Sunny Ray talks with Jay Westlin of Fastener, a 13-year-old company that connects technology and service companies with media companies, while Westlin works from a Sprinter van with Starlink at his horse property in Santa Cruz. A journalism major who never became a journalist, Westlin built his career in business development, including time at Spin Media, before founding Fastener in 2013. He explains how COVID legitimized his van-based work style, why he believes relationships matter more than tweaking conversion rates, and how years of recorded call data and AI let him mechanize the business. He describes Osterman, the AI system that assigns tasks across an agentic CRM, and a client dashboard where pre-qualified introductions can be booked straight onto calendars. Westlin also shares the human cost of the shift, including letting go of two longtime team members, and says the change made the company far more profitable. He closes with advice for deal makers on mapping their networks and predicts agents will handle anything repeatable while humans supply taste, relationships, and context.
A 13-year-old business built on relationships now runs on AI, and its founder operates it from a van with Starlink.
What made you start Fastener in 2013?
I was a journalism major who never became a journalist. I became a business developer, and I was at a large venture-backed publisher where we owned Vibe and Spin. I knew all the publishers and the technology they needed, so I stepped back, started my own company, got clients, and helped them meet people. Thirteen years later I've mechanized that with AI.
How did working from a van start?
During COVID I had an office in Santa Monica, so I'd park my van next to the building and piggyback on the Wi-Fi, going inside with a mask for mail or meetings. After a year I asked why I needed to be there at all. Everyone I talked to was working from somewhere else too, so it legitimized working from anywhere.
Why do relationships matter more than a bought list?
I'm a people person, not someone chasing huge numbers and tweaking conversion. You can know roughly 150 people well, and turning that into action takes real work. So I tell clients to go to their own network first. If it's small, they can work with us, since we already have an established network and can get them in front of their ICP fast.
What changed when you brought AI into the company?
This summer the AI systems came together with my partner's understanding of our workflow, and now we ship code weekly instead of paying for code that arrived a quarter later. It made the company far more profitable, but it replaced people. I let go of two who had worked for me seven and ten years. It's not great, but you have to learn this game.
What makes an introduction pre-qualified at Fastener?
We've recorded calls for over five years and keep every introduction anonymized in a repository. Our AI system, Osterman, tasks us up. Clients upload a whitelist and blacklist, we reach out to the best matches, and whitelisted companies can book straight onto the client's calendar. Others get diverted to us to triage. We also capture the when and why, not just yes or no.
How do you monetize it?
We have about 50 clients who pay a monthly retainer, around 10 grand a month. They get access to the system and an introduction every single week from their whitelist. If it's working they stay for years, and if not they can leave and come back. Some clients are seasonal, so they drop off and return, like for Q4 advertising spend.
What can a deal maker do this week to get more from their network?
Step back and build a broader understanding of all your relationships and who would be useful to each other. Don't force a square peg into a round hole. Lay out all the pegs and holes, be opportunistic, find the frictionless matches, and reach out to introduce them. That turns into a flywheel you can't create all by yourself.
How much of a sales team's work will agents do in five years?
Potentially quite a lot. Agents can execute anything that can be identified and repeated, while the human brings taste, relationships, and broader context. If you feed that into your agent, it can do everything else. People leveraging AI are already ten times more powerful than those who aren't, and I think the gap keeps widening.
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