How Startup Founders Grind it Out: 5 Examples

The contrarian in me loves stories about founders who fit a different mold and take the road less travelled to startup success. That’s why I enjoyed reading “Grinding it Out” by Ray Kroc, founder of McDonald’s.

Grinding it Out is not a romanticized view of entrepreneurship, rather Kroc’s journey dispels numerous entrepreneurship myths.

First off, he’s not your typical self-made tycoon. Kroc was 52 years old when he opened his first McDonald’s franchise and before the golden arches, his career was riddled with failed and semi-successful ventures.


A McDonald's in Phoenix, Arizona, 1953. 


Not a typical success story, right?

Hollywood wasn’t brave enough to call the movie adaption Grinding It Out, instead opting for a safer title: The Founder. I find the same phenomenon in business writing, there’s a lot of discussion around the founder’s vision, strategy and personality, and not much written about how great founders grind it out.

So, here are some examples of how startup founders grind it out.

1. Sales

Sales is an under-respected skill set in startups (for a great and detailed view about not only sales but how products get distributed, read this from Peter Thiel).

Those of us in B2B know all about the sales grind. Lists, lists and more lists. Cold prospecting, annoying the heck out of people with follow ups. Researching all 2,000 conference attendees before a conference.

Here’s a piece of advice for early stage B2B startups. Don’t think you can automate the grind before you grind it out yourself, sometimes for years.

Grinding is how you move the needle and close that sale you had no business closing.

Learn How Plum.io Improved its Investor Reporting and Relations with Hockeystick.

2. Recruiting

I’ll admit I procrastinated on this for years. I never liked the grind of constantly reaching out to strangers, doing the same interview over and over again. I thought “who has time to go to every networking event just in case?

In a startup you need that person yesterday, which makes it harder to start a recruiting process you know may take months.

Last year I embraced the grind at Hockeystick. I dedicate at least 20% of my time, every day, to recruiting tasks. You know what? I found that I started learning a tonne from even bad interviews. About other companies, trends and people — but most of all about myself.

I’m a believer now.

3. Fundraising

Yes, raising money is a grind but it’s part of every high-growth company. There’s enough said about fundraising already, actually too much.

One aspect of pitching investors which is a grind is constantly getting feedback about your product and business strategy. If you pitch 10 investors and get the same feedback you should probably sit up and pay attention.

But that won’t happen.

You’ll get 10 wildly diverse opinions. 10% of them will be good, you just won’t know which 10%. This is especially grindful (just made that up) because no matter how confident your pitch is, not all of your strategies are fully baked yet either.

When you have more traction this becomes less of an issue.

4. Management

Does anyone actually talk about managing?

It doesn’t make you sound as clever as coming up with a new management strategy. Almost all of the writing on management talks about processes (like Agile) or high-level stuff like giving people more flexibility.

The difference between a process a result is the practice of management.

Organizing your sprints differently? Management means explaining and re-explaining the process every single day until it’s implemented. Decided that a 10:00 am sprint should start at 10:00 am? You get to herd the cats and have the thick skin to tell someone when they’re a minute late.

I’m not saying management is about being a disciplinarian. It’s about backing up that great idea with the daily grind of making it happen. It’s harder than it looks but it works.

When you’re looking for or developing management talent look for their ability to grind it out.

5. Fake it ’til you make it

If your startup is making promises it knows it can keep your vision is probably way too small.

I love the story of how Brian Chesky was the “photograph my home” button for AirBnB. He would literally show up to your house to take photos. Was this process scalable? No. A feature that moved the needle? It turns out it was, in a massive way.

There are a lot of ways you have to grind before you find product-market fit, all of which are non-scalable. Face to face user interviews, A/B/C/D/E/F testing, pivoting — let’s call it pirouetting! — until something starts to work. I’ve seen a lot of founders who quit on an idea before grinding it out. What happens before the pivot is just a warm-up.

Calling it a grind doesn’t mean it isn’t fun. There are many times when you’re building a company that you don’t know how to get to where you want to go. That’s when it’s comforting that there’s always something you can do, something you can grind out. It gets you one step closer to your goal.

As Ray Kroc said, “Luck is a dividend of sweat. The more you sweat, the luckier you get.”


grinding it out.jpgRay Kroc, 1974.


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