Embrace The Grind

Or why a startup can be sexy from afar but mundane up close.

Uninvent helps startup founders with the most important factor in their success: their team. We help founders manage their own motivation, productivity, health, and relationships with co-founders. We’ll discuss hiring and managing great people, building a strong culture, and keeping people aligned and working on the right things. See the series overview in Welcome to Uninvent.

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“Many a young person tells me he wants to be a writer. I always encourage such people, but I also explain that there's a big difference between being a writer and writing. In most cases, these individuals are dreaming of wealth and fame, not the long hours alone at the typewriter. You've got to want to write, I say to them, not want to be a writer.” 
— Alex Haley

"To achieve your dreams, you must apply discipline, but more importantly, consistency. Without commitment, you never start, and without consistency, you never finish." 
— Denzel Washington

“A lot of people say they want to be great, but they’re not willing to make the sacrifices necessary to achieve greatness. They have other concerns, whether important or not, and they spread themselves out. That’s totally fine. After all, greatness is not for everybody.”
— Kobe Bryant

Theory, meet my friend Reality

After working all weekend, you succumb to the temptation to check Instagram. You digitally stalk a startup founder acquaintance who raised his seed round when you did 18 months ago. You can’t tell how well his startup is doing, but you can tell he’s having more fun than you.

You watch several Reels of him partying at nightclubs with other startup founders and venture capitalists at last week’s Art Basel Miami. Now he’s in New York, launching his product at TechCrunch Disrupt. He then heads to South by Southwest in Austin to speak on a panel about raising a seed round. He also launched a podcast with another founder, but you decide you can skip it.

You compare his week to yours. You spent ten hours interviewing candidates for an open marketing position, wasting nine of them since you knew each one wasn’t a fit after three minutes. You demoed your product to a dozen potential customers, all of whom ghosted you when you requested follow-ups. You had two tense one-on-ones with team members where you had to deliver harsh performance feedback. You still have 100 unread Slacks to plow through.

This week’s calendar looks very much the same: no launch parties or conference keynotes, just back-to-back interviews, customer pitches, one-on-ones, and team meetings. You’ll answer a hundred emails, close 25 support tickets, and track down dozens of references for candidates you are trying to hire. You reserved an hour each day for “thinking work,” but you know they’ll get absorbed by team members who need talking off of whatever ledge they’ve shuffled onto.

OK, your life is far less glamorous than your friend’s, but the good news is that you are probably more on track to create a successful startup. You are willing to Embrace the Grind.

Grinding it out

The first couple of years at a startup are a scrum where you just pile onto whatever it takes to build a product, get a few customers, and hire the people needed to make that happen. Good for you if you graduate from that phase since most startups never do. You then transition to a company-building phase where you settle into a steady rhythm of spending your days trying to make progress in a few ways:

Pitching and selling

Landing a few happy customers is a nice milestone, but it’s only a toe in the water. Now, you have to build a machine to make sure prospects know about you, get them into your pipeline, and get them to pay you. Selling involves a great deal of time, repetition, and rejection. Don’t be surprised if, in a week, you cold call 50 prospects just to get a handful of meetings, most of which will end in rejection. Or you might spend the week working the booth, pitching prospects at an industry trade show. Think Columbus Airport Hilton, not Art Basel Miami.

Recruiting your team

When you are growing, you are almost always filling new positions or backfilling for people who quit or you let go. Filling a single position might require dozens of hours of interviews and reference checks, with an executive hire requiring even more. You might spend 10 to 20 hours per week recruiting, and if a hire quits or doesn’t work out, you have to start over from the beginning.

Managing your team

If you are in a senior role, your days will fill up with staff meetings, project meetings, training new hires, and one-on-ones. Some of these discussions can be draining and emotional since they involve disagreements and delivering tough feedback. 

Soothing customers

Even after you get to some level of product/market fit, you have to stay close to your customers to understand how they use your product, what enhancements they need, and what value propositions and messages resonate with them. A customer can go from happy to unhappy very quickly and they’ll cancel you if they aren’t getting value. You’ll meet lots of customers, possibly traveling to the larger ones. Some of these meetings are hard to delegate since customers love meeting founders.

