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 | Weekly |
|---|---|---|---|---|---|
| Issues | 33 | Founded | 2 years ago | Last Issue | 7 days ago |
| Active | |||||
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sheppardb.substack.comLatest Issues
Increase Your Rate of Failure to Get Better Outcomes
Steven Bartlett had a guest on his podcast recently — Bruno Fernandes, Manchester United footballer — and the phrase came up in that conversation. It stopped me, because it’s one of those things that gets repeated in founder circles like a...
Chasing a Wild Boar at 5am Was the Easy Part
There are moments in life where you learn something about yourself that no career milestone, no relationship, no motivational quote and no amount of external validation can teach you. You only discover it by putting yourself somewhere deepl...
Designing for the Demand You Can Already See
A few months ago I launched another company. It’s called Inside Startups, and it’s a coaching and fractional leadership practice built with a small group of operators I’ve known and trusted for years.
I didn’t need to do this. That’s worth...
Do you want to eat early or late?
Do you want to eat early or late? On the surface, it is a straightforward question. In reality, it rarely is. In business, very little sits neatly under one lamp with all the light shining clearly in one place. Nothing is ever entirely blac...
Sustainable Growth Starts With You
What’s Inside
This month explores the unsexy side of building. Three pieces on capital, oceans, and burnout might not sound like natural companions, but they share something important: they’re all about the decisions that don’t feel urg...
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| Subscribers | Engagement | 64 | Monthly Web Visits | ||
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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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