How To Interview For Culture Fit

Through interacting with business owners and CEOs, I’ve seen that some of them struggle to test cultural fit when hiring new employees. People and culture are two extremely important elements. But it’s hard to tell whether someone will embrace and add up to your company’s culture or not.

I’ve seen this first-hand after running a business for 7+ years. But that’s something you have to get right –at least, as right as possible. 

Culture fit is not an exact science.

You never know how new employees will adapt. But you as the business owner still need to take steps to put yourself in the best position. At Jakt, we’ve developed a process to help us get there and increase our odds.

Here’s how we do it:

Jakt’s Culture Interview

Each company has its own specific hiring process.

We’ve added one last interview to the series. At this point, they’ve passed everything else and we intend to make them an offer if they pass this part.

(They don’t know that though – although maybe they will now if they read this 🙂 )

In this step, we don’t test them on hard skills. Or ask about previous working experience, etc. Nothing.

We want to finish this meeting answering the following question: does this person fit with the culture we have created at Jakt and will they add to it? That’s it.

Back when I used to run these interviews (now our Head of Department runs them), we didn’t tell them what the interview was about beforehand. We’d just say they were going to meet with me for a bit or something vague like that.

And that’s because we want to get them at the most real selves. We don’t want them to prepare or overthink anything. Just to show who they really are.

At that point, they’ve never met me and there’s no rapport.

So, here’s what we do:

All I say is this—

“We’re going to talk about culture and our values at Jakt today.

I’m going to ask you a question about each one. You can pull from either business or personal life examples, whichever you’d like. And anything you aren’t comfortable sharing, you don’t have to.”

Then, I dive into the first one.

For example, “be your word” is one of them. I go ahead and describe what the value means to me in a sentence or two.

And then, and here’s where it gets interesting:

We ask them to talk us through a moment in their life where they did something that goes AGAINST that value.

“Tell me about a time when you didn’t do something you said you were going to do and it negatively impacted the people around you.”

And what are we looking for here?

We don’t expect perfection. We don’t want them to tell us they’ve never “messed up.” I’m the CEO and I can tell you there have been times that I’ve acted in ways that aren’t 100% in line with our values. No one is perfect!

We’re looking for how they handled the situation, Listening to the language they use and listening to how they reacted. What they were thinking. How they felt. What they learned from it. Etc.

And we’re looking for red flags.

Was this time just a time when they didn’t live up to the value or is this a larger thing? Do they have the potential to live this value at Jakt?

Is this a value we don’t think they can live up to at all? Or might cause issues with the culture?

And we go through this for all seven core values. So yeah, it’s a long interview. About 60-90 min. And it’s tiring, for us and for them.

But it’s worth it.

And it’s also a great way for us to get to know them. And a great way for them to learn our core values and about our culture a bit.

It’s helped us get into much more deeper conversations than regular interviews do. And that puts you one step closer to figuring out whether they’ll be a good fit or not.

However, there’s something that you want to do first. And that is…

Prerequisite: Fostering a safe place

Look, I’m not going to lie to you. These type of interviews are not easy.

Yes, you have to pull this kind of shit from people because they are not easy questions to answer. Especially during an interview.

And surface level answers are not good enough in this type of exercise. You really want to get to the details of the story. And keep on going one layer deeper with your follow up questions until you fully understand what their actions and words were, etc,

The more specific the better.  

But I can’t emphasize this enough: it has to take place within a safe space.

We let them share as much or as little as they want. If they ask whether they should give a business or personal example, that’s their choice.

Providing an environment of trust and respect is actually what will help you get more raw and truthful answers.

People have cried before, but not because we browbeat them. These interviews are emotional, and you have to help them feel comfortable.

Seriously, don’t push from a place of cruelty. This is not an interrogation. But you are trying to get some good info so you can learn more before you let them into your culture.

Does it work?

Mostly. (if you were expecting a firm 100%, sorry not sorry)

The truth is, nothing works all the time when it comes to people. You just have to give yourself the highest chances. And I truly believe this cultural interview helps you get there.

So, on top of this cultural interview, there’s also all the other normal interview stuff going on. Intro interview, skills-based interview, etc… References. All that.

The way we use this interview is more to rule people OUT.

If you don’t pass this, you don’t get in.

But just because we are ruling people out, it doesn’t mean we could still have people in there who negatively affect the culture. This is only 90 mins and we can only learn so much.

