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
The Pact
- Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:
- Follow, rate, and review us in your listening app
- Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe
- Secure your official TSP merchandise at https://shop.tsp.show/
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- Give us a public shout-out on LinkedIn or anywhere you have a social media following
Key links
Get your question in for our next Q&A episode: https://forms.gle/NZzgNWVLiFmwvFA2A
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/
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