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David Pawlan of Aloa: “Re-orient the definition of failure”

Re-orient the definition of failure. People ask me if I’m afraid to fail. I say no, because I know that I will fail. Failure is synonymous with entrepreneurship. Whether you fail at something small, like an outbound lead generation tactic, or large, such as your business itself, it’s all part of the process. Failures give […]

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Re-orient the definition of failure. People ask me if I’m afraid to fail. I say no, because I know that I will fail. Failure is synonymous with entrepreneurship. Whether you fail at something small, like an outbound lead generation tactic, or large, such as your business itself, it’s all part of the process. Failures give us opportunities to learn and grow, to iterate and be better. If you can’t accept failure as a blessing, as a learning opportunity, then failure will drag you down rather than push you forward.


As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company” I had the pleasure of interviewing David Pawlan.

David is an entrepreneur and aspiring business leader. At 24, David has had the pleasure of working with his Co-Founders to build Aloa, a platform for outsourcing software development for startups. Named in Chicago’s 25 under 25 in Tech, outside of Aloa, David is working with a group of Chicago entrepreneurs on Fifth Star Funds, an evergreen fund focused on underrepresented founders, to bring greater accessibility and equity to Chicago’s entrepreneurial landscape.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

My name is David Pawlan, I am 24 years old and a Co-Founder of Aloa. Along with my four other Co-Founders, we actually started Aloa while in college at Vanderbilt University. As we were just having fun, building out apps and doing student tech consulting ourselves, we stumbled upon the pain point that so many entrepreneurs face: how to predictably and consistently build cost efficient software. We were in college, and had nothing else to do with our time (kind of joking, kind of serious!) so we decided to research it and see if we could figure out a solution. We fell in love with the problem of outsourcing software development overseas. At a high level, we believe in a world where anyone can innovate freely. At that time, we saw software development as a barrier to innovation, so that is what our focus became. If we can facilitate innovation, cool things will happen. Pivoting in 2018 to the model we have today, we are now three years old (all of us graduated) and have grown Aloa to a multi-million dollar business and have worked on almost 150 different projects.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Definitely! So it all really started with our head honcho, our Captain tried and true, Chris Raroque. As I just previously mentioned, while in college, we were building out apps and just messing around with tech ourselves. Over time, Chris slowly put together the team that we have today. With tons of different applications and ventures pursued, different teams came and went, and over time, one person would stay here and there. Fast forward to 2018, the team was settled on five us, with myself as the last member to join this dream team.

The Aha Moment really came when we were looking to build out our own tech team ourselves. We were in need of extra developer resources and had to figure out how to go about expanding the team. As students, we didn’t have a ton of money, so we simply couldn’t afford to hire any software developers in the US. We looked to students too, but it just wasn’t a reliable route as students, of course, had to often prioritize school over side work. We decided to look overseas, and everyone we talked to warned us against it. A disturbingly majority of people we spoke with only discussed the horror stories and instability of software development outsourcing. Now, think about it; why have we figured out how to predictably and consistently work with overseas talent in every single industry, except for software development. In an age of digitization, why is the most digital industry the one we struggle with the most? With that realization, we were in love. We fell head over heels for the overarching problem of outsourcing software development. We knew that there had to be a better way than how it is currently being done, so we went back to the drawing board and began to research, focusing on the existing pain-points, focusing on how we could take our first step at creating a world where anyone can innovate freely.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Oh, of course. Before I get into a story, it is important to recognize that the only thing that has kept us going, through thick and thin, is passion. We’re passionate for what we’re doing, we believe in our mission and believe in the value of our service. Since we are in love with the problem, any hurdles or bumps aren’t deterrences, but learning opportunities as to what doesn’t work. Each “failure” gets us one step closer to the right solution.

The moment that stands out most to me had to have been New Years of 2019/2020. All of us were on our separate family vacations, and in the matter of hours, we had three client fires hit us at once. For me personally, the fires hit the moment I got to the resort with my family. As my family got situated and hit the beach, I went straight to some seating areas, pulled out my computer, and got to work. We were all hands on deck as if all three client fires burst into flames, it very easily could have been the end of Aloa.

As a team, we all worked tirelessly through the days. Over the span of the next 3–4 days, we worked together to keep our spirits high and handle each situation in a practical and organized manner. As each of the instances are related to clients, I can’t really go into much detail of the situations, but my oh my was it stressful. We ended up getting through it, and looking back, it was actually one of the most fundamental turning points of our company, teaching us incredible lessons that have led to some of our most important development processes. Even though the experience was an emotional rollercoaster, it showed me that I am on the right path, as my passion was able to outshine my fear.

So, how are things going today? How did your grit and resilience lead to your eventual success?

Things are going really well today, which really does make me smile each time I say it. It is nice to look back and see how so much hard work and determination has led us to where we are, even though we are a team of 24–26 year olds.

Through our learnings, our passion, our grit, and resilience, we have continued to iterate our process to further our mission. Our quality of service gets better and better with each client experience, and the desire to continuous learn will always guide us forward.

Today, in this moment, we have around 20 active clients and are expanding our business offerings, as we look to make a splash in the B2B invoicing space. We felt pain-points ourselves (similar to our founding story of Aloa), so we decided to try and innovate to build a payment invoicing solution that solved our pain-points. We ended up building a platform that decreased our collection times by over 80% and saved us over $21,000 in processing fees. AloaPay (aloapay.com) is now live and building a waitlist of users.

