Should Entrepreneurs Work Hard or Work Smart?

Matthew Sniff
6 min readJul 27, 2017

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Are working hard and working smart mutually exclusive?

As an entrepreneur, I hear it all the time. Work harder or work smarter. As in, one or the other. Who said these ideas must be mutually exclusive? Why can’t you work harder and work smarter? What’s so wrong about doing both?

Today’s technology entrepreneurs, amidst increasingly competitive and open markets, are being told they won’t survive by working hard alone — they must work smart. I agree. We must work smarter than ever before. But working smart does not have to mean hitting the hay when the going gets tough, waiting until tomorrow to innovate today, or breeding a culture of a lifestyle business at your startup. It’s a startup — it’s not for everyone, and if you’re at a tiny company in its first stages, it’s more of a family than anything to the contrary. If you’re not all in, then you’re probably looking for the quickest way out because it’s not the ride you thought you were in for.

IDENTIFY YOUR COMPETITIVE ADVANTAGE

This post isn’t to say you won’t be able to make it as an entrepreneur if you don’t work hard. Whoever you are and wherever you are at, you need to identify your competitive advantage. At a lot of startups, this very well may be a triple threat founder, you know, the guy or girl who can code, take sales calls, and market/fundraise. Whatever your competitive advantage is though, make sure to double down on it and drive it all the way home. Ours just happens to be our gritty core team who are all willing to work hard, push themselves outside of their comfort zone everyday, and drive value in everything they do. Their smart about their goals, how to hit them, and where to spend their time, at all times. We continually self-analyze and refine the way we work and the processes we put in place. We realize our success is not headcount, it’s how much value we create. To get there on our bootstrapped budget, we must be smart, but, we must also be willing to work like nobody else is willing to.

“Entrepreneurship is living a few years of your life like most people won’t, so that you can spend the rest of your life like most people can’t.”

Anonymous

TOOLS FOR WORKING SMARTER

You may be wondering how we operate in a “smart” way. Well, at our own company we use all kinds of tools to work smarter. For sales we use five9.com to automatically dial numbers and hit area codes of our customers. We also automatically update lead information with activity from inside our platform each day so we know which leads are hot or not. For marketing we use ActiveCampaign for automatic email campaigns to move biz dev leads down the funnel, as well as to follow up with newly onboarded teams. On the dev side, we use Jenkins and Fastlane for CI and CD support. These automatically run unit and listing tests, as well as manage the deployment of our beta and production releases. Github is used for code collaboration and sub-versioning, and Waffle is a plugin we’ve made use of as our kanban board for project management. We use Slack for communication across defined channels; this makes organizing our thoughts, documents, and discussions much easier. For customer success, we use churnbuster.io to automatically collect and notify customers of late payments. For one-off tasks we use the simple CRM wunderlist to keep track of our deadlines, notes, and individual responsibilities. This is just the tip of the iceberg — never have there been so many great tools to ensure the success of your startup — but never has it been more competitive. You must not lose sight of the fact that there is always someone on your heels. You must innovate or subsist and quickly become irrelevant.

TAKING THEIR WORD FOR IT

As of late, I’ve heard quite frequently the case being made that you shouldn’t aim to work very hard because the “best of the best” don’t do it. Similarly, Jason Freid, founder of Basecamp, makes a case for working smarter and not harder. In his book Rework, super lean workflows, scrum methodologies, and agile development techniques are all discussed in detail. The truth is, I quite agree with all of these arguments. These techniques truly do cut waste and bring a lot of value to any organization they are deployed in. However, just because these techniques give back productivity and value, doesn’t mean the extra time you gain should be squandered… especially at a startup. Basecamp is no longer a startup — they’re an organization of almost 100 people and operate with several layers of management. With a startup of less than a dozen people, any extra time is not just extra credit — it’s another one of your competitive advantages. I don’t know about you, but most startup founders I know aren’t working at building a company just to work casually from 9–5 to see where they can go with it. They’re giving it everything they’ve got, and legitimately love what they do. They won’t stop until they’ve achieved true success at whatever it is they’ve set out to do.

BE INTENTIONAL WITH COMPANY CULTURE

Culture early on at a startup is a very fragile thing. You may have heard the phrase ‘culture eats strategy for breakfast.’ Whether you believe this to be true or not, you cannot argue the importance of culture. It sets the tone for how invested your teammates are in your company. Culture could mean everything from whether you decide to provide your employees with stock options, to how much responsibility you are willing to delegate to them, to social events like team lunches or bonuses for achieving goals. How to setup your culture is not for me to say, but I can say that if you are not careful one employee can ruin your whole culture you’ve so tirelessly built. Their negativity or can’t-do attitude is very much noticed by others and you must take action, quickly. At our tiny startup of less than 12 people we want to incentivize each and every employee to act like a team player and not an employee, thus, we provide them with stock options, flexibility, and in return we expect them to be intrinsically motivated enough to hit their own goals. We expect them to be self-starters and initiative-takers. We expect them to seek data-driven answers to their problems, and to always get better at whatever they do. We aren’t looking for people-pleasers, we’re looking for those who want to do whatever they can to drive true value to the company and to themselves.

WRAPPING UP

In conclusion, there are more than enough reasons to continue to work hard and work smart at your startup. There are reasons innovation hubs like Silicon Valley, NYC, and Boston are so far ahead of other, smaller markets. The entrepreneurs in these communities know what it means to have to work hard — otherwise, they might not eat, let alone take home a paycheck. When you’re truly invested and committed to what you’re working on, there is no other option. Until your company is cashflow positive with more than a dozen team members… treat every action, every decision, and everyday like life or death for your company. Nobody will care if you take time every now and then to do what’s best for the company… just as nobody should care if you choose to lead by the example of working hard and smart.

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Matthew Sniff

Tornado chaser, iOS developer, photographer, SaaS co-founder @mapmycustomers