Justin Weissberg: “How to build the right team for your business”

Time management — Time management is a skill that most people have yet to master. As an entrepreneur and business owner, it is my job to choose what we invest our time into and doing what we think we can get done best. As a part of our series about entrepreneurs who transformed something they did for fun […]

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Time management — Time management is a skill that most people have yet to master. As an entrepreneur and business owner, it is my job to choose what we invest our time into and doing what we think we can get done best.

As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Justin Weissberg. Justin is the co-founder and president of Kast (, the Online Hangout Platform for friends that want to play together, watch together, and be together in the digital space. Justin competed at the highest level in the United States on titles like Call of Duty 4, Gears of War, Call of Duty MW2 and World of Warcraft, before creating Kast. Between 2011 and 2013, Justin got heavily involved in the esports gambling scene during the global launch of Valve’s Dota 2. His time as a professional gamer has given him first-hand experience with gaming communities, streamers and the handful of leading third-party applications that currently ties the gaming scene together. He works alongside passionate individuals who hail from diverse backgrounds across the globe, coming from fast-paced and exciting industries such as esports, video streaming, entertainment, and video games. Kast has a team of 21 people with offices in both San Diego, California, and Helsinki, Finland.

Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

Growing up in Southern California, I took part in athletics and sports at my school. I loved being physically active, but what I loved even more was video games because they provided me with an escape from reality; the divorce that my parents were going through. During that time, I found that playing on my PC and Xbox was the only place where bullies in middle school and high school would be nice to me because I could help them win games.

It was also during high school that I started getting into popular titles such as World of Warcraft and Call of Duty: Modern Warfare 4, and not only was I good at them, but it helped me make friends and connect with like-minded people across the world. It’s here where I made friends that I still have today, 15 years later.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah-ha” moment with us?

I was very lucky to be surrounded by a lot of successful people in my life and many of my mentors that supported me during my childhood turned their passions into very successful businesses and either exited via private transaction or IPOs. Watching them start a new business due to the lack of innovation and drive within the companies that they previously worked for, sparked the inspiration for me to do the same thing; create a business or concept that solved an important problem.

During my time on the early esports scene, I saw that there was a world of people who wanted to be connected when gaming competitively, but they were very limited by the tools available at the time, which included Skype, Ventrilo, and TeamSpeak. This then got me thinking about how vital it was, specifically for esports teams, to not only be able to hear what their friends were saying, but to see game play in real-time. My “ah-ha” moment for this concept came during an esports tournament setting where my money and reputation was predominantly online.

There is no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

Building up a group of mentors is one of the main reasons why businesses become successful and this has fortunately been the case for me. It’s a team sport that requires people with different specialties to come in and help build the business to its full potential. I overcame this challenge by building an accountability network of mentors that specialized in different aspects of the business that I was trying to build, and asked them for help.

Some people can really struggle knowing where to start, so before Kast was built, we gathered data to understand what the real needs of our potential consumers were. This avoided speculation and from here, knew what would actually work rather than planning on the fly. Everyone has ideas, but the key is to believe in what you are doing, build something to test it, and then iterate based on data.

Having that “A-team” behind me meant that I could focus on building a great company culture so that we could all adapt to the changes we needed to make, based on new data when it came in.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

Juggling a lifestyle that you may have already built for yourself can be hard. Where is the income coming from? Will I have time to do this? What about a good work/life balance? I don’t want to burn out before we launch!

These are all thoughts that, when looking from the inside out, can be quite daunting when going it alone, so don’t be too proud or too afraid to ask others who have turned their hobby or passion into a business, for advice. Ask as many questions as you need and surround yourself with positive and honest people who will not only help you on your journey, but also provide criticism and feedback when you need to take a step back to look at the bigger picture. Never settle for what you have and be open-minded because you never know what you are going to learn.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

I will focus on the aspects of the business that only I can contribute to, so I employ other people that can do those other things better than me. I surround myself with mentors who not only help me, but push me to challenge myself to learn new things.

I have always said that anyone can specialize in a subject and become an expert in that topic, but the minute we stop learning something is the moment we stop enjoying it. So, keep yourself fresh, push for new boundaries and never limit yourself during that process.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

Without a doubt, the most important part of the business is the people you work with. I know that every time I go into the office, I have a group of people that I can count on to help me run the company. It’s just like the team sports I used to play in High School; my colleagues count on me to be the best version of myself so I can accomplish the work only I can do, and in return, they can focus on their own tasks.

I love to work with people on hard problems to then eventually turn them into solutions which can then be translated into incredible customer experiences for our community to enjoy.

