In this episode, I had the opportunity to talk to Will Decker, the VP of Brand and Retail for Plug and Play. The company is known as the most active investor in Silicon Valley. It’s also the “ultimate innovation platform” because it connects the best technology startups with the world’s largest corporations. Will Decker has expertise advising companies large and small on strategy, product, marketing, and business development.

Working with Startups to Create Innovation

I asked Will, “What do C-level executives need to know about how they can work with startups to create innovation?”

He told me there are a couple of things. It starts with having a clear vision around the problem you’re trying to solve. Companies should be able to articulate their core strategy, whether that’s a purpose-led statement, something around their mission, or what they’re trying to accomplish as an organization.

Then it’s a question of build vs. buy. What’s an area where execs think there’s already a solution that someone out there is already building? A solution that lets the company get faster to market and find a better solution that’s more nimble?

Once you do that, Will said, and you articulate a key area, then you can engage with the ecosystem. That’s just the start.

After that, you need to set up a whole culture around working with companies that are not within your four walls. So, this could be impacts to procurement, and how you onboard new companies, and it involves testing very quickly and establishing environments that are set up to test.

Usually, where it ends up, is you’ll focus on speed. How good are you as an organization at going from an idea to launching that idea within your company and for your customers? It’s fantastic if you can do that very quickly. It gives you a lot of nimbleness, and it future-proofs you in the industry.

Those are the primary activities.

As for the output: you’re becoming customers of startups, you’re co-developing ideas, you’re investing, and you’re acquiring with the startup community

The Deal Flow Session

“That’s all great in theory,” I told Will. “But in practice, how do you do that really well?”

Will told me that Plug and Play has gained success by trying lots of different models. The model that’s worked consistently is the deal flow session. Deal flow is a specifically targeted, curated, matchmaking session between a problem area for a large, Fortune 100 company and the startup ecosystem.

It’s critical to bring everything together with a very focused session. A meeting for at least 30 minutes that helps everyone get to know the different companies – the large companies and the startups together.

Over the years, Plug and Play has learned a tremendous amount in terms of making those meetings effective and productive for all different parties involved. 

Common Mistakes

I asked Will about some of the common mistakes he sees CEOs on both sides making. The first mistake he pointed to is the “we can build that” mindset. He put it this way:

“If you’re thinking, that’s great — we can build that — that’s something we’re not going to outsource. The only time that’s not a mistake is when that IP is strategic. If there’s a strategic business moat you need to create around a business process, fine. Own that. But if it’s not, it isn’t worth the complexity and the operational overhead. Find some great partners.”

Another mistake he mentioned is analysis paralysis. Large companies often research and over-research problems, opportunities, and strategies for months or even years before they act. Act sooner. If there’s a way to test something earlier and get feedback and real-world learnings, and then adapt or pivot, do that. Speed is a very common struggle.

To hear Will’s answers to other important questions I asked him, be sure to listen to the whole episode! Particularly, you won’t want to miss the success stories he shared with me, as well as the ways you can connect with Will directly.

Murray Newlands

Murray Newlands is an entrepreneur, investor, business advisor and speaker. He is the founder of the How to CEO podcast and you can read his blog at