Neil Patel

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Chris Gladwin is a true business builder. It is his craft. He has now launched four startups, including one which raised $100M and sold for over $1B.

During our time on the DealMakers podcast, Gladwin shared his incredible journey of building multiple businesses. Including what’s keeping you from the funding you seek, how a business that doesn’t go as planned can still achieve a great exit, and how much you need to raise for a software startup.

Plus, we gain his insights on market timing, what it’s like to sell your company to IBM for big bucks, and the secret to creating a successful product and business.

Listen to the full podcast episode and review the transcript here.

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The Ultimate Guide To Pitch Decks

Let Your Entrepreneurial Spirit Out

Chris Gladwin was born and grew up in OH. Growing up in the midwest was about going to school, mowing lawns, and getting good grades.

He still recalls one guest speaker who was a musician. When asked how he wrote songs, he said “You just have to learn to let them out. If you’re really a songwriter, they’re inside of you.”

Chris’ inner artist was an entrepreneur, and he has certainly learned to unleash that and express it. Moving to Boston to attend MIT was certainly instrumental in this, and preparing him for startup life.

Boston was a big new world. It provided a global perspective in terms of innovation. He also found that while he might have been the smartest kid in his high school, he was now just one of many smartest kids from schools all over the world. That means you can’t afford to coast. You have to work hard.

Right out of school Gladwin went to work at Martin Marietta, and then Zenith Data Systems. He worked and learned the hardware business better than anyone else.

So, while he was still young and inexperienced in business, that enabled him to spin Cruise Technologies out of the company as his first big venture-backed startup.

Don’t Get Stuck On Your First Company, Your Third Or Fourth Can Be Even Better

Chris’ adventures certainly show why you shouldn’t get hung up on your first venture. Many entrepreneurs think it is the end all be all of their existence.

Yet, he has proven that not only can you turn what some may consider a failed startup into a great outcome, but you can keep snowballing that into something greater.

You learn a lot on the way, especially from the struggles.

Cruise Technologies was in the middle of the 90s battle for end-user computer architecture.

They were behind all but one of the major wireless or mobile clients in the market. Intel and Microsoft won that battle thanks to their giant size.

Though Chris still managed to sell the company to Motorola.

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His second startup was MusicNow. They successfully built the technology, but what is obviously a hit now, was maybe 20 years before its time then.

Chris says he saw the stars aligning for the next big shift that would change the era. So, he timed another exit. This time to Circuit City.

It was a concept that has now helped Apple make many billions, but it was just too early.

When it comes to timing, he says, “Just because you can make it doesn’t mean the market wants to buy it, so you’ve got to align the timing up of when you are coming to market to the point right when the market wants it. If you’re early, you have to find a way to last until the market is ready.”

You might be able to bring in the money to survive for five years, but not 10. If you are six months ahead you might be launching right in time.

Next was Cleversafe. By this time he says he had developed a much larger network thanks to his previous ventures.

He had also built up his playbook for financing, organizing, and team building. So, with each startup, you are compounding your strengths to build a better company the next time around.

Cleversafe fundamentally changed the whole data storage industry. They raised $100M in equity and $35M in financing on the way to selling the company to IBM for $1.3B.

He describes the acquisition as a five-month process, with perhaps 5,000 pages of paperwork. However, what really made it satisfying he says is the outcomes he was able to deliver to his investors and people.

More than 80 people ended up millionaires from that exit. More than 30 received at least $5M. He is proud of giving them that life-changing experience.

While some may think a result like that is what it is all about for themselves, and the opportunity to retire or go yacht around the world, he was already working on his most recent company before the exit was finalized.


Ocient is his newest venture. A software business that is solving big data analytics problems for enterprise customers. 

In essence, the company transforms how industries ingest, store, and analyze the world’s largest datasets, delivering unmatched price/performance levels.

Furthermore, Ocient is deploying in Auction & Exchange Analytics, Security, and Geospatial customer use cases, all built on the proprietary Ocient DAS using industry-standard interfaces and hardware, which can hold quadrillions of rows of data, ingress billions of rows per second, and filter and compute across trillions of rows per second.

They’ve already raised around $65M, and are on their way to employing over 100 people.

Storytelling is everything which is something that Chris Gladwin was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

What It Takes To Build A Successful Business

So, what’s the secret to these successes?

He says it is not about being the smartest or even being able to bring together the most accomplished team. You can get stuck there drinking your own kool-aid.

Instead, he says it is all about listening, and asking the right questions. Finding the real need that your customers are urgently looking for a solution for.

Of course, building a dominating software company today also takes a lot of money. As companies enjoy much higher values, they also require more capital to build them and compete.

When he sold Cleversafe to IBM there had only ever been five $1B acquisitions prior to that. Now, there are $100B acquisitions. Those previous companies were built with $100M to $300M in capital. That has now also multiplied to more like $1B to $3B in capital.

Again, when it comes to getting the funding for your business, that gap often comes down to listening too. He says it is not about walking from no to no from the smartest investors, hoping to find a lesser one to say yes. It is listening and understanding what’s behind the no, and using that to build on.

Listen in to the full podcast episode to find out more, including:

  • Ocient and how it is tackling massive amounts of data
  • Scaling yourself as a leader
  • Managing your time as a founding CEO
  • How much better your solution needs to be to succeed


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Neil Patel

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