Before founding Ads For The Road, I never thought I would be pitching to investors and in competitions, but like my mother always said, “Never say never.” I have had a few pitch victories and a massive amount of failures along the way. I wanted to share some of the lessons I have learned while pitching with the hope that the shared knowledge will be useful.

There is a lot of information on what you should and should not do in a pitch competition or a pitch to investors. All that information is great to know when you start crafting your first pitch. The fact is, I spent weeks writing my first beautiful pitch, but my real pitch was born from falling flat on my face. The very first pitch I gave was for Patriot Boot Camp where I was selected as a finalist. It was a 2-minute pitch with no deck and a fast turnaround.

Before I reveal how it turned out, I’ll explain a little about who I am. I was a Cavalry Scout in the Army, a combat veteran who has been wounded multiple times in various firefights. I never felt nervous in a fight, and my focus always remained crystal clear. Before the Patriot competition, I practiced the pitch so many times my dog didn’t even want to be in the same room anymore. When the day came, I got up on that stage and was so nervous I don’t even remember giving the pitch. I finished in one minute (very bad), and I still to this day do not know what I said. That experience was something no book, blog, mentor or rehearsal could prepare me for. Only by jumping into the fire was I able to learn this lesson. Don’t be scared to take the leap, because ultimately, everyone in the room is there to support you, even if you black out.

I remember the next few pitches I gave, because I was less nervous than before and could catch my breath a little. The next big lesson I learned was during a pitch for TechStars to make it into the final ten. It was a 7-minute pitch, which seemed like a lifetime. The pitch went awesome, I hit every mark I wanted, and it felt smooth. However, I was not ready for some of the more in-depth questions that came at me after the pitch. I did learn that you don’t need to know the answer to every question, but you had better be able to answer every question about your company and its direction. If you don’t know the size of the market, competition, hurdles you’re facing, go-to-market strategy, or most importantly, your numbers, then you are dead in the water. Take some time to sit down with your team and truly understand the details of the business, and do some additional research on the market and industry. Then, you will have the ammo you need to fire back at those questions.

The pitch that is going to hurt the most is the one that loses you money. I once flew to another state to pitch potential investors for my company. I got together the whole team to help me build the best pitch deck and craft the best presentation to date. All of my team’s planning was wasted. I did not even get the chance to pitch. The investors who invited me there were not responsible for the bloodbath that took place. It was an unforeseen investor whose opinion dominated the meeting. The entire time I was on the defensive rather than on the attack like I had planned. This meeting was the most painful failure I have had to date, but it was also one of the most eye-opening. It gave us visibility to issues that needed to be addressed, and because of that failure we have already improved the company by leaps and bounds. The lesson from this pitch was no matter how much negativity gets dumped on you, dig deeper and use the experience to make you and your company better.

I am taking everything I have learned to the next big pitch at the Veteran Business Battle at the end of this month. It’s the longest pitch I have had to do at 10 minutes, and I am looking forward to the opportunity to learn something new.

I wish I could tell you that it’s going to get easier, but the hard truth is it never gets any easier, but YOU will get better.

Written by Justin Gilfus

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