Along the way, we constantly monitor culture fit, evaluate it, and fire based on it if we need to remove the negative influence.

You see…

If we find red flags or things that don’t feel right, we pass. No questions asked. Doesn’t matter how good you are at the skills portion of the interview.

Protecting our culture is more important.

And if the answer is “I think they could be a good fit, but there’s just something not right?”

In my experience, don’t hire them either. It’s never worked out well for us when we were on the verge between yes and no.

If no red flags and no bad feelings and they pass this test, we hire them.

It eventually might not work out. But this is a step we’ve added that has made a difference and helped us filter people out. It also has the added bonus of introducing new hires to our culture during the interview process.

It’s your job to be a guardian of the culture

Everyone who comes into a company influences the culture. Culture is not stagnant. It evolves with each new person that joins.

But you can choose which people come in and influence your culture.

And once they are there, you can also maintain the standard and the importance of the core values and living them every day.

There’s no way around that.

You, the business owner, are the guardian of your company’s culture. It’s your job and your responsibility to maintain it as you grow. It all starts at the top.

Culture Takeaways

  • Testing every potential new employee for their cultural fit is important. One option is to do this through a cultural interview where you ask for their actions against your core values.
  • You need to pry for in-depth answers since it’s human nature for people to stay at a surface level. At the same time, foster a safe space for them to be comfortable with sharing.
  • Your company’s culture needs to be protected. Do this by filtering out the people you hire and keep them accountable for the values over time once they are there.


Core Values: How To Define As A Business Owner

Core Values DO NOT make you money.

Sales do.

Marketing does.

Channel partners do too.

But core values? Nah.

As a business owner or entrepreneur, you might be thinking this yourself or heard it before.

And, here’s the thing, they’re “right.” Sure, core values won’t directly put cash in your bank account on their own.


There is a massive return on investment when core values are defined, agreed upon, and implemented within your company.

This doesn’t mean writing them down on a piece of paper and then moving on. They won’t do shit if they’re filed away somewhere.

Core Values

Core values are the foundation of your company’s culture.

When they’re aligned across your team, you are fostering an environment that is capable of moving forward positively and profitably.

So, just because they aren’t cash flow generating assets, that doesn’t mean they’re not extremely important.

And honestly, you’ll probably lose a shit ton of money if you don’t establish and live up to them.

(How would I know? Because I’ve been there myself…)

You’ll have a mediocre company culture, you won’t attract high-performers, you’ll have high turnover etc.

That’s why, in many ways, your core values do have a monetary value. Not just to help you build a company that’s capable of growth but also to save yourself from being neck-deep in trouble.

How to Define Core Values (That Mean Something)

I’m sure that each company has a different approach to doing this –but this is how we did it at Jakt.

I first listed everything I could think of that was important to me. It was a long list of things that I thought would be positive drivers of our company’s success.

How many?

About 100 of them. I knew that many of those were not suited to be “core values” but I still thought it was important to write them down.

While you’re in this stage of the process, don’t be afraid to braindump everything you have and see what’s the end product.

What’s next:

Then, I brought these 100 values to my team. I think we were about ten people at that point (more on when to do this later).

And we deliberated as a group – which ones did they like? What resonated with them? Which ones hit close to their heart?

I personally believe that you need feedback from your employees. They’re NOT your core values. They’re your company’s. And while you might have started it, your employees are an essential part of it. Culture is made out of people – not the business owner.

From the list of 100, we eventually filtered it down to 15 core values that were important to all of us. To get to 15,  it was a process of refining them back and forth until we were all in a general agreement.

But 15 is too many. We decided 7 was the right number since more than that can be hard to remember.

So, we had another discussion about the values. Based on this, we narrowed it down again with me being the final decision maker if there were a couple we couldn’t decide between.


Not that long ago, I came across a talk from Twilio’s CEO, Jeff Lawson. In it, he explained how his company documented his company’s own core values.

They used a very similar process that we did. And I wanted to share how they did it because I thought it was great as well. Listen to the full talk below:

Your Core Values Can Evolve Over Time

Your company will evolve over time, offerings will change, and people will change. Who you are as a business owner will. And even what you stand for as a business will too.

So it should not come as a surprise that your values will evolve as well. They are not stagnant, but fluid.

A lot of people don’t see eye to eye with me on this.

