Written by Sara Guo I 3 min read

In a world where entrepreneurship often conjures images of Silicon Valley tech wizards and flashy startup launches, Andrew Wilkinson's story is a refreshing departure from the norm. 

Wilkinson's journey into the world of business has been anything but conventional, marked by audacious decisions and a keen eye for hidden opportunities. From humble beginnings as a barista to becoming a key player in the business world, Wilkinson's story is a testament to thinking outside the box and daring to lead a different path. 

Andrew Wilkinson and the Founding Story of Tiny

In 2006, at the young age of 20, Andrew Wilkinson founded MetaLab, a design agency based in Vancouver, Canada, that primarily focused on crafting web and mobile applications. Wilkinson's innovative prowess earned MetaLab prestigious clients like Slack, Google, and Shopify

In just three years, MetaLab generated $200,000 in profit, and within six years, revenue soared to $3 million. The profits were reinvested in launching businesses that addressed real pain points, forming what we know today as Tiny (founded in 2007). However, the pivotal shift occurred in 2013 when the company transitioned from launching businesses to acquiring them. This marked a transformative moment for the company, shifting from an Agency-style business – defined by taking profits to build other ventures – to a model more akin to a holding company (Holdco). Today, Tiny boasts a diverse portfolio of over 30 businesses with a cumulative valuation of almost $1 billion, firmly self-funded. It’s no wonder that Tiny is often called the “Berkshire Hathway of internet businesses.”

Over the years, Tiny's portfolio has grown, encompassing several businesses that have thrived under its stewardship, including Dribbble, and Designer News. Even with this accelerating growth, MetaLab is still operating, and one of the largest design agencies in the world with $60M in annual revenue. 

Tiny’s Portfolio Companies

Tiny's investment strategy has consistently delivered impressive results. With an average deal size of $19.32 million and involvement in 108 total deals, Tiny has strategically ventured into various industries. 

Tiny currently invests in five industries (ranked from highest to lowest # of companies invested in the specific industry); 

(1) Information Technology

(2) Consumer Products and Services

(3) Business Products and Services

(4) Healthcare

(5) Materials and Resources

This can be easily explained by Wilkinson’s strong interest in technology and his conviction that, in the wake of the ongoing digital revolution, technology and internet-based enterprises are endowed with remarkable resilience and longevity.

Statistics on Tiny’s portfolio 

Tiny’s Selection Criteria

Wilkinson is known for his distinct approach to selecting “New Zealand” Companies. 

Source: Andrew Wilkinson on Twitter

New Zealand companies offer long-term growth potential and can scale up effortlessly, multiplying their revenue by up to ten times without needing additional personnel. This sets them apart from offline or service businesses, where business growth is directly linked to the expansion of human capital.

Best Practices for Hiring a CEO

Wilkinson is often asked whether or not founders like himself would also make great CEO’s and here’s what he has to say:

“I’d say there’s really no rules. There’s only experience. I think for myself, I realized pretty quickly that I was a great zero to one person. I loved starting things, but, and I really loved operating at a large scale, but I didn’t like the in-between. And for me personally, I actually didn’t like managing large groups of people. I loved managing a 20-person company, but I don’t really enjoy managing a hundred or a thousand-person company. And so it was much better for me to hire CEOs who enjoyed that phase of growth and operations” – Andrew Wilkinson on the We Study Billionaires Podcast

Wilkinson's approach to hiring CEOs is rooted in a deep understanding of the roles within an organization. He recognizes the value of innovators, remixers, scalers, and optimizers, depending on the company's growth stage. 

Wilkinson believes that when hiring a CEO, points 3 and 4 should be prioritized. Source: Twitter

In addition to rigorous background checks costing upwards of $10K, recurring questions Wilkinson likes to ask include:

  • “Would we let this person babysit our kids?”
  • “Do we feel excited or drained after we leave a meeting with them?”
  • “Does anything not add up? Is there any cognitive dissonance?”

Check out this Twitter thread to see examples of CEOs Wilkinson has brought on board and why they stood out based on these criteria.

The Similarities Between Tiny and Onova

Started As An Agency Before Scaling

Both companies began as agency/consultancy firms, cultivating business models that are instantly profitable and cash flow positive. This foundational strength allowed them to chart their own course, unburdened by the need for external funding. The outcome? Unmatched freedom and control over the direction of the business.

Identifying Pain Points and Building Their Own Companies

Their journeys didn't stop at consultancy services; instead, they leveraged their profits to invest in building their own companies. Ones designed to tackle the very pain points they observed within their own organizations and from their clients. This unique positioning, as both observer and innovator, allowed them to craft businesses that addressed real-world problems.

Here are Onova’s solutions to the pain points experienced by the team and by clients.

Winning Together Fund

Pain Point: There's a lack of community feel in the realm of investing, with a high barrier to accessing alternative investments.

Solution: Founded by Onova Co-Founder, Victor Li, The Winning Together Fund is both a venture fund and a community of investors dedicated to supporting early-stage tech startups across various sectors, including SaaS, remote work, web3, and more.


Pain point: Onova has been running hackathons for many years with clients such as McDonald’s, BMO and HSBC. They explored dozens of third-party providers to host their hackathons, yet never found a singular platform that boasted a modern user interface while seamlessly connecting all the elements and components of a hackathon, all while bridging the gap between physical and virtual participants.

Solution: Onova created their own hackathon management platform in 24 hours at their semi-annual internal cottage trip. Earth was created to solve the needs of all stakeholders; Hackers wanted consolidated information, mentors aimed to give their best support, judges sought clear judging instructions, and organizers desired a single tool that could do it all. And, the platform was used in a recent client project, Capgemini x Google’s GenAI hackathon

Generative AI Hackathons

Pain point: The client, Capgemini, expressed a need to expedite the creation of Minimum Viable Products (MVPs) and simultaneously enhance their employees' proficiency in Generative AI, which includes platforms like Google Cloud's Vertex AI, Cohere's Command model, or Copy.ai's Workflows product.

Solution: Onova helped Capgemini organize its inaugural generative AI hackathon within a three-week timeframe, extending invitations to over a thousand employees across 29 countries worldwide. The objective was to encourage participants to envision new possibilities within the field of AI.

Entrepreneurs, Not Just Investors

Onova began investing in a broader spectrum of startups, taking minority stakes in over 15 companies. For both Tiny and Onova, their guiding principle remained consistent - they were entrepreneurs, not just funders. This investment approach wasn't about detached financial backing; it was about active involvement, offering guidance, expertise, and a network to help these startups thrive.

The Winning Together Fund’s investment thesis.

Co-Founding and Buying Companies

Onova is poised to not only nurture but also potentially co-found businesses together with external founders, further expanding their influence in the entrepreneurial landscape.

Looking Into The Future

Although founded ten years apart, both companies exemplify the spirit of forward-thinking entrepreneurship. They've sculpted a unique path marked by self-reliance, innovation, and the unwavering commitment to building businesses that prosper and serve as solutions to real-world challenges. 

In an era where quick wins and external funding often steal the spotlight, Tiny and Onova stand as a testament to the enduring power of visionary founders, and it’s exciting to see what's in store for both companies.

Interested in seeing how we can support you and your business in your innovation initiatives? Book an introductory call with Victor Li, Founder & CEO of Onova.
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