Patrick is the Founder and CEO of ProfitWell, a software company that helps subscription model businesses like Canva, MasterClass, Classpass, Vice, and Prezi with their monetization and retention strategies. 

In this episode, Patrick speaks to the importance of building a culture of feedback and the benefits of being a mission-driven organization. Listen to this episode (or read the transcript below) to learn about the importance of creating concrete values in the early stages of a startup.

1 When was the first time you managed a team?

If I take the definition loosely, it was when I was very young. I actually had a really interesting animal cracker ring when I was in elementary school. I was responsible for packing my own lunch, and I would essentially pack a giant bag of animal crackers and trade with everyone. But my first official job was at Starbucks, and it probably wasn’t until I started working at Profitwell until I got real management experience.

2 Have you ever had a manager or leader that you’ve looked up to?

I know that hate is a strong word, but I actually hated my first manager, but he was also the best manager I ever had. His name was Duran Derwin, and he currently runs People Ops at Stripe. He was my manager at Google, and I was just a young punk kid, and I didn’t appreciate the things that he was trying to help me with. He was trying to help me be my authentic self and find a solid work-life balance while honing in on my strengths. I was more focused on how to get a promotion and other immature things that really don’t matter.

At the time, I didn’t appreciate how important the things were that he was trying to teach me and I didn’t realize that I needed them to be successful. Looking back, he was one of the best managers I ever had.  

3How do you manage young punk kids?

It isn’t just an age thing, there are some 40-year-old punk kids and I think it just comes down to really helping that person realize that you’re trying to help them and letting them know that you’re there to connect the dots. As a manager, you have to make a very conscious investment into the well-being and overall development of the person you’re managing.

You have to take the preconceived perception that people have of managers and what their roles are and break them or flip them so the people you’re managing that may be a bit difficult understand that you have their best interests in mind, and you want to help them succeed in their career.

4 How does working at the Department of Defense compare to working with tech companies?

When you work for the intelligence community or the government, it’s super bureaucratic. There’s a lot of top-down rules and bureaucracies and there’s a lot of decentralization because you can’t just talk to anyone about your work because they may not have the same security clearance. For me, it was probably one of the most fulfilling jobs I ever had because it was very mission-focused. We were quite literally saving lives and supporting others that were saving lives, so it was really crazy.

Despite the continuous learning and constantly striving to find the truth, I always felt like everything was moving slowly because of the bureaucratic barriers and I noticed the same thing when I started working at Google. There’s something called Google depression and it basically means that the novelty wears off. Initially, I was extremely excited, and I loved getting all the cool perks and working with cutting-edge technology but then I started to realize that the work wasn’t that fulfilling. I noticed that it really wasn’t compelling work and I started to get tired of the bureaucracy.

One of the key takeaways for me was that a person has to be connected to a mission. Young people fail to realize that there aren’t enough perks in the world to make your work fulfilling and no amount of career growth will fill that void and that’s why it’s really important to help them connect those dots.

5 What did you learn from paying yourself a 50K salary?

It was actually much more dramatic than that, I chased in my 401 k which was around 10 grand after taxes and my salary essentially went to zero while we built the product. I worked for nine months to try and generate some form of revenue and tried to push as much cash as possible into the business. I then ended up meeting Peter Zoto who I consider my co-founder and he ended up also taking a very low salary which I think was around 36k at the time and it was strictly to cover things like rent and food because both of us always choose to reinvest in the business.

A lot of our core DNA grew from this as we started to introduce new practices based on these principles. We’ve started to associate raises with milestones, so if we are able to reach a certain goal, we will adjust our salaries accordingly.

6 How do you inspire culture or being mission-driven?

We have a fascination with the truth and the truth is never black or white. We’re making software and were trying to help other businesses and that isn’t black and white, so we really try to instill the mindset of focusing on the truth and figuring out what makes sense and that’s really permeated our culture. There is a clear separation between the identity of the corporation and the identity of the person so and it’s really important to figure out what motivates each individual employee.

7 When did you come up with your values at Profitwell?

I think our values have really evolved over time but it’s actually a really funny story for how everything unfolded. Basically, Peter and I had hired our very first employee and he wasn’t performing well at all. We kept trying to help him and we finally just asked him what was going on and he told us that our culture wasn’t making him want to perform and I really took it to heart. I was desperate to fix the situation, so I ended up reaching out to Dharmesh Shah, the co-founder of HubSpot and I explained the situation to him, and he basically said that the first 20 people you hire are the DNA of your culture. He explained that we weren’t doing anything wrong, and our first hire just simply didn’t share our DNA.

Since then, our culture has massively evolved and we’ve rewritten them about 3 or 4 times. Some of them haven’t necessarily changed but they’ve been codified differently to be more useful.

8 Have you made any mistakes in the past that you’ve learned from?

One of the first mistakes that I made was being too accommodating. In the early days of being a founder, I would take everything personally and think that everything was my fault and what I realized by being too accommodating is that it alienates other people and there are always trade-offs. So, if we were to accommodate someone on one policy, we may end up upsetting someone else, so we try to be really vocal about who we are and what we stand for in the interview process. We make it known that some things are non-negotiable, but we have a disagreeable culture.

9 Do you have any advice or great reads for aspiring leaders?

I recommend Patty McCord’s Powerful or Power because it’s really intense and direct and it really resonated with both my team and I because it’s all about stating who you are and treating people like adults. We try to emulate it in the sense that we always try to make things our own and take a little bit.