Fail Wisdom Podcast: Turn Startup Failures into Success · Paul King: Startup Fail Wisdom: Insights from Founders and Entrepreneurs

Branding, Cybersecurity, and the Power of Delegation for Startup Success

·51 min·5 clips

Michael paid half a bitcoin to hackers after a ransomware attack wiped out his business files.

Michael Skepsis, founder of the graphic design and branding agency Handle, joins the podcast to share lessons from his entrepreneurial journey. He discusses his transition from designer to business owner and his recent venture into tech. Skepsis explains that Handle began over nine years ago when his wife, a graphic designer for IKEA, started taking freelance jobs during maternity leave and delegated the work to him. He recounts how the company name "Handle" was inspired by the Beyoncé song "Bootylicious" and the line "can you handle it." Skepsis details his decision to enter a sweat equity agreement with a client's beverage company, Gravity Seltzer, which is now a national brand in Australia. He describes a devastating ransomware attack that encrypted all of his company's files, presenting a demand for half a Bitcoin to unlock them. Facing the potential loss of six years of work, Skepsis made the controversial choice to pay the ransom and received a decryption key. He hired a cybersecurity professional from France for three months to overhaul his company's digital security protocols. This crisis led him to identify a flaw in using Trello for storing sensitive login information openly within his team. Skepsis and his team developed "Hide Notes," a Trello power-up that conceals private data like passwords within project boards. They built the app internally within a month and a half and launched it as a freemium product on the Trello marketplace. The app gained over 600 sign-ups in its first three months and now has paying customers across multiple global server locations. He emphasizes that branding is critical, advising founders to choose business names that are easy to pronounce and hint at the service offered, like "Handle" for branding or "Hide Notes" for security. Skepsis reveals he was diagnosed with dyslexia as an adult, which helped him understand his creative strengths and difficulties with tasks like reading analog clocks and managing finances. He stresses the importance of delegation, citing his own weakness with numbers and reliance on his wife, Georgina, to handle that side of the business. Skepsis advises using clear contracts, taking deposits, and implementing staged payments to mitigate the risk of clients not paying. For cybersecurity, he recommends regular backups, strong unique passwords, two-factor authentication, and investing in proper network security upfront. The conversation is casual and confessional, blending personal anecdotes with practical business advice. Founders interested in branding, cybersecurity horror stories, or bootstrapping a tech product will find this episode highly relatable. Listeners seeking a highly structured, data-driven analysis of business topics might find the conversational style too meandering.

As heard by us

Practical founder advice that ties branding, security, and delegation to real startup work.

Branding sits at the center of this one, but not as a slogan exercise. The discussion keeps circling back to names people can actually say, an identity that fits what the product does, and the way a founder's own annoyance can sharpen the idea.

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Why you'd press play

A founder chat on brand names, startup security basics, and delegating before the work hardens.

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