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Guest commentary: I was casually talking with a partner at a local venture firm recently, and he lamented: “We don’t have much luck backing ex-Microsoft entrepreneurs.”

His comment irked me a bit. Not in a, well, I’ll-show-you kind of way. More like: Does this venture guy really think he can egg me on with that crap?

But it did make me think. How much did my six years in engineering program management at Microsoft prepare me to grow a successful business?

Shooting from the hip, it’s a tough call. Internally we’ve all heard: “Ah, this team is like a startup, except it’s at Microsoft.”

Newsflash. It’s not. Not even a little.

For whiteboards, Microsoft people send an email and one magically appears. Startup people head to Home Depot and build them, never mind having a wall to put the darn thing on. And that’s just the first week.

A Business “To Do” List

To start, let’s lay out what it means to build a successful software business. A real software business has basically three components:

  • Sell stuff  (The so called, “top line”)
  • Build and operate stuff (someone needs to want it AND pay for it)
  • Manage money (Make sure you charge more for #1 than you spend on #2)

If you strip away all the hype, that’s pretty much what you’ve got. So, without further ado, here’s the grade I’d assign to the lessons I learned from Microsoft that I am now using in my current startup.

Sell something? You mean charge actual money?

Aaron Goldfeder

A couple years ago, as a wantrapreneur, I had a panic attack when I realized that to lead a business you needed to be able to sell.  Sometimes I ask Microsoft folks if they’ve sold before. They usually mumble something about selling a vision internally or something. Another newsflash.

Selling a vision, a project plan, recruiting… all that soft stuff is totally different than signing up to delight a customer who trusts that your product will deliver the ROI that makes their money worth it.  And then you have to work with them to actually pay you. As in invoice. Money. Deposit to bank.

For the enterprise, this really translates to learning a tradecraft involving understanding a customers business needs, their business case, earning trust and following through–one client at a time. The so called “business guys” are woefully underappreciated in the product teams at Microsoft, and I left totally unschooled in the art of sales.

Selling Stuff: Microsoft Entrepreneurial Training Grade: D


Just Build It

Microsoft is probably still the world’s best company for getting real seasoning on such a wide variety of technologies. For good reason, no other company attempts so much.

To be fair, maybe Apple is now there too. If you’re lucky to get some good mentors and teams, you really can get super deep on a lot of technology, especially if you hack some stuff on the side.

But building stuff is one thing. Building stuff that people love AND will pay for is another. This means a whole other level of depth is required in understanding your varying users and your customers.

And at Microsoft you are rarely taught that users aren’t necessarily customers. I’ve found it humbling in how much I’ve had to learn quickly to fully deliver product at EnergySavvy. As my co-founder Leo Shklovskii likes to point out, sometimes 80 percent is only halfway done.

In fact, the whole business vs. product thing is often wildly conflated at Microsoft.

Product General Managers are regularly referred to as running a business or something similar. They aren’t. They are usually engineering managers.

Sales is something in a whole other organiation. Marketing’s another.

In fact how many people at Microsoft really own a P&L? Five? Ten? How often does a sales rep actually talk to a developer?

Building Stuff: Microsoft Entrepreneurial Training Grade: B+


Money. Money. Money.

It’s almost unfair to even give a letter grade in the category of managing money. Yes, I managed a multi-million dollar budget at Microsoft. Did that have much bearing whatsoever on my ability to manage money for our business? Nope.

Manage Money: Microsoft Entrepreneurial Training Grade: C+


It’s who you know

There are at least two additional key benefits that a solid Microsoft education can also give you: networking and management skills.

Networking: Folks outside of Microsoft love to point out that a good portion of Microsoft experience doesn’t matter outside of Microsoft (e.g. no one cares about ship-its, much less your ability to sit in meetings all day without offending anyone per your next promo goals).

That said, the pedigree is respected enough that you can often get people to take your call, which means you can build a great network. The extended Microsoft network has been an incredible asset to us for which we are exceptionally grateful.

Management: If it’s one thing Microsoft has in spades, it’s management positions and frankly some great managers. I was lucky enough to have both and as a result learned a lot about team management. Those skills are finally coming in handy now that we’re scaling up. It didn’t matter much at the very beginning though!

Continuing Education: Microsoft Entrepreneurial Training Grade: A+


So can ex-Microsoft employees make great entrepreneurs? The truth is I only care in as much as I’ll always have love for Microsoft.

And, I do think it’s probably one of the best places in the world to get foundational experience.

For myself though, I can only look at what I learned, the folks I met via the Microsoft network and how I need to respond to offset my own shortcomings and amplify my strengths.

As I explained to the venture firm partner when he made that comment, we’re not out to prove anything to anybody. We’re here to grow a great business and that’s pretty much it.

Summary Score: Solid B

Aaron Goldfeder is the CEO of Seattle startup EnergySavvy. He is a former Principal Group Program Manager at Microsoft where he was a key leader on Internet Explorer, Windows XP, Local Search and a Microsoft Internal Cloud Services Platform.

Previously on GeekWire: Does working at Microsoft really turn your brain numb?

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