Operating and financing the company

Close the books. Appease the landlord. Pay the taxes. Issue stock options. Prep for the board meeting. Although you will rely on your team, firms, and software to manage your operations as much as possible, you are always responsible for the final product. It’s your signature on the documents.

In other words, much of your time is spent on work that’s repetitive, difficult, boring, and often ends in rejection. You never have enough time to do all of it, so you’ll likely try to solve that by cramming activities into your calendar until it looks like a brick wall of meetings, sometimes in 30-minute or 15-minute intervals.

The days blend into each other. Soon, the weeks and even the months start to fly by as you bounce from one thing to another all day, every day.

Welcome to “The Grind.”

Now, sure, you knew that you wouldn’t spend your time partying at Art Basel Miami with the founder from our vignette (although, yes, such founders exist). But you may not have known how much of your day would be mind-numbing and repetitive. You thought you’d be Willy Wonka, but most days you are more like an Oompa-Loompa.

The best startup founders master the grind and don’t let the grind master them. You can keep a few things in mind when you think about yours:

Don’t start a startup if you don’t want to grind

You wouldn’t become a surgeon if you didn’t want to spend all day stitching people up. You wouldn’t become a musician if you hated rehearsing and recording studios. So don’t become a startup founder unless you want to spend all day every day grinding with your customers, product, and team. 

The grind isn’t just an unfortunate byproduct of the job. It’s not just something you do until your startup gets some traction. The grind is the job. It’s what you do. And as your company grows, the grind can get tougher before it gets better.

Even founders who have taken their startups public and have nine- or ten-digit net worths still spend much of their time grinding on staff meetings, one-on-ones, interviews, investor meetings, and customer meetings (although traveling to those meetings in a private jet somewhat eases the burden!)

No, you shouldn’t expect to enjoy every minute of the grind — it’s called “work” for a reason — but you have to enjoy the day-to-day rhythm of selling, recruiting, managing, and inventing. You can’t look at the grind as something to endure until you get to the “fun part.” It has to be the fun part.

But know that the grind will evolve

Although you shouldn’t start a startup if you don’t want to grind, take solace that you aren’t signing up for a “Groundhog Day” existence where every day is identical to the last until you slouch toward retirement. As your startup evolves, your grind will, too.

The grind is like a spiral staircase. You’ll cover the same ground again and again, but you’ll do it from a higher vantage point. Instead of pitching every customer, you’ll help close the most promising ones. Instead of being the first person to interview a promising candidate, you’ll do a final sanity check interview. You’ll go from pitching dozens of potential investors to updating the handful who invested in you (at least until the next round).

This constant progress is why startups can be great compared to larger companies, where the years can blend together because the grind is more static. You can often look at how you spent your time today and reflect that it’s very different from a year ago. The downside is that if your startup isn’t growing, you and your team will be frustrated by a lack of progress, and you’ll struggle to hold the team together.

Don’t get lulled into complacency

The grind is hard work, and most of us were raised to believe hard work pays off. After a hard week of grinding, you might go home assuming you are a week closer to success. You might not be. Grinding doesn’t help you if you grind on the wrong things.

Grinding on your product gets you nowhere if you are solving a problem that isn’t urgent for a well-defined ideal customer profile (ICP). Grinding on customer calls doesn’t help if you use the wrong value proposition, messaging, or pricing. Grinding on managing your team doesn’t help you if you have the wrong team.

The grind can become mesmerizing and hypnotic, where you go on autopilot and start going through the motions. Be careful when you feel that happening. Always ask if you are grinding on your most important priorities. We’d all love to live in a world where hard work produces results, but it doesn’t always. It’s necessary but not sufficient.

Focus on your priorities

Working on those right things means going on the offensive and ruthlessly controlling your time. Don’t let the tsunami of meetings, interruptions, and an overflowing inbox turn your days into whack-a-mole, where you try to smack down every random task and problem that pops up, going home frustrated that you’ve made no progress on your top priorities.

