Pawlan, a Serial Entrepreneur at 26, Proving that Age is but a Number
I had the pleasure of interviewing David Pawlan, serial entrepreneur at only 26 years old. David started his first company, Aloa, with friends from college when they were having trouble finding developers for different tech projects. After personally experiencing the pains of outsourcing software, and hearing about countless horror stories in software outsourcing, David and his team set out to build a world where anyone could outsource with predictability. Five years later, Aloa has grown to a 7-figure/year business as a bootstrapped startup. David is also the Co-Founder of Fifth Star Funds, a venture philanthropy fund in Chicago investing in Black tech founders to help bridge the funding inequality gap. To date, Fifth Star has raised 7-figures and has invested in over 20 founders. David serves as a Co-Founder and Product Lead for his third company, Bracketology, America’s largest platform for reality TV fantasy gaming (think fantasy football but for The Bachelor). While running his companies, David lives as a digital nomad, currently living in South America to learn Spanish.
Thank you so much for joining us!
What motivated you to launch Aloa, Fifth Star Funds, & Bracketology?
I’ve always been passionate about startups, about building companies/things. I find it to be really fun, a way to challenge my creativity and provide an endless path of learnings. My first company I tried starting in college failed, but I learned a ton from it. I then actually tried going the corporate route, but after not getting a return offer from my internship nor acceptance to any job applications, I went back to my roots and decided to invest in myself and do something that made me excited to wake up every day. Aloa was that answer — it was a no-brainer. At the end of the day, I was having fun, I was excited, and I knew that getting back into entrepreneurship was the right path for me. The connections I made through Aloa have already opened up so many doors, including helping start Fifth Star Funds as well as meeting the wonderful original founders of Bach Bracket, joining their team and rebranding into Bracketology. I guess that is a long way to say that, quite simply, the passion motivated me. The passion to build, the passion to create cool services, the passion to build something from nothing; that is what keeps me going.
What is it that excites you about what you’re building?
I think each of my projects presents a unique area of excitement. With Aloa, it’s about living out the entrepreneurial dream. I’m honored and privileged to be surrounded by the team I’m part of, and we really think we’re onto something. While we’re doing 7/figures per year, I wouldn’t yet say we have hit product-market fit. We have a lot of space to go, which is exciting. We want to change the world, the way people work with those around the globe, the way people innovate. I think we’re on the right track, but we of course still have a ton to learn.
With Fifth Star Funds, it’s about the opportunity to give back. For me, intertwining philanthropy within my day-to-day life is an important moral I live by. I don’t want to just do philanthropy when I ‘make it’ one day, I want to do it even when it is tiring and when I feel like I don’t have time. It’s important to me. Seeing the opportunity we’re creating for founders in Chicago is really what excites me about it. I know the rush of entrepreneurship, the addictive nature of this space. To give others the opportunity to explore their passion, idea, business — it’s a dream come true.
Lastly, Bracketology is just pure fun. It’s so different from anything I’ve ever done, an industry too that is so foreign to me. I’m not a big TV guy, nor a social media person, so being in this space is fascinating. I’m learning so much every day, it’s so much fun. I also get to work with my best friend of 20+ years, Jonah Fialkow, so it’s hard to not be excited about what we’re doing. We’re creating the next wave of reality TV entertainment, some cool things are around the corner.
What has been your biggest challenge when growing your business?
I think the biggest challenge is an emotional challenge: not comparing yourself to others. When you jump into the startup game, you need to know that you’re going to go through extreme ups and downs. One second you feel on top of the world and the next you’re questioning everything. Especially in today’s world with social media, it’s really hard to not compare yourself to others. I try my best not to, but sometimes you still do and it can make the venture feel lonely and tough. At the end of the day, it takes 10 years to build an overnight success. I’m not driven/motivated by instant gratification, so I’m committed to the long haul and the learnings I’ll gather on the way, but every so often, you can get dragged down by envisioning alternative realities… it can be dangerously captivating.
What are your future plans for all three organizations?
I think my plan for all three businesses looks a bit different. For Aloa, we want to grow ourselves into a conglomerate. We don’t intend to take on investment and don’t intend to sell — we want to keep growing, expanding our services, and eventually compete at the level of the Deloitte’s and EY’s of the world, helping some of the biggest companies in the world efficiently work in a globally connected workforce.
For Fifth Star Funds, it’s about making a true impact. We want to expand beyond Chicago and build a funnel of entrepreneurs that helps transform the racial wealth gap. We’re on the right path, so I’m excited to see where our organization goes in the next five years.
When it comes to Bracketology, we want to scale in a similar path as fantasy sports. We want to build the ESPN of reality TV. Any way we can more quickly get there, whether it be funding or strategic partners/acquisitions, we’re here for it. We’re at the early stages, we have a long way to go, but it’s no-doubt an exciting roadmap ahead.
If you had to share, “words of wisdom,” with a Founder who’s about to start their own startup, what would they be?
My favorite startup line is from Uri Levine, founder of Waze: “Fall in love with the problem, not the solution.” I love this line because it helps keep you grounded; it ensures that you aren’t chasing the money. If you’re money hungry (solution-oriented), then you’re going to have a tough path ahead of you. Each failure will hurt, each week will feel like time slipping through your fingers. When you’re in love with the problem, you’re in love with the vision you’re set out to achieve, you’re in love with the process, you’re in love with the learnings. Each failure is no longer a failure but simply another way that didn’t work, bringing you one step closer to the true solution. If you aren’t in love with the problem you are solving, then I’d take a step back to assess why you’re building what you’re building and what is driving you to ensure you make it through the inevitable hard times you’ll face.
How can our readers follow you on social media?
There are a few ways! For Aloa, feel free to go directly to our website to check out our blog and sign up for our newsletter.
Twitter:
- David Pawlan — @DavidPawlan
- Aloa — @aloalabs
- Fifth Star Funds — @fifthstarfunds
- Bracketology — @bracketologytv
This was very insightful. Thank you so much for joining us!
