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startup-shutterstock_117564307Why do Microsoft alumni struggle at startups?

This clearly isn’t true of everyone who walks through the halls of Microsoft, but it holds true for long-time employees of many enterprise organizations who venture into the startup world. I’ve seen former employees of Microsoft, IBM, Oracle, even Amazon and Google, struggle at early-stage companies.

Why is that? As a former Microsoft employee myself, I see several reasons:

windowsmicrosoftbuilding1. You are no longer at Microsoft

Your prospects don’t automatically answer the phone when you call. Suppliers and vendors don’t automatically give you the lowest pricing for the chance to work with you. Your market-leading advantages are largely gone.

2. You no longer have Microsoft resources

Things once taken for granted – administrative support, in-house legal counsel, budgets, co-marketing partners that work at the same company – aren’t surrounding you any more.

3. You are naked

Accountability is heightened. You can’t hide behind complex organizations and rapid reorganizations. You make the number or you don’t.

4. You are no longer, by definition, diversified

This also means you don’t have a safety net. At Microsoft, that safety net was often Windows and Office. I worked at MSN for my brief time at Microsoft. We didn’t make money. But Windows and Office did. Thank goodness.

5. The partner ecosystem no longer exists

Nor does the enormous in-house sales team with deep, existing relationships to nearly every company in the world. Not that leveraging this partner ecosystem at Microsoft or any big company is easy, but at least it exists. In startups, you start with nothing.

6. Your runway to success is much shorter, and not nearly and neatly funded

Matt Heinz. Photo via Erynn  Rose.
Matt Heinz. Photo via Erynn Rose.

Without the safety net of a larger organization willing to bet on new initiatives, put-up-or-shut-up time comes much more quickly. Executing on that without the resources you’re used to is extremely difficult.

Lack of these conditions, of course, doesn’t spell an excuse for lack of performance. Most businesses face these challenges daily. Sometimes, it takes longer for big-company veterans to make the necessary adjustments.

The exceptions — the big-company people who do well and thrive in startups — are often those who see the above challenges not as an obstacle, but as an opportunity.

Not as barriers, but as a worthy challenge. Not as demoralizing, but exciting and electrifying. Not depressing, but motivating.

I would love to hear thoughts from Microsoft and other big-company alumni on this one.

Matt Heinz, a frequent guest contributor to GeekWire, is president of Heinz Marketing, a Redmond-based sales & marketing firm. You can connect with Matt via email, TwitterLinkedIn or his blog. A version of this post originally appeared on the Heinz Marketing blog. 

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