Great Missed Expectations

Several times in my career, I’ve excitedly joined up with a partner — usually technically adroit, often visionary, always inexperienced. Each time, it seemed a natural fit. We were complementary — I brought a wide variety of tech-marketing and business skills, and most important, experience. And we got along really well. So why didn’t it work out?

The simple answer is . . . missed expectations.

Rushing to the altar (startup/wedding analogies are cliché, but true), partners rarely take the time to share their vision, sort out their roles, and agree to a process. (What, you haven’t discussed your childrens religion? How about whether you even want to have children?)

Here are a few missed expectations I’ve experienced:

I had raised more than $30M over the course of several companies. Co-founder’s expectations: I would make a few calls, and funding would come flooding in.

It never works that way — even entrepreneurs that generate home-run returns to VCs will walk a hard path to funding their next idea. Money-raising takes dozens (if not hundreds) of pitches, six to twelve months at best, and more likely, years. Especially these days. But we never talked about it. I wrongly assumed that the founder understood the game. In fact, I thought we were cruising along just fine.

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The co-founder had several successful products under his belt. My expectations: He would deliver the product on time and under budget.

Well, that would be great. Truth is, it hardly ever works that way. (Why am I always surprised by this?) In fairness, fashioning great technology that has never been done before is hard. Often, it depends on invention. Ever try to plan an invention? But even taking into consideration all the Laws of Software Development, things go wrong. They take longer. They need to be redone. Meanwhile, I’m making commitments to customers, or investors, or the media. And, I’m embarrassed.

But it became such a touchy subject, we couldn’t talk about it. (You know, just ignore it and pretend it doesn’t exist — like that Giant Squid in the Kitchen.) The lesson again: communicate. Doesn’t matter if your company is just two people, meet weekly — formally, same time each week — and revisit the schedules and goals. Above all, be honest.

I’ve served in Bus Dev, Marketing, and Corporate Development roles. Co-founder’s expectations: I would do all the things the co-founder didn’t want to do.

This actually wouldn’t be bad — I’m not the coder, or the chip designer, and it’s always better, IMO, when founders are sufficiently complementary that they stay out of each others’ sandboxes. But it can easily erode when there’s insufficient trust. In the course of going my about the “˜mundane’ business and corporate-development activities, co-founders invariably leapt into my sandbox. And when founders start to second-guess each other is when things can deteriorate.

Which is why I emphasize putting together a Business Plan. It’s not so much about crafting a document, as articulating exactly what we’re going to do. Technical founders are especially good at hand-waving how to make money, because “˜great products always do.’ But working on The Plan forces the conversation, and the drill-down.

Typical issues surround the business/revenue model, IP protection, partnering strategy, and the pyrophoric distribution of equity (Investors are going to get how much? Why are we giving this new hire 10%?). I’m not suggesting that my view was the only view — chances are, the founder knew his/her space well, and had some pre-conceived notions about go-to-market strategy, and what partnerships/alliances to forge. I only point out that it’s imperative to devote time — early on — to these potentially explosive topics, to avoid a breakdown in your relationship.

Much as I’ve sworn to avoid these and other missteps, it still gets down to a question of “˜fit.’ The right roles at the right times, a healthy, collaborative working partnership, shared passion and dedication to the project and the vision. Isn’t that what we all want out of entrepreneurial life?

Which is why I continue the quest — for the partner, gig, and team that needs me as much as I need them.