What I Fear Most As a Founder

I have many fears as an entrepreneur. Here’s why that’s not a bad thing, and why you shouldn’t be afraid of fear, either

My name is Alex, and I’m scared. Here’s why that’s not a bad thing, and why you shouldn’t be afraid of fear, either.

This is part fourteen in our ongoing series, Journey to $100K a Month. Earlier posts can be found here.

I was watching an entrepreneur give a talk about what it takes to build a successful company.

“Being bold isn’t enough,” he proclaimed with enough enthusiasm to make the whole room lean in to listen.

He narrowed his eyes and pointed at his listeners.

“You have to be fearless.”

The room was dead silent as the audience absorbed this seemingly profound lesson.

The speaker is a brilliant, successful guy who’s founded and sold two startups. I’ve learned a lot from him and I admire him tremendously.

And I have no doubt that he is, in fact, fearless.

But if what he says is true, then Groove doesn’t stand a chance.

As an entrepreneur, I fear a lot of things.

When things got bad and we were close to death, that fear nearly drove me to the brink of complete emotional breakdown.

When things are good — or even great, as they are today — that fear refuses to be suppressed, and I still sometimes lose sleep, dreading (or sometimes even expecting) the worst case scenario.

And through it all, while that fear has nearly cost me my sanity on more than one occasion, I’ve learned to love it.


Because they make me a better entrepreneur. Every one of my biggest fears drives me to ensure that I never have to see them come true.

I hope you’ll forgive the self-indulgent post, but my goal isn’t just to share my own fears. It’s to demonstrate that the “fearless entrepreneur” stereotype doesn’t apply to all of us, and yes, you can be scared absolutely shitless, and still be successful.

I hope.

The fear of letting down our customers

I started a business because I believed that I could be good at it.

But I started this business — a customer support company — because I believed that I could help other small businesses become successful by getting really good at support.

To date, more than 1,000 customers have bought into that vision. And I think we’re doing pretty well at achieving what we set out to do.

But what if we fail?

What if we suffer a technical issue that costs our customers dearly?

What if we fall behind on innovation and allow our users to be lapped by their competitors, armed with better tools?

There are fates worse than going under, and hurting the people who entrust you with their business is the most painful one I can think of.

How it drives me: Our customers are the center of our world, and every business decision we make revolves around making them more successful. It sounds like marketing fluff, but it’s truly changed the way we run our business for the better, and it all came from being scared to let our users down.

The fear of letting down our investors

We didn’t raise a big venture round, but I did take some early cash from a few angel investors that I trusted deeply.

Before Groove reached Product/Market Fit, before we had paying customers, before we had a talented team, before we had any semblance of a real business, our investors believed in us enough to put their hard-earned cash behind our dream.

I’m incredibly grateful for their help, and we wouldn’t be where we are today without them, but even more than that, I’m scared to let down the only people who were so into Groove that they willingly put their skin in the game, knowing that as an early-stage startup, the odds were stacked high against us.

I’m scared that I might someday have to tell them that they were wrong for believing in us.

How it drives me: While making our customers grow is essential to making Groove successful, we can’t help anyone if we run out of money. This fear has led us to take monetization and pricing very seriously, testing and iterating for months to get to a model that finally worked.

The fear of making a bad product decision

This is one of the fears that we’ve actually had come true.

In the early days of Groove, we made some huge product fails and it cost us six months and $50,000, nearly killing the company.

Seeing the fear realized, and then fighting through and emerging on the other side didn’t make the fear go away. Instead, I’m now even more worried about huge product missteps.

This fear has spurred us to make massive changes in the way we develop. By running lean and building iteratively, we hedge against the possibility that we’ll have to go through the same debacles again.

Still, like any business, we’re vulnerable.

The fear of past decisions coming back to haunt us

Since the start, we’ve been a remote team. We have folks all over the world working on Groove, and we keep in touch throughout the day using a variety of tools.

But what if that was the wrong choice?

What if an in-house team really is more effective?

What if our culture were stronger?

Would we be growing faster?

I wonder how much — if anything — we’ve given up by not focusing on having a headquarters where everyone works side by side.

How it drives me: In practice, the decision is pretty much irreversible, and the fear surrounding that has led us to putting a ton of effort into working together better. We’ve learned a lot in that regard, and I’ll be writing about it in the future.

The fear of being consumed by my work

Like most founders I know, I can be obsessive.

Not “60 hours a week” obsessive.

More like “forget to eat, sleep and acknowledge the people around me” obsessive.

Ironically, I have to work really hard to not work too much. And I do make that effort, for the sake of my own health, my personal relationships and my ability to run the company.

But I’m scared of slipping. Of an impending feature launch or some other “crunch time” deadline dragging me into the rabbit hole, and of my own obsessiveness taking over and never letting me out.

How it drives me: This fear forces me to take time away from work. It feels strange to say, as I never thought I’d have to drag myself out to go surfing, but I do it fairly frequently, and I’m glad I do.

The fear of falling out of love with Groove

A lot of very smart, hard-working people build companies opportunistically. They see a hole in the market, regardless of how well they know the market, and they fill it. If they’re savvy, they often sell fairly quickly and make out with a nice payday.

I’m simply not capable of doing that.

Groove is a labor of love for me. If I didn’t love working on this company every single day — the product, the marketing, the blog, the customer support — I wouldn’t do it.

There are a lot of far easier ways to make a living than building a software startup, and they’re certainly tempting.

But Groove is what I love. And right now, I want nothing more than to make it my life’s work.

While I have no reason to believe that it will (see: The fear of becoming obsessed with my work), I’m terrified that that might change.

If I ever fell out of love with my job, I hope I’d be smart enough (and self-aware enough) to hand the reins over to someone who can ensure Groove’s success. But what if I’m not?

How it drives me: This was a lot harder in our early days, before we had customers telling us every day about the impact Groove was making on their businesses. I had to remind myself daily (in fact, I had a calendar notification for this; I literally reminded myself to remind myself) why I got into this. I’m driven to make Groove successful, so that even if I do fall out of love with the work, the company can go on without me.

How to apply this to your life and business

It’s easy to look at most of the business content out there and conclude that the people writing it are fearless warriors who don’t flinch in the face of danger.

That’s not the only way to succeed.

It’s okay to be scared. I know I am.

The key is to harness your fears; don’t hold crippling fears, but instead turn them into driving fears that will help you avoid the things you’re scared of, become a better entrepreneur and grow your business.

I challenge you to do this together with me: leave a comment below about your biggest business fear, and how you’re using it — or plan to use it — to achieve your goals.

Grow Blog
Alex Turnbull

Alex is the CEO & Founder of Groove. He loves to help other entrepreneurs build startups by sharing his own experiences from the trenches.

Read all of Alex's articles

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