4 sacrifices founders make, but shouldn't

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Last week I deep dived Calendly. The $3B scheduling giant, taking the headaches out of meetings.

In just under 10 years, Calendly went from not being able to afford payment integrations to over $270M in ARR and a $3B valuation.

Click below to see how Calendly has scaled to process over 10M users and get actionable tactics you can use to replicate their growth.

4 common sacrifices founders shouldn’t make, but do (including myself)

It’s Saturday morning after a busy week of putting out customer fires. You know those weeks where nothing gets done other than fixing issues. Super tiring.

But you’ve been looking forward to some free time to work on the business this weekend - there are still things to be done for next week that you couldn’t get to.

You sit down at your desk, coffee in hand, when boom the invites start flooding in. Your mom wants to go for brunch. Your one friend wants to play some football. Your friend group wants to grab dinner and drinks. And then your partner walks in asking what do you want to do today.

Your body locks up. Everything goes silent.

Your heart and your brain enter the Supreme Court of what to do. Putting forward crisp arguments. Smashing each other with hammers of facts.

And then it’s time for the judge to decide.

What will you do this weekend?

Now for most people, this probably seems odd. What’s the conflict? Why work on the weekend? Or at least why not just work after the fun of the weekend?

But founders are different. And often this means making hard tradeoffs. They have to make sacrifices outside of work that most people wouldn’t. They have to become comfortable with saying no to many things. And it sucks sometimes.

But it’s done in pursuit of a mission you and me as founders feel compelled to pursue, even when sometimes we make the wrong decision.

Here are some of the most common sacrifices and tradeoffs founders make and my take on ways I’ve found to handle them.

Partner, friends, and family time

This is often the hardest one to deal with. And can cause a tonne of stress (at least for me it does).

Of course you want to spend more time with your partner. Of course you want to spend more time with your friends. And of course you want to spend more time with your family.

But you have a vision. And you want to see it through.

The problem is most founders’ visions are challenging to reach. So they not only require a lot of time, but also a lot of brain power - leaving them drained of energy for other things - including social time.

It sucks sometimes. You have to get comfortable with saying “no” to many social events.

One way I’ve found to deal with this better is to try and combine social time with the next sacrifice a lot of founder make. Physical health. By going to play sport - I love doing it with padel or tennis. But really any sport will do. You can get your heart rate up and spend time with the most important people in your life.

Physical health

As I mentioned above, physical health is another big-time sacrifice for many founders (including myself).

And what I’ve seen with it, is that it’s very up and down.

Sometimes I’m running 5x per week and other weeks I don’t get my heart rate over 100 unless I’m getting a fright from how lazy I’ve been. And I’ve seen this with other founders too - once you’re in a rhythm it’s awesome! But once you slip out of it, it can be a nightmare getting back into it.

Don’t put too much pressure on yourself. It’s normal to struggle to find the time or motivation to exercise. It’s easy to think that you need to work that extra hour - I do this myself - but the thing is that you’re much more productive when you’re in good health.

And exercising is a great place for ideas to hit you.

So although it’s hard - find a time to carve out of your diary every day and dedicate it to exercise (even if that’s just walking). And if you ever miss a day, make sure you don’t miss two in a row - that’s when habits die.

Mental health

Building a startup is hard. We don’t need to beat around the bush.

It is a major rollercoaster. When it’s good, it’s great! When it’s bad, it can be awful, and super hard to manage everything.

And I wish there was a silver bullet. A trick for everyone to use. But the reality is this is not a one-size-fits-all problem. You need to find a system that works for you.

My first recommendation would be to see a therapist. It’s something that I haven't been great at. But when you look at the pinnacle of performers, they all (mostly) have some form of therapy.

The best sports teams have psychologists - as do the best actors, politicians, and business people.

Not only will it help you live a better life, but will also help you grow your business.

Other ways to try to manage your mental health can be as simple as going for a walk or spending time with your partner - or could be something a bit longer, like going on a weekend away.

Try be unproductive. It relaxes your brain. And sets you up for sustainable success in running your business. From personal experience, it’s way worse to push yourself to the point of burnout. Earlier this year, my body gave in. I was struggling to breathe one morning and got a strict talking to from my doctor (one that I needed months before). So don’t let it get to the point I did.

Fun time

This is one I really struggle with.

I feel super guilty when I’m doing fun, but unproductive activities. Even though I know I shouldn’t feel this way - in fact knowing I shouldn’t feel this way only makes it worse, because now there’s more pressure on me to actually relax. This sounds like a lot to some of you, but I’m sure a lot of you can relate as well.

I want to try and balance my life with more traditional “fun” activities. But I also have fun building this business. And I shouldn’t feel guilty that I like spending most my days building - and neither should you.

So here’s my take on what works well.

Deep-work.

On the days when I put in 3-4 hours of truly deep work in the morning:

1. I accomplish much more than on other days.

2. I have time to do other activities, like play some FIFA or go on a hike, or watch a movie with my girlfriend.

3. I feel like I’ve accomplished a lot.

So my suggestion is block out one or two 3-hour blocks in your calendar every day, and I promise you will finish way more work and have way more time to other things.

Being a founder can be challenging. But there’s nothing like the thrill of chasing an ambitious mission.

My picks to take your business to the moon 📽️

• 32 tactics to fight churn (link)

• How and why you should use lifetime deals (link)

• Recipe for a perfect lead magnet (link)

• How to use an email newsletter as a consultancy (link)

• Avoid these common product messaging mistakes (link)

Cool Opportunities 🛎️

• Ganas Ventures: Looking to invest in pre-seed and seed Web 2 and Web 3 community-driven startups headquartered in the US or Latin America (link)

• Top 10 accelerators and incubators for blockchain in Asia (link)

Tools of the week 🔨

• Founder Docs: Get all answers at the exact moment a problem pops up. A really awesome resource for everything building a business.

• Supademo: Close deals faster, drive enablement and scale product guides with high-converting, AI-powered product demos.

• Thera: All-in-one payments platform for fast-growing global teams. Hire, pay, and manage your people seamlessly while being fully compliant with local laws and regulations.

Cool startup jobs I found this week 🕵️

• OpenAI is hiring a Product Manager, ChatGPT

• Instacart is hiring a Retention Sales Development Representative

• Stripe is hiring a Lead Product Manager, Money Movement and Storage Platform

• Pave is hiring a Product Manager, Market Data

• Play is hiring a Growth and Marketing Leader