Our ability to grind and always push forward has put us in a position to keep our eyes open and always look for opportunities. Fail fast, fail frequent. If you don’t take a leap of faith, you’ll never learn if you can fly.

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

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.

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?

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.

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?

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.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

The three main traits that have helped me succeed are pretty clear in my mind: passion, authenticity, desire to learn.

Passion. I spend my Sunday’s getting excited for Monday. Most people don’t work on Sunday, so that means I can’t be closing deals and helping companies grow. Monday is such an exciting day of the week because it is the start to the energy of opportunity. If you’re dreading work the next day, you aren’t passionate about what you’re doing, and your path to success will be much, much, harder.

Authenticity. If you ask anyone who has had a conversation with me surrounding anything I’m doing, they’ll all tell you how authentic and genuine I am. I want to be doing what I’m doing, and it bleeds through to my conversations! I am genuinely interested in my work, and love speaking with people to not only learn about their work, but see how I can learn from them. I remember when I first moved to Chicago after college (pre COVID), my friends would go to happy hours after work; I would go to networking events. Of course, sometimes I would have a fear of missing out and be envious of my friends. By and large though, I didn’t care what they were doing, because I wanted to be doing what I was doing. I was excited, engaged, and hungry to learn.

Desire to learn. If you aren’t eager to learn, you aren’t growing. One of my greatest strengths is my recognition of my gaps. I know that I have a ton to learn. One of my favorite quotes is by Ralph Waldo Emerson, “In my walks, every man I meet is my superior in some way, and in that I learn from him.” You can always learn something from someone, always strengthen your own skill set. I see each opportunity I speak with someone as an opportunity to learn, an opportunity to grow. I’m excited to learn, I live for it. So no matter what I’m doing, no matter what industry I get into, I’m going to have some aspect of excitement because it just means that I have a whole new roadmap of learning ahead of me.

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

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.

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?

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.

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

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.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading My Company”? Please share a story or an example for each.

Learn to walk, before you run.

“All overnight success takes about 10 years” — Bezos

Too often people’s perspective on entrepreneurship is skewed by availability heuristics. We only hear of ‘overnight successes’ in the news and via media, but in reality, this is of course not common, and not what entrepreneurship needs to be! You don’t have to follow the status quo and raise money with the intent to sell. That is of course a profitable and glorified route, but it isn’t the ‘right’ way to do it, as that is the beauty of entrepreneurship, there is no one way. For us, it is about diligence, patience, and building something sustainable that maintains our integrity. We started Aloa by focusing on early stage startups, first building an understanding of what we were doing before growing as a business. We focus on our customer experience, and in doing so, we’ve built a business that people love. By staying small and focused, we have been able to truly iterate on our process and grow with a smart mentality that maintains the integrity of our business, rather than getting out ahead of ourselves.

Uncertainty is opportunity

While you can extrapolate this phrase to reflect entrepreneurs starting business by filling industry gaps, I intend to point this phrase more towards internal operations. I just turned 24, so going into this, I knew that I had much to learn. One of the most helpful and important pieces of advice given to me was that in anything you try to do, someone has probably made ‘beginner’ mistakes before you. If you can learn what others have done, you can avoid hours and hours of failed effort. Where you are uncertain, you have opportunity. If you don’t know how to do something, reach out and network. Talk to people who have done it before you. Don’t make mistakes that you don’t have to. If there isn’t a concrete answer/direction in your mind, backed up by logic (not just gut), then you have an opportunity to learn/grow. Anytime I am getting into something new, I always make sure I spend my first few weeks just researching. I cold outreach and jump on calls with experienced professionals, asking questions and learning their stories. When I was tasked with taking charge of Aloa’s marketing initiatives, I didn’t actually start doing anything until I had talked with over 20 different marketing professionals, learning their opinions, perspectives, strengths, advice, etc. You can find the answers you’re looking for before you even know the question to ask, you just have to be hungry to learn.

Re-orient the definition of failure

People ask me if I’m afraid to fail. I say no, because I know that I will fail. Failure is synonymous with entrepreneurship. Whether you fail at something small, like an outbound lead generation tactic, or large, such as your business itself, it’s all part of the process. Failures give us opportunities to learn and grow, to iterate and be better. If you can’t accept failure as a blessing, as a learning opportunity, then failure will drag you down rather than push you forward.

Don’t chase the money, chase the dream

This piggybacks off of point 3 — if you are only focused on money, then any failure will be really painful. If you are focused on the dream, then failure is only helpful. If you build the company, money will come. It is really hard to not focus on the dollars, and especially once you start making money, it is hard to not focus on making more rather than maintaining the integrity of every minute detail. This came back to bite us at one point (I actually briefly talked about it earlier as a time when I questioned what I was doing with trying to start a business), so we took a deep breath, and re-oriented on our dream. Every month, we now do a re-orientation session to keep our focus on our dream of creating a world where anyone can innovate freely. If we focus on the dream, financial success will follow.

Don’t expect to go to happy hour with friends

Your company is your baby. Everyone on the surface knows that it takes all of your time to start a company, but people don’t really embody what that means. Your friends will be going to happy hour or watching football on Sunday. As much as it may pain you, these are sacrifices you have to make to invest in yourself. Come to terms before you dive in, that this is the commitment you’re making.

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. 🙂

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, Tides.org, 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.

How can our readers further follow you online?

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.

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

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

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