Expect Rejection: Learning from every ‘No’ in sales and online dating
Written: 08-15-2017

There is a new podcast by Reid Hoffman (founder of LinkedIn) called ‘Masters of Scale’. It is a master class in startups with many of the top founders and CEO’s. The guests include successful individuals such as Brian Chesky, Sheryl Sandburg, Mark Zuckerberg and Eric Schmidt. If you only have time to listen to one episode, having listened to all of the episodes to date, my suggestion is listen to the Reid Hastings episode. It is the story about how he created culture at Netflix after learning hard lessons at Pure Software. I’d also recommend that you go view the ‘culture deck’ that they talk about within the episode.

As a bonus learning tool, they published an episode with Tim Ferriss. In that episode, Ferriss takes all the lessons and provides commentary and insight. He pulls together a “10 Commandments of Startup Success”. It was listening to the discussion around the first commandment that I realized that I’ve been getting an entire PhD in startups over the past eight months. I say it’s my PhD because I am now on my fifth attempt at creating a viable and sustainable company. Three of those companies are still in operation and at very different stages, so I would like to focus on Upper 90 and what I am learning through it today.

For context, Upper 90 is a development and sport science company at its core. We have a product that we are trying to bootstrap called PyCoach. PyCoach is an athlete monitoring platform that provides a window into an athletes readiness to perform, for coaches and performance staffs. In addition to the saas product, we provide data management consulting services for colleges and universities that are trying to better utilize data on their athletes.

Back to Tim’s first commandment of startup success,

“Expect rejection. But learn from every ‘No’”

This is something that I have heard successful startup founders and mentors talk about in the past, however I do not think that I have been in a mindset that allowed me to learn from rejection. Rejection was something that hurt a little too much and dug a little too deep for me to ever have a clear and positive reaction.

If you would have asked me about this in the past, I would have likely said that I was able to understand and learn from rejection. However, I had confused the difference between “rejection” and “failure”. There is another common saying in startup culture: “fail fast”. While I absolutely hate failing, I have been able to mature to a point where I understood that failing in the right ways can often be positive in the long term. I drew upon my knowledge and experiences in athletics to help me get to this understanding. In athletics, I have always been able to use poor performances to be the foundation for better performances in the future. The striving and self-competitive mindset becomes addictive. For example, I recently started to rock climb. I am absolutely horrible at it, however I know with each attempt I can learn and grow.

The “fail fast” paradigm isn’t what is meant when the commandment “Expect rejection” is shared. It has taken me awhile to work through this, plus a decent amount of therapy, but I now understand that a rejection isn’t (or doesn’t have to be) a failure. As I look at the two, I see failure as an outcome. In many cases it’s a binary outcome (the easiest to learn from), but it doesn’t have to be. Rejection is more of an interpretation by someone else regarding what you are offering and their desire and need for that offering.

This seems very nuanced, I understand the confusion, so let me share a couple ways that I am currently learning from rejection, but in ways that I don’t believe is failing.

Online dating as a window into rejection:

I’ve been talking to others for awhile about what it’s like to date. I was never good at it the first time around, so it’s pretty anxiety inducing to think about trying to do it again 15 years later. It’s even more challenging when I realize that I don’t have too many settings where it makes “discovery” possible. This is when I started talking to my friends about their successes. I learned that several friends met their partners on Match, two meet theirs on OkCupid and another friend has been using the Bumble app. Inspired by their stories, I first joined Bumble, a week later I signed up for OkCupid and after brief periods of time on those platforms, I’ve moved on to Match and Tinder.

What I’ve come to learn through experience and reading of others, is that volume of interactions is essential for men to be successful. It seems very counter intuitive to my long term romantic notion that you just meet someone as they walk into the room and you know they are the one. The idea of sending out dozens of messages to get no responses, then feel empowered to carry on, is difficult. Whether I want to admit it or not, there’s at least a small feeling of rejection every time I send a message and hear silence.