One of the downsides of running your own business is that there are sometimes new frontiers that you venture off into, which for some people, can be quite daunting. But, for me personally, I love exploring because it makes life a real adventure where the possibilities are endless, but also possible. I like to keep my mind and body healthy so that I can then can work more efficiently and support my team.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

I honestly never thought that I would end up sitting in front of my computer as much as I do now; I had an image in my head of back-to-back meetings or working on big projects — this part, so far, is true. There are weeks where I have to knuckle down and focus on a project, spending hours building PowerPoint Presentations and working on materials, but the diversity of what I do now means that no week is ever the same. I can be on the road pitching to investors and meeting new people at events all around the world, but then some days I am in the San Diego or Helsinki office working on business development opportunities.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

Never. There is never a dull moment when working in an environment where you are constantly learning and that’s one of the great things about starting a business. It all goes back to my earlier comment about how important it is to not only work as a team, but to surround yourself with people who make you want to learn more and pursue that vision alongside you.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I remember a story from when I was fundraising for our first round. Being young and slightly inexperienced, I asked an investor to write me a check for a certain size; he was more than happy to oblige, but mentioned that he didn’t write checks that small very often. After he wrote that check, he later told me that I could have asked for a lot more money. I will never forget his kindness — he later wrote me a bigger check for the same round I was seeking funding for.

The biggest lesson I learned is that if you don’t ask, you don’t get. Don’t settle for small and ALWAYS ask for what you want — it’s then up to the other people to say no.

Who has inspired or continues to inspire you to be a great leader? Why?

There are two people in my life that have inspired me to be a great leader. Firstly, my grandfather. He told me to never settle for anything and always make what you want to happen, a reality. He also taught me the rules of 80/20; If there is something that you can do 100% of the time and that task takes up 20% of your time, find someone who can do it 80% as well as you and give them the resources to achieve the other 20%.

The second is my business partner, Mark Ollila. Being a successful businessman and leader himself, he taught me that being a leader is both a gift and a responsibility and how vital it is to focus on giving your team the resources they need to be successful and then get out of their way. He also taught me that the best business leaders build businesses where they are replaceable and therefore not needed in decision making at all times. Empower your team and push yourself to work ON the business, not IN the business because if you are working in the business, you are taking yourself away from other tasks that only you as an owner and operator, can only do.

How have you used your success to make the world a better place?

Although it can be tricky to get away from the startup grind, I love to visit schools and inspire kids to go off and pursue their dreams. I want to help people understand that they can push themselves to do, and achieve, whatever they want without having to limit themselves.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. How to fund-raise — Fundraising is a vital cog in the wheel of most startups. It is an art and a skill, though, and I wish that I had a mentor that had taught me early on and helped me save time instead of going through trial and error. The silver lining of it all is that I have now taken those self-taught experiences and learned from them.
  2. How to build the right team for your business — Having a strong team of passionate individuals is something that I have mentioned frequently throughout, but I have to stress that without the right team behind you, nothing is going to happen. Sometimes when things are moving fast within the business, it is your job as the owner to bring in people that can get the work done. Figure out who you can train to fill a specific role and give them what they need to get going.
  3. Working with and managing people — We as humans are wired to be hands-on. Empowering your team is the most important things that you can do as a leader and that is something that most people fail at daily. Kast co-founder and CEO, Mark Ollila, is a great partner and mentor. He pushes everyone to do the best work that they can and empowers them to get jobs done. He taught me that if leaders have to micromanage, then the business is not executing at its full potential. He has helped build Kast in such a way that we can operate by empowering people, not by micromanaging.
  4. Time management — Time management is a skill that most people have yet to master. As an entrepreneur and business owner, it is my job to choose what we invest our time into and doing what we think we can get done best.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire 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.

Video games help people to become more social. I know for a fact that if I didn’t have my PC or Xbox rowing up, I don’t think I would be as open-minded as I am and would certainly not have met the friends that I made 15 years ago. Being privileged enough to spend time with people from many cultures across the world allowed me to understand how we as humans need to have that feeling of belonging somewhere and sharing experiences with like-minded people.

To me, video games are a gateway to a whole other world that is at the end of your fingertips, screen, keyboard, and controller. Gaming empowered me to be more business-minded through experiencing the buying and selling of virtual goods to make virtual and real money, networking with gamers to find people who could do things that I couldn’t do inside of a video game, and build a team of party members to accomplish a unified a goal inside a game. If those three pieces aren’t building a business, then I don’t know what is!

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

This life lesson came from a conversation that I was having with a close family friend: Running a startup is no different than running a privateer Formula 1 race team. You are there to win the race. It doesn’t matter where you are in the race. Your goal is to keep the car on the track until you win.

This was particularly relevant to me because F1 racing and startups face many of the same challenges. It is high energy, there are big personalities, and you can only win if you have the right team. A great example of this is that you can have the best driver (product) in the world, but if you don’t have the best pit crew and engineers (community, support, engineers, experience teams), you will never be able to get in and out of the pit as fast as possible (push product updates and support growth), and keep the car on the track (product live) to win the race.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

SoftBank CEO Masayoshi Son — I wrote a paper about him when I was in college as I really respected all the hurdles he had to jump during his earlier years in life. His tenacity and vision are reflected in how he operates his business. I respect what he has done and achieved, but I also admire his self-belief during the dotcom boom when people thought he was crazy but he pushed on further to build a world that he envisioned. Haters will always hate, and I respect the man for sticking to his vision and pushing himself, his company, and the world, to build and execute a vision that he wants to see realized. In my opinion, he is doing just that.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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