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“It is never a straight line to success, there are always ups and downs, and you have to prepare for that” With Matt Holleran

…when you fund a company, it is never a straight line to success. There are always ups and downs, and you have to prepare for that. What’s more, the financial markets and the venture market have huge swings of their own, so you also have to aware of that. For entrepreneurs, that means you have […]


…when you fund a company, it is never a straight line to success. There are always ups and downs, and you have to prepare for that. What’s more, the financial markets and the venture market have huge swings of their own, so you also have to aware of that. For entrepreneurs, that means you have to raise the right amount of money to manage through those ups and downs in your business, as well as those up and downs in the capital markets.


I had the pleasure to interview Matt Holleran. Matt leads Cloud Apps Capital Partners on their journey to be the best venture capital firm in the world in the cloud business application market at the Classic Series A stage. He works closely with entrepreneurs and executive teams to help them build global category leading companies. Matt has 12 years of operating experience in successful business application companies including salesforce.com, 12 years of venture capital and private equity experience, and a highly relevant network. Matt has a BA in engineering and economics from Dartmouth College and an MBA from Harvard Business School.


Can you tell us a story about what brought you to this specific career path?

My entire career has revolved around business applications. It all started more than twenty years ago, when I was at Cummins Engine Company, a leader in diesel engine manufacturing. I was working at the Cummins plant in Western New York as a co-leader of the assembly and test operation.

One day, our big customers decided they didn’t want to wait 15 days anymore. Instead, they wanted their engines in five days. That change broke our production scheduling software. To handle those new lead times, we installed a business application package from i2 Software for plant floor scheduling. That really turned me on the software industry and the power of business applications. So, I went to Silicon Valley and joined a company called Clarify, which at the time was a leader in the customer support software market. That really put me on my career path.

Can you share the most interesting story that happened to you since you began leading your company?

When I was at my prior venture firm, Emergence Capital, I saw a lot of very early stage startups that needed more money than the seed stage firms could provide. They also needed support from people who had walked in their shoes and had a network they could leverage. That is what, at Cloud Apps Capital Partners, we call Classic Series A. What’s really exciting to me is that many of the founders we’ve backed came to us specifically because they vehemently believed in Classic Series A funding. They wanted the kind of capital, expertise and board support that we could provide as a Classic Series A venture firm.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I was at Clarify in the late 90s, I initially started off in product marketing. Although I was in my late 20s and had never held a sales role, Clarify transitioned me into a sales position anyway. One day, I ran to my VP of sales and told him I had just closed a $300,000 sale. He congratulated me and asked for the signed contract. I didn’t have one. The customer had simply given me his word that the contract was on its way. The VP laughed out loud. He taught me that a deal is never closed until you have that signed contract in your hand, because many things can still go wrong along the way.

What do you think makes your company stand out? Can you share a story?

We intend to be the best in the world in the cloud business applications market at the Classic Series A funding stage. We stand out because of our long experience in the market, both as operators and investors. As a result, we have an unparalleled network of people we can call on when looking for partners or executives who can assist our portfolio companies.

Are you working on any exciting new projects now? How do you think that will help people?

We make three or four new investments per year, but we look at about 400 every year to get to those three or four. We are excited about all the investments we make. Our latest is DataGrail, which is in the customer privacy management application space. DataGrail helps companies comply with privacy regulations like GDPR in Europe and Californian regulation CCPA. Companies are using DataGrail to provide their customers with greater transparency around their data. DataGrail can easily surface data internally and from third-party systems and show the customer how that data is being used. That is extremely important in today’s world, where ensuring customer privacy is vital to your success.

What advice would you give to other CEOs or founders to help their employees to thrive?

We recommend that all the CEOs and founders at our portfolio companies implement a system called V2MOM. The system was pioneered by Saleforce.com. It is a mechanism for framing the visions and values for the company (V2), as well as for framing your methods, obstacles and metrics (MOM). V2MOM is super important for communicating to everyone where you are taking the company. It also helps you understand the people who are good fit for the company, as well as define the key priorities of the company. It is the best way to frame alignment on vision and culture fit, as well as on what really need to focus on, both as a firm and individually.

How do you define “Leadership”?

Leadership is about creating a strategy that let’s your company be the best in world at what it does. From there, it’s about explicitly framing the culture of your business and living that culture. That entails listing your core values in order and living those values. It’s also about deeply understanding who your core customer is and aligning everything you do around that customer.

What advice would you give to other CEOs about the best way to manage a large team?

The V2MOM system scales beautiful and I would advise leaders to implement it not just at the executive level, but at the department level, the team level and even the individual employee level. Having a mechanism for a common strategy and prioritized goals and metrics keeps everyone aligned.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My mom. She was a self-made technology executive, and she was also a single mother of three. She inspired me through how she lived her life and how she developed her career. As a result, she opened up many opportunities for me in my life. She started off as a typist and worked her way up to a management position for a company that help bring computer technologies into the book and magazine publishing industry. She was a tech luminary in that field for decades.

How have you used your success to bring goodness to the world?

Business people, and in particular teams of business people, can be much more successful when they are using great business applications. And if people and teams are relying on the right technology tools and the right information, rather than hunches and guesswork, they will be more successful both professionally and personally.

What are your “5 Things I Wish Someone Told Me Before I Became CEO” and why. (Please share a story or example for each.)

There weren’t any big surprises when I started Cloud Apps Capital Partners. I had worked at a growing venture capital firm prior to starting my own, so I pretty much knew what to expect. But I would say that when you fund a company, it is never a straight line to success. There are always ups and downs, and you have to prepare for that. What’s more, the financial markets and the venture market have huge swings of their own, so you also have to aware of that. For entrepreneurs, that means you have to raise the right amount of money to manage through those ups and downs in your business, as well as those up and downs in the capital markets.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I am very pleased to see a revival in real journalism, and I would love to see that continue. Journalism is hugely important for being a check on bad actors — whether in business or politics or society in general — and for providing information that enables all of us to make better decisions. I think journalism lost its way over the last few decades as legitimate publications went out of business and the compensation for journalists declined. So I’m pleased to see paid subscriptions for publications like The Economist and The New York Times on the rise again. I want our best and brightest to once again consider a career in journalism.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Always do your best. That’s all that you can do.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

Chris Hayes, the host of All in With Chris Hayes on MSNBC. He’s a great journalist, and I’m a big fan of his book Twilight of the Elites: America after Meritocracy. He’s doing great work in helping America live up to its values.

How can our readers follow you on social media?

@CloudAppsVC on Twitter, or Cloud Apps Capital Partners on LinkedIn.

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