So you want to work in (or run) a creative startup.


I spent the majority of my Saturday conducting interviews for my startup- The Cleveland Flea. We’re hiring for three internal positions- a big leap for a team of 4. We’ve been here before, of course. But never with such confidence and clarity. We’re not approaching this with fear or scarcity or even because we’re drowning in work. But that has been us in the past. It’s hard to get to a point in a startup when you have your shit together in all areas- in fact that’s sort of what defines a startup. You’re scrappy. You’re new. You’re building the plane as you’re flying it.

But not everyone is cut out to run one and not everyone is cut out to work inside of one. Here’s a look behind the curtain at Startup Culture (well, at least ours and the ones we study) and what it can be like to work within that environment.


Non-VC High-Growth Startup
We’re a high-growth startup who is fully self-funded (ie we don’t take venture capital- yet). We’re similar to a nonprofit where we have a very strong mission and have a huge service component to our business. But we make every dollar we need. We don’t have investors. This was important to me for a few reasons. I don’t think that anyone should have given me money before I knew the basics of what would be required to make money inside my business. I would, however, take money now or start a VC because I am officially a CEO and I have both expertise and credibility and most importantly- business confidence. I think if someone would give me money now, I would 100% be able to turn it into a profitable investment with some predictability.

VC-Backed Startups
These are the types of startups that you hear about all the time in Silicon Valley. How this sort of works is that someone has a great idea and then has to develop it (usually as a side hustle because they’ve got bills to pay) and when it gets to a certain point they try to sell investors on it so that investors will give them operating capital for a certain period of time- usually the time is based on when they’ll be able to become significantly financially viable. So the investors get paid back soonish.

Small Businesses
Many small businesses can’t quite entertain the idea of growth. They’re either too early in that process or they really aren’t trying to grow. And that’s perfectly fine. When it’s not fine is when small businesses want to grow but can’t figure it out and so they sort of avoid it and focus on scarcity only. Having a growth mentality is good if that’s what you want but it’s also fine if you want to remain a one person or very small operation. You just have to be really really good at what you do because competition does not care if you want to remain small.

Side Hustles
We support many side hustles at Cleveland Flea. A side hustle is a part time business, essentially. Many side hustles are run by people who have full-time jobs that they like or don’t like. Side Hustle Businesses are either looking to grow or not- and again, that’s totally fine. The one issue with startups is that if they do want to compete with full-time businesses they will have a hard time. They have limited time to think about their businesses and that does impact finances, happiness, quality of product, innovation, customer service- growth, in other words.

Not-for Profits
Lots of people who love creative startups tend to also be drawn to nonprofits. I think because they both have strong missions and typically want to solve a human problem or innovate the way we live or do business. Nonprofits are regulated via the IRS in a different way, allowing them to make money in ways that for-profits are not allowed.

Startups are typically new businesses and whether they aim to grow or not depends on the founder(s), board and vision. Where your mission is why you’re showing up and, your vision is typically how you’re going to spend your time and if you see yourself as different on day 365 than on day 1 of the year.

It can be a total trip working inside of a startup. It basically requires that you have a similar mindset as you would to own your own business.

Characteristics that work well within a startup:

Personal Responsibility




Being ok with risk

Patience, but high work ethic

Being results-based


Determined work ethic


Growth mentality

Working in a startup is not for everyone, and growing a startup is not for everyone. I think it’s totally fine that people be in the environments that work best for them. We need all sorts of businesses and people.

Why people sometimes don’t like being in a startup:

They’d like more structure

It can be ambiguous to them

Job descriptions often change, grow and morph depending on what the business needs

There is usually lots of internal growth

You don’t often get to experience lots of wins up front

It takes being personally open to growth

The salaries are often lower (initially) than in larger companies

It’s a typically tight-knit type of environment, and if you don’t like or agree with who’s around you, it can be really tough to like your job

From my experience, I have had to work for years to become a boss that delivers what both my business needs and my team needs- and that has taken tons of hard work, personal growth and lots of failure. I just now (7 years into running my creative startup) that I feel like I have gotten out of my own way so that I can show up as the person my team, company and customers need.

I love what I do. I love my business. I am so grateful for what it’s taught me. But it wasn’t always that way. I hated my business for a while. And I’m so very glad I got to the bottom of what I was thinking about it as a boss / leader / founder so that I could change those thoughts and finally see the positive results I had always been looking for.

I’m so grateful I have a passionate, hardworking, committed, funny team that is committed to our shared mission and that they stick with me through all of our growth.

And I couldn’t be more excited about our future!

If you don’t know, I coach Dreamers, Startups, Female Founders & their Teams!

Stephanie Sheldon