For example, if your startup suffers from a lack of leadership in Engineering, spend ten or more hours per week hiring a new VP of Engineering. If you have a churn problem, devote time to working with customers to diagnose and solve it. If you are fundraising, scale back anything that’s not a critical path to closing the round.

And don’t let the day-to-day grind distract you from the “deep work”¹ that requires time, focus, and discipline to complete, like working on your product, creating a sales playbook, or revamping your messaging. 

It’s easy to look at your overflowing calendar and think, “Where do I make time for that?” but where do you think that calendar came from? You created it, and you can change it anytime you want to. It’s your calendar. It’s your company. 

Find a fast but sustainable cadence

If you embarked on a weeklong cycling trip, you’d plan a cadence that works for you. Maybe you’d bike in the early mornings to avoid the heat and recover in the afternoons. Maybe you’d break the day up into two segments of riding with a long lunch in between. Maybe you’d alternate the hard days and easy days. Startup grinding is similar.

Some founders try to stack all their staff meetings on Monday, leaving the rest of the week free for 1-1s, customer calls, and individual work. Some like to get up at 6 am, get a few hours of deep work done, work out, and then go into the office. Some like to reserve a day a week (even if it’s Saturday) for “deep work” that requires creative thinking, coding, or writing. Experiment until you find what works for you.

Hire for your weaknesses

At an early-stage startup, you’ll spend much of your time on things you don’t like to do and might not be very good at. You might have to join customer calls even though you are an engineer with little experience pitching prospects. You may not consider yourself a great recruiter, but find yourself in Interviews and reference checks all day. You’ll spend time outside your comfort zone, which leads to rapid learning and builds confidence.

But there is a difference between having a challenging job and having a job you hate. Although you should expect to regularly take on difficult and uncomfortable work, if you dread every minute of every day, you might be in the wrong role, or you may need to tilt your hiring toward people who will take over areas where you aren’t as strong.

Although you should hire the positions your business needs, you can steer your hiring to make up for areas where the founders have less interest and experience. If you and your co-founders are engineers, you might accelerate some of your sales hiring. If you detest finance and operations, you might bring a Head of Finance a little earlier than you otherwise would. 

Just be careful you don’t go too far in the other direction. Some founders make the mistake of losing touch with their business after hiring people to take some of the load. Don’t stop interviewing candidates just because you hired a recruiting manager. Don’t lose touch with your customers after you’ve hired sales and support reps. You can never stop being an expert in your business.

Gamify the grind

You grind to get results, so always ask if you’re getting those results and getting better at getting those results. As you interview candidates, experiment with different questions to see which ones give you the most insight into candidates. As you pitch customers, test different messages and techniques. If it takes ten meetings to convert one customer, ask how you can do it in five meetings. Experiment until you get there. You might not feel the momentum from day to day, but with weeks of compounding improvements, you should see steady progress.

The obvious benefit is that it will improve your startup’s results, but continuous improvement has a less obvious benefit: your grind will get more fun and fulfilling. You’ll feel your skills level up like in a video game. You’ll discover new talents. You’ll gain a feeling of satisfaction and momentum.

Bring this spirit of continuous improvement to your team, too. Share tips and tricks, like which messages in cold emails get the best results. Write down playbooks that work. Train new hires on the most effective tactics your team has learned for closing deals or evaluating recruits. Or even better, have them train each other.

You don’t want your culture to feel like a white-collar purgatory out of Office Space. It should feel like a sports team, where you know what you need to achieve, train for high performance, support each other, and share the rewards. This won’t guarantee you’ll succeed, but it will improve your odds and will help with the next we’ll discuss: “Don’t Burn Out.” (coming soon)

1. The excellent book Deep Work by Cal Newport will give you tools and techniques to find the time and discipline for deep work. Newport also does a great job explaining why “deep work” is so valuable yet so hard to prioritize.