What's actually risky about creating your own thing

If there’s a pocket of tech entrepreneurship one can inhabit, I’ve done so. Traversing the entrepreneurial world showed me something I never expected to see, too.

I started my career at Google, working as a tiny grain of sand on the massive beachhead that is Mothership Googs. Then I worked for a tiny startup as employee number 12, where I built my first team of creators. Then, I joined HubSpot, which was right on the cusp of going public and expanding globally. Finally, I worked at a venture capital firm that invested in tech startups.

I even spent a couple years on my own doing client services FOR entrepreneurial organizations, crafting and hosting podcasts and video shows, advising on brand strategy, and even coaching a few executives on their public speaking. Today, I run Marketing Showrunners, a media company covering the movement of brands making original series.

Big to small, products to services, in-house to supporting services, through to today, running my own organization — I saw and did a lot. I’m grateful for it all. But the one thing I’m most grateful to have learned is the only reason I can do my own thing today. Because I’m simply NOT a risk-taker.

I learned that entrepreneurship is about removing risk, not taking bold risks. I learned that doing your own thing doesn’t require you to do anything crazy at all.

Sure, you find the occasional mad scientist or bold venturer who decides to leap with two feet from the day job to the new project, but those were the exception, not the rule. And honestly? Those rarely built successful organizations. The vast majority of the time, I witnessed the opposite: entrepreneurs and creators who mitigate the risk.

Nowhere was this more evident than my time in VC. The partners at NextView had invested in some 35 businesses when I arrived. By the time I left, that number was closer to 50. I was blown away to see that each founding team was careful and methodical about proceeding carefully and methodically. They’d conduct listening tours, talking to prospective customers for months on end — even after they’d spent years working in the industry they aimed to serve. They’d launch endless tests, measure results, reassess and gut-check assumptions, then proceed again — not by sprinting, but by stepping.

When it was time to leave my in-house job in VC, I didn’t rip the cord. I worked for a few months from 7 to 9 (AM and PM) on my podcast and my public speaking businesses. Then I moved into a part-time role at NextView until I had some more proof and some revenue through my own things.

I eased forward, and the easing continues through until today.

The popular story we receive about entrepreneurs is that they’re visionaries who take bold risks. In reality, they don’t see the future, but rather see the present more clearly. While most of us use lagging indicators like best practices and conventional wisdom, they hone a better sense for what is REALLY happening in the world. Talk to a founder about why their business should exist, and it’s clear: They see it as logical, inevitable, almost predictable.

They never seem to make any giant leaps at all.

But doing your own thing does contain risk. It’s just not the risk we’re handed in the cliche stories.

The real risk of entrepreneurship is this: It’s all on you.

You make the decisions. You build the product, the service, the process, the team. Nobody is there to tell you what to do — no quarterly business reviews, no bosses, no all-hands meetings. It’s about conviction, not consensus — your conviction.

The real risk of entrepreneurship is about ownership and accountability.

Done right, a great creator or founder de-risks the business. But regardless of how certain or uncertain the results may be, it’s still entirely up to you. That can feel entirely too risky for some.

But.

If you’re okay with that level of accountability, and if you crave more ownership, then maybe starting your own thing is indeed for you.

Never let the popular story of entrepreneurship stop you from starting. It’s not about taking massive leaps of faith in yourself. It’s about putting in the work to ensure what you’re doing is warranted. When it seems inescapably logical that your project or your business must exist, that the world needs it, then the lone risk remaining is this: Do you want to be accountable for delivering?

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