They say core values should never change. But I just disagree.

I’m not saying they should change all the time. Or every year for that matter. And just because you remove one from the list of 7 doesn’t mean it’s not a value and importance to the company.

But there could come a time when there’s another core value that is a better fit than others. And I’m willing to make that change if and when needed.


Your core values don’t have to be the same in year five as they were in year one. Or when your company has 55 employees versus when there were three of you.

Jakt is definitely not the same when it was me and my roommate than now that we do $4M/year in revenue. Make sense, right?

When should you define your company core values?

That’s a good question. And I don’t think there necessarily has to be a universal answer.

We did it when we had about ten people. In hindsight, that might have been a bit late. Before that, I had traits and values in mind that were important to me. But they were not documented as part of the company.

I also don’t think you should do them when it’s just yourself. At that point, you have very little idea of how the company will look like as you start hiring people.

If I could go back and do it again, I’d personally say that the ideal timing would be between 3 to 5 people. But, then again, you have to find out what works for you and your situation.

Are they really that important?

It depends on whether you live them or not.

Turn your core values into actionable values. Not just cool words that sound good but don’t mean anything.

Here’s an example:

One of our core values focuses on creativity.

But the core value is not “creativity.” Because sure, you’re throwing your team a concept that looks cool. But what are they supposed to do with it?

So, we decided to define it as “Be Creative.” And I think that helps make it more livable. You can be creative. You can also easily use this in language. Hey Bob, be creative 😉

Or, another example, “responsibility.” We changed it to “take responsibility.”

As you can see, we use verbs before the value, so that they are actionable. And, once you have them clear, you also have to continuously…

Protect your core values.

Your core values depend on the people at your company. It only takes a few people that don’t take them to heart for them to start losing value.

One way we do this at Jakt is through a “cultural interview.”

I’ve written a whole article on this specifically (check it out here), so I won’t go into details.

Another way to do this, and this is arguably the most important, is to constantly be monitoring for them. If someone isn’t living a value, immediate feedback and discussion need to happen.

Otherwise, the value means nothing and the new standard is not living the value.

Also, this applies to you as well, business owner. With core values, everyone is on the same level and you need to hold yourself accountable as well.

In a worst case scenario where someone is a repeat offender and you don’t think they can improve or they are negatively affecting the culture, you must remove them.

Define Core Value (and Stick To Them)

  1. A good way to define your core values is by starting with brainstorming everything that’s important to you. Then, and with the feedback from your team, keep closing into the few that matter the most.
  2. Your core values are not static and should evolve over time. As your own company grows, they will too.
  3. They need to be actionable and liveable. You, as the business owner, also need to be the guardian of the culture and values, as does everyone else.


Your Vision and Mission Alone DO NOT Keep Employees: Here’s What Does

Every month we have a management meeting where we look back and audit the previous 30 days. We audit what worked best and what didn’t, compare numbers to the forecast, go over all the most important metrics, and plan for the next month.

In our last one –end of January 2019– we sensed that something was off. We had this feeling that management just wasn’t on the same page as everyone else.

Our first thought was that our mission and vision might not be clear or supported enough. However, I realized that those might not be the most important factors that drive our team.

What they were, however, I didn’t know.

So I asked the management team: “Why are you all still here?”

Why People Stay At Our Company:

After the initial blank stares, each of them started sharing their own personal reasons. And I learned that it wasn’t the company’s mission and vision. It wasn’t any one thing, really.

What came out in the discussion were 7 fundamental things that drew people in and kept them as part of the team:


Multiple people in the room mentioned this in different ways. As we all talked through it, we started to understand that it wasn’t just the obvious forms of opportunity –progressing in their careers, for instance.

But also the opportunity to grow. To do something different. The opportunity they have at Polpo to take on new challenges.

High Accountability

High-performers love being held accountable. They want someone that pushes them to be better and always stay on top of their game.

I really valued that they considered this a positive element of our culture. We don’t want things to get too comfortable. We don’t want to accept mediocrity. We don’t want “good enough” to be, well, good enough.

That’s the kind of people I want in my corner –and that’s what my leadership team enjoys. I do, however, think we can do better in this area. And we will focus on this moving forward.


Freedom can be shown in many different ways: freedom to express yourself, freedom of choice, freedom of responsibility, etc. That’s something I was very intentional about when I started the company.

