The Sure Shot Entrepreneur

Master Your Technical Edge, Solve the Right Problem, and Scale Big


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Andrew Cleland, Chief Investment Officer at Techstars, shares how the world’s leading accelerator invests in early-stage startups. He breaks down what makes a great founder, how Techstars selects startups from tens of thousands of applicants, and why a strong technical differentiator is crucial. Andrew reveals the most common reasons startups get rejected and how Techstars mentors founders to avoid early mistakes. He also talks about the biggest themes shaping the future of venture capital.

In this episode, you’ll learn:

[03:00] How Andrew’s background in consulting, startups, and venture capital led him to Techstars 

[07:34] How Techstars selects startups from thousands of applications—what matters most
[14:01] The #1 mistake founders make when applying to Techstars, and how to avoid
[20:50] Why founders need to build investor relationships early when thinking about fundraising
[26:04] Why the VC industry needs more transparency—and how that benefits founders

The non-profit organization Andrew is passionate about: Magic Bus

About Andrew Cleland

Andrew Cleland is the Chief Investment Officer at Techstars, where he oversees investment strategy, fundraising, and portfolio growth across Techstars’ global network of accelerators. With over two decades in venture capital and early-stage investing, he previously led investments at Comcast Ventures and Time Warner Investments. An INSEAD MBA graduate, Andrew has backed dozens of high-growth startups and is focused on empowering the next generation of global founders.

About Techstars

Techstars is one of the world’s leading startup accelerators, backing thousands of early-stage companies across 50+ accelerator programs worldwide. Since 2006, Techstars has helped launch 20+ unicorns, including SendGrid, DigitalOcean, Uber, Twilio, DataRobot and Outreach. The program provides mentorship, funding, and global networks to help startups scale fast.

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The Sure Shot EntrepreneurBy Gopi Rangan

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