Aloa Founder David Pawlan: “Passion Drives Your Energy”

David Pawlan Aloa

David Pawlan co-founded Aloa with four partners right after he graduated from Vanderbilt in 2019. Together with his team, David pursues his passion to “create a world where anyone can innovate freely,” because they all see that software currently prevents that from happening.

In over three years, David Pawlan has expanded Aloa to “over 150 projects across over 30 different industries.” His success with the company has led him to be named to Chicago’s 25 under 25 in the tech industry.

Outside Aloa, David Pawlan works with a number of Chicago entrepreneurs, with whom he created a “venture philanthropy fund” called Fifth Star Funds. The fund builds “equity and accessibility in venture capital for Black founders,” and is also “focused on the family and friends around (early stage).” Since the team wants to “create a brighter future and better future for all entrepreneurs, no matter your background,” all equity taken by the fund is reinvested into the fund itself.

At Aloa, David Pawlan aims to grow the company “through an iterative process.” They learn from every experience and apply them the next day and moving forward. This process ensures that the company always remains innovative, which is important for their mission to “create a world where anyone can innovate freely.”

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I think one of the main things that makes Aloa different in our space is our dedication to our clients, really putting their interests first. David Pawlan, Aloa

Jerome Knyszewski: What do you think makes your company stand out? Can you share a story?

David Pawlan: I think one of the main things that makes Aloa different in our space is our dedication to our clients, really putting their interests first. We know what it is like to be on the “client” side of the relationship, so we empathize greatly with those we serve. And we truly see it that way, we are here to serve. It is our role to further innovation by serving those who need our service. There have been many clients that we have turned away or pointed in a different direction because we truly didn’t think we were the best fit for them. We are only going to move forward on an engagement that we believe we are the best route for the client. If we don’t think we’re the best, then we’ll do our best to point them in a better direction.

A story that really stands out to me is one that includes myself as well as one of our product team members. We had someone reach out to us, via our website chat, at around 2am on Friday. One of our product team members happened to be up, so he jumped in the chat and talked with this lead for at least an hour. After their conversation, the lead was directed to me, and I jumped on a call with them on Saturday. The reason this stands out to me is because this is an amazing example of how we put others first. A non-sales team member took the initiative to engage in a conversation that he had no idea if would even turn into a client, it was just a simple chat. And as the sales person, I jumped on a call, during my weekend, to hear about this individual’s pain points. Later on after we eventually signed a deal with the client, they mentioned how shocked they were to get a response at such a late hour, and how that experience heavily weighed in their decision to go with us. We easily could’ve waited to respond the next morning or had the call on Monday, but instead we kept our priority of always putting the client first. It’s a story that I look back on really fondly as it makes me feel good to really follow through on what we preach.

Jerome Knyszewski: Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

David Pawlan: The funniest mistake I can think of when we were first starting was a time when I was still in college. I was always taking calls where I could, whether that be in one of the dining halls or in an empty classroom. My friends would always walk by and mess around with me when they would see me on calls, and one time the person I was speaking to heard some comments people screamed that weren’t business professional, to say the least. It was funny, I’ll give my friends that. I actually had to catch my breath to try and hold back laughter, but it made me realize the need to separate different parts of my life. If I wanted to succeed with work, I needed to treat it as work. That experience heavily influenced where/when I took calls while still at Vanderbilt.

Jerome Knyszewski: Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

David Pawlan: Absolutely, and I love this question. We have received a lot of advice throughout our years of working on Aloa. A piece of advice that we followed off the bat was to go for any business we can. It sounds logical, so we followed it. However, as we pursued this route, we were able to learn our lesson, that it is better to make something that a few people love rather than a lot of people like. It wasn’t easy to grow the business as we weren’t really niche, we weren’t understanding the needs/pain-points of our clients because the client archetype was so different with each outreach. We ended up pivoting our outreach strategy and really only targeted early stage startups. This was an amazing decision as it allowed us to really fine tune our service and build a solution that was not only scalable, but adaptable.

If you aren’t passionate about the problem you are looking to solve, you will burn out.

Jerome Knyszewski: Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

David Pawlan: Passion! I know this is a recurring theme of what I keep saying, but I couldn’t believe it to be more true. It doesn’t matter what industry you are in, or what you are doing. If you aren’t passionate about the problem you are looking to solve, you will burn out. Building a business is not easy, it takes a lot of effort and sacrifices. If you aren’t obsessed with what you’re doing, if you aren’t having fun and truly enjoying the experience, then you end up feeling burnt out if things start going south.