I believe it’s a sign of mutual respect. I consider my employees capable of performing at the highest level, and I will give them room to play.

But, at the same time, it comes with the understanding that they will be accounted for and held to the highest standards.


Several people specifically touched on the opportunity to be creative on a daily basis. That they weren’t told exactly how to do things or the specific form a given work project should take.

We work with different clients which means that things change over time. And, after all, they fly the ship that they built. Executing the ideas and strategies they came up with.

It allows people to be creative regularly, to flex that muscle and work it out. More than just being fun, it creates ownership.


The people at Polpo and Jakt like working with each other because they share a culture, a goal and, underneath all, a drive to do more and go further.

High-performers prefer being around other high-performers because they can sharpen themselves on each other. They level up.

We make an emphasis on only letting people in if they share our values –as professionals but also as human beings. Obviously, it doesn’t always work. But we want to have people that we enjoy being around.

Problem Solving

Polpo and Jakt provided plenty of unique opportunities to solve complex problems. Many of the managers in the group mentioned this as one of the perks of their job: that there’s always a new, exciting challenge to solve.

I get it because that’s something that also drives me. Solving a complicated, smoke-off-your-head problem is very fulfilling –and one of the biggest rushes you can experience.


Jakt (a company under Polpo) has changed a lot over the years. What we do and who we are now is not the same as 7 years ago.

The willingness to adapt, to change strategies when the business requires it, is needed for our company. But it’s also good for all the people who appreciate new and different job experiences.

These seven elements were recurring themes over our conversation. Interestingly, you’d also see a lot of similarities between them and our company’s values –just worded differently.

All of them were important for feeding into the bigger picture –the culture of the company. And they mix to form a compelling environment that pulls people in for the long haul.

But what about your mission/vision?

Once you list the reasons people are here, you can see the negative image clearly. And it reveals what doesn’t make people stay.

I always thought that what made people want to be here was our vision and our mission. Maybe it’s why they joined us –I don’t know– but it doesn’t seem to be what keeps them here.

What I learned through this exercise is that is not what they get out of bed for.

Nobody said, “the mission and the vision of the company are just so compelling.” After all, we’re not solving world hunger, and we’re not landing a man on Mars. And that’s OK.

I think there’s a lie we keep telling ourselves in the startup world, and it’s that the grand vision is why people will keep at it day-in and day-out.

But it’s not. It’s the privilege of working, living really, within a culture that provides you with those 7 pillars above each and every day.

Note: I’m talking about my company. And yours might be different. Just saying that it’s important to know what really drives your people.

Why do I stay at the company?

They ended up turning the question around to me.

And funnily enough, a lot of the same reasons they gave apply to me as well.

Here’s what I said:

  • I like to create something out of nothing.
  • I like to have a group of great people and work together to build a company bigger than ourselves.
  • I want to have freedom and be able to work on what I want so I can express my creativity.
  • I want to be held accountable, and I want to solve meaningful problems.
  • I want to provide a space for people to grow and realize their potential.

At the same time, I feel a responsibility to my team and their families. I built this thing from the ground up, and now there’s a lot of people that it supports, and that’s a big part of what keeps me here.

Why people really stay, from my view. 

I’ve never been an employee. It’s not easy for me to put myself in their shoes. Which makes it really hard to fully understand why they’re here.

I know this though: My intention from the start was always to create a company with people and a culture that I’d work at myself.

And it was very interesting to realize that mission and vision might not be the most crucial elements that keep my team working together.

What came out instead were 7 things people valued across the room: opportunity, high-accountability, freedom, adaptability, problem-solving, people, and creativity.



How I’ve Built a 24/7 Personal Brand Machine

Over the last couple of months, dozens of people have asked me about my personal brand.

They’ve either read one of my articles (like you’re doing right now), listened to a podcast, watched a vlog, seen a Tweet or a LinkedIn post, etc.

Some of them are surprised. Others are intrigued. And there’s a few that want to get started as well.

They know that I’m the CEO of Jakt, plus I moderate a community for service-based business owners, and I have recently launched The Polpo Group. How do I have time to create content at scale?

But, before I walk you step-by-step on how I’m doing it –and how you can too if you are interested–

Let’s start with why:

I started Jakt, a digital product and innovation studio, 7+ years ago. I launched it from my tiny apartment in New York City. And I don’t want to pull the “rags to riches” cliche, but I was barely scraping by in the beginning.

