Matt Mickiewicz and His Journey Across 99designs and Beyond
Matt Mickiewicz might not be a household name, but in the tech and business world, he’s a force to reckon with. A Canadian serial entrepreneur with roots in Poland, Matt Mickiewicz is widely recognised for his ventures that include SitePoint, 99designs, Hired, and Flippa. Not only has he built businesses that collectively hold valuations exceeding $1 billion, but his innovative approach to entrepreneurship has also earned him the admiration of aspiring founders and business leaders across the globe.
Early Beginnings of an Entrepreneurial Mind
Born in Poland in 1983, The early years of Matt Mickiewicz were shaped by significant challenges. His family fled communism to settle in Vancouver, Canada. Adjusting to a new culture and surmounting language barriers, Matt focused on academics and nurtured a curiosity for business early on. Inspired by successful figures like Bill Gates, he began exploring entrepreneurship as a teenager.
During high school, before even considering traditional career paths, Matt laid the groundwork for what would be a monumental career. He launched SitePoint, a web development resource in 1999, and achieved remarkable success at just 16 years old. It was clear early on that higher education wasn’t part of Matt’s trajectory. Citing the high opportunity cost of university, he opted instead for self-education—reading rigorously and seeking hands-on experiences in entrepreneurship.
This decision paid off. By the time he graduated high school, Matt was making sizeable ad sales from companies. On lunch breaks, he’d seal deals worth thousands—making far more than any typical teenager with a part-time job. From there, his story only became more impressive.
The Creative Force Behind 99designs
While Matt co-founded several thrilling ventures, 99designs remains the flagship of his career. Born from the SitePoint forums, 99designs initially started as an organic idea. Around 2006–2007, designers in the SitePoint community began engaging in “Photoshop tennis,” an informal design competition. This concept evolved quickly when members suggested offering cash prizes for real projects.
Matt and his team noticed the demand for these contests and turned them into the thriving marketplace we now know as 99designs. Key milestones in its evolution include:
Simplistic Beginnings
99designs began as an additional platform feature within SitePoint called “contests,” where users paid a $20 fee to host design challenges.
Rapid Growth
With immense traction from millions of SitePoint’s unique monthly visitors, they soon developed a standalone platform for 99designs.
Scaling Up
By focusing solely on graphic design, the platform paid out over $200 million to freelance designers worldwide. It raised $35 million in Series A funding from Accel Partners within three years and later expanded globally.
A Fresh Approach to Graphic Design
Unlike traditional hiring models, 99designs leveraged crowdsourcing to solve common design needs for companies big and small. Businesses could create contests, post project descriptions, and designers worldwide competed to offer the best design. The winner received the prize money while clients walked away with their desired artwork. These contests spanned diverse needs—from logos and wine labels to car wraps and websites.
The success of 99designs lies in its laser-sharp focus. When asked why the platform exclusively targets graphic design, Matt pointed out the importance of doing one thing exceptionally well. Rather than diluting its brand by expanding into other freelancing service categories like writing or development, 99designs concentrated its resources entirely on delivering unmatched design excellence.
Hired and Tackling Recruitment Challenges
While scaling 99designs, Matt Mickiewicz faced significant hurdles in recruiting engineers and creative talent. Ineffective job boards offered irrelevant resumes, while agency recruiters charged exorbitant fees with low success rates. Recognising this industrial inefficiency as a pain point faced by many CEOs and entrepreneurs, Matt turned the problem into an opportunity and co-founded Hired in 2012.
Hired created a curated marketplace where tech companies could connect with top-tier software engineers, designers, and analysts. It revolutionised hiring with transparency, allowing candidates to see offers upfront, including salary ranges and other details. Within just 30 months, Hired launched in 20 different markets worldwide and was recognised by Forbes as one of the “100 Most Promising Companies in America.”
Over its lifecycle:
- Hired raised $150 million in venture capital.
- The platform grew to employ over 250 staff.
- It generated millions in recurring revenue, firmly establishing itself as a go-to solution in tech recruitment.
Though acquired by LHH Recruitment Solutions in 2024, Hired remains a testament to Matt’s ability to identify industry inefficiencies and disrupt them with innovation.
From Flippa to Angel Investor
Another iconic venture co-founded by Matt Mickiewicz is Flippa, a global marketplace for buying and selling online businesses, websites, mobile apps, and domain names. Known as the “investment bank for the 99%,” Flippa has facilitated over $7 billion in buyer interest. It has empowered small business owners and digital entrepreneurs alike, delivering unprecedented transparency and accessibility to the online marketplace.
After stepping away from active CEO roles, Matt has turned his focus to angel investing and mentoring startups. With over 20 advisories under his belt, including companies like Optimizely, Gusto, and PhenomPeople, he contributes deeply to the tech ecosystem. His guidance style empowers founders to arrive at their own informed decisions instead of following prescriptive advice, encouraging creativity and independent problem-solving.
Matt’s Philosophies and Leadership Lessons
Matt Mickiewicz’s entrepreneurial philosophy aligns with innovation, adaptability, and focus. Here are some standout lessons from his career:
Seek Gaps and Solve Problems
Matt’s ventures stem from his ability to turn problems into business opportunities. From recruitment challenges to graphic design industry inefficiencies, his ability to identify and resolve gaps has driven his success.
Focus on Excellence
By concentrating solely on one domain—like graphic design with 99designs—Matt ensured that resources, customers, and employees all aligned towards a single goal. This intensified focus directly contributed to scaling the businesses.
Prioritise Extraordinary Customer Service
Matt revealed that 99designs depended primarily on word-of-mouth promotion for its first three years. Its success underscores how exceptional customer experiences resonate more than traditional marketing campaigns.
Trust Your Gut
Opting not to pursue higher education, Matt relied heavily on self-teaching, books, and firsthand experiences. Trusting his instincts has played a pivotal role in commanding the businesses he’s led.
A Legacy of Disruption and Community-Building
Matt Mickiewicz is not just another entrepreneur; he’s an architect of platforms that empower freelancers, job seekers, and small business owners to succeed. Whether through 99designs, Hired, or Flippa, his ventures continue to leave a lasting impact by bridging gaps where traditional industries fall short.
Passionate about learning and constantly evolving, Matt symbolises what it means to be a lifelong innovator. During his journey, he also took up flying as a hobby—yet another example of his relentless drive to seek challenges and expand his horizons.
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