It is easy to be passionate and excited when things are going well, when you think you’re onto something. It is REALLY hard to be passionate and excited when it seems like the floor is crumbling below you. If you only care about the money, or a certain approach, then you are subjecting yourself to burnout because your expectations are built on a specific success metric, rather than on the experience. Your passion drives your energy, your authenticity, your desire to learn. If you are able to walk away from a failure feeling excited that you’ve learned something, then you have passion and the right toolbox to survive burnout.

Jerome Knyszewski: What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

David Pawlan: I work with Startup Founders and C-Suite Executives every day. I have seen some companies explode while other companies buckle and fall. I feel like a broken radio, but I’m going to touch on the same theme; the ones I’ve seen succeed are the ones who are in love with the problem, and not the solution. If you are in love with the problem, then any failure is just another way that didn’t work; it’s the whole Thomas Edison phenomenon. He didn’t fail 10,000 times, he just found 10,000 ways that didn’t work. The same principle holds true — founders that seek to learn are ones that succeed. If you are looking to build a company around a single solution, then you are likely setting yourself up for failure. If you can reframe your perspective to fall in love with the problem itself that you are trying to solve, then you are doing yourself a service in building a roadmap that will help you avoid common errors.

If we as a society invest in each other, cool things will happen. David Pawlan

Jerome Knyszewski: In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

David Pawlan: All of the behind the scenes work of running a company is incredibly underestimated. It takes so much effort, so much more than most realize. A very simple example is thinking about cold email outreach. Everyone thinks about the time intensive nature of doing cold email outreach, sending emails, getting on calls, etc. That part is fun though, because you are actually engaging with people, taking a shot. However, in order to get there, you have to do days/weeks/months of research to figure out who are the right people to actually be reaching out to, and then during the campaigns themselves, you have to do continuous research and data analysis to continue iterating on your approach. So, you have to spend time researching and compiling the list of people you want to contact, you have to find their emails, and then send out the campaign. Once the campaign is sent, you not only have to find a whole new batch of emails, but you also have to iterate on your outreach based on the previous campaign results. Maybe you need to test new messaging, a new subject line, a new follow up sequence, etc. It’s constant work, and while necessary, most of it is not fun.

Jerome Knyszewski: You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

David Pawlan: Ha, I try to be a person of influence! I guess hopefully one day that will come true. If we as a society invest in each other, cool things will happen.

I’d like to take this question to talk about what I’m working to create on my nights and weekends. There is a disgusting gap when it comes to financing startups led by underrepresented founders. This past year has opened the eyes of myself and some other entrepreneurs in Chicago as to the inequity of our space. If you don’t have access to family capital, how can you find that initial $20k or so that it can take to start a business? We as humanity need to better invest in each other, because there is world-changing innovation waiting to happen from all walks of life.

About Fifth Star:

Fifth Star Funds is a venture philanthropy fund seeking to address the funding epidemic in America where only 1% of venture capital is awarded to Black founders. We accomplish this by investing in Black tech founders in Chicago at the early stage “Friends & Family” round. We believe the funding gap at this stage is the most critical to address, as centuries of inequity have prevented these potential entrepreneurs from having the initial capital to start their businesses. Any individual, corporation, or foundation can contribute to the fund as a tax-deductible donation, and 100% of all returns from successful investments are reinvested into the fund to support future generations of underrepresented founders. We are partnered with leaders in the industry such as 1871, Winston & Strawn,, and many more. The Chicago flag features four stars that represent pivotal events in our city’s history; we contend that the Fifth Star belongs to underrepresented founders and the extraordinary impact they will have on our city’s future.

Jerome Knyszewski: How can our readers further follow you online?

David Pawlan: For sure — you can keep up with Aloa and our efforts through our LinkedIn, Twitter, and Blog. You can also follow/connect with me on LinkedIn or Twitter. I’m not really too active these days, but I am always eager to engage with those who want to have a conversation.

Jerome Knyszewski: This was very inspiring. Thank you so much for the time you spent with this!

David Pawlan: Absolutely, thank you for taking the time to hear my story!





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