Ben Sheppard
Inside StartupsReal-world lessons on startup strategy, enterprise deals, negotiation, and founder coaching — from someone who’s lived it.
| Platform |  | Pricing | Only free issues | Publishes | Twice weekly |
|---|---|---|---|---|---|
| Issues | 28 | Subscribers | Read | sheppardb.substack.com |
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Latest Issues
Recent posts by this newsletter. Browse the email archive.
Building Smarter Startups
This month’s newsletter brings together a mix of ideas, practical learning, and a couple of projects worth paying attention to.
Zoom Out: We’ve Seen This Before
If you spend enough time watching technology cycles, you start to recognize the rhythm. A new capability emerges, it accelerates at breakneck speed, and it captures the collective imagination. Then, almost immediately, come the confident, a...
The Hardest Stage of a Startup Is the One Before You Have Anything
At a New York DealBook Summit in 2024, Jeff Bezos offered a stark reminder of how difficult the earliest stage of building Amazon was. Speaking about his experience raising seed capital, Bezos said, “I had to take 60 meetings … It was basic...
Scaling the Backbone
Growth is exciting. New customers. Expanding teams. Bigger opportunities. More complexity. At its best, scaling is a sign that something is working.
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Authors
The writers behind this newsletter.
Ben Sheppard is a Startup coach. 4x founder, 1 exit. Co-founder at Silta Finance. I help founders scale with clarity—closing enterprise deals, raising capital, and navigating the messy middle with focus, precision, and real-world experience.
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