A reality of using the platforms is that it’s unclear why no response is given. My first interpretation is that she read my message, reviewed my profile and gave the hard pass. However, it’s a story I’ve made up. At least on Match, I realize now that there are profiles that are active yet the person never uses. So another possibility is that she never saw the message. The uncertainty of the situation makes managing the process that much more emotionally challenging.

The value, for me, of using an online platform at this stage of understanding how to date in a modern world, is that the individuals on the opposite end of the conversation are mostly unknown. I do see people I know on the platforms and for the most part I do not engage in conversations with them, as rejection from someone I already know might be too difficult.

The main lesson that I’ve learned, that applies to this discussion, is that there are many stages along the dating path. At each stage, the opportunity for rejection exists. While I have not experienced anything beyond the initial stages of communication to this point, I anticipate that the pain that comes along with rejection also increases with each step forward. As commandment number one suggests, “Expect rejection, but learn from every ‘No’”. If rejection is not a failure nor a binary outcome but an interpretation of your offering by someone else, what can I learn from rejections in the dating world? Here are some thoughts:

1. Did the person communicate values they desired, that I did’t offer? For example: family, political or religious values.

2. Did she want someone that has the personality that I possess? If not where there early signs?

3. Did I communicate my values and desires clearly upfront? Is it possible to improve the way I represent myself better?

Startup sales as a window into rejection:

I am not a great salesman, but in the initial stages of most startups , founders find themselves taking on roles by default. That is where I have found myself many times over the past eight months. Whether it be selling PyCoach to colleges and universities, or selling our consulting services, I have come to realize that you can take all the lessons I just shared about online dating and transpose them into sales. In fact, it’s not uncommon that I find myself sending sales emails to a college coach one minute and then responding to a message on a dating app the next. The majority of messages I send out, even to a coach I have a direct connection with, receive no returned response.

In the sales process, I have had several situations where the communication back and forth start to create feelings of shared vision and alignment. In at least two of those situations, what felt promising and potentially life-changing (for a small bootstrapped startup like us anyway) resulted in eventual rejection. It hurt. What are a few things that I learned from those hard “No’s”?

1. I got a little caught up in the potential sale, even when the customer didn’t exactly fit our targets.

2. I struggled to communicate our value prop in a clear manner.

3. I lost track of the stage of ‘courtship’ we were on, partly due the timing and impending decisions being made.

Some final thoughts on rejection:

Everyone goes through rejection. Going through the process of getting rejected doesn’t mean it’s a failure, however that also does not mean it won’t be a little painful. When I listened to the Master of Scale summary episode with Tim Ferriss, I initially was not sure I believed that a lesson about rejection should be commandment number one. I do now. If not number one, than at least in the top three, because without being able to manage rejection well a founder will never possess several characteristics I believe to be critical:

1. Resilience

2. Self-awareness

3. Humility

If all of this is true, how does someone practice getting better at handling rejection? There are workshops targeted to founders that need to learn about product development, financial processes and fund raising, however I’ve never seen a weekend seminar focused on rejection. My guess is that handling rejection is something we are expected to know, or that we were taught how to handle it at a young age (which doesn’t seem likely, especially in today’s environment).

I believe that we should practice and prepare for important things in our life, to which I’d encourage a founder to not wait until their first big deal to find out how they’ll react to getting turned down. If you are not ready or in a position to face consistent rejection that comes along with online dating, my current training ground, I’d recommend you start small and with something that is very low stakes.

Noah Kagan created the coffee challenge several years ago as a way to get startup founders exposed to the feeling of being rejected. If you haven’t completed the challenge, I’d encourage you to start there. If asking for 10% off your Starbucks is difficult, how will you ever face the risk of rejection associated with your business contracts worth thousands or millions of dollars?

By doing the challenge you’ll learn a lot about yourself, including whether you are an ‘asker’ or a ‘guesser’. I’m 100% a guesser, which is why learning about rejection is so fundamental to my growth as a person, startup founder and romantic partner.


1. Master of Scale Podcast

2. Netflix Culture Deck

3. Tim Ferriss summary episode of Masters of Scale

4. Noah Kagan’s Coffee Challenge

5. Brene Brown’s talk on vulnerability (which is a requirement, imo, to face rejection)