Two weeks ago, I spent a full day intentionally subjecting myself to hours of rejection. Here are some reflections on my day at Rejectionathon.

Why would you choose to spend an entire day getting rejected?

As the Founder/CEO of an early-stage company, Cirrus Identity, I always have more things I want to do than I can do in any given week. My hardest job is prioritizing how to spend my time, so it’s hard to justify taking a full day out to run around on seemingly arbitrary challenges expecting to be rejected over and over again. The event was organized by Elizabeth Yin, a entrepreneur/investor/advisor I really trust, and from whom I’ve already learned a TON as a #500Startups #Batch15 participant. She told us she organized the event because she wished she had had something similar in her early days — an exercise to build a comfort level with rejection. I figured it had to be worth it!

Can you prepare for Rejection?

I knew the day was going to be all about doing things that made me feel uncomfortable. The day before Rejectionathon, I gave myself some personal challenges that would make me feel like a winner going in. I’ve been trying to make more time for cycling, as it really improves my thinking, and there is a popular climb near my house up the East Bay hills. I challenged myself to beat my current personal Strava record up that climb.

As I was pumping up the hill, I realized the exercise had many parallels for me in my startup life. I knew it was a long hill, so I had to set a pace that would leave me enough energy to sprint at the top. On my ride, that meant dropping into granny gear with no shame at the bottom, and focusing on the next stretch of road ahead. As a founder, pacing myself for the long haul meant having no shame about finding great advisors early on, and not being afraid to seek their counsel when I faced difficult decisions. Hill climbing and starting companies is hard, and being brazen about asking for help, and using tools to make things easier as early as possible increases stamina and the chance for ultimate success. I beat my current record by 2 minutes!

What can you learn from a day of rejection?

I found many more parallels to life as a founder than I expected during Rejectionathon. Here are a few that stand out:

One of the worst rejections is when you expect a “yes” and get a “no”

Who knew it would be so hard to get someone to let you walk their dog? It seemed like one of the relatively simpler Rejectionathon challenges, and even after the first time someone rejected my request, I still wasn’t expecting “no” the second time. The look of utter suspicion and alarm on the person’s face, even when I asked to walk their dog within their line of sight, was definitely a blow.

This unexpected rejection reminded me of the unrealistic expectations I had for some of my early sales prospects. I had some potential customers that completed successful technical trials of our product, and I happily and immediately moved them into the “opportunity” column in our CRM. They had proved our product worked, so of course they would buy! And after another year of pursuing that deal and coming to terms with the fact that the decision-makers still were not bought-in, I knew I had to heed all the advice I was getting to stop trying to persuade that customer to buy. It was so hard to let go of a deal that felt so close and where the obvious the answer should be “yes”. But to keep momentum, it’s important to learn to recognize the signs of “no” and cut your losses early.

Having a team made a huge difference!

I had an awesome Rejectionathon team, consisting of:

  1. Angie Chang, Women in Tech evangelist extraordinaire
  2. Claire McNamara from Coeio in the current 500 Startups batch
  3. Alex Choi a long-lost colleague with many startup stints under his belt

It was a lot easier to deal with all the “NOs” because we had a team to commiserate with. Alex was undaunted by the highfive snobs in Palo Alto.

In particular, I think we did a great job of actually celebrating our failures by turning them into learning opportunities. By reflecting on how our early challenges went, we learned more faster about how to improve our strategy for future challenges.

Crafting stories makes your “asks” more successful!

It was fun, energizing, and exciting to start riffing off each other as we developed backstories for our upcoming challenges. Like when Angie planted the seed of the “my sister is getting married and is looking for a place to host her bachelorette party” story line, and Claire embellished with details of the upcoming event when she scored 5 points in the “try on a robe at a hotel” challenge. Claire did a great job of emphasizing the potential value to the hotel (citing the number of attendees, hinting that they are regular visitors to the area) and the front desk staff were happy to say “yes” when she asked to try on the robe.

With my CEO hat on, and now two years of sales under my belt, I see that many of my early sales were largely made to customers who understood the way our products solved technical problems. But now I’m moving to a new set of customers where it’s much more important that I sell them on the “value” of our products to the overall business. I need to reach people higher in the decision-making chain with a strong story around value, and I also need to give the technical teams materials that can help them gain buy-in internally. Rejectionathon reinforced for me how much better my stories will be if I seek more input when creating them. I’ll be reaching out more to my team, my customers, and my advisors as I craft future stories about our services.

In the end, you have to just take a deep breath, embrace the discomfort, and go for it!

I don’t think there is really anything that can make asking to cut in a long line at Sushiritto comfortable. The first guy I asked was definitely not warm to the idea. But his rejection softened up the woman in line behind him!

The look on Angie’s face below shows how enthusiastic she was about the “walk up to a drive-through window and order” challenge. We were at a Krispy Kreme donut, so she was going to knock out the “get a free donut hole” challenge, too. After being ignored at the drive-thru ordering station, she continued to the drive-up window, took a deep breath and nailed the two-fer — and she got four free donut holes instead of one! Her ask was clear, direct, and polite, even though it must have sounded ludicrous to the drive-through attendant. And he said “yes”!

What to learn and apply from Rejectionathon to life as a startup CEO?

The aspects of my CEO job that feel like second nature are the ones that have the least to do with selling — facilitating conversations to agree on a new technical architecture, organizing a team of people to build a new service we’ve designed, recruiting people to join our team, talking to customers about how to integrate our solutions in their local environments, and creating a culture for our company to yield productivity while having fun.

While sales is the part of my job that feels the least natural, it is also the most important. So my biggest challenge is forcing myself out of the parts of my job that feel comfortable, and where I know I kick ass, into the parts that feel uncomfortable and where I’m still learning. To launch myself into a day of Rejectionathon, I gave myself a challenge in a sport where I have years of experience on a climb I’ve done many times. Succeeding at that challenge gave me an extra boost of confidence going into that day.

For the next few months, I am going to try to apply this model to my CEO life. I will set more specific sales challenges and goals (make them finite events with start and stop times like Rejectionathon). And I will be more intentional about leveraging my wins at things I *like* to do, with the sales challenges I set for myself that are less comfortable. I will include my team, customers, and advisors in developing stories to grow sales, and when we hear “no’s”, I will invite my team to learn from those with me, so together we can turn rejections into our best opportunities for success.

Oh, and we didn’t win any prizes at the end of the day. Thanks for the rejection, @Elizabeth Yin!

Special thanks to Angie Chang for the input on this post!