Advising founders on go to market, strategy and M&A. Co-founder and CEO of Skyp.ai.
Founder-led sales
+1
Mar 16, 2026
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6 min read
When your product fails its customers, the instinct is to apologize with discounts. Alterra tried something smarter.
AI Outbound
+7
Mar 13, 2026
3 min read
The job isn’t “post more.” It’s create signal—and turn it into conversations.
+5
Mar 9, 2026
4 min read
Horizontal is fine. Horizontal messaging is fatal.
Mar 6, 2026
5 min read
If you sound like everyone else, you’ll compete like everyone else. Change the angle.
Mar 2, 2026
First-order pain is annoying. Second-order pain is expensive.
Feb 27, 2026
Wisdom from working with 1,000 B2B startups–and starting 3
Feb 23, 2026
A longer sequence isn’t a strategy. It’s just more delivery of the same wrong message.
Sales Automation
+4
Feb 20, 2026
What someone who has gone $0-1mm ARR multiple times worries about
Feb 13, 2026
If you’re still guessing ICP and messaging, “sales mode” just makes you wrong faster.
Feb 9, 2026
Nice sounds optional. Specific sounds like a decision.
Feb 6, 2026
If it reads like a press release, it won’t close deals.
Feb 2, 2026
Stop pitching features. Pitch the next conversation your buyer actually wants to have.
Jan 30, 2026
and Reward the Weirdly Helpful...
Jan 26, 2026
Don't treat conferences like participation trophies.
Jan 23, 2026
Most outbound doesn’t fail on the offer. It fails on the ask.
Jan 19, 2026
The fastest “growth channel” is shrinking time-to-first-value.
Jan 16, 2026
Switching platforms doesn’t fix ICP, offer, or message. It just gives you a fresh place to be confused.
Jan 12, 2026
Your product isn’t the offer. The offer is how you package certainty
Jan 9, 2026
The fastest way to trust is to be useful first.
Jan 5, 2026
8 min read
One channel mastered will outproduce three channels “tested.”
Jan 2, 2026
Separate your testing lane from your scaling lane.
Dec 29, 2025
Early-stage proof needs to be specific, not impressive.
Dec 26, 2025
A simple model that tells you how many emails you need—without vibes.
Dec 22, 2025
Turn generic claims into specific reasons to reply.
Dec 19, 2025
How to turn unfair insight into Scalable GTM
