1630 6:25 Failure Friday

Failure Friday: “Pitching to executives felt like an awful first date…”

In this week’s Failure Friday segment, we hear from a military spouse who sells punny greeting cards. When she’s called to pitch her idea to executives at an incubator, she figures she can wing it. How hard can it be?

6:25

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What It's About

This punny greeting card maker has faced her fair share of challenges.

Notes from Chris

Episode 1630
I believe we can learn as much from failure as we can from success, if not more. It’s with this principle in mind that we’re starting Failure Friday, a collection of short stories all about mistakes, missteps, disasters, and of course, failure.

Just like our Throwback Thursday segment, you’ll hear directly from side hustlers who have struggled to get something off the ground. They’ll tell you a short story of something that went very wrong.

The stories will vary, but often it starts with an idea, what they thought would happen and what really happened—and of course, what they learned.

I applaud their courage! I’ll share some of my failure stories along the way as well.

Today’s short story features Angelica Hanley. We told her story on Episode #970, Military Spouse Finds Joy in Punny Greeting Cards. But they had some struggles along the way. Let’s hear from them about one of those struggles… I’ll be back at the end to wrap us up.

Listen to today's episode to learn more...

 

 

MENTIONED IN THIS EPISODE: SEE ALSO: Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

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Side Hustles for Veterans and Military Families

Side hustle ideas for veterans, active-duty service members, and military spouses—real stories of portable income built on skills you already have.

Read the full transcript

This transcript was generated from the episode audio and may contain minor errors.

[Music]

Every week for the past few months, we have been presenting a segment we call Failure Friday. This is Side Hustle School. I'm your host, Chris Guillebeau. Been with you for 1,630 days in a row. Shout out to everybody who's been there since the beginning.

Shout out as well to those who've joined in along the way. And the reason we started this whole segment, it's been one of our most popular things of 2021. I believe we can learn as much from failure as we can from success. We tend to learn not just when things are going amazing, but sometimes when things are going terrible. In fact, we can actually, as I said, sometimes learn more.

So this whole segment, this feature is a collection of short stories about mistakes, missteps, disasters, and of course, failure. Just like our Throwback Thursday segment, you'll hear directly from side hustlers who have struggled to get something off the ground or have otherwise encountered a roadblock and obstacle, a challenge, perhaps one that was entirely unexpected or perhaps they were starting with an assumption, an idea, something they thought would happen. And then of course, what really happened? Then hopefully some sort of lesson out of it. But I actually like to focus on the process of the experience itself.

Like what did it feel like when you were in that moment of realizing, oh, something is not going as I hoped or expected. So I really applaud their courage. Today's story is a lot like that in the sense of, I had one expectation and then I realized pretty quickly that that expectation was going to be unmet. We're gonna let Angela Hanley tell you more about that. We first told her story on episode 970, military spouse finds joy in punny greeting cards.

Now, Angela was doing really well. She had an opportunity that she'll tell you about here, but that opportunity turned into some difficulty. So let's hear from her about that. I will come back at the end to wrap us up. [Music]

My name is Angelica Hanley and I'm the founder of A Couple Puns, a punny content and paper goods company.

Our cards are sold online and in retail shops nationwide. Now I'm gonna share a story with you where I may have cried a little bit more than I laughed, but the lessons learned from it are invaluable. A little over a year ago, I was invited to the headquarters of a popular messaging app to pitch to its executive team after applying for their accelerator program. The applications and interviews were all remote. It was pretty casual.

I heard the pool of applications was more than a thousand companies. It was a total shot in the dark. And I didn't think that there was any way that I would get an actual interview. Then came the blind side. I not only got one interview, but I made it all the way to the final round.

They wanted me to pitch in LA. Before I knew it, pitch day was here and I was in LA. I was joined by fellow applicants and we hung out together as we awaited our opportunity to pitch. I quickly learned that unlike myself, some of the other companies were total pros of this accelerator pitching thing. They had teams with expert roles, years of experience and thousands of followers.

I figured no wonder they're here. I wondered when I'd be at their level. I felt like a total underdog and the doubt started to creep in. I was not thinking about how I built a nationally distributed retail brand from the ground up, but I was thinking about the team that I didn't have. And I was thinking about the perfectly detailed business plan that I didn't have.

But you know, it's crazy. The more time that I spent with the other teams, the more I saw that we weren't all that different apart from our experience and size. We all shared passion, dedication, and I felt like we were all in the same head space. Even more fascinating was the way that our anxiety showed. I expected unwavering confidence, but they were no different from me.

Everyone was chattering nervously, meditating, pacing. I saw it all. One by one, I'd watch their stress rise and fall as their pitches passed. Then came my turn. They called me in.

All eyes were already on me. Everyone seemed excited and thrilled to see me, but still, it was terrifying. Everything was moving in slow motion until I started speaking. My mouth just started moving. From what I can remember, I'm pretty sure I championed my speech at three times speed with about 20% of the intended content.

It was a mess. A few days later, I got the bad news that I didn't make the program. I poured over all the things that I could have done wrong. Once I came down from this, I was able to reflect on the lessons, learn that it wasn't personal, and realize that I had tangible steps to take action on. Some things I learned that anyone in my shoes can probably relate to.

One, you're not a goldfish. You can memorize a speech. It's better to forget a line or two than 80%. Practice in front of humans, real ones, face to face. Stress while pitching can manifest in many ways.

It's good to be aware of it, learn to own it, and minimize it as you practice. Two, I got further than I expected because I took a shot in the dark applying. And for that reason, I was not fully prepared. Prepare more prior to applying and believe in yourself. Three, the entrepreneurship world may be very competitive in specific industries, but across the board, people are pretty supportive.

Four, have that five-year plan down. Forget imposter syndrome. Own the fact that you have goals and dreams and make plans for it. Sure, things will change along the way, but it's good to be able to see an end goal. Plan to be in that room again, whatever that may look like for you.

And five, last but not least, when it comes to starting your own business, passion, ambition, and the ability to stay very consistent is valuable. Own your soft skills. I learned passion will only get you so far. I needed to prepare more. You need preparation.

And everyone's favorite word, strategy. I may not have been selected, but the growth that came from being so far out of my comfort zone is something that's invaluable. Never confuse a single defeat with a final defeat. That is in fact the theme of Failure Friday. I'm so excited to share these stories with you.

We get lots of good feedback on them. So I'm very grateful to people like Angelica for being willing to share these stories bravely. I really like what she said about how the growth that came out of being so far from my comfort zone is invaluable. That is so often how it is, right? We have to get out of our comfort zone to find that growth.

You don't just grow and then all of a sudden realize, oh, I'm out of my comfort zone, okay? So good work for her for braving those elements, learning something about herself and also being better prepared for the next time. I encourage you to check out her website at acouplepuns.com. Remember, she makes punny greeting cards. So acouplepuns.com or follow her on Instagram or Facebook at acouplepuns.

If you've got a question or an update for us about your side hustle, come to sidehustleschool.com/questions. This has been episode 1630. Thank you so much for joining me today. I hope you'll subscribe or follow. Come back tomorrow.

My name is Chris Guillebeau. This is Side Hustle School. [Music]

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