Neil Patel

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Entrepreneurs like Oli Cavanagh seize opportunities to innovate and solve real-world problems in a world where technology constantly evolves. From his beginnings in Ireland, Oli’s journey has been marked by a series of ventures, each offering valuable lessons and insights into the world of startups and business.

In an exclusive interview, Oli Cavanagh shares the highlights of his entrepreneurial odyssey and his latest endeavor, Strikepay, which is poised to revolutionize the way we tip service providers.

Listen to the full podcast episode and review the transcript here.

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Early Beginnings and Lessons Learned

Born in Malaysia and raised in Ireland, Oli’s multicultural upbringing laid the foundation for his diverse perspective on business and life.

Despite being born to medical professionals, he veered away from the healthcare path, driven by an early fascination with technology. “My first computer, a Sinclair ZX81, sparked my interest in tech,” Oli reminisces.

Oli’s entrepreneurial journey began with a startup during the Y2K era, where his company’s asset discovery software proved invaluable to banks. That company was acquired by a company in San Diego called Peregrine Systems.

The Peregrine Acquisition

Peregrine was only interested in the software, so they basically dropped the whole service aspect of the business, which comprised more than 50% of the company’s revenue. Oli was based in the US, and his co-founder worked out of London.

Oli and his co-founder could see that they really needed the services division, which was a few million dollars worth of business that remained unaddressed by Peregrine. The company initially picked up all that services business and hit the ground running.

They then acquired an encryption tech company and sold out in 2001. Following the purchase, Oli learned the intricacies of M&As, emphasizing the importance of cash in such deals.

Although, on paper, the acquisition was worth $50M, it involved a minimal amount of cash, and the IPO was due to happen in late 2001, but 9/11 happened, and it was called off.

As Oli recalls, at the time, he didn’t have much knowledge of the workings of M&As or how the acquisition deal should be structured in terms of cash, equity, and IPO. This lesson would prove invaluable in subsequent ventures.

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Spotting Opportunities and Timing – Founding AllDataSystems

Soon after, Oli moved to Dublin, Ireland, which was becoming, as Oli terms it, “really hot in the tech space.” All the big tech companies were moving there for their European head offices. Several factors contributed to this situation, such as the availability of labor and tax benefits.

Oli’s keen eye for spotting market gaps led him to found AllDataSystems, a pioneering venture in aggregating automotive data for various businesses.

Recognizing the inefficiencies in disparate data management systems, Oli created a SaaS model that garnered widespread adoption. Its success underscored the significance of addressing pressing market needs efficiently.

At the time, different businesses in sectors like insurance, car finance, banks, and several others had in-house teams doing research to build a database of the products they were offering, complete with images and other information.

Oli came up with the idea to create a team and white-label it as a SaaS model for all these businesses. They ended up creating the best live database or a SaaS feed that included everything automotive, banks, insurance companies, and motoring websites.

These businesses started to pay a monthly fee to access the database, which gave AllDataSystems a monopoly in the country since every B2B player would take the information on board.

Just as they were poised to expand the company and take it to the UK, Europe, and other countries, Oli and his co-founder received an offer for acquisition from AutoFinder.

Today, it is a part of Mediahuis Ireland (formally Independent News and Media, or INM). Oli considers selling the company an easy decision.

Pliba – Oli’s Next Venture

However, not all ventures would yield immediate success. Pliba, the world’s first mobile booking platform, was ahead of its time, launching before smartphones became ubiquitous.

Despite the innovative concept, Pliba faltered due to technological limitations and insufficient market readiness, highlighting the importance of timing in entrepreneurial endeavors.

As Oli reminisces, he foresaw a time when people would use their mobile phones to book everything they needed, from taxis, restaurants, massage services, and haircuts.

To make that happen, Oli and his co-founder built a WAP platform, taking feeds from some of the biggest booking platforms in the world.

However, when the duo went to the biggest hostel booking platform in the world,, they saw that 100% of their bookings were made through desktops. They didn’t have a mobile interface and couldn’t understand the potential of the concept. Even so, they offered an XML feed.

Within the next few days, the first-ever mobile hospital booking was made through the Pliba platform. The name PLIBA was designed as the acronym for Please Let It Be Available. Pliba went on to make the world’s first booking for a range of services like a table at a restaurant, taxis, and more.

Challenges Pliba Faced

Soon, the platform was offering close to 52,000 different services that customers could book. However, the most significant challenge they faced was they couldn’t get people to use it. Also, only 2G internet was available, data fee costs were huge, and the internet was too slow.

Unfortunately, Oli and his co-founder ran out of funding, and the concept simply did not catch on because it was ahead of its time. Then the iPhone took off, and today, mobile apps are doing just what Pliba was offering.

In retrospect, Oli considers their crucial mistake was not believing in the project enough to quit their day jobs. He imparts a lesson to other upcoming entrepreneurs: don’t work on a project you 100% don’t believe in.

The Genesis of Flender

Oli was using a platform called Linked Finance that did a lot of lending to businesses. It was a peer-to-peer finance marketplace for business funding, and it successfully disrupted traditional banking with easier access to business loans.

Oli recalls how he earned 10% to 11% returns and that the company had no competitors. When he and his co-founders came up with the concept for Flender, the idea was not to take the client base but to grow the overall market since it was big enough for two players.

That’s how Flender created a single end-to-end platform that they were able to do in 24 hours, which is what the biggest traditional banks took ten weeks to do. Flender has since loaned out over $60M in total funding.

From Failure to Innovation: The Birth of Strikepay

Reflecting on personal experiences during the cashless transition, Oli envisioned a solution to facilitate digital tipping seamlessly. Thus, Strikepay was born—a platform revolutionizing tipping through personalized, portable payment terminals.

Strikepay’s innovative approach allows service providers to receive tips effortlessly, addressing the growing trend toward cashless transactions. Strikepay aims to empower millions of service professionals worldwide by leveraging scalable technology and a unique business model.

Oli recalls how he saw the need for a portable payment terminal that was compact enough, low-cost, and economical in terms of transaction fees. That’s how he came up with the model, which is to have devices that thousands of employees of businesses can physically carry.

People can tap it to tip them or scan a QR code from Strikepay. The concept is very scalable and not chargeable, so they could give a free product that allowed instant activation. It’s essentially a personal tipping terminal that can be up and working within 30 seconds, making it the world’s only instant activation and payment terminal.

Strikepay has patent protection and charges a monthly SaaS fee to each active user who’s actively getting payments or tips, plus a 6% transaction fee.

Oli agrees that the fee is on the higher side but that users are willing to cover it because they aren’t really price-sensitive when it comes to this kind of transaction.

Further, around 95% of the time, the person making the payment covers the fees, making it very attractive for the actual user or employee in a salon or hotel serving the customers.

As for reach, Oli reveals how 60 million users in the UK and the US rely on tips and can use a personal tipping terminal that can be set up instantly. The USP is that it is incredibly low-cost.

Strikepay has raised a total of €2.1M or $2.28M over two funding rounds and is now raising to go into the US market.

Storytelling is everything, which is something that Oli Cavanagh was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend Peter Thiel (see it here), where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

In Conclusion

Oli’s entrepreneurial journey exemplifies resilience, innovation, and a relentless pursuit of solutions. From humble beginnings to groundbreaking ventures, Oli’s story inspires aspiring entrepreneurs to dream big, seize opportunities, and make a lasting impact on the world.

As Strikepay continues to disrupt the tipping industry, Oli’s vision of a cashless future becomes increasingly tangible—a testament to the power of innovation in shaping the world we live in.

Listen to the full podcast episode to know more, including:

  • Success often hinges on timing. Identifying market trends and technological advancements can dictate the success or failure of a venture.
  • Successful businesses solve tangible problems. Entrepreneurs can carve out a niche and establish a strong foothold by addressing pressing market needs efficiently.
  • Failure is not the end but a stepping stone to success. Learning from setbacks and adapting strategies are crucial for long-term growth.
  • Demonstrating the viability of an idea through a proof of concept can instill investor confidence and pave the way for sustainable growth.
  • Embracing innovation is vital to staying ahead in a dynamic marketplace. Continuously seeking new opportunities and adapting to changing consumer behaviors is essential for long-term success.
  • Aim to make a meaningful impact with your ventures, like Strikepay’s revolutionizing of tipping practices.
  • Despite challenges, maintain resilience and determination to pursue your vision relentlessly.



For a winning deck, see the commentary on a pitch deck from an Uber competitor that has raised over $400M (see it here). 

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The Ultimate Guide To Pitch Decks

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.


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Neil Patel

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