So I closed my eyes and worked. Obsessively (I’m now changing that). Hundred-hour weeks became the norm.

And the truth is, I did it happily. I found purpose and meaning in Jakt and LOVED helping other businesses.

Now it seems, I “woke up” 7 years later. Jakt is now a $4M/year company with over a dozen fantastic employees.

Looking back, it hasn’t been easy.

There has been a handful of moments where Jakt’s survival was threatened:

Like when my business partner left about 2 years after we founded Jakt. Or realizing I needed to improve as a leader when half my team quit in a matter of weeks –it wasn’t all my fault, but it was my responsibility. Or when we got sued… on and on. 

There were also plenty of extremely satisfying moments. The thing is, I’ve learned a fuckload over the last seven years. Both highs and lows (and probably, even more, the latter) were packed with plenty of extremely valuable lessons.

But I’ve kept my mouth shut for the last 7 years. There are different reasons for that: one, I was too busy working. And two, I didn’t think I had enough “meat” to bring to the table.

My role at Jakt has transitioned into a high-level architect.

I’m focused specifically on our strategy, vision, and having the right people around me.

That has also reduced the number of hours I work on Jakt –freeing up space for my personal brand, SBB, and the new businesses I’m spinning out of The Polpo Group. Our CFO + Accounting service for agencies is an example of that (check it out if you run one).

At the same time, I now think I have enough experience to add to the conversation. While I haven’t seen it all, I’ve seen a lot –and I only create content about what I know anyway.

My personal brand is an investment. My honest goal is to build an audience that trusts me, my content, and my experience by adding a disproportionate amount of value. And then redirect that attention to present and future business ventures.

I am finally ready to get started. So that’s why and why now. Let’s talk about how.

A 24/7 Content Machine

I look at my personal brand as it’s own little business. As such, I’m applying principles I use to run Jakt + the other Polpo Group companies to this.

You can’t build a 24/7 content machine all by yourself. Seriously, this would be a 100+ hours/week if I had decided to fly solo. There’s just no way one person could do all of it.

So, something I’ve learned about building your personal brand (it’s all still fairly new to me), is to not do it alone –as long as you can afford it. But building teams and gaining leverage is something I have experience with.

For my personal brand, I see myself, once again, as the CEO and architect. My job is to set up systems, tools, and find the right people. There are obviously things that only you can do –be on video, talk on podcasts…–, but don’t be afraid to push other decisions out to your team.

That has helped me reduce the number of hours I dedicate to it. Instead of spending all my time on producing and content distribution, I spent the first month getting the “machine” set up.

I found the right people, implemented the right systems, created and refined our workflow, etc. It went from almost 20 hours per week in December 2018 to less than 5 hours per week in January 2019.

You’ll see how there’s just no way I could do this alone. Really, I am now spending roughly 20h/month, but it looks like I’m posting 24/7. Well, it’s because my systems have created that constant flow.

Let me run you through a week’s worth of content so that you understand the magnitude of what I’m talking about:

Written Content

This is how I use written content:

  • 3x 1,000-word articles (like this one). Publish them on my blog, Medium, Quora, Linkedin and create snippets for Twitter. We sometimes submit them to Forbes, Entrepreneur, etc. for wider distribution + SEO.
  • Daily post on LinkedIn. 3x/Week will lead to the newly published article. 2x/Week will direct to either a podcast or a vlog. And 2/week will use them as original content.
  • 10+ tweets per day. We use Buffer to schedule them in advance.
  • 3 emails per week to my newsletter. These are usually 350-400 words, and I redirect them to another piece of content.

The way I can create so much written content is with the help of a ghostwriter. Yes, I could take care of all this –but I’d rather headbutt a knife than spend hours on end checking for periods and commas.

It’s much easier to have someone who can capture my voice and understand what I’m looking for. We first have a 50 minutes weekly interview where we discuss the week’s topics. Then, after he sends me the article, we go through the final edits.

For the Linkedin, Twitter and Email content, I don’t even check over that anymore because we’ve gotten into a well-defined groove. He also knows my voice so well that I trust what he puts out.

Audio Content:

I host a biweekly podcast called Reflections of a CEO where I talk about running an agency, entrepreneurship, personal finances, and personal development.

