Building a high-performance growth machine

Mastering the Startup Journey: Six Pivotal Lessons from Wayflyer’s Ascent to $100M Revenue

Aidan Corbett, CEO and Co-Founder of Wayflyer, shared six pivotal “lessons” – essentially mistakes – that guided his company’s journey to $100 million in revenue. Wayflyer, established in 2019, specializes in providing working capital to small businesses, effectively addressing cash flow challenges. Mr. Corbett described their service as a “sleep aid for entrepreneurs,” ensuring founders can rest easier with a financial partner.

The company achieved $100 million in revenue within five years. During this period, Wayflyer deployed over $5 billion to more than 5,000 businesses globally. In the most recent month alone, they deployed $200 million across five different geographies, demonstrating significant scale and impact in the financial sector.

Mr. Corbett’s first lesson emphasized positioning a product as a painkiller, not merely a vitamin. Painkillers inherently simplify marketing and sales, as customers actively seek solutions to urgent problems. This approach also leads to lower churn rates, even during tough economic times, making the startup journey considerably smoother. Cybersecurity companies serve as a prime example of this indispensable product positioning.

The second crucial insight involves deeply understanding your company’s core equation. Founders must identify and analyze key variables such as conversion rates, customer acquisition costs (CAC), and customer lifetime value (LTV). Comprehending how these variables interact and the trade-offs involved, like balancing data collection for risk mitigation against its impact on onboarding conversion, is vital for effective tuning.

Thirdly, Mr. Corbett stressed the paramount importance of confronting difficult decisions promptly. He posited that a CEO’s effectiveness is directly linked to the number of hard choices they are willing to make each week. Delaying these critical decisions, a personal mistake that cost his company an estimated eight figures, can be severely detrimental. Building the habit of “running towards fires” is indispensable for rapid growth.

The fourth lesson advocates for hiring individuals exhibiting “high agency.” This trait is characterized by disagreeability, a strong bias for action, and exceptional clarity of thinking. Mr. Corbett offered a compelling thought experiment: who would you call if you were imprisoned in a foreign country? Screening for these specific qualities in the recruitment process has proven to be a transformative innovation for Wayflyer.

Fifth, Mr. Corbett strongly advised against bootstrapping a startup. While it might seem appealing, bootstrapping often carries significant drawbacks. Modern funding options, such as SAFEs and convertible notes, allow founders to maintain control without excessive early dilution. Bootstrapping can also lead to greater equity distribution to early team members and encourages short-term decisions, like consulting, which can delay product development.

Finally, the sixth lesson champions generalists over specialists, particularly during a company’s growth phases. Although there’s pressure to hire specialized roles as a business scales, generalists, especially those with a strong learning aptitude, are significantly empowered by AI. They reduce internal coordination costs and enable much faster execution, as individuals can seamlessly manage multiple functions without extensive inter-departmental meetings.

Mr. Corbett concluded by reiterating these six foundational principles: creating a painkiller product, mastering your company’s operational equation, proactively addressing hard decisions, recruiting for high agency, securing appropriate funding, and prioritizing versatile generalists. These insights are crucial for navigating the complexities of startup development and achieving sustainable, high-performance growth.