What Amazon and Microsoft Don’t Teach You: The Anatomy of a Start-Up

What Amazon and Microsoft Don’t Teach You: The Anatomy of a Start-Up
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I was fortunate enough to start my career at two of the most influential companies in tech–Amazon and Microsoft, where I had the opportunity to work alongside some of the brightest minds in the industry. While I can’t think of a better pedigree for pursuing a career in the digital world, each company came with its own unique challenges, perks, and drawbacks. Looking back on my time there, I’ve been able to cherry pick the lessons I learned from each of these tech behemoths and incorporate them into the DNA of my own sales tech startup—Outreach. Since starting the company 3 years ago, I’ve learned several important lessons about being the CEO of a rapid growth startup that simply cannot be learned in a more established, best in class technology company.

The Magic Hat

When Outreach started, we had a total of four employees, me plus three fellow co-founders. There’s so much to do in the early days - product design and development, selling, fundraising, hiring - you end up wearing a lot of hats, or perhaps just one “magic hat.” I came to the team as a product guy but quickly realized I needed to be a sales guy. I went up and down the 101 knocking on every door, I hit the phones to secure meetings, I gave demos. I was a company strategist, spokesperson, sales rep and even SDR. And each of my co-founders wore just as many hats. This is not something you can learn or even appreciate in a large company where everyone is a specialist. In a startup, you have to learn many domains, quickly. And that takes passion, grit, endurance and unwavering commitment to your vision, regardless of how much money you’ve raised.

Which brings us to our next topic.

Funding Is Believing, and Believing Is Funding

As every startup with venture capital fuel in its engine knows—the name of the game is funding. This is a stark reality that growing up in the big leagues doesn’t teach you. They’ve got deep pockets and running out of money just isn’t a concern. As a startup co-founder though, you think about it every day. It’s not enough to believe in your vision, you must get others to believe, too. Enough to put their own dollars behind it. Or, to be one of the first employees to join when making payroll isn’t always a sure bet like it is at Microsoft or Amazon. Raising the initial seed round is the toughest part because you’re going to venture firms with no track record. You’re asking them to believe in things unseen. It’s not for the faint at heart.

As an innovative company with a unique value proposition, there wasn’t much in the early days to compare us to. This is scary to a lot of people. I was selling a vision and trying to get people to buy into how I thought the world would look not just the next year, but five or 10 years down the road. I was essentially selling myself and not everyone was buying. What saved me is conviction. Never doubt your vision, that’s the game changer. If you don’t believe in your company, no one else will. You can’t listen to the naysayers, you can’t be deterred by every “no” you hear – because there will be many “no’s” on the way to “yes.” When others don’t believe, keep believing.

You’re Your Own Creator

One of the toughest lessons I learned, particularly coming out of two very established tech giants, is that as a disruptor, there is no blueprint. Ben Horowitz said it best in his book, “The Hard Thing about Hard Things”. If your product or service is game changing, you’re essentially building the plane while flying it. This opens up doors to questions you likely never considered before, such as, what technology category does your company fall under? Is there one, or are you the pioneer establishing it? If so, you must clearly define it—to your investors, to your employees, to your revenue-driving customers, and ultimately, to the world. This means staying firm to your vision statement when others try to bucket you in with the closest common denominator, and shouting from the rooftops how you’re different from those they want to call your competitors.

Being a pioneer isn’t easy, it’s the road less traveled, so make sure you’re up for the journey before embarking. Once you start down the path of being your own boss, it’s even harder to go back to the top-down rules of the tech giants. But with a powerful vision, relentless execution, and a little luck, it might just take you places you’ve never dreamed before, or you might build your greatest dream into reality.

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