We post it on Anchor, and it is distributed from there to all mainstream platforms: iTunes, etc. From there, we also link the podcasts to my social media channels –Facebook, Linkedin, Instagram stories, etc.– to drive its exposure.

Finally, we use that big piece of content –the Podcast episode– and create 1-minute clips of its most valuable moments. These are micro pieces of content that we distribute to socials as snippets.

Video Content:

I create one video blog (vlog) episode per week. They’re usually 15 to 30 minutes in length. But I also sometimes create shorter videos on topics I’m interested in talking about when I feel like it/seems to me like it can help people.

I host my show (called The Journey) on Youtube and Facebook Watch. In addition to that, I film myself when recording the podcasts I mentioned above so that they also become video content in itself.

Side note: As you can see, repurposing content across platforms is something that I’m really emphasizing. The most expensive thing (we’ll talk $$$ soon) is to create the content.

Why wouldn’t I try to bring the most exposure as possible to it?

From each piece of video content, we also pull 2-4 microcontent clips that we distribute on socials –mainly Facebook, Instagram, and Twitter.

How much am I investing in my brand’s equity?

That’s a good question. Something I am really trying to encourage is breaking the money taboo and promoting an open discussion. So how big of a hypocrite would I be if I didn’t give you numbers?

There are two main costs to it: content creation and paid advertisement.

I currently spend about $6,000/month in creating content. That includes written, audio, video, social media management, social media content, etc.

Then there are paid ads. I will be spending $3-5k/month on Facebook and Instagram Ads. In Q1, the majority of spending will go towards building an email list. My goal is to get to at least 10,000 subs this year.

Why am I focusing on an email list and not using ads on growing a social media presence?

There’s a couple of reasons. First, you own the email list. There are no algorithms that limit your organic traffic, etc. If you have 5,000 subscribers, 5,000 people will receive your email. And second, having an engaged list makes it easier to build a relationship and present them with whatever I decide to sell in the future

So, all in all, I’ll spend $100k+ on my personal brand in 2019. While there won’t be an immediate return, I’m playing a longer game here. That said, this is an experiment. There may actually not be a positive ROI (although I really think there will).

But even if there’s not, I am not risking money I cannot afford to lose. Whenever I spend money on experiments, I only spend money that, if it goes to 0, I’ll still be totally fine.

In this case, I’ll be fine financially no matter what happens with my investment. I’ll also have learned a ton, so to me, it’s a win regardless.

Always play a game you can’t lose.


  • Building a personal brand is not a one-man show. If you are a CEO, you don’t want to manage a whole team of graphic designers, podcast producers, ghostwriters, etc. You want 1 guy who manages them for you –so that your time is not wasted.
  • There are different types of content that you can create: audio, written, and video. Ask yourself if there’s one that comes more naturally to you –and start there. But don’t be afraid to try new things.
  • Building a personal brand will take you out of your comfort zones. I am more of an introvert, and sharing with people doesn’t come naturally to me. But I force myself to do it anyway.
  • This is not a vanity spending. I am not throwing $100k to have people tell me how cool I am. I am ROI-focused (even if it’s long-term). At the same time, helping other business owners is a HUGE passion of mine. There’s nothing better than hearing someone say that I helped them out with their business.

Building a Business Leadership MANAGEMENT

Created, Not Born: The Mistakes and Learnings Of Becoming a Leader

I messaged the office again –I’d be “working from home” that day.

What I did not tell them is that I’d be stuck on the couch while thinking about shutting down the business. I just couldn’t go on like this.

Jakt (my company) was going through its lowest point. In a matter of weeks, more than half the team decided to leave and jump ship. I guess they thought we were sinking, and I don’t blame them.

Why is everyone leaving us? –I kept on asking myself.
No matter how much it hurt me to see everyone leave, I knew there had to be a deeper, underlying issue to it.

My conclusion: I was not a leader. Not a good enough one, at least. My team was falling apart. I had not set a clear, inspiring vision for the company that they wanted to contribute to. I had not created and fostered a great culture, and I never offered them the growth opportunities they craved.

Honestly, I was just trying to keep my head above water and make sure to keep everyone paid. I couldn’t spend time on those other things — or so I told myself.

I didn’t even know what doing those things really meant. Culture? What is that even? A vision for the future? Ya, sure, I have some ideas but I have no idea if it’s right or if I’m just crazy. So I’ll just keep those to myself. Helping people grow? How the hell do I do that?

Just a Job

Everyone just had a job, but no one was part of a company together.

That was the final breaking point, and it was clear as day I needed to find a way to change and grow.

Now, almost three years later, I still won’t ever say that I am a great leader. Being the CEO of a $4M/year company is, opposed to what many people would think, a very humbling experience. You make a lot of mistakes –and they cost you money, time, and relationships. I still have a hell of a lot left to learn.

But I am much better than two years ago.

These are the two key mental shifts that have helped me in this ever-evolving transition towards learning to become a better leader:

From Transactional to People-Centered

I started selling on the Internet when I was fifteen. I would buy designer bags from a physical store, resell them on the Internet for a higher price, and cash in on the difference.

My product was inanimate objects –not a person with feeling emotions, desires, and needs. I bought them, sold them, and made money off them –no personal feelings attached.  

Even during my first year at Jakt, everything was still simply transactional. I did not have to manage and lead people (there were none) –I just had to do the work for my clients.

As I started hiring people, I kept treating them like they were the purses I sold –not realizing that a service delivered by people to people is much different (this wasn’t so obvious as a 23-year-old). I would get business coming in, they would do it, and I’d make some money. It sounds call, but the truth is that I was just applying what had worked for me –without realizing that the context had changed.

And trust me, that’s a HUGE difference in being the CEO of a company. It’s one thing to do the work yourself, but it is a much different thing to lead a team of people to do the work.


It’s About the People

I now understand the importance of (and working daily to get better at) setting an inspiring vision, promoting a positive culture, and helping the people on my team grow both personally and professionally. How can I instill trust in my people if they don’t know where the company is headed or how their actions help us get there? That’s something that I try to keep top-of-mind by making an emphasis on culture, vision, and values during our weekly meetings.

Hiring the right people is another important leadership element. Here’s how I see it: I want high-performers like myself to work for Jakt.. Would I want to work for someone that micromanages what I do and doesn’t trust me? Or for someone who doesn’t hold me accountable to a high standard and pushes me to be better? Absolutely not.

To bring out the potential of your team, you need to set an exciting vision for the company’s future, foster a great culture, hire the right people, and then just get out of their way.

I used to think of people as money-making assets. Not because I didn’t care, but because that’s what I learned from my eBay days. I was not empathetic enough of their needs and I didn’t effectively communicate with them –and I still wondered why they left!

Now I understand that truly connecting with people on my team, supporting them as individuals, and caring about their professional career and growth is not only important to do, but I also enjoy it tremendously! Managing people is challenging but, if you are truly genuine, people will feel like they belong to something bigger than themselves.

From Emotional to Accountable

Not being able to make it to the office because you are paralyzed by anxiety and depression is not a good look, trust me. No hero story was ever written about the war general that ran away from the battle when it mattered the most. But how can you fight through the tough times and come out on top?

Being willing to eat shit (quite graphic, I know) is an underrated leadership quality. A CEO is like a goalkeeper in soccer. You are the last line of defense and, when everything else fails, people look at you to save the day.

I struggled with having tough conversations with people for a long time. It didn’t matter how much I expected from myself, it still was hard to let people know they were not performing at the level I needed them to be. But leaders simply can’t afford to do that.

You have to lean in into difficult conversations and deal with the rough stuff. Otherwise, you’ll find yourself with a team that accepts mediocrity as the new standard because everything starts at the top. Which means you have to walk the talk and be accountable yourself. People believe actions over words, and you have to set an example.

Finally, I’ve learned that leaders have to be emotional counterparts. When things go South, I must be their rock and take all the blame –it’s on me. There’s no place for shifting blame, and if the Company is failing, it’s on me as a leader. I have to take full responsibility –while still holding people accountable– and give them the genuine reassurance that we’ll be okay (here’s a more in-depth article on blind confidence as a leader).

And when things go well, I give all the credit to the people on my team who make it all happen.

A Final Word:

There have been thousands of books about what makes the perfect leader, but most of them miss out on something:

Being a great leader will always stay on the horizon. What matters is the process of becoming a leader. It’s a skill that needs to be crafted and perfected daily –something you have to work on. I have learned that every experience adds another layer to what leadership really is. But moving from being a transactional manager to focusing on having the right people and culture, communicating my vision and becoming more accountable has helped me take a big step forward on this journey.