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Is Your Startup A Rocketship? Be Prepared To Face These 7 Growing Pains Every Founder Deals With During High-Growth Phases


There’s a false belief a lot of startup founders have, and it’s that at a certain point, “everything gets easier.”

I was just having this conversation with a founder a couple of weeks ago, and it reminded me so much of my previous company, Talent Rover. At many points along the journey, I thought, “Once we have this person in place, things will settle down.” Or, “Once we cross this milestone, then we’ll be in a good position.” And sometimes, that was true. But more often than not, getting that right person in place, or crossing the next milestone, only meant more growth—and as a result, more challenges to solve for.

The process of building a company never really ends.

All that really happens is the things that used to be difficult, slowly become easier—which unlocks the next 10+ situations you’ve never dealt with, and so on.

The one constant you can assume will always be true in business is that things don’t get easier, they just change and become different over time.

When you’re first starting out, your number one issue might be hiring. A year later, your number one issue might be cash flow, or client retention. None of these obstacles are really any more difficult than the others. They’re just different. And walking into entrepreneurship understanding this mentality is what will help you not chase the mirage of light at the end of the tunnel.

These are the growing pains you can expect to encounter along the way—and how you should think about approaching them.

1. Mindset

If you are an entrepreneur, your venture will never be a 9 to 5.

End of story.

A lot of founders work hard with the assumption that at a certain point they can sit back, relax, and enjoy the fruits of their labor. And yes, there will be moments where everything feels great, but all in all, the only moment you’re going to be kicking your feet up and relaxing is when you’ve completely exited the business (and even then, you’ll probably find yourself roped back in).

The sooner you can internalize this reality and make it part of your mindset as an entrepreneur, the more prepared you will be for the journey ahead. Your venture isn’t your job. Your venture is your life. There is no separation. Which means, there is no “off” switch, there are no “banked vacation days.” Anything that goes wrong is your problem, regardless of what else you have going on at the time.

If you’re going to make the commitment to become an entrepreneur, be prepared for the strength of your mentality to be tested.

2. Humility

At a certain point, you as a founder are going to come to a realization.

You can’t do it alone.

You’re going to hit a point where you’re working yourself to the bone, and you’re realizing that by trying to do everything yourself, you are actually doing the bare minimum in each department and, as a result, the whole thing is suffering. Your first instinct is going to be to fight the fact that you see yourself as a “failure,” but that’s not the right conclusion. Instead, you need to realize that it is impossible to go at it alone—and what you need is a team. 

Your success is not going to be about you, or your idea, or your product. It’s going to be about the strength of the team you are able to put together in order to do all of those things at an incredibly high level.

3. Team

So you decide to start building a team.

The single most important thing you can do as a founder is hire people who are better, faster, and more knowledgeable than you within their specific domains of expertise. Your job isn’t to be the smartest person in the room. Your job is to organize the smartest people in the room, and give them what they need in order to be successful on their own.

What you are ultimately hiring for is a growth mindset. 

A lot of people say they want to work for a startup, but the reality is, very few are cut out for it. Startups are a whole different animal than working for a large company. Especially in the beginning, things are constantly changing and there’s very little certainty over exactly what the company will become. 

Everyone is learning how to build the ship while the ship has set itself out to sea. 

4. Training

As you begin to hire, training is going to quickly become your number one focus as a founder.

If you spend the time early on to connect with and train your employees, to get them to see things the way you do, you will build an unshakable foundation that will set the groundwork for everything else to come. If you don’t, then all you’ve done is increase your overhead while continuing to work yourself into the ground.

Training, and making an intentional investment in the people you bring on board, is what will allow you to give them the reigns to go off and be successful without your direct involvement.

Again, this doesn’t mean things will get easier. All this means is you are now free to go on solving the next 10+ obstacles for your business.

5. Playbooks

Every department is going to end up needing their own strategy playbook.

For example, your sales team needs to know what you sell, how you sell it, why you sell it, etc. Any and all processes, strategies, best practices, and so on, then need to be documented so the department can continue scaling on its own without you. If you have made it this far into the startup journey, then congratulations: the vast majority of your time will now be spent putting procedures in place so the company can begin to grow larger, much larger, than yourself.

The reason playbooks are so important is because as you continue to grow and hit big growth spurts, you are going to start hiring groups of people—not just one or two people at a time. And as you bring on a bunch of people all at once, training those individuals becomes very difficult if you don’t have scalable materials to provide them.

6. Culture

Culture begins the moment anyone else joins your venture with you.

But you really start to see the impact of culture when you hit five to ten people, and then twenty, and then fifty, and so on. The company’s life depends on its culture—because it becomes the unspoken language of what guides everyone in the company forward. Playbooks are necessary from a process standpoint, but culture is more than just a list of values. It’s the way employees and team members interact and treat each other.

Trust me when I say, if you don’t deliberately shape your company’s culture, it will become one of the hardest things to fix later on down the road.

7. Money

And finally, as always, is the challenge of money.

Most small businesses actually don’t fail because there wasn’t a market for what they were selling. Most fail because they didn’t manage their money effectively. They thought they had more cash than they did, or they thought their cash flow was healthy when in reality they were living “paycheck to paycheck.” 

A lot of startups, for example, get huge rounds of funding and then go out and buy lavish offices, fancy desk chairs, big screen televisions, etc. In reality, if the check had been a fraction of the size, they would never be buying any of those things. As a result, they start to lose sight of what the business is and how they are actually going to do what they’ve set out to do.

Managing your money effectively is equally, if not more, important as making sure you don’t run out of cash as you’re doing it.

Brandon Metcalf is the CEO and Founder of Place Technology and a partner at Blueprint Advisory. He has extensive experience creating, scaling and leading global companies, with a deep understanding of building successful SaaS and Salesforce products.

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