The “Messy Middle” of Big Companies

By Micah Rosenbloom, Managing Partner

I recently had the opportunity to interview Scott Belsky about his new book, The Messy Middle. It’s an outstanding handbook for founders and startup employees to navigate the challenges of building something from nothing. But in addition to being a successful startup founder and seed investor, Scott is also an executive at Adobe, a 36-year-old software giant with 18,000 employees and a $120B market cap, and it turns out the principles from his book apply in that context as well. During the Q&A of our book launch event, a few big company employees asked interesting questions, and we thought this lightly-edited transcript might be of use to folks trying to find their way in a FAANG company.

How can experience at a big company help an entrepreneur?

• Well, I think that understanding how big companies work is really helpful as an entrepreneur. For instance, M&A in some big companies can be like feeding a domesticated lion. Where, if you throw a piece of meat in the cage, the lion will just look at it and ignore it and just go back to whatever it was doing. You kind of have to tease the lion with the piece of meat, and kind of flick it and annoy it to the point where the lion’s like, “What the hell?,” and just eats the meat.
• I think that understanding how, in big companies, everything is about cadence. If you don’t advocate for something strongly, there’s a real powerful regression to the mean. So everything will just return back to what the obvious things are to focus on. And someone has to actually keep making noise and annoying the team to consider anything new to the point where it’s just like, “Okay, fine! Let’s just discuss this. Let’s make a decision in this meeting. We’re in or we’re out. No more of this nonsense, constantly mentioning this. It’s just annoying.”
• Maybe that’s the healthy immune system in a big company that helps it stay focused on the bottom line, afloat, and productive. And I think working within a larger company gives you some exposure to that. Because as a founder, working on something you’re passionate about and something you think is a no-brainer for the big company to consider, you’re always like, “What the hell’s wrong with them? This is so freaking clear. Like, how could they not be working with me? How could they not be taking my meeting?” You kind of have to have that sense.
• Early in your career there’s something to be said about having good managers that you can learn from. And learn how they give you feedback, and how then, you have to give other people feedback. And some of those processes are helpful as well. And some of them are destructive.

How should a person with entrepreneurial leanings manage the messy parts of mega-corporations?

• You have to set a bit, in many different ways, when you take over an organization as a leader. For example, I created and keep what I call an elephant list. And anything that I feel people aren’t saying or issues that are too sticky to address and reconcile, I put on my elephant list. And I come back to that elephant list repeatedly. And I also force my team to talk through them. And they’re difficult, because they all are questions around, “Why is this in that org when it should be in that org?” If left unanswered, these questions add to the organizational debt that slows an organization. So, I’ve cast myself as an instigator, for better or worse, where I’m just keeping that elephant list and pushing it forward.
• I try to get people aligned with vision. In a big organization, it’s all too easy to lose track of what you’re doing and why you’re doing what you’re doing. But when you have a very clear vision, often times driven by design so people can share the same visualization of where they are headed, you can get people aligned without adding too much process. That feels like magic.

How should founders think about corporate development?

• I think that you need to have a corp dev. contact and an internal product leader advocate, for every opportunity. And if you have one without the other, it’s a little hard.
• For the acquisition of Behance, we had a four year courtship that involved at least one other acquisition opportunity, two partnerships, and the fourth interaction was the actual acquisition. And I kept this going, not only with Adobe, but with a few other companies. I didn’t even think about it as courting potential acquirers. I just wanted these folks to know what we’re doing so that if they ever made a partnership with a company that provides portfolio display or whatever, that they would come to us. And actually, LinkedIn ended up coming to us, and we powered portfolio display on LinkedIn.
• I would forward investor updates with edits. I’d obviously take out certain things, but I would make it look like the actual forward. And I would just say, “Hey, FYI, we just sent this out to investors. A ton of progress. Amazing team. These are the things we want to do over the next few months. Love to work with you.” That kind of thing. And sometimes they would never reply, but it would keep us on their radar.
• I think it’s healthy to build relationships constantly with anyone in your ecosystem that could potentially be a partner or an acquirer. Because when you actually decide any of those things need to happen, you don’t want to start that relationship from square one.