How I shoot my shot in public and what I learned

Most founders and creators struggle with taking a shot and making an ask in public.

Why?

It tends to be because they prefer to guard their personal brand/ image so carefully that they can’t afford to face a public rejection and thereby risk lowering their status in the public eye.

Additionally, they don’t want to come off too desperate.

A lot of people no matter how small or big their brand is .. unconsciously live by this fear and never take their chances.

But you won’t know the answer to your “ask” unless.. you make the ask. You will never get what you want in your life or career if others don’t know what you ..want.

I’ve learned that facing your fear of rejection is an essential tool if you want to be successful. And more importantly, your personal brand will only get bigger if you take meaningful risks and show your vulnerable side in public. This is obvious to me now. But it wasn’t always… even just 4 years ago.

Early days in my Twitter journey, I was terrified of facing rejection. I assumed rejection meant people would judge me as a worthless idiot.

Until one day I accidentally discovered the power of ‘shooting your shot’ with the below tweet to Gary Vee. Earlier that year, I started a fledgling podcast called “BUILD IN PUBLIC PODCAST”. Gary has been my inspiration for more than a decade. In the back of my mind, I’ve always wished to have Gary as a dream guest for an interview on the show. That Sunday morning March 7, 2021, I had a weird hunch to just tweet at Gary and make my ask boldly. I had zero expectations because my podcast was young and only had 3 episodes until then but boy did that tweet change my life!

https://twitter.com/thisiskp_/status/1368620073741586434?s=20&t=vrZDQ1PqcvI9H776WkKEOw

Here are some key wins after that:

Gary Vee agreed to join me as a guest on my fledgling podcast and his team even put my interview on his official Youtube channel
Got to interview Alexis Ohanian as a guest on my podcast with a similar ask
Landed Kat Cole as a podcast guest on podcast
Landed Gary Vee again on my Founder Hotline show
I landed my last 2 startup roles by mostly shooting my shot and being public about my intentions [this and this]

I am 100% certain that the answer was NO for all of these if I didn’t make the ‘ask’.

Of course, it wasn’t all roses. There were rejections too.

Here are all the times it didn’t work:

My public ask to Kunal Shah tanked in public
My public ask to Ali Abdaal was ghosted
My public ask to Shaan Puri was ghosted
many other times

Here are my top 9 lessons:

Shooting your shot is not about getting a WIN every time but practicing the courage to risk publicly.
Rejection stings but it’s part of the game. It’s like a muscle and gets stronger over time and you’ll learn to take it less personally.
No one owes you sh*t. Especially busy and influential people.
Offer an easy way out for them to say no. I typically include a line that literally says “No obligation or ready to take a NO” which lowers the pressure at their end. Ultimately, they’ll assess whether it’s worth their time or not but if you make it easy for them to say NO, you come off as less desperate.
Always craft a simple and clear ask, don’t dance around it. Just say in simple plain language what you’d like.
Have low expectations. Many of the influential people get 100s of such asks daily so have low expectations.
Offer a clear why. Find what’s a unique thread that connects you and them and include this in your ask. People want to know why specifically you choose to pitch them.. and the reason can’t be *just* because they’re famous.
Get ready to be persistent and patient even after the answer is a ‘YES’. I had to quietly follow-up with Gary’s team for 3 months before we worked out a free slot. I had to wait 4+ months for Alexis and followed up 5-10 times in the interim with gentle nudges. It’s important to stay patient.
At the same time, don’t nag or follow-up too aggressively in an entitled tone. Remember that they’re likely doing you a favor if they are influential so be patient and humble.

That’s a summary of my experience with shooting my shot in public. Now, I want to hear from you. Have you experimented with this technique? Has it worked? What was challenging for you?