Remember your first time?

I remember my first time so well.
It was Spring 2007, and I was an inexperienced 21 year-old getting ready to graduate and enter the real world. My brother Yu-kai Chou had already done it and I thought, “Yu-kai seems like such a Fob. If Yu-kai has done it, then I should be able to do it as well!”
I was nervous. I had consistently heard my peers talking about how good it felt, and those wild college success stories made it seem like it was just so easy to accomplish. It was my last year in college, and I knew if I didn’t do it now, there was just no way I’d be able to do it later on in life.
So before graduating, I took a deap breath, took the plunge, and became a man…
I founded The Veridical Group that Spring 2007. It was my first company, so it was riddled with mistakes, failures, and was full of naive undergraduates that thought we could take over the world. Just thinking back makes me laugh at how incredibly inexperienced and oblivious we were. At the same time, I’m so happy I did it. Creating The Veridical Group built the foundation for me to later start Future Delivery and now Viralogy.
I’ve also realized just how closely related my first time starting a company was compared to my first time with a girl:
1. Faking confidence was just as good as actually being confident
When you’re the CEO of the company, it means that you’re ultimately responsible for the direction and success of the company. If the CEO is confident with the direction of the company, then this feeling of confidence will spread across the team; if the CEO is worried or unsure about the company, then the team will feel nervous and uncommitted. Even if this is your first time as CEO, you need to fake confidence in order to successfully lead your team and gain their respect. Though I had no idea what I was doing, I learned how to speak with gravitas and fully commit the company towards a direction. Always speak with authority, be compassionate towards your team members, and lead with questions.
Yes I was nervous, but I knew it was her first time as well. I thought about it rationally and came to the conclusion that if this was really her first time, then she really had no idea what’s good or bad, or right or wrong. So I decided that every action that I would do in bed would be done with complete conviction and confidence, as if it was my 100th time doing it. I would also take the lead, and give direction as much as possible to “seem” like I’m in charge and that I know what I’m doing. By sticking to my plan, I lasted a good 10 minutes and at least “felt” like I did a good job.
2. Communication is just as important as what you have
I’ve learned that it’s not just about having talented people on the team, but more importantly, it’s about placing the right people on the team in the right positions in the company (via real life experience and Good to Great by Jim Collins). With the Veridical Group, I had assembled a team of highly motivated, highly talented peers that were ready to go to work; however, I made the mistake of NOT assigning them specific positions and responsibilities. Because they didn’t know they’re exact role in the company, we ended up wasting many hours on non-productive activities and actions that ultimately did not bring value to the client. If you’re starting a company, take the time to thoroughly understand your team members’ strengths and weaknesses so that you can place them in a position that takes full advantage of what they’re good at and what they love to do.
My plan was to fake confidence and give orders so that I would seem like I knew what I was doing. At the same time, I had no idea how long or how hard to grab a certain area, or when and how hard to spank, or even how deep to go. About a year after my debut, my girlfriend at the time and I reminisced about our first time. I asked her, “So be honest, did you like our first time?” She replied, “Well, you seemed very confident (hahaha, my plan worked!), but I wish you had asked me how I liked it instead of making it all about yourself.” Lesson learned.
3. Protect your assets
If you’re starting a business, make it official. My partners and I created an LLC with Legal Zoom and each put in $100 of capital contribution. Never half-ass a company. If you require capital contributions and write out written Operating Agreements that each team member must sign, then it makes the company “feel” significantly more official and you’ll know that your team members are fully committed.
Yes, I wore a condom
4. It felt good to just get it out of the way
Starting and failing my own company was good for me in several ways:
- I realized that starting a company was really not that hard at all
- I felt what failure was like so I no longer feared it
- I was able to compare the corporate world with the entrepreneurial life and make an informed decision about which one I wanted to pursue
Debuting at a young age was good for me in several ways:
- I no longer needed to pretend or lie about it
- I realized that girls get just as nervous as guys
- I knew what it felt like so I didn’t have to be as nervous the next time
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Would love to hear your stories about your first time






Nice analogy here - as I set to embark down this path myself, your advice here will serve as wise wisdom. I especially agree with faking confidence even if you’re not confident. When you become the CEO of a company, startup or otherwise, you’re expected to know your shit, you’re expected to run the show - so even during those times of weakness and doubt, you have to put the best foot forward and be externally confident. The minute a client or your team senses doubt and uncertinty is the moment you start to lose credibility.
Again, great thoughts here Jun!
Thanks Matt. You might have already spoken about this, but what startup will you be creating? I’m very interested in learning more about it and offering as much 1st hand advice as I can.
Either way, I think you’ll do great!
Great comparison, Jun! Ha ha… I haven’t had my first time starting a company and leading a team of people, but I sure have had my first time with a girl. Although there’s no way I can compare the two since I’ve only experienced one of them, I can relate to what you mean by faking confidence. This kinda follows the BE-DO-HAVE principle. It starts with you being the person you want to be, then doing as that person would do, then having what they’d have.
Here’s a quote by Richard Bach that I like about ‘fake it till you make it’.
“To fly as fast as thought, to be anywhere there is, you must first begin by
knowing that you have already arrived.”
Cheers~
Mark
Wow, great quote Mark!
You should try starting your own company. Feels almost as good
You still writing your blog?
Yup, I’m still writing my blog, though less frequently cos’ I’m more focused on marketing my free eBook to build my list these days.
Cheers~
Mark
Lol, Just dont let the girl know you are thinking of your business at the time. Bit of a mood killer I think.
I feel that some of your advice here is at odds. I agree that if you’re going to start a company - no matter how small - it’s important to take it seriously and do it right. Writing up an Operating Agreement is one good example of that. But to say “just get it over with, start a company because it will likely do poorly” is kind of the opposite of taking it seriously and doing it right.
Fortunately, reading your experiences is a learning opportunity for your readership also, kind of like starting a company. So in my opinion the key is just to always be learning (from everything - your mistakes, your successes, others’ examples, the advice of luminaries in even unrelated fields, etc.) and thinking about how you can do things better. No matter where that inspiration comes from. And definitely do take your work seriously; if you’re going to do it, strive to do it right.
Concerning the business side of your analogy - you’re spot on about confidence and the importance of learning to fail. It took me a little while to figure that out - how to be confident despite it feeling like everything is going to crash down around you. As you said in your article, confidence is contagious, so to is lack of it. It’s amazing at how just being confident will allow a difficult situation to seemingly fix itself.
Learning to fail is also critical as you stated.I wonder how many people have fell short of their true potential due to fear of failure? It has been said that in most cases at the end of a person’s life they regret not what they did, but what they didn’t do for fear of failure or rejection.
I am working on having my first time. Set up the LLC. It makes me nervous. Your analogy is quite accurate.