How a Game of Paper, Scissors, Rock Helped Build a Company that Sold for $1.8 Billion

with John Pestana

How a Game of Paper, Scissors, Rock Helped Build a Company that Sold for $1.8 Billion

I recently interviewed John Pestana and he told me an amazing story of how a game of paper, scissors, rock helped grow his business which sold to Adobe for more than $1.8 billion.

John was in a class with me during my junior year in college. Since then, John has been a phenomenally successful entrepreneur. He was a co-founder of, which he sold as his first exit. He then co-founded Omniture, an enterprise analytics company, which he sold to Adobe for $1.8 billion. He is currently the founder and CEO of ObservePoint, a data analytics company.

Here are a few of the monetization secrets from my interview with John. 

Creating “Wow” Engagement

While John was working at Omniture, they sponsored a lunch at a large software conference. Normally whoever sponsors the lunch has a chance during the meal to stand in front of everyone and speak about their company. John and his team noticed that nobody ever seemed to pay attention during these little speeches, and they wanted to find a way to change that. 

Instead of standing up and speaking about their company, they decided to hold a paper, scissors, rock competition for the attendees. The winner would receive a hummer. As you can imagine, attendees were absolutely thrilled to participate. Participants collected business cards from everyone who participated and had them chant “Om-Ni-Ture” instead of “paper, scissors, rock.” 

This “wow” moment was unforgettable and created amazing brand awareness and lead generation for Omniture. As we try to engage with potential customers, we should try to think outside the box and create “wow” engagement. Some ideas may fall flat, but when we succeed we have a chance to become legendary.

Agility and Grit

“The people who become really successful have agility and grit. They just keep going no matter what. When you fall flat on your face, you just pick yourself up and keep moving.” 

– John Pestana

the people who become really successful

Embracing Data, Good or Bad

“I’m not afraid of data. I actually want to know if something is bad. There are so many people who don’t want to know the bad things. I want to know the bad things because the only way I can fix the bad things is if I know about them.”

– John Pestana

Connecting With Every Employee 1-on-1

Within 3 days of becoming the new CEO of ObservePoint, John had done 1-on-1 interviews with every employee. Now, every 6 months John does an interview with every employee (100 people), even the part-time interns. These interviews build John’s credibility with his team and show that he cares about them and their thoughts and opinions. If there is anyone a CEO should be talking to, it is the front-line customer service reps who are working with the customers.

Obsess About Customer Happiness

We should obsess about customer happiness. Live and breathe it and instill it throughout our company. 

To be credible, we must know our industry well enough that we are a credible source of information. We also must know our customers well enough that we know what is going to help them or not. 

When we do a good job helping solve problems for our customers, they start coming to us and asking us to help them solve other problems in their business. It is tempting to want to take that additional work, but we have to ask ourselves if that is a business we want to be in. We don’t want to destroy our credibility in the things where we are experts because we took on additional projects where we were not experts and performed poorly.

Most salespeople just spew out information when they are trying to make a sale. That doesn’t work well. We should never start off that way. The first thing we do is ask potential customers about themselves and their problems. Then, we know how we can make them happy. We can then focus on solving their problem instead of selling our product. When we listen first, we are more credible because we are giving people what they need.

The Power of Saying “No” and Setting Good Expectations

There is a power in saying “no.” By saying yes too much, we can destroy our credibility. We don’t have to be everything to everybody. We need to understand what we are.

Credibility is doing what we say we are going to do. That is a two-sided stick. We obviously need to do what we say we are going to do, but just as importantly, we need to set proper expectations upfront about what we are going to do.

The Results Pyramid

When we want to see new results in our companies, we tend to focus on giving out many new orders and action items. However, in order to receive the results we truly want, we need our team members to understand why there are new actions and to believe that we can achieve the results we’re reaching after. So the first thing we need to do is create experiences that can change beliefs. Those changed beliefs will lead to changed actions, which will ultimately reward us with the results we’re seeking. 

When John started as CEO at ObservePoint, customer retention was only in the high 70’s. He told his employees that the company goal was to bring it up to 95% retention. When his employees heard this, they rolled their eyes. They needed to have experiences that would help change their beliefs that it was possible to achieve that result. 

So John started giving them those experiences. One example he shares is that in the past when they needed to have a team meeting to solve a service problem, the team would look at their calendars and schedule something 2 weeks in the future. Under John’s leadership, he stated that they needed to have an emergency meeting at 5 p.m. that day to solve the problem.

After six months of having experiences like that, John asked his team who believed him when he first said that they would have a 95% retention rate. Only two members raised their hands. He then asked who now believed that they could achieve a 95% retention rate and every employee raised their hand. 

Leveraging Associations & Tradeshows

When we serve in industry associations it is a way for us to give back, and it is also a way to give credibility to our companies. 

We should carefully track the return on investment from every trade show so we know which ones convert and which ones do not.

Trade shows aren’t just about finding new customers. They are also about being in touch with our current customers. Trade shows can be effective ways to meet everyone in person, as opposed to having to fly out and meet everyone individually.

It’s important to know the metrics that we will use to measure the success of a trade show before the trade show. Otherwise, it’s too easy to come up with statistics to justify an ineffective decision after the fact.

Using Zoom Effectively

Meeting someone in person helps build credibility. During COVID, we need to figure out ways to do that virtually. We must treat Zoom professionally so it helps to build and not detract from our credibility. When we are using Zoom, we need to have a professional Zoom photo, get ready for the day, and have good lighting. If you don’t have professional lighting, at least face a window instead of having a window behind you.

When we are using Zoom, we should try to create as close to an in-person experience as we can. For example, when John does company meetings over Zoom, he calls out people who are not sharing their videos, because it is important that we see each other, even if we are not the ones presenting. As John is presenting, he will engage people and make it feel more human and not too produced or fake.

The Power of Extending Trust First

One of the most important things about trust and credibility is not being afraid to extend it. If in every interaction we force people to gain our trust, we are never going to gain the trust of anybody. We should give our full trust in every relationship upfront and take the risk that we might be hurt. When we put full trust in others first, they will generally extend trust much faster to us. Then, we need to do everything we can to be sure we don’t break that trust. 

when we put full trust in other first, then

As we work hard for others, give to others, and strive to help and make others happy, we will see it come back to us tenfold.

Connect with John and His Company

If you want to learn more about John Pestana and his company:

John Pestana’s LinkedIn –

ObservePoint –

Monetization Secrets

Thank you John for sharing those stories and secrets. Here are some of the top monetization secrets that stood out to me from today’s episode: 

1. We should try to create “wow” engagement moments with potential customers to be unforgettable and maybe even legendary like Omniture did with their paper, scissors rock competition.

2. We should embrace data, whether it’s good or bad, and make data-driven decisions.

3. We’re all going to stumble and fall. We will be defined by the moments we have picked ourselves up and kept going. 

we're all going to stumble and fall

4. We should obsess about customer happiness and use the power of “no” to set great expectations.

5. We must extend trust first if we want to gain credibility.

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If we desire monetization we have never before achieved, we must leverage strategies we have never before implemented. I challenge each of us to pick one thing that resonated with us from today’s episode and schedule a time this week to implement it to help achieve our monetization goals.

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When have you observed businesses create “wow” moments of engagement with their potential customers? Please join our private Monetization Nation Facebook group and share your insights with other digital monetizers.

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    About the author

    Nathan Gwilliam

    Nathan Gwilliam

    I help organizations navigate tectonic shifts that are transforming the business landscape, so they can optimize marketing, accelerate profits, and make a greater difference for good.

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