Although this venture ended when a teacher discovered his surreptitious methods of sourcing music, it gave Matt his first taste of entrepreneurship.

"It was very exciting, until a teacher busted me for my not-so-legal music sourcing methods. It was my first real taste of entrepreneurship, and I knew straight away that I was totally hooked."

After several attempts at different business ventures, Matt found success in the direct-to-consumer (DTC) and e-commerce space. This experience provided invaluable lessons and shaped his approach to business.

"When I say it aloud, I realise that my path to where I am today was anything but straightforward, but the lessons I’ve learnt along the way have been invaluable."

The entrepreneurial mindset

Matt's journey into entrepreneurship was driven by his natural ability to spot opportunities and his unique perspective on business. He recalls the influence of his academically brilliant brother and how their different approaches to opportunities shaped his vision.

"I think I've always 'seen things differently,' so becoming an entrepreneur wasn’t really a conscious decision, just something that felt natural and inevitable."

Despite experiencing setbacks, Matt's vision has only grown larger over the years. He maintains a resilient attitude towards business failures, seeing them as opportunities to build something new.

Securing funding for The Shirt Society

One of Matt's notable ventures, The Shirt Society, had an interesting fundraising journey. Instead of actively seeking investment, he attracted investors through his efforts to publicise the business's progress online. This led to a successful pitch to Manchester-based angel investors:

"I met with them, and a couple of days later, I had a deal on the table. I believe they saw that I had a clear vision for the business, recognised the obstacles, and understood the market, which instilled a lot of confidence."

Overcoming challenges in early ventures

Matt's experiences with his first ventures, We Are Gntlmen and The Shirt Society, highlighted the complexities of scaling DTC and e-commerce brands. Managing physical stock posed significant challenges, and investors were often hesitant to back early-stage e-commerce businesses. However, Matt's innovative approach to The Shirt Society, focusing on the payments and technology platform, helped overcome these obstacles:

"Instead of warehousing and operations, it was always about the payments and the technology platform that powered it. I viewed it as a tech-platform business powering a DTC subscription brand, which created a lot of opportunities."

Lemon: addressing SMB challenges

Lemon was born out of a desire to solve two significant issues faced by small and medium-sized businesses (SMBs): lack of clarity and overspending on software subscriptions. Lemon offers a free SaaS management platform that simplifies how businesses track and manage their software subscriptions. Additionally, it provides a software financing solution that removes cost barriers to technological adoption.

"Lemon enables SaaS companies to get paid for annual plans while allowing businesses to make monthly payments, saving them around 20–40% in the process. It’s a game-changer for SMBs."

Advice for aspiring entrepreneurs

Matt shares three key lessons for aspiring entrepreneurs looking to make a significant impact in the tech industry:

• Find something you have a deep interest in and identify its gaps.
• Speak to customers extensively before writing a single line of code.
• Don’t be afraid to pivot – continuous experimentation is crucial to reaching your goal.

Future goals for Lemon

Looking ahead, Lemon is focused on expanding its innovative software financing product, with a target of £250 million in lending commitments. Matt sees significant value in this solution, which can provide cost savings to end-users, streamline operations for banks, and revolutionise sales strategies for software teams.

"We are well underway with these plans, so we encourage anyone interested in supporting the project to reach out and connect with us directly."

Matt Bird's journey from selling CDs in school to co-founding Lemon demonstrates the resilience and innovative thinking required to succeed as an entrepreneur. His story offers valuable lessons for startups looking to navigate the challenges of the tech industry.