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 | 35 | Founded | 2 years ago | Last Issue | 23 days ago |
| Active | |||||
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sheppardb.substack.comLatest Issues
The CEO Briefing Dashboard: What Broke, and What I Did About It
My tool for connecting everything across the business together so I can visualise it in a useful way, apply different metrics, and see the health of the business, what the team’s doing, how everything’s performing by function as we continue...
It Will Take the Job. It Won't Take You.
And how unevenly that change is actually landing. Some businesses are living inside it. Others have the tools sitting unused on every desktop.
Looking back at my own early career is a useful reference point. A lot of the work I did as a ju...
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...
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| Subscribers | Engagement | 63 | Monthly Web Visits | ||
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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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