I put the most significant things first - taking care of myself and taking care of my family. And then maintaining some semblance of friends and a social life is extremely important too.


You got your MBA/JD after leaving the military. What advice do you have for someone leaving the military regarding graduate school?

It depends completely on a person’s individual desire. My general blanket feeling is that there should be no more going to law school. It’s such a drain if you think about all that brain power and redirecting it to anything else other than being an attorney. If there’s particular areas you're interested in, you can easily just audit those classes and not have to commit three years to school. Business school is a toss up because it’s more about the network you are budding and that’s very valuable. When I was leaving the military, I felt like I also had some knowledge gaps which business school really helped with. Rubbing shoulders with people that have business experience that you can learn from can be extremely valuable. So between law school and business school, I would definitely go with business school. But only if your interests lie within the business realm.


There’s not many veterans in venture capitalism. Do you have any advice for veterans looking to get involved in this?

Fortunately or unfortunately, it’s one of the hardest jobs to break into. We were looking for an associate and I posted something via my LinkedIn profile. Within a couple days, we had 700 applicants. So coming at it from a different direction - how can you be a better investor? I would say find operators - people that have been in the startup shoes. These people can be much more authentic advisors.


What was it like being on The Apprentice?

It was a completely on a lark that I applied. Spending 14 months in New York working for Donald Trump was mind blowing. What I learned about managing media and thinking about things in a really big way was amazing. There’s really no other way to describe it other than to say it was an amazingly valuable experience. I wouldn’t trade it for anything.


It’s so great seeing someone with a military background succeed on that show. It really shows what a veteran can bring to a civilian organization.

Interestingly, the finale was in December of 2004. 30 million people watched the finale. Afterwards, I was invited to go back to West Point and talk to the cadets and staff there. That was great and as part of my tour at the school, I was invited to go to the Dean’s office. I walked in and the Dean grabbed me and hugged me and said, ‘You did so much more for the military being out of the military than you ever could have done being in the military’.

What I didn’t realize when the show was airing was that kids were watching it with their parents and talking about business basic concepts with them. I thought that was really cool.


Do you have anything else you’d like to share with our listeners?

It’s a really big jump getting out of the military and it seems super scary. There is a massive network of people that have come before you and I will say that it is one of the most powerful networks out there.

I’m telling you that you have a massive set of skills that people recognize and you also have a massive network of people out there that are interested in talking to you about where you might like to go in your civilian career.

You’re the only one that’s in charge of your own career, so you’re going to have to take charge and go after it.