The Changelog: Software Development, Open Source Chasing that next BIG thing (Interview)
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May 1, 2025 Drew Wilson, a seasoned designer and engineer, shares his journey from building successful startups like Plasso, acquired by GoDaddy, to his current role as Head of Design at Clerk. He reflects on the challenges of entrepreneurship, including navigating the complexities of banking innovation with his app Letter. Drew discusses the importance of resilience, the excitement around the next generation of Heroku, and the innovative tool Opacity, which bridges design and development. His insights on the evolving tech landscape are both inspiring and thought-provoking.
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Skills Crucial for Product Managers
- Product managers lacking engineering, design, or sales skills often lower team effectiveness significantly.
- Such roles without these skills add little value and can cause large product team layoffs.
From Startup Sale to Bank Founder
- Drew sold Plaso to GoDaddy and used the proceeds to start Letter, a bank for high net worth individuals with a modern app experience.
- Despite banking inexperience, he learned fast through CEOs and partners, building a lending platform with programmatic decisioning.
Why Letter Bank Failed
- Letter bank ultimately failed due to running out of money and approaching the market incorrectly.
- The exit of a major investor and Silicon Valley Bank's failure worsened conditions, leading to shutdown in early 2023.