Pre-seed founders want explosive growth early on, but are you following the wrong playbook too soon? These days strategies, acronyms, and well-intended advice are everywhere, but today's guest argues that the path forward is a simple one: talk to customers, run experiments, and embrace rejection as part of the journey.

In this episode, Yaniv Bernstein speaks to guest Ashley Smith (ex-Twilio, Parse, GitLab, GitHub, and now General Partner at Vermilion Cliffs) and unpacks what it really takes for your startup to go from zero to one. Ashley has been at the helm of some of the most successful developer tool companies in the last decade and now invests in the next generation of technical founders. She shares raw insights from the trenches on how to build community, experiment with growth, and keep your startup alive through grit and iteration.

In this episode, you will:

Learn why investor playbooks can be dangerous for early-stage founders
Understand why customer conversations matter more than LinkedIn hot takes
Discover how product and marketing should be treated as one cohesive strategy
Explore how companies like Twilio, Parse, and GitLab grew by leaning into community, content, and relentless product shipping
See why hiring generalists and “specialists in experimentation” is the best early-stage move
Gain tactical tips on creating authentic founder content in the age of AI slop
Embrace rejection as a natural (and necessary) part of fundraising and early customer acquisition

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Key links

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The Startup Podcast website: https://www.tsp.show/episodes/

Learn more about Chris and Yaniv

Work 1:1 with Chris: http://chrissaad.com/advisory/

Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/

Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur

Intro Voice: Jeremiah Owyang https://web-strategist.com/

Growing a Pre-Seed Startup? This Is The Core Knowledge You Need w/ Ashley Smith